ZEITSCHRIFT FÜR NATURFORSCHUNG

SECTION C 1

B I O S C I E N C E S

Council Editorial Board

E . BÜNNING, Tübingen A. HAGER, Tübingen A. BUTENANDT, München W. HASSELBACH, Heidelberg M. E I G E N , Göttingen P . KAELSON, Marburg W. GENTNER, Heidelberg F . KAUDEWITZ, München

E , W E C K E R , Würzburg

Advisory Editorial Board P . BÖGER, Konstanz H . SCHIMASSEK, Heidelberg D . BÜCKMANN, Ulm D . SCHTTLTE-FROHLINDE, Mülheim/R. K. G . GÖTZ, Tübingen F . F . SEELIG, Tübingen G . GOTTSCHALK, Göttingen J . SEELIG, Basel H . HOFFMANN-BERLING, Heidelberg H . SIMON, München R. JAENICKE, Regensburg W. STEGLICH, Bonn G . F . M E Y E R , Tübingen A. TREBST, Bochum M. RAJEWSKY, Essen

EDITED IN COLLABORATION

WITH T H E INSTITUTES OF T H E MAX-PLANCK-GESELLSCHAFT

V O L U M E 36c N U M B E R 7/8 J U L Y / A U G U S T 1981

V E R L A G D E R Z E I T S C H R I F T F Ü R N A T U R F O R S C H U N G

T Ü B I N G E N

Nachdruck — auch auszugsweise — nur mit schriftlicher Genehmigung des Verlages gestattet

Verantwortlich für den Inhalt: A . K L E M M

Satz und Druck: Konrad Triltsch, W ü r z b u r g

Volume 36c Zeitschrift für Naturforschung 1981

Subject Index

Original Communications and Notes

Absorption Pressure, Temperature and pH Dependence of the Absorption Spectrum of Reduced Nicotin-amide Adenine Dinucleotide 84 Chromophore Content and Molar Absorptivity of Phytochrome in the P r Form 431

Acacetin The Para-O-Methylation of Apigenin to Aca­cetin by Cell-Free Extracts of R o b i n i a pseudo-acacia L 916

Accessory Sex Gland On the Specificity of Juvenile Hormone Bio­synthesis in the Male Cecropia Moth 579

3-Acetyl-3-devinylchlorophyllide a Chlorophyll Biosynthesis: Various Chlorophyl­lides as Exogenous Substrates for Chlorophyll Synthetase 51

Acety lcholi neste rase Molecular Forms of Purified Cytoplasmatic and Membrane Bound Bovine-Brain-Acetylcholin-esterase Solubilized by Different Methods . . . 968

8-O - Ace ty lmioporosid Iridoids in Clerodendrum thomsonae Balf. f., Ver-benaceae . 708

Acridone Alkaloid Rutacridone-epoxide, a New Acridone Alkaloid from Ruta graveolens 200

Actin Cytochalasin B-Induced ATPase Activity of Ac­tin: Dependence on Monomer Concentration . 1050

Actin Polymerization Cytochalasin B-Induced ATPase Activity of Ac­tin: Dependence on Monomer concentration . 1050

Activation Volume The Pressure Dependence of the Rotation of the N-Aralkylpyridinium Moiety in a Synthetic NAD+ Model System Studied by High Pressure HRNMR 366

Active Particles Which Polypeptides Are Characteristic for Photosystem il? Analysis of Active Photo­system II Particles from the Blue-Green Alga Anacystis nidulans 295

Acyl-CoA Lipid Labelling in Intact Chloroplasts from Ex­ogenous Nucleotide Precursors 62

Co2+-Acylamino Acid, Amido Hydrolase Studies on the Z n 2 + / C o 2 + Exchange with Acyl-amino Acid Amidohydrolase from Pig Kidney . 951

Adenosine 3'-phosphate I n Vitro Biosynthesis of the Plant Sulpholipid: On the Origin of the Sulphonate Group . . . . 820

Adenostoma f a s c i c u l a t u m Analysis of Phenolic Acids by High Performance Liquid Chromatography Using a Step-Wise Gradient 357

Adenylylation Regulatory Properties of Glutamine Synthetase from the Nitroeen-Fixing Phototrophic Bacteri-um Rhodopseuäomonaspalustris 784

Adenylylation/Deadenylylation I n v i v o Control of Glutamine Synthetase in the Facultative Phototrophic Bacterium Rhodo-pseudomonas sphaeroiaes 407

A g a r i c u s Cadmium as a Growth Factor for the Mushroom A g a r i c u s abruptibulbus (Peck) Kauffmann . . . 765

Agmatine Ureo: Hydrolase Location of Several Enzymes of L-Arginine Ca-tabolism in E v e r n i a p r u n a s t r i Thallus (N) . . . 692

Ajuga Iridoids in Some Teucrium and A j u g a Species . 697

Alanine: Aldehyde Aminotransferase Properties and Subcellular Localization of L-Ala-nine: Aldehyde Aminotransferase: Concept of an Ubiquitous Plant Enzyme Involved in Sec-ondary Metabolism 625

Algae Comparative Binding of Photosystem II - Herbi-cides to Isolated Thylakoid Membranes and In­tact Green Algae 1041

Alkylating N AD-Analogs Half-of-the-Sites Reactivity of Glyceraldehyde-3-phosphate Dehydrogenase from Rabbit Mus-cle with Structural Analogs of NAD 545

Allosteric Interaction Direct Allosteric Interaction of Oxygen and Bi-carbonate: N-Acetyl-alany 1-seryl-phenylalanine, N-Terminal Sequence of the ß-Chains of the Haemoglobins of Nil Crocodile (Crocodylus niloticus) and Mississippi Crocodile {Alligator mississippiensis) (N) 902

A Iternaria cineraria a^-Dehydrocurvularin and Curvularin from A l ­ternaria cinerariae (N) 1081

Amine-Biosynthesis Properties and Subcellular Localization of L-Ala-nine: Aldehyde Aminotransferase: Concept of an Ubiquitous Plant Enzyme Involved in Sec-ondary Metabolism 625

Amino Acid Analysis Chemical Analysis and Structure of Poliovirus. I. Cysteine/Cystine Content, Complete Amino Acid Analysis and Hydrophobicity of Poliovirus and Its Naturally Occurring Empty Capsids . . 164

Amino Acid Transformation Radiation Damage to Polypeptides and Proteins in the Solid State, IL Radiolysis of Poly-L-Glu-tamicAcid(N) 1091

5-Aminolevulinate Dehydratase An Evolutionary Tree Based on Monoclonal Antibody-Recognized Surface Features of a Plastid Enzyme (5-Aminolevulinate Dehydra­tase) 44

Aminomethylphosphonic Acids Synthesis and Biological Activity of Ami­nomethylphosphonic Acids Related to the Her-bicide Glyphosate 242

Ammonium Assimilation Molecular Characterization of Glutamine Syn-

1098 Subject Index

thetase from the Nitrogen-Fixing Phototro­phic Bacterium Rhodopseuäomonas p a l u s t r i s . . 246

c-AMP Gaschromatographic, Mass- and Infrared-Spec-trometric Identification of Cyclic Adenosme-3': 5-monophosphate (c-AMP) in Maize Seed-lings (Zea mays) 193

Amphibia Are Yolk Phosvitins Carriers for Specific Cations? Comparative Microanalysis in Ver-tebrate Yolk Platelets (N) 686

A nacystis Which Polypeptides Are Characteristic for Pho­tosystem II? Analysis of Active Photosystem II Particles from the Blue-Green Alga Anacystis nidulans 295

A n d r e n a Pheromone Bouquet of the Mandibular Glands in A n d r e n a haemorrhoa F. (Hym.t Apoidea) . . 928

A niba Flavonoid Glycosides and Pyrones in A n i b a Species (Lauraceae) 385

Anthocyanins The Corolation of Gladiolus. I. Survey of Antho­cyanins in Petals of Gladiolus 378 Genetic Control of Chalcone Synthase Activity in Flowers of Matthiola incana R. Br 619 Anthocyanin Carrying Structures in Specific Genotypes of Matthiola incana R. Br 925

Anthocyanin Biosynthesis Genetic Control of Flavanone 3-Hydroxylase Activity and Flavonoid 3'-Hydroxylase Activity in A n t i r r h i n u m majus (Snapdragon) 411

A-5-MeC Antibody The Isolation of Antibodies Specific for 5-Me-thyl-Cytidine-Bovine Serum Albumin . . . . 459

Antibody Quantitation The Isolation of Antibodies Specific for 5-Me-thyl-Cytidine-Bovine Serum Albumin . . . . 459

Antifungals The Effect of Clotrimazole and Triadimefon on 3-Hydroxy-3-methyl-glutaryl-CoA-reductase-[EC 1.1.1.34]Äctivity in Saccharomyces cerevisiae 798

Rh Antigens Different Protein-Lipid Interaction in Human Red Blood Cell Membrane of Rh Positive and Rh Negative Blood Compared with Rh n un . . 988

Antimicrobial Activity Rutacridone-epoxide, a New Acridone Alkaloid from Ruta graveolens 200

Antimycotics The Effect of Clotrimazole and Triadimefon on 3-Hydroxy-3-methyl-glutaryl-CoA-reductase-[EC 1.1.1.34]Äctivity in Saccharomyces cerevisiae 798

A n t i r r h i n u m majus Genetic Control of Flavanone 3-Hydroxylase Activity and Flavonoid 3'-Hydroxylase Activity in A n t i r r h i n u m majus (Snapdragon) 411 Oxidation of Flavanones to Flavones with Flow-er Extracts of A n t i r r h i n u m majus (Snapdragon) 737

Antiserum Specificity Immunoadsorption as a Means for the Purifi-cation of Low Molecular Weight Compounds: Isolation of Ecdysteroids from Insects . . . . 790

Apigenin Oxidation of Flavones to Flavones with Flower Extracts o f A n t i r r h i n u m majus (Snapdragon) . . 737

Apo-Enzyme Studies on the Z n 2 + / C o 2 + Exchange with Acryl-amino Acid Amidohydrolase from Pig Kidney . 951

Arginase Location of Several Enzymes of L-Arginine (Catabolism) in E v e r n i a p r u n a s t r i Thallus. (N) . 692

Arrhenius Plots Arrhenius Plots Indicate Localization of Photo-synthetic and Respiratory Electron Transport in Different Membrane Regions of Anabaena . . 1036

A r t e m i s i a a b s i n t h i u m On the Essential Oil Components from A r t e m i s i a absint h i u m L 369

A r t e m i s i a dracunculus On the Composition of the Essential Oil from A r t e m i s i a dracunculus L. during the Vegetation Period 724

A r um maculatum Properties and Subcellular Localization of L-Ala-nine: Aldehyde Aminotransferase: Concept of an Ubiquitous Plant Ezyme Involved in Second-ary Metabolism 625

Asclepiadaceae Investigations on Hoya species. VIII. Leaf Flavonols and Di-C-glycosylflavones (N) . . . 1084

Ascomycetes Volatile Terpenes from Ceratocystis fimbriata (N) 1075

Ascorbic Acid ESR Investigations on Blood Treated Intraven-ously with Ascorbic Acid 1 Paramagnetic Changes in Pulmonary Tumors 5 On a Possible Mechanism of Action of Interferon 323 Ascorbate Oxidase and Its Possible Involvement in Cancer 804 Is there an Equilibrium between Ascorbic and Dehydroascorbic Acids? (N) 1088

Aspergillus oryzae Co+2-Substituted Acylamino Acid Amido Hy­drolase from Aspergillus oryzae 751

1 4 C - and 15N-Assimilation Photosynthetic Assimilation of 15N-Ammonia and 15N-Nitrate in the Marine Diatoms Bel­let-ochea yucatanensis (von Stosch) and Ske-letonema costatum 834

Assimilatory Nitrate Reductase Electron Transport to Assimilatory Nitrate Re­ductase in Azotobacter vinelandii 1030

ATP Synthesis A i r Synthesis and Generation of Electrochemi-cal Gradients of Protons in the Catecholamine Storage Organelle of the Adrenal Medulla . . 1056

ATPases 180-Exchanee by Hydrolyzing Enzymes: Exten­sion of the Model to P, Molecules with Inequi-valent Oxygen Atoms in the Bound State . . . 539

Atrazine Trypsin-Mediated Removal of Herbicide Bind-ing Sites within the Photosystem II Complex . . 98

Attractant A Sex Attractant for Sperchia intractana Walker (Lepidoptera: Tortricidae) in New Zealand (N) . 178

Audiospectrographic Study An Audiospectrographic Study of Male Stridu-lation in the Genus Corixa Geoffr. (Hemiptera, Corixidae) (N) 189

Auxin Properties of an ATP-Fueled, Cl"-Dependent Proton Pump Localized in Membranes of Microsomal Vesicles from Maize Coleoptiles . 997

Subject Index 1099

A v e n a Coleoptiles Initial Phases of Growth Induced by Sterylglu-cosides and Indole-3-acetic Acid in A v e n a Coleoptiles (N) 900

A vena sativa Application of Liquid Chromatography to a Study on 4-Coumarate: Coenzyme A Ligase Ac­tivity 199 Incorporation of [14C]Phenylalanine and [14C] Cinnamic Acid into Leaf Pieces and Mesophyll Protoplasts from Oat Primary Leaves for Studies on Flavonoid Metabolism at the Tissue and Cell Level 222 Preparation and Properties of Chromopeptides from the Pf rForm of Phytochrome 440 High Performace Liquid Chromatographie Ana­lysis of Steroidal Saponins from A v e n a sativa L. (N) 1072

Azadirachta indica Inhibition of Oogenesis and Ovarian Ecdysteroid Synthesis by Azadirachtin in Locusta migratoria migratorioides (R. & F.) 466

Azadirachtin Inhibition of Oogenesis and Ovarian Ecdysteroid Synthesis by Azadirachtin in Locusta migratoria migratorioides (R. & F.) 466

A z o t o b a c t e r vinelandii Electron Transport to Assimilatory Nitrate Re-duetase in A z o t o b a c t e r vinelandii 1030

Bacterial Constituents 7-Hydroxy Tropolone from Pseudomonas sp. (N) 728

Bacteriochlorophyllide a Chlorophyll Biosynthesis: Various Chloro­phyllides as Exogenous Substrates for Chloro­phyll Synthetase 51

Bacteriochlorophylls J2,10-Phytadienol as Esterifying Alcohol of Bacteriochlorophyll b from Ectothiorhodospira halochloris 417

Baker's Yeast Inhibition by Cyclic Guanosine 3': 5'-Mono-phosphate of the Soluble DNA Polymerase Ac­tivity, and of Partially Purified DNA Poly­merase A (DNA Polymerase I) from the Yeast Saccharomyces cerevisiae 813

Behavioral Mutant Drosophila Males Produce a Pheromone which Inhibits Courtship 694

Benzimidazole Nucleosides Solution Conformation of Benzimidazole Nu­cleosides with the Aid of Model Analogues . . 126

Bicarbonate Direct Allosteric Interaction of Oxygen and Bi­carbonate: N-Acetyl-alanyl-seryl-phenylalanine, N-Terminal Sequence of the ß-Chains of the Haemoglobins of Ni l Crocodile (Crocodylus niloticus) and Mississippi Crocodile (Alligator mississippiensis) (N) 902

Bilayer X-Ray Studies on Phospholipid Bilayers. I. Poly­morphie Forms of Dimyristoyl Lecithin . . . . 875

Biochemistry Binding of Polylysine and Ethidium Bromide to Nucleosomal DNA: Comparison of Biochemical and Electron Microscopical Results 149

3-Biosides Anthocyanin Carrying Structures in Specific Genotypes of Matthiola incana R. Br 925

Biosynthesis Purification of Chalcone Synthase from Tulip Anthers and Comparison with the Synthase from Cosmos Petals 30 Formation of Fusaric Acid by Fungi of the Genus Fusarium (N) 338 Structure and Biosynthesis of Vitexin 2"-0-Xylo-side in Silene alba 484 Methylation of 3',4' Di-OH C-Glycosylflavones in Silene 486 Conversion of Flavanone to Flavone, Dihy-droflavonol and Flavonol with an Enzyme Sys­tem from Cell Cultures ofParsley 742 The Püfra-O-Methylation of Apigenin to Aca cetin by Cell-Free Extracts ofRobiniapseudoaca-c i a h . 916 Biosynthesis of 3-Carboxy-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline and l-Methyl-3-carboxy-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline in a Callus Culture of Stizolobium hassjoo . . . . 1921

Blood Vascular System Vascular Specialization in Fish, but No Evidence for Lymphatics (N) 490

Blepharisma japonicum Synthesis of Blepharismone, the Low-Molecular Conjugation Hormone of Blepharisma japonicum

Blepharismone Synthesis of Blepharismone, the Low-Molecular Coniueation Hormone of Blepharisma japonicum (N) 180

Blood Count ESR Investigations on Blood Treated In-travenously with Ascorbic Acid 1

Blue-Green Algae Temperature Induced Changes in the Ab­sorption Spectra of Porphyridium cruentum and A naeystis nidulans 1013 Arrhenius Plots Indicate Localization of Photo-synthetic and Respiratory Electron Transport in Different Membrane Regions ofAnabaena . . 1036

Boletales Metabolites of 1,2,4-Trihydroxybenzene from Fruiting Bodies of Gomphiaius maculatus and G. glutinosus (Boletales) (N) 488

Bony Fishes Vascular Specialization in Fish, but No Evidence for Lymphatics 490

Bovine-Brain Molecular Forms of Purified Cytoplasmatic and Membrane Bound Bovine-Brain-Acetylcholin-esterase Solubilized by Different Methods . . . 968

Bovine Satellite DNAs A Family of Sequences with Regional Homology to Bovine 1.715 Satellite DNA 973

Brassicaceae Anthocyanin Carrying Structures in Specific Genotypes of Matthiola incana R. Br 925

Brown Algae C4-Metabolism in Marine Brown Macrophytic Algae 840

Burley Tobacco New Cembranoids from Burley Tobacco (N) . 1077

Cadmium Cadmium as a Growth Factor for the Mushroom A g a r i c u s abruptibulbus (Peck) Kauffmann . . . 765

1100 Subject Index

Calcium Effect of Isobutylmethylxanthine and Related Drugs on the Receptor Response (ERG; a-Wave) of the Frog Retina at Various Ex-tracellular Calcium Concentrations 597

Calf Thymus DNA Physico-Chemical Characteristics of DNA Chro­matin Fractions from Calf Thymus 361

Calf Thymus Freezing Lymphocyte Chalone from Calf Thymus: Prob­lems of Large Scale Extraction and Assay . . . 568

Callus Culture Biosynthesis of 3-Carboxy-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline and l-Methyl-3-carboxy-6,7 -dinydroxy-1,2,3,4- tetrahydroisoquinoline m a Callus Culture of Stizolobium hassjoo . . . . 921

Cancer On a Possible Mechanism of Action of Interferon 323

Cap Analogs Preparation of 5/,5//-Phosphate linked Dinu-cleosides 135

Carbohydrate Moiety Three Dimensional Structure of the Carbo­hydrate Moiety of a Lipopolysaccharide. Com­puter Calculations 71

Carbohydrates Discrimination of Two Fusogenic Properties of Aqueous Polyethylene Glycol Solutions . . . . 593

3-Carboxy-6,7-dihydroxy-1,2,3,4-tetrahydroiso­quinoline Biosynthesis of 3-Carboxy-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline and l-Methyl-3-carboxy-6,7-dinydroxy-1,2,3,4- tetrahydroisoquinoline m a Callus Culture of Stizolobium hassjoo . . . . 921

ß-Carboxylation C4-Metabolism in Marine Brown Macrophytic Algae 840

[14C]0-Carotene Carotenoids in the Stick Insect, Ectatosoma ti-aratum Isolation of ß,£-Caroten-2-ol and ß,e-Coroten-2-one 755

Carotenoids Effect of Vanadate and Iron Stress on the Pig­ment Composition of Chlorella Fusca 207 Partition of Phyllochinone K x between Digi-tonin Particles and Chlorophyll-Proteins of Chloroplast Membranes from Nicotiana tabacum 276

Caryophyllaceae Structure and Biosynthesis of Vitexin 2"-0-Xylo-side in Silene alba 484 Methylation of 3',4' Di-OH C-Glycosylflavones in Silene 486

Catecholamine Storage Organelles ATP Synthesis and Generation of Electrochemi-cal Gradients of Protons in the Catecholamine Storage Organelle of the Adrenal Medulla . . 1056

Catharanthus roseus Medium-Induced Formation of Indole Alkaloids and Concomitant Changes of Interrelated En­zyme Activities in Cell Suspension Cultures of Catharanthus roseus 40

Cations Are Yolk Phosvitins Carriers for Specific Cations? Comparative Microanalysis in Ver-tebrate Yolk Platelets 686

Cell Damage Titration of Rat Liver with Digitonin: a Well Defined Short Term Damage of Cellular Metab­olism 880

Cell Cultures Conversion of Flavanone to Flavone, Dihy-droflavonol and Flavonol with an Enzyme Sys­tem from Cell Cultures of Parsley 742

Cell Fusion Discrimination of Two Fusogenic Properties of Aqueous Polyethylene Glycol Solutions . . . . 593

Cell Membrane Rotation of Cells in an Alternating Electric Field: the Occurrence of a Resonance Frequency 173

Cell Rotation Rotation of Cells in an Alternating Electric Field: the Occurrence of a Resonance Frequency 173

Cembranoids New Cembranoids from Burley Tobacco (N) . 1077

Central Nervous System Action Potentials in "Non-Spiking" Visual In­terneurones 470

Ceratocystis ßmbriata Volatile Terpenes from Ceratocystis ßmbriata (N) 1075

C-Glycosylflavones Incorporation of [14C]Phenylalanine and [14C] Cinnamic Acid into Leaf Pieces and Meso­phyll Protoplasts from Oat Primary Leaves for Studies on Flavonoid Metabolism at the Tissue and Cell Level 222

Chalcone Synthase Purification of Chalcone Synthase from Tulip Anthers and Comparison with the Synthase from Cosmos Petals 30 Genetic Control of Chalcone Synthase Activity in Flowers of Matthiola incana R. Br 619

Change in Absorption Temperature Induced Changes in the Ab­sorption Spectra of Porphyridium cruentum and A nacystis nidulans 1013

Changes in Amino Acid Compositions Radiation Damage to Polypeptides and Proteins in the Solid State: Changes in Amino Acid Composition 310

Cr-Channel Properties of an ATP-Fueled, Cl"-Dependent Proton Pump Localized in Membranes of Microsomal Vesicles from Maize Coleoptiles 997

Chasing Courtship-Like Tracking Behaviour in Wild-Type Female Drosophila melanogaster . . . . 475

Chelating Ligands Studies on the Z n 2 + / C o 2 + Exchange with Acyl-amino Acid Amidohydrolase from Pig Kidney . 951

Chemosystematics Flavonoidglycoside and Pyrone bei Aniba-Arten (Lauraceae) 385

Chemotaxis Receptor Specifity and Threshold Concentration in Chemotaxis of the Phaeophyte Cutleria m u l t i -

fida 262 Chemotaxonomy

Iridoids in Some Teucrium and Ajuga Species . 697 Investigations on Hoya species. VIII. Leaf Flavonols and Di-C-glycosylflavones (N) . . . 1084

Chlamydomonas reinhardii CW 15 In Vitro Biosynthesis of the Plant Sulpholipid: On the Origin of the Sulphonate Group . . . . 820

Chlorella A Thioredoxin Activated Glutamine Synthetase in Chlorella 396

Subject Index 1101

Chlorella fusca Effect of Vanadate and Iron Stress on the Pig­ment Composition of Chlorella Fusca 207

4-Chloroaniline Incorporation of Chlorinated Anilines into Lig-nin 714

Chlorophyll Esterincation of Chlorophyllide in Prolamellar Body (PLB) and Prothylakoid (PT) Fractions from A vena sativa Etioplasts 58 Effect of Vanadate and Iron Stress on the Pig­ment Composition of Chlorella Fusca 207 Effect of Hydrogen Ion Concentration on the Absorption Spectrum and Fluorescence Life Time of Chloroplasts 638

Chlorphyll a/b Ratio Partition of Phyllochinone K! between Digi-tonin Particles and Chlorophyll-Proteins of Chloroplast Membranes from Nicotiana tabacum 276 Light-Induced Accumulation and Stability of Chlorophylls and Chlorophyll-Proteins during Chloroplast Development in Radish Seedlings . 421

Chlorophyll Degradation Light-Induced Accumulation and Stability of Chlorophylls and Chlorophyll-Proteins during Chloroplast Development in Radish Seedlings . 421 Pyropheophytin a Accompanies Pheophytin a in Darkenea Light Grown Cells ofEuglena . . . 827

Chlorophyll Fluorescence The Inhibition of Photosynthetic Light Reactions by Halogenated Naphthoquinones 645

Chlorophyll-Proteins Partition of Phylloquinone K x between Digi-tonin Particles and Chlorophyll-Proteins of Chloroplast Membranes from Nicotiana tabacum 276 Light-lnduced Accumulation and Stability of Chlorophylls and Chlorophyll-Proteins during Chloroplast Development in Radish Seedlings . 421

Chlorophyllides a and b Chlorophyll Biosynthesis: Various Chlorophyl­lides as Exogenous Substrates for Chlorophyll Synthetase 51

Chloroplast Development Light-Induced Accumulation and Stability of Chlorophylls and Chlorophyll-Proteins during Chloroplast Development in Radish Seedlings . 421

Chloroplast Envelope The Permeabiuty Coefficients of the Plas­malemma and the Chloroplast Envelope of Spin­ach Mesophyll Cells for Phytohormones . . . 672

Chloroplast Membranes Trypsin-Mediated Removal of Herbicide Bind-ing Sides within the Photosystem II Complex . 98

Chloroplasts Reinvestigation of the Effects of Disali-cylidenepropanediamine (DSPD) and 2-Heptyl-4-hydroxyquinoline-N-oxide (HQNO) on Pho­tosynthetic Electron Transport 109 Effect of Hydrogen Ion Concentration on the Absorption Spectrum and Fluorescence Life Time of Chloroplasts 638 Subcellular Compartmentation of Indole-3-ace-tic Acid in Mesopnyll Cells of Spinacia oleracea . 679 Evidence for a Transcarboxylase Reaction in Maize Chloroplast Extracts (N) 688 Effects of Linolenic Acid on the Spectral Proper­ties and Picosecond Fluorescence of Pea Chloro­plasts 1021

Chromatin Physico-Chemical Characteristics of DNA Chro­matin Fractions from Calf Thymus 361

Chrysosplenium americanum Polymethylated Flavonols of Chrysosplenium americanum. I. Identification and Enzymatic Synthesis 730

Cineraria aß-Dehydrocurvularin and Curvularin from A l ­ternaria cinerariae (N) 1081

Cinnamoyl Putrescines Effects of Glyphosate on Shikimic Acid Ac­cumulation in Tobacco Cell Cultures with Low and High Yields of Cinnamoyl Putrescines . . 210

Circadian Rhythm Effect of Lithium Chloride on the Circadian Rhythm in the Flight Activity of the Micro-chiropteran Bat, Tapnozous melanopogon . . . 1068

Circular Dichroism Protamines. VII. Circular Dichroism Study of Salmine A I 305 Effect of Hydrogen Ion Concentration on the Absorption Spectrum and Fluorescence Life Time of Chloroplasts 638

Clerodendrum Iridoids in Clerodendrum thomsonae Balf. f., Ver-benaceae 708

C4-Metabolism C4-Metabolism in Marine Brown Macrophytic Algae 840

C-Methylated Flavones Epicuticular Leaf Flavonoids from Eucalyptus Species and from Kalmia latifolia 913

Coa/Coß-Isomerism COa/Coß-Isomerism of the Cobalt Methylated Corrinoids. CD and ORD Spectra of Several Isomer Pairs 497

Cobyric Acid About the Iron Analogues of Cobalamin and Cobyric Acid 9

Coenzyme Derivatives Interactions between Tryptophan Synthase from Escherichia coli and Derivatives of the Coen­zyme Pyridoxal 5'-Phosphate 778

Coleoptile Properties of an ATP-Fueled, Cl~-Dependent Proton Pump Localized in Membranes of Microsomal Vesicles from Maize Coleoptiles . . 997 A H + / C a 2 + Antiporter in Membranes of Micro­somal Vesicles from Maize Coleoptiles, a Sec-ondary Energized C a 2 + Pump 1009

Collagen Fitting of SAXS-Curves by Nonlinear Regressi­on 333

Colony Assay Lymphocyte Chalone from Calf Thymus: Prob­lems of Large Scale Extraction and Assay . . . 568

Compartmental Analysis Subcellular Compartmentation of Indole-3-ace-tic Acid in Mesopnyll Cells of Spinacia oleracea 679

Computer Programs A Program Package for the Analysis of Peptide Conformations on the TR 440 (N) 347

Concentrations Effect of Oxygen on Photosynthetic C 0 2 Fix­ation of Synechococcus 93

Conformation Analysis Solution Conformation of Benzimidazole Nu-cleosides with the Aid of Model Analogues . . 126

1102 Subject Index

Coniferyl Alcohol Incorporation of Chlorinated Anilines into Lig-nin 714

Conjugation Synthesis of Blepharismone, the Low-Molecular Conjugation Hormone of Blepharisma japonicum .. 180

Continuous 1 4 C 0 2 Evolution I n vivo Evidence for a Functional Glycolytic Compartment in Synchronous Yeast Cells . . . 615

Contrast A Simple Coding Procedure Enhances a Neurones Information Capacity (N) 910

Copper and Spin Concentration of Blood ESR Investigations on Blood Treated In-travenously with Ascorbic Acid 1

Copper Proteins Ascorbate Oxidase and Its Possible Involvement in Cancer 804

Corixa An Audiospectrographic Study of Male Stridu-lation in the Genus Corixa Geoffr. (Hemiptera, Corixidae) (N) 189

Corpus allatum On the Specificity of Juvenile Hormone Bio­synthesis in the Male Cecropia Moth 579

Cosmos Purification of Chalcone Synthase from Tulip Anthers and Comparison with the Synthase from Cosmos Petals 30

/7-Coumaroyl-CoA Application of Liquid Chromatography to a Study on 4-Coumarate: Coenzyme A Ligase Ac­tivity 197

Courtship Courtship-Like Tracking Behaviour in Wild-Type Female Drosophila melanogaster . . . . 475

Cray fish es Isolation of Nuclei from Cray fish Tissues and Demonstration of Nuclear Ecdysteroid Re-ceptors 326

Cross-Linking Reassociation of Lactic Dehydrogenase from Pig Heart Studied by Cross-Linking with Glu-taraldehyde 772

Cryopreservation Lymphocyte Chalone from Calf Thymus: Prob­lems of Large Scale Extraction and Assay . . . 568

Crystal Packing Forces Influence of Crystal Packing Forces on Molecu­lar Structure in 4-Thiouricfine. Comparison of anti and syn Forms 956

Crystals Anthocyanin Carrying Structures in Specific Genotypes of Matthiola incana R. Br 925

Cruciferae Enzymatic Preparation and Properties of Some Desulfoglucosinolates 16

Cultures Effect of Glucocorticoids, Insulin and a Growth Promoting Tripeptide on the Biosynthesis of Plasma Proteins in Serum-Free Hepatocyte Cul­tures (N) 350

Curvularin aß-Dehydrocurvularin and Curvularin from A l ­ternaria cinerariae (N) 1081

Cutleria multiflda Receptor Specifity and Threshold Concentration in Chemotaxis of the Phaeophyte Cutleria m u l t i ­

flda 262

Cyanobacteria Hydrogen Evolution Catalyzed by Hydrogenase in Cultures of Cyanobacteria 87

Cyclic AMP-Dependent and -Independent Protein Kinases in HeLa Cells and in Human Cervix Carcinoma 552

Cyclic Guanosine Monophosphate Inhibition by Cyclic Guanosine 3'^'-Mono­phosphate of the Soluble DNA Polymerase Ac­tivity, and of Partially Purified DNA Polymerase A (DNA Polymerase I) from the Yeast Saccharo­myces cerevisiae 813

Cyclostomes Are Yolk Phosvitins Carriers for Specific Cations? Comparative Microanalysis in Verte-brate Yolk Platelets (N) 686

Cytochalasin B Cytochalasin B-Induced ATPase Activity of Ac­tin: Dependence on Monomer Concentration . 1050

Cytoplasm Intracellular Effect of Hydroxyalkenals on Ani-mal Tumors 572

Cytoplasmatic Molecular Forms of Purified Cytoplasmatic and Membrane Bound Bovine-Brain-Acetylcholin-esterase Solubilized by Different Methods . . . 968

Dark Fixation C4-Metabolism in Marine Brown Macrophytic Algae 840

DEAE The Isolation of Antibodies Specific for 5-Methyl-Cytidine-Bovine Serum Albumin . . 459

Dehydroascorbic Acid Is there an Equilibrium between Ascorbic and Dehydroascorbic Acids? (N) 1088

a^-Dehydrocurvularin aß-Öehydrocurvularin and Curvularin from A l-ternaria cinerariae (N) . 1081

Dehydrogenases Pressure, Temperature and pH Dependence of the Absorption Spectrum or Reduced Nicotin-amide Adenine Dinucleotide 84

Desulfo-Glucosinolates Enzymatic Preparation and Properties of Some Desulfoglucosinolates 16

Diacylsulphoquinovosyl Glyceride I n Vitro Biosynthesis of the Plant Sulpholipid: On the Origin of the Sulphonate Group . . . . 820

Digitonin Titration of Rat Liver with Digitonin: a Well Defined Short Term Damage of Cellular Metab­olism 880

A-Dihydrobilindiones Chromophore Content and Molar Absorptivity of Phytochrome in the P r Form 431

Dihydrocoumarin Dryopterin, ein neuartiges C17-Flavan aus Dryopteris filix-mas 607

Dimethylallyl Transferase Induction of Phytoalexin Synthesis in Soybean. Structure and Reactions of Naturally Occurring and Enzymatically Prepared Prenylated Ptero-carpans from Elicitor-Treated Cotyledons and Cell Cultures of Soybean 234

Dimyristoyl Lecithin X-Ray Studies on Phospholipid Bilayers. I. Poly­morphie Forms of Dimyristoyl Lecithin . . . . 875

Subject Index 1103

Dioxygenases Conversion of Flavanone to Flavone, Dihy-droflavonol and Flavonol with an Enzyme Sys­tem from Cell Cultures of Parsley 742

Diphenylether Mode of Inhibition of Photosynthetic Electron Transport by Substituted Diphenylethers . . . 848

Dipole Rotation of Cells in an Alternating Electric Field: the Occurrence of a Resonance Frequency 173

Diptera Action Potentials in "Non-Spiking" Visual In­terneurones 470

C o 2 + Dissociation Constant Studies on the Z n 2 + / C o 2 + Exchange with Acyl-amino Acid Aminohydrolase from Pig Kidney . 951

Diterpenoid Alcohols JzJO-Phytadienol as Esterifying Alcohol of Bac-teriochlorophyll b from Ectothiorhodospira halo-chloris 417

Diterpenoids New Cembranoids from Burley Tobacco (N) . . 1077

Diuron Trypsin-Medkted Removal of Herbicide Bind-ing Sites within the Photosystem II Complex . . 98

DNA Circular Permutation Partial Denaturation Mapping of Phage T4 DNA at Low Temperature 980

DNA Content DNA Content and Fraementation of the Egg Nucleus of Trichoplax adhaerens 564

DNA Denaturation Map Partial Denaturation Mapping of Phage T4 DNA at Low Temperature 980

DNA Polymerase I Inhibition by Cyclic Guanosine 3': 5'-Mono-phosphate of the Soluble DNA Polymerase Ac­tivity, and of Partially Purified DNA Poly­merase A (DNA Polymerasel) from the Yeast Saccharomyces cerevisiae 813

DNA Polymerase A Inhibition by Cyclic Guanosine 3':5'-Mono-phosphate of the Soluble DNA Polymerase Ac­tivity, and of Partially Purified DNA Poly­merase A (DNA Polymerase I) from the Yeast Saccharomyces cerevisiae 813

DNA Polymerase Activity Inhibition by Cyclic Guanosine 3':5'-Mono-phosphate of the Soluble DNA Polymerase Ac­tivity, and of Partially Purified DNA Poly­merase A (DNA Polymerase I) from the Yeast Saccharomyces cerevisiae 813

Drosophila melanogaster Courtship-Like Tracking Behaviour in Wild-Type Female Drosophila melanogaster . . . . 475 Drosophila Males Produce a Pheromone which Inhibits Courtship (N) 694

Dryopterisßlix-mas (L.) Schott Dryopterin, a Novel C17-Flavan from Dryopteris

ßlix-mas 607 Dye-Ligand Chromatography

Molecular Characterization of Glutamine Syn­thetase from the Nitrogen-Fixing Phototrophic Bacterium Rhodopseudomonas p a l u s t r i s . . . . 246

Ecdysteroids Inhibition of Oogenesis and Ovarian Ecdysteroid Synthesis by Azadirachtin in Locusta migratoria migratorioides (R. & F.) 466

Immunoadsorption as a Means for the Purifi­cation Low Molecular Weight Compounds: Iso­lation of Ecdysteroids from Insects 790

Effect of Oxygen and C 0 2 Concentrations Effect of Oxyeen on Photosynthetic C 0 2 Fix­ation of Synechococcus 93

Effects of Hydrogen Peroxide Electrophoretic and Chemical Studies on the X-Ray Damage of Malate Synthase 516

Egg Nucleus DNA Content and Fraementation of the Egg Nucleus of Trichoplax adhaerens 564

Fatty Acid Composition of Eggs durine De­velopment of the Cotton Leaf-Worm, Spoaoptera littoralis Boisduval 562

Ehrlich Ascites Tumor Cells The Effect of Glucosone on the Proliferation and Energy Metabolism of i n vitro Grown Ehrlich Ascites Tumor Cells 255

Electric Field Rotation of Cells in an Alternating Electric Field: the Occurrence of a Resonance Frequency 173

Electron Acceptors Site of Action of 2,5-Dimethoxy-3,6-Dichloro-/?-Benzoquinone in the Photosynthetic Electron Transport Chain 656

Electron Microscopy Radiation Damage to Polypeptides and Proteins in the Solid State: Changes in Amino Acid Composition 310 Isolation and Morphological Characterization of the Potato LefroU Virus (PLRV) 884 Radiation Damage to Polypeptides and Proteins in the Solid State, II. Radiolysis of Poly-L-Glu-tamicAcid(N) 1091

Electron Transport Reinvestigation of the Effects of Disali-cylidenepropanediamine (DSPD) and 2-Heptyl-4-hydroxyquinoline-N-oxide (HQNO) on Photo­synthetic Electron Transport 109 The Inhibition of Photosynthetic Light Reactions by Halogenated Naphthoquinones 645

Electron Transport to Nitrate Reductase Electron Transport to Assimilatory Nitrate Re­ductase in Azotobacter vinelandii 1030

Electroreceptors Electroreceptors and Direction Specific Arrange­ment in the Lateral Line System of Salaman­ders? (N) 493

Electroretinogram Effect of Isobutylmethylxanthine and Related Drugs on the Receptor Response (ERG; a-Wave) of the Frog Retina at Various Ex-tracellular Calcium Concentrations 597

Embryotoxicity Thalidomide-Like Malformations Caused by a Tween Surfactant in Mice 904

Empty Capsids Chemical Analysis and Structure of Polio virus. I. Cysteine/Cystine Content, Complete Amino Acid Analysis and Hydrophobicity of Poliovirus and Its Naturally Occurring Empty Capsids . . 164

Endothelial Cells Vascular Specialization in Fish, but No Evidence for Lymphatics (N) 490

1104 Subject Index

Energy Calculations A Program Package for the Analysis of Peptide Conformations on the TR440 (N) 347

Energy Metabolism The Effect of Glucosone on the Proliferation and Energy Metabolism of in vitro Grown Ehrlich Ascites Tumor Cells 255

Energy-Transfer Inhibition of ATP Synthesis Multifunctional Mode of Action of Substituted Nitrodiphenylethers in Scenedesmus Cells . . . 633

Enzymatic Synthesis Polymethylated Flavonols of Chrysosplenium americanum I. Identification and Enzymatic Syn­thesis 730

Enzyme Kinetics "O-Exchange by Hydrolyzing Enzymes: An ab initio Calculation 534 180-Exchange by Hydrolyzing Enzymes: Exten­sion of the Model to P, Molecules with Inequi-valent Oxygen Atoms in the Bound State . . . 539

Enzyme Mecnanism "O-Exchange by Hydrolyzing Enzymes: Exten­sion of the Model to P, Molecules with Inequi-valent Oxygen Atoms in the Bound State . . . 539

Enzyme Purification Purification and Properties of a New Enzyme from Evernia p r u n a s t r i , which Reduces L-Usnic Acid 35

Envelope Lipid Labelling in Intact Chloroplasts from Ex-ogenous Nucleotide Precursors 62

Envelope Polypeptides Purification of Murine and Feline Type-C Virus Envelope Polypeptides as Micellar Protein Com-plexes (N) 353

Epidermis Distribution of Phenylalanine Ammonia-Lyase and 4-Coumarate: CoA Ligase in Oat Primary LeafTissues 389

Erythrocyte Immobilization of Erythrocytes by Radiation Po-lymerization of Glass-Forming Monomers at Low Temperatures 1062

ESR ESR Investigations on Blood Treated In-travenously with Ascorbic Acid 1 Paramagnetic Changes in Pulmonary Tumors . 5 Ascorbate Oxidase and Its Possible Involvement in Cancer 804 On a Possible Mechanism of Action of Interferon 323 Altered Herne Environments in Opossum and Rabbit Methemoglobins 964 Is there an Equiübrium between Ascorbic and Dehydroascorbic Acids? (N) 1088

ESR and Infrared Studies Different Protein-Lipid Interaction in Human Red Blood Cell Membrane of Rh Positive and Rh Negative Blood Compared with Rh n uu . . 988

ESR Spectroscopy Interaction of Phloretin with the Human Red Cell Membrane and Membrane Lipids: Evi­dence from Infrared, Raman and ESR Spec­troscopy 586

Essential Oil On the Essential Oil Components from Majorana hortensis Moench 23 On the Essential Oil Components from A r t e m i s i a a b s i n t h i u m L 369

On the Composition of the Essential Oil from A r t e m i s i a drancunculus L. during the Vegetation Period 724

Ethane Production Stimulation of Wound Reactions in Potato Tubers by Thiabendazole 115

Ethidium Bromide Binding of Polylysine and Ethidium Bromide to Nucleosomal DNA: Comparison of Biochemical and Electron Microscopical Results 149

Etioplast Red Light Induced Change in the Saponin Con­tent of Prolamellar Bodies in A vena sativa . . . 869 High Performance Liquid Chromatographie Analysis of Steroidal Saponins from A vena sativa L. (N) 1072

Eucalyptus globulus Epicuticular Leaf Flavonoids from Eucalyptus Species and from Kalmia latifolia 913

Euglena Pyropheophytin a Accompanies Pheophytin a in Darkened Light Grown Cells of Euglena . . . 827

Evernia p r u n a s t r i Purification and Properties of a New Enzyme from Evernia p r u n a s t r i , which Reduces L-Usnic Acid 35 Location of Several Enzymes of L-Arginine Ca-tabolism in Evernia p r u n a s t r i Thallus. (N) . . . 692

Evolutionary Tree An Evolutionary Tree Based on Monoclonal Antibody-Recognized Surface Features of a Plastid Enzyme (5-Aminolevulinate Dehydra-tase) 44

Exchange ATP Synthesis and Generation of Electrochemi-cal Gradients of Protons in the Catecholamine Storage Organelle of the Adrenal Medulla . . 1056

180-Exchange 180-Excnange by Hydrolyzing Enzymes: An ab initio Calculation 534 180-Exchange by Hydrolyzing Enzymes: Exten­sion of the Model to P, Molecules with Inequi-valent Oxygen Atoms in the Bound State . . . 539

Z n + 2 / C o + 2 Exchange Co+2-Substituted Acylamino Acid Amido Hy­drolase from Aspergillus oryzae 751

Externa! Flavonoid Aglycones Epicuticular Leaf Flavonoids from Eucalyptus Species and from Kalmia latifolia 913

Extinction Coefficient Chemical Analysis and Structure of Poliovirus. I. Cysteine/Cystine Content, Complete Amino Acid Analysis and Hydrophobicity of Poliovirus and Its Naturally Occurring Empty Capsids . . 164

Facultative Phototrophic Bacteria I n Vivo Control of Glutamine Synthetase in the Facultative Phototrophic Bacterium Rho-dopseudomonas sphaeroides 407

Farinose Exudate Unusual Flavanones from a Rare American Fern 604

Fatty Acids Fatty Acid Composition of Eggs during De­velopment of the Cotton Leaf-Worm, Spoaoptera littoralis Boisduval 562

Subject Index 1105

Fe(III)Cobalamin About the Iron Analogues of Cobalamin and Cobyric Acid

Females Courtship-Like Tracking Behaviour in Wild-Type Female Drosophila melanogaster . . . .

9(11)-Fernene 9(11)-Fernene and Its 21-Epimer as an Epi­cuticular Layer on Ferns (N)

Ferredoxin Electron Transport to Assimilatory Nitrate Re-ductase in Azotobacter vinelandii

Ferulic Acid Esters Ferulic Acid-Sucrose Esters from Immature Anthers of Tulipa cv. "Apeldoorn"

Fibronectin Effect of Lectins and Chemical Modification on the Hemagglutinin Activity of Human Plasma Fibronectin

1 4 C 0 2 Fixation Effect of Oxygen on Photosynthetic C 0 2 Fix­ation of Synecnococcus

Flavan Dryopterin, ein neuartiges C17-Flavan aus Dryopteris filix-mas

Flavanone Genetic Control of Flavanone 3-Hydroxylase Activity and Flavonoid 3'-Hydroxylase Activity in A n t i r r h i n u m majus (Snapdragon)

Flavanone Oxidase Oxidation of Flavanones to Flavones with Flow-er Extracts of A n t i r r h i n u m majus (Snapdragon) .

Flavins Isolation and Identification of an Oxygen Re-ducing Factor (ORF) from Isolated Spinach Chloroplast Lamellae

Flavodoxin Electron Transport to Assimilatory Nitrate Re-ductase in Azotobacter vinelandii

Flavonoid Biosynthesis Oxidation of Flavanones to Flavones with Flow-er Extracts of A n t i r r h i n u m majus (Snapdragon) .

Flavonoid 3'-Hydroxylase Genetic Control of Flavanone 3-Hydroxylase Activity and Flavonoid 3'-Hydroxylase Activity in A n t i r r h i n u m majus (Snapdragon)

Flavonoids Purification of Chalcone Synthase from Tulip Anthers and Comparison with the Synthase from Cosmos Petals Flavonoid Glycosides and Pyrones in A n i b a -Species (Lauraceae) Genetic Control of Flavanone 3-Hydroxylase Activity and Flavonoid 3-Hydroxylase Activity in A ntirrhinum majus (Snapdragon) Genetic Control of Chalcone Synthase Activity in Flowers of Matthiola incana R. Br Conversion of Flavanone to Flavone, Dihy-droflavonol and Flavonol with an Enzyme Sys­tem from Cell Cultures of Parsley The Para-O-Methylation of Apigenin to Aca-cetin by Cell-Free Extracts of Robinia pseudoa-cacia L . . .

Flavonol Investigations on Hoya species. VIII. Leaf Fla-vonols and Di-C-glycosyltlavones (N) . . . .

Flight Activity Effect of Lithium Chloride on the Circadian

9 Rhythm in the Flight Activity of the Micro-chiropteran Bat, Tapnozous melanopogon . . . 1068

Fluorescence Lifetimes 475 Effect of Hydrogen Ion Concentration on the

Absorption Spectrum and Fluorescence Life Time of Chloroplasts 638

896 Effects of Linolenic Acid on the Spectral Proper­ties and Picosecond Fluorescence of Pea Chloro­plasts 1021

1030 FlyEye A Simple Coding Procedure Enhances a Neurones Information Capacity (N) 910

721 a-Formylphenylacetic Acid Chemical Synthesis of a-Formylphenylacetic Acid, the Postulated Precursor of Tropic Acid . 611

Fraementation o6-, DNA Content and Fraementation of the Egg

Nucleus of Trichoplax adhaerens 564 Free Radical

Is there an Equilibrium between Ascorbic and 9 3 Dehydroascorbic Acids? (N) 1088

Frog Retina Effect of Isobutylmethylxanthine and Related

607 Drugs on the Receptor Response (ERG; a-Wave) of the Frog Retina at Various Ex-tracellular Calcium Concentrations 597

Fusaric Acid 411 Formation of Fusaric Acid by Fungi of the

Genus Fusarium (N) 338 Fusarium

7 r 7 Formation of Fusaric Acid by Fungi of the / J / Genus Fusarium (N) 338

Fusogenic Properties Discrimination of Two Fusogenic Properties of

^ Aqueous Polyethylene Glycol Solutions . . . . 593

Gamones Synthesis of Blepharismone, the Low-Molecular

1030 Coniueation Hormone of Blepharisma japonicum (N) 180

GC-MS-Analysis 737 Gaschromatographic, Mass- and Infrared-Spec-

trometric Identification of Cyclic Adenosine-3':5'-monophosphate (c-AMP) in Maize Seed­lings (Zea mays) 193

4 1 1 Mammalian Pheromone Studies, IV. Terpenoid Compounds and Hydroxy Esters from the Dor­sal Gland of the Springbok, Antidorcas mar-supialis(N) 340 Mammalian Pheromone Studies, V. Compounds

3 0 from the Preorbital Gland of the Grysbok, Raphicerus melanotis (N) 344

3 8 5 GC-MS Data On the Essential Oil Components from Majorana hortensis Moench 23

411 On the Essential Oil Components from A rtemisia absinthium L 369

619 Gel Preparation An lmproved Method for the Preparation of the Four Ribonucleic Acids of Cowpea Chlorotic

742 Mottle Virus 157 Genetic Control

Genetic Control of Chalcone Synthase Activity 916 in Flowers of Matthiola incana R. Br 619

Gibberella Formation of Fusaric Acid by Fungi of the

1084 Genus Fusarium (N) 338

1106 Subject Index

Gladiolus The Coloration of Gladiolus I. Survey of Antho-cyanins in Petals of Gladiolus 378

Glass-Forming Monomer Immobilization of Erythrocytes by Radiation Po-Wmerization of Glass-Forming Monomers at Low Temperatures 1062

Glucagon Immunoreactivity Glucagon-Like Immunoreactivity (GLI) in Blood Plasma of Partially Hepatectomized Rats . 464

Glucagon-Like Immunoreactivity (GLI) Glucagon-Like Immunoreactivity (GLI) in Blaod Plasma of Partially Hepatectomized Rats . 464

Glucocorticoids Effect of Glucocorticoids, Insulin and a Growth Promoting Tripeptide on the Biosynthesis of Plasma Proteins in Serum-Free Hepatocyte Cul­tures (N) 350

2-^-D-Glucopyranosyloxy-2S-butyronitrile The Cyanogenic Glycoside of Holcus mollis (N) . 336

Glucosinolate Sulfohydrolase Enzymatic Preparation and Properties of Some Desulfoglucosinolates 16

Glucosinolates Enzymatic Preparation and Properties of Some Desulfoglucosinolates 16

Glucosone The Effect of Glucosone on the Proüferation and Energy Metabolism of in vitro Grown Ehrlich Ascites Tumor Cells 255

Glutamine A Thioredoxin Activated Glutamine Synthetase in Chlorella 396

Glutamine Synthetase Molecular Characterization of Glutamine Syn­thetase from the Nitrogen-Fixing Phototrophic Bacterium Rhodospseudomonas palustris . . . 246 I n Vivo Control of Glutamine Synthetase in the Facultative Phototrophic Bacterium Rhodo-pseudomonas sphaeroiaes 407

Glutamine Synthetase Regulation Regulatory Properties of Glutamine Synthetase from the Nitrogen-Fixing Phototrophic Bacteri­um Rhodopseuäomonas palustris 784

Glutaraldehyde Reassociation of Lactic Dehydrogenase from Pig Heart Studied by Cross-Linking with Glu­taraldehyde 772

Glyceraldehyde-3-phosphate Dehydrogenase Half-of-the-Sites Reactivity of Glyceraldehyde-3 phosphate Dehydrogenase from Rabbit Muscle with Structural Analogs of NAD 545

Glycine max L. Induction of Phytoalexin Synthesis in Soybean. Structure and Reactions of Naturally Occurring and Enzymatically Prepared Prenylated Ptero-carpans from Elicitor-Treated Cotyledons and Cell Cultures of Soybean 234

Glycolytic Compartment I n vivo Evidence for a Functional Glycolytic Compartment in Synchronous Yeast Cells . . . 615

Di-C-glycosylflavone Investigations on Hoya species. VIII. Leaf Flavonols and Di-C-glycosylflavones (N) . . . 1084

Glyphosate Effects of Clyphosate on Shikimic Acid Accumu­lation in Tobacco Cell Cultures with Low and High Yields of Cinnamoyl Putrescines . . . . 210

Glyphosate Analogues Synthesis and Biological Activity of Amino-methylphosphonic Acids Related to the Herbi-cide Glyphosate 242

Gomphidius Metabolites of 1,2,4-Trihydroxybenzene from Fruiting Bodies of Gomphidius maculatus and G. glutinosus (Boletales) [ 1 ] 488

Gomphilactone Metabolites of 1,2,4-Trihydroxybenzene from Fruiting Bodies of Gomphidius maculatus and G. glutinosus (Boletales) [1] 488

Graded Signal Transmission Action Potentials in "Non-Spiking" Visual In­terneurones 470

Growth Initial Phase of Growth Induced by SteryIglu­cosides "and Indole-3-acetic Acid in Avena Coleoptiles 900

H+-ATPase Properties of an ATP-Fueled, Cl -Dependent Proton Pump Localized in Membranes of Microsomal Vesicles from Maize Coleoptiles . 997 A H + / C a 2 + Antiporter in Membranes of Microsomal Vesicles from Maize Coleoptiles, a Secondary Energized C a 2 + Pump 1009

Haemoglobin Direct Allosteric Interaction of Oxygen and Bi-carbonate: N-Acetyl-alanyl-sery 1-phenylalanine, N-Terminal Sequence of the ß-Chains of the Haemoglobins of Nil Crocodile (Crocodylus niloticus) and Mississippi Crocodile (Alligator mississippiensis) (N) 902

Half-of-the-Sites Reactivity Half-of-the Sites Reactivity of Glyceraldehyde-3 phosphate Dehydrogenase from Rabbit Muscle with Structural Analogs of NAD 545

Halophilic Bacteria J2,10-Phytadienol as Esterifying Alcohol of Bac-teriochlorophyll b from Ectothiorhodospira halochloris 417

HeLa Cells Protein Kinases in HeLa Cells and in Human Cervix Carcinoma 552

a-Helix Protamines. VII. Circular Dichroism Study of Salmine A I 305

Hemagglutination Effect of Lectins and Chemical Modification on the Hemagglutinin Activity of Human Plasma Fibronectin 863

Herne Environment Altered Herne Environments in Opossum and Rabbit Methemoglobins 964

Herbicide Binding Comparative Binding of Photosystem II - Herbi-cides to Isolated Thylakoid Membranes and In-tact Green Algae 1041

Herbicides Synthesis and Biological Activity of Aminomethylphosphonic Acids Related to the Herbicide Glyphosate 242 Multifunctional Mode of Action of Substituted Nitrodiphenylethers in Scenedesmus Cells . . . 633 Mode of Inhibition of Photosynthetic Electron Transport by Substituted Diphenylethers . . . 848

Subject Index 1107

Two Sites of Inhibition of the Photosynthetic Electron Transport Chain by the Herbicide Tri-fluralin Comparative Binding of Photosystem II - Herbi-cides to Isolated Thylakoid Membranes and In-tact Green Algae

Heterocysts Hydrogen Evolution Catalyzed by Hydrogenase in Cultures of Cyanobacteria

(S)-Heterodendrin The Cyanogenic Glycoside of Holcus mollis (N)

5,5'-Hexahydroxybiphenyl Metabolites of 1,2,4-Trihydroxybenzene from Fruiting Bodies of Gomphidius maculatus and G. glutinosus (Boletales) [1]

Hign Mobiiity Group Proteins Preferential Phosphorylation of Hieh Mobility Group Protein 17 in vitro by a Nuclear Protein Kinase

High Performance Chromatography Pyropheophytin a Accompanies Pheophytin a in Darkened Light Grown Cells of Euglena . . .

High Performance Liquid Chromatography Formation of Fusaric Acid by Fungi of the Genus Fusarium (N) Analysis of Phenolic Acids by High Performance Liquid Chromatography Using a Step-Wise Gradient The Coloration of Gladiolus. I. Survey of Antho-cyanins in Petals of Gladiolus High Performance Liquid Chromatographie Anal­ysis of Steroidal Saponins from A vena sativa L.

High Pressure Pressure, Temperature and pH Dependence of the Absorption Spectrum of Reduced Nicotina-mide Adenine Dinucleotide The Pressure Dependence of the Rotation of the N-Aralkylpyridinium Moiety in a Synthetic NAD 4" Model System Studied by High Pressure HRNMR

Higher Plant Lipids In Vitro Biosynthesis of the Plant Sulpholipid: On the Origin of the Sulphonate Group . . . .

HMG-CoA-Reductase The Effect of Clotrimazole and Triadimefon on 3-Hydroxy-3-Methyl-Glutaryl-CoA-Reductase-[EC 1.1.1.34]Activity in Saccharomyces cerevisiae

Holcus The Cyanogenic Glucoside of Holcus mollis (N) .

Homeostasis Effect of Lithium Chloride on the Circadian Rhythm in the Flieht Activity of the Micro-chiropteran Bat, Tapnozous melanopogon . . .

Hormones Synthesis of Blepharismone, the Low-Molecular Conjugation Hormone of Blepharisma japonicum (N)

Hoya Investigations on Hoya species. VIII. Leaf Flavonols and Di-C-glycosylflavones (N) . . .

Human Cervix Carcinoma Protein Kinases in HeLa Cells and in Human Cervix Carcinoma

Human Thymus Steroids Steroids of Human Thymi (N)

Hyalophora cecropia On the Specificity of Juvenile Hormone Bio­synthesis in the Male Cecropia Moth

Hydrogen Bonds Aspartic Acid-Aspartate and Glutamic Acid-

853 Glutamate Hydrogen Bonds Having Great Pro­ton Polarizability - IR Investigations 961

Hydrogen Evolution 1041 Hydrogen Evolution Catalyzed by Hydrogenase

in Cultures of Cyanobacteria 87 Hydrogen Exchange

87 Hydrogen-Deuterium Exchange in Adenosine 5'-Monqphosphate Detected by Surface En-

336 hanced Raman Scatterin (SERS) 809 Hydrogen Metabolism

Hydrogen Evolution Catalyzed by Hydrogenase in Cultures of Cyanobacteria 87

488 Hydrogenase Hydrogen Evolution Catalyzed by Hydrogenase in Cultures of Cyanobacteria 87

Hydrophobicity 319 Chemical Analysis and Structure of Poliovirus. I.

Cysteine/Cystine Content, Complete Amino Acids Analysis and Hydrophobicity of Poliovirus

827 and Its Naturally Occurring Empty Capsids . . 164 2-Hydroxy-carotenoids

Carotenoids in the Stick Insect, Ectatosoma ti-338 aratum Isolation of ß,£-Caroten-2-ol and ß,e-

Caroten-2-one 755 llß-Hydroxy-4-pregnene-3,20-dione

357 Steroids of Human Thymi (N) 1086 7-Hydroxy Tropolone

378 7-Hydroxy Tropolone from Pseudomonas sp. [1] . 728 7/3-Hydroxycholesterol

1072 Steroids of Human Thymi (N) 1086 Hydroxycinnamic Acid Conjugates

Ferulic Acid-Sucrose Esters from Immature Anthers of Tulipa cv. "Apeldoorn" 721

84 Hypochroism Preparation of 5',5"-Phosphate Linked Dinu-cleosides 135

366 Icosahedron

070 Isolation and Morphological Characterization of the Potato Leafroll Virus (PLRV) . . . . . . 884

Identification Polymethylated Flavonols of Chrysosplenium

790 americanum I. Identification and Enzymatic Syn­thesis 730

336 Identified Neurones Action Potentials in "Non-Spiking" Visual In­terneurones 470

Immunoadsorption of Steroids 106g Immunoadsorption as a Means for the Purifi­

cation of Low Molecular Weight Compounds: Isolation of Ecdysteroids from Insects . . . . 790

Immunobilization jgO Immobilization of Ery throey tes by Radiation Po-

lymerization of Glass-Forming Monomers at Low Temperatures 1062

IQg4 Immunodiffusion The Isolation of Antibodies Specific for 5-Methyl-Cytidine-Bovine Serum Albumin . . 459

Impermeability 5 5 2 Lipid Labelling in Intact Chloroplasts from Ex-

ogenous Nucleotide Precursors 62 1086 Individual CCMV RNAs

An Improved Method for the Preparation of the Four Ribonucleic Acids of Cowpea Chlorotic

579 Mottle Virus 157

1108 Subject Index

Indole-3-acetic Acid Initial Phases of Growth Induced by Sterylglu-cosides and Indole-3-acetic Acid in Avena Coleoptiles (N) Subcellular Compartmentation of Indole-3- acetic Acid in Mesophyll Cells of Spinacia oleracea

Indole Alkaloids Medium-Induced Formation of Indole Alkaloids and Concomitant Changes of Interrelated En­zyme Activities in Cell Suspension Cultures of Catharanthus roseus

Information Theory A Simple Coding Procedure Enhances a Neuron's Information Capacity (N)

Infrared Raman Interaction of Phloretin with the Human Red Cell Membrane and Membrane Lipids: Evi­dence from Infrared, Raman and ESR Spec-troscony

Infrared-äpectrometry Gaschromatographic, Mass- and Infrared-Spec-trometric Identification of Cyclic Adenine-3 :5'-monophosphate (c-AMP) in Maize Seedlings (Zea mays)

Inhibition Two Sites of Inhibition of the Photosynthetic Electron Transport Chain by the Herbicide Tri-fluralin

Inhibitors Reinvestigation of the Effects of Disali-cylidenepropanediamine (DSPD) and 2-Heptyl-4- hydroxyquinoline-N-oxide (HQNO) on Photo­synthetic Electron Transport Inhibition of Photosynthetic Electron Transport by the Quinone Antagonist UHDBT Isolation and Partial Characterization of the Membrane-Bound NADH Dehydrogenase from the Photoptophic Bacterium Rhodopseudo-monas capsulata The Inhibition of Photosynthetic Light Reactions by Halogenated Naphthoquinones Drosophila Males rroduce a Pheromone which Inhibits Courtship (N) Mode of Inhibition of Photosynthetic Electron Transport by Substituted Diphenylethers . . .

Initiation Initiation of Protein Synthesis in Yeast: Binding ofMet-tRNAi

Initiator tRNA Initiation of Protein Synthesis in Yeast: Binding ofMet-tRNAi

Inositol Hexaphosphate Altered Herne Environments in Opossum and Rabbit Methemoglobins

Insect Pests Oviposition Deterrance Activity in Some Lami-aceae Plants against Some Insect Pests . . . .

Insulin Effect of Glucocorticoids, Insulin and a Growth Promoting Tripeptide on the Biosynthesis of Plasma Proteins in Serum-Free Hepatocyte Cul­tures (N)

Interferon On a Possible Mechanism of Action of Interferon

Iridaceae The Coloration of Gladiolus. I. Survey of Antho-cyanins in Petals of Gladiolus

Iridoids Iridoids in Some Teucrium and Ajuga Species . 697 Iridoids in Clerodendrum thomsonae Balf. f., Ver-

900 benaceae 708 Iron-Bi 2-Analogues

About the Iron Analogues of Cobalamin and 679 Cobyric Acid 9

Iron Stress Effect of Vanadate and Iron Stress on the Pig­ment Composition of Chlorella Fusca 207

Isobutylmethylxanthine 40 Effect of Isobutylmethylxanthine and Related

Drugs on the Receptors Response (ERG; a-Wave) of the Frog Retina at Various Ex-

910 tracellular Calcium Concentrations 597 Isophorcabilin

Chromophore Content and Molar Absorptivity of Phytochrome in the P rForm . . . . . . . 431

Isoscoparin 586 Methylation of 3',4' Di-OH C-Glycosylflavones

in Silene 486

JH Biosynthesis On the Specificity of Juvenile Hormone Bio-

*93 synthesis in the male Cecropia Moth 579

Kalanchoe bl. o«-̂ Succulence - Induction in Kalanchoe bloß-

feldiana under Long-Day Conditiones by a Lipo-phyle Fraction out of Flowering Kalanchoe and MS-Identification of Pterosterone 465

Kalmia latifolia JQQ Epicuticular Leaf Flavonoids from Eucalyptus

Species and from Kalmia latifolia 913 1 1 0 7-Keto-cholesterol z / z Steroids of Human Thymi (N) 1086

Kinetic Properties Co+2-Substituted Acylamino Acid Amido Hy-

4QQ drolase from Aspergillus oryzae 751 Kok Effect

6 4 5 The Kok Effect and Its Relationship to Photore­spiration in Tobacco 450

694 Lactic Dehydrogenase

848 Reassociation of Lactic Dehydrogenase from Pig Heart Studied by Cross-Linking with Glu-taraldehyde 772

142 Lactone Dryopterin, a Novel C17-Flavan from Dryopteris ßlix-mas 607

142 Lamiaceae Oviposition Deterrance Activity in Some Lami­aceae Plants against Some Insect Pests . . . . 122

964 Lateral Line Afferents Electroreceptors and Direction Specific Arrange­ment in the Lateral Line System of Salaman-

1 2 2 ders?(N) 493 Lateral Line Efferents

Electroreceptors and Direction Specific Arrange­ment in the Lateral Line System of Salaman­ders? (N) 493

- C A LeafWax 9(11)-Fernene and Its 21-Epimer as an Epi­cuticular Layer on Ferns (N) 896

323 Lectins Effect of Lectins and Chemical Modification on the Hemagglutinin Activity of Human Plasma

378 Fibronectin 863

Subject Index 1109

Leukemia Ascorbate Oxidase and Its Possible Involvement in Cancer 804

Leukemia L1210 Specific Positional Distribution of Acyl Moieties in Phospholipids is not Generally Deleted in Neoplastic Cells 81

L i +

Effect of Lithium Chloride on the Circadian Rhythm in the Flight Activity of the Micro-chiropteran Bat, Taphozous melanopogon . . . 1068

Liehen Substances Pannaric Acid and Prophyrilic Acid Methyl Ester Liehen Substances in the Genus Psoroma (N) 893

Life Cycle Life Cycle of Sarcocystis between Poikilothermie Hosts. Lizards are Intermediate Hosts for S. p o -darcicolubris sp. nov, Snakes Function as Defini­tive Hosts (N) 1093

Lifetimes Effects of Linolenic Acid on the Spectral Proper­ties and Picosecond Fluorescence of Pea Chloro­plasts 1021

Ligase Application of Liquid Chromatography to a Study on 4-Coumarate: Coenzyme A Ligase Ac­tivity 197

Lignin Incorporation of Chlorinated Anilines into Lig­nin 714

Liliaceae Ferulic Acid-Sucrose Esters from Immature Anthers of Tulipa cv. "Apeldoorn" 721

Liliopsida The Cyanogenic Glycoside of Holcus mollis (N) . 336

Linolenic Acid Effects of Linolenic Acid on the Spectral Proper­ties and Picosecond Fluorescence of Pea Chloro­plasts 1021

Lipid and Fatty Acid Composition Light-Dependent Changes in the Lipid and Fat­ty Acid Composition of Phycocyanin-Free Photosynthetic Lamellae of Synechococcus . . 856

Lipid Peroxidation Stimulation of Wound Reactions in Potato Tubers by Thiabendazole 115

Lipid Phase Transition Temperature Induced Changes in the Ab­sorption Spectra of Porphyridium cruentum and A naeystis nidulans 1013

Lipid Transition Temperature Different Protein Lipid Interaction in Human Red Blood Cell Membrane of Rh Positive and Rh Negative Blood Compared with Rh n un . . 988

Lipid Transport Lipid Labelling in Intact Chloroplasts from Ex-ogenous Nucleotide Precursors 62

Lipopolysaccharide Three Dimensional Structure of the Carbo-hydrate Moiety of a Lipopolysaccharide. Com­puter Calculations 71

Liver Perfusion Titration of Rat Liver with Digitonin: a Well Defined Short Term Damage of Cellular Metab­olism 880

Lizard Life Cycle of Sarcocystis between Poikilothermie Hosts. Lizards are Intermediate Hosts for S. p o -

darcicolubris sp. nov, Snakes Function as Defini­tive Hosts (N) 1093

Localization Isolation and Partial Characterization of the Membrane-Bound NADH Dehydrogenase from the Phototrophic Bacterium Rhodopseudomonas capsulata 400

Locusta migratoria Inhibition of Oogenesis and Ovarian Ecdysteroid Synthesis by Azadirachtin in Locusta migratoria migratorioides (R. & F.) 466

Long Spacing Eitting of SAXS-Curves by Nonünear Regres­sion 333

Low Temperature Immooilization of Erythrocytes by Radiation Po-lymerization of Glass-Forming Monomers at Low Temperatures 1062

Lung Cancer Ascorbate Oxidase and Its Possible Involvement in Cancer 804

Luteolin Oxidation of Flavanones to Flavones with Flow-er Extracts of A n t i r r h i n u m majus (Snapdragon) . 737

Lymphatics Vascular Specialization in Fish, but No Evidence for Lymphatics (N) 490

Lymphocyte Chalone Lymphocyte Chalone from Calf Thymus: Prob­lems of Large Scale Extraction and Assay . . . 568

Lymphocyte Responsiveness Lymphocyte Chalone from Calf Thymus: Prob­lems of Large Scale Extraction and Assay . . . 568

Maize Gaschromatographic, Mass- and Infrared-Spec-trometric Identification of Cyclic Adenosme-3': 5'-monophosphate (c-AMP) in Maize Seed­lings (Zea mays) 193

Majorana hortensis M. On the Essential Oil Components from Majorana hortensis Moench 23

Malate Synthase Electrophoretic and Chemical Studies on the X-Ray Damage of Malate Synthase 516

Mammalian Type-C Viruses Purification of Murine and Feline Type-C Virus Envelope Polypeptides as Micellar Protein Com-plexes (N) 353

Mandibular Glands Pheromone Bouquet of the Mandibular Glands in Andrena haemorrhoa F. (Hym., Apoidea) . . 928

Marine Diatoms Photosynthetic Assimilation of 15N-Ammonia and I5N-Nitrate in the Marine Diatoms Bei-lerochea yucatanensis (von Stosch) and Ske-letonema costatum 193

Mass-Spectrometry Gaschromatographic, Mass- and Infrared-Spec-trometric Identiiication of Cyclic Adenosine-3': 5/-monophosphate (c-AMP) in Maize Seed­lings (Zea mays) 834 The Kok Effect and Its Relationship to Photore­spiration in Tobacco 450 Dependence of Photorespiration and Photo­synthetic Unit Sizes on Two Interdependent Nu-clear Gene Factors in Tobacco 619 Iroids in Clerodendrum thomsonae Balf. f., Ver-benaceae 708

1110 Subject Index

Matthiola incana Genetic Control of Chalcone Synthase Activity in Flowers of Matthiola incana R. Br 662 Anthocyanin Carrying Structures in Specific Genotypes of Matthiola incana R. Br 925

Media Effects Medium-Induced Formation of Indole Alkaloids and Concomitant Changes of Interrelated En­zyme Activities in Cell Suspension Cultures of Catharanthus roseus 40

Membrane X-Ray Studies on Phospholipid Bilayers. I. Poly­morphie Forms of Dimyristoyl Lecithin . . . . 875

Membrane-Bound Molecular Forms of Purified Cytoplasmatic and Membrane Bound Bovine-Brain-Acetylcholin-esterase Solubilized by Different Methods . . . 968

Membrane Ghosts ATP Synthesis and Generation of Electrochemi-cal Gradients of Proton in the Catecholamine Storage Organelle of the Adrenal Medulla . . 1056

Membrane-Phioretin Interaction Interaction of Phloretin with the Human Red Cell Membrane and Membrane Lipids: Evi­dence from Infrared, Raman and ESR Spec-troscopy 586

Membrane Vesicles A H + / C a 2 + Antiporter in Membranes of Microsomal Vesicles from Maize Coleoptiles, a Secondary Energized C a 2 + Pump 1099

Mesophyll Protoplasts Distribution of Phenylalanine Ammonia-Lyase and 4-Coumarate: CoA Ligase in Oat Primary LeafTissues 389

Metablic Compartmentation Titration of Rat Liver with Digitonin: a Well Defined Short Term Damage of Cellular Metab­olism 880

Metabolism Carotenoids in the Stick Insect, Ectatosoma ti-aratum Isolation of ß,e-Caroten-2-ol and ß,e-Caroten- 2-one 755

C4-Metabolism C4-Metabolism in Marine Brown Macrophytic Algae 840

Methemoglobin Altered Herne Environments in Opossum and Rabbit Methemoglobins 964

1 -Methyl-3-carboxy-o,7-dihydroxy-1,2,3,4-tetra-hydroisoquinoline

Biosynthesis of 3-Carboxy-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline and l-Methyl-3-carboxy-6,7-dinydroxy-1,2,3,4-tetrahydroisoquinoline in a Callus Culture of Stizolobium hassjoo . . . . 921

Methyl Corrinoids Coa/Co/J-Isomerism of the Cobalt Methylated Corrinoids. CD and ORD Spectra of Several Isomer Pairs 497

Methylation Methylation of 3',4' Di-OH C-Glucosylflavones in Silene (N) 486

O-Methyltransferase Polymethylated Flavonols of Chrysosplenium americanum. I. Identification and Enzymatic Synthesis 730

Micellar Complexes Purification of Murine and Feline Type-C Virus Envelope Polypeptides as Micellar Protein Com­plexes (N) 353

Microbial Acylamino Acid Amido Hydrolase Co+2-Substituted Acylamino Acid Amido Hy­drolase from Aspergillus oryzae 751

Mode of Action The Effect of Clotrimazole and Triadimefon on 3-Hydroxy-3-Methyl-Glutaryl-CoA-Reductase-[EC 1.1.1.34]Activity in Saccharomyces cerevisiae 798

Model syn and anti Conformations Solution Conformation of Benzimidazole Nu-cleosides with the Aid of Model Analogues . . 126

Molecular Forms Molecular Forms of Purified Cytoplasmatic and Membrane Bound Bovine-Brain-Acetylcholin-esterase Solubilized by Different Methods . . . 968

Molecular Structures Influence of Crystal Packing Forces on Molecu­lar Structure in 4-Thiouridine. Comparison of anti and syn Forms 956

Monoclonal Antibodies An Evolutionary Tree Based on Monoclonal Antibody-Recognized Surface Features of a Plastid Enzyme (5-Aminolevulinate Dehydra-tase) 44

Monoterpenes Volatile Terpenes from Ceratocystis ßmbriata (N) 1075

Morphology Binding of Polylysine and Ethidium Bromide to Nucleosomal DNA: Comparison of Biochemical and Electron Microscopical Results 149

Mouse The Specific Labeling in Hypertonie Medium of a Spleen Protein (N) 183 Thalidomide-Like Malformations Caused by a Tween Surfactant in Mice (N) 904

Mushrooms Cadmium as a Growth Factor for the Mushroom Agricus abruptibulbus (Peck) Kauffmann . . . 765

Mycelium Cadmium as a Growth Factor for the Mushroom Agricus abruptibulbus (Peck) Kauffmann . . . 765

Myosin S1 180-Exchange by Hydrolyzing Enzymes: An ab initio Calculation 534

NAD +-Model The Pressure Dependence of the Rotation of the N-Aralkylpyridinium Moiety in a Synthetic NAD 4 - Model System Studied by High Pressure HRNMR 366

NADH Pressure, Temperature and pH Dependence of the Absorption Spectrum of Reduced Nicotina-mide Adenine Dinucleotide 84

N A D H Dehydrogenase Isolation and Partial Characterization of the Membrane-Bound NADH Dehydrogenase from the Phototrophic Bacterium Rhodopseuäomonas capsulata 400

15N-Labelled Amino Acids Photosynthetic Assimilation of 15N-Ammonia and 15N-Nitrate in the Marine Diatoms Bel-lerochea yucatanensis (von Stosch) and Ske-letonema costatum 834

Naphthoquinones The Inhibition of Photosynthetic Light Reactions by Halogenated Naphthoquinones 645

Subject Index 1111

Neural Coding A Simple Coding Procedure Enhances a Neuron s Information Capacity (N) 910

Neurosarcoma Specific Positional Distribution of Acyl Moieties in Phospholipids is not Generally Deleted in Neoplastic Cells 81

Nicotiana tabacum Effects of Glyphosate on Shikimic Acid Ac­cumulation in Tobacco Cell Cultures with Low and High Yields of Cinnamoyl Putrescines . . 210 New Cembranoids from Burley Tobacco (N) . 1077

N itrodiphenylethers Multifunctional Mode of Action of Substituted Nitrodiphenylethers in Scenedesmus Cells . . . 633

Nitrogen Fixation Molecular Characterization of Glutamine Syn­thetase from the Nitrogen-Fixing Phototrophic Bacterium Rhodopseuäomonas palustris . . . . 246

Nitrate Nitrate Photo-Assimilation by the Phototrophic Bacterium Rhodopseuäomonas capsulata ExFj . 1025

Nitrate Reductase Nitrate Photo-Assimilation by the Phototrophic Rhodopseuäomonas capsulata EiFi 1025

Nitrite Nitrate Photo-Assimilation by the Phototrophic Bacterium Rhodopseuäomonas capsulata E ^ . 1025

CNMR Data On the Essential Oil Components from Majorana hortensis Moench 23 On the Essential Oil Components from Artemisia absinthium L 369

3 1 P-NMR Preparation of 5',5"-Phosphate Linked Dinu-cleosides 135 löO-Exchange by Hydrolyzing Enzymes: An ab initio Calculation 534 180-Exchange by Hydrolyzing Enzymes: Exten­sion of the Model to P/ Molecules with Inequi-valent Oxygen Atoms in the Bound State . . . 539

NMR The Pressure Dependence of the Rotation of the N-Aralkylpyridinium Moiety in a Synthetic N A D + Model System Studied by High Pressure HRNMR 366 Iridoids in Clerodendrum thomsonae Balf., f., Verbenaceae 708

Nonionic Surfactant Tween 20 Thalidomide-Like Malformations Caused by a Tween Surfactant in Mice 904

Nonlinear Polarisationoscillations Nonlinear Polarisa tionoscillations in a Biophysi-cal Model-System I: Internal Dynamics . . . . 888

Notholaena fendleri Unusual Flavonones from a Rare American Fern 604

Novel Flavanone Unusual Flavanones from a Rare American Fern 604

Novel Flavonoid Epicuticular Leaf Flavonoids from Eucalyptus Species and from Kalmia latifolia 913

Nuclear and Cytoplasmic Kinase Preferential Pnosphorylation of High Mobility Group Protein 1/ in vitro by a Nuclear Protein Kinase 319

Nuclear Ecdysteroid Receptors Isolation of Nuclei from Crayfish Tissues and

Demonstration of Nuclear Ecdysteroid Re­ceptors 326

Nuclei Isolation of Nuclei from Crayfish Tissues and Demonstration of Nuclear Ecdysteroid Re­ceptors 326

Nucleic Acids Hydrogen-Deuterium Exchange in Adenosine 5'-Monophosphate Detected by Surface En-hanced Raman Scattering (SERS) 809

Nucleosomes Binding of Polylysine and Ethidium Bromide to Nucleosomal DNA: Comparison of Biochemical and Electron Microscopical Results 149

Nucleotidases 180-Exchange by Hydrolyzing Enzymes: An ab initio Calculation 534

Nucleus Intracellular Effect of Hydroxyalkenals on Ani-mal Tumors 572

Oat Leaf Development Distribution of Phenylalanine Ammonia-Lyase and 4-Coumarate: CoA Ligase in Oat Primary Leaf Tissues 389

Olfactory Communication Mammalian Pheromone Studies, IV. Terpenoid Compounds and Hydroxy Esters from the Dor­sal Gland of the Springbok, Antidorcas mar-supialis (N) 340 Mammalian Pheromone Studies, V. Compounds from the Preorbitai Gland of the Grysbok, Raphicerus melanotis (N) 344

Ovary Inhibition of Oogenesis and Ovarian Ecdysteroid Synthesis by Azadirachtin in Locusta migratoria migratorioides R. & F.) 466

Oviposition-Deterrance Oviposition Deterrance Activity in Some Lami-aceae Plants against Some Insect Pests . . . . 122

Oxidoreductases Pressure, Temperature and pH Dependence of the Absorption Spectrum or Reduced Nicotin-amide Adenine Dinucleotide 84

2-Oxo-carotenoids Carotenoids in the Stick Insect, Ectatosoma ti-aratum Isolation of /J,£-Caroten-2-ol and ß,e-Caroten- 2-one 755

Oxygen Direct Allosteric Interaction of Oxygen and Bi-carbonate: N-Acetyl-alanyl-seryl-phenylalanine, N-Terminal Sequence oi the ß-Chains of the Haemoglobins of Nil Crocodile (Crocoäylus niloticus) and Mississippi Crocodile (Alligator mississippiensis) (N) 902

Oxygen Activation Isolation and Identification of an Oxygen Re-ducing Factor (ORF) from Isolated Spinach Choloroplast Lamellae 284

Paeonia "Yellow Flavonols" as Components of Pollen Pigmentation 204

PAGE Electophoretic and Chemical Studies on the X-Ray Damage of Malate Synthase 516

1112 Subject Index

Pannaric Acid Pannaric Acid and Prophyrilic Acid Methyl Ester Liehen Substances in the Genus Psoroma (N) 893

Para-O-Methyltransferase The Para-0-Methylation of Apigenin to Acacetin by Cell-Free Extracts of Robinia pseudoacacia L 916

Partial Hepatectomy Glucagon-Like Immunoreactivity (GLI) in Blood Plasma of Partially Hepatectomized Rats 464

Pepsin Digestion Preparation and Properties of Chromopeptides from the P&Form ofPhytochrome 440

P f r Peptide Preparation and Properties of Chromopeptides from the PfrForm ofPhytochrome 440

Peptide Conformations A Program Package for the Analysis of Peptide Conformations on the TR 440 (N) 347

Peptide Maps Purification of Murine and Feline Type-C Virus Envelope Polypeptides as Micellar Protein Com-plexes (N) 353

Permeability Subcellular Compartmentation of Indole-3-acetic Acid in Mesophyll Cells of Spinacia oleracea 679

Permeability Coefficients The Permeability Coefficients of the Plas­malemma and the Chloroplast Envelope of Spin­ach Mesopyll Cells for Phytohormones . . . . 672

Peroxidase Incorporation of Chlorinated Anilines into Lig-nin 714

Petroselinum hortense Conversion of Flavanone to Flavone, Dihy-droflavonol and Flavonol with and Enzyme Sys­tem from Cell Cultures of Parsley 742

Phage T 4 Partial Denaturation Mapping of Phage T4 DNA at Low Temperature 980

Phase Transition Temperatures Arrhenius Plots Indicate Localization of Photo­synthetic and Respiratory Electron Transport in Different Membrane Regions ofAnabaena . . 1036

Phenolic Acids Analysis of Phenolic Acids by High Performance Liquid Chromatography Using a Step-Wise Gradient 357

Phenylmalonic Semialdehyde Chemical Synthesis of a-Formylphenylacetic Acid, the Postulated Precursor of Tropic Acid . 611

[14C]Phenylpropanoid Incorporation Incorporation of [14C]Phenylalanine and l 1 4C] Cinnamic Acid into Leaf Pieces and Mesophyll Protoplasts from Oat Primary Leaves for Studies on Flavonoid Metabolism at the Tissue and Cell Level 222

Phenylpropanoids Distribution of Phenylalanine Ammonia-Lyase and 4-Coumarate: CoA Ligase in Oat Primary Leaf Tissues 389 On the Composition of the Essential Oil from A r t e m i s i a dracunculus L. during the Vegetation Period 724

Pheromones Mammalian Pheromone Studies, IV. Perpenoid Compounds and Hydroxy Esters from the Dor­

sal Gland of the Springbok, Antidorcas mar-supialis (N) 340 Pheromone Bouquet of the Mandibular Glands in Andrena haemorrhoa F. (Hym., Apoidea) . . 928 Mammalian Pheromone Studies, V. Compounds from the Preorbital Gland of the Grysbok, Raphicerus melanotis 344

5',5"-Phosphate Bridged Dinucleosides Preparation of y,5"-Phosphate Linked Dinu­cleosides 135

Phosphatidylcholine Sinapine as a Supply of Choline for the Bio­synthesis of Phospnatidylcholine in Raphanus sativus Seedlings 215

Phosphoüpids Specific Positional Distribution of Acyl Moieties in Phospholipids is not Generally Deleted in Neoplastic Cells 81 Sinapine as a Supply of Choline for the Bio­synthesis of Phospnatidylcholine in Raphanus sativus Seedlings 215 X-Ray Studies on Phospholipid Bilayers I. Poly­morphie Forms of Dimyristoyl Lecithin . . . . 875

Phosphorylation Preferential Phosphorylation of High Mobility Group Protein 1/ in vitro by a Nuclear Protein Kinase 319

Phosvitin Are Yolk Phosvitins Carriers for Specific Cations? Comparative Microanalysis in Ver-tebrate Yolk Platelets 686

Photoassimilation Nitrate Photo-Assimilation by the Phototrophic Bacterium Rhodopseudomonas capsulata E 1 F 1 1025

Photorespiration Dependence of Photorespiration and Photo­synthetic Unit Sizes on Two Interdependent Nu­clear Gene Factors in Tobacco 662

Photosynthetic Bacteria J2,10-Phytadienol as Esterifying Alcohol of Bac-teriochlorophyll b from Ectothiorhodospira halochloris 417

Photosynthetic Electron Transport Inhibition of Photosynthetic Electron Transport by the Quinone Antagonist UHDBT 272 Isolation and Identification of an Oxygen Re-ducing Factor (ORF) from Isolated Spinach Choloroplast Lamellae 284 Two Sites of Inhibition of the Photosynthetic Electron Transport Chain by the Herbicide Tri-fluralin 853 Multifunctional Mode of Action of Substituted Nitrodiphenylethers in Scenedesmus Cells . . . 633

Photosynthetic Units Dependence of Photorespiration and Photo­synthetic Unit Sizes on Two Interdependent Nu­clear Gene Factors in Tobacco 662

Photosynthesis Trypsin-Mediated Removal of Herbicide Bind­ing Sites within the Photosystem II Complex . . 98 ^d2,10-Phytadienol as Esterifying Alcohol of Bac-teriochlorophyll b from Ectothiorhodospira halo­chloris 417 Effect of Hydrogen Ion Concentration on the Absorption Spectrum and Fluorescence Life Time of Chloroplasts 638 The Inhibition of Photosynthetic Light Reactions by Halogenated Naphthoquinones 645

Subject Index 1113

Evidence for a Transcarboxylase Reaction in Maize Chloroplast Extracts 688 Pyropheophytin a Accompanies Pheophytin a in Darkened Light Grown Cells of Euglena . . . 827 C4-Metabolism in Marine Brown Macrophytic Algae 840 Mode of Inhibition of Photosynthetic Electron Transport by Substituted Diphenylethers . . . 848 Temperature Induced Changes in the Ab­sorption Spectra of Porphyridium cruentum and Anacystis nidulans 1013 Effects of Linolenic Acid on the Spectral Proper­ties and Picosecond Fluorescence of Pea Chloro­plasts 1021 Arrhenius Plots Indicate Localization of Photo­synthetic and Respiratory Electron Transport in Different Membrane Regions of Anabaena . . 1036 Comparative Binding of Photosystem II - Herbi-cides to Isolated Thylakoid Membranes and In-tact Green Algae 1041

Photosystem II Which Polypeptides Are Characteristic for Photosystem II? Analysis of Active Photosystem II Particles from the Blue-Green Alga Anacystis nidulans 295 Site of Action of 2,5-Dimethoxy-3,6-Dichioro-o-Benzoquinone in the Photosynthetic Electron Transport Chain 656

Phototrophic Bacteria Molecular and Kinetic Characterization of Xan-thine Dehydrogenase from the Phototrophic Bacterium Rhodopseudomonas capsulata . . . 933

Phycobili Proteins Chromophore Content and Molar Absorptivity of Phytochrome in the P r Form 431 Temperature Induced Changes in the Ab­sorption Spectra of Phorphyridium cruentum and A nacystis nidulans 1013

Phycocyanin-Free Lamellae Light-Dependent Changes in the Lipid and Fatty Acid Composition of Phycocyanin-Free Photosynthetic Lamallae of Synechococcus . . 856

Phylloquinone Partition of Phylloquinone K t between Digi­tonin Particles and Chlorophyll-Proteins of Chloroplast Membranes from Nicotiana tabacum 276

Phyllospaaix scouleri Analysis of Phenolic Acids by High Performance Liquid Chromatography Using a Step-Wise Gradient 357

Physical-Chemical Data Enzymatic Preparation and Properties of Some Desulfoglucosinolates 16

Phytic Acid Biosynthesis Radioactively Labelled Phytic Acid from Matur-ing Seeds of Sinapis alba 383

Phytoalexins Induction of Phytoalexin Synthesis in Soybean. Structure and Reactions of Naturally Occurring and Enzymatically Prepared Prenylated Ptero-carpans from Elicitor-Treated Cotyledons and Cell Cultures of Soybean 234

Phytochrome Preparation and Properties of Chromopeptides from the P f r Form of Phytochrome 440

Phytochromobilin Peptide Preparation and Froperties of Chromopeptides from the PfrForm ofPhytochrome 440

Phytoflagellate Chlorogonium elongatum Regulation of the Synthesis of Ribulose-1,5-bisphosphate Carboxylase and Its Subunits in the Flagellate Chlorogonium elongatum. II. Coordinated Synthesis of the Large and Small Subunits 942

Phytohormones The Permeability Coefficients of the Plas­malemma and the Chloroplast Envelope of Spin­ach Mesophyll Cells for Phytohormones . . . 672

Pigment Bleaching Multifunctional Mode of Action of Substituted Nitrodiphenylethers in Scenedesmus Cells . . . 633

Pigment Composition Ultrastructure of Differently Pigmented Sy­nechococcus Cells (N) 907

Pigmentation "Yellow Flavonols" as Components of Pollen Pigmentation 204 Light-Dependent Changes in the Lipid and Fat­ty Acid Composition of Phycoyanin-Free Photo­synthetic Lamellae of Synechococcus 856

Planogyra formosana 9(11)-Fernene and Its 21-Epimer as an Epi­cuticular Layer on Ferns (N) 896

C 4 Plants Evidence for a Transcarboxylase Reaction in Maize Chloroplast Extracts (N) 688

Plasma Proteins Effect of Glucocorticoids, Insulin and a Growth Promoting Tripeptide on the Biosynthesis of Plasma Proteins in Serum-Free Hepatocyte Cul­tures (N) 350

Plasmalemma The Permeability Coefficients of the Plas­malemma and the Chloroplast Envelope of Spin­ach Mesophyll Cells for Pnytohormones . . . 672

Plastoquinone Mode of Inhibition of Photosynthetic Electron Transport by Substituted Diphenylethers . . . 848

Poaceae Application of Liquid Chromatography to a Study on 4-Coumarate: Coenzyme A Ligase Ac­tivity 197 The Cyanogenic Glycoside of Holcus mollis (N) 336

Poliovirus Chemical Analysis and Structure of Poliovirus. I. Cysteine/Cystine Content, Complete Amino Acid Analysis and Hydrophobicity of Poliovirus and Its Naturally Occurring Empty Capsids . . 164

Pollen "Yellow Flavonols" as Components of Pollen Pigmentation 204

Polyamide Column Chromatography Application of Liquid Chromatography to a Study on 4-Coumarate: Coenzyme A Ligase Ac­tivity 197

Polyethylene Glycol Discrimination of Two Fusogenic Properties of Aqueous Polyethylene Glycol Solutions . . . . 593

Polyhedral Bodies Ultrastructure of Differently Pigmented Sy­nechococcus Cells (N) 907

Polylysine binding of Polylysine and Ethidium Bromide to Nucleosomal DNA: Comparison of Biochemical and Electron Microscopical Results 149

Polymethylated Flavonols Polymethylated Flavonols of Chrysosplenium

1114 Subject Index

americanum. I. Identification and Enzymatic Synthesis 730

Polypeptides Which Polypeptides Are Characteristic for Photosystem II? Analysis of Active Photo­system II Particles from the Blue-Green Alga A nacystis nidulans 295

Polypodiaceae Unusual Flavanones from a Rare American Fern 604 Dryopterin, a Novel C17-Flavan from Dryopteris ßlix-mas 607 9(11)-Fernene and Its 21-Epimer as an Epi­cuticular Layer on Ferns (N) 896

Polypodium glaucinum 9(11)-Fernene and Its 21-Epimer as an Epi­cuticular Layer on Ferns (N) 896

Porphyrilic Acid Methyl Ester Pannaric Acid and Prophyrilic Acid Methyl Est­er Liehen Substances in the Genus Psoroma . . 893

Positional Distribution of Acyl Moieties Specific Positional Distribution of Acyl Moieties in Phospholipids is not Generally Deleted in Neoplastic Cells 81

Potato Virus Isolation and Morphological Characterization of the Potato Leafroll Virus (PLRV) 884

Precipitation Reaction Tne Isolation of Antibodies Specific for 5-Methyl-Cytidine-Bovine Serum Albumin . . 459

4-Pregnene-3,20-dione Steroids of Human Thymi (N) 1086

Primary Leaf Tissues Incorporation of [14C]Phenylalanine and [* 4C] Cinnamic Acid into Leaf Pieces and Mesophyll Protoplasts from Oat Primary Leaves for Studies on Flavonoid Metabolism at the Tissue and Cell Level 222

Prolamellar Bodies Esterification of Chlorophyllide in Prolamellar Body (PLB) and Prothylakoid (PT) Fractions from A vena sativa Etioplasts 58 Red Light Induced Change in the Saponin Con­tent of Prolammelar Bodies in A vena sativa . . 869

Proliferation The Effect of Glucosone on the Proliferation and Energy Metabolism of in vitro Grown Ehrlich Ascites Tumor Cells 255

Protamine Protamines. VII. Circular Dichroism Study of Salmine A I 305

Protection and Repair by Dithiothreitol Electophoretic and Chemical Studies on the X-Ray Damage of Malate Synthase 516

Protein The Specific Labeling in Hypertonie Medium of a Spleen Protein (N) 183

Protein Kinases Protein Kinases in HeLa Cells and in Human Cervix Carcinoma 552

Protein-Lipid Interaction Different Protein-Lipid Interaction in Human Red Blood Cell Membrane of Rh Positive and Rh Negative Blood Compared with Rh n un . . 988

Protein Molecules Aspartic Acid-Aspartate and Glutamic Acid-Glutamate Hydrogen Bonds Having Great Pro­ton Polarizability - IR Investigations 961

Protein Thiols Intracellular Effect of Hydroxyalkenals on Ani-mal Tumors 572

Protein Synthesis Initiation of Protein Synthesis in Yeast: Binding ofMet-tRNAi 142

Protochlorophyllide Chlorophyll Biosynthesis: Various Chloro­phyllides as Exogenous Substrates for Chloro­phyll Synthetase 51 Red Light Induced Change in the Saponin Con­tent of Prolamellar Bodies in A v e n a sative . . . 869

Proton Polarizability Aspartic Acid-Aspartate and Glutamic Acid-Glutamate Hydrogen Bonds Having Great Pro­ton Polarizability - IR Investigations 961

Proton Pump Properties of an ATP-Fueled, Cl"-Dependent Proton Pump Localized in Membranes of Microsomal Vesicles from Maize Coleoptiles . . 997

Protoplasts Incorporation of [14C]Phenylalanine and [* 4C]Cinnamic Acid into Leaf Pieces and Meso­phyll Protoplasts from Oat Primary Leaves for Studies on Flavonoid Metabolism at the Tissue and Cell Level 222

Pseudomonas sp. 7-Hydroxy Tropolone from Pseudomonas sp. [1] . 728

Psoroma Pannaric Acid and Prophyrilic Acid Methyl Est­er Liehen Substances in the Genus Psoroma (N). 893

Pterocarpans Induction of Phytoalexin Synthesis in Soybean. Structure and Reactions of Naturally Occurring and Enzymatically Prepared Prenylated Ptero­carpans from Elicitor-Treated Cotyledons and Cell Cultures of Soybean 234

Pterosterone Succulence - Induction in Kalanchoe bloß-

feldiana under Long-Day Conditiones by a Lipo-phyle Fraction out of Flowering Kalanchoe and MS-Identification of Pterosterone 465

Pulmonary Tumors Paramagnetic Changes in Pulmonary Tumors 5

Ca 2 + Pump AH + / ( Ja 2 + Anti porter in Membranes of Micro­somal Vesicles from Maize Coleoptiles, a Sec-ondary Energized C a 2 + Pump 1009

Purification Purification of Murine and Feline Type-C Virus Envelope Polypeptides as Micellar Protein Com-?>lexes 353 solation and Partial Characterization of the

Membrane-Bound N A D H Dehydrogenase from the Phototrophic Bacterium Rhodopseudomonas capsulata 400

Pyridoxal 5'-Phosphate Interactions between Tryptophan Synthase from Escherichia coli and Derivatives of the Coen­zyme Pyridoxal 5'-Phosphate 778

Primidine Tracts Physico-Chemical Characteristics of DNA Chro­matin Fractions from Calf Thymus 361

Pyrochlorophyllide a, Chlorophyll Biosynthesis: Various Chloro­phyllides as Exogenous Substrates for Chloro­phyll Synthase 51

Subject Index 1115

Pyrones Flavonoid Glycosides and Pyrones in A n i b a Species (Lauraceae) 385

Pyropheophytin Pyropneophytin a Accompanies Pheophytin a in Darkenea Light Grown Cells of E u g l e n a . . . 827

Pyruvate Metabolism I n vivo Evidence for a Functional Glycolytic Compartment in Synchronous Yeast Cells . . . 615

Quinone Inhibition of Photosynthetic Electron Transport by the Quinone Antagonist UHDBT 272

Quinones and Quinonediamines Site of Action of 2,5-Dimethoxy-3,6-Dichloro-/7-Benzoquinone in the Photosynthetic Electron Transport Chain 656

Radiation Damage Electrophoretic and Chemical Studies on the X-Ray Damage of Malate Synthase 516 Radiation Damage to Polypeptides and Proteins in the Solid State, II Radiolysis of Poly-L-Glu-tamic Acid (N) 1091

Radiation Damage to Proteins Radiation Damage to Polypeptides and Proteins in the Solid State: Changes in Amino Acid Composition 310

Radiation Polymerization Immobilization of Ery throcy tes by Radiation Po­lymerization of Glass-Forming Monomers at Low Temperatures 1062

Raphanus Sinapine as a Supply of Choline for the Bio­synthesis of Phospnatidylcholine in Raphanus sativus Seedlings 215

Rat Titration of Rat Liver with Digitonin: a Well Defined Short Term Damage of Cellular Metab­olism 880

Rat Hepatocytes Effect of Glucocorticoids, Insulin and a Growth Promoting Tripeptide on the Biosynthesis of Plasma Proteins in Serum-Free Hepatocyte Cul­tures (N) 350

Reassociation Reassociation of Lactic Dehydrogenase from Pig Heart Studied by Cross-Linking with Glu-taraldehyde 772

Receptor Protein Trypsin-Mediated Removal of Herbicide Bind­ing Sites within the Photosystem II Complex . . 98

Receptor Specifity Receptor Specifity and Threshold Concentration in Chemotaxis of the Phaeophyte Cutleria m u l t i -

flda 262 Reconstitution

Reassociation of Lactic Dehydrogenase from Pig Heart Studied by Cross-Linking with Glu-taraldehyde 772

Red Lieht Red Lieht Induced Change in the Saponin Con­tent of Prolamellar Bodies in A vena sativa . . . 869

Redox Potential Is there an Equilibrium between Ascorbic and Dehydroascorbic Acids? (N) 1088

Regulation Regulation of the Synthesis of Ribulose-1,5-bisphosphate Carboxylase and Its Subunits in

the Flagellate Chlorogonium elongatum. II. Coordinated Synthesis of the Large and Small Subunits 942

Reptilia Direct Allosteric Interaction of Oxygen and Bi-carbonate: N-Acetyl-alanyl-seryl-phenylalanine, N-Terminal Sequence of the ß-Chains of the Haemoglobins of Nil Crocoaile (Crocodylus niloticus) and Mississippi Crocodile (Alligator mississippiensis) (N) 902

Resonance Frequency Rotation ot Celle in an Alternating Electric Field: the Occurrence of a Resonance Frequency 173

Respiration Arrhenius Plots Indicate Localization of Photo­synthetic and Respiratory Electron Transport in Different Membrane Regions ofAnabaena . . 1036

Rhodopseudomonas capsulata Isolation and Partial Characterization of the Membrane-Bound NADH Dehydrogenase from the Phototrophic Bacterium Rhodopseudomonas capsulata 400 Molecular and Kinetic Characterization of Xan-thine Dehydrogenase from the Phototrophic Bacterium Rhodopseudomonas capsulata . . . 932 Nitrate Photo-Assimilation by the Phototrophic Bacterium Rhodopseudomonas capsulata E ^ j . 1025

Rhodopseudomonas p a l u s t r i s Molecular Characterization of Glutamine Syn­thetase from the Nitrogen-Fixing Phototrophic Bacterium Rhodopseudomonas p a l u s t r i s . . . . 246 Regulatory Properties of Glutamine Synthetase from the Nitrogen-Fixing Phototrophic Bacteri­um Rhodopseudomonas p a l u s t r i s 784

Rhodopseudomonas sphaeroides I n Vivo Control of Glutamine Synthetase in the Facultative Phototrophic Bacterium Rhodo­pseudomonas sphaeroides 407

Ribulose- 1,5-bispnosphate Carboxylase Regulation of the Synthesis of Ribulose-1,5-bisphosphate Carboxylase and Its Subunits in the Flagellate Chlorogonium elongatum. II. Coordinated Synthesis of the Large and Small Subunits 942

R o b i n i a pseudoacacia The Para-O-Methylation of Apigenin to Acacetin by Cell-Free Extracts of R o b i n i a pseudoacacia L 916

Rumex "Yellow Flavonols" as Components of Pollen Pigmentation 204

Ruta graveolens Rutacridone-epoxide, a New Acridone Alkaloid from Ruta graveolens 200

Rutaceae Rutacridone-epoxide, a New Acridone Alkaloid from Ruta graveolens 200

Rutacridone-Epoxide Rutacridone-epoxide, a New Acridone Alkaloid from Ruta graveolens 200

Salmine Protamines. VII. Circular Dichroism Study of Salmine A I 305

Salts Discrimination of Two Fusogenic Properties of Aqueous Polyethylene Glycol Solutions . . . . 593

1116 Subject Index

Saponin Red Light Induced Change in the Saponin Con­tent of Prolamellar Bodies in A vena sativa . . . 869

Sarcocystis Life Cycle of Sarcocystis between Poikilothermie Hosts. Lizards are Intermediate Hosts for S. p o -darcicolubris sp. nov, Snakes Function as Defini­tive Hosts 1093

Sarcoma 180 Specific Positional Distribution of Acyl Moieties in Phospholipids is not Generally Deleted in Neoplastic Cells 81

Satellite DNA Evolution A Family of Sequences with Regional Homology to Bovine 1.715 Satellite DNA 973

1.715, 1.711b Satellite DNAs A Family of Sequences with Regional Homology to Bovine 1.715 Satellite DNA 973

Secondary Structure Prediction Protamines. VII. Circular Dichroism Study of Salmine A I 305

Senecio cruentus aß-Dehydrocurvularin and Curvularin from A l-ternaria cinerariae (N) 1081

Sensitivity Threshold Receptor Specifity and Threshold Concentration in Chemotaxis of the Phaeophyte Cutleria m u l t i -

fida 262 Sex Pheromone

A Sex Attractant for Sperchia intractana Walker (Lepidoptera: Tortricidae) in New Zealand (N) . 178 Drosophila Males Produce a Pheromone which Inhibits Courtship 694

Sexual Behavior Drosophila Males Produce a Pheromone which Inhibits Courtship (N) 694

Shikimic Acid Effects of Glyphosate on Shikimic Acid Ac­cumulation in Tobacco Cell Cultures with Low and High Yields of Cinnamoyl Putrescines . . 210

Signal-Receptor Receptor Specifity and Threshold Concentration in Chemotaxis or the Phaeophyte Cutleria m u l t i -

fida 262 Silene

Structure and Biosynthesis of Vitexin 2"-0-Xylo-side in Silene alba (N) 484 Methylation of 3',4' Di-OH C-Glycosylflavones in Silene (N) 486

Sinapine Sinapine as a Supply of Choline for the Bio-syntnesis of Phospnatidylcholine in Raphanus sativus Seedlings 215

Sinapis alba Radioactively Labelled Phytic Acid from Matur-ing Seeds of Sinapis alba 383

Small Angel X-Ray Diffraction Fitting of SAXS-Curves by Nonlinear Regres­sion (N) 333

Solanaceae New Cembranoids from Burley Tobacco (N) . . 1077

Solanum tuberosum L. Stimulation of Wound Reactions in Potato Tubers by Thiabendazole 115

Solid State Radiolysis Radiation Damage to Polypeptides and Proteins in the Solid State: Changes in Amino Acid Composition 310

Soybean Induction of Phytoalexin Synthesis in Soybean. Structure and Reactions of Naturally Occurring and Enzymatically Prepared Prenylated Ptero-carpans from Elicitor-Treated Cotyledons and Cell Cultures of Soybean 234

CD Spectra Coa/Coß-Isomerism of the Cobalt Methylated Corrinoids. CD and ORD Spectra of Several Isomer Pairs 497

ORD Spectra Coa/Co/Msomerism of the Cobalt Methylated Corrinoids. CD and ORD Spectra of Several Isomer Pairs 497

Spectroscopy Chromophore Content and Molar Absorptivity of Phytochrome in the P r Form 431

Sperchia intractana A Sex Attractant for Sperchia intractana Walker (Lepidoptera: Tortricidae) in New Zealand (N) . 178

Spin Concentration Paramagnetic Changes in Pulmonary Tumors . 5 On a Possible Mechanism of Action of Interferon 323

Spin State Altered Herne Environments in Opossum and Rabbit Methemoglobins 964

Spinach The Permeability Coefficients of the Plas­malemma and the Chloroplast Envelope of Spin­ach Mesophyll Cells for Phytohormones . . . 672

Spinach Chloroplast Lamellae Isolation and Identification of an Oxygen Re-ducing Factor (ORF) from Isolated Spinach Cholorplast Lamellae 284

Spinacea oleracea "Yellow Flavonols" as Components of Pollen Pigmentation 204 Properties and Subcellular Localization of L-Ala-nine: Aldehyde Aminotransferase: Concept of an Ubiquitous Plant Enzyme Involved in Sec­ondary Metabolism 625

Spiroacetals Pheromone Bouquet of the Mandibular Glands in A n d r e n a haemorrhoa F. (Hym., Apoidea) . . 928

Spleen The Specific Labeling in Hypertonie Medium of a Spleen Protein (N) 183

Spodoptera littoralis Fatty Acid Composition of Eggs during De­velopment of the Cotton Leaf-Worm, Spodoptera littoralis Boisduval 562

Springene Mammalian Pheromone Studies, IV. Terpenoid Compounds and Hydroxy Esters from the Dor­sal Gland of the Springbok, A n t i d o r c a s mar-supialis (N) 340

Stability of Chlorophylls Light-Induced Accumulation and Stability of Chlorophylls and Chlorophyll-Proteins during Chloroplast Development in Radish Seedlings 421

Steroidal High Performance Liquid Chromatographie Analysis of Steroidal Saponins from Avena sativa L. 1072

Sterol Biosynthesis The Effectt of Clotrimazole and Triadimefon on 3-Hydroxy-3-Methyl-Glutaryl-CoA-Reductase-[EC 1.1.1.34]Activity in Saccharomyces cerevisiae 798

Sterylglucosides Initial Phases of Growth Induced by Sterylglu­cosides and Indole-3-acetic Acid in Avena Coleoptiles (N)

Stick Insects Carotenoids in the Stick Insect, Ectatosoma ti-a r a t u m Isolation of ß,f-Caroten-2-ol and ß,e-Caroten-2-one

Stizolobium hassjoo Biosynthesis of 3-Carboxy-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline and 1-Methyl-3-carboxy-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline in a Callus Culture of Stizolobium hassjoo . . . .

Strain Specificity Volatile Terpenes from Ceratocystis ßmbriata (N)

Strictosidine Synthase Medium-Induced Formation of Indole Alkaloids and Concomitant Changes of Interrelated En­zyme Activities in Cell Suspension Cultures of C a t h a r a n t h u s roseus

Stridulation An Audiospectrographic Study of Male Stridu­lation in the Genus Corixa Geoffr. (Hemiptera, Corixidae)

Structure Three Dimensional Structure of the Carbo-hydrate Moiety of a Lipopolysaccharide. Com­puter Calculations

Subcellular Localization Properties and Subcellular Localization of L-Ala-nine: Aldehyde Aminotransferase: Concept of an Ubiquitous Plant Enzyme Involved in Sec-ondary Metabolism

Subunits Regulation of the Synthesis of Ribulose-1,5-bisphosphate Carboxylase and Its Subunits in the Flagellate Chlorogonium elongatum. II. Coordinated Synthesis of the Large and Small Subunits

Succulence Succulence - Induction in Kalanchoe bloß-

f e l d i a n a under Long-Day Conditiones by a Lipo-phyle Fraction out of Fiowering Kalanchoe and MS-Identification of Pterosterone

Sucrose Ferulic Acid-Sucrose Esters from Immature Anthers of Tulipa cv. "Apeldoorn"

Sulphonyl Group Incorporation I n Vitro Biosynthesis of the Plant Sulpholipid: On the Origin of the Sulphonate Group . . . .

Surface Enhanced Raman Scattering Hydrogen-Deuterium Exchange in Adenosine 5'-Monophosphate Detected by Surface En­hanced Raman Scattering (SERS)

Suspension Cultures Effects of Glyphosate on Shikimic Acid Ac­cumulation in Tobacco Cell Cultures with Low and High Yields of Cinnamoyl Putrescines . .

Synchrotron X-Ray Fitting of SAXS-Curves by Nonlinear Regres­sion

Synchronous Yeast I n vivo Evidence for a Functional Glycolytic Compartment in Synchronous Yeast Cells . . .

Synechococcus Light-Dependent Changes in the Lipid and Fat­ty Acid Composition of Phycocyanin-Free Photosynthetic Lamellae of Synechococcus . .

Subject Index 1117

Ultrastructure of Differently Pigmented Sy­nechococcus Cells (N) 907

Synthesis 900 Regulation of the Synthesis of Ribulose-1,5-

bisphosphate Carboxylase and Its Subunits in the Flagellate Chlorogonium elongatum. IL Coordinated Synthesis of the Large and Small

755 Subunits 942 Synthesis of Halogeno Analogues

Solution Conformation of Benzimidazole Nu-cleosides with the Aid of Model Analogues . . 126

Synthetase 921 A Thioredoxin Activated Glutamine Synthetase

in Chlorella 396

1075

Taphozous melanopogon Effect of Lithium Chloride on the Cricadian Rhythm in the Flight Activity of the Micro-

40 chiropteran Bat, Taphozous melanopogon . . . 1068 Teleosts

Are Yolk Phosvitins Carriers for Specific Cations? Comparative Microanalysis in Ver-

189 tebrate Yolk Platelets (N) 686 Teratogenicity

Thalidomide-Like Malformations Caused by a Tween Surfactant in Mice (N) 904

71 Terpenes On the Essential Oil Components from Majorana hortensis Moench 23 On the Essential Oil Components from A r t e m i s i a a b s i n t h i u m L 369

625 On the Composition of the Essential Oil from A r t e m i s i a dracunculus L. during the Vegetation Period 724

Terpenoids Mammalian Pheromone Studies, IV. Terpenoid Compounds and Hydroxy Esters from the Dor-

942 sal Gland of the Springbok, A n t i d o r c a s mar-supialis (N) 340

Territorial Marking Mammalian Pheromone Studies, V. Compounds from the Preorbital Gland of the Grysbok,

465 Raphicerus melanotis (N) 344 11 -Tetrad ecenyl Acetate

A Sex Attractant for Sperchia intractana Walker 721 (Lepidoptera: Tortricidae) in New Zealand . . 178

Teucardosid Iridoids in Some Teucrium and Ajuga Species . 697

820 Teucrium Iridoids in Some Teucrium and Ajuga Species . 697

Thalidomide-like Malformations Thalidomide-Like Malformations Caused by a

809 Tween Surfactant in Mice (N) 904 Thermoluminescence

Reinvestigation of the Effects of Disali-cylidenepropanediamine (DSPD) and 2-Heptyl-

210 4-hydroxyquinoline-N-oxide (HQNO) on Photo­synthetic Electron Transport 109 Two Sites of Inhibition of the Photosynthetic

333 Electron Transport Chain by the Herbicide Tri-fluralin 853

Thiabendazole 615 Stimulation of Wound Reactions in Potato

Tubers by Thiabendazole 115 Thioredoxin

A Thioredoxin Activated Glutamine Synthetase 856 in Chlorella 396

1118 Subject Index

4-Thiouridine Influence of Crystal Packing Forces on Molecu­lar Structure in 4-Thiouridine. Comparison of a n t i and syn Forms 956

Thylakoid Composition Partition of Phylloquinone K! between Digi­tonin Particles and Chlorophyll-Proteins of Chloroplast Membranes from Nicotiana tabacum 276

Thylakoid Membrane Which Polypeptides Are Characteristic for Photosystem IIV Analysis of Active Photosystem II Particles from the Blue-Green Alga Anacystis nidulans 295

Thylakoids Esterification of Chlorophyllide in Prolamellar Body (PLB) and Prothylakoid (PT) Fractions from A vena sativa Etioplasts 58 Comparative Binding of Photosystem II - Herbi-cides to Isolated Thylakoid Membranes and In-tact Green Algae 1041

Tobacco Mutants The Kok Effect and Its Relationship to Photore­spiration in Tobacco 450 Dependence of Photorespiration and Photo­synthetic Unit Sizes on Two Interdependent Nu­clear Gene Factors in Tobacco 662

Tortricidae A Sex Attractant for Sperchia intractana Walker (Lepidoptera: Tortricidae) in New Zealand (N) . 178

Tracking Courtship-Like Tracking Behaviour in Wild-Type Female Drosophila melanogaster . . . . 475

Transcarboxylase Evidence for a Transcarboxylase Reaction in Maize Chloroplast Extracts (N) 688

Transplantable Tumours Intracellular Effect of Hydroxyalkenals on Ani-mal Tumors 572

Trichoplax DNA Content and Fragmentation of the Egg Nucleus of Trichoplax aanaerens 564

Trifluralin Two Sites of Inhibition of the Photosynthetic Electron Transport Chain by the Herbicide Tri­fluralin 853

1,2,4-Trihydroxybenzene Metabolites of 1,2,4-Trihydroxybenzene from Fruiting Bodies of Gomphidius maculatus and G. glutinosus (Boletales) [1] (N) 488

Tropic Acid Biosynthesis Chemical Synthesis of a-Formylphenylacetic Acid, the Postulated Precursor of Tropic Acid . 611

Tryptophan Decarboxylase Medium-Induced Formation of Indole Alkaloids and Concomitant Changes of Interrelated En­zyme Activities in Cell Suspension Cultures of Catharanthus roseus 40

Tryptophan Synthase Interactions between Tryptophan Synthase from Escherichia coli and Derivatives of the Coen­zyme Pyridoxal 5'-Phosphate 778

Tulipa Purification of Chalcone Synthase from Tulip Anthers and Comparison with the Synthase from Cosmos Petals 30 Ferulic Acid-Sucrose Esters from Immature Anthers of Tulipa cv. "Apeldoorn" 721

UDP-Galactose Lipid Labelling in Intact Chloroplasts from Ex­ogenous Nucleotide Precursors 62

Ultrastructure Ultrastructure of Differently Pigmented Sy­nechococcus Cells (N) 907

1 802-Uptake The Kok Effect and Its Relationship to Photore­spiration in Tobacco 450

Urease Location of Several Enzyme of L-Arginine Ca-tabolism in Evernia p r u n a s t r i Thallus (N) . . . 692

U rodele Lateral Line System Electroreceptors and Direction Specific Arrange­ment in the Lateral Line System of Salaman­ders? (N) 493

L-Usnic Acid Purification and Properties of a New Enzyme from Evernia p r u n a s t r i , which Reduces L-Usnic Acid 35

Usnic Acid Dehydrogenase Purification and Properties of a New Enzyme from Evernia p r u n a s t r i , which Reduces L-Usnic Acid 35

Vanadate Effect of Vanadate and Iron Stress on the Pig­ment Composition of Chlorella Fusca 207

Vascular Tissue Distribution of Phenylalanine Ammonia-Lyase and 4-Coumarate: CoA Ligase in Oat Primary Leaf Tissues 389

Vectors Oviposition Deterrance Activity in Some Lami-aceae Plants against Some Insect Pests . . . . 122

Vision Action Potentials lin "Non-Spiking" Visual In­terneurones 470

Vitamin B 1 2

About the Iron Analogues of Cobalamin and Cobyric Acid 9 Coa/Co/Msomerism of the Cobalt Methylated Corrinoids. CD and ORD Spectra of Several Isomer Pairs 497 X-Ray Crystal Structure Analysis of Factor A (2- Methyladeninyl-cyanocobamide), a Native Vitamin B12-Analogue 506

Vitamin B12-factor A (2-Methyladeninyl-cyanocoba-mide)

X-Ray Crystal Structure Analysis of Factor A (2- Methyladeninyl-cyanocobamide), a Native Vitamin B12-Analogue 506

Vitexin Structure and Biosynthesis of Vitexin 2"-0-Xylo-side in Silene alba (N) 484

Volatile Metabolites Volatile Terpenes from Ceratocystis ßmbriata (N) 1075

Waterbug An Audiospectrographic Study of Male Stridu-lation in the Genus Corixa Geoffr. (Hemiptera, Corixidae) (N) 189

Wound Reactions Stimulation of Wound Reactions in Potato Tubers by Thiabendazole 115

Subject Index 1119

X-Ray Crystal Structure Analysis X-Ray Crystal Structure Analysis of Factor A (2- Methyladeninyl-cyanocobamide), a Native Vitamin B12-Analogue 506

X-Ray Diffraction X-Ray Studies on Phospholipid Bilayers. I. Poly­morphie Forms of Dimyristoyl Lecithin . . . . 875

Xanthine Dehydrogenase Molecular and Kinetic Characterization of Xan­thine Dehydrogenase from the Phototrophic Bacterium Rhodopseudomonas capsulata . . . 933

2"-0-Xyloside Structure and Biosynthesis of Vitexin 2"-0-Xylo-side in Silene alba (N) 484

Yeast Initiation of Protein Synthesis in Yeast: Binding ofMet-tRNAi 142 I n vivo Evidence for a Functional Glycolytic Compartment in Synchronous Yeast Cells . . . 615

Zea mays A H + / C a 2 + Antiporter in Membranes of Microsomal Vesicles from Maize Coleoptiles, a Secondary Energized C a 2 + Pump 1009

Zinc Cadmium as a Growth Factor for the Mushroom Agaricus abruptibulbus (Peck) Kauffmann . . . 765

Volume 36 c Zeitschrift für Naturforschung 1981

Authors Index

Abd-El-Fattah, M. 350 Akavia,N. 378 Alef, K. 246, 784 Andre, M. 662 Ardenne, R. von 488 Aretz,W. 933 Arfmann, H.-A. 319 Arntzen, Ch. J. 98 Asmus, U. 23

Bader, K .P . 662 Baibach, N . 552 Balk, H. 778 Barber,J. 1021 Barckhausen, R. 907 Bartholmes, P. 778 Barz,W. 338 Bassemir, U. 326 Baumeister, W. 310, 1091 Baydoun, H. 319 Becker, L. J. M. 207 Beddard, G. 1021 Benemann, J. R. 87 Benn, M. H. 178 Bensch, K. G. 1,5 Benwitz, G. 564 Benz,J. 51,58 Berg, D. 798 Bergström, G. 928 Berlin, J. 40,210 Bernhardt, G. 772 Bertanzon, F. 305 Bertrams, M. 62 Beulen, Ch. 389 Bhosale, A. S. 122 Bieganowski, R. 9, 506 Bigalke, R. C. 340,344 Blaicher, F. M. 383 Blessing, J. 884 Bios, I. 417 Boctor, I. Z. 562 Boege, F. 942 Böger, P. 633, 1036 Böttger, I. 464 Boland,W. 262 Bonara, G. M. 305 Bornemann, S. 135 Bothe, H. 1030 Brandlmeier, Th. 431, 440 Braunitzer, G. 902 Brederode, J. van 484, 486 Britsch, L. 742 Brody,S.St. 638, 1013,

1021 Brosche, Th. 23, 369 Bruemmer, U. 1077 Budzikiewicz, H. 728 Burger, B. V. 340, 344 Burger, G. 645 Burkard, G. 421 Burkardt, H.-J. 246

Caballero, F. J. 1025 Cärdenas, J. 1025 Castillo, F. 1025 Chopin, J. 1084

Claviez, M. 490 Cohen, A. 378 Collins, F. W. 730 Cook,R. 475

Dahm, K. H. 579 Dancker, P. 1050 Daniell, H. 656 Datz, G. 856 Dawson, J. R. O. 157 De Luca, V. 730 Dellamonica, G. 1084 Demeter, S. 109, 853 Demmig, B. 672 Dernick, R. 164 Deuten, K. von 506 Dickerson, P. E. 157 Diringer, H. 183 Döhler, G. 93, 834, 856,

907 Doenecke, D. 149 Dorn-Zachertz, D. 988 Draber, W. 798, 848 Drews, G. 400 Drqppa, M. 109, 853 DuBois, R. N . 964 Dudycz, L. 126 Durchschlag, H. 516

Eckert, H. E. A. 470 Eckstein, H. 813 Ehrenfeld, M. 545 Eilert,U. 200 El-Sharaky, A. S. 1086 Elstner, E. F. 115,284 Engelhardt, H. 407 Entzeroth, M. 180 Erb, N . 336 Estevez, M. P. 35

Falk,H. 353 Feustel, H. 5 Filby, W. G. 1088 Filier, R.-D. 5 Finke, Ch. 189 Firl,J. 284 Fölster, E. 262 Forkmann, G. 411,619,

737 Formanek, H. 71 Fouad, F. M. 350 Francke, W. 928 Fredericks, P. M. 242 Friedrich, W. 9, 506 Fritzsch, B. 493 Frommeyer, D. 284

Galbreath, R. A. 178 Gawronska, M. 361 Gemeinhardt, F. 23 Gerster, R. 662 Gerstner, E. 893 Gialanella, G. 980 Gilles, I. 751 Gimmler, H. 672, 679 Gmelin, R. 16

Godde, D. 272 Gömez P., L. D. 896 Goody, R. S. 534 Gregory, R. P. F. 638 Grell, K. G. 564 Grisebach, H. 234, 742 Gross, G . G . 611 Grossi, G. F. 980 Günther, H. O. 586 Gupta, A. S. 122

Häger, K.-P. 1030 Hager, A. 997, 1009 Hall, J. C. 694 Hallenbeck, P. C. 87 Hamdorf, K. 470 Hansen, B. 40 Hanssen, H.-P. 1075 Hartmann, Th. 625 Härtung, W. 672, 679 Hauer, J. 366 Haustein, D. 790 Heemann, V. 1077 Hegnauer, R. 336 Heitmann, D. 672, 679 Heinz, E. 62 Heller, W. 742 Heimle, M. 997 Hemleben, V. 925 Henssen, A. 893 Herbertz, L. M . 310, 1091 Hermsdorf, P. 1009 Heukeshoven, J. 164 Holt,V.A. 178 Hoppe, W. 820 Horstmann, H.-J. 246 Horväth, G. 109, 853 Hugo, H. von 798 Hummel, W. 798 Hunkler, D. 714 Hunsmann, G. 353

Ibrahim, R. K. 730 Ihm, H. 369, 724 Interschick-Niebler,

E. 276 Ishii,R. 450

Jägers, E. 488 Jaenicke, L. 180,262 Jaenicke, R. 84, 778 Jakoby, K. 262 Janistyn, B. 193, 455 Jay, M. 730 Jeck, R. 545 John, M. E. 964 Jonak, R. 333 Joshi,V. 122

Kaetsu, I. 1062 Kaiser, F. 888 Kalbitzer, H. R. 534 Kalus, W. H. 1088 Kamps-Heinsbroek,

R. 484,486 Kang, Sa-Ouk 1

Kapoulas, V. M. 459 Karl, Ch. 607 Kaspari,H. 933 Kayser, H. 755 Kazimierczuk, Z. 126 Kesselmeier, J. 1072 Khoschsorur, G. 572 Kiewitt, I. 81 Kinzel,V. 552 Klatte, W. 545 Klemme, J.-H. 407, 933 Kliche, A. 1050 Knack, I. 347 Knobloch, K. 23. 369, 724 Knobloch, K.-H. 40 Knogge,W. 197,389 Knops, H. J. 848 Koch, M. A. 183 Koch, V. 385 Kocher, W. 904 Kocher-Becker, U. 904 Kochian, L. V. 87 Koelen,K.J. 611 Koenig, F. 295 König, W. A. 385 Koglin, E. 809 Kohorst, G. 913 Komamine, A. 921 Koolman, J. 790 Kopf,J. 506 Korth, H. 728 Krailling, H. 593 Kremer, B. K. 840 Kreutzfeldt, Ch. 142 Kröger, H. 459 Kubier, D. 552 Kühn, N . 545 Kuhn, G. 421 Kulamowicz, I. 361 Kumpe,E. 1951 Kuppert, P. 326 Kuroki, G. 916

Laasen, H. 1041 Lambert, R. 633 Lammel, G. 708 Lange, R. H. 686 Laughlin, S. 910 Legaz, E. 35, 692 Leser, K. H. 597 Leysing, B. 956 Lichtenthaler, H. K. 276,

421,645 Liedgens, W. 44 Liefländer, M. 968 Löffler, H.-G. 751,951 Löffler, M. 255 Lohmann, W. 1, 5, 323,

804 Lüdemann, H.-D. 84, 366 Lütfring, H. 338 Lütz, C. 58

Macchiato, M. F. 980 Malorni, M. C. 157 Malterud, K. E. 896

Authors Index 1121

Marx, R. 149 Maschler, R. 568 Masson, K. 272 Mastronicolis, S. K. 459 Matuschka, F.-R. 1093 Maurer, H. R. 568 Mayer, D. 798 Meisch, H.-U. 207, 765 Merkl, I. 778 Michaelis, K. 724 Moretto, V. 305 Morris-Krsinich, B. A.

M. 157 Moskophidis, M. 497 Müller, A. 611 Müller, D. G. 262 Müller, E. 1,5 Müller, G. 607 Müller, M. 869 Mukherjee, K. D. 81,383 Mutert, W.-U. 338 Musso, H. 645

Nahrstedt, A. 200, 336 Nanda, B. 122 Nemetschek, Th. 333 Niehuss, M. 115 Niemann, G. J. 1084 Novellie, P. A. 344

Obata-Sasamoto, H. 921 Ockenfels, H . 904 Oettmeier, W. 272 Ohsima, T. 400 Oliriski, R. 361 Olmeda, L. 35

Pabst, H. W. 464 Pan, D. 688 Patwardhan, S. 122 Paulsen, Ch. 1077 Pedersen, P. A. 607 Perez, F. J. 35 Peter, M. G. 579 P fister, K. 98,645, 1041 Pils, I. 115 Pilwat, G. 173 Platt, D. 880 Plucienniczak, A. 973 Poppe, Chr. 333 Postius, St. 615, 880 Poulten,J.E. 916 Prager, J. 189 Prenzel,U. 421 Proksch, M . 222, 357 Pulverer, G. 728 Pyerin, W. 552

Rakow, D. 16 Rastogi, P. P. 961 Rehse, C. 204 Reiffen, K. A. 255 Reisen, J. 1086 Reiter, M. 572 Reith, W. 928 Rembold, H. 466 Renner, B. 893 Reum, L. 790 Riedl, H. 333 Rimpler, H. 697, 708 Robeson, D. J. 1081 Rodriguez, E. 357 Röhm, K.-H. 347 Roller, H. 579 Römer, A. 721,728 Rösch, P. 534, 539 Roßlenbroich, H.-J. 834 Roux, M. le 340, 344 Rözsa, Z. 109 Rudolph, R. 772 Rüdiger, W. 51,58,431,

440, 827 Rueß, K.-P. 968 Ruhdorfer, J. 697 Ruhenstroth-Bauer,

G. 350,464 Ruppel, M. 907 Ruthmann, A. 564

Sachs, G. 721 Saenger, W. 956 Saito.K. 921 Salonen, E. 863 Sandermann, H. 714 Sandmann, G. 633 Sarkar, S. 884 Sarojini, G. 656 Schäfer, W. 417, 902 Schaller, E. 234 Schauenstein, E. 572 Schaur, R. J. 572 Scheer,H. 417,431,827 Scherer, R. 350 Scherer, S. 1036 Schiff, J. A. 827 Schilling, V. 333 Schlimme, E. 135 Schmid, G. 84 Schmid, H. G. 450,662 Schmidt, A. 396 Schmidt, H. 586 Schmidtberg, G. 611 Schmitt, J. A. 765 Schneider, F. 255,751,

951

Schneider, Hj. A. W. 44 Schneider, J. 353 Schoch, S. 827 Scholl, A.-R. 765 Schreiber, J. 5 Schwander, E. 333 Schwemmle, K. 5 Schwenn, J. D. 820 Seehofer, F. 1077 Seredynski, J. 310 Sequaris, J. M. 809 Sharma, R. N . 122 Shirk, P. D. 579 Shugar, D. 126 Sieber, K.-P. 466 Siegeimann, H. W. 827 Sinnwell, V. 1077 Skowronski, J. 973 Söylemez,T. 310, 1091 Spies, H. S. C. 340, 344 Spindler, K.-D. 326 Spindler-Barth, M. 326 Sprecher, E. 1075 Spremberg, G. 1077 Spribille,R. 619 Stangl, A. 902 Steffan, B. 488 Steglich, W. 488 Steinback, K. E. 98 Steiner, R. 417 Stolarski, R. 126 Stotz,G. 411,737 Strack, D. 197,215,222,

338, 378,721, 1072 Strecker, W. 464 Strobel,G.A. 1081 Stürzl, E. 1036 Subbaraj, R. 1068 Sütfeld,R. 30 Summers. L. A. 242 Suwalsky, M. 875 Szabo, Z. 888

Tan, K. H. 688 Tapia, J. 875 Taugner, G. 1056 Tengö, J. 928 Thies, W. 16 Thümmler, F. 440 Tietz, A. 900 Tiilian, H. M. 572 Tjon Sie Fat, L. 336 Tompkins, L. 694 Toniolo, C. 305 Triantaphylides, Ch. 662 Trebst, A. 848 Tredwell,C. 1021

Trenck, K. T. v. d. 714 Trim,A.R. 157 Truter, V. 340, 344

Urbach, W. 1041

Valenta, P. 809 Verhoeven, J. W. 366 Vernon,L.P. 295 Vicente, C. 35, 692 Vienken, J. 173 Vogel, W.O. P. 490 Voirin,B. 730 Volm,M. 81 Vostrowsky, O. 23, 369,

724 Vuento, M. 863

Walter, Z. 361 Watermann, M. R. 964 Wayss,K. 81 Weber, N . 81 Weidner, H. 71 Weissenböck, G. 197, 222,

389 Westhoff, P. 942 Wiermann, R. 30, 204,

721 Wieschhoff, H. 417 Wink,C. 625 Wisdom, Ch. 357 Witte, L. 210 Woenckhaus, Ch. 545 Wollenweber, E. 204, 604,

896, 913 Wolters, B. 200 Wrage,K. 62 Wray,V. 200 Wunderlich, I. 1056

Yamada,A. 1062 Yoshü, F. 1062 Young, H. 178

Zadu, G. 122 Zähringer, U. 234 Zahn, M. 645 Zbikowska, M. 361 Zetsche, K. 942 Zimmer, G. 586, 988 Zimmermann, U. 173,

942 Zintl,R. 369,724 Zinsmeister, H. D. 336 Zipper, P. 516 Zumft, W. G. 246, 784 Zundel, G. 961

Pyropheophytin a Accompanies Pheophytin a in Darkened Light Grown Cells of E u g l e n a 1

Siegrid Schoch 2 , 3 , 4, Hugo Scheer3, Jerome A. Schiff2,5, Wolfhart Rüdiger 3, and Harold W. Siegelman6

2 Institute for Photobiology of Cells and Organelles, Brandeis University, Waltham, MA 02254 3 Botanisches Institut der Universität München, Menzinger Str. 67, D-8000 München 19,

Bundesrepublik Deutschland 6 Department of Biology, Brookhaven National Laboatory, Upton, New York

Z. Naturforsch. 36 c, 827-833 (1981); received June 19,1981

Euglena, Chlorophyll Degradation, Pyropheophytin, Photosynthesis, High Performance Chromatography

Light-grown non-dividing cells of Euglena gracilis Klebs var. bacillaris Cori form pheophytin a like pigments from Chlorophyll a without loss of viability when they are allowed to incubate in darkness without shaking. This is accompanied by the loss of long-wavelength components in the red absorption band of intact cells. After extraction of these cells with acetone, transfer of the pigments to ether and treatment of the ether Solution with dilute acid, two pigments can be separated by high Performance liquid chromatography on reverse phase silica gel (RP-8) using methanol: water = 95:5 (v/v) as the eluting solvent: In addition to pheophytin a, the eluate contains an unknown pigment. With increasing times of incubation of the cells in darkness, the proportion of pheophytin a decreases and the proportion of the unknown increases suggesting, that the unknown is formed from pheophytin a. This pigment has been identified as pyropheophytin a. It has the same absorption spectrum as pyropheophytin a (prepared by Pyridine pyrolysis of pheophytin a) and contains phytol as the longchain esterifying alcohol. On conversion to the methyl ester, the resulting methyl phorbide is identical with authentic pyromethylpheophorbide a by tlc, hplc, absorption, absorption difference and mass spectros-copy. This is the first report of pyropheophytin a or any pyrochlorophyll derivative from plants or oxygenic plant-like microorganisms where it may serve as an intermediate in Chlorophyll degradation.

Introduction

The biosynthesis [1-4] and breakdown [5, 6] of porphyrin complexes (hemes) is well established, but for the magnesium porphyrins (Chlorophylls and bacteriochlorophylls) only the biosynthetic pathway is known in some detail [1, 2, 7]. Particularly obscure, is the pathway of Chlorophyll degradation in cells and the nature of the chemical intermediates in this process [8, 9]. Light-grown cells of E u g l e n a gracilis var. b a c i l l a r i s placed in darkness without

1 Supported by grants from the National Institutes of Health (GM 14595), the Deutsche Forschungsgemein­schaft and the Department of Energy. 4 Supported by a fellowship from the Deutsche For­schungsgemeinschaft while on research leave at Brandeis University, current address see (3). 5 Dr. J. A. Schiff is the Abraham and Etta Goodmann Professor of Biology. Reprint requests should be sent to Dr. Schoch (München) and Dr. Schiff at the Photobiology Institute (Waltham). Abbreviations: Chi = Chlorophyll a, Phe = pheophytin a, Phyrophe = pyropheophytin a, HPLC = high Performance liquid chromatography, TLC = thin layer chromatography. 0341-0382/81/0900-0827 $01.00/0

shaking convert a large proportion of their Chloro­phyll a to a pheophytin (Phe)-like pigment [10]. This appeared to be a promising system in which to look for other possible intermediates in Chlorophyll degradation. In this paper we provide further information concerning pheophytin formation in E u ­glena and show that pyropheophytin a (Pyrophe) (a derivative of Phe lacking the carboxymethyl group on the isocyclic ring [11]) is also formed.

Materials and Methods

All commercial chemicals used in this study were reagent grade or better and all solvents used in the chemical characterization of pigments were distilled prior to use. E u g l e n a gracilis Klebs var. b a c i l l a r i s Cori was grown in one liter of the pH 3,5 me­dium of Hutner at 260 with shaking as described previously [10, 12]. Illumination was supplied by mixed white and red fluorescent lamps providing a light intensity of 150 ft c (180 uW • cm-2) at the surface of the culture [12]. When the cells reached about 2 x 106 cells/ml (three days of growth) the

828 S. Schoch et a l • Pyropheophytin a Accompanies Pheophytin a in Darkened Light Grown Cells of E u g l e n a

culture was centrifuged at 500 x g for 1 min at room temperature [13]. The pellet was resuspended in the same volume of resting medium (1.0% (w/v) with respect to mannitol, 0.01 M with respect to MgCl 2 , 0.01 M with respect to KH 2 P0 4 and 0.25% (w/v) with respect to eis, eis, eis, eis-1,2,3,4-cyclopentane-tetracarboxylic acid (Aldrich) adjusted to pH 3.5 with KOH [14]). All of these manipulations were done aseptically. The cell Suspension so obtained was shaken at 26 0 under illumination as before, for three more days. Aliquots were then placed in the dark at 26 ° without shaking, or in some cases in the light, with shaking for various times. Dim green safelights [15] were used when necessary. Absorp­tion spectra of these cells were measured as pre-viously described [13]. Cell viability was measured as colony formation after plating the cells on pH 3.5 medium as described previously [16].

Each sample was then centrifuged at 800 x g for 5 min at room temperature and the cell pellet was resuspended in 100 ml of 0.1M potassium phos­phate buffer, pH 7.0, at room temperature and was centrifuged. The following Steps were peformed under dim laboratory lighting. The pellet was resus­pended in 100 ml of cold acetone and was centri­fuged at 8000 x g for 5 min at 4 °C. The extraction was repeated three times to yield a total of about 350 ml of cold extract. The pigments were then transferred into fresh cold peroxide-free diethyl ether [17], and the ether was acidified by the addition of 10% (v/v) HCl (about 5 ml of acid for each 100 ml extract), washed neutral with distilled water, dried overnight over anhydrous sodium Sul­fate, and evaporated in vacuo at about 25°. The dry pigments were stored at - 2 0 ° under nitrogen in darkness.

For some experiments, part of this crude pigment fraction was further separated by chromatography on silica gel thin layer plates (silicagel 60, Merck), using carbon tetrachloride/acetone = 9/1 (v/v) as the solvent [18]. The rapidly moving pheophytin a region was eluted with acetone, the eluate was taken to dryness in vacuo and the pigment was stored under nitrogen at — 20 °.

To determine the nature of the esterifying alcohol, the pigment was saponified with methanolic KOH as described previously [21]. The alcohols obtained were identified by gas chromatography using pre­viously described methods [19]. Analytical high Performance liquid chromatography (HPLC) [19]

was carried out with a Laboratory Data Control (LDC) constametric II pump, using either an LDC Model 1202 variable wavelength double beam ab-sorbance detector set at 667 nm, or a Schöffel model FS 970 L.C. fluorescence detector (A e x c = 408 nm, X e m >580 nm). The Separation of the pigments solu­bilized in acetone was performed using a stainless steel column (15x0.5 cm) packed with LiChrosorb RP-8/5 um (Merck). Methanol/water (95/5 v/v) was used as eluant at a flow-rate of 1.0 ml/min. Pre-parative HPLC employed previously published pro-cedures [20]. Absorption and derivative spectra in the visible and ultraviolet regions were recorded on a model 320 spectrophotometer (Perkin-Elmer). Coupled HPLC-absorption spectroscopy was per­formed in a homebuilt System using a model II double beam variable wavelength detector (LDC-Latek) combined with a model 8000 intelligent recorder (Bryans) for scanning and data manipula-tion. Details of the method will be published separately. Mass spectra were recorded on a model CH 7 mass spectrometer (Varian) in the El-mode (70 KV) with direct inlet.

Pyropheophytin a

An authentic sample of Phe was obtained from crude pheophytin "Sandoz". It was converted to Phyrophe by refluxing in pyridine for 12 h under nitrogen [11, 18].

Pyromethylpheophorbide a

For transesterification (replacement of the phytyl group by methyl on the propionic acid side chain) the unknown pigment was refluxed for 1 h in Chloroform methanol (1:1 v/v) containing 2.5% (v/v) H 2 S0 4 . The produets were purified by Stan­dard procedures, involving T L C on 20 x 20 cm glass plates coated with 0.75 mm silica "H" (Merck) using 4% (v/v) acetone in carbon tetrachloride as the developing solvent [18].

Authentic pyromethylpheophorbide was prepared from Phe by transesterification and subsequent pyrolysis to remove the carbomethoxy group [18]. Analytical TLC was done with commercial plates (HPTLC, Merck, 10 x 10 cm). Either a silica coating developed with 6% (v/v) acetone in carbon tetra­chloride or a C-18 reverse phase coating with methanol as solvent was used.

S. Schoch et a i • Pyropheophytin a Accompanies Pheophytin a in Darkened Light Grown Cells of E u g l e n a 829

Fig. 1. Absorption spectra of acetone extracts of light-grown non-dividing cells of Euglena maintained in the light with shak­ing or in darkness without shaking for 148 h.

O.l

0

432 LIGHT-GROWN NON-OIVIDING EUGLENA

ACETONE EXTRACT

i LIGHT (+ SHAKING) (148 hrs.)

4 0 0 450 500 550 600 WAVELENGTH (nm)

650 700

Results and Discussion

Acetone extracts of normal light-grown non-divid­ing cells of E u g l e n a shaking in the light show ab­sorption peaks due to the presence of Chi (432 nm and 662 nm) and carotenoids (Fig. 1). Extracts of the same cells incubated in darkness without shak­ing show additional absorption peaks at 410 nm and 535 nm attributable to Phe-like pigment(s) [10]. In either culture, there is no significant loss of cell viability during the experimental period as deter-mined by plating (data not shown).

Evidence of pheophytin a formation is also seen in the absorption spectrum of intact cells main­tained in darkness without shaking (Fig. 2). There is an increased absorption at 413 nm expected for the Soret band of Phe. Also evident is a loss of absorption on the long wavelength side of the red absorption region. A similar selective loss of Chloro­phyll a components absorbing at longer wavelengths has been observed during Phe formation in E u g l e n a cells growing in the presence of 3-(3,4-Dichloro-phenyl)-l,l-dimethylurea (DCMU) in the light [22]

LIGHT-GROWN NON-DIVIDING 433 EUGLENA

«* WAVELENGTH (nm) > Fig. 2. Absorption spectra of intact light-grown non-divid­ing cells of Euglena maintained in the light with shaking or in darkness without shaking for 96 h.

830 S. Schoch et a l • Pyropheophytin a Accompanies Pheophytin a in Darkened Light Grown Cells of E u g l e n a

and is attributed to a selective loss of the light-harvesting Systems of photosystem I of photosyn-thesis. Perhaps inhibition of normal light-driven hydrogen ion pumping by darkness or DCMU allows accumulation of H + near the Chlorophyll of photosystem I leading to pheophytin formation.

To elucidate the structure of the pigment(s) formed from Chi, they were extracted from the cells and the extracts were acidified to convert all re-maining Chlorophyll (s) to pheophytin(s). The crude mixture was then subjected to chromatography. Whereas only a Single band is obtained on silica tlc-plates, two components can be separated by reverse-phase HPLC (Fig. 3). One peak is chromatograph-ically identical with Phe (r= 16.2 min) as expected since any remaining Chi was converted to Phe by acidification during the preparative procedure. It is accompanied by a second peak eluting later (r = 23.2 min). During incubation of the cells in dark­ness, the unknown Compound increases at the ex-pense of Phe suggesting that the latter is pro­gressive^ converted to the unknown Compound (Fig. 3, inset). In situ spectroscopy of the HPLC eluate at the two maxima (Fig. 3) gave identical absorption spectra indicating either the presence of a different esterifying alcohol or a chromophore modified at a position not severely affecting the n-electron System. To test these possibilities larger amounts of the unknown pigment were isolated

using preparative HPLC. After saponification the only long chain alcohol found by gas chromatog­raphy is phytol, excluding the first possibility. The amount of phytol found is greater than expected using the known extinction coefficient for Phe to estimate the amount of pigment saponified. This indicates that the extinction coefficient of the un­known pigment is lower than that of Phe.

These properties of the unknown pigment sug-gested that it might be a pheophytin carrying different substitutents at C-132 than pheophytin a. In particular the absorption spectrum of the un­known pigment is essentially the same as that of pyropheophytin a, a derivative lacking the 132-carbomethoxy group [11, 18, 23]. This Suggestion was substantiated by the chemical correlations shown in Fig. 4. Heating of pheophytin a with Pyridine yielded pyropheophytin a, which is identi­cal with the unknown pigment (r = 23.2 min) by HPLC, TLC and uv-vis spectroscopy. Also, the unknown remained unchanged after refluxing in Pyridine under identical conditions.

Conversely, the unknown pigment was converted to its methyl ester and compared to an authentic sample of pyromethylpheophorbide a, obtained from pheophytin a as shown in Fig. 4 (right side).

The absorption spectra, difference spectrum (Fig. 5) of the two methyl phorbides and their 2nd and 4th derivatives (data not shown) are identical.

0.009 -

§ 2 0.007

8 12 16 2 0 ELUTION TIME [min]

Fig. 3. Elution pattern of pigments extracted from light-grown non-dividing cells of Euglena incubat-ed in darkness for 96 h. and sub­jected to high Performance liquid chromatography after acidifica­tion. The inset shows the ratios of unknown pigment to unknown plus pheophytin a in cells incu-bated in darkness for various times, which have been calculated from the relative intensities of the HPLC peaks after correction for the different extinction coefficients Ä p h e = 49.01 • g"1 • cm"1, 48 . -63.71 • g"1 • cm"1).

S. Schoch et al. • Pyropheophytin a Accompanies Pheophytin a in Darkened Light Grown Cells o f Euglena 831

Fig. 4. Chemical correlation of pyropheo­phytin a, the "unknown pigment*' isolated from dark-adapted Euglena (in box), with authentic derivatives of Chlorophyll a.

C02Me H PYROMETHYLPHEOPHORBIDE o

The two pigments also have the same R/ values on "normal" and "reverse phase" thin layer chromatog­raphy (Fig. 6) and HPLC. Finally, the mass spectra of the two methyl phorbides are also in excellent agreement (Table I). Taken together, the data show that the unknown pigment is pyropheophytin a (boxed in Fig. 4).

Pyropheophytin a is found along with pheo­phytin a in light-grown non-dividing cells of E u g l e n a incubated in darkness without shaking. Since the proportion of pyropheophytin increases with time in darkness while the propertion of pheophytin de-creases, pyropheophytin may be formed from pheo­phytin. However, since all pigments were converted to their magnesium-free forms with acid before analysis, the formation of pyrochlorophyll a as an intermediate is not excluded.

To our knowledge this is the first report of a pyrochlorophyll or pyropheophytin in an oxygenic

photosynthetic organism. Derivatives of pyrochloro­phyll are major antenna pigments in greeen sulfur bacteria [24, 25]; pyromethylpheophorbide a and its derivatives have been isolated from the excrements of various herbivores [26]. Little is known of the Steps involved in Chlorophyll degradation in photosyn-

Tablel. Mass spectrum (relative intensities in %) of the methylpheophorbide from the "Unknown Pigment" com-pared with authentic pyromethylpheophorbide a.

MS-peak Pyromethyl­ Methylpheophorbide of (m/e) pheophorbide a "Unknown Compound"

548 100 100 533 6 5 471 40 31 445 3 3 433 18 12 412 4 3 403 5 3 274 3 5 237 26 26

832 S. Schoch et al. • Pyropheophytin a Accompanies Pheophytin a in Darkened Light Grown Cells of E u g l e n a

GL

8+O.OI-

S u 0 -

- j -0 .01 • £ 0.5-

300

UNKNOWN (AFTER TRANSESTERIFICATION

WITH METHANOL)

UNKNOWN (METHYL-ESTER) MINUS PYROMETYLPHEOPHORBIDE o

PYROMETHYLPHEOPHORBIDE Q

400 500 600 WAVELENGTH (nm)

700

Fig. 5. Absorption spectra (in methanol) of pyro­methylpheophorbide a and the methylpheophor­bide prepared from the unknown pigment, as well as their difference spectrum (expanded absorption scale).

TLC:RP-C| 8 l METHANOL | r FRONT

O O*—METHYLPHEOPHORBIDE a O cZ>*—PYROMETHYLPHEOPHORBIDE a

O

1 1 jJ-ORIGIN UNKNOWN PHEOPHYTIN a STANDARDS (METHYL DERIVATIVES) Fig. 6. A comparison of the methyl phorbide prepared from the unknown pigment with methyl pheophorbide a and pyromethylpheophorbide a on a thin layer chromato-gram (C-18 reverse phase in silica, methanol as eluent).

thetic organisms [8, 9] and it is entirely possible that pheophytin a and pyropheophytin a (or pyro­chlorophyll a) serve as intermediates in such a pathway. It might be noted that the methine bridges adjacent to the reduced ring IV in chlorins are sus-ceptible to oxidative ring opening [27] especially if they bear an alkyl substituent [28-30]. One way of

creating such a Situation may be the conversion of pheophytin a (bearing a CHCOOCH3-substituent at the C-15 methine bridge) to pyropheophytin a bearing a CH2-substituent instead.

Note added in proof: We are aware or the work of O. Shimomura (FEBS Lett. 116, 203 (1981)), who recentiy suggested a bile-pigment structure derived from pyrochloro­phyll b for " C o m p o u n d F" involved in bioluminescence of an euphausid shrimp.

Acknowledgements

We thank Dr. W. Schäfer (München-Martinsried) for recording the mass spectra. The skillful tech-nical assistance (in Munich) of I. Bios (GC) and H. Wieschhoff (preparative HPLC) is acknowledged. We are indebted to Prof. H. H. Inhoffen for a generous gift of pheophytin "Sandoz". This work was supported by the National Institutes of Health (J.A.S.) the Deutsche Forschungsgemeinschaft (S.S.) and the US Department of Energy (H.W.S.).

S. Schoch et al. • Pyropheophytin a Accompanies Pheophytin a in Darkened Light Grown Cells of Euglena 833

[1] A. R. Battersby and E. McDonald, in: Porphyrins and Metalloporphyrins (K. M. Smith, ed.), p. 61, Elsevier 1975.

[2] S. Granick and S. L Beale, Adv. Enzym. 46,33 (1978). [3] L. Bogorad, in: The porphyrins (D. Dolphin, ed.),

Vol. VI, p. 125, Academic Press, New York 1979. [4] B. Frydman, R. B. Frydman, and A. Valasinas, ibid.,

p. 3. [5] R. Schmid and A. F. McDonagh, ibid., p. 258. [6] P. O'Carra, in: Porphyrins and Metalloporphyrins

(K. M . Smith, ed.), p. 123, Elsevier 1975. [7] O. T. G. Jones, in: The Porphyrins (D. Dolphin, ed.),

Vol. VI, p. 179, Academic Press, New York 1979. [8] Y. Oshioi and E. Hase, Plant Cell Physiol. 10, 41

(1969). [9] Y. Park, M. M. Morris, and G. Mackinney, J. Agric.

Food. Chem. 21,279(1973). [10] C. L. Greenblatt and J. A. Schiff, J. Protozool. 6, 23

(1959); Y. Ben-Shaul, H. T. Epstein, and J. A. Schiff, Can. J. Bot. 43,129 (1965).

[11] F. C. Pennington, H. H. Strain, W. A. Svec, and J. J. Katz, J. Am. Soc. 86,1418 (1964).

[12] A. J. Stern, J. A. Schiff, and H. T. Epstein, Plant Physiol. 39,220(1964).

[13] L. A. Kindman, C. E. Cohen, M. H. Zeldin, Y. Ben-Shaul, and J. A. Schiff, Photochem. Photobiol. 27,787 (1978).

[14] D. Cohen and J. A. Schiff, Arch. Biochem. Biophys. 177,201 (1976).

[15] J. A. Schiff, Meth. Enzymol. 21,321 (1972). [16] J. A. Schiff, H. Lyman, and G. Rüssel, Meth.

Enzymol. 23,143 (1971).

[17] V. J. Vaisberg and J. A. Schiff, Plant Physiol. 57, 260 (1976).

[18] H. Wolf and H. Scheer, Liebigs Ann. Chem. 1973, 1710.

[19] S. Schoch, U . Lempert, H. Wieschhoff, and H. Scheer, J. Chromatogr. 157,357 (1978).

[20] S. Schoch, Z. Naturforsch. 33 c, 712 (1978). [21] S. Schoch, U. Lempert, and W. Rüdiger, Z. Pflanzen-

physiol. 83,427(1977). [22] R. Calvayrac, D. Laval-Martin, G. Dubertret, and J.

L. Bomsel, Plant Physiol. 63,866 (1979). [23] C. Houssier and K. Sauer, J. Am. Chem. Soc. 92, 779

(1970). [24] A. S. Holt, in: The Chlorophylls (L. P. Veron and G.

R. Seely, eds.), p. 11, Academic Press, New York 1966.

[25] H. Brockmann, Jr., in: The Prophyrins (D. Dolphin, ed.), Vol. II, p. 288, Academic Press, New York 1978.

[26] H. Fischer and H. Orth, Die Chemie des Pyrrols, Vol. II, 2nd half, pp. 73 and 189, Akademische Ver­lagsgesellschaft, Leipzig 1940.

[27] J. A. S. Cavaleiro and K. M. Smith, J. Chem. Soc. PerkinI, 1973,2149.

[28] H. Brockmann, Jr. and C. Belter, Z. Naturforsch. 34 b, 127 (1979).

[29] R. F. Troxler and S. B. Brown, Biochemical Society Symposium Tetrapyrroles, Bristol 1980.

[30] S. B. Brown, K. M . Smith, G. M. F. Bisset, and R. F. Troxler, J. Biol. Chem. 255,8063 (1980).