The Dolastatins / Robert D. ; G.R. Pettit ; T. Nomura ; Shashi B. Mahato ; D.C. Gournelis ; H. Murray |
The Naturally Occurring Coumarins: Scope of the Review / T. Fukai ; Saraswati Garai ; G.G. Laskaris ; A. CavF |
Phenolic Constituents of Licorice (Glycyrrhiza Species): Triterpenoid Saponins |
Triterpenoid Saponins |
Progress in the Past Three Years / R. Verpoorte |
Phenolic Compounds / B. FigadTre |
Introduction |
Introduction to Tables |
Recent Methods of Structure Determination of Prenylated Phenols |
Isolation |
Cyclopeptide Alkaloids |
Biological Activities of Phenolic Constituents of Glycyrrhiza Species / A. LaurensSchemes and Tables: |
Structure Elucidation |
Biological Activity / L.A. CollettScheme 1: |
Variations of Ring-Attached Five-Carbon Units found in Coumarins |
Production of Saponins by Tissue Culture / D. Cortes |
Future Possibilities / M.T. Davies-ColemanScheme 2: |
Variations of Five-Carbon Units Attached to Carbon and Oxygen in Coumarins |
Acetogenins from Annonaceae |
Reports of New Triterpenoid Saponins |
Non-Oxygenated Coumarins / D.E.A. Rivett ; Leena A. OtsomaaTable 1: |
Naturally Occurring 6-Substituted 5,6-Dihydro-Alpha-Pyrones |
Oxygenated Coumarins / Ari M.P. KoskinenTables 2-7: |
Synthesis of 6-Deoxyamino Sugars / Tables 8-16: |
Dioxygenated Coumarins |
Introduction; Known 6-Deoxyaminohexoses |
Synthetic aspects / Tables 17-28: |
Trioxygenated Coumarins |
Tetraoxygenated Coumarins / Tables 29-34: |
Biscoumarins / Table 35: |
Triscoumarins / Table 36: |
Structure Revision Required / Table 37: |
Non-Macrocyclic Trichothecenes, Part 2 / J.F. Grove |
Cardiac GlycosidesD. Deepak / S. Srivastava ; N.K. Khare ; A. Khare |
Aspects of the Enzymology of the Shikimate Pathway / E. Haslam |
Naturally Occurring Isocyano/Isothiocyanato and Related Compounds / C. W. J. Chang |
Monoterpene Indole Alkaloids from Blue-Green Algae |
Marine Diterpenes from Sponges |
Marine Sesquiterpenes from Sponges |
Uncommon Marine Analogs |
Other Terrestrial Compounds |
Biogenesis and Biosynthesis |
Discussion and Summary |
Addendum |
Acknowledgment |
References |
Sulfur-Containing Amides from Glycosmis Species (Rutaceae) / O. Hofer ; H. Greger |
Isolation and Structure Elucidation |
Methylthiopropenoic Acid Amides |
Methylsulfinylpropenoic Acid Amides |
Methylsulfonylpropenoic Acid Amides |
Methylthiocarbonic Acid Amides |
Synthesis of Biogenic Sulfur-Containing Amides |
Biosynthesis |
Chemotaxonomy |
Appendix: Sulfur-Containing Bisamides from Aglaia Species (Meliaceae) |
List of Contributors |
Synthesis Pathways to Erythrina Alkaloids and Erythrina Type Compounds / E. Reimann |
Structural Classification of Erythrina Alkaloids / 1: |
New Erythrina Alkaloids / 3: |
Biosynthesis of Erythrina Alkaloids / 4: |
Erythrinane Alkaloids / 4.1: |
Homoerythrinane Alkaloids / 4.2: |
Syntheses of Erythrina Alkaloids and Erythrina Type Compounds / 5: |
Methodical Classification / 5.1: |
Erythrinanes / 5.2: |
Final Formation of One Ring / 5.2.1: |
Ring C (Route C) / 5.2.1.1: |
Cyclization of N-Phenethylhydroindole Derivatives (Route C(a)) / 5.2.1.1.1: |
Cyclization of Angulary Arylated Hydroindole Derivatives (Route C(b)) / 5.2.1.1.2: |
Formation of Ring B (Route B) / 5.2.1.2: |
Cyclization of N-substituted C5-Spiroisoquinoline Derivatives (Route B(a)) / 5.2.1.2.1: |
Cyclization of C6-Substituted C5-Spiroisoquinoline Derivatives (Route B(b)) / 5.2.1.2.2: |
Formation of Ring A (Route A) / 5.2.1.3: |
Cycloaddition to Pyrroloisoquinolines (Route A(a)) / 5.2.1.3.1: |
Intramolecular Aldol Condensation of Angularly Substituted Pyrroloisoquinoline (Route A(b)) / 5.2.1.3.2: |
Simultaneous Formation of More Than One Ring / 5.2.2: |
Simultaneous Formation of Rings B and C (Route B/C) / 5.2.2.1: |
Cyclization of Secondary Diphenethyl- or (Cycloalkyl)ethyl-phenethylamine Derivatives(Route B/C(a)) / 5.2.2.1.1: |
Cyclization of Tertiary Cyclohexyl-ethyl-phenethyl-amide Derivatives (Route B/C(b)) / 5.2.2.1.2: |
Cyclization of N-Substituted 1-Acyldihydroisoquinolinium Derivatives (Route A/B) / 5.2.2.2: |
Cyclization of a Highly Functionalized Homoveratrylimide (Route A/B/C) / 5.2.2.3: |
Homoerythrinanes / 5.3: |
Biomimetic Routes / 5.3.1: |
Final C Ring Formation Starting from N-Substituted Phenylhydroindoles / 5.3.2: |
A Ring Formation by [2 + 2] Photocycloaddition to Pyrrolobenzazepines / 5.3.3: |
Simultaneous B Ring Formation/C Ring Expansion Starting from Spiro-2-tetralones / 5.3.4: |
Pharmacology / 6: |
Concluding Remarks / 7: |
The Trichothecenes and Their Biosynthesis / J. F. Grove (f) |
The Trichothecenes |
Macrocyclic and Non-Macrocyclic Compounds / 2.1: |
Trichothecene Relatives / 2.2: |
Sources / 2.3: |
Oxygenation Pattern / 2.4: |
Simple Trichothecenes / 3.1: |
Mevalonic Acid to Trichodiene / 3.1.1: |
Trichodiene to 12,13-Epoxytrichothecene and Isotrichodermol / 3.1.2: |
Further Oxygenation and Esterification of the Trichothecene Nucleus: Biosynthesis of Specific Metabolites / 3.1.3: |
Trichothecolone / 3.1.3.1: |
Vomitoxin and Derivatives / 3.1.3.2: |
T-2 Toxin / 3.1.3.3: |
Nivalenol and Derivatives / 3.1.3.4: |
Trichothecene Biosynthetic Gene Clusters / 3.1.4: |
Trichoverroids and Macrocyclic Trichothecenes / 3.2: |
Melanin, Melanogenesis, and Vitiligo / S. Roy3.3: |
Melanin |
Chemistry of Melanin / 1.1: |
Isolation and Analysis |
Solubilization |
Protein Content |
Carboxylic and Phenolic Function |
Chemical Degradation / 2.5: |
Reductive Methods / 2.5.1: |
Oxidative Methods / 2.5.2: |
Pyrolytic Methods / 2.5.3: |
Spectroscopic Studies / 2.6: |
UV and IR Spectroscopy / 2.6.1: |
NMR Spectroscopy / 2.6.2: |
X-Ray Defraction Study / 2.6.3: |
ESR Study / 2.6.4: |
Structure of Melanin / 2.7: |
Melanin as Homopolymer / 2.7.1: |
Melanin as Poikilopolymer / 2.7.2: |
Melanin as Bipolymer / 2.7.3: |
Biophysical Model of Melanin Structure / 2.7.4: |
Structure of Phaeomelanin / 2.7.5: |
Synthesis of Melanin / 2.8: |
Electrochemical Synthesis / 2.8.1: |
Photochemical Synthesis / 2.8.2: |
Characteristic Biophysicochemical Properties of Melanin |
Interaction of Melanin with Light |
Melanin in UV and Visible Light |
Melanin in the Photoprotection of Skin |
Melanin as Light Screen in Eyes |
Melanin and Its Redox Function |
Binding Complexation and Medicinal Aspects of Melanin |
Use of Melanin for Defence / 3.4: |
Melanogenesis |
Melanogenesis in vivo |
Melanocytes / 4.1.1: |
The Characteristics of the Enzyme / 4.1.2: |
Regulation of Melanogenesis / 4.1.3: |
Physiological Factors / 4.1.3.1: |
Organic Sulfur Compounds / 4.1.3.2: |
Metal Ions and Other Chemicals / 4.1.3.3: |
Vitamins / 4.1.3.4: |
Hormones / 4.1.3.5: |
Neural Influence / 4.1.3.6: |
Malpighian Cells / 4.1.3.7: |
UV Light / 4.1.3.8: |
Melanogenesis in vitro |
Enzymatic Melanin Synthesis / 4.2.1: |
Rearrangement of Dopachrome / 4.2.1.1: |
Polymerization of DHI / 4.2.1.2: |
Non-Enzymatic Melanin Synthesis: Model Reaction / 4.2.2: |
Udenfriend System: A Model for Mixed Function Oxidase / 4.2.2.1: |
Melanin Formation Under Udenfriend Conditions / 4.2.2.2: |
Vitiligo |
Melanocytotoxicity: Antimelanocyte-Antibodies Formation |
The Immune Hypothesis |
The Neural Hypothesis |
The Self-Destruction Hypothesis / 5.2.3: |
The Composite Hypothesis / 5.2.4: |
Chemotherapy of Vitiligo |
Psoralens |
Psoralen Action and UV Light |
Psoralen Action on Melanogenesis |
Abnormal Biochemical Parameters in Vitiligo / 5.4: |
Status of Tryptophan in the Melanogenic System / 5.5: |
A Composite Hypothesis on Vitiligo / 5.6: |
Author Index |
Subject Index |
List of Contributor |
Pyrroles from Vertebrates / 1.: |
Pyrroles from Invertebrates / 3.: |
Pyrroles from Insects / 3.1.: |
Pyrroles from Ants / 3.1.1.: |
Pyrroles from Beetles / 3.1.2.: |
Pyrrole Pheromones from Butterflies / 3.1.3.: |
Pyrroles from Sponges / 3.2.: |
Pyrrole-2-Carboxylates from Sponges / 3.2.1.: |
Pyrrole-2-Carboxamides from Sponges / 3.2.2.: |
Pyrrole-2-Carboxamides of the Oroidin Type / 3.2.2.1.: |
Cyclized Oroidin Metabolites / 3.2.2.2.: |
Dimeric Oroidin Metabolites / 3.2.2.3.: |
Alkyl Pyrroles from Sponges / 3.2.3.: |
Aryl Pyrroles from Sponges / 3.2.4.: |
Hydroxy Pyrroles from Sponges / 3.2.5.: |
Tetramic Acid Derivatives from Sponges / 3.2.6.: |
Pyrroles from Other Invertebrates / 3.3.: |
Aryl Pyrroles / 3.3.1.: |
Other Pyrrole Derivatives / 3.3.2.: |
Pyrroles from Protozoa / 3.4.: |
Pyrroles from Plants / 4.: |
Dihydropyrrolizine Derivatives / 4.1.: |
Pyrrole-2-Carboxylic Acid Derivatives from Plants / 4.2.: |
Pyrrolinone Derivatives in Plants / 4.3.: |
Pyrroles from Fungi / 5.: |
Pyrroles from Basidiomycetes / 5.1.: |
Pyrroles from Deuteromycetes / 5.2.: |
Pyrroles from Myxomycetes / 5.3.: |
Pyrrolinone Derivatives in Fungi / 5.4.: |
Tetramic Acid Derivatives in Fungi / 5.5.: |
Pyrroles from Bacteria / 6.: |
Halogenated Monopyrroles from Bacteria / 6.1.: |
Halogenated Benzylpyrroles / 6.1.1.: |
Halogenated Benzoylpyrroles / 6.1.2.: |
Halogenated [alpha]-Arylpyrroles / 6.1.3.: |
Halogenated [beta]-Arylpyrroles / 6.1.4.: |
Pyrrole-2-carboxylates from Bacteria / 6.2.: |
Pyrrole-2-carboxamides from Bacteria / 6.3.: |
The Distamycin Group / 6.3.1.: |
Pyrrol-2-carbacyl Derivatives from Bacteria / 6.4.: |
[alpha]-Pyridylpyrroles from Bacteria / 6.5.: |
Other Monopyrrole Derivatives from Bacteria / 6.6.: |
Prodigiosins / 6.7.: |
Prodigiosins from Eubacteria / 6.7.1.: |
Prodiginines from Actinomycetes / 6.7.2.: |
Hydroxy Pyrroles from Bacteria / 6.8.: |
Tetramic Acid Derivatives from Prokaryotes / 6.9.: |
Derivatives of 3-Acetyltetramic Acid from Actinomycetes / 6.10.: |
Synthetic Aspects of Iridoid Chemistry / H. Franzyk |
Classification of Iridoids |
Availability and Production of Iridoids |
Semi-Synthetic Conversions Between Iridoids |
Monoterpene Alkaloids Structurally Related to Iridoids |
Syntheses from Iridoids; References |
The Defensive Chemistry of Ants / S. Leclercq ; J. C. Braekman ; D. Daloze ; J. M. Pasteels |
Introduction; Alkaloids |
Nonalkaloidal Compounds |
Naturally Occurring Plant Coumarins / R.D.H. Murray |
Artemisinin: An Endoperoxidic Antimalarial from Artemisia annua L / H. Ziffer ; R.J. Highet ; D.L. Klayman |
Marine Glycolipids / E. Fattorusso ; A. Mangoni |
Brassinosteroids / G. Adam ; J. Schmidt ; B. Schneider |
Natural Occurrence and Distribution |
Structures |
Isolation and Purification |
Analysis of Brassinosteroids |
Synthesis; Biosynthesis |
Metabolism of Brassinosteroids |
Physiological Action |
Molecular Mode of Action |
Conclusions |
Chemistry of the Neem Tree (//Azadirachta indica//A. Juss.) / A. Akhila ; K. Rani |
Introduction; Chemistry of Limonoids; C-Seco Meliacins; Other Compounds |
Secondary Metabolites and the Control of Some Blue Stain and Decay Fungi / W. A. Ayer ; L. S. Trifonov |
Introduction; Blue Stain Fungi |
Decay Causing Fungi |
The Black Gall Effect |
Condensed Tannins / D. Ferreira ; E. V. Brandt ; J. Coetzee ; E. Malan |
Introduction; Formation of the Interflavanyl Bond in Oligomeric Proanthocyanidins |
Cleavage of the Interflavanyl Bond in Oligomeric Proanthocyanidins |
Rearrangement of the Pyran Heterocycle of Oligomeric Proanthocyanidins |
Conformational Analysis of Dimeric Proanthocyanidins |
Conclusion |
Constituents of //Lactarius// (Mushrooms) / W. M. Daniewski ; G. Vidari |
Introduction; Sesquiterpenes Isolated from //Lactarius//; Introduction to Parts 6 and 7 - Velutinal Esters and Related Sesquiterpenes |
Chemistry of Sesquiterpenes of //Lactarius// |
Nitric Oxide: Physiological Roles, Biosynthesis and Medical Uses / D. R. Adams ; M. Brochwicz-Lewinski ; A. R. Butler |
Discovery in the Vasculature |
Platelet Aggregation |
NO and the Immune System |
NO and the Nervous System |
S-Nitrosothiols |
NO Activity in the Mammalian Eye |
The NO Biosynthetic Pathway |
Mechanism of the Nitric Oxide Synthase-Catalysed Reaction |
Nitric Oxide Synthase Structure |
Clinical Uses of NO and Its Inhibitors |
Acknowledgements |
Microbial Siderophores / Herbert Budzikiewicz |
Peptide Siderophores |
Pyoverdins and Related Siderophores from Pseudomonas Spp |
Azomonas and Azotobacter Siderophores |
Anachelin |
Actinomycetal Metabolites |
Bacterial Hydroxamate Siderophores |
Fungal L-Ornithine-Based Hydroxamate Siderophores |
Catecholate Siderophores |
Lipopeptidic Siderophores |
Pseudomonas mendocina Siderophores / 2.9: |
Siderophores Based on Diamino- and Triaminoalkane Skeletons |
Rhizobactin |
Hydroxamic Acid Siderophores |
Citrate Siderophores |
Siderophores with Two Hydroxamic Acid Units |
Siderophores with 2-Oxoglutaric Acid Units |
Siderophores with Two Catecholate Units / 4.3: |
Siderophores with Two Citric Acid Units / 4.4: |
Legiobactin / 4.5: |
Pyochelin and Related Structures |
Miscellaneous Siderophores |
Selected Syntheses / 8: |
Anachelin H / 8.1: |
Alterobactin / 8.2: |
Parabactin / 8.3: |
Nannochelin A / 8.4: |
Pyochelin / 8.5: |
Epilog / 9: |
Appendix |
Notes Added in Proof |
Resin Glycosides from the Morning Glory Family / Rogelio Pereda-Miranda ; Daniel Rosas-RamÃrez ; Jhon Castañeda-Gómez |
Ethnobotanical Background and Discovery |
Structural Diversity |
Chemical Composition |
Resin Glycosides |
Isolation Techniques |
Structure Elucidation of Resin Glycosides |
Degradative Chemical Methods |
Spectroscopic Methods |
Crystallographic Methods |
Molecular Modeling |
Strategies for Synthesis |
Tricolorin A / 6.1: |
Ipomoeassin E / 6.2: |
Woodrosin I / 6.3: |
Significance |
Traditional Medicine and Morning Glories / 7.1: |
Biological Activities / 7.2: |
Pharmacology and Toxicology / 7.3: |
Chemical Ecology / 7.4: |
Chlorophyll Catabolites / B. Krautler |
Chlorophyll Catabolites from Vascular Plants |
Green Chlorophyll Degradation Products in Vascular Plants |
Chlorophyllide a and b from Chlorophylls by Loss of the Phytol Side Chain / 2.1.1: |
Reductive Path from b- to a-Type Chlorophyll(ide)s / 2.1.2: |
Pheophorbide a from Chlorophyllide a by Removal of the Magnesium Ion / 2.1.3: |
13[superscript 2]-Carboxy-pyropheophorbide a from Hydrolysis and Pyropheophorbide a from Overall Loss of the Methoxycarbonyl Group from Pheophorbide a / 2.1.4: |
Non-green Chlorophyll Degradation Products from Vascular Plants |
Discovery and Structure Analysis of Fluorescent Chlorophyll Catabolites / 2.2.1: |
Preparation of the Elusive Red Chlorophyll Catabolite by Partial Synthesis / 2.2.2: |
An Enzyme-bound Red Chlorophyll Catabolite from Enzymatic Oxygenation of Pheophorbide a / 2.2.3: |
Fluorescent Chlorophyll Catabolites from Enzymatic Reduction of the Red Chlorophyll Catabolite / 2.2.4: |
Model Experiments for the Reduction of the Red Chlorophyll Catabolite to Fluorescent Chlorophyll Catabolites / 2.2.5: |
Non-fluorescent Colourless Chlorophyll Catabolites / 2.2.6: |
A Non-enzymatic Tautomerization Achieves the "Final" Transformation of Fluorescent Chlorophyll Catabolites to Non-fluorescent Colourless Chlorophyll Catabolites / 2.2.7: |
Peripheral Functional Groups and Conjugations Found in Non-fluorescent Colourless Chlorophyll Catabolites / 2.2.8: |
Evidence for Further Breakdown of the Non-fluorescent Colourless Chlorophyll Catabolites in Higher Plants / 2.2.9: |
Chlorophyll Catabolites from the Green Alga Chlorella protothecoides |
Chlorophyll Catabolites from Marine Organisms |
Conclusions and Outlook |
Steroidal Saponins / N. P. Sahu ; S. Banerjee ; N. B. Mondal ; D. Mandal |
Conventional Methods |
Spectrometry Coupled with Chemical Methods |
Modern Spectrometric Methods |
Mass Spectrometry / 3.3.1: |
[superscript 1]H NMR Spectroscopy / 3.3.2: |
[superscript 13]C NMR Spectroscopy / 3.3.2.2: |
2D NMR Spectroscopy / 3.3.2.3: |
Cytotoxic Activity Against Cancer Cell Lines |
Antifungal Activity |
Miscellaneous Effects |
Biosynthesis of Steroidal Glycosides |
Report of New Steroidal Saponins (1998-Mid-2006) |
Acknowledgement |
Non-conventional Lignans: Coumarinolignans, Flavonolignans, and Stilbenolignans / Sajeli A. Begum ; Mahendra Sahai ; Anil B. Ray |
Coumarinolignans |
Occurrence of Coumarinolignans |
Classification of Coumarinolignans |
Structure Elucidation of Coumarinolignans |
Chemistry of Coumarinolignans |
Biological Activity of Coumarinolignans |
Biogenesis of Coumarinolignans |
Flavonolignans |
Occurrence of Flavonolignans |
Features of Flavonolignans and Their Classification |
Structure Elucidation of Flavonolignans |
Chemistry of Flavonolignans |
Biological Activity of Flavonolignans / 3.5: |
Biogenesis of Flavonolignans / 3.6: |
Stilbenolignans |
Occurrence and Features of Stilbenolignans |
Structure Elucidation and Synthesis of Stilbenolignans |
Biological Activity of Stilbenolignans |
Biogenesis of Stilbenolignans |
Picrotoxanes / Edda Gössinger |
Tabular Overview of the Picrotoxanes |
Occurrence |
Systematic and Geographic Occurrence of Picrotoxane-Containing Plants |
Parasitic Plants |
Picrotoxanes Found in Animals and Animal Products |
The Riddle of the Scattered Taxonomic Occurrence of Picrotoxanes |
Isolation of Picrotoxanes |
Examples of Recent Isolation Procedures |
Structure Determination of Picrotoxanes |
Main Picrotoxanes of the Menispermaceae |
Main Picrotoxanes of the Coriariaceae |
Picrotoxanes Isolated from Toxic Honey |
Picrotoxanes of the Picrodendraceae |
Picrotoxanes from Dendrobium Species |
Total Syntheses of Picrotoxanes |
Overview |
Description of the Syntheses |
Biosynthesis of Picrotoxanes |
Investigations on the Biosynthesis of Dendrobines |
Investigations on the Biosynthesis of Sesquiterpene Picrotoxanes |
Physiological Activity of Picrotoxanes |
Toxicity |
Picrotoxanes as Therapeutics |
Picrotoxanes as Epileptogenic Compounds |
Picrotoxanes as Tools in Neurobiological Research |
Abbreviations |
Combinatorial and Synthetic Biosynthesis in Actinomycetes / Marta Luzhetska ; Johannes Härle ; Andreas Bechthold |
Combinatorial Biosynthesis and Synthetic Biosynthesis |
Achievements in Combinatorial Biosynthesis |
Challenges for Combinatorial Biosynthesis |
Synthetic Biosynthesis |