Progress in the Chemist17 of Organie Natural Produets

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2 Fortsehritte der Chemie organiseher Naturstoffe Progress in the Chemist17 of Organie Natural Produets 53 Founded b~ L. Zeehmeister Edited b~ W. Berz, B. Grisebaeh, G. W. Kirb~, and Ch.Tamm Authors: L.F. Alves, A. Chimia., M.J. Milews.,., T. Nomllf''' Springer-Verlag Men New York 1988

3 Dr. W. HERZ, Professor of Chemistry, Department of Chemistry, The Florida State University, Tallahassee, Florida, U.S.A. Prof. Dr. H. GRISEBACH, Biologisches Institut II, Lehrstuhl fur Biochemie der Pflanzen, Albert-Ludwigs-Universitat, Freiburg i.br., Federal Republic of Germany G.W. KIRBY, Sc. D., Regius Professor of Chemistry, Chemistry Department, The University, Glasgow, Scotland Prof. Dr. CH. TAMM, Institut fur Organische Chemie der Universitat Basel, Basel, Switzerland With 72 Figures This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically those of translation, reprinting, re-use of illustrations, broadcasting, reproduction by photocopying machine or similar means, and storage in data banks by Springer-VerlagjWien Softcover reprint of the hardcover 1 st edition 1988 Library of Congress Catalog Card Number AC ISSN ISBN-13 : e-isbn-13: DOl: /

4 list of Contributors Contents Chemical Ecology and the Social Behavior of Animals. By L.F. ALVES. VIII 1. Introduction 1 2. Terminology Origin Pheromones as a Multicomponent System 9 5. Perception of Pheromones by Insects and Vertebrates Chemical Communication in Vertebrates Endocrine Hormone-Pheromone Interaction Bruce Effect Whitten Effect Lee-Boot Effect Ropartz-Effect Maternal Pheromones Chemical Communication in Marine Organisms The Effect of Anosmia Chemical Communication in Invertebrates Caste and Kin Recognition in Social Insects Insect Sex Pheromones Role of Pheromones in Reproductive Isolation of Insects Arthropod Defensive Secretions Defense in Termites Predator-Prey Interactions Human Pheromones Conclusion 55 Acknowledgements 55 References 56 Phenolic Compounds of the Mulberry Tree and Related Plants. By T. NOMURA 87 I. Introduction II. Flavonoids Carrying Isoprenoid Substituents Isolated from the Japanese Cultivated Mulberry Tree Isolation of Flavonoids Carrying Isoprenoid Substituents Structures of Flavonoids Carrying Isoprenoid Substituents Synthesis of Tetrahydrokuwanon C Tetramethyl Ether 99 III. Photo-Oxidative Cyc1ization of Prenylflavones Photo-Oxidative Cyc1ization of Morusin Mechanism of the Photo-Oxidative Cyc1ization of Morusin Oxidative Cyc1ization of Morusin

5 VI Contents IV. Phytoalexins and Antifungal Substances in the Mulberry Tree 109 V. Diels-Alder Type Adducts of the Cultivated Mulberry Tree Hypotensive Constituents, Kuwanons G and H Five Novel 2-Arylbenzofuran Derivatives, Cha1comoracin, Mulberrofurans C, F, G, and H Coloring Matter of Morus Root Bark, Mulberrofuran I Other Phenolic Compounds Related to Mulberrofuran I Diels-Alder Type Adducts of Morus Cell Cultures Other Diels-Alder Type Adducts of Cultivated Mulberry Tree 147 VI. Phenolic Constituents of the Crude Drug" Sang-Bai-Pi" Structures of the Flavonoids Carrying Isoprenoid Substituents Isolated from "Sang-Bai-Pi" Structures of Diels-Alder Type Adducts of" Sang-Bai-Pi" 154 VII. Absolute Configuration of Diels-Alder Type Adducts from Morus Sp Classification of Diels-Alder Type Adducts Stereochemistry of Diels-Alder Type Adducts Absolute Configuration of Mulberrofurans C and J by CD Spectra Absolute Configuration of Other Diels-Alder Type Adducts Absolute Configuration of the Chiral Centers on the Cyclohexene Ring of Kuwanon L Absolute Configuration of the Ketal Compounds, Mulberrofurans F, G, and K VIII. Phenolic Constituents of Cudrania tricuspidata (Carr.) Bur. and Broussonetia Sp Structures of Xanthone and Flavonoid Derivatives from Cudrania tricuspidata (Carr.) Bur Structures of 1,3-Diphenylpropane and Flavonoid Derivatives from Broussonetia Sp IX. Biological Activities of Phenolic Constituents of Mulberry Tree and Related Plants Acknowledgements 191 References 191 N-Hydroxyamino Acids and Their Derivatives. By A. CHIMIAK and M.J. MILEWSKA 203 I. Introduction, Scope and Nomenclature II. N-Hydroxyamino Acid Residues as Fragments of Natural Products 206 III. Physical and Chemical Properties 213 IV. Analysis 215 V. Naturally-Occurring N-Hydroxypeptides 217 VI. Biological Action of N-Hydroxyamino Acids and N-Hydroxypeptides 217 VII. Biogenesis of the N-Hydroxyamide Bond VIII. Synthesis of N-Hydroxyamino Acids and Their Derivatives 1. Reaction of Nitric Oxide with 1,3-Diketo Derivatives 2. Strecker Synthesis Reduction of Nitro Acids and Nitro Esters

6 Contents VII 4. Reduction of Oximes of a-keto Acids and Substituted Aldoximes Addition of Hydroxylamine to a,~-unsaturated Acids Reaction of a-halo Acids with Hydroxylamine Reaction of a-halo Acids with Benzyloxyamine From N-Tosyl-O-Benzylhydroxylamine From Nitrones Substitution Addition From Oxaziridines Alkylation of Hydroxamic Acids Synthesis of N-Hydroxy-sec-amino Acids Esterification of N-Hydroxyamino Acids and N-Alkoxyamino Acids 245 IX. Synthesis of N-Hydroxypeptides N-Hydroxydiketopiperazines Linear N-Hydroxypeptides. 260 X. Reactions of N-Hydroxypeptides 264 XI. Final Remarks Addendum 265 Acknowledgements 266 References 266 Author Index 279 SUbject Index 294

7 List of Contributors ALVES, Dr. L.F., Rua das Marrecas 38, sala 302, CEP Lapa, Rio de Janeiro, Brazil. CHlMIAK, Prof. A., Institute of Organic and Food Chemistry and Technology, Technical University, Majakowskiego 11/12, Gdansk, Poland. MILEWSKA, Dr. M.J., Institute of Organic and Food Chemistry and Technology, Technical University, Majakowskiego 11/12, Gdansk, Poland. NOMURA, Prof. T., Ph.D., Faculty of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba, 274, Japan.