Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

The volumes in this classic series, now referred to simply as "Zechmeister" after its founder, L. Zechmeister, have appeared under the Springer Imprint ever since the series' inauguration in 1938. The volumes contain contributions on various topics relate

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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

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. © 1988 by Springer-VerlagjWien Softcover reprint of the hardcover 1st edition 1988

Library of Congress Catalog Card Number AC 39-1015

ISSN 0071-7886

ISBN-13 :978-3-7091-8989-4 e-ISBN-13:978-3-7091-8987-0 DOl: 10.1007/978-3-7091-8987-0

Contents list of Contributors

. VIII

Chemical Ecology and the Social Behavior of Animals. By L.F. ALVES

1. 2. 3. 4. 5. 6. 7.

8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19.

Introduction Terminology . . . . . . . . . . . . . Origin . . . . . . . . . . . . . . . Pheromones as a Multicomponent System Perception of Pheromones by Insects and Vertebrates Chemical Communication in Vertebrates Endocrine Hormone-Pheromone Interaction 7.1 Bruce Effect 7.2 Whitten Effect 7.3 Lee-Boot Effect 7.4 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

1 2 6 9 11 15 20 22 23 23 24 24 24 29 29 30 33 35 39 42 48 52 55

Acknowledgements

55

References

56

Phenolic Compounds of the Mulberry Tree and Related Plants. By T.

NOMURA

I. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . II. Flavonoids Carrying Isoprenoid Substituents Isolated from the Japanese Cultivated Mulberry Tree . . . . . . . . . . . . . . . . . 1. Isolation of Flavonoids Carrying Isoprenoid Substituents . 2. Structures of Flavonoids Carrying Isoprenoid Substituents 3. Synthesis of Tetrahydrokuwanon C Tetramethyl Ether III. Photo-Oxidative Cyc1ization of Prenylflavones 1. Photo-Oxidative Cyc1ization of Morusin . . . . . . 2. Mechanism of the Photo-Oxidative Cyc1ization of Morusin 3. Oxidative Cyc1ization of Morusin . . . . . . . . . . .

87

88 92 92 92 99 102 102 104 106

Contents

VI

IV. Phytoalexins and Antifungal Substances in the Mulberry Tree V. D