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

196 Pages·1991·6.137 MB·English

by  Dr. J. Asselineau, Professor J. Kagan (auth.)

FortsehriHe der Chemie organiseher Naturstoffe
Progress in the Chemist17
of Organie Natural Produets
S6
Founded .. L. Zeehmeister
~
Edited ..~ W. Rerz, R. Grise"aeh t, G. W. Kir. .~ ,
and Ch.Tamm
Authors:
J. Asselineau, J. Kagan
Springer-Verlag
WieaNewYor" JqqJ
Dr. W. HERZ, Professor of Chemistry, Department of Chemistry,
The Florida State University, Tallahassee, Florida, U.S.A.
G. W. KIRBY, Sc. D., Regius Professor of Chemistry, Chemistry Department,
The University, Glasgow, Scotland
Prof. Dr. CH. TAMM, Institut fur Organische Chemie der Universitiit Basel,
Basel, Switzerland
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
machines or similar means, and storage in data banks.
© 1991 by Springer-Verlag/Wien
Softcover reprint of the hardcover 1st edition 1991
Library of Congress Catalog Card Number AC 39-1015
Typesetting: Macmillan India Ltd., Bangalore-25
With 8 Figures
ISBN-13: 978-3-7091-9086-9 e-ISBN-13: 978-3-7091-9084-5
DOl: 10.1007/978-3-7091-9084-5
We deeply regret the death on March 29, 1990 of our fellow
editor and friend Hans Grisebach. He was associated with our
series since 1969 and contributed in no small measure to its
continuing success. We shall miss his suggestions and advice.
W. Herz, Tallahassee
G. W. Kirby, Glasgow
Ch. Tamm, Basel
Contents
List of Contributors. . . . . . . . . . . . . . . . . . . . . . . . X
Bacterial Lipids Containing Amino Acids or Peptides Linked by Amide Bonds.
By J. ASSELINEAU .
I. Introduction. . . 2
II. N-Acylamino Acids 3
1. N-Acyl-L-serine . 3
1.1. Serratamolide . 3
1.2. Flavolipin . . 6
2. N-Acyl-L-ornithine. 6
2.1. Ornithine-containing Lipid 6
2.2. Cerilipin. . . 14
3. Mass Spectrometry. 15
4. Biological Properties 18
III. N-Acylpeptides. . . 18
1. N-Acylpeptides with a Linear Peptide Moiety 19
1.1. N-Acyldipeptides:Majusculamides A and B 19
1.2. N-Acyltetrapeptides from Rhodococcus erythropolis . 21
1.3. N-Acylpentapeptides from Mycobacterium paratuberculosis 21
1.4. N-Acyloctapeptide: Stenothricin 23
1.5. N-Acylnonapeptide: Fortuitin . . . 23
1.6. N-Acyldecapeptides: Cerexins . . . 24
1.7. N-Acyltrid\~,apeptides: Tridecapeptins 26
1.8. N-Acylund",·,'peptide: Amphomycin . 27
2. N-Acylpeptides Containing a Hydroxy Fatty Acid Involved in a Lactone
Ring. . . . . . . . . . . . . . . . . . . . . . .. 28
2.1. N-Acylpentapeptide: Globomycin. . . . . . . . . . ., 28
2.2. N-Acylheptapeptides: Surfactin, Esperin and Related Compounds. 30
2.3. N-Acylheptapeptides: Peptidolipin NA . . . . . . . . 33
3. N-Acylpeptides with a Lactone Ring not Involving the Hydroxyl
Group of a Hydroxy Fatty Acid 35
3.1. N-Acyloctapeptides . 35
3.1.1. Lipopeptins 35
3.1.2. Neopeptins. . 37
3.2. N-Acylnonapeptide: Visco sin. 40
3.3. N-Acyldecapeptides: Imacidines. 41
3.4. N-Acyltridecapeptides: Antibiotic A21978 C 43
3.5. N-Acyltetradecapeptide: Stendomycin 44
Vlll Contents
4. Peptidolipids with a Lactam Ring 48
4.1. Iturins . . . 48
4.2. Bacillomycins. . . . . . 50
4.3. Mycosubtilin . . . . . . 52
4.4. General Comments on the Peptidolipids of the Iturin Group 53
4.5. Cyclic Peptides: Octapeptins. . . 53
4.6. Cyclic Peptides: Antibiotic EM 49. 54
5. Mass Spectrometry of N-Acylpeptides . 54
6. Biological Properties of Peptidolipids . 57
IV. Glycosides of Peptidolipids. . . . . . 59
1. Glycosides of Peptidolipids Isolated from Rhodococcus erythropolis. 59
2. Glycoside of N-Acylnonapeptide: Herbicolin A . 59
3. Mycosides C and Related Antigenic Compounds . . 61
3.1. Apolar Mycosides C . . . . . . . . . . 61
3.2. Polar Mycosides C: Antigenic Glycopeptidolipids 67
3.3. Mycosides C as Receptors for Mycobacteriophages. 70
V. Conclusion . 71
Acknowledgements 73
Addendum 73
References 73
Naturally Occurring Di-and Trithiophenes. By J. KAGAN . 87
I. Introduction . 88
II. Nomenclature 88
III. Naturally Occurring Dithiophenes: Structures 89
IV. Distribution of Dithiophenes . . . . . . 89
V. Naturally Occurring Trithiophenes: Structures 95
VI. Distribution of Trithiophenes. . . 95
VII. Biosynthesis of Di-and Trithiophenes 99
VIII. Synthesis of Di-and Trithiophenes 112
IX. Photophysical Studies. . 121
X. Photochemical Reactions 128
XI. Biological Reactions . 130
1. Effect on DNA . . 130
2. Antiviral Properties 130
3. Effect on Skin 132
4. Effect on Erythrocytes. 134
5. Phototoxicity Toward Bacteria and Fungi 135
6. Nematocidal Activity. . . 141
7. Trithiophenes as Insecticides . . . . . 144
Contents IX
8. Toxicity Toward Fish and Other Aquatic Organisms. 151
9. Toxicity of ex-Terthienyl Toward Plants 154
XII. Conclusion 155
Acknowledgement 155
References . 156
Author Index 171
Suhject Index 179
List of Contributors
ASSELINEAU, Dr. J., Centre de Recherche de Biochimie et Genetique Cellulaire, Universite
Paul Sabatier, 118 Route de Narbonne, F-31062 Toulouse, France.
KAGAN, Professor 1., University of Illinois at Chicago, Department of Chemistry (M/C
111), P. O. Box 4348, Chicago, IL 60680, U.S.A.
Bacterial Lipids Containing Amino Acids or Peptides
Linked by Amide Bonds
J. ASSELINEAU, Centre de Recherche de Biochimie et Genetique
Cellulaires, Toulouse, France
With 6 Figures
Contents
I. Introduction. . . 2
II. N-Acylamino Acids 3
1. N-Acyl-L-serine . 3
1.1. Serratamolide . 3
1.2. Fla volipin . . . 6
2. N-Acyl-L-ornithine. . 6
2.1. Ornithine-containing Lipid 6
2.2. Cerilipin. . . 14
3. Mass Spectrometry. 15
4. Biological Properties 18
III. N-Acylpeptides. . . 18
1. N-Acylpeptides with a Linear Peptide Moiety 19
1.1. N-Acyldipeptides: Majusculamides A and B 19
1.2. N-Acyltetrapeptides from Rhodococcus erythropolis . 21
1.3. N-Acylpentapeptides from Mycobacterium paratuberculosis 21
1.4. N-Acyloctapeptide: Stenothricin 23
1.5. N-Acylnonapeptide: Fortuitin . . . 23
1.6. N-Acyldecapeptides: Cerexins . . . 24
1.7. N-Acyltridecapeptides: Tridecapeptins 26
1.8. N-Acylundecapeptide: Amphomycin . 27
2. N-Acylpeptides Containing a Hydroxy Fatty Acid Involved in a Lactone
Ring. . . . . . . . . . . . . . . . . . . . . . .. 28
2.1. N-Acylpentapeptide: Globomycin. . . . . . . . . . .. 28
2.2. N-Acylheptapeptides: Surfactin, Esperin and Related Compounds. 30
2.3. N-Acylheptapeptides: Peptidolipin NA . . . . . . . . 33
3. N-Acylpeptides with a Lactone Ring not Involving the Hydroxyl
Group of a Hydroxy Fatty Acid . 35
3.1. N-Acyloctapeptides. . . . . . . . . . . . . . . 35
2 1. ASSELINEAU
3.1.1. Lipopeptins . . . . 35
3.1.2. Neopeptins. . . . . 37
3.2. N-Acylnonapeptide: Viscosin. 40
3.3. N-Acyldecapeptides: Imacidines. 41
3.4. N-Acyltridecapeptides: Antibiotic A21978 C 43
3.5. N-Acyltetradecapeptide: Stendomycin ·44
4. Peptidolipids with a Lactam Ring 48
4.1. Iturins . . . 48
4.2. Bacillomycins. . . . . . 50
4.3. Mycosubtilin . . . . . . 52
4.4. General Comments on the Peptidolipids of the Iturin Group 53
4.5. Cyclic Peptides: Octapeptins. . . 53
4.6. Cyclic Pep tides: Antibiotic EM 49. 54
5. Mass Spectrometry of N-Acylpeptides . 54
6. Biological Properties of Peptidolipids . 57
IV. Glycosides of Peptidolipids. . . . . . 59
1. Glycosides of Peptidolipids Isolated from Rhodococcus erythropolis. 59
2. Glycoside of N-Acylnonapeptide: Herbicolin A . 59
3. Mycosides C and Related Antigenic Compounds . . 61
3.1. Apolar Mycosides C . . . . . . . . . . 61
3.2. Polar Mycosides C: Antigenic Glycopeptidolipids 67
3.3. Mycosides C as Receptors for Mycobacteriophages. 70
V. Conclusion . 71
Acknowledgements 73
Addendum 73
References 73
I. Introduction
For a long time, amino acid or peptide contammg lipids were
considered as unusual components of bacteria. Isolation was mainly
confined to "Ii po-amino acids" which appeared to be transitory inter
mediates in cellular metabolism. Not much progress has been made on
their metabolism.
More recently, thanks to improvements in fractionation and analyt
ical techniques and because of the increase of interest in bacterial
metabolites, particularly metabolites exhibiting antibiotic or enzyme
inhibiting properties, many new peptidolipids have been discovered.
Whereas in the currently known cases pep tides are always linked to
fatty material by amide bonds, the amino acids in peptidolipids may be
linked through amide or through ester bonds. The present review will be
limited to compounds containing amide bonds. In the case of peptido
lipids, an arbitrary limitation has been introduced: Only compounds