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Identification of Lichen Substances PDF

498 Pages·1996·26.554 MB·English
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Siegfried Huneck and Isao Yoshimura Identification of Lichen Substances Springer Berlin Heidelberg New York Barcelona Budapest Hong Kong London Milan Paris Santa Clara Singapore Tokyo Siegfried Huneck Isao Yoshimura Identification of Lichen Substances With 67 Figures Springer Dr. SIEGFRIED HUNECK Fliederweg 34a 06179 Langenbogen/Saalkreis Germany Professor Dr. ISAo YOSHIMURA Kochi Gakuen College 292 Asahitenjincho Kochi 780 Japan Cover photo by courtesy of Roman Turk. Photo showing various Lecidea and Porpidia species on gneiss. Formula: (+ )-Rhizocarpic acid ISBN-13:978-3-642-8S24S-9 Library of Congress Cataloging-in-Publication Data Huneck, S. (Siegfried), 1928- Identification of lichen substances / S. Huneck, I. Yoshimura. P. cm. Includes bibliographical references (p. ) and index. ISBN-13:978-3-642-85245-9 e-ISBN-13:978-3-642-85243-5 DOl: 10.1007/978-3-642-85243-5 1. Lichen products-Handbooks, manuals, etc. 2. Lichens Analysis-Handbooks, manuals, etc. I. Yoshimura, l. (Isao) II. Title. QK581.H86 1996 S89.1-dc20 96-3927 The material is concerned, specifically the rights of translation, reprinting reuse of illustrations, recitation, broadcasting, reproduction on microfilm or in any other way, and storage in data banks. Duplication of this publication or parts thereof is permitted only under the provisions of the German Copyright Law of September 9, 1965, in its current version, and permissions for use must always be obtained from Springer-Verlag. Violations are liable for prosecution under the German Copyright Law. © Springer-Verlag Berlin Heidelberg ~996 Softcover reprint of the hardcover 1st edition 1996 Product Liability: The publisher can give no guarantee for information about drug dosage and application thereof contained in this book. In every individual case the respective user must check its accuracy by consulting other pharmaceutical literature. The use of general descriptive names, registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. Typesetting: Best-set Typesetters Ltd., Hong Kong Cover design: Meta Design, Berlin SPIN 1006312331/3137 - 5432 1 0 - Printed on acid-free paper Dedicated to our friends John A. Elix, Benno Feige, Wolfgang Steglich and Raffaele Tabacchi Acknowledgments We are grateful to Prof. Dr. J.A. Elix (Canberra), Prof. Dr. C. Leuckert (Berlin), Prof. Dr. R. Tabacchi (Neuchatel) and Dr. P.A. Cohen (Vancouver) for providing reprints and unpublished data, and to Dr. H.T. Lumbsch (Essen) for checking the names of the lichens. S. Huneck thanks his wife Ruth for manifold help in preparing the manuscript and the Fonds der Chemischen Industrie (Frankfurt/Main) for financial support. S. HUNECK 1. YOSHIMURA Contents 1 Introduction. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 1.1 Short History of the Study of Lichen Substances. . . . . . . . 1 1.2 General Meaning of Lichen Substances and Their Use in Past and Present Time. . . . . . . . . . . . . . 3 1.2.1 Biological Activities of Lichen Substances. . . . . . . . . . . . 3 1.2.2 Use of Lichens in Folk Medicine. . . . . . . . . . . . . . . . . . . 4 1.2.3 Lichens as Raw Material for Dyes . . . . . . . . . . . . . . . . . . 5 1.2.4 Lichens as Basic Material for Perfume. . . . . . . . . . . . . . . 5 1.2.5 The Biological Meaning of Lichen Substances. . . . . . . . . 5 1.2.6 Lichens as Biomonitors . . . . . . . . . . . . . . . . . . . . . . . . . 6 1.2.7 Lichens as Biodeterioration . . . . . . . . . . . . . . . . . . . . . . 6 1.2.8 Chemotaxonomy of Lichens ..................... 6 1.3 Cultur~ of Lichens and Their Symbionts . . . . . . . . . . . . . . 9 2 Identification of Lichen Substances. . . . . . . . . . . . . . . . . . 11 2.1 Extraction and Purification of Lichen Substances. . . . . . . 11 2.2 Melting Point. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13 2.3 Colour Reactions and Other Reactions for the Identification of Lichen Substances. . . . . . . . . . . . 13 2.4 UV Spectroscopy. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15 2.4.1 Depsides......................................... 17 2.4.2 Depsidones....................................... 17 2.4.3 y-Lactones....................................... 17 2.4.4 Chromones and Xanthones . . . . . . . . . . . . . . . . . . . . . . . . . 17 2.4.5 Dibenzofuranes .................................. . 18 2.4.6 Pulvinic Acid Derivatives .......................... . 18 2.4.7 Quinones ....................................... . 18 2.5 IR Spectroscopy .................................. . 18 2.6 NMR Spectroscopy ... " ........................... . 19 2.6.1 lH-NMR Spectroscopy ............................ . 19 2.6.2 13C-NMR Spectroscopy ............................ . 20 2.7 Mass Spectrometry ............................... . 22 2.8 Optical Rotation .......................... 28 <' ••••••• X Contents 2.9 Optical Rotatory Dispersion (ORD) and Circular Dichroism (CD) .......................... . 28 2.10 Microcrystallization .............................. . 47 2.11 Thin Layer Chromatography ....................... . 47 2.12 High Performance Liquid Chromatography (HPLC) .... . 51 2.13 Gas Liquid Chromatography (GLC) ................. . 107 2.14 X-Ray Analysis .................................. . 109 2.15 Laser Microprobe Mass Spectrometry (LAMMA) ...... . 109 2.16 Derivatization ................................... . 109 2.17 Cleavage of Depsides ............................. . 112 3 Data of Lichen Substances ......................... . 125 3.1 General Remarks and Abbreviations of the Data ....... . 125 3.2 N-Containing Compounds ......................... . 126 3.3 P-Containing Compounds ......................... . 130 3.4 S-Containing Compounds ......................... . 131 3.5 Polyols, Monosaccharides, Carbohydrates ............ . 131 3.6 Aliphatic and Cycloaliphatic Compounds ............ . 136 3.6.1 Neutral Compounds .............................. . 136 3.6.2 Acids ........................................... . 141 3.7 Aromatic Compounds ............................ . 155 3.7.1 Monocyclic Aromatic Compounds .................. . 155 3.8 Quinones ....................................... . 164 3.8.1 Benzoquinones .................................. . 164 3.8.2 Naphthaquinones and bis-Naphthaquinones .......... . 164 3.8.3 Anthraquinones, Anthrones, bis-Anthraquinones and bis-Anthrones ............................... . 168 3.8.4 Biphenylquinones ................................ . 183 3.8.5 Terphenylquinones ............................... . 184 3.8.6 Phenanthrenequinones ............................ . 184 3.8.7 Perylenequinones ................................ . 185 3.9 Chromanes and Chromones ....................... . 185 3.10 Xanthones and bis-Xanthones ...................... . 190 3.11 Dibenzofuranes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 218 3.12 Diphenylether.... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 229 3.13 Biphenyls.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 236 3.14 Diphenylmethanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 236 3.15 Nostoclides.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 236 3.16 Depsides. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 237 3.16.1 Didepsides ............................... '. . . . . . . . 237 3.16.2 Tri- and Tetra-Depsides . . . . . . . . . . . . . . . . . . . . . . . . . . . . 302 3.16.3 Benzyldepsides....... . . . . . . . . . . . . . . . . . . . . . . . . . . .. 311 3.17 Depsidones... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 313 Contents X 3.18 Depsones. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 353 3.19 Naphthopyranes... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 356 3.20 Terpenoids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 356 3.20.1 Monoterpenoids.................................. 356 3.20.2 Sesquiterpenoids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 359 3.20.3 Diterpenoids..................................... 360 3.20.4 Sesterterpenoids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 361 3.20.5 Triterpenoids..................................... 362 3.20.6 Steroids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 388 3.20.7 Carotenoids...... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 396 3.21 Pulvinic Acid Derivatives. . . . . . . . . . . . . . . . . . . . . . . . . .. 399 3.22 Cleavage Products of Depsides and Depsidones . . . . . . . . 403 Literature. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 447 Addenda .............................................. 475 Subject Index.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 479 ·1 Introduction 1.1 Saxony, Germany, died 1917 at Feuerbach near Short History of the Study Stuttgart), who published 18 papers on lichen substances in the period between 1861 and 1905 of Lichen Substances and wrote an article on Flechtenstoffe in the Lichens - symbiotic organisms of fungi and 1912 edition of Abderhalden's Biochemisches algae - contain a great number of organic Handlexikon. compounds, the so-called lichen substances The lichen substances first known in their which are more or less typical of this group structure were vulpinic acid (Spiegel 1883) and of cryptogames. The lichen substances com prise quite different classes of compounds like amino acid derivatives, sugar alcohols, aliphatic acids, 'Y-, 0- and macrocyclic lactones, mono cyclic aromatic compounds, quinones, chromones, xanthones, dibenzofuranes, de psides, depsidones, depsones, terpenoids, ste roids and carotenoids. This multitude of compounds made the study of their chemistry attractive from the early times of organic chem istry. Bebert (1831) isolated vulpinic acid in 1831, Alms (1832) picrolichenic acid in 1832, and Knop (1844) usnic acid in 1844. Gmelin (1858) published a review on lichen substances already in 1858. The classical period of lichen chemistry is connected with two names: W. Zopf and O. Hesse. W. Zopf (Fig. 1) was a botanist (born 1846 at Ro:Bleben, Thuringia, Germany, died 1909 at Miinster/Westfalen) and published a series of papers on lichen substances which he summarized in the well-known book Die Flechtenstoffe in chemischer, botanischer, pharmakologischer und technischer Beziehung, published in 1907. Zopf's contrahent was the chemist O. Hesse (born 1835 at Obereula, Fig. 1. W. Zopf

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