Progress in the Chemistry of Organic Natural Products, Vol. 93, DOI 10.1007/978-3-7091-0140-7 1, # Springer-Verlag/Wien 2010 2 S.A
Total Page：16
File Type：pdf, Size：1020Kb
Fortschritte der Chemie organischer Naturstoffe Progress in the Chemistry of Organic Natural Products Founded by L. Zechmeister Editors: A.D. Kinghorn, Columbus, OH H. Falk, Linz J. Kobayashi, Sapporo Honorary Editor: W. Herz, Tallahassee, FL Editorial Board: V.M. Dirsch, Vienna S. Gibbons, London N.H. Oberlies, Greensboro, NC Y. Ye, Shanghai 93 Fortschritte der Chemie organischer Naturstoffe Progress in the Chemistry of Organic Natural Products Authors: S.A. Begum, M. Sahai, and A.B. Ray E. Go¨ssinger M. Luzhetska, J. Ha¨rle, and A. Bechthold SpringerWienNewYork Prof. A. Douglas Kinghorn, College of Pharmacy, Ohio State University, Columbus, OH, USA em. Univ.-Prof. Dr. H. Falk, Institut fu¨r Organische Chemie, Johannes-Kepler-Universita¨t, Linz, Austria Prof. Dr. J. Kobayashi, Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan 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. # 2010 Springer-Verlag/Wien Printed in Germany SpringerWienNewYork is a part of Springer Science þ Business Media springer.at Product Liability: The publisher can give no guarantee for the information contained in this book. This also refers to that on drug dosage and application thereof. In each individual case the respective user must check the accuracy of the information given by consulting other pharmaceutical literature. The use of 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. Library of Congress Catalog Card Number: 2010926970 Typesetting: SPI, Chennai Printed on acid-free and chlorine-free bleached paper SPIN: 12794805 With 40 (partly coloured) Figures ISSN 0071-7886 ISBN 978-3-7091-0139-1 e-ISBN 978-3-7091-0140-7 DOI 10.1007/978-3-7091-0140-7 SpringerWienNewYork Contents List of Contributors ........................................................... vii Non-conventional Lignans: Coumarinolignans, Flavonolignans, and Stilbenolignans ............................................................ 1 Sajeli A. Begum, Mahendra Sahai, and Anil B. Ray 1. Introduction .. ................................................................ 2 2. Coumarinolignans ............................................................ 3 2.1. Occurrence of Coumarinolignans ....................................... 3 2.2. Classification of Coumarinolignans ..................................... 5 2.3. Structure Elucidation of Coumarinolignans ... ......................... 7 2.4. Chemistry of Coumarinolignans ....................................... 14 2.5. Biological Activity of Coumarinolignans ............................. 25 2.6. Biogenesis of Coumarinolignans ...................................... 27 3. Flavonolignans .............................................................. 28 3.1. Occurrence of Flavonolignans ......................................... 29 3.2. Features of Flavonolignans and Their Classification .................. 29 3.3. Structure Elucidation of Flavonolignans .............................. 33 3.4. Chemistry of Flavonolignans .......................................... 38 3.5. Biological Activity of Flavonolignans ................................. 48 3.6. Biogenesis of Flavonolignans .......................................... 49 4. Stilbenolignans .............................................................. 50 4.1. Occurrence and Features of Stilbenolignans .. ........................ 50 4.2. Structure Elucidation and Synthesis of Stilbenolignans ............... 52 4.3. Biological Activity of Stilbenolignans ................................. 61 4.4. Biogenesis of Stilbenolignans ......................................... 62 References ...................................................................... 64 Picrotoxanes ................................................................... 71 Edda Go¨ssinger 1. Introduction .. ............................................................... 72 v vi Contents 2. Tabular Overview of the Picrotoxanes ..................................... 73 3. Occurrence ... .............................................................. 108 3.1. Systematic and Geographic Occurrence of Picrotoxane-Containing Plants .................................... 108 3.2. Parasitic Plants ....................................................... 110 3.3. Picrotoxanes Found in Animals and Animal Products .............. 110 3.4. The Riddle of the Scattered Taxonomic Occurrence of Picrotoxanes ....................................................... 111 4. Isolation of Picrotoxanes ................................................... 111 4.1. Examples of Recent Isolation Procedures ........................... 112 5. Structure Determination of Picrotoxanes .................................. 117 5.1. Main Picrotoxanes of the Menispermaceae .......................... 117 5.2. Main Picrotoxanes of the Coriariaceae .............................. 119 5.3. Picrotoxanes Isolated from Toxic Honey ............................ 121 5.4. Picrotoxanes of the Picrodendraceae ................................ 121 5.5. Picrotoxanes from Dendrobium Species ............................. 127 6. Total Syntheses of Picrotoxanes ........................................... 134 6.1. Overview ............................................................. 134 6.2. Description of the Syntheses ......................................... 138 7. Biosynthesis of Picrotoxanes .............................................. 180 7.1. Investigations on the Biosynthesis of Dendrobines ................. 181 7.2. Investigations on the Biosynthesis of Sesquiterpene Picrotoxanes .......................................................... 184 8. Physiological Activity of Picrotoxanes .................................... 188 8.1. Toxicity .............................................................. 188 8.2. Picrotoxanes as Therapeutics ........................................ 191 8.3. Picrotoxanes as Epileptogenic Compounds .......................... 192 8.4. Picrotoxanes as Tools in Neurobiological Research ................ 192 Abbreviations .................................................................. 194 References ..................................................................... 197 Combinatorial and Synthetic Biosynthesis in Actinomycetes ............. 211 Marta Luzhetska, Johannes Ha¨rle, and Andreas Bechthold 1. Introduction .. .............................................................. 211 2. Combinatorial Biosynthesis and Synthetic Biosynthesis .................. 212 2.1. Achievements in Combinatorial Biosynthesis . ...................... 213 2.2. Challenges for Combinatorial Biosynthesis ... ...................... 215 2.3. Synthetic Biosynthesis ............................................... 224 References ..................................................................... 230 Author Index ................................................................. 239 Subject Index ................................................................. 259 Listed in PubMed Contributors Andreas Bechthold Institut fu¨r Pharmazeutische Wissenschaften, Lehrstuhl fu¨r Pharmazeutische Biologie und Biotechnologie der Albert-Ludwigs-Universita¨t Freiburg, Stefan-Meier-Strasse 19, 79104 Freiburg, Germany [email protected] Sajeli A. Begum Department of Pharmaceutics, Institute of Technology, Banaras Hindu University, Varanasi 221005, India [email protected] Edda Go¨ssinger Institut fu¨r Organische Chemie der Universita¨t Wien, Wa¨hringer Strasse 38, 1090 Vienna, Austria [email protected] Johannes Ha¨rle Institut fu¨r Pharmazeutische Wissenschaften, Lehrstuhl fu¨r Pharmazeutische Biologie und Biotechnologie der Albert-Ludwigs-Universita¨t Freiburg, Stefan-Meier-Strasse 19, 79104 Freiburg, Germany [email protected] Marta Luzhetska Institut fu¨r Pharmazeutische Wissenschaften, Lehrstuhl fu¨r Pharmazeutische Biologie und Biotechnologie der Albert-Ludwigs-Universita¨t Freiburg, Stefan-Meier-Strasse 19, 79104 Freiburg, Germany [email protected] Anil B. Ray C-38 – Ashokpuram, Dafi, Varanasi 221011, India [email protected] Mahendra Sahai Department of Medicinal Chemistry, IMS, Banaras Hindu University, Varanasi 221005, India [email protected] vii Born in 1978 in Cuddalore, India, Dr. (Mrs) Sajeli A. Begum studied for her M. Pharm. in Pharmaceutical Chemistry (2001) and performed a chemical investi- gation into the non-alkaloidal constituents of Solanaceous plants for her doctoral thesis. She received a Ph.D. in Medicinal Chemistry (2005) from Banaras Hindu University, Varanasi, India. She is a recipient of a Council of Scientific Industrial Research (CSIR) – Senior Research Fellowship, India, for her Ph.D. project and a Deutscher Akademischer Austausch Dienst (DAAD) Fellowship (2004) to pursue part of her doctoral research at Eberhard Karls Universita¨t, Tu¨bingen, in the group of Dr. Roderich Suessmuth. Since 2005, she has been working as an assistant professor in the Department of Pharmaceutics, Institute of Technology, Banaras Hindu University, and doing research on phytochemical constituents. Her prime research interests are centered on isolation, structure