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Ornithine-Derived Alkaloids Solanaceae and Convolvulaceae: Secondary Metabolites Eckart Eich Solanaceae and Convolvulaceae: Secondary Metabolites Biosynthesis, Chemotaxonomy, Biological and Economic Significance (A Handbook) Prof. Dr. Eckart Eich Freie Universität Berlin Institut für Pharmazie - Pharmazeutische Biologie - Königin-Luise-Str. 2 + 4 14195 Berlin Germany E-mail: [email protected] Cover illustration: Flowers of Ipomoea purpurea (L.) Roth [cultivar; Convolvulaceae] (left) and Solandra maxima (Sessé & Mocino) P.S. Green [Solanaceae] (right). Plotted on the photographs are corresponding constituents: the major anthocyanin pigment and the major alkaloid hyoscyamine, respectively. ISBN 978-3-540-74540-2 e-ISBN 978-3-540-74541-9 The Library of Congress Control Number: 2007933490 © 2008 Springer-Verlag Berlin Heidelberg This work is subject to copyright. All rights reserved, whether the whole or part of the material is concerned, specifi cally the rights of translation, reprinting, reuse of illustrations, recitation, broad- casting, reproduction on microfi lm 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 permission for use must always be obtained from Springer. Violations are liable for prosecution under the German Copyright Law. The use of registered names, trademarks, etc. in this publication does not imply, even in the absence of a specifi c statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. Product liability: The publishers cannot guarantee the accuracy of any information about dosage and application contained in this book. In every individual case the user must check such information by consulting the relevant literature. Cover design: WMXDesign GmbH, Heidelberg, Germany Printed on acid-free paper SPIN 11003991 5 4 3 2 1 0 springer.com „Was du ererbt von deinen Vätern hast, Erwirb es, um es zu besitzen.“ (All that you have, bequeathed you by your fathers, Earn it in order to possess it.) Johann Wolfgang von Goethe (Faust I) This book is based on a multitude of results obtained in botany, phytochemistry, and other biological sciences from all over the world since the beginning of modern research two hundred years ago. It is dedicated to all the scientists who have contributed to these results. Acknowledgments This interdisciplinary book is a result of my long-standing fascination for the bot- any of solanaceous and convolvulaceous plants as well as their ability to synthesize a multitude of chemical species with their biological activities. However, this book would not have been realized without the support of the following individuals to whom I express my sincere gratitude: • For conscientious reading and competent commenting on the manuscript of the book: Priv.-Doz. Dr. Kristina Jenett-Siems and Prof. Dr. Heinz H. Pertz, Freie Universität Berlin, Germany (Chaps. 3–8), Priv.-Doz. Dr. Michael Stech, Universiteit Leiden, The Netherlands (Chap. 2), and my daughter, Dr. Susanne Eich-Greatorex, Universitet for miljø- og biovitenskap, Ås, Norway (Chap. 1) • For introducing me, an ignoramus in computer affairs until 2003, to the secrets of the personal computer and its various functions with patience and unremitting efforts: Dr. Thomas Schimming, Berlin • For rescue of my personal computer in severe cases of crashes: Dr. Colja Schubert, Heinrich Hertz Institut Berlin • For long-term botanical advice and information: Daniel F. Austin, Ph.D., Emeritus Professor at Florida Atlantic University, Boca Raton, and Research Associate of the Arizona-Sonora Desert Museum, Tucson, USA • For the excellent advice and guidance as well as for the generous acceptance of my requests: the life sciences editorial staff of Springer, especially Dr. Jutta Lindenborn and Dr. Dieter Czeschlik, Heidelberg, Germany and the copyeditor, John Kirby, Malvern, UK • For the contribution of 53 photographs to the Colour Plates of this book taken during our common journeys through predominantly tropical countries, for the essential support in many different respects, e.g., by proof-reading, discussions, excellent organizing, and last but not least for the forbearance of my preoccupation with the book and long-term encouragement: my wife, Elisabeth Bäumel-Eich, Berlin Berlin, August 2007 Eckart Eich vii Contents 1 Introduction . 1 1.1 Philosophy and Aims of this Book. 1 1.1.1 The Large Solanales Families as a Topic . 1 1.1.2 General Role of the Secondary Metabolism for a Specific Characterization and Classification of Plant Taxa . 1 1.1.3 Bird’s-Eye View of Two Centuries of Phytochemical Research on Solanaceae and Convolvulaceae. 2 1.2 Secondary Metabolism of the Large Solanales Families . 3 1.2.1 Historical Background. 3 1.2.2 Common Ground and Differences of the Solanales Families. 4 1.2.3 Similar Secondary Metabolism of the Large Solanales Families. 5 1.3 Strategy . 6 1.4 Criteria for Selection of Secondary Metabolites Based on their Specific Significance . 6 1.5 Accumulation or Low-Level Occurrence of Secondary Metabolites . 7 1.6 Significance of Chemotaxonomy . 8 1.7 Principal Nomenclatural Points . 8 1.7.1 Species Names. 8 1.7.2 Chemical Trivial Names . 8 References . 9 2 Classification and System in Solanales . 11 2.1 Position of the Order Solanales and its Families . 11 2.1.1 Traditional Systematics . 11 2.1.2 Phylogenetic Classification Based on Predominantly (Macro)molecular Data Sets . 12 ix x Contents 2.2 Solanaceae A.L. de Jussieu: Delimitation, Intrafamilial Circumscription and Relationships . 15 2.2.1 Traditional Systematics . 15 2.2.2 Phylogenetic Classification Based on Predominantly (Macro)molecular Data Sets . 16 2.3 Convolvulaceae A.L. de Jussieu: Delimitation, Intrafamilial Circumscription and Relationships. 21 2.3.1 Traditional Systematics . 22 2.3.2 Phylogenetic Classification Based on Predominantly (Macro)molecular Data Sets . 22 2.4 Uncharted Territory with Regard to Secondary Metabolites of the Solanales. 23 References . 28 3 Ornithine-Derived Alkaloids. 33 3.1 Simple Pyrrolidines. 65 3.1.1 Discovery and Structural Elucidation . 65 3.1.2 Occurrence in the Solanaceae . 68 3.1.3 Occurrence in the Convolvulaceae . 70 3.1.4 Biosynthesis. 73 3.1.5 Significance . 74 3.2 N-Acylpyrrolidines (Pyrrolidides, Pyrrolidine Amides). 74 3.2.1 Occurrence in the Solanaceae . 75 3.2.2 Occurrence in the Convolvulaceae . 75 3.2.3 Biosynthesis. 76 3.2.4 Significance . 76 3.3 Nicotinoids (Tobacco Alkaloids) . 77 3.3.1 Discovery and Structure Elucidation. 77 3.3.2 Occurrence in the Solanaceae . 87 3.3.3 Occurrence in the Convolvulaceae . 94 3.3.4 Biosynthesis of Pyrrolidine-Type Nicotinoids . 94 3.3.5 Biosynthesis of Piperidine-/Piperideine-Type Nicotinoids . 97 3.3.6 Significance . 98 3.4 Tropanes . 109 3.4.1 Discovery and Structure Elucidation. 109 3.4.2 Occurrence in the Solanaceae . 114 3.4.3 Occurrence in the Convolvulaceae . 130 3.4.4 Biosynthesis. 150 3.4.5 Significance . 153 3.5 Calystegines (Polyhydroxylated Nortropanes) . 160 3.5.1 Discovery and Structure Elucidation. 160 3.5.2 Occurrence in the Solanaceae . 164 Contents xi 3.5.3 Occurrence in the Convolvulaceae . 165 3.5.4 Biosynthesis. 175 3.5.5 Significance . 176 3.6 Indolizidines . 177 3.7 Pyrrolizidines . 178 3.7.1 Occurrence in the Convolvulaceae . 180 3.7.2 Significance . 187 References . 188 4 Tryptophan-derived Alkaloids . 213 4.1 β-Carbolines . 213 4.1.1 Occurrence in the Solanaceae . 213 4.1.2 Occurrence in the Convolvulaceae . 214 4.2 Ergolines . 215 4.2.1 Discovery and Structure . 215 4.2.2 Biosynthesis. 218 4.2.3 Occurrence in the Convolvulaceae . 222 4.2.4 Location and Origin of Ergoline Alkaloids. 241 4.2.5 Significance . 245 References . 252 5 Miscellaneous Alkaloids . 261 5.1 Occurrence in the Solanaceae. 261 5.1.1 Fabianine . 261 5.1.2 2-Methoxy-3-isobutylpyrazine . 261 5.1.3 Nicotianamine . 262 5.1.4 Solamines . 263 5.1.5 Pyrrole Alkaloids. ..
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