Medicinal Plant Biotechnology-Teaching Book

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Medicinal Plant Biotechnology Edited by Oliver Kayser and Wim J. Quax

Medicinal Plant Biotechnology. From Basic Research to Industrial Applications Edited by Oliver Kayser and Wim J. Quax Copyright 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN 978-3-527-31443-0

18072007 Knowledge for GenerationsEach generation has its unique needs and aspirations. When Charles Wiley first opened his small printing shop in lower Manhattan in 1807, it was a generation of boundless potential searching for an identity. And we were there, helping to define a new American literary tradition. Over half a century later, in the midst of the Second Industrial Revolution, it was a generation focused on building the future. Once again, we were there, supplying the critical scientific, technical, and engineering knowledge that helped frame the world. Throughout the 20th Century, and into the new millennium, nations began to reach out beyond their own borders and a new international community was born. Wiley was there, expanding its operations around the world to enable a global exchange of ideas, opinions, and know-how. For 200 years, Wiley has been an integral part of each generations journey, enabling the flow of information and understanding necessary to meet their needs and fulfill their aspirations. Today, bold new technologies are changing the way we live and learn. Wiley will be there, providing you the must-have knowledge you need to imagine new worlds, new possibilities, and new opportunities. Generations come and go, but you can always count on Wiley to provide you the knowledge you need, when and where you need it!

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Medicinal Plant BiotechnologyFrom Basic Research to Industrial Applications Volume I

Edited by Oliver Kayser and Wim J. Quax

The Editors Prof. Dr. Oliver Kayser Rijksuniversiteit Groningen Pharmaceutical Biology Antonius Deusinglaan 1 9713 AV Groningen The Netherlands Prof. Dr. Wim J. Quax Rijksuniversiteit Groningen Pharmaceutical Biology Antonius Deusinglaan 1 9713 AV Groningen The Netherlands

All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the information contained in these books, including this book, to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details or other items may inadvertently be inaccurate.Library of Congress Card No.: applied for British Library Cataloguing-in-Publication Data

A catalogue record for this book is available from the British Library.Bibliographic information published by the Deutsche Nationalbibliothek

The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available in the Internet at http://dnb.d-nb.de.Cover

G. Schulz, FugnnheimCover illustration:

2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form by photoprinting, microfilm, or any other means nor transmitted or translated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law. Composition Detzner Fotosatz, Speyer Printing betz-druck GmbH, Darmstadt Bookbinding Litges & Dopf Buchbinderei GmbH, Heppenheim Cover Adam Design, Weinheim Anniversary Logo Design Richard Pacifico Printed in the Federal Republic of Germany Printed on acid-free paper ISBN: 978-3-527-31443-0

V8 light metal engine block, by Josef Schmid, NAGEL Maschinenund Werkzeugfabrik GmbHCover

This text describes the cover with its very interesting details and includes the photographers name and maybe his address. This text describes the cover with its very interesting details and includes the photographers name and maybe his address. This text describes the cover with its very interesting details and includes the photographers name and maybe his address.

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Medicinal Plant Biotechnology. From Basic Research to Industrial Applications Edited by Oliver Kayser and Wim J. Quax Copyright 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN 978-3-527-31443-0

V

ContentsPreface XVII Foreword XIX List of Contributors XXIII Color Plates XXIX

Volume I Part 1 1 Linking Plants, Genes, and Biotechnology 1 The Engineering of Medicinal Plants: Prospects and Limitations of Medicinal Plant Biotechnology 3 Matthys K. Julsing, Wim J. Quax, and Oliver Kayser Introduction 3 Genetic Transformation and Production of Transgenic Plants 5 Pathway Engineering and Combinatorial Biosynthesis 5 Bioprocessing 6 Plant Propagation 7 Bioanalytics and Metabolomics 7 Future Prospects 8 References 8 Metabolomics 9 Young Hae Choi, Hye Kyong Kim, and Robert Verpoorte Introduction 9 Analytical Methods 11 Chromatography 11 Gas Chromatography (GC) 11 High-Performance Liquid Chromatography (HPLC) 13 Capillary Electrophoresis (CE) 14 Thin-Layer Chromatography (TLC) 14

1.1 1.2 1.3 1.4 1.5 1.6 1.7

2 2.1 2.2 2.2.1 2.2.1.1 2.2.1.2 2.2.1.3 2.2.1.4

Medicinal Plant Biotechnology. From Basic Research to Industrial Applications Edited by Oliver Kayser and Wim J. Quax Copyright 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN 978-3-527-31443-0

VI

Contents

2.2.2 2.2.2.1 2.2.2.2 2.2.3 2.2.4 2.3 2.4 2.5 2.6

Spectroscopy 14 Mass Spectrometry (MS) 14 Nuclear Magnetic Resonance (NMR) Spectrometry 16 Identification of Metabolites 18 Sample Treatment 18 Data Handling 21 The General Set-Up of a Metabolomics Project 25 Applications 26 Conclusions 26 References 27 HPLC-NMR Techniques for Plant Extract Analysis 29 Dan Strk, Maja Lambert, and Jerzy W. Jaroszewski Introduction 29 Hyphenation of Separation Techniques and Spectroscopic Methods 30 Direct HPLC-NMR Methods 32 Continuous-Flow HPLC-NMR 32 Stopped-Flow HPLC-NMR 33 Loop-Collection HPLC-NMR 36 Indirect HPLC-NMR Methods 36 HPLC-SPE-NMR 37 Cryogenically Cooled NMR Probes 41 Miniaturization 41 Conclusions 43 References 43 Plant-Associated Microorganisms (Endophytes) as a New Source of Bioactive Natural Products 49 Gary Strobel Abstract 49 Introduction 49 Why Are There Needs for New Medicines? 50 Natural Products in Medicine 51 Endophytic Microbes 52 Rationale for Plant Selection 53 Endophytes and Biodiversity 55 Endophytes and Natural Products 56 Isolation, Preservation and Storage of Endophytic Cultures for Product Isolation 57 Some Examples of Bioactive Natural Products from Endophytes 57 Endophytic Fungal Products as Antibiotics 57 Endophytic Bacterial Products as Antibiotics 61 Endophytic Streptomycetes as Antibiotic Producers 62 Volatile Antibiotics from Endophytes 63

3 3.1 3.2 3.3 3.3.1 3.3.2 3.3.3 3.4 3.4.1 3.5 3.6 3.7

4

4.1 4.2 4.3 4.4 4.5 4.6 4.7 4.7.1 4.7.2 4.7.2.1 4.7.2.2 4.7.2.3 4.7.2.4

Contents

VII

4.7.2.5 4.7.2.6 4.7.2.7 4.7.2.8 4.8 4.9

Antiviral Compounds from Endophytes 64 Endophytic Fungal Products as Anticancer Agents 65 Endophytic Fungal Products as Antioxidants 67 Endophytic Fungal Products as Immunosuppressive Compounds 68 Surprising Results from Molecular Biology Studies on Pestalotiopsis microspora 68 Concluding Statements 69 Acknowledgments 70 References 70 DNA Profiling of Plants 73 Hilde Nybom and Kurt Weising Introduction 73 Methodology of Plant DNA Profiling 74 DNA Sequencing 75 Multilocus DNA Profiling 76 Hybridization-Based RFLP Fingerprinting 77 PCR with Arbitrary Primers 77 PCR with Microsatellite-Complementary Primers 77 AFLP Analysis 78 Locus-Specific Microsatellite DNA Markers 78 PCR-Based RFLP Analysis of Organellar and Nuclear Genomes 79 Other DNA Marker Methods 80 The Next Generation: SNPs and DNA Microarrays 80 Applications 81 Genotype Identification 81 Plant Species 81 Plant Cultivars and Accessions 83 In-Vitro-Propagated Plant Material 83 Genetic Diversity 84 Variation and Relatedness Among Cultivars and Accessions 84 Amount and Distribution of Variability in Wild-Growing Plants 85 Plant Systematics 86 Gene Tagging 87 Conclusions 88 References 89 Bioprospecting: The Search for Bioactive Lead Structures from Nature 97 Michael Wink Abstract 97 Introduction 97 The Function of Secondary Metabolites 102 Modes of Action 103 Biomembranes 106

5 5.1 5.2 5.2.1 5.2.2 5.2.2.1 5.2.2.2 5.2.2.3 5.2.2.4 5.2.3 5.2.4 5.2.5 5.2.6 5.3 5.3.1 5.3.1.1 5.3.1.2 5.3.1.3 5.3.2 5.3.2.1 5.3.2.2 5.3.2.3 5.3.3 5.4

6

6.1 6.2 6.3 6.3.1

VIII

Contents

6.3.2 6.3.3 6.4 6.5

Proteins and Protein Conformation 107 DNA and RNA 112 The Utilization of Secondary Metabolites in Medicine Conclusions 115 Key references 115

114

7

7.1 7.2 7.3 7.3.1 7.3.2 7.3.3 7.3.4 7.3.5 7.3.6 7.3.7 7.3.8 7.3.9 7.3.10 7.3.10.1 7.3.10.2 7.3.10.3 7.4

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