Carotenoids Volume 4: Natural Functions

The Carotenoids book series provides detailed accounts of the fundamental chemistry of carotenoids and the basic methods used in carotenoid research, and critical discussions of the biochemistry, functions and applications of these important compounds. Vo

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Carotenoids Volume 4: Natural Functions Edited by

G. Britton S. Liaaen-Jensen H. Pfander

Birkhäuser Verlag Basel · Boston · Berlin

Editors: Dr. George Britton University of Liverpool School of Biological Sciences Biosciences Building Crown Street Liverpool L69 7ZB UK

Professor Dr. Dr. h.c. Synnøve Liaaen-Jensen Organic Chemistry Laboratories Department of Chemistry Norwegian University of Science and Technology (NTNU) 7491 Trondheim Norway

Prof. Dr. Hanspeter Pfander CaroteNature GmbH Chief Operating Officer Muristrasse 8e 3006 Bern Switzerland

Library of Congress Control Number: 2008932322

Bibliographic information published by Die Deutsche Bibliothek Die Deutsche Bibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data is available in the internet at http://dnb.ddb.de

ISBN 3-7643-7498-3 Birkhäuser Verlag, Basel – Boston - Berlin

The publisher and editor can give no guarantee for the information on drug dosage and administration contained in this publication. The respective user must check its accuracy by consulting other sources of reference in each individual case. The use of registered names, trademarks etc. in this publication, even if not identified as such, does not imply that they are exempt from the relevant protective laws and regulations or free for general use. This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, re-use of illustrations, recitation, broadcasting, reproduction on microfilms or in other ways, and storage in data banks. For any kind of use permission of the copyright owner must be obtained.

© 2008 Birkhäuser Verlag, P.O. Box 133, CH-4010 Basel, Switzerland Part of Springer Science+Business Media Printed on acid-free paper produced from chlorine-free pulp. TFC Printed in Germany Cover design: Markus Etterich, Basel ISBN 978-3-7643-7498-3

e-ISBN 978-3-7643-7499-0

98765432

www.birkhauser.ch

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Contents List of Contributors ……………………………………………………..…… Preface …………………………………………………………...…………… Acknowledgements …………………………………………………………... Editors’ Notes ………………………………………………………………… Abbreviations …………………………………………………………………

xviii xxiv xxv xxvi xxviii

Chapter 1: Special Molecules, Special Properties George Britton, Synnøve Liaaen-Jensen and Hanspeter Pfander A. Introduction ………………………………………………………………… B. Structure, Properties and Function ……………………………………….. 1. Three-dimensional shape ……………………………………………….. 2. The conjugated double-bond system ……………………………………. 3. Molecular interactions ………………………………….……………….. C. Functions of Carotenoids …………………………………………………... D. Metabolites and Breakdown Products ……………………………………. E. Conclusions ………………………………………………………………….

1 2 2 3 4 5 6 6

Chapter 2: Structure and Chirality Synnøve Liaaen-Jensen A. Introduction ………………………………………………………………… 7 B. Three-dimensional Carotenoid Structures ……………………………….. 7 C. Methods for Structure Determination ……………………………………. 9 References ……………………………………………………………………… 14

Chapter 3: E/Z Isomers