CAROTENOIDS. Chemistry and Biology

Transcription

1 CAROTENOIDS Chemistry and Biology

2 CAROTENOIDS Chemistry and Biology Edited by Norman I. Krinsky Tufts University Health Sciences Campus Boston, Massachusetts Micheline M. Mathews-Roth Harvard Medical School Boston, Massachusetts and Richard F. Taylor Arthur D. Little, Inc. Cambridge, Massachusetts PLENUM PRESS NEW YORK AND LONDON

3 Library of Congress Cataloging-In-Publication Data International Symposium on Carotenolds (8th: 1987 : Boston, Mass.) Carotenoids : chemistry and biology I edited by Norman I. Krinsky, Micheline M. Mathews-Roth, and Richard F. Taylor. p. cm. "Based on the proceedings of the Eighth International Symposium on Carotenoids, held July 27-31, 1987, in Boston, Massachusetts. "--T.p. verso. Includes bibliographical references. Includes index. ISBN-13: e-isbn-13: DOl: / Carotenolds--Congresses, I. Krinsky, Norman I. II. Mathews -Roth, Michel ine M. III. Taylor, Richard F., IV. Title. [ONLM: 1. Carotenolds--congresses. QU 110 1S05c 1987] QPS71.C35I57 1S S'297--dc20 OLC for Library of Congress SO-7316 CIP Based on the proceedings of the Eighth International Symposium on Carotenoids, held July 27-31, 1987, in Boston, Massachusetts 1989 Plenum Press, New York Softcover reprint of the hardcover lst edition 1989 A Division of Plenum Publishing Corporation 233 Spring Street, New York, N.Y. 100l3 All rights reserved No part of this book may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical. photocopying, microfilming, recording, or otherwise, without written permission from the Publisher

4 ORGANIZING COMMITTEE Norman I. Krinsky (Chairman) Richard F. Taylor (Secretary-Treasurer) Micheline M. Mathews-Roth Lawrence J. Machlin INTERNATIONAL SCIENTIFIC COMMITTEE T. W. Goodwin (U.K.) S. Liaaen-Jensen (Norway) T. Matsuno (Japan) H. J. Mayer (Switzerland) J. Paust (FRG) H. pfander (Switzerland) W. Rau (FRG) K. Tsukida (Japan) B.C.L. Weedon (U.K.) SPONSORS AND CONTRIBUTORS F. Hoffmann-LaRoche & Co. National Cancer Institute, National Institutes of Health (USA), BASF Aktiengesellschaft Amoco Corporation Cyanotech Corporation Kraft Inc. Council for Tobacco Research-USA Inc. Monsanto Company Arthur D. Little, Inc. Taylor-Made Graphics v

5 PREFACE In the mid-1960's, scientists working on carotenoids throughout the World agreed to have periodic meetings for the purpose of discussing and disseminating scientific research results concerning all aspects of carotenoids. The meetings were also organized to act as teaching forums for students, and the major scientific results from each meeting were to result in a publication. Each meeting was planned to be International in scope, being held in different locations in the World, and organized by local, recognized carotenoid scientists. The first of the Carotenoid meetings was held in Trondheim, Norway in Meetings then followed in Las Cuces, New Mexico (1969); Cluj, Roumania (1972); Berne, Switzerland (1975); Madison, Wisconsin (1978); Liverpool; England (1981); and Munich, Federal Republic of Germany (1984). In all of these meetings, the original purposes which stimulated the first meeting were accomplished: scientific discussion, student education and resulting scientific publication.the meetings and the i ~ f o r mresulting a t i o n from them have led to significant advances in carotenoid biochemistry, biology, and chemisty. This publication represents the contributions from a distinguished list of participants. We look forward to the future meetings in this series. ORGANIZING COMMITTEE Norman I. Krinsky Richard F. Taylor Micheline M. Mathews-Roth Lawrence J. Machlin Boston, Massachusetts Cambridge, Massachusetts Nutley, New Jersey

6 CONTENTS Recent Progress in Carotenoid Structures 1 C. H. EUGSTER Carotenoid Structures and Lower Plant Phylogeny 21 T. BJORNLAND Plant Carotenoids 39 J. SZABOLCS Animal Carotenoids 59 T. MATSUNO Carotenoproteins 75 J.B.C. FINDLAY, D.J.C. PAPPIN, M. BRETT and P.F. ZAGALSKY Advances in HPLC and HPLC-MS of Carotenoids and Retinoids 105 R.F. TAYLOR, P.E. FARROW, L.M. YELLE, J.C. HARRIS and I.G. MARENCHIC Advances in the Synthesis of Optically Active Carotenoids 125 H. PFANDER Recent Advances in the Synthesis of Retinoids and Visual Pigment Analogs Studies. 139 R.S.H. LIU, T. MIRZADEGAN and A. TREHAN Artifacts of Natural Carotenoids - Unintended Carotenoid Synthesis 149 S. LIAAEN-JENSEN Carotenoid Biosynthesis - An Overview 167 G. BRITTON The Use of Cell-Free Systems in Studies of Carotenoid Biosynthesis 185 P.M. BRAMLEY On the Desaturation and Cyclization of Carotenes in Chromoplast Membranes 195 P. BEYER and H. KLEINIG Natural Selection of Carotenoid Configurations by the Reaction Center and the Light-Harvesting Complex of Photosynthetic Bacteria 207 Y. KOYAMA ix

7 The Function of Carotenoid Pigments in Photosynthesis and Their Possible Involvement in the Evolution of Higher Plants 223 T.A. MOORE, D. GUST and A. L. MOORE Photoprotective Functions of Carotenoids 229 O.H. WILL III and C.A. SCOVEL Bacterial Carotenoids as Membrane Reinforcers. A General Role for Polyterpenoids: Membrane Stabilization 237 G. OURISSON and Y. NAKATANI New Aspects of Carotenoid Metabolism in Animals 247 K. SCHIEDT Bioavailability of Carotenoids 269 N.V. DIMITROV and D.E. ULLREY Carotenoids in Medicine 279 N.I. KRINSKY B-Carotene Prevention of 7,12-Dimethylbenz(a)anthraceneinduced Transformation of Mouse Mammary Cells in vitro 293 K. MANOHARAN, S. SOM, M. CHATTERJEE and M.R. BANERJEE B-Carotene Protection Against Phototoxicity in vivo 301 A. KORNHAUSER, W. WAMER and L. LAMBERT Pilot Intervention Studies with Carotenoids 313 H.F. STICH. M.P. ROSIN, A.P. HORNBY, B. MATHEW, R. SANKARANARAYANAN and M.K. NAIR Carotenoids and the Immune System 323 A. BENDICH Synthetic Astaxanthin. The Route of a Carotenoid from Research to Commercialization 337 K. BERNHARD Industrial Biosynthesis of Carotenoids 365 A.M. NONOMURA Index 377 x