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Marine Chemical Ecology Edited by James B. McClintock Professor of Biology University of Alabama at Birmingham Birmingham, Alabama Bill J. Baker Associate Professor of Chemistry University of South Florida Tampa, Florida CRC Press Boca Raton London New York Washington, D.C. Cover photograph © 1997 Norbert Wu www.norbertwu.com. The Antarctic red macroalga, Phyllophora antarctica, being held by the sea urchin, Sterechinus neumayeri, in a mutualistic relationship mediated by chemical and physical defenses. Library of Congress Cataloging-in-Publication Data Marine chemical ecology James B. McClintock, Bill J. Baker, editors. p. cm.—(Marine science series) Includes bibliographical references and index. ISBN 0-8493-9064-8 (alk. paper) 1. Marine chemical ecology. I. McClintock, James B. II. Baker, Bill J. (Bill James), 1958-. III. Series. QH541.5.S3 M254 2001 577.7?14—dc21 2001025040 This book contains information obtained from authentic and highly regarded sources. Reprinted material is quoted with permission, and sources are indicated. A wide variety of references are listed. Reasonable efforts have been made to publish reliable data and information, but the author and the publisher cannot assume responsibility for the validity of all materials or for the consequences of their use. Neither this book nor any part may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, microfilming, and recording, or by any information storage or retrieval system, without prior permission in writing from the publisher. All rights reserved. Authorization to photocopy items for internal or personal use, or the personal or internal use of specific clients, may be granted by CRC Press LLC, provided that $1.50 per page photocopied is paid directly to Copyright Clearance Center, 222 Rosewood Drive, Danvers, MA 01923 USA. 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Visit the CRC Press Web site at www.crcpress.com © 2001 by CRC Press LLC No claim to original U.S. Government works International Standard Book Number 0-8493-9064-8 Library of Congress Card Number 2001025040 Printed in the United States of America 1 2 3 4 5 6 7 8 9 0 Printed on acid-free paper Preface As early as the middle of the 19th century, scientists were beginning to isolate and characterize organic compounds from nature. Modern studies of the nature of natural products, those compounds not involved in primary metabolic processes, began in the 1930s and 1940s. In the decades that followed, scientists began to focus on why organisms produce these compounds. At the same time, studies of factors that regulate the distribution and abundance of species were giving rise to the field of ecology. The subsequent combination of these two disciplines allowed for investigations of secondary metabolites and their functional roles in mediating reproductive processes, predator–prey interactions, and competition. The inherently interdisciplinary field of chemical ecology has as its roots studies of chemical interactions in terrestrial microbial and plant systems. Terrestrial plant studies led to the logical extension of similar studies in marine plants, primarily macroalgae. The earliest studies of the chemical ecology of marine animals focused on invertebrates that were plant-like, lacking locomotive ability or obvious physical means of protection. Surprisingly, such marine studies really only have been undertaken in earnest during the past 25 years, due largely to the lack of knowledge of the chemistry of marine organisms. It is probably no coincidence that the breadth of marine organisms studied expanded in concert with developments in underwater technology. Today, the field of marine chemical ecology encompasses a broad interdisciplinary community of scientists. Among its many participants are those interested in understanding predator–prey interactions, competition, chemical communication, fouling, pathogen–host interactions, biosynthesis, reproduction, and the evolution of secondary metabolites. Bringing diverse disciplines to bear upon these fundamental questions has generated a body of knowledge that is truly synergistic and unequivocally greater than the sum of its parts. The field of marine chemical ecology has been gaining momentum. Over the past decade, a number of excellent review articles and at least one book have been published on this topic. However, a field so diverse and interdisciplinary requires, from time to time, a conceptual synthesis. There has been, to date, no single source that provides this synthetic overview. This book is such an attempt. In four topical sections, this work spans aspects of marine chemical ecology from molecular to community levels, bridging these diverse disciplines. The authors have contributed their considerable experiences, resulting in a collective effort that will hopefully stimulate new ideas and inspire a new generation of researchers. The introductory section, Chapters 1 through 3, provides a broad phylogenetic overview of marine organic chemistry. Emphasizing evolutionary, ecological, and biosynthetic considerations, the authors of these chapters set a foundation for the chapters that follow. Harper et al. provide the first balanced account of patterns of specific classes of secondary metabolites among marine organisms. Garson has provided an update of her periodic reviews of the field of marine biosynthesis with an emphasis on ecologically important compounds. Cimino and Ghiselin foray into theoretical analyses of evolutionary trends in marine biota in an effort to rationalize observed patterns of chemical defense in the marine realm. The second section, Chapters 4 through 10, takes an organismal approach to understanding the role of secondary metabolites in mediating trophic interrelationships. While much of the content of this volume focuses on sessile organisms, Stachowicz reports on chemical ecology of mobile benthic invertebrates, and McClintock et al. review what is known to date about the chemical ecology of meroplankton and holoplankton and offer suggestions for future research. Trophic relationships in the oceanic water column have potential significance in influencing material and energy flux in planktonic food webs. Chemical ecology is ultimately driven by evolutionary pressures, which Cronin reviews from the point of view of resource allocation strategies. The macroalgae are perhaps most thoroughly studied with respect to their trophic chemical ecology. This fertile field is addressed by Paul et al. Marine chemical ecology has also been considered on broad biogeographic and temporal scales. Most notable among marine biogeographic analyses are those applied to the macroalgae, the resulting patterns of which are reviewed by Van Alstyne et al. Biogeographic patterns in higher organisms are less well defined; however, recent evidence from the south polar region, which Amsler et al. review from a chemical analytical perspective, is beginning to illuminate global patterns, at least with respect to trophic interactions. Furthering our understanding of the functional spatial distribution of metabolites, Steinberg et al. examines chemical interactions at organismal surfaces. Section III, Chapters 11 through 15, reviews cellular and physiological aspects of marine chemical ecology. 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