Chemistry and safety of acrylamide in food PDF
Preview Chemistry and safety of acrylamide in food
Chemistry and Safety of Acrylamide in Food ADVANCES IN EXPERIMENTAL MEDICINE AND BIOLOGY Editorial Board: NATHAN BACK, State University of New York at Buffalo IRUN R. COHEN, The Weizmann Institute of Science DAVID KRITCHEVSKY, Wistar Institute ABEL LAJTHA, N. S. Kline Institute for Psychiatric Research RODOLFO PAOLETTI, University of Milan Recent Volumes in this Series Volume 553 BIOMATERIALS: From Molecules to Engineered Tissues Edited by Nesrin Hasirci and Vasif Hasirci Volume 554 PROTECTING INFANTS THROUGH HUMAN MILK: Advancing the Scientific Evidence Edited by Larry K. Pickering, Ardythe L. Morrow, Guillermo M. Ruiz-Palacios, and Richard J. Schanler Volume 555 BREAST FEEEDING: Early Influences on Later Health Edited by Gail Goldberg, Andrew Prentice, Ann Prentice, Suzanne Filteau, and Elsie Widdowson Volume 556 IMMUNOINFORMATICS: Opportunities and Challenges of Bridging Immunology with Computer and Information Sciences Edited by Christian Schoenbach, V. Brusic, and Akihiko Konagaya Volume 557 BRAIN REPAIR Edited by M. Bahr Volume 558 DEFECTS OF SECRETION IN CYSTIC FIBROSIS Edited by Carsten Schultz Volume 559 CELL VOLUME AND SIGNALING Edited by Peter K. Lauf and Norma C. Adragna Volume 560 MECHANISMS OF LYMPHOCYTE ACTIVATION AND IMMUNE REGULATION X: INNATE IMMUNITY Edited by Sudhir Gupta, William Paul, and Ralph Steinman Volume 561 CHEMISTRY AND SAFETY OF ACRYLAMIDE IN FOOD Edited by Mendel Friedman and Don Mottram A Continuation Order Plan is available for this series. A continuation order will bring delivery of each new volume immediately upon publication. Volumes are billed only upon actual shipment. For further information please contact the publisher. Chemistry and Safety of Acrylamide in Food Edited by Mendel Friedman Agricultural Research Service, USDA Albany, California and Don Mottram University of Reading Reading, United Kingdom Sprii nger Library of Congress Cataloging-in-Publication Data Chemistry and safety of acrylamide in food/edited by Mendel Friedman and Don Mottram. p. cm. (Advances in experimental medicine and biology;, v. 561) Includes bibliographical references and index. ISBN 0-387-23920-0 1. Acrylamide—Toxicology. 2. Food—Toxicology. I. Friedman, Mendel. II. Mottram D. S. (Donald S.). III. Series RA1242.A44C447 2005 615.9'54—dc22 2005040244 Proceedings of ACS Symposium on "Chemistry and Safety of Acrylamide in Food" held at the American Chemical Society Meeting in Anaheim, California, March 28-April 1, 2004 ISSN: 0065 2598 ISBN-10: 0-387-23920-0 (Hardbound) Printed on acid-free paper. ISBN-13: 987-0387-23920-0 ©2005 Springer Science-HBusiness Media, Inc. All rights reserved. This work may not be translated or copied in whole or in part without the written permission of the publisher (Springer Science-HBusiness Media, Inc., 233 Spring Street, New York, NY 10013, USA), except for brief excerpts in connection with reviews or scholarly analysis. Use in connection with any form of information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed is forbidden. The use in this publication of trade names, trademarks, service marks and similar terms, even if they are not identified as such, is not to be taken as an expression of opinion as to whether or not they are subject to proprietary rights. Printed in the United States of America 9 8 7 6 5 4 32 springeronline.com PREFACE Acrylamide (CH2=CH-CONH2), an industrially produced conjugated reactive molecule, is used worldwide to synthesize polyacrylamide. The polymer has found numerous applications as a soil conditioner, in wastewater treatment, in the cosmetic, paper, and textile industries, and in the laboratory as a solid support for the separation of proteins by electrophoresis. Monomeric acrylamide is also widely used by researchers as an alkylating agent for the selective modification of protein SH groups and in fluorescence studies of tryptophan residues in proteins. Because of the potential of exposure by individuals to acrylamide, effects of acrylamide in cells, tissues, animals, and humans have been extensively studied. Neurotoxicity, reproductive toxicity, genotoxicity, clastogenicity (chromosome-damaging effects), and carcinogenicity have been demonstrated to be potential human health risks that may be associated with exposure to acrylamide. In 2002, reports that acrylamide was found in plant-derived foods at levels up to 3 mg/kg, formed during their processing under conditions that also induce the formation of Maillard browning products, has resulted in heightened worldwide interest in the chemistry and safety of acrylamide. The recent realization that exposure of humans to acrylamide can come from the diet as well as from external sources has pointed to the need for developing a better understanding of its formation and distribution in food and how its presence in the diet may affect human health. A better understanding of the chemistry and biology of pure acrylamide in general and its impact in a food matrix in particular, can lead to the development of improved food processes to decrease the acrylamide content and thus the safety of the diet. To contribute to this effort, we organized a Symposium on the "Chemistry and Safety of Acrylamide in Food". The three-day Symposium, which was the first international symposium on the subject, took place in Anaheim, California on March 29-31, 2004 and attracted 34 speakers from 8 countries. Because 'acrylamide' encompasses many disciplines, in organizing the Symposium, we sought participants with a wide range of interests, yet with a common concern for basic and applied aspects of acrylamide chemistry and safety. The Proceedings of the Symposium are published as a volume in the series Advances in Experimental Medicine and Biology. We would like to emphasize the diversity of the subject matter and of the contributors' backgrounds and interests presented in this volume. The widest possible vi PREFACE viewpoints and interactions of ideas are needed to transcend present limitation in our knowledge and to catalyze progress in all areas that are relevant to the human diet. These include mechanisms of formation of acrylamide in food, distribution of acrylamide and its precursors in foods, analysis, impact of other biologically active dietary ingredients on the safety of acrylamide, toxicology, pharmacology and metabolism, epidemiology, and risk assessment. This volume brings together all elements needed for such interactions. The content includes a great variety of specific and general topics listed in the following order: toxicology/epidemiology/risk assessment; mechanisms; kinetics; analysis; acrylamide reduction; formation in different foods. It is our hope that the reader will examine not only those articles of primary interest but others as well and so profit from a broad overview. The most important function of this volume, we believe, is dissemination of insights and exchange of ideas so as to permit synergistic interaction among related disciplines. This volume brings together elements needed for such interaction. We are grateful to all contributors for their help in bringing this volume to fruition, to Carol E. Levin for assistance with formatting of manuscripts and to Wallace Yokoyama, Program Chair of the Division of Agricultural and Food Chemistry of the American Chemical Society for inviting us to organize the Symposium. We hope that "Chemistry and Safety of Acrylamide in Food" will be a valuable record and resource for further progress in this very active interdisciplinary field. We are confident that the effort of all concerned will be most worthwhile and rewarding. Mendel Friedman Don Mottram Albany, California Reading, UK January 10, 2005 January 10, 2005 CONTENTS Acrylamide in Food: The Discovery and its Implications 1 Margareta Tomqvist Acrylamide Neurotoxicity: Neurological, Morphological and Molecular Endpoints in Animal Models 21 Richard M. LoPachin The Role of Epidemiology in Understanding the Relationship Between Dietary Acrylamide and Cancer Risk in Humans 39 Lorelei A. Mucci and Hans-Olov Adami Mechanisms of Acrylamide Induced Rodent Carcinogenesis 49 James E. Klaunig and Lisa M. Kamendulis Exposure to Acrylamide 63 Barbara J. Petersen and Nga Tran Acrylamide and Glycidamide: Approach Towards Risk Assessment Based on Biomarker Guided Dosimetry of Genotoxic/Mutagenic Effects in Human Blood 77 Mathias Baum, Evelyne Fauth, Silke Fritzen, Armin Herrmann, Peter Mertes, Melanine Rudolphi, Thomas vu viii CONTENTS Spormann, Heinrich Zankl, Gerhard Eisenbrand and Daniel Bertow Pilot Study of the Impact of Potato Chips Consumption on Biomarkers of Acrylamide Exposure 89 Hubert W. Vesper, Hermes Licea-Perez, Tunde Myers, Maria Ospina, and Gary L. Mayers LC/MS/MS Method for the Analysis of Acrylamide and Glycidamide Hemoglobin Adducts 97 Maria Ospina, Hubert W. Vesper, Hermes Licea-Perez, Tunde Myers, Luchuan Mi, and Gary L. Mayers Comparison of Acrylamide Metabolism in Humans and Rodents 109 Timothy R. Fennell and Marvin A. Friedman Kinetic and Mechanistic Data for a Human Physiologically Based Pharmacokinetic (PBPK) Model for Acrylamide . 117 Melvin E. Andersen, Joseph Scimeca, and Stephen S. Olin In Vitro Studies of the Influence of Certain Enzymes on the Detoxification of Acrylamide and Glycidamide in Blood 127 Birgit Paulsson, Margareta Warholm, Agneta Rannug, and Margareta Tomqvist Biological Effects of Maillard Browning Products that May Affect Acrylamide Safety in Food 135 Mendel Friedman Acrylamide: Formation in Different Foods and Potential Strategies for Reduction 157 Richard H. Stadler Mechanisms of Acrylamide Formation: Maillard-Induced Transformations of Asparagine 171 I. Blank, F. Robert, T. Goldmann, P. Pollien, N. Varga, S. Devaud, F. Saucy, T. Hyunh-Ba, and R. H. Stadler CONTENTS ix Mechanistic Pathways of Formation of Acrylamide from Different Amino Acids 191 Varoujan A. Yalayan, CaroHna Perez Locas, Andrzej Wronowski and John O'Brien New Aspects on the Formation and Analysis of Acrylamide 205 Peter Schieberle, Peter Kohler and Michael Granvogl Formation of Acrylamide from Lipids 223 Stefan Ehling, Matt Hengel and Kakyuki Shibamoto Kinetic Models as a Route to Control Acrylamide Formation in Food 235 Bronislaw L. Wedzicha, Donald S. Mottram, J. Stephen Elmore, Georgios Koutsidis and Andrew T. Dodson The Effect of Cooking on Acrylamide and its Precursors in Potato, Wheat, and Rye 255 J. Stephen Elmore, Georgios Koutsidis, Andrew T. Dodson and Donald S. Mottram Determination of Acrylamide in Various Food Matrices Using a Single Extract; Evaluation of LC and GC Mass Spectrometric Method 271 Adam Becalski, Banjamin P.-Y. Lau, David Lewis, Stephen W. Seaman, and Wing F. Sun Some Analytical Factors Affecting Measured Levels of Acrylamide in Food Products 285 Sune Eriksson and Patrik Karlsson Analysis of Acrylamide in Food 293 Reinhard Matissek and Marion Raters On Line Monitoring of Acrylamide Formation 303 David J. Cook, Guy A. Channell, and Andrew J. Taylor Factors That Influence the Acrylamide Content of Heated Foods 317
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