Anthocyanins as Food Colors

280 Pages·1982·13.123 MB·English

by  Pericles Markakis

ANTHOCYANINS AS FOOD COLORS
FOOD SCIENCE AND TECHNOLOGY
A SERIES OF MONOGRAPHS
Series Editors
George F. Stewart Bernard S. Schweigert John Hawthorn
University of California, Davis University of California, Davis University of Strathclyde, Glasgow
Advisory Board
C. O. Chichester Emil Mrak
Nutrition Foundation, New York City University of California, Davis
J. H. B. Christian Harry Nursten
CSIRO, Australia University of Reading, England
Larry Merson Louis B. Rockland
University of California, Davis Chapman College, Orange, California
Kent Stewart
USDA, Beltsville, Maryland
A complete list of the books in this series appears at the end of the volume.
Anthocyan i ns
as Food Colors
Edited by
Pericles Markakis
Department of Food Science and Human Nutrition
Michigan State University
East Lansing, Michigan
1982
ACADEMIC PRESS
A Subsidiary of Harcourt Brace Jovanovich, Publishers
New York London
Paris San Diego San Francisco Sao Paulo Sydney Tokyo Toronto
COPYRIGHT © 1982, BY ACADEMIC PRESS, INC.
ALL RIGHTS RESERVED.
NO PART OF THIS PUBLICATION MAY BE REPRODUCED OR
TRANSMITTED IN ANY FORM OR BY ANY MEANS, ELECTRONIC
OR MECHANICAL, INCLUDING PHOTOCOPY, RECORDING, OR ANY
INFORMATION STORAGE AND RETRIEVAL SYSTEM, WITHOUT
PERMISSION iN WRITING FROM THE PUBLISHER.
ACADEMIC PRESS, INC.
111 Fifth Avenue, New York, New York 10003
United Kingdom Edition published by
ACADEMIC PRESS, INC. (LONDON) LTD.
24/28 Oval Road, London NWI 7DX
Library of Congress Cataloging in Publication Data
Main entry under title:
Anthocyanins as food colors.
(Food science and technology)
Includes bibliographies and index.
1. Coloring matter in food. 2. Anthocyanin.
I. Markakis, Pericles. II. Series.
TP456.c65A57 664'.06 81-22902
ISBN 0-12-472550-3 AACR2
PRINTED IN THE UNITED STATES OF AMERICA
82 83 84 85 987654321
Contents
Contributors ix
Preface xi
CHAPTER 1
Chemical Structure of Anthocyanins
Raymond Brouillard
1. Introduction
II. Principal Hydroxylation, Methoxylation, Glycosylation,
and Acylation Patterns of Natural Anthocyanins 3
III. Structural Transformations in Water 7
IV. Color Stabilization Effects 26
References 38
CHAPTER 2
Copigmentation of Anthocyanins
Yoshinobu Osawa
I. Introduction 41
II. Anthocyanin Coloration of Flowers 42
III. Copigmentation in Some Detail 50
IV. Concluding Remarks 65
References 65
CHAPTER 3
Biosynthesis of AnthOcyanins
Hans Grisebach
I. Introduction 69
II. Biosynthesis of Anthocyanins in the General Context of
Flavonoid Biosynthesis 71
III. General Phenylpropanoid Metabolism 71
IV. Biosynthesis of Anthocyanins 74
v
Contents
Vl
V. Summary and Outlook 89
References 90
CHAPTER 4
Proanthocyanidins
Klaus Weinges and Franz W. Nader
I. Introduction 93
II. The Natural Leucoanthocyanidins 96
III. The Naturally Occurring Proanthocyanidinocatechins 108
IV. Prospects 120
References 120
CHAPTER 5
Distribution of Anthocyanins in Food Plants
C. F. Timberlake and P. Bridle
I. Introduction 126
II. Anthocyanins of the Dicotyledons: Archichlamydeae 127
III. Anthocyanins of the Dicotyledons: Sympetalae 143
IV. Anthocyanins of the Monocotyledons 151
V. Conclusions 156
References 157
CHAPTER 6
Stability of Anthocyanins in Foods
Pericles Markakis
I. Introduction 163
II. Chemical Structure 163
III. Enzymes 164
IV. Temperature 166
V. Light 169
VI. pH 170
VII. Oxygen 171
VIII. Ascorbic Acid 171
IX. Sugars and Their Degradation Products 172
X. Metals 173
XI. Condensation 174
XII. Sulfur Dioxide 175
References 178
Contents VII
CHAPTER 7
Analysis of Anthocyanins
F. J. Francis
I. Qualitative Analysis 182
II. Quantitative Analysis 191
III. Differentiation between Groups of Compounds 204
References 205
CHAPTER 8
The Anthocyanins of Grapes and Wines
Pascal Ribereau-Gayon
I. Introduction 209
II. Identification Methods for the Anthocyanins of Grapes 210
III. Distribution of Anthocyanins in the Different Species
of Vitis 213
IV. Differentiation of Red Wines According to Their
Anthocyanin Content 218
V. Changes in Anthocyanin Content during Grape Ripening 222
VI. Determination of Anthocyanin Content and Color in
Red Wines 226
VII. Anthocyanin Extraction from Grapes during Vinification 233
VIII. Transformation of Anthocyanins during Wine Storage
and Aging 236
IX. Conclusions 241
References 242
CHAPTER 9
Anthocyanins as Food Additives
Pericles Markakis
I. Introduction 245
II. Sources of Anthocyanins 246
III. Processing of the Raw Material 247
IV. Anthocyanin Colorants 248
V. Synthetic Flavylia 250
References 252
Subject Index 255
Genus and Species Index 261
This page intentionally left blank
Contributors
Numbers in parentheses indicate the pages on which the authors' contributions begin.
P. Bridle (125), Long Ashton Research Station, Bristol BS18 9AF,
England
Raymond Brouillard* (1), Institut de Topologie et de Dynamique des
Systemes de l'Universite Paris VII, 75005 Paris, France
F. J. Francis (181), Department of Food Science and Nutrition, University
of Massachusetts, Amherst, Massachusetts 01003
Hans Grisebach (69), Biologisches Institut II, Albert Ludwigs UniversiHit,
0-7800 Freiburg i. Br., Germany
Pericles Markakis (163, 245), Department of Food Science and Human
Nutrition, Michigan State University,East Lansing, Michigan 48824
Franz W. Nader (93), Organisch-Chemisches Institut der Universitat,
0-6900 Heidelberg 1, Germany
Yoshinobu Osawa (41), Chemical Laboratory, Meiji-Gakuin University,
Tokyo 108, Japan
Pascal Ribereau-Gayon (209), Institut d'Oenologie, Universite de Bor
deaux II, 33405 Talence, France
C. F. Timberlake (125), Long Ashton Research Station, Bristol BS18 9AF,
England
Klaus Weinges (93), Organisch-Chemisches Institut der Universitat,
0-6900 Heidelberg 1, Germany
* Present address: Universite Louis Pasteur, Institut de Chimie, 67008 Strasbourg Cedex,
France
ix