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Modem Methods of Plant Analysis New Series Volume 12
Editors H. F. Linskens, ErlangenlNijmegen/ Amherst 1. F. Jackson, Adelaide
Volumes Already Published in this Series:
Volume 1: Cell Components 1985, ISBN 3-540-15822-7
Volume 2: Nuclear Magnetic Resonance 1986, ISBN 3-540-15910-X
Volume 3: Gas Chromatography/ Mass Spectrometry 1986, ISBN 3-540-15911-8
Volume 4: Immunology in Plant Sciences 1986, ISBN 3-540-16842-7
Volume 5: High Performance Liquid Chromatography in Plant Sciences 1987, ISBN 3-540-17243-2
Volume 6: Wine Analysis 1988, ISBN 3-540-18819-3
Volume 7: Beer Analysis 1988, ISBN 3-540-18308-6
Volume 8: Analysis of Nonalcoholic Beverages 1988, ISBN 3-540-18820-7
Volume 9: Gases in Plant and Microbial Cells 1989, ISBN 3-540-18821-5
Volume 10: Plant Fibers 1989, ISBN 3-540-18822-3
Volume 11: Physical Methods in Plant Sciences 1990, ISBN 3-540-50332-3
Volume 12: Essential Oils and Waxes 1991, ISBN 3-540-51915-7
Forthcoming:
Volume 13: Plant Toxin Analysis ISBN 3-540-52328-6
Volume 14: Seed Analysis ISBN 3-540-52737-0
Essential Oils and Waxes Edited by H. R Linskens and 1. R Jackson
Contributors
R. P. Adams M. E. Crespo S. G. Deans H. E. M. Dobson P. Dunlop C. A. J. Erdelmeier A. Ghosh E. G. Hammond R. B. Inman J.F. Jackson J. Jimenez M. Kawakami A.D. Kinghorn A. Kiritsakis A. Kobayashi S. Kokkini H. F. Linskens P. Markakis J. Metzger S. Misra C. Navarro L. A. C. Pieters C. Tringali T. A. van Beek G. Vernin A.J. Vlietinck Y. Yokouchi
With 102 Figures
Springer-Verlag Berlin Heidelberg New York London Paris Tokyo Hong Kong Barcelona Budapest
Professor Dr. HANS FERDINAND LINSKENS Goldberglein 7 W-8520 Erlangen, FRG
Professor Dr. JOHN F. JACKSON Department of Viticulture, Enology and Horticulture Waite Agricultural Research Institute University of Adelaide Glen Osmond, S.A. 5064 Australia
ISBN-13 :978-3-642-84025-8 e-ISBN-13 :978-3-642-84023-4 DOl: 10.1007/978-3-642-84023-4
The Library of Congress Card Number 87-659239 (ISSN 0077-0183)
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. Duplication of this publication or parts thereof is only permitted under the provisions of the German Copyright Law of September 9, 1965, in its current version, and a copyright fee must always be paid. Violations fall under the prosecution act of the German Copyright Law.
© Springer-Verlag Berlin Heidelberg 1991 Softcover reprint of the hardcover 1st edition 1991
The use of registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use.
Product Liability: The publisher can give no guarantee for information about drug dosage and application thereof contained in this book. In every individual case the respective user must check its accuracy by consulting other pharmaceutical literature.
Typesetting: International Typesetters Inc., Makati, Philippines
31/3145-543210 - Printed on acid-free paper
Introduction
Modem Methods of Plant Analysis
When the handbook Modern Methods of Plant Analysis was first introduced in 1954 the considerations were: 1. the dependence of scientific progress in biology on the improvement of existing
and the introduction of new methods; 2. the difficulty in finding many new analytical methods in specialized journals
which are normally not accessible to experimental plant biologists; 3. the fact that in the methods sections of papers the description of methods is
frequently so compact, or even sometimes so incomplete that it is difficult to reproduce experiments. These considerations still stand today. The series was highly successful, seven volumes appearing between 1956 and
1964. Since there is still today a demand for the old series, the publisher has decided to resume publication of Modern Methods of Plant Analysis. It is hoped that the New Series will be just as acceptable to those working in plant sciences and related fields as the early volumes undoubtedly were. It is difficult to single out the major reasons for success of any publication, but we believe that the methods published in the first series were up-to-date at the time and presented in a way that made description, as applied to plant material, complete in itself with little need to consult other publications.
Contributing authors have attempted to follow these guidelines in this New Series of volumes.
Editorial
The earlier series Modern Methods of Plant Analysis was initiated by Michel V. Tracey, at that time in Rothamsted, later in Sydney, and by the late Karl Paech (1910-1955), at that time at Tiibingen. The New Series will be edited by Paech's successor H. F. Linskens (Nijmegen, The Netherlands) and John F. Jackson (Adelaide, South Australia). As were the earlier editors, we are convinced "that there is a real need for a collection of reliable up-to-date methods for plant analysis in large areas of applied biology ranging from agriculture and horticultural experiment stations to pharmaceutical and technical institutes concerned with raw material of plant origin". The recent developments in the fields of plant biotechnology and genetic engineering make it even more important for workers in the plant sciences to become acquainted with the more sophisticated methods,
VI Introduction
which sometimes come from biochemistry and biophysics, but which also have been developed in commercial firms, space science laboratories, non-university research institutes, and medical establishments.
Concept of the New Series
Many methods described in the biochemical, biophysical, and medical literature cannot be applied directly to plant material because of the special cell structure, surrounded by a tough cell wall, and the general lack of knowledge of the specific behavior of plant raw material during extraction procedures. Therefore all authors of this New Series have been chosen because of their special experience with handling plant material, resulting in the adaptation of methods to problems of plant metabolism. Nevertheless, each particular material from a plant species may require some modification of described methods and usual techniques. The methods are described critically, with hints as to their limitations. In general it will be possible to adapt the methods described to the specific needs of the users of this series, but nevertheless references have been made to the original papers and authors. While the editors have worked to plan in this New Series and made efforts to ensure that the aims and general layout of the contributions are within the general guidelines indicated above, we have tried not to interfere too much with the personal style of each author.
There are several ways of classifying the methods used in modern plant analysis. The first is according to the technological and instrumental progress made over recent years. These aspects were used for the first five volumes in this series describing methods in a systematic way according to the basic principles of the methods.
A second classification is according to the plant material that has to undergo analysis. The specific application of the analytical method is determined by the special anatomical, physiological, and biochemical properties of the raw material and the technology used in processing. This classification will be used in Volumes 6 to 8, and for some later volumes in the series.
A third way of arranging a description of methods is according to the classes of substances present in the plant material and the subject of analytiC methods. The latter will be used in this volume and for later volumes of the series, which will describe modern analytical methods for alkaloids, drugs, hormones, etc.
Naturally, these three approaches to developments in analytical techniques for plant materials cannot exclude some small overlap and repetition; but careful selection of the authors of individual chapters, according to their expertise and experience with the specific methodological technique, the group of substances to be analyzed, or the plant material which is the subject of chemical and physical analysis, guarantees that recent developments in analytical methodology are described in an optimal way.
Introduction VII
Volume Twelve - Essential Oils and Waxes
Essential oils and waxes are often classified as secondary plant products, and as a result many may be led to believe that they are of only secondary importance. However, nothing could be further from the truth. Perusal of a well-known monthly publication listing research papers of leading plant science journals shows that, currently, papers on essential oils comprise at least 10% of titles published. A total approximately 2000 papers are scanned per month. Furthermore, as the world population moves into an era with increasing demand for "organically" grown products with minimal use of manufactured chemicals both in agriculture and for other purposes, these secondary plant products are assuming a growing importance. Many of the essential oils have extremely useful properties and can be put to use in many ways. For example, terpinen-4-01, an antiseptic agent, is produced synthetically in Europe at great expense ($25000 per tonne). It also occurs naturally in Australia as an essential oil of tea tree (Melaleuca alternifolia) and is sold as tea tree oil obtained by distillation of the plant material. At present only about 50 tonnes of tea tree oil are produced annually, but it is possible that this will increase dramatically with the setting-up of tea tree plantations and as the demand increases for a natural antiseptic perceived as an "organic" cure or additive. Eucalyptus oil is another useful, socalled secondary plant product which is finding commercial markets around the world. Approximately 650 tonnes of eucalyptus oil are produced each year, a large amount considering that this involved the steam distillation of more than 15000 tonnes dry weight of eucalyptus leaves per annum.
By definition essential oils are highly volatile substances isolated by a physical method or process from an odiferous plant of a single botanical species (Encyclopaedia Britannica, 15th Edition, 1986). The oil bears the name of the plant species from which it is derived, e.g., rose oil, peppermint oil, etc. These oils were termed essential because they were thought to represent the very essence of odor and flavor. Isolation methods in the past have included steam distillation, enfleurage (i.e., extraction using fat), maceration, solvent extraction, or mechanical pressing. The oils are generally stored in the plant in glands whose function is not well understood. Chemically the essential oils are for the most part tropanes, multiple isoprenoid units, aromatics, heterocyclics, and terpenes. The genetics and biochemistry of the biosynthesis of the essential oils is reasonably well understood in some cases. For example, it is known that limonene is synthesized from geranyl pyrophosphate in the oil glands of Mentha spp., and something of the genetics of this conversion is understood. Further, we know that the various oxygenated derivatives oflimonene that make up the remainder of Mentha oil are synthesized from limonene by microsomal preparations from oil glands, which show cytochrome P-450-type mixed function oxygenase activity. Investigations of this type are underway for many of the essential oils and waxes, and so there is a great demand for reliable methods of analysis for these compounds.
Given the growing importance of essential oils and waxes, this Volume deals with the analysis of a broad spectrum of these compounds from many plant origins. Classical methods in lipid analysis, such as acid value, hydrogen value, iodine value, Reichert-Meissl value, saponification value, thyocyanogen test,
VIII Introduction
optical rotation, viscosity, refraction index, etc., are not included; they can be found in the standard methods books. We restrict ourselves to modern, recently developed analytical methods, and to oily and waxy substances of plant origin.
Commercial oils of long-standing importance such as olive oil are, of course, dealt with here, but we include also chapters on lesser-known oils such as that from thyme, tea, ginger, desert trees, eucalypt, garlic, mint, cedar, and juniper. In addition analysis of spices, seasoning, seaweeds, perfumes, liquors, and of atmospheric monoterpene hydrocarbons are to be found here, together with a treatment of pharmacological and allergenic activity analysis of plant essential oils. The volatiles offlower and pollen may be of importance in attracting bees and other insects to certain plants for pollination purposes; this topic is accordingly dealt with herein. Waxes perhaps are harder to find amongst topics in the current scientific literature, but nevertheless epicuticular waxes are included here as an ever-important topic, as well as presentation of aspects of analysis of waxes which render certain sands water-repellent in Australia! In the driest of earth's continents, this is certainly a topic of interest.
Acknowledgments. The editors express their thanks to all contributors for their cooperation, including keeping to production schedules, as well as to Dr. Dieter Czeschlik and Ms. C. WiBmeier, Ms. H. Boning, editorial office and production department of Springer, Heidelberg, for their commitment and work with this volume and others to follow in the series Modern Methods of Plant Analysis. The constant help and steady interest of Ms. Jose Broekmans, Nijmegen, is greatly acknowledged.
NijmegenjSiena and Adelaide, Summer 1991 H. F. LINSKENS
J. F. JACKSON
Contents
Olive Oil Analysis A. KIRITSAKIS and P. MARKAKIS (With 2 Figures)
1 Introduction. . . . . . . . . . . . . . . . 1
2 Quality Tests of Olive Oil-Determination of Acidity and Oxidation 1 2.1 Acidity . . . . . . . . . 1 2.2 Oxidation . . . . . . . . 2
3 Sensory Evaluation of Olive Oil 6
4 Determination of Certain Constituents of Olive Oil 10 4.1 Chlorophyll Determination . 10 4.2 Determination of Phenols . . . . . . . . 10
5 Moisture Determination. . . . . . . . . . . 11 5.1 Moisture Determination by Infrared Balance 11
6 Determination of Soap Content
7 Olive Oil Adulteration - Adulteration and Genuineness Tests. 7.1 Methods and Techniques of Detecting Adulteration . . . 7.2 Adulteration Tests Based on Color Formation . . . . . 7.3 Adulteration Tests Based on Residue or Clouding Formation 7.4 Detection of Oil Adulteration by a UV Lamp. . . . . . . 7.5 Detection of Olive Oil Purity by Infrared Spectrophotometry
References. . . . . . . . . .
Analysis of Essential Oils of Tea A. KOBAYASHI and M. KAWAKAMI (With 8 Figures)
11
12 12 13 15 17 17
19
1 Introduction. . . . . . . . . . . . . . . . 21
2 Isolation of Essential Oils . . . . . . . . . . 22 2.1 Steam Distillation Under Reduced Pressure (SDR) 22 2.2 Simultaneous Distillation and Extraction (SDE). . 22 2.3 Head Space Gas Analysis . . . . . . . . . . . 24
3 Separation and Identification of Essential Oil Components from Tea 26 3.1 Gas Chromatography . . . . . . . . . . . . . 26 3.2 Gas Chromatography-Mass Spectrometry (GC-MS) 27 3.3 Gas Chromatography-Infrared
Spectrometry-Mass Spectrometry (GC-IR-MS) . . 28
x
4 Components of the Essential Oil 4.1 Comparison of the Main Components in Various Teas. 4.2 Specific Components of the Essential Oils
5 Pattern Analyses of Gas Chromatograms
References. . . . . . . . . . . . . . .
Special Methods for the Essential Oils of the Genus Thymus M. E. CRESPO, J. JIMENEZ, and C. NAVARRO (With 5 Figures)
1 Introduction .
2 Plant Material
3 Extraction. .
4 Analytical Methodology .
4.1 Qualitative Analysis . 4.2 Quantitative Analysis
5 Conclusions
References. .
Chemical Races Within the Genus Mentha. L. S. KOKKINI (With 1 Figure)
1 Introduction. . . . . . . . . . .
2 Biosynthesis of Mentha Essential Oils
3 Chemical Races . . . . . . . . . 3.1 Oils Rich in Acyclic Compounds 3.2 Oils Rich in 2-Substituted Compounds. 3.3 Oils Rich in 3-Substituted Compounds.
4 Conclusions
References. .
Special Methods for the Essential Oil of Ginger T. A. VAN BEEK (With 8 Figures)
Contents
28 28 33
37
38
41
43
44
44
44 53
56
57
63
64
65
65 67 69
74
75
1 Introduction. . . . . . . 79
1.1 Description and Use. . . 79 1.2 Chemical Composition. . 79 1.3 Isolation, Separation and Quality Evaluation of Ginger Oil. 81
2 Traditional Methods of Extraction, Separation, and Control 81 2.1 Traditional Isolation Methods . 81 2.2 Traditional Separation Methods 81 2.3 Traditional Quality Control . . 81
Contents
3 Modern Methods of Extraction, Separation, and Identification
3.1 Introduction . . . . . . . . . 3.2 Modern Methods of Isolation 3.3 Modern Methods of Separation. 3.4 Modern Methods of Identification
References. . . . . . . . . . . . . .
GC-MS (EI, DCI, NCI, SIM) SPECMA Bank Analysis of Volatile Sulfur Compounds in Garlic Essential Oils G. VERNIN and J. METZGER (With 11 Figures)
XI
82
82 82 83 89
96
1 A Short Survey of the Chemistry of Garlic. . . . . . . . . . . . . 99
2 Analytical Methods Used for Identification of Sulfur Compounds in Garlic Essential Oil . . . .
2.1 GC-MS (EI, PCI, NCI) of G~rlic Essential Oils. 2.2 Kovats Indices as Filters and Their Properties 2.3 The SPECMA Bank. . . . . . . . . . .
3 GC-MS Analyses of Two Garlic Essential Oils Originating from France (Provence) and Mexico 3.1 Analyses and Composition. . . . . . . . 3.2 Mechanisms of Formation of Sulfide Derivatives
4 Conclusion
References. .
Analysis of Juniper and Other Forest Tree Oil R. P. ADAMS (With 16 Figures)
1 Introduction. . .
2 Sample Collection 2.1 Sampling . . 2.2 Sample Sizes . 2.3 Diurnal, Seasonal, and Ontogenetic Variation.
3 Oil Extraction . . . . .
4 Chemical Analysis . . . 4.1 Gas Chromatography
5 Component Identification 5.1 GCfMC Computer Searches
6 Applications of Terpenoid Data
6.1 Analyses of Hybridization and Introgression 6.2 Studies of Geographic Variation . . . . . 6.3 Taxon Level Differences and Evolutionary Studies.
References. . . . . . . . . . . . . . . . . . . . .
102
102 106 114
116 116 125
128
129
131
131 131 132 132
138
139 139
141 142
142
142 146 149
154
XII
Cedar Wood Oil - Analyses and Properties R. P. ADAMS (With 7 Figures)
1 Introduction. . .
2 Sample Collection
3 Oil Extraction . .
4 Chemical Analysis
4.1 Gas Chromatography
5 Identification
5.1 GCjMS ..... .
6 Properties . . . . . . .
6.1 Antimicrobial Activities 6.2 Insecticidal Activities 6.3 Termiticidal Activities
References. . . . . . . .
Analysis of Croton Oil by Reversed-Phase Overpressure-Layer Chromatography A. D. KINGHORN and C. A. J. ERDELMEIER (With 5 Figures)
1 Introduction - Overpressure-Layer Chromatography as a Separatory Technique. . . . . . . . . .
2 Phorbol Ester Constituents of Croton Oil . . . . .
3 Separation of the Phorbol Esters of Croton Oil. . .
3.1 Two-Dimensional Thin Layer Chromatography. 3.2 Reversed-Phase Overpressure Layer Chromatography
4 Summary and Conclusions.
References. . . . . . . . .
Rotation Locular Countercurrent Chromatography Analysis of Croton Oil L. A. C. PIETERS and A. J. VLIETINCK (With 4 Figures)
1 Introduction. . . . . . . . . . . . .
2 Croton Oil, the Seed Oil of Croton tiglium
3 RLCC Analysis of Croton Oil . . . . .
3.1 Introduction . .'. . . . . . . . . 3.2 Experimental Details and Discussion
4 Summary and Conclusion
References. . . . . . . .
Contents
159
161
162
166
166
166
166
167
171 171 171
172
175
175
177
177 181
183
183
185
186
187
187 188
192
192
Contents
Oils and Wa~es of Eucalypts Vacuum Distillation Methodifor Essential Oils R. B. INMAN, P. DUNLOP, and J. F. JACKSON (With 1 Figure)
1 Introduction. . . . . . . . . . . . . . . . . .
2 Chemical Composition of Eucalyptus Oils and Waxes
3 Methods of Analyses of Eucalyptus Waxes. .
4 Methods of Analysis of Eucalyptus Oils . . .
5 Vacuum Distillation Method for Essential Oils
5.1 Preparation of Leaf Powder 5.2 Distillation. 5.3 Notes
References. . . .
Analysis of Epicuticular Waxes S. MISRA and A. GHOSH (With 9 Figures)
1 Introduction. . . . . . . . .
2 Extraction of Epicuticular Wax.
3 Fractionation of Wax Components 3.1 Column Chromatography .. 3.2 Thin Layer Chromatography (TLC) .
4 Analysis of Wax Components . . . . . 4.1 Analysis of Hydrocarbon
by Gas Liquid Chromatography (GLC) 4.2 Analysis of Wax Esters . . . . . . . 4.3 Analysis of Free Alcohols and Fatty Acids 4.4 Analysis of Aldehydes . 4.5 Analysis of fj-Diketones
5 Conclusion
References. .
Analysis of Flower and Pollen Volatiles H. E. M. DOBSON (With 3 Figures)
1 Introduction. . . . . . .
2 Flower Volatile Chemistry .
3 Overview of Methodology
3.1 Volatile Collection 3.2 Volatile Analysis . 3.3 Cautionary Notes.
XIII
195
195
196
197
198
198 198 200
202
205
207
207 207 208
208
208 213 224 224 225
226
226
231
231
232
232 234 235
XIV
4 Details of Collection Methods 4.1 Extraction and Distillation . 4.2 Headspace Cold-Trapping . 4.3 Direct Headspace Sampling 4.4 Headspace Sorption . 4.5 Passive Sorption
References. . . . . . . .
Bioactivities of Diterpenoids from Marine Algae C. TRINGALI
Contents
235 235 236 237 238 248
248
1 Introduction. . . . . 253
2 Antimicrobial Activity 254 2.1 Background . . . 254 2.2 Description of the Methods 254 2.3 Antimicrobial Diterpenoids from Seaweeds. 259
3 Antialgal Activity. . . . . . 262 3.1 Background . . . . . . . . . . . 262 3.2 Description of the Method . . . . . 262 3.3 Antialgal Diterpenoids from Seaweeds 263
4 Cytotoxic Activity and Other Related Activities. 263 4.1 Background . . . . . . . . . . . . . . 263 4.2 Description of the Methods . . . . . . . 264 4.3 Cytotoxic and Antimitotic Diterpenoids from Seaweeds 267
5 Ichthyotoxicity and Other Defensive Bioactivities 269 5.1 Background . . . . . . . . . . . . . . . . . . . 269 5.2 Description of the Methods . . . . . . . . . . . . 270 5.3 Ichthyotoxic and Other Defensive Diterpenoids from Seaweeds 272
6 Molluscicidal Activity. . . . . 273 6.1 Background . . . . . . . . . . . . . 273 6.2 Description of the Methods . . . . . . 274 6.3 Molluscicidal Diterpenoids from Seaweeds 275
7 Other Bioactivity Data on Diterpenoids from Seaweeds 276
8 Concluding Remarks 276
References. . . . . . 286
Determination of Waxes Causing Water Repellency in Sandy Soils J. F. JACKSON and H. F. LINSKENS
1 Introduction. . . . . . . . . . . . .
2 Assessment of Water Repellency of Soils.
291
292
Contents
2.1 Molarity of the Ethanol Droplet (MED) Method 2.2 Capillary Rise Technique 2.3 Other Test Methods. . . . . .
3 Extraction of Water-Repellent Waxes
4 Significance and Conclusions .
References. . . . . . . . . . . . .
Analysis of Monoterpene Hydrocarbons in the Atmosphere Y. YOKOUCHI (With 8 Figures)
1 Introduction. . . . . . . .
2 Sampling and Concentration . 2.1 Adsorption Method . 2.2 Grab Sampling . . . .
3 GC, GCjMS Method . . . 3.1 Packed GCjMS (SIM) . 3.2 Capillary GC (FID) . 3.3 Capillary GCjMS. . .
4 Calibration . . . . . . .
5 Features of Atmospheric Monoterpenes
References. . . . . . . . . . . . . .
Evaluation of Antimicrobial Activity of Essential (Volatile) Oils S. G. DEANS (With 4 Figures)
1 Introduction. . . . . . . . . . . . . . . . . . .
2 Extraction of Plant Volatile Oil. . . . . . . . . . .
3 Evaluation of Antimicrobial Properties of Volatile Oils 3.1 Antibacterial Testing . . . . . . 3.2 Antifungal Testing . . . . . . .
4 Antimicrobial Activity of Volatile Oils.
5 Future Developments in Volatile Oils
References. . . . . . . . . . . . . .
Organization of Rapid Analysis of Lipids in Many Individual Plants E. G. HAMMOND
1 Introduction. . . . . . . . . .
2 Analyses for Total Lipid Content.
XV
· 292 · 292 · 293
293
294
294
· 297
· 297
· 298 · 299
300 300 300 304
305
305
307
309
309
311 311 313
315
317
318
321
322
XVI
3 Analyses for Fatty Acid Composition
4 Analyses for Glyceride Structure . .
5 Analyses for Other Lipid Constituents.
6 Analyses for Lipoxygenase .
References. . . . . . . . .
Contents
323
325
326
327
328
List of Contributors
ADAMS, ROBERT P., Plant Biotechnology Center, Baylor University, P.O. Box 97372, Waco, Texas, 76798-7372, USA
CRESPO, MARIA ESPERANZA, Dept. of Pharmacology, School of Pharmacy, University of Granada, E-18071 Granada, Spain
DEANS, STANLEY G., Dept. of Biochemical Sciences, Scottish Agricultural College, Auchincruive, Ayr KA65HW, Scotland, UK
DOBSON, HEIDI E. M., Dept. of Chemical Ecology, University of Goteborg, Reutersgatan 2c, S-41320 Goteborg, Sweden
DUNLOP, P., Dept. of Physical and Inorganic Chemistry, University of Adelaide, Adelaide, South Australia 5064, Australia
ERDELMEIER, CLEMENS A. J., Research and Development, Dr. Willmar Schwabe Arzneimittel, Postfach 410925, W-7500 Karlsruhe 41
GHOSH, AMITABHA, Dept. of Chemistry, Bose Institute, 93/1 A.P.C. Road, Calcutta 700 009, India
HAMMOND, E. G., Food Science and Human Nutrition, Dairy Industry Building, Iowa State University, Ames, Iowa 50011, USA
INMAN, Ross B., Institute for Molecular Virology, University of Wisconsin, 1525 Linden Drive, Madison, Wisconsin 53706, USA
JACKSON, JOHN F., Dept. of Viticulture, Enology and Horticulture, Waite Agricultural Research Institute, University of Adelaide, Glen Osmond, S.A. 5064, Australia
JIMENEZ, JOSE, Dept. of Pharmacology, School of Pharmacy, University of Granada, E-18071 Granada, Spain
KAWAKAMI, MICIDKO, Shion Junior College, 6-11-1 Ohmika-cho, Hitachi-shi Ibarakj-ken 319-12, Japan
KINGHORN, A. DOUGLAS, Dept. of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, m/c 781, University of Illinois at Chicago, Box 6998, Chicago, Illinois 60680, USA
KIRITSAKIS, APOSTOLOS, School of Food Technology and Nutrition, Technological Educational Institution, (TEl) of Thessaloniki, Thessaloniki, Greece
XVIII List of Contributors
KOBAYASID, AKIO, Laboratory of Food Chemistry, Dept. of Food and Nutrition Ochanomizu University, 2-1-1, Ohtsuka, Bunkyo-ku, Tokyo 112, Japan
KOKKINI, STELLA, Laboratory of Systematic Botany and Phytogeography, School of Biology, Faculty of Sciences, University of Thessaloniki, GR-54006 Thessaloniki, Greece
LINSKENS, HANS FERDINAND, Goldberglein 7, W-8520 Erlangen, FRG
MARKAKIS, P., Dept. of Food Technology, School of Food Technology and Human Nutrition, Technological Educational Inst. (TEl), Thessaloniki, Greece
METZGER, JACQUES, Organic Chemistry Laboratory A, Faculty of Sciences and Techniques of Saint-Jerome, Avenue Escadrille, Normandie-Niemen, P.O. Box 561, F-13397 Marseille CEDEX 13, France
MISRA, SUNITI, Dept. of Marine Science, University of Calcutta, 35 B. C. Road, Calcutta 700019, India
NAVARRO, CONCEPCION, Dept. of Pharmacology, School of Pharmacy, University of Granada, E-18071 Granada, Spain
PIETERS, Luc A C., Dept. of Pharmaceutical Sciences, University of Antwerp (UIA), Universiteitsplein 1, B-2610 Antwerp, Belgium
TRINGALI, CORRADO, Dipartimento di Scienze Chimiche, Universita di Catania, Viale A Doria 8, 1-95125 Catania, ltalia
VAN BEEK, TERIS A, Dept. of Organic Chemistry, Phytochemical Section, Agricultural University, Dreijenplein 8, N-6703 HB Wageningen, The Netherlands
VERNIN, GASTON, Organic Chemistry Laboratory A, Faculty of Sciences and Techniques of Saint-Jerome, Avenue Escadrille Normandie-Niemen, P.O. Box 561, F-13397 Marseille CEDEX 13, France
VLIETlNCK, ARNOLD J., Dept. of Pharmaceutical Sciences, University of Antwerp (UIA), Universiteitsplein 1, B-2610 Antwerp, Belgium
YOKOUCHI, YOKO, National Institute for Environmental Studies, 16-2, Onogawa, Tsukuba, Ibaraki 305, Japan
