Bioactive Volatile Compounds from Plants

312 Pages·1993·24.01 MB·English

by  Roy Teranishi

ACS SYMPOSIUM SERIES 525
Bioactive Volatile Compounds
from Plants
Roy Teranishi,
EDITOR
Agricultural Research Service
org 001 U.S. Department of Agriculture
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San Francisco, California
April 5-10, 1992
American Chemical Society, Washington, DC 1993
In Bioactive Volatile Compounds from Plants; Teranishi, R., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1993.
Library of Congress Cataloging-in-Publication Data
Bioactive volatile compounds from plants / Roy Teranishi,
Ron G. Buttery, Hiroshi Sugisawa
p. cm.—(ACS Symposium Series, 0097-6156; 525).
"Developed from a symposium sponsored by the Division of
Agricultural and Food Chemistry at the 203rd National Meeting of
the American Chemical Society, San Francisco, California, April
5-19, 1992."
Includes bibliographical references and indexes.
org 001 ISBN 0-8412-2639-3
s.acs.25.fw 1. Essences and essential oils—Congresses. 2. Plant bioactive
ub05 compounds—Congresses. 3. Plants—Analysis—Congresses.
p://p993- I. Teranishi, Roy, 1922- . II. Buttery, Ron G. III. Sugisawa,
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ded on Copyright © 1993
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PRINTED IN THE UNITED STATES OF AMERICA
In Bioactive Volatile Compounds from Plants; Teranishi, R., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1993.
1993 Advisory Board
ACS Symposium Series
M. Joan Comstock, Series Editor
V. Dean Adams Bonnie Lawlor
University of Nevada— Institute for Scientific Information
Reno
Douglas R. Lloyd
Robert J. Alaimo The University of Texas at Austin
Procter & Gamble
Pharmaceuticals, Inc. Robert McGorrin
Kraft General Foods
org 001 Mark Arnold
bs.acs.525.fw University of Iowa JPulalniut sS cJi.e nMceesn Inn stitute,
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p://p993- David Baker U.S. Department of Agriculture
12 | htt1/bk-1 University of Tennessee Vincent Pecoraro
2002 Arindam Bose University of Michigan
42 on June 20, 1993 | doi: 10.1 RNPfaoizvbearel rRCt eeFsne.t arBarclr haR dLeysae,ba oJrcrra.h t ory MDealmrsohnatl lL Pabhoilrlaitposri es
oaded by 89.163.35.ation Date: April 6, MNDaeatnirognnaiasrl e WSt cA.i eH.n cCeesa svF aonunaduagthio n AMNG.oe arTcotahrrlgu aCesmt aeWraro nCl.i noSRalcl oehSgbwteae taretrs tUz niversity
wnlblic Lehigh University
DoPu John R. Shapley

Hiroshi Ito University of Illinois
IBM Almaden Research Center at Urbana—Champaign
Madeleine M. Joullie L. Somasundaram
University of Pennsylvania Ε. I. du Pont de Nemours and Company
Gretchen S. Kohl Peter Willett
Dow-Corning Corporation University of Sheffield (England)
In Bioactive Volatile Compounds from Plants; Teranishi, R., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1993.
Foreword
lHE ACS SYMPOSIUM SERIES was first published in 1974 to
provide a mechanism for publishing symposia quickly in book
form. The purpose of this series is to publish comprehensive
books developed from symposia, which are usually "snapshots
in time" of the current research being done on a topic, plus
some review material on the topic. For this reason, it is neces
org 001 sary that the papers be published as quickly as possible.
s.acs.25.fw Before a symposium-based book is put under contract, the
ub05 proposed table of contents is reviewed for appropriateness to
p://p993- the topic and for comprehensiveness of the collection. Some
12 | htt1/bk-1 proaupnedrs ouatr et heex sccluodpeed o fa tt heth viso lpuomien.t , Ina nadd doittihoenr,s a adrrea fta dodfe eda ctho
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20 paper is peer-reviewed prior to final acceptance or rejection.
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M. Joan Comstock
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In Bioactive Volatile Compounds from Plants; Teranishi, R., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1993.
Preface
VOLATILE COMPOUNDS FROM PLANTS, especially from flowers and
fruit, have interested humans since ancient times. In perfumery and fla
vor chemistry studies, tens of thousands of compounds have been identi
fied and correlated to characteristic odors.
Studies of volatile compounds in relation to humans have extended
from simple olfactory research to examinations of medicinal properties
and physiological and psychological effects. Plant-insect research is now
under way to correlate volatile compounds from plants to insect
responses, such as attraction or repulsion.
org 001 With the advent of the condenser, humans began isolating essential
acs.5.pr oils. Because of harsh distillation conditions, some essential oils do not
ubs.052 have the odor qualities of fresh, living plants. Modern headspace isola
p://p993- tion methods and modern analytical instruments, which require very small
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21 aromas of living flowers and fresh fruits and vegetables. Studies that
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63.35.pril 6, not to those found in most distilled essential oils.
1A In this book, internationally known perfumery and flavor chemists
y 89.ate: from industry, government, and academia present the latest findings of
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Do Pu ROY TERANISHI HIROSHI SUGISAWA
Agricultural Research Service Professor Emeritus
U.S. Department of Agriculture Department of Bioresource Science
800 Buchanan Street Kagawa University, Miki-cho
Albany, CA, 94710 Kagawa 761-07, Japan
RON G. BUTTERY
Agricultural Research Service
U.S. Department of Agriculture
800 Buchanan Street
Albany, CA, 94710
August 19, 1992
ix
In Bioactive Volatile Compounds from Plants; Teranishi, R., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1993.
org 001 We dedicate this volume to Peace
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In Bioactive Volatile Compounds from Plants; Teranishi, R., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1993.
Chapter 1
Bioactive Volatile Compounds from Plants
An Overview
Roy Teranishi and Saima Kint
Western Regional Research Center, Agricultural Research Service,
U.S. Department of Agriculture, 800 Buchanan Street, Albany, CA 94710
org 001
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u0 research on plant volatiles. Flavor chemists also study and use
p://p993- volatiles from plants to improve food quality. The vast information
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21 latest methods and equipment in sample preparation, analyses and
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41
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wnlblic highly prized, valued as precious as gold. For example, the Wise Men who came
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D P to worship the newborn Jesus brought gold, frankincense, and myrrh as gifts (2).
Incense was burned on altars to the gods (5). Perfumery was probably started
centuries before the Christian era (4). In modern times, perfumery has become a
large industry, and the intricate art, science, and technology are described in a
recent book (5). The chemistry of perfumes is complex and elegant (J, 6). Early
studies on terpenes established a better understanding of chemical bonding and
molecular rearrangements in volatile compounds (7).
Chemical Communications
Most people are pleased with the fragrance of flowers, the smell of grass,
the aroma of a pine forest. This human response is an indirect use of odors to
This chapter not subject to U.S. copyright
Published 1993 American Chemical Society
In Bioactive Volatile Compounds from Plants; Teranishi, R., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1993.
2 BIOACTIVE VOLATILE COMPOUNDS FROM PLANTS
convey a message and is the conceptual basis of the perfume industry. Chemical
communication, however, does play an explicit role in lower animal forms: in
search for food and mates, and in the avoidance of predators and danger. In the
last few decades, much has been learned about chemical communications during
insect-insect interactions and about pheromones which evoke responses among
insects of the same species (8-16). Now research emphasis is directed towards
insect-plant interactions (77, 78). In order to study and identify the volatiles from
plants which evoke various responses in insects, we must turn to knowledge gained
from perfume and flavor studies. Perfume chemists have identified and catalogued
tens of thousands of compounds; flavor chemists, about 5,000 compounds.
Experimental
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ubs.052 (19). Some recent advances in capturing volatiles from living plants are covered
p://p993- in this book. To investigate plant-insect interactions, information from such studies
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41
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wnlblic capillary columns. Results obtained with state-of-the-art separation techniques and
DoPu instrumentation for sample preparation and analyses are discussed in this book.

The differences in aromas obtained by different isolation methods are compared.
Discussion
Until recently the predominant sources of volatiles for perfumes have been essential
oils and synthetic materials. It has been shown that there are considerable
differences between volatiles from living and picked material from a certain plant
and the essential oils obtained from the same plant by distillation or extraction (19).
Because it is the dream of some perfumers to capture the freshness of living
flowers, there is a growing interest in headspace analyses of living flowers and in
vacuum headspace analyses of freshly cut flowers. Some advantages and
disadvantages of such methods are discussed in this book.
Citrus fruit juices are freshly squeezed onto some foods for tartness and for
In Bioactive Volatile Compounds from Plants; Teranishi, R., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1993.
1. TERANISHI & KINT Overview 3
fresh aroma. Extensive effort has been made to identify the compounds which
contribute to this fresh quality. Again, the advent of new methods and equipment
permit the investigation of such labile qualities. Studies of several citrus flowers
and fruit are described in several chapters of this book.
Not only are the differences in volatiles from flowers from different species
catalogued and described, but analytical methods have also been developed to such
an extent that varietal differences can be characterized. A considerable data base
is being developed for chemotaxonomy.
The use of attractive aromas from plants is not restricted to human beings.
The age of indiscrimate use of non-selective, long lasting poisons for control of
insects and weeds is slowly coming to an end after the plea by Rachel Carson (27)
to use methods more compatible with the environment in which we live. "Through
all these new, imaginative, and creative approaches to the problem of sharing our
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acs.5.ch pressures, their surges and recessions. Only by taking account of such life forces
ubs.052 and by cautiously seeking to guide them into channels favorable to ourselves can
p://p993- we hope to achieve a reasonable accommodation between the insect hordes and
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41
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wnlblic decrease or increase motor activity. Some interesting information in aromatherapy
DoPu is given in this book.

It would take many volumes to cover all of the bioactivity evoked by plant
volatiles. In this volume, we present some of the exciting topics under study on
volatiles from flowers and other parts of plants by perfume and flavor chemists,
together with the methods developed for isolating volatiles from living plants, and
a very brief look at some bioactive aspects of such volatiles. It is hoped that this
information will serve as a beginning for plant-insect interaction studies.
Literature Cited
1. Shultes, R. Ε. In Plants in the Development of Modern Medicine; Swain,
T., Ed.; Harvard University Press: Cambridge, MA, 1972; pp 103-124.
2. Matthew. In the New Testament, The Holy Bible, American Revision;
Thomas Nelson & Sons: New York, NY, 1901; 2, pp 11.
In Bioactive Volatile Compounds from Plants; Teranishi, R., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1993.