Pheromone Biochemistry

562 Pages·1987·36.082 MB·English

by  Glenn D. Prestwich, Gary J. Blomquist

Pheromone
Biochemistry
Edited by
Glenn D. Prestwich
Department of Chemistry
State University of New York at Stony Brook
Stony Brook, New York
Gary J. Blomquist
Department of Biochemistry
University of Nevada
Reno, Nevada
1987
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Library of Congress Cataloging in Publication Data
Pheromone biochemistry.
Includes index.
1. Insect hormones. 2. Pheromones. I. Prestwich,
Glenn D. II. Blomquist, Gary J. [DNLM: 1. Biochemistry.
2. Insects. 3. Pheromones. QP190P5422]
QL495.P48 1987 595.7Ľş42 86-30224
ISBN 0-ş2-564485-× (alk. paper)
PRINTED IN THE UNITED STATES OF AMERICA
87 88 89 90 9 8 7 6 5 4 3 2 1
To our families
Barbara, Steven, and locelyn
and
Cheri, Carianne, A.},, and Scotty
for their love and understanding
Preface
In the last three decades, chemists and biologists have developed sophisticated
techniques for determining the chemical structures of pheromones, for making
pure stereoisomers on a kilogram scale, for dissecting the behavioral sequences
elicited by pheromones, for visualizing the ultrastructural details of receptive
sensillae, and for using pheromones for mating disruption and for monitoring in
integrated pest-management schemes. Several recent books have appeared high­
lighting these successes, yet we still find ourselves a long way from a thorough
understanding of the practical use of insect sex pheromones. Until very recently
there has been a paucity of biochemical studies on pheromone-relevant mac­
romolecules which would provide a connection between small molecules and
whole organisms. Specifically, we feel that much more intensive effort is re­
quired now in the basic areas of pheromone biochemistry and neurobiology to
solve problems of biosynthesis, perception, transduction, and metabolism.
Current awareness of this new direction in pheromone research has resulted in
at least five symposia in the last two years: two within the American Chemical
Society, two in the Entomological Society of America, and one at an AAAS
meeting. The latter elicited an editorial comment in Science [226, 1343 (1985)]
by Philip Abelson, in which he voiced support for focusing attention on the
biochemical details of how pheromones and their associated macromolecules
work on a molecular level. Although *'early enthusiasm about the use of phero­
mones to control insect populations has dwindled," there is a consensus that
basic research in pheromone biosynthesis, binding, and degradation may rein-
vigorate optimism for the utility of pheromone analogs in pest management.
This book is designed as a sourcebook for the next decade of research, and we
hope it fulfills this expectation. We have assembled contributed chapters from
experts who are at the frontiers of pheromone chemistry, glandular and antennal
moöhology, neurobiology, and biochemistry. Although there is considerable
XV
xvi Preface
emphasis on the Lepidoptera, this is balanced by chapters on ticks, flies, beetles,
and even vertebrate olfactory biochemistry. We hope that researchers in the areas
of chemistry, biochemistry, entomology, neurobiology, molecular biology, en-
zymology, moöhology, behavior, and ecology will be able to use this volume as
an entry into the literature of pheromone biochemistry.
The book is divided into two major sections. The first deals with pheromone
production and its regulation in female insects, while the second covers recep­
tion, perception, and degradation of pheromones by male insects. Each author
has included a review of the literature, examples of detailed practical meth­
odology, very current and often unpublished data from their own laboratories,
and a healthy amount of inteöretation and speculation on how their particular
subdiscipline will grow interdependently with others.
The chemicals used as sex pheromones exhibit considerable diversity, reflect­
ing a variety of unique biochemical processes that occur in pheromone-producing
tissues. The biosynthetic pathways for the pheromones from a number of species
have been determined, and work is progressing toward description of the en­
zymes involved. From the results of studies to date, it appears that these specific
and unique chemicals are produced by the addition of one or two ancillary
enzymes to alter the products of normal" metabolism, rather than the elabora­
tion of an entire set of unique enzymes in the pheromone glands. Pheromone
production in many species must be under endocrine regulation to optimize
mating strategies. Products of the coöora allata, brain, and ovary have been
implicated as agents which regulate pheromone production. The studies of the
biosynthesis and regulation of pheromone production are still embryonic, and we
hope that this book will stimulate further research in this area.
In many ways, insects are ideal models for determining the details of olfactory
reception and transduction. They are easy to obtain in large numbers, and the
collection of biosynthetic and olfactory tissues is mechanically straightforward.
Most insects show strong male-female dichotomy in the production of and
response to pheromone blends. The blends are simple, and single-receptor senso­
ry cells can be located for many pheromone components. Insects grow rapidly,
and the appearance of new mRNA and new proteins for pheromone biosynthesis,
reception, and catabolism can be timed accurately. The olfactory organs are
exterior to the organism and are readily accessible for chemical, electrical, and
mechanical manipulation in experimental protocols. Olfactory mutants and a
genetically diverse population of olfactory responses and olfactant proteins are
readily identified and provide materials for uncovering the molecular biology of
pheromone-mediated behavior. The odorants are simple lipids, often a few close­
ly related components, rather than highly complex ''gestalt" mixtures. Thus,
highly specific, high-affinity receptor proteins are expected in contrast to the less
specific, lower affinity olfactory receptors in many vertebrates. Finally, many of
Preface xvii
the target insects for olfactory studies are pests of serious agricultural or medical
importance. We believe that the intellectual exercise of unraveling the olfactory
mechanism is in reality a necessity for the development of the behavior-modify­
ing agrochemicals of the future.
May 1987 Glenn D. Prestwich
Gary J. Blomquist
Acknowledgments
We owe a tremendous debt to our colleagues and co-workers for their advice
and encouragement, unpublished results, and moral support during the prepara­
tion of this book. Special Üianks are due to Ms. Marie Dippolito (Stony Brook)
for her tireless assistance in preparing the index and coordinating the contribu­
tions of the various authors. We are grateful to the authors of the individual
chapters for preparing scientifically exciting and visually stimulating contribu­
tions. Most important, we thank our mentors, postdocs, and students for making
this work fun and rewarding. Financial support to us and our laboratories by the
National Science Foundation, the National Institutes of Health, the United States
Department of Agriculture, the Herman Frasch Foundation, the Nevada Agri­
cultural Experiment Station (GJB), the Alfred P. Sloan Foundation (GDP), the
Camille and Henry Dreyfus Foundation (GDP), Rohm and Haas Co. (GDP), and
Stuart Pharmaceuticals (GDP) made the research possible and the book prepara­
tion a reality.
XIX
1
Relationship of Structure and
Function to Biochemistry in Insect
Pheromone Systems
J. H. TUMLINSON
P. E. A. TEAL
Insect Attractants, Behavior, and Basic Biology Research Laboratory
Agricultural Research Service
U.S. Department of Agriculture
Gainesville, Florida 32604
I. INTRODUCTION
Chemical cues are major sources of information used by most insects to
inteφret environmental stimuli. This reliance on chemical stimuli undoubtedly
stems from the development of chemosensory organs and cells early in evolu­
tionary history, perhaps even before the development of light-sensitive organs
(Snodgrass, 1926). Broadly speaking, these chemical stimuli are categorized as
semiochemicals. They function as pheromones when used for intraspecific com­
munication. When used at the interspecific level, they are termed kairomones
when the species responding to the chemical message benefits and allomones
when the species emitting the signal gains some advantage over the receiving
organism. There is considerable overlap between these classes, and often the
same compounds serve both intra- and interspecific functions. Therefore, in order
to elucidate the roles of individual semiochemicals it is necessary to study all
aspects of the communication system from biosynthesis of the compounds to the
perception and integration of the compounds by all of the organisms responding.
Pheromone Biochemistry Copyright © 1987 by Academic Press, Inc.
All rights of reproduction in any form reserved.
4 J. Η. Tumlinson and P. E. A. Teal
Of the three classes of semiochemicals mentioned above, pheromones are the
most extensively studied. Although all insect orders use pheromones in commu­
nication, the highly social Hymenoptera and Isoptera have developed the most
complex and sophisticated pheromone systems. In fact, Blum (1974) suggests a
strong evolutionary relationship between the development of insect societies and
diversification of pheromone communication. Among subsocial insects, phe­
romones have been shown to play major roles in (1) the initiation of gregarious
behavior during group oviposition among certain mosquitoes (Hudson and
Mclintock, 1967) and the desert locust Schistocerca gregaria (Forsk.) (Norris,
1963); (2) the formation of aggregations at food sites, particularly among
scolytid beetles (Birch, 1984) and Drosophila species (Bartelt et al., 1985); (3)
dispersal behavior among generally gregarious species during predator attack
(Nault and Phelan, 1984); (4) the synchronization of gamete maturity among
species exhibiting aggregative behaviors (Blum, 1974); and (5) mate attraction
among species that maintain a solitary life style.
According to Inscoe (1977), conspecific attractancy among lepidopteran spe­
cies has been known since 1690, when John Ray reported several male Biston
betularia (L.) flying around a caged female. This knowledge of the attractive
capacity of female Lepidoptera also was used by such great naturalists as Fabre
for collection of rare specimens; the procedure used was essentially the same as
that of Ray (Kettlewell, 1946; Inscoe, 1977). The use of live females for popula­
tion monitoring of the gypsy moth, Lymantria dispar (L.), began in 1914, but by
1920 the females had been replaced by crude abdominal tip extracts that re­
mained active for longer periods than females (Collins and Potts, 1932). At­
tempts to isolate the chemical components of lepidopteran sex attractants also
began in the 1920s. Unfortunately, the methods then available for chemical
analysis were not adequate, requiring large sample quantities and necessitating
continuous rearing of large numbers of insects. As a consequence, little headway
was made. The first sex pheromone identified was that of Bombyx mori (L.), the
silkworm moth, by Butenandt et al. (1959). The elucidation of bombykol
[(£,Z)-10,12-hexadecadien-l-ol] required 20 years and 500,000 female abdo­
mens.
Subsequent to the identification of ''bombykol," considerable emphasis was
placed on the identification of pheromone components of pest Lepidoptera, and,
in 1966, (Z)-7-dodecenyl acetate was identified as the sex pheromone of the
cabbage looper moth (Berger, 1966). Following this, single components of the
pheromones of a number of noctuid and tortricid moths were identified. This led
to the ''magic bullet'' theory of pheromone communication, which hypothesized
that every insect species used a single compound for pheromone communication
and that each species was isolated from closely related species by differences in
the functionality or number and geometry of double bonds within the pheromone
1. Pheromone Structure, Function, and Biochemistry 5
molecule. This hypothesis was generally accepted by many researchers working
on Lepidoptera until about 1970. However, early work on bark beetles by Sil-
verstein et al (1966) in which three teφenes, (.S)-(-)-ipsenol (I), (S)-{+)-
ipsdienol (II), and (5)-(+)-d5-verbenol (III), were identified as a synergistic
pheromone blend for Ips paraconfusus Lanier, indicated that multicomponent
pheromones were used by Coleoptera. This has since been shown to be true for
most insects, and now single-component pheromones are the exception rather
than the rule.
I II
Our knowledge of the chemistry, behavior, physiology, and biochemistry of
insect communication systems has increased dramatically over the past 25 years.
Early studies were aimed at two different goals. The first was development of a
basic knowledge about the biological aspects of pheromone communication, as is
indicated by the early work of Shorey and co-workers (e.g., Shorey, 1964;
Shorey and Gaston, 1965). The second area was the identification and synthesis
of pheromones based on simple bioassays. The bioassays used for these studies
tended to rely on single behaviors, such as flight or clasper extension, of groups
of insects and failed to monitor observations of the whole range of reproductive
behaviors exhibited by individual males. Additionally, the chromatographic and
spectroscopic instrumentation available in the 1960s was incapable of resolving
complex isomeric mixtures or of detecting minor components present in only
nanogram amounts. Thus, usually only the components present in greatest quan­
tity were identified. This is illustrated by the identification of (Z)-7-dodecenyl
acetate as the sex pheromone of the cabbage looper moth (Berger, 1966). While
this compound is an effective attractant for males for this species, the insects do
not exhibit the entire range of behaviors performed in response to females. It was
not until 1984 that Bjostad et al. (1984) and Linn et al (1984) accurately defined
the complete pheromone blend of this insect. The additional components identi­
fied by Bjostad et al. (1984) are present in very small amounts and were not
found until studies on biosynthesis identified the precursors of the additional
components. This demonstrates the need for studies on all aspects of semiochem-
ical-mediated biology.
The next step in the evolution of studies on pheromone communication came