Table Of Contentrecent advances inphytochemistry
volume 30
Phytochemical
Diversityand
Redundancyin
Ecologicallnteractions
RECENT ADVANCES IN PHYTOCHEMISTRY
ProceedingsottnePhytochemicalSociety otNorthAmerica
General Editor: JohnT.Romeo, UniversityofSouth Florida, Tampa,Florida
Recent Volumes in tne Series:
Volume 21 The Phytochemlcal Effects of Envlronmental CompoundS
Proceedings ottne Twenty-sixth AnnualMeeting otthePhytochemical
Society otNorthAmerica, College Park,Maryland, July, 1986
Volume 22 Opportunltiesfor Phytochemlstry in Plant Biotechnology
Proceedings ofthe Twenty-seventhAnnualMeeting ottne
PhytochemicalSocietyofNorth America, Tampa,Florida, June,1987
Volume 23 PlantNitrogen Metabolism
Proceedings oftheTwenty-eighthAnnualMeeting otthe Phytochem;cal
Society ofNorthAmerica, lowa City, lowa, June, 1988
Volume 24 Biochemistry ofthe Mevalonlc Acid PathwaytoTerpenoidS
Proceedings ottheTwenty-ninthAnnualMeeting otthe Phytochemical
Society ofNorthAmerica, Vancouver, British Columbia, Canada,iuoe,
1989
Volume 25 Modern Phytochemical Methods
Proceedings ottne Thirtieth AnnualMeeting 01the Phytochemical
Society otNorthAmerica,Quebec City,Quebec, Canada,August, 1990
Volume 26 Phenolic Metabolism in Plants
Proceedings otthe Thirty-firstAnnualMeeting 01tne Phytochemical
SocietyofNorthAmerica, Fort Collins, Colorado, June, 1991
Volume 27 Phytochemical Potential ofTropical Plants
Proceedings 01the Thirty-secondAnnualMeetingottne Phytochemical
soctetvofNorthAmerica, Miami Beach, Florida, August, 1992
Volume 28 Genetic Engineering of PlantSecondary Metabolism
Proceedings 01the Tbitty-thirdAnnualMeeting otthePhytochemical
SocietyotNorthAmerica, Pecitic Grove, California, June-July, 1993
Volume 29 Phytochemistry of Medicinal Plants
Proceedings ottne Thirty-fourthAnnualMeeting otthe Phytochemicaf
Society otNorthAmerica, Mexico City, Mexico, August, 1994
Volume 30 Phytochemical Diverslty and Redundancy in Ecological
Interactions
Proceedings 01the Thirty-fifthAnnualMeeting ofthe Phytochemical
Society otNorthAmerica,SauftSte. Marie, Ontario, Canada,
August, 1995
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recent advances in phytochemistry
volume 30
Phytochemical
Diversity and
Redundancyin
Ecological Interactions
Edited by
John T. Romeo
UniversityofSouth Florida
Tampa,Florida
James A. Saunders
USDA
Beltsville,Maryland
and
Pedro Barbosa
University ofMaryland
College Park,Maryland
Springer Science+Business Media, LLC
Library of Congress Cataloging-in-Publication Data
On file
Cover photographs: Imago and larva of Zygaena trifolii which possesses a cyanogenic
system similar to that of its host plant Lotus. It both accumulates linamarin and lotaus
tralin from the host and synthesizes the compounds de novcr-redundancy?
Proceedings of the Thirty-Fifth Annual Meeting of the Phytochemical Society of
North America on Phytochemical Diversity and Redundancy in Ecological
Interactions, held August 12-16, 1995, in Sault Ste. Marie, Ontario, Canada
ISBN 978-1-4899-1756-0 ISBN 978-1-4899-1754-6 (eBook)
DOI 10.1007/978-1-4899-1754-6
© 1996 Springer Science+Business Media New York
Originally published by Plenum Press, New York in 1996.
Softcover reprint of the hardcover 1s t edition 1996
All rights reserved
10987654321
No part of this book may be reproduced, stored in a retrieval system, or transmitted in
any form or by any means, electronic, mechanical, photocopying, microfilming,
recording, or otherwise, without written permission from the Publisher
PREFACE
Diversitywithin and among living organisms isboth abiological impera
tive and a biological conundrum. Phenotypic and genotypic diversity is the
critical currency ofecological interactions and the evolution oflife.Thus, it is
not unexpected to find vast phytochemical diversity among plants. However,
among the most compelling questions which arise among those interested in
ecological phytochemistry isthe extent, nature,and reasons for the diversity of
chemieals in plants.
The idea that natural products (secondary metabolites) are accidents of
metabolism and have no biological function isan old one which has resurfaced
recently under a new term "redundancy." Redundancy inthe broadersense can
be viewed as duplication of effort. The co-occurrence of several classes of
phytochemieals in a given plant may be redundancy. Is there unnecessary
duplication ofchemical defense systems and ifso, why? What selective forces
haveproducedthisresult? Ontheotherhand,whydoesthesamecompoundoften
have multiple functions?
At a symposium ofthe Phytochemical Society ofNorth America held in
August 1995, in Sault Ste. Marie, Ontario, Canada, the topic "Phytochernical
Redundancy in Ecological Interactions" was discussed. The chapters in this
volume are based on that symposium. They both stimulatethought and provide
someworkinghypothesesforfutureresearch. Itisbeing increasinglyrecognized
that functional diversity and multiplicity offunction ofnatural products is the
norm rather than the exception.
BerenbaumandZangerl setthestageasthey eloquentlymake thecase that
function in nature cannot be equated with biological kill in bioassays. With
examplesdrawnfromasingledassofcompounds,thefurancoumarins,evidence
for diverse functions, multiple functions, and the importance ofsynergism in
mixtures is provided. Lindroth and Hwang, concentrating on a single genus of
plants,the aspens, show how bioactivity ofterpenoids and phenolics spans not
only families, but kingdoms. Similar examples ofmultiplicity of function are
providedby Renwiek from Pierisbutterfly/glucosinolate studies, and by Siegel
and Bush from alkaloids inendophytic grasses.
v
vi PREFACE
Hammerschmidtand Schultzdraw the parallelbetween insecticidal activ
ity and defense against pathogens, emphasizing that different approaches to
problems among plant/insect ecologists and plant pathologists have heretofore
obscuredthe ideaofthesameorsimilarcompoundshavingarangeofbiological
function. Both groups may gain insight from studies ofthe others discipline.
Isman et al., in a discussion ofcompounds from the neem tree, emphasize the
importanceofnontoxiccompoundswhichnonethelesscanenhancetoxicity.This
is a relatively new concept which further complicates already complicated
synergistic effects. It needs further attention. Cates' long-term study of the
unique pine/sawfly interactiondemonstrates convincinglythat interactions me
diated by chemiealsare neversimple,and that many relatively commonnatural
productsact inconcert,possiblywith commonproductsofprimary metabolism.
Nahrstedt'spapershowingthat an insectmakes atoxic cyanogenwhich it
can also accumulate from itshost plant puts still adifferent twist on the debate.
Is such duplication ofeffort redundancy in the narrow sense or an expanded
functional role? In the same vein, the diversity of mechanisms which are
responsibleforsystemicandnon-systemicresistancetopathogenscanbeviewed
as either"redundant"or adaptive to a variety ofselectivepressures.The papers
by Constabel et al. and Uknes etal. are both enlighteningand perplexing in this
regard.
Finally, the ideas ofcomplexity theory, made accessible in the paper by
Jarvis and Miller, and the redundancy defense, here further refined by Firn and
Jones, provoke alivelydebate which ultimately may help ecologistsand phyto
chemists alike refine their ideas about the ecological functions ofnatural prod
ucts.Whilethe papersinthis volumego alongway towardssolidifyingthe case
for natural product functional diversity and multiplicity, they also emphasize a
complexity of nature that is perhaps too convoluted and too varied to be
explained by any singleterm, be itdiversity,redundancy,or any new one on the
horizon!
The senior editor expresses gratitude to Dawn McGowan for excellent
technical expertiseinthe preparationofthis volume.Wehave madean effort in
all papers in this volume to emphasize the term "natural product" in lieu ofthe
outdated term "secondary metabolite."
John T.Romeo. University0/South Florida
James A.Saunders, USDA,Beltsville
Pedro Barbosa, UniversityofMaryland
CONTENTS
I. Phytochemical Diversity: Adaptation or Random Variation?
May R. Berenbaumand Arthur R.Zangerl
2. Diversity, Redundancy, and Multiplicity in Chemical Defense
Systems ofAspen 25
Richard L. Lindroth and Shaw-Yhi Hwang
3. Diversity and Dynamics ofCrucifer Defenses against Adults and
Larvae ofCabbage Butterflies ......................... 57
J.A.A. Renwiek
4. DefensiveChemieals inGrass-Fungal Endophyte Associations 81
Maleolm R. Siegel and Lowell P.Bush
5. Multiple Defensesand Signals in Plant Defense against Pathogens
and Herbivores 121
Ray Hammerschmidt and Jack C. Schultz
6. Phytochemistry ofthe Meliaceae:So Many Terpenoids, So Few
Insecticides 155
Murray B. Isman, Hideyuki Matsuura, Shawna MacKinnon,
Tony Durst, G. H.Neil Towers, and John T. Arnason
7. The Role ofMixtures and Variation in the Production of
Terpenoids in Conifer-Insect-Pathogen Interactions 179
Rex G.Cates
8. Relationships between the Defense Systems ofPlants and Insects:
The Cyanogenic System ofthe Moth Zygaena trifolii .....217
AdolfNahrstedt
vii
viii CONTENTS
9. Polyphenol Oxidase as aComponentofthe Inducible Defense
Response inTomato against Herbivores 231
C.Peter Constabel, Daniel R.Bergey, and Clarence A. Ryan
10.The Role ofBenzoic Acid Derivatives in Systemic Acquired
Resistance 253
Scott Uknes, ShericcaMorris, Bernard Vernooij, and John Ryals
11.Natural Products, Complexity, and Evolution 265
Bruce B.Jarvis and J.David Miller
12. AnExplanation ofSecondary Product"Redundancy" 295
Richard D.Firn and Clive G.Jones
Index 313
Chapter One
PHYTOCHEMICAL DIVERSITY
Adaptation or Random Variation?
May R.Berenbaum and ArthurR.Zangerl
DepartmentofEntomology
320 Morrill Hall
University ofIllinois
505 S.Goodwin, Urbana,Illinois 61801-3795
Introduction .................................................... I
Plant "Screening" vsInsecticide Screening 2
Parsnipsas Paradigms-Why SoMany Furanocoumarins? 4
Historical Considerations " 5
Biosynthetic Considerations 6
Activities ofFuranocoumarinsAssayedAlone ................... 7
Activities ofMixtures ofFuranocoumarins 12
Detoxification Systems andTheirContribution tothe Evolution of
Chemical Diversity ...................................... 15
Does Common Sense Prevail? ..................................... 16
INTRODUCTION
Thespectaculardiversification ofplantsecondary metabolismhasprompted
a century ofspeculation about its adaptive significance.l'" For much ofthe past
hundred years ithas been thought that natural selection effected by consumers is
thedrivingforcemaintainingthatdiversity.JonesandFirn8,however,recentlyhave
suggested that "theevolution ofplant defence may...have proceeded independent
ofconsumeradaptation." In other words, natural products may be maintained by
plantsnotdue toanyselectiveadvantage withrespect toherbivory thataccrues to
genotypes that manufacture them but rather because "plants with ahigh absolute
diversity ofsecondary metabolites have agreater probabilityofproducingone or
moreactivecompounds atanytimethanplantswithalowdiversity."
PhytochemicalDiversityandRedundancyinEcologicallnteractions,
edited byRomeoetal.,Plenum Press,NewYork,1996
