Martine Hossaert-McKey - BIOTEC · Martine Hossaert-McKey 9Centre d'Ecologie Fonctionnelle et...
Transcript of Martine Hossaert-McKey - BIOTEC · Martine Hossaert-McKey 9Centre d'Ecologie Fonctionnelle et...
Martine Martine HossaertHossaert--McKeyMcKey
Centre d'Ecologie Fonctionnelle et Evolutive, CNRS Montpellier
Equipe Coévolution
Director of Research Group (GDR-CNRS) on Chemical Ecology of Biotic Interactions
NaturalNatural productsproducts : : WhyWhy studystudy themthem in Naturein Nature??
Why do they occur ?
Why are they found where they are ?
Why to they have the properties they have ?
Where should we look to find new ones ?
Screening ?
TheoreticalTheoretical reasonsreasons to to expectexpect thatthat screeningscreeningalonealone shouldshould notnot bebe an efficient an efficient approachapproach
Screen for what? …Physiological activity in humans? Most organisms would have little use for such products
A large proportion of natural products may lack activity and have no apparent function
Functioning may sometimes depend on mixes of products. Screening all possible mixes is an unrealistic goal
Sampling for natural products with biological activity relevant to humans could be :
random (screnning)based on chemotaxonomyecology-drivenethnobiology-driven
""Natural productsNatural products" : " : Products of natural selectionProducts of natural selection
The biomimicry principle : Natural selection has had millions of years to invent solution to problems. Mimicking nature's inventions is often the fastest way we can solve problems.
Shark skin and high-performance swimsuits
Butterfly "cocoons" and a new generation of glues
Natural products are also chemical mediators of biotic interactions.
The The naturalnatural usefulness of natural productsusefulness of natural products
Nature itself has a big new problem, imposed by man: how to survive when the interactions between plants and animals that underpin nature are themselves under threat.
Biotic interactions: pollination, seed dispersal, protection, defense
Natural products are chemical mediators of these interactions
WhyWhy studystudy naturalnatural productsproducts in Nature in Nature ??
Biotic interactions are the foundation of
ecosystems
Natural products are key to conserving
biological diversity
Implications for Chemistry
Natural combinatorial chemistry generates combinatorial chemical libraries
Pupal defensive secretion of the bean beetle Epilachna varivestis
A Library of DefensiveMacrocyclic Polyamines
The combinatorial assembly of these simple building blocks generates a high degree of structural diversity, which is further increased by slow, spontaneous intramolecularrearrangement of the macrocycles.
Schroeder et al. 1998Science
GDR on GDR on ChemicalChemical EcologyEcology ofof BioticBioticInteractionsInteractions
Functional Ecology of chemical mediation
Chemical mediation and Social Insects
Chemical mediation and speciation
Chemical mediation and genomics
Chemical mediation and mutualism
GDR on GDR on ChemicalChemical EcologyEcology ofof BioticBioticInteractionsInteractions
Functional Ecology of chemical mediation
Chemical mediation and Social Insects
Chemical mediation and speciation
Chemical mediation and genomics
Chemical mediation and mutualism
N-(17-hydroxylinolenoyl)-L-glutamine
Volicitin - A natural pesticide
Figure from Farmer 1997, ScienceAlborn et al. 1997Science
Volatil signals used by parasitoids
Healthy plant volatiles
Hebvivore volatiles
Constitutive volatiles
Induced volatiles
Lepidoptera
A. M. Cortesero, Univ. Rennes
Parasitoid
Trybliographa rapae
Brassica campestris
Modèle biologique
Delia radicum
Endoparasitoïde of thelarvae of Delia
A. M. Cortesero, Univ. Rennes
BioticBiotic defensedefense in in antant--plantplant mutualismmutualism
AntAnt--plantsplants
MethylMethyl salicylatesalicylate
Characteristic sweet odour; highly volatileLinked to chemical relatives with intense diverse functions (e.g., salicylic acid)Widely used as a chemical "messenger" in interactions between plants and animals
ProtectionProtection
AntAnt--plantsplants
odour : 30% of methylsalicylate
methyl salicylate guidesthe ants
methyl salicylate mightbe used to maintin nesthygiene
Brouat et al. 2000
GDR on GDR on ChemicalChemical EcologyEcology ofof BioticBioticInteractionsInteractions
Functional Ecology of chemical mediation
Chemical mediation and Social Insects
Chemical mediation and speciation
Chemical mediation and genomics
Chemical mediation and mutualism
TermitesChemical signature, speciation and colony closure
A. G. Bagnères
NJ tree inferred from ND1-16s sequence with R. santonensis as an outgroup. Sequences have been collapsed to haplotypes. Numbers above branches indicatebootstrap support percentage over 70% in 1000 replicates. Kutnik et al. 2004, Molecular Ecology in press.
R. banyulensis
R. banyulensis
0.01
SGH 26h4 17,18,21,22,24,25,27,33 PRE 20h1 1-7,10-12,14,15,32
h2 8,9,16,19,13,23,30,31h6 44-46
CRM 38h5 41-42
h7 36,37CRV 28
h8 39,53COL,47h3 29,34,35CHI 43LORA 40
BEL 54VAL 55CPL VBEZ IIh10 I,V-IX
h9 III,IVMIJ 48
ATQ 50SAL 52MAL 49
PALa 51aPALb 51b
R. santonensis
85
80
97
77
99
R. grassei
Phylogeny (sequences ND1-16s ) : 2 mitotypes
Kutnik et al, Molecular Ecology, 2004.
A. G. Bagnères
3836343230282624222018160RT [min]
Reticulitermes banyulensis
3836343230282624222018160RT [min]
Reticulitermes grassei
172 colonies
2 chemotypes
Phylogeography of R. grassei et R. banyulensisPhD Magdalena Kutnik
A. G. Bagnères
GDR on GDR on ChemicalChemical EcologyEcology ofof BioticBioticInteractionsInteractions
Functional Ecology of chemical mediation
Chemical mediation and Social Insects
Chemical mediation and speciation
Chemical mediation and genomics
Chemical mediation and mutualism
Roses and Parfumes
P. Hugueney, ENS. Lyon
Esterase : O-méthyltransférase (OMT)
OH
cis-3-hexenol
Géraniol
H3CO OCH3
CH3
diméthoxytoluène
HO OH
CH3
H3CO OCH3
OCH3
1,3,5-triméthoxybenzène
OMT ?
P. Hugueney, ENS Lyon
Modèles 3D des OOMT1 et OOMT2
OOMT1 OOMT2
H3CO OCH3
CH3
3,5-diméthoxytoluène
HO OCH3
CH3
orcinol
HO OH
CH3
MHTDMT
OOMT1 OOMT2
P. Hugueney,ENS Lyon
GDR on GDR on ChemicalChemical EcologyEcology ofof BioticBioticInteractionsInteractions
Functional Ecology of chemical mediation
Chemical mediation and Social Insects
Chemical mediation and speciation
Chemical mediation and genomics
Chemical mediation and mutualism
Thailand represents unique opportunities Thailand represents unique opportunities for studying chemical ecologyfor studying chemical ecology
Figs and their pollinators: Meeting ground of two fig floras/fig wasp faunas:
Continental Asia (subtropical China and southeast Asia) : Hotspot of biodiversitySundaland (southern Thailand southward)
Orchids and their pollinators:Great diversity of terrestrial and epiphytic orchids in Thailand
Example: Figs and their pollinators, a keystone mutualism
FigsWasps
Pollination
Breeding sites Fruit-eatinganimals
Theentire
food web
90% of tropical trees and vines
An essential lean-seasonresource
M. Hossaert-McKeyCEFE Montpellier
HowHow wasps wasps findfind theirtheir figsfigs isis keykey questionquestion
G. MichaloudCNRS Montpellier
Olfactory signals emitted by receptive figs
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c:\documents martine\chromato-integrés-janv\fhisp35-mal9.run
WI:2 WI:4 WI:8 WI:4 WI:8WI:4
M. Hossaert-McKeyCEFE Montpellier
A sample of our database on volatile compounds found in figs Compound
Spectrum
Formula
Molecular mass
Benzene, 1,3-dimethyl 91, 106(60) / 77(15), 65(15), 39(15) C8H10 106 alpha-Pinene 93, 77(51) / 39(28), 10(25), 121(24), 136(24) C10H16 136 Camphene 93, 121(75) / 79(28), 67(26), 39(25), 107(25) C10H16 136 Sabinene 93, 77(70) / 39(27) C10H16 136 beta-Pinene 93 / 77(49), 39(48), 69(21) C10H16 136 beta-Myrcene 93, 41(99), 69(75) / 53(25) C10H16 136 3-Hexen-1-ol-acetate 67, 43(65) / 82(40) C8H14O2 142 alpha-Phellandrene 93, 39(67), 77(65) C10H16 136 p-cymene 119, 134(52) / 91(48) C10H14 134 Limonene 67, 93(75), 39(52), 57(51) / 79(48) C10H16 136 beta-phellandrene 93, 77(60) / 39(30), 105(25) C10H16 136 Ocimene 93, 79(51) / 39(28), 105(27), 121(25), 69(24) C10H6 136 Gamma- terpinene 93, 136(70), 77(65), 121(50) / 39 (25) C10H16 136 cis-Linalool oxide 59, 93(80), 43(78), 67(60) / 79(48) C10H18O2 170 trans-Linaloloxide 59, 43(80), 94(75), 79(52) / 111(48) C10H18O2 170 Methyl-Benzoate 105, 77(70) / 136(45) C8H8O2 136 Linalool 43, 93(90), 71(80), 55(75) / 121(49) C10H18O 154 Perillene 69, 41(65) / 135(25) C10H14O 150 2,6-Dimethyl-1,3,5,7-octatetraene, E 91, 119(73), 134(70) / 77(45) C10H14 134 Ethyl Benzoate 105, 77(60) / 122(49) C9H10O2 150 Naphtalene 128 / 102(20), 50(15), 63(10) C10H8 128 Indole 117, 90(75) / 63(25) C8H7N 117 alpha-Cubebene 161, 105(75), 119(74), 81(65) / 91(49) C15H24 204 alpha-Ylangene 161, 105(72) , 204(65), 119(55), 91(150) C15H24 204 Anastreptene 161 / 105(49), 204(48) alpha-Copaene 161, 105(75), 119(74) / 91(49) C15H24 204 beta- Bourbonene 81, 123(98), 161(70) / 91 (35), 39(33) C15H24 204 beta- Cubebene 161, 91(60), 119(59) beta-Elemene 67, 93(90), 79(75), 107(74), 39(55) C15H24 204 beta- Begamotene 119, 91(80) / 77 (45) alpha-Gurjunene 204, 161(80), 189(76), 105(74), 119(51) C15H24 204 alpha-cis-Bergamotene 119, 93(80), 41(55) / 77(48) C15H24 204 Italicene 105, 119(99), 161(85), 91(55) ? ? beta-Caryophyllene 91, 133(98), 105(75), 79(74), 39(73) C15H24 204 beta-Ylangene 161 / 204 (45), 91(30) gamma-Elemene 93, 121 (90), 188(85), 67(80) Aromadendrene 93, 121 (90), 188(85), 67(80) C15H24 204 Selina-4-(15)-5-diene 161 / 105(30),119(25) alpha-trans-Bergamotene 119, 93(80), 41(55) / 77(49) C15H24 204 Selina-4-(15)-6-diene 161 / 105(30), 119(25) Cadina-3,5-diene 69, 41(90), 91(80) beta-Farnesene-(E) 69, 91(95), 41(90), 161(77) C15H24 204 alpha-Humulene 93, 147(60) / 91(49) C15H24 204 allo-Aromadendrene 91,161,105(85),133(84),39(75) C15H24 204 epsilon-Murolene 161 / 91(45), 105(40)
Grison L. Greeff et al. Phytochemistry
Pollination biology of Thailand orchids Pollination biology of Thailand orchids : : Exceptional opportunities to study another Exceptional opportunities to study another
exceptional groupexceptional group
Orchids : the most species-rich flowering plant familyIntricate and specific pollinator mechanismsMaintaining plant-pollinator interactions is key to conserving endangered orchid species
0 20% 40% 60%0 20% 40%0 20% 40% 60%a- Pinèneb-PinèneSabinèneMyrcèneLimonène
1,8 CinéoleEucalyptol
Benzène acetaldehydeCis-hydrate Sabinène
Oxyde LinalolAlcanoïde (?)
LinalolUndecane
Nonanala-Camphonène
PinocarvoneMethyl-SalycilateEthylacetophenone
Terpénoïde (?)m- Myrcène
Methyldodecaneb-CaryophyllèneCaryophyldienol
L'hybridex Orchis bergonii
Orchis antropophora
Orchissimia
Proportion relative des composés présents dans l'extrait (%)
Orchids and novelties in Chemistry
B. Schatz, CEFE Montpellier
Thank you!