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

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

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

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

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!

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