Drakolide Structure-activity Relationships for Sexual Attraction of Zeleboria Wasp Pollinator.
Drakaea
Drakolide
Pollination chemistry
Pyrazine
Sexual deception
Structure-activity relationship
β-Ketolactone
Journal
Journal of chemical ecology
ISSN: 1573-1561
Titre abrégé: J Chem Ecol
Pays: United States
ID NLM: 7505563
Informations de publication
Date de publication:
Mar 2022
Mar 2022
Historique:
received:
05
07
2021
accepted:
13
10
2021
revised:
06
10
2021
pubmed:
1
2
2022
medline:
24
3
2022
entrez:
31
1
2022
Statut:
ppublish
Résumé
Orchids pollinated by sexual deception lure their specific male pollinators by sex pheromone mimicry. Despite the growing list of chemically diverse semiochemicals known to be involved, the chemical basis and flexibility of this extreme pollinator specificity are not fully understood. One promising but rarely applied tool is the synthesis and field testing of chemically related variants for investigating the structural specificity of the pheromone mimics. Here, we build on the discovery of the unusual semiochemical blend used by Drakaea micrantha to sexually lure its male Zeleboria thynnine wasp pollinator. This blend consists of a β-ketolactone (drakolide) and two specific hydroxymethylpyrazines, presumably drawn from two distinct biosynthetic pathways. Here, we synthesized and tested the activity of various stereo- and structural isomers of the naturally occurring drakolide. Our study confirmed that in blends with the two pyrazines, both a mixture of stereoisomers, and the specific stereoisomer of the natural drakolide, elicit high rates of landings and attempted copulations. However, in the absence of pyrazines, both the number of responses and the level of sexual attraction were significantly reduced. When structural analogs were substituted for the natural drakolide, attractiveness and degree of sexual behaviour varied but were generally reduced. Based on our findings, and prior knowledge that related hydroxymethylpyrazines are active in other Drakaea spp., we conclude that the dual sex pheromone mimicry of D. micrantha likely evolved via initial changes in just one of the two biosynthetic pathways. Most plausibly, this involved modifications in the drakolides, with the pyrazines as a 'pre-adaption' enhancing the sexual response.
Identifiants
pubmed: 35099667
doi: 10.1007/s10886-021-01324-4
pii: 10.1007/s10886-021-01324-4
doi:
Substances chimiques
Sex Attractants
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
323-336Subventions
Organisme : australian research council
ID : LP130100162
Organisme : australian research council
ID : DP150102762
Organisme : australian research council
ID : DE160101313
Informations de copyright
© 2021. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.
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