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Drakolide Structure-activity Relationships for Sexual Attraction of Zeleboria Wasp Pollinator

Bohman, Bjorn; Tan, Monica M. Y.; Flematti, Gavin; Peakall, Rod

Description

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...[Show more]

dc.contributor.authorBohman, Bjorn
dc.contributor.authorTan, Monica M. Y.
dc.contributor.authorFlematti, Gavin
dc.contributor.authorPeakall, Rod
dc.date.accessioned2024-04-03T01:25:22Z
dc.identifier.issn0098-0331
dc.identifier.urihttp://hdl.handle.net/1885/316483
dc.description.abstractOrchids 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.
dc.format.mimetypeapplication/pdf
dc.language.isoen_AU
dc.publisherPlenum Publishing Corporation
dc.rights© 2022 The authors
dc.sourceJournal of Chemical Ecology
dc.subjectDrakaea 
dc.subjectDrakolide
dc.subjectβ-Ketolactone
dc.subjectPyrazine
dc.subjectSexual deception
dc.subjectStructure-activity relationship 
dc.subjectPollination chemistry
dc.titleDrakolide Structure-activity Relationships for Sexual Attraction of Zeleboria Wasp Pollinator
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume48
dc.date.issued2022
local.identifier.absfor310300 - Ecology
local.identifier.ariespublicationu9511635xPUB2296
local.publisher.urlhttps://link.springer.com/
local.type.statusPublished Version
local.contributor.affiliationBohman, Bjorn, College of Science, ANU
local.contributor.affiliationTan, Monica M. Y., The University of Western Australia
local.contributor.affiliationFlematti, Gavin, University of Western Australia
local.contributor.affiliationPeakall, Rod, College of Science, ANU
local.description.embargo2099-12-31
dc.relationhttp://purl.org/au-research/grants/arc/LP130100162
dc.relationhttp://purl.org/au-research/grants/arc/DP150102762
dc.relationhttp://purl.org/au-research/grants/arc/DE160101313
local.bibliographicCitation.startpage323
local.bibliographicCitation.lastpage336
local.identifier.doi10.1007/s10886-021-01324-4
dc.date.updated2022-11-13T07:19:47Z
CollectionsANU Research Publications

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