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J Chem Ecol. 2012 Sep;38(9):1072-80. doi: 10.1007/s10886-012-0173-z. Epub 2012 Aug 24.

The key role of 4-methyl-5-vinylthiazole in the attraction of scarab beetle pollinators: a unique olfactory floral signal shared by Annonaceae and Araceae.

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  • 1Departamento de Química Fundamental, Universidade Federal de Pernambuco, Recife 50740-560, Brazil.


Cyclocephaline scarabs are specialised scent-driven pollinators, implicated with the reproductive success of several Neotropical plant taxa. Night-blooming flowers pollinated by these beetles are thermogenic and release intense fragrances synchronized to pollinator activity. However, data on floral scent composition within such mutualistic interactions are scarce, and the identity of behaviorally active compounds involved is largely unknown. We performed GC-MS analyses of floral scents of four species of Annona (magnoliids, Annonaceae) and Caladium bicolor (monocots, Araceae), and demonstrated the chemical basis for the attraction of their effective pollinators. 4-Methyl-5-vinylthiazole, a nitrogen and sulphur-containing heterocyclic compound previously unreported in flowers, was found as a prominent constituent in all studied species. Field biotests confirmed that it is highly attractive to both male and female beetles of three species of the genus Cyclocephala, pollinators of the studied plant taxa. The origin of 4-methyl-5-vinylthiazole in plants might be associated with the metabolism of thiamine (vitamin B1), and we hypothesize that the presence of this compound in unrelated lineages of angiosperms is either linked to selective expression of a plesiomorphic biosynthetic pathway or to parallel evolution.

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