Abstract
Tetrapedia diversipes and other Apidae (Anthophoridae) may be deceived by floral similarities between Malpighiaceae and Orchidaceae of the Oncidiinae subtribe. The latter do not usually exudate floral oils. Thus, visitors may pollinate the flowers in a deceit/food/pollination syndrome. We studied the chemical compositions of Byrsonima intermedia (Malpighiaceae) floral oil and T. diversipes (Anthophoridae) cell provisions. From B. intermedia floral oil, we isolated a novel fatty acid (3R, 7R)-3,7-diacetoxy-docosanoic acid, here named byrsonic acid, and from T. diversipes cell provisions we isolated two novel fatty acid derivatives 3,7-dihydroxy-eicosanoic acid and 3,7-dihydroxy-docosanoic acid, here named tetrapedic acids A and B, respectively. The three fatty acid derivatives have common features: possess long chains (20 or 22 carbon atoms) with no double bond and either hydroxy or acetoxy groups at carbons 3 and 7. This characteristic was also encountered in the fatty acid moiety of oncidinol (2S, 3′R, 7′R)-1-acetyl-2-[3′, 7′-diacetoxyeicosanyl)-glycerol, a major floral oil constituent of several Oncidiinae species (Orchidaceae). Thus, both tetrapedic A (C20) and B (C22) could be the biotransformation products of oncidinol and byrsonic acid by T. diversipes hydrolases. These are the chemical clues for bee visitation and oil collecting from both plant species. The results indicate that the deceit/pollination syndrome should not be applied to all Oncidiinae flowers.
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Acknowledgements
The authors are indebted to FAPESP (Fundação de Amparo a Pesquisa do Estado de São Paulo—grants #01/02794-7, #98/07781-6 and #03/06624-4) and CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnologia) for scholarships and financial support. The authors are also grateful to Vera Lúcia Imperatriz Fonseca and Sandra Regina Capelari Naxara of Universidade de São Paulo-USP for the Byrsonima intermedia flowers, and Carol Collins and Volker Bittrich for critical reading and text correction.
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Reis, M.G., de Faria, A.D., dos Santos, I.A. et al. Byrsonic Acid—the Clue to Floral Mimicry Involving Oil-Producing Flowers and Oil-Collecting Bees. J Chem Ecol 33, 1421–1429 (2007). https://doi.org/10.1007/s10886-007-9309-y
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DOI: https://doi.org/10.1007/s10886-007-9309-y