Journal of Chemical Ecology

, Volume 33, Issue 7, pp 1421–1429

Byrsonic Acid—the Clue to Floral Mimicry Involving Oil-Producing Flowers and Oil-Collecting Bees


  • Mariza G. Reis
    • Instituto de QuimicaUNICAMP
    • UNIR
  • Aparecida D. de Faria
    • Instituto de BiologiaUNICAMP
    • INPA
  • Isabel Alves dos Santos
    • Instituto de BiociênciasState University of São Paulo
  • Maria do Carmo E. Amaral
    • Instituto de BiologiaUNICAMP
    • Instituto de QuimicaUNICAMP

DOI: 10.1007/s10886-007-9309-y

Cite this article as:
Reis, M.G., de Faria, A.D., dos Santos, I.A. et al. J Chem Ecol (2007) 33: 1421. doi:10.1007/s10886-007-9309-y


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.


(3R, 7R)-3,7-diacetoxy-docosanoic acidOncidinolByrsonima intermediaMalpighiaceaeTetrapedia diversipesApideaeOncidiinaeOrchidaceae

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© Springer Science+Business Media, LLC 2007