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)-l-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.
A maioria dos estudos sobre polinização focalizam as interações que envolvem recompensas como néctar e pólen. Nosso grupo de pesquisa, entretanto tem se dedicado à química de recompensas florais como resinas e óleos florais. Neste trabalho, estamos relatando a composição química dos óleos florais de Oncidium pubes que contêm di e triacilglicerois nos quais o glicerol está esterificado com um ou dois resíduos de ácido acético e um ácido graxo. O padrão de substituição dos dracilgliceróis foi sugerido com base nas analises espectroscópicas e por comparação com os 3 compostos sintetisados a partir do D-manitol, ácido acético e ácido oleico Finalmente, nossos resultados forneceram evidências químicas de que a polinização de Oncidium pubes não está baseada num mecanismo de atração-engano dos visitantes florais mas na sua recompensa com lipídios florais. Este é o primeiro relato sobre a composição química dos óleos florais de Oncidium pubes (Orchidaceae).Most of the flower-pollinator interactions are based on rewards as pollen and nectar. Our group however, has been focusing on the chemical composition of unusual rewards like floral resins and floral oils. We are now reporting the chemistry of the floraloils of Oncidium pubes which are composed of diacylglycerols and triacylglycerols possessing one or two acetyl residues and one long chain fatty acid. The substitution pattern of some of the diacylglycerols was inferred to be 1, 3 based on spectroscopic analyses and comparison with 3 different synthetic compounds obtained from D-mannitol, oleic acid and acetic acid. The fatty acid residues possess double bond and/or acetoxy group as functional groups. Finally our results provided chemical evidences that pollination of Oncidium pubes is not based upon an attraction-deception system but on floral lipids and this is the first time this has ever been mentioned in the literature.
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