Byrsonic acid - The clue to floral mimicry involving oil-producing flowers and oil-collecting bees
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 th...
| Autor principal: | Reis, Mariza Gomes |
|---|---|
| Outros Autores: | Faria, Aparecida D., Alves-dos-Santos, Isabel, Amaral, Maria do Carmo Estanislau do, Marsaioli, Anita |
| Grau: | Artigo |
| Idioma: | English |
| Publicado em: |
Journal of Chemical Ecology
2020
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| Acesso em linha: |
https://repositorio.inpa.gov.br/handle/1/18648 |
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oai:repositorio:1-18648 |
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oai:repositorio:1-18648 Byrsonic acid - The clue to floral mimicry involving oil-producing flowers and oil-collecting bees Reis, Mariza Gomes Faria, Aparecida D. Alves-dos-Santos, Isabel Amaral, Maria do Carmo Estanislau do Marsaioli, Anita Behenic Acid Fatty Acid Oil Angiosperm Biotransformation Chemical Cue Chemical Ecology Fatty Acid Flower Visiting Oil Pollination Animals Bee Flower Malpighiaceae Mass Spectrometry Metabolism Nuclear Magnetic Resonance Spectroscopy Orchidaceae Physiology Species Difference Chromatography, Thin Layer Animal Bees Chromatography, Thin Layer Fatty Acids Flowers Magnetic Resonance Spectroscopy Malpighiaceae Mass Spectrometry Oils Orchidaceae Species Specificity Anthophoridae Apidae Apoidea Byrsonima Intermedia Malpighiaceae Oncidiinae Orchidaceae Tetrapedia Diversipes 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. © 2007 Springer Science+Business Media, LLC. 2020-06-15T22:02:25Z 2020-06-15T22:02:25Z 2007 Artigo https://repositorio.inpa.gov.br/handle/1/18648 10.1007/s10886-007-9309-y en Volume 33, Número 7, Pags. 1421-1429 Restrito Journal of Chemical Ecology |
| institution |
Instituto Nacional de Pesquisas da Amazônia - Repositório Institucional |
| collection |
INPA-RI |
| language |
English |
| topic |
Behenic Acid Fatty Acid Oil Angiosperm Biotransformation Chemical Cue Chemical Ecology Fatty Acid Flower Visiting Oil Pollination Animals Bee Flower Malpighiaceae Mass Spectrometry Metabolism Nuclear Magnetic Resonance Spectroscopy Orchidaceae Physiology Species Difference Chromatography, Thin Layer Animal Bees Chromatography, Thin Layer Fatty Acids Flowers Magnetic Resonance Spectroscopy Malpighiaceae Mass Spectrometry Oils Orchidaceae Species Specificity Anthophoridae Apidae Apoidea Byrsonima Intermedia Malpighiaceae Oncidiinae Orchidaceae Tetrapedia Diversipes |
| spellingShingle |
Behenic Acid Fatty Acid Oil Angiosperm Biotransformation Chemical Cue Chemical Ecology Fatty Acid Flower Visiting Oil Pollination Animals Bee Flower Malpighiaceae Mass Spectrometry Metabolism Nuclear Magnetic Resonance Spectroscopy Orchidaceae Physiology Species Difference Chromatography, Thin Layer Animal Bees Chromatography, Thin Layer Fatty Acids Flowers Magnetic Resonance Spectroscopy Malpighiaceae Mass Spectrometry Oils Orchidaceae Species Specificity Anthophoridae Apidae Apoidea Byrsonima Intermedia Malpighiaceae Oncidiinae Orchidaceae Tetrapedia Diversipes Reis, Mariza Gomes Byrsonic acid - The clue to floral mimicry involving oil-producing flowers and oil-collecting bees |
| topic_facet |
Behenic Acid Fatty Acid Oil Angiosperm Biotransformation Chemical Cue Chemical Ecology Fatty Acid Flower Visiting Oil Pollination Animals Bee Flower Malpighiaceae Mass Spectrometry Metabolism Nuclear Magnetic Resonance Spectroscopy Orchidaceae Physiology Species Difference Chromatography, Thin Layer Animal Bees Chromatography, Thin Layer Fatty Acids Flowers Magnetic Resonance Spectroscopy Malpighiaceae Mass Spectrometry Oils Orchidaceae Species Specificity Anthophoridae Apidae Apoidea Byrsonima Intermedia Malpighiaceae Oncidiinae Orchidaceae Tetrapedia Diversipes |
| description |
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. © 2007 Springer Science+Business Media, LLC. |
| format |
Artigo |
| author |
Reis, Mariza Gomes |
| author2 |
Faria, Aparecida D. Alves-dos-Santos, Isabel Amaral, Maria do Carmo Estanislau do Marsaioli, Anita |
| author2Str |
Faria, Aparecida D. Alves-dos-Santos, Isabel Amaral, Maria do Carmo Estanislau do Marsaioli, Anita |
| title |
Byrsonic acid - The clue to floral mimicry involving oil-producing flowers and oil-collecting bees |
| title_short |
Byrsonic acid - The clue to floral mimicry involving oil-producing flowers and oil-collecting bees |
| title_full |
Byrsonic acid - The clue to floral mimicry involving oil-producing flowers and oil-collecting bees |
| title_fullStr |
Byrsonic acid - The clue to floral mimicry involving oil-producing flowers and oil-collecting bees |
| title_full_unstemmed |
Byrsonic acid - The clue to floral mimicry involving oil-producing flowers and oil-collecting bees |
| title_sort |
byrsonic acid - the clue to floral mimicry involving oil-producing flowers and oil-collecting bees |
| publisher |
Journal of Chemical Ecology |
| publishDate |
2020 |
| url |
https://repositorio.inpa.gov.br/handle/1/18648 |
| _version_ |
1787142771887308800 |
| score |
11.755432 |