Oncidinol—a novel diacylglycerol from Ornithophora radicans Barb. Rodr. (Orchidaceae) floral oil

Reis, Mariza Gomes; Faria, Aparecida Donisete De; Amaral, Maria do Carmo Estanislau do; Marsaioli, Anita Jocelyne

doi:10.1016/j.tetlet.2003.09.015

Cited by 27 publications

(24 citation statements)

References 10 publications

(1 reference statement)

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“…Some of these compounds were also reported from Oncidium oil (Reis et al, 2000). EI mass spectra of 1-acyl-2,3-diacetyl-glycerols were also previously described (Reis et al, 2003).…”

Section: Ei-ms Analysis Of the Acylglycerols Of Diascia Oilsmentioning

confidence: 99%

“…doi:10.1016/j.phytochem.2007.12.012 b-acetoxy fatty acids were found as main lipid components (Vogel, 1969(Vogel, , 1974(Vogel, , 1986(Vogel, , 1990Simpson et al, 1977Simpson et al, , 1979Seigler et al, 1978;Cane et al, 1983;Simpson and Neff, 1983;Buchmann, 1987;Vinson et al, 1997). The structure of a novel diacylglycerol of Ornithophora radicans was elucidated from spectroscopic data (Reis et al, 2000(Reis et al, , 2003. Our group was first to report partially acetylated 3,7-dihydroxy fatty acids as a new type of constituent in Malpighia coccigera (Malpighiaceae) oil; and to discuss a possible relationship between floral oil and plant epicuticular wax biosynthesis.…”

Section: Introductionmentioning

confidence: 99%

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Non-volatile floral oils of Diascia spp. (Scrophulariaceae)

et al. 2008

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“…Some of these compounds were also reported from Oncidium oil (Reis et al, 2000). EI mass spectra of 1-acyl-2,3-diacetyl-glycerols were also previously described (Reis et al, 2003).…”

Section: Ei-ms Analysis Of the Acylglycerols Of Diascia Oilsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Non-volatile floral oils of Diascia spp. (Scrophulariaceae)

et al. 2008

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“…Putative precursors, 3-hydroxy-and 3,n-dihydroxy-substituted fatty acids could be detected in neither the glandular trichome exudate nor the leaf extract of P. tomentosa. Recently, closely related glycerides have been characterized in the floral oils of Orchidaceae and Scrophulariaceae plants [12] [19] [21]. In addition, 3-(acetyloxy)-, 5-(acetyloxy)-, 7-(acetyloxy)-3-hydroxy-, 9-(acetyloxy)-3-hydroxy-, and 9-(acetyloxy)-5-hydroxy-substituted fatty acids were characterized as constituents of these plants floral oils [13] [22].…”

Section: -O-[(3r6s)-3-(acetyloxy)-6-hydroxyoctadecanoyl]glycerol) (1mentioning

confidence: 99%

“…We acknowledge Prof. Anita J. Marsaioli, University of Campinas, Brazil, through whom we became aware that the structures of 1-O-acetyl-2-O-[(3R,6R)-3,6-bis(acetyloxy)eicosanoyl]-sn-glycerol and its docosanoyl homologue reported in [21] had been revised to the corresponding 3,7-bis(acetyloxy) compounds [20].…”

Section: -O-[(3r6s)-3-(acetyloxy)-6-hydroxyoctadecanoyl]glycerol) (1mentioning

confidence: 99%

Acylglycerols (=Glycerides) from the Glandular Trichome Exudate on the Leaves of Paulownia tomentosa

Asai

Hara

Kobayashi

et al. 2009

Helvetica Chimica Acta

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Chemical investigations of the glandular trichome exudates on the leaves of Paulownia tomentosa (Scrophulariaceae) led to the identification of the thirty acylglycerols (=glycerides) 1–30, including five known ones (2, 3, 6, 9, and 15) (Fig. 1). Spectroscopic analysis combined with GC/MS studies of the glycerides and the liberated fatty acids, in the form of trimethylsilyl ether derivatives and trimethylsilylated methyl esters, respectively, established that the constituents belonged to 1,3‐di‐O‐acetyl‐2‐O‐(fatty acyl)glycerols, 1‐O‐acetyl‐2‐O‐(fatty acyl)‐sn‐glycerols, and 2‐O‐(fatty acyl)glycerols, wherein the fatty acyl moiety was either an eicosanoyl or an octadecanoyl group bearing OH and/or AcO groups at the 3‐, 3,6‐, 3,7‐, 3,8‐, or 3,9‐positions. The 1‐O‐acetyl‐2‐O‐[(3R,6S)‐3‐(acetyloxy)‐6‐hydroxyeicosanoyl]‐sn‐glycerol (12; 20% of the total glycerides), 2‐O‐[(3R,8R)‐3,8‐bis(acetyloxy)eicosanoyl]glycerol (17; 14%), 2‐O‐[(3R,9R)‐3,9‐bis(acetyloxy)eicosanoyl]glycerol (18; 12%), and 2‐O‐[(3R)‐3‐(acetyloxy)eicosanoyl]glycerol (10; 12%) were relatively abundant constituents. The configurations of the stereogenic centers of the fatty acyl moieties were determined by 1H‐NMR analysis of the monoesters obtained from (R)‐ and (S)‐2‐(naphthalen‐2‐yl)‐2‐methoxyacetic acid ((R)‐ and (S)‐2NMAOH and the hydroxy‐substituted fatty acid methyl esters (Fig. 2). The configuration at C(2) of the glycerol moiety of the 1‐O‐acetyl‐2‐O‐(fatty acyl)glycerols was determined to be (2S) by chemical conversion of, e.g., G‐2 (=2/3 1 : 10) to (+)‐3‐O‐[tert‐butyl)diphenylsilyl]‐sn glycerol of known absolute configuration.

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“…Orchids use efficient attraction strategies allowing the survival of species by either offering rewards (diacylglycerol in Oncidiinae 1 ) or not rarely, deceiving the pollinators when the flowers are rewardless. 1,2 Many orchids are "food-frauds", that is, they show flower features (flower shape, fragrances, etc.) that provoke the attraction of food-seeking pollinators 2,4 .…”

Section: Introductionmentioning

confidence: 99%