New cyclopentenyl fatty acids in Flacourtiaceae. Straight-chain fatty acids and cycloic fatty acids in lipids during maturation of the seeds

Spener, Friedrich; Mangold, Helmut K.

doi:10.1021/bi00708a001

Cited by 34 publications

(21 citation statements)

References 28 publications

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“…Os dois primeiros já haviam sido descritos nesta espécie por Cole e Cardoso 31 e os outros foram encontrados no óleo e no extrato das folhas das espécies C. echinata e H. anthelmintica (Flacourtiaceae). 32 O íon de m/z 74, oriundo do rearranjo de McLafferty e característico de ésteres metílicos de ácidos graxos, é formado com baixa abundância relativa nos ésteres ciclopentênicos.…”

Section: Resultados E Discussão Determinação Do Teor Dos áCidos Graxounclassified

Ácidos ciclopentênicos do óleo da sapucainha (Carpotroche brasiliensis Endl, Flacourtiaceae): o primeiro antileprótico usado no Brasil

et al. 2009

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Ácidos ciclopentênicos do óleo da sapucainha (Carpotroche brasiliensisendlRecebido em 5/3/08; aceito em 1/8/08; publicado na web em 20/1/09 CYCLOPENTENYL ACIDS FROM SAPUCAINHA OIL (Carpotroche brasiliensis Endl, Flacourtiaceae): THE FIRST ANTILEPROTIC USED IN BRAZIL. The chaoolmugra oil is one of the oldest medicines used for leprosy until the development of sulfas. In Brazil, it is known as sapucainha oil that is obtained from Carpotroche brasilienesis seeds (Flacourtiaceae). Chemical and medicinal studies of sapucainha oil were introduced in Brazil by Peckolt, Cole and Cardoso which showed that major ciclopentenyl fatty acids as chaulmoogric, hydnocarpic and gorlic were responsible for its bactericidal activity. In this work, a method for quantification of sapucainha oil acidic fraction by HRGC was established using methyl n-heptadecanoate as internal standard. The oil chemical stability was investigated by the use of GC-MS, IR, 1 H and 13 C NMR and showed that the main degradation products belong to the cyclopentenyl moiety oxidation.

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Section: Resultados E Discussão Determinação Do Teor Dos áCidos Graxounclassified

Ácidos ciclopentênicos do óleo da sapucainha (Carpotroche brasiliensis Endl, Flacourtiaceae): o primeiro antileprótico usado no Brasil

et al. 2009

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“…The fatty acid profile of the latter was almost identical to that of the whole seed [2]. Previous results indicated that Cls-cyclopentenyl fatty acids were synthesized by elongation of hydnocarpic acid mediated by special 'elongases' [7].…”

Section: Biosynthesis Of Cyclopentenyl Fatty Acids In Endosperm and Ementioning

confidence: 60%

Biosynthesis of Cyclopentenyl Fatty Acids

Cramer

Spener

1977

European Journal of Biochemistry

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In seeds of Hydnocarpus anthelminthica of Flacourtiaceae, cyclopentenylglycine and cyclopentenyl fatty acids are found naturally. The non‐proteinogenic amino acid may serve as precursor of cyclo‐pentenyl fatty acids via aleprolic acid, the starter molecule for these long‐chain compounds. After administration of cyclopentenyl[2‐14C]glycine to maturing seeds of H. anthelminthica, labelled cyclopentenyl fatty acids were synthesized. Comparative activities were observed, when [1‐14C]aleprolic acid was supplied to the seeds. Incorporation studies with [1‐14C]acetate revealed that the chain‐lengthening systems for straight‐chain and cyclic fatty acids were still functioning in mature seeds. Endosperm and embryo of H. anthelminthica seeds synthesized cyclopentenyl fatty acids from cyclopentenyl[2‐14C]glycine, [1‐14C]aleprolic acid and [1‐14C]acetate. In embryonic tissue, a dilution experiment proved the following path for cyclopentenyl fatty acid biosynthesis: cyclopentenylglycine → aleprolic acid → cyclopentenyl fatty acids. The conversion of cyclopentenylglycine to aleprolic acid may occur via transamination and oxidative decarboxylation; activated aleprolic acid is then lengthened by C2‐units to cyclopentenyl fatty acids.

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“…It is most practical to separate the methyl esters of saturated and monounsaturated straight-chain fatty acids from all the others by chromatography on silica gel containing silver nitrate, and then to analyze each of the two groups of methyl esters by gas chromatography on a relatively polar stationary phase [53]. The consecutive application of argentation chromatography and gas chromatography [61] if of great value when small amounts of the methyl esters of individual cyclopentenyl fatty acids are to be isolated in order to determine their structures [53] or their radioactivities [54].…”

Section: Methods Of Analysismentioning

confidence: 99%