Absolute configuration of labdanes and ent-clerodanes from Chromolaena pulchella by vibrational circular dichroism

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• 作者：Mario A. Gó ; mez-Hurtado^a ; J. Martí ; n Torres-Valencia^a ; ^{jmartin@uaeh.edu.mx} ; Jes&#xfa ; s Manrí ; quez-Torres^a ; Rosa E. del Rí ; o^b ; Virginia Motilva^c ; Sofí ; a Garcí ; a-Mauriñ ; o^d ; Javier Á ; vila^c ; Elena Talero^c ; Carlos M. Cerda-Garcí ; a-Rojas^e ; ^{ccerda@cinvestav.mx} ; Pedro Joseph-Nathan^e
• 关键词：Chromolaena pulchella ; Asteraceae ; ent-Clerodanes ; Labdanes ; Absolute configuration ; Vibrational circular dichroism
• 刊名：Phytochemistry
• 出版年：2011
• 出版时间：April 2011
• 年：2011
• 卷：72
• 期：4-5
• 页码：409-414
• 全文大小：586 K

文摘

The aerial parts of Chromolaena pulchella biosynthesize two groups of diterpenes belonging to opposite enantiomeric series, specifically, the furanoid ent-clerodanes (5R,8R,9S,10R)-(−)-hardwikiic acid (1), methyl (5R,8R,9S,10R)-(−)-hardwikiate (2), (5S,8R,9S,10R)-(−)-hautriwaic acid lactone (3), methyl (5R,8R,9S,10R)-(−)-nidoresedate (4) and methyl (8R,9R)-(−)-strictate (5), as well as the labdanes (5S,8R,9R,10S)-(+)-(13E)-labd-13-ene-8,15-diol (6) and (5S,8R,9R,10S)-(+)-isoabienol (7). The absolute configuration of the two groups of diterpenes was unambiguously assigned by comparison of the vibrational circular dichroism spectra of 3 for ent-clerodanes, and of 7 for labdanes with their theoretical spectra obtained by density functional theory calculations. The results support a biogenetic proposal to diterpenes found in the studied botanical species.