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  • Title: Absolute configuration of labdanes and ent-clerodanes from Chromolaena pulchella by vibrational circular dichroism.
    Author: Gómez-Hurtado MA, Torres-Valencia JM, Manríquez-Torres J, del Río RE, Motilva V, García-Mauriño S, Avila J, Talero E, Cerda-García-Rojas CM, Joseph-Nathan P.
    Journal: Phytochemistry; 2011 Apr; 72(4-5):409-14. PubMed ID: 21315393.
    Abstract:
    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.
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