Journal
PHYTOCHEMISTRY
Volume 72, Issue 4-5, Pages 409-414Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2011.01.021
Keywords
Chromolaena pulchella; Asteraceae; ent-Clerodanes; Labdanes; Absolute configuration; Vibrational circular dichroism
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Funding
- CONACYT, Mexico [U2-80555, 11828]
- CIC-UMSNH
- CONACYT [206545, 171415]
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The aerial parts of Chromolaena pulchella biosynthesize two groups of ditierpenes belonging to opposite enantiomeric series, specifically, the furanoid ent-clerodanes (5R,8R,9S,10R)-(-)-hardwikiic acid (1), methyl (5R,8R,9S,10R)-(-)-hardwikiate (2), (55,8R,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 labdaries with their theoretical spectra obtained by density functional theory calculations. The results support a biogenetic proposal to diterpenes found in the studied botanical species. (C) 2011 Elsevier Ltd. All rights reserved.
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