ent-Pimarane diterpenoids from Siegesbeckia orientalis and structure revision of a related compound

J Nat Prod. 2009 Nov;72(11):2005-8. doi: 10.1021/np900449r.

Abstract

Six new ent-pimarane diterpenoids, namely, ent-14beta,16-epoxy-8-pimarene-3beta,15alpha-diol (1), 7beta-hydroxydarutigenol (2), 9beta-hydroxydarutigenol (3), 16-O-acetyldarutigenol (4), 15,16-di-O-acetyldarutoside (5), and 16-O-acetyldarutoside (6), were isolated from the ethanol extract of Siegesbeckia orientalis. Their structures were elucidated on the basis of spectroscopic studies, and the absolute configuration of 1 was established by the modified Mosher's method. Furthermore, the structure of ent-12beta,16-epoxy-8-pimarene-2alpha,15beta,19-triol, recently isolated from the same plant, should be revised as ent-14beta,16-epoxy-8-pimarene-2alpha,15alpha,19-triol (10).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abietanes / chemistry*
  • Abietanes / isolation & purification*
  • Asteraceae / chemistry*
  • Drugs, Chinese Herbal / chemistry*
  • Drugs, Chinese Herbal / isolation & purification*
  • Humans
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular

Substances

  • Abietanes
  • Drugs, Chinese Herbal
  • pimarane