Novel diterpenoids and diterpenoid glycosides from Siegesbeckia orientalis

J Nat Prod. 2004 Sep;67(9):1517-21. doi: 10.1021/np0400407.

Abstract

Eight new ent-pimarane diterpenoids and diterpenoid glycosides, namely, ent-12alpha,16-epoxy-2beta,15alpha,19-trihydroxypimar-8-ene (1), ent-12alpha,16-epoxy-2beta,15alpha,19-trihydroxypimar-8(14)-ene (2), ent-2alpha,15,16,19-tetrahydroxypimar-8(14)-ene, ent-15-oxo-2beta,16,19-trihydroxypimar-8(14)-ene, ent-2-oxo-15,16-dihydroxypimar-8(14)-en-16-O-beta-glucopyranoside, ent-2-oxo-15,16,19-trihydroxypimar-8(14)-ene, ent-2-oxo-3beta,15,16-trihydroxypimar-8(14)-en-3-O-beta-glucopyranoside, and ent-2beta,15,16,19-tetrahydroxypimar-8(14)-en-19-O-beta-glucopyranoside, together with seven known diterpenes were isolated from Siegesbeckia orientalis. Compounds 1 and 2 are novel ent-pimarane diterpenoids with an unprecedented 12alpha,16-epoxy group. Their structures were established by spectral methods, especially 1D and 2D NMR spectral methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abietanes / chemistry
  • Abietanes / isolation & purification*
  • Asteraceae / chemistry*
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Medicine, Chinese Traditional
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*
  • Stereoisomerism

Substances

  • Abietanes
  • Glycosides
  • pimarane