Tetranorclerodanes and clerodane-type diterpene glycosides from Dicranopteris dichotoma

J Nat Prod. 2007 Feb;70(2):265-8. doi: 10.1021/np0603166.

Abstract

The acetone extract of Dicranopteris dichotoma afforded two new tetranorclerodanes, 18-hydroxyaylthonic acid (1) and 18-oxo-aylthonic acid (2), and four new clerodane-type diterpene glycosides, (6S,13S)-6-O-[6-O-acetyl-beta-d-glucopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl]cleroda-3,14-dien-13-ol (3), (6S,13S)-6-O-[4-O-acetyl-beta-d-glucopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl]cleroda-3,14-dien-13-ol (4), 6-O-[6-O-acetyl-beta-d-glucopyranos-yl-(1-->4)-alpha-l-rhamnopyranosyl]-(13E)-cleroda-3,13-dien-15-ol (5), and 6-O-[beta-d-glucopyranosyl]-(1-->4)-alpha-l-rhamnopyranosyl-(13E)-cleroda-3,13-dien-15-ol (6), together with two known compounds, aylthonic acid (7) and (6S,13S)-cleroda-3,14-diene-6,13-diol (8). The structures of these new compounds were established by a combination of 1D and 2D NMR techniques, MS, and acid hydrolysis. Compound 8 showed modest anti-HIV-1 activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / classification
  • Anti-HIV Agents / isolation & purification*
  • Anti-HIV Agents / pharmacology
  • China
  • Diterpenes, Clerodane / chemistry
  • Diterpenes, Clerodane / classification
  • Diterpenes, Clerodane / isolation & purification*
  • Diterpenes, Clerodane / pharmacology
  • Ferns / chemistry*
  • Glycosides / chemistry
  • Glycosides / classification
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • HIV-1 / drug effects
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular

Substances

  • Anti-HIV Agents
  • Diterpenes, Clerodane
  • Glycosides