Neo-clerodane diterpenes from Teucrium fruticans

Phytochemistry. 2004 Feb;65(4):387-92. doi: 10.1016/j.phytochem.2003.09.018.

Abstract

In addition to three out of the four previously reported neo-clerodanes already found in Teucrium fruticans (fruticolone, isofruticolone and 8 beta-hydroxyfruticolone), and 6-acetylteucjaponin B (isolated from T. scordium and T. grisebachii), four new neo-clerodanes, namely 7 beta-hydroxyfruticolone, 11-hydroxyfruticolone, deacetylfruticolone and 6-acetyl-10-hydroxyteucjaponin B were also isolated. The structures were unambiguously elucidated based on extensive NMR spectral studies (one- and two-dimensional experiments). Semi-prep-HPLC proved to be a convenient purification procedure, occasionally being followed by TLC. The new compounds were assayed against Spodoptera littoralis and two of them were shown to have potent antifeedant activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification*
  • Diterpenes, Clerodane / chemistry*
  • Diterpenes, Clerodane / isolation & purification*
  • Feeding Behavior / drug effects
  • Insecticides / chemistry
  • Insecticides / isolation & purification
  • Larva
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Spodoptera / physiology
  • Teucrium / chemistry*

Substances

  • Diterpenes
  • Diterpenes, Clerodane
  • Insecticides
  • neoclerodane