New bicyclo[3.1.0]hexane unit ent-kaurane diterpene and its seco-derivative from Isodon eriocalyx var. laxiflora

Org Lett. 2012 Jan 6;14(1):302-5. doi: 10.1021/ol203061z. Epub 2011 Dec 19.

Abstract

Neolaxiflorin A (1), an unprecedented ent-kaurane diterpenoid with a bicyclo[3.1.0]hexane unit, and its seco-derivative, neolaxiflorin B (2), along with two known compounds 3 and 4 were isolated from the leaves of Isodon eriocalyx var. laxiflora. The absolute configuration of 1 was determined by spectral methods and single crystal X-ray diffraction analysis. Compound 4 and the synthesized compound 5 exhibited significant cytotoxicity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged Bicyclo Compounds / chemistry*
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Cyclohexanes / chemistry*
  • Diterpenes, Kaurane / chemistry*
  • Diterpenes, Kaurane / pharmacology
  • Humans
  • Isodon / chemistry*
  • Models, Molecular
  • Molecular Conformation

Substances

  • Bridged Bicyclo Compounds
  • Cyclohexanes
  • Diterpenes, Kaurane