Two new diterpenes from the seeds of Caesalpinia minax Hance

J Asian Nat Prod Res. 2015;17(9):893-9. doi: 10.1080/10286020.2015.1039998. Epub 2015 Aug 14.

Abstract

Molecules with diterpene skeletons often possess valuable medicinal properties. Two new diterpenes 1α,6α,7β-triacetoxy-5α-hydroxy-14β-ethyl-O-vouacapane (1) and 2α-acetoxy-14,15-cyclopimara-7β,16-diol (2) were isolated from the seeds of Caesalpinia minax Hance. Their structures were established on the basis of extensive spectroscopic analyses, including HR-ESI-MS, UV, IR, 1D, and 2D NMR (HSQC, HMBC, NOESY) methods. The stereochemical structure of 1 was confirmed via the circular dichroism spectrum and calculated ECD experiment. The inhibitory activity of nitric oxide production of RAW264.7 macrophages stimulated by lipopolysaccharide of compounds 1 and 2 was evaluated, and compound 1 was found to show significant inhibitory effect.

Keywords: Caesalpinia minax; anti-inflammation; circular dichroism; diterpenes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology
  • Caesalpinia / chemistry*
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Lipopolysaccharides / pharmacology
  • Mice
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Seeds / chemistry

Substances

  • 1alpha,6alpha,7beta-triacetoxy-5alpha-hydroxy-14beta-ethyl-O-vouacapane
  • 2alpha-acetoxy-14,15-cyclopimara-7beta,16-diol
  • Anti-Inflammatory Agents
  • Diterpenes
  • Drugs, Chinese Herbal
  • Lipopolysaccharides
  • Nitric Oxide