Molecular structures and antiviral activities of naturally occurring and modified cassane furanoditerpenoids and friedelane triterpenoids from Caesalpinia minax

Bioorg Med Chem. 2002 Jul;10(7):2161-70. doi: 10.1016/s0968-0896(02)00072-x.

Abstract

Further investigation of the active components of the chloroform fraction of the seeds of Caesalpinia minax led to the isolation of a new cassane furanoditerpenoid, caesalmin H (1), together with two known furanoditerpenoid lactones, caesalmin B (2) and bonducellpin D (3). Reduction of the naturally abundant caesalmin D (9), E (10) and F (11) resulted in three new furanoditerpenoid derivatives 4-6. Phytochemical study of the stem of the same plant and subsequent reduction afforded two friedelane triterpenoids (7-8), which were identified by spectroscopic methods. Compounds 1-2 and 4-8 were corroborated by single crystal X-ray analysis. The factors governing the reduction of cassane furanoditerpenoids and friedelane triterpenoids were investigated by correlating the crystallographic results with density functional theory. The inhibitory activities of 2-8 on the Para3 virus were evaluated by cytopathogenic effects (CPE) reduction assay.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology*
  • Cell Line
  • Diterpenes / chemical synthesis*
  • Diterpenes / pharmacology*
  • Fabaceae / chemistry*
  • Humans
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Triterpenes / chemical synthesis*
  • Triterpenes / pharmacology*

Substances

  • Antiviral Agents
  • Diterpenes
  • Triterpenes