Tigliane diterpenes from Croton mauritianus as inhibitors of chikungunya virus replication

Fitoterapia. 2014 Sep:97:87-91. doi: 10.1016/j.fitote.2014.05.015. Epub 2014 May 28.

Abstract

A bioassay-guided purification of an EtOAc extract of the leaves of Croton mauritianus using a chikungunya virus-cell-based assay led to the isolation of 12-O-decanoylphorbol-13-acetate (1) and the new 12-O-decanoyl-7-hydroperoxy-phorbol-5-ene-13-acetate (2), along with loliolide, vomifoliol, dehydrovomifoliol, annuionone D and bluemol C. The planar structure and the relative configuration of compound 2 were elucidated based on spectroscopic analysis, including 1D- and 2D-NMR experiments, mass spectrometry, and comparison with literature data. Compounds 1 and 2 inhibited chikungunya virus-induced cell death in cell culture with EC50s of 2.4±0.3 and 4.0±0.8 μM, respectively.

Keywords: Chikungunya; Croton mauritianus; Euphorbiaceae; HIV; Phorbol esters; Tigliane.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemistry
  • Antiviral Agents / isolation & purification*
  • Antiviral Agents / pharmacology
  • Benzofurans / isolation & purification
  • Benzofurans / pharmacology
  • Butanols / isolation & purification
  • Butanols / pharmacology
  • Chikungunya virus / drug effects*
  • Croton / chemistry*
  • Cyclohexanones / isolation & purification
  • Cyclohexanones / pharmacology
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology
  • Microbial Sensitivity Tests
  • Norisoprenoids / isolation & purification*
  • Norisoprenoids / pharmacology
  • Phorbol Esters / isolation & purification*
  • Phorbol Esters / pharmacology
  • Plant Leaves / chemistry
  • Virus Replication / drug effects

Substances

  • Antiviral Agents
  • Benzofurans
  • Butanols
  • Cyclohexanones
  • Diterpenes
  • Norisoprenoids
  • Phorbol Esters
  • dehydrovomifoliol
  • vomifoliol
  • loliolide