Chemical Constituents from Flueggea virosa and the Structural Revision of Dehydrochebulic Acid Trimethyl Ester

Molecules. 2016 Sep 16;21(9):1239. doi: 10.3390/molecules21091239.

Abstract

In an attempt to study the chemical constituents from the twigs and leaves of Flueggea virosa, a new terpenoid, 9(10→20)-abeo-ent-podocarpane, 3β,10α-dihydroxy-12-methoxy-13- methyl-9(10→20)-abeo-ent-podocarpa-6,8,11,13-tetraene (1), as well as five known compounds were characterized. Their structures were elucidated on the basis of spectroscopic analysis. In addition, the structure of dehydrochebulic acid trimethyl ester was revised as (2S,3R)-4E-dehydrochebulic acid trimethyl ester based on a single-crystal X-ray diffraction study. The in vitro anti-hepatitis C virus (anti-HCV) activity and cytotoxicity against Huh7.5 cells for the isolated compounds were evaluated.

Keywords: Flueggea virosa; HCVcc; anti-HCV; dehydrochebulic acid trimethyl ester; ent-podocarpane.

MeSH terms

  • Antiviral Agents* / chemistry
  • Antiviral Agents* / isolation & purification
  • Antiviral Agents* / pharmacology
  • Benzopyrans* / chemistry
  • Benzopyrans* / isolation & purification
  • Benzopyrans* / pharmacology
  • Cell Line
  • Euphorbiaceae / chemistry*
  • Hepacivirus*
  • Hepatitis C / drug therapy*
  • Hepatitis C / metabolism
  • Humans
  • Maleates* / chemistry
  • Maleates* / isolation & purification
  • Maleates* / pharmacology
  • Plant Roots / chemistry*

Substances

  • Antiviral Agents
  • Benzopyrans
  • Maleates
  • dehydrochebulic acid trimethyl ester