Anti-hepatitis B virus lignans from the root of Streblus asper

Bioorg Med Chem Lett. 2013 Apr 1;23(7):2238-44. doi: 10.1016/j.bmcl.2013.01.046. Epub 2013 Jan 24.

Abstract

Four new lignans, strebluslignanol F (1), (7'R,8'S,7″R,8″S)-erythro-strebluslignanol G (2), isomagnaldehyde (3) and isostrebluslignanaldehyde (4), along with 12 known lignans (5-16) were isolated from the ethyl acetate-soluble part of MeOH extract of the root of Streblus asper. Their structures were elucidated through various spectroscopic methods, including 1D NMR ((1)H NMR, (13)C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centers was determined using CD spectra, as well as analyses of coupling constants and optical rotation data. The isolated lignans were evaluated for their anti-HBV activities in vitro using the HBV transfected HepG2.2.15 cell line. The most active lignans, (7'R,8'S,7″R,8″S)-erythro-strebluslignanol G, magnolol, isomagnolol and isolariciresinol, exhibited significant anti-HBV activities with IC50 values of 1.58, 2.03, 10.34 and 3.67 μM, respectively, for HBsAg with no cytotoxicity, and of 3.24, 3.76, 8.83 and 14.67 μM, respectively, for HBeAg with no cytotoxicity. (7'R,8'S,7″R,8″S)-erythro-Strebluslignanol G and magnolol showed significant anti-HBV activities to inhibit the replication of HBV DNA with the IC50 values of 9.02 and 8.67 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemistry
  • Antiviral Agents / isolation & purification
  • Antiviral Agents / pharmacology*
  • Dose-Response Relationship, Drug
  • Hep G2 Cells
  • Hepatitis B virus / drug effects*
  • Humans
  • Lignans / chemistry
  • Lignans / isolation & purification
  • Lignans / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Moraceae / chemistry*
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology*
  • Plant Roots / chemistry*
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • Lignans
  • Plant Extracts