Leishmanicidal activities and cytotoxicities of bisnaphthoquinone analogues and naphthol derivatives from Burman Diospyros burmanica

Bioorg Med Chem. 2012 Sep 1;20(17):5215-9. doi: 10.1016/j.bmc.2012.06.055. Epub 2012 Jul 13.

Abstract

A methanol extract of the wood of Diospyros burmanica, collected in Burma (Myanmar), was found to exhibit significant activity against Leishmania major. Subsequent chromatographically resolved fractionation led to the isolation of three novel bisnaphthoquinone analogues, burmanin A, B, and C (1-3), together with nine known compounds (4-12). The structure of 1 was confirmed by X-ray crystallography, and those of 2 and 3 by spectroscopic techniques, including 1D and 2D NMR. The inhibitory activities of the isolates were evaluated against the promastigote forms of Leishmania major and the murine macrophage-like cell line, RAW264.7.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / isolation & purification
  • Antiprotozoal Agents / pharmacology*
  • Cell Survival / drug effects
  • Cells, Cultured
  • Crystallography, X-Ray
  • Diospyros / chemistry*
  • Dose-Response Relationship, Drug
  • Leishmania major / drug effects*
  • Leishmania major / metabolism
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Myanmar
  • Naphthols / chemistry
  • Naphthols / isolation & purification
  • Naphthols / pharmacology*
  • Naphthoquinones / chemistry
  • Naphthoquinones / isolation & purification
  • Naphthoquinones / pharmacology*
  • Parasitic Sensitivity Tests
  • Plant Extracts / chemistry
  • Stereoisomerism
  • Structure-Activity Relationship
  • Wood / chemistry

Substances

  • Antiprotozoal Agents
  • Naphthols
  • Naphthoquinones
  • Plant Extracts