Anti-staphylococcal acylphloroglucinols from Hypericum beanii

Phytochemistry. 2006 Dec;67(23):2568-72. doi: 10.1016/j.phytochem.2006.09.037. Epub 2006 Nov 7.

Abstract

As part of an ongoing project to investigate the anti-staphylococcal properties of the Hypericum genus, an acylphloroglucinol, 1,5-dihydroxy-2-(2'-methylpropionyl)-3-methoxy-6-methylbenzene (1), was isolated from the dichloromethane extract of the aerial parts of H. beanii (Guttiferae), together with a minor related acylphloroglucinol 1,5-dihydroxy-2-(2'-methylbutanoyl)-3-methoxy-6-methylbenzene (2) as a mixture in a 5:2 ratio. The known compounds 1,7-dihydroxyxanthone (3), stigmasterol, catechin and shikimic acid were also isolated from this plant. The structures of the compounds were characterized by extensive 1- and 2D NMR spectroscopy and mass spectrometry. The minimum inhibitory concentration (MIC) values the acylphloroglucinol mixture and (3) against a panel of multidrug-resistant strains of Staphylococcus aureus ranged from 16-32 microg/ml to 128-256 microg/ml, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / metabolism
  • Anti-Bacterial Agents / pharmacology*
  • Hypericum / metabolism*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Phloroglucinol / analogs & derivatives*
  • Phloroglucinol / chemistry*
  • Phloroglucinol / metabolism
  • Phloroglucinol / pharmacology
  • Staphylococcus aureus / drug effects*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Phloroglucinol