Sorocenols G and H, anti-MRSA oxygen heterocyclic Diels-Alder-type adducts from Sorocea muriculata roots

J Nat Prod. 2008 Oct;71(10):1764-7. doi: 10.1021/np800446g. Epub 2008 Oct 11.

Abstract

Bioassay-guided fractionation of a root extract of Sorocea muriculata led to the isolation and identification of two new oxygen heterocyclic Diels-Alder-type adducts, sorocenols G (1) and H (2), along with lupeol-3-(3' R-hydroxytetradecanoate) and oxyresveratrol. The structures of 1 and 2 were elucidated using 1D and 2D NMR spectroscopic and HRMS data and by comparison with reported values. The absolute configurations of 1 and 2 were established by analysis of their experimental and theoretically calculated CD spectra. Compounds 1 and 2 showed significant and selective activity against methicillin-resistant Staphylococcus aureus with IC50 values of 1.5 and 0.5 microM, respectively. Compound 2 also displayed antifungal activity against Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus, with IC 50 values of 5.4, 5.4, and 10.0 microM, respectively.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / isolation & purification
  • Anti-Bacterial Agents* / pharmacology
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology
  • Aspergillus fumigatus / drug effects
  • Benzofurans / chemistry*
  • Benzofurans / isolation & purification*
  • Candida albicans / drug effects
  • Cryptococcus neoformans / drug effects
  • Inhibitory Concentration 50
  • Methicillin Resistance / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Moraceae / chemistry*
  • Oxygen / chemistry
  • Peru
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Roots / chemistry
  • Staphylococcus aureus / drug effects*
  • Stilbenes / chemistry
  • Stilbenes / isolation & purification

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Benzofurans
  • Plant Extracts
  • Stilbenes
  • sorocenol G
  • sorocenol H
  • puag-haad
  • Oxygen