Prenylated benzophenones from Triadenum japonicum

J Nat Prod. 2015 Feb 27;78(2):258-64. doi: 10.1021/np500827h. Epub 2015 Jan 20.

Abstract

Six new prenylated benzophenones, (-)-nemorosonol (1) and trijapins A-E (2-6), were isolated from the aerial parts of Triadenum japonicum. (-)-Nemorosonol (1) and trijapins A-C (2-4) have a common tricyclo[4.3.1.0(3,7)]decane skeleton, while 1 is an enantiomer of (+)-nemorosonol previously isolated from Clusia nemorosa. The absolute configuration of (-)-nemorosonol (1) was assigned by ECD spectroscopy. Trijapins A-C (2-4) are analogues of 1 possessing an additional tetrahydrofuran ring. Trijapins D (5) and E (6) are prenylated benzophenones with a 1,2-dioxane moiety and a hydroperoxy group, respectively. (-)-Nemorosonol (1) exhibited antimicrobial activity against Escherichia coli (MIC, 8 μg/mL), Staphylococcus aureus (MIC, 16 μg/mL), Bacillus subtilis (MIC, 16 μg/mL), Micrococcus luteus (MIC, 32 μg/mL), Aspergillus niger (IC50, 16 μg/mL), Trichophyton mentagrophytes (IC50, 8 μg/mL), and Candida albicans (IC50, 32 μg/mL), while trijapin D (5) showed antimicrobial activity against C. albicans (IC50, 8 μg/mL).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Aspergillus niger / drug effects
  • Bacillus subtilis / drug effects
  • Benzophenones / chemistry
  • Benzophenones / isolation & purification*
  • Benzophenones / pharmacology
  • Candida albicans / drug effects
  • Escherichia coli / drug effects
  • Hypericum / chemistry*
  • Japan
  • Microbial Sensitivity Tests
  • Micrococcus luteus / drug effects
  • Molecular Structure
  • Plant Components, Aerial / chemistry
  • Prenylation
  • Staphylococcus aureus / drug effects
  • Stereoisomerism
  • Trichophyton / drug effects

Substances

  • Anti-Bacterial Agents
  • Benzophenones