Antibacterial diterpenes from Calceolaria pinifolia

J Nat Prod. 2003 Feb;66(2):242-6. doi: 10.1021/np020380x.

Abstract

Two new isopimaranes, 19-methylmalonyloxy-ent-isopimara-8(9),15-diene (5) and 19-malonyloxy-ent-isopimara-8(9),15-diene (6), were isolated using bioassay-guided fractionation of the CH(2)Cl(2)-MeOH (1:1) extract of the aerial part of Calceolaria pinifolia along with eight other diterpenes (1-4, 7-10) and two triterpenes (11, 12). All compounds were assayed against Staphylococcus aureus (SA), methicillin-resistant S. aureus (MRSA), Bacillus subtilis (BS), and Escherichia coli (EC). 4-Epi-dehydroabietinol (2) and ent-isopimara-9(11),15-diene-19-ol (8) were found to be active against MRSA with MIC values of 8 and 2 microgram/mL, respectively. Mechanistic studies of 8 in BS suggested rapid and nonspecific inhibition of uptake and incorporation of radiolabeled precursors into DNA, RNA, and protein consistent with membrane-damaging effects in bacteria. Compound 8 did not afford protection against an acute infection with SA in mice.

Publication types

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

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Argentina
  • Bacillus subtilis / drug effects
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Erythrocytes / drug effects
  • Escherichia coli / drug effects
  • Female
  • Humans
  • Methicillin Resistance
  • Mice
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Molecular Structure
  • Plants, Medicinal / chemistry*
  • Scrophulariaceae / chemistry*
  • Staphylococcus aureus / drug effects

Substances

  • Anti-Bacterial Agents
  • Diterpenes