Antibacterial activity of labdane diterpenoids from Stemodia foliosa

J Nat Prod. 2008 Jul;71(7):1291-3. doi: 10.1021/np800106x. Epub 2008 Jun 27.

Abstract

As part of a continuing interest in exploring the chemistry of Brazilian medicinal plants, three new labdane diterpenoids, 6alpha-acetoxymanoyl oxide (1), 6alpha-malonyloxymanoyl oxide (2), and 6alpha-malonyloxy-n-butyl ester manoyl oxide (3), together with the known betulinic acid, lupeol, sitosterol, and stigmasterol, were isolated from the aerial parts of Stemodia foliosa. The structures of 1-3 were established on the basis of interpretation of spectroscopic data, including HRESIMS, and 1D and 2D NMR techniques. All compounds were tested against a bacteria panel consisting of Staphylococcus aureus, Bacillus cereus, B. subtilis, B. anthracis, Micrococcus luteus, Mycobacterium smegmatis, and M. phlei. Compound 2 showed moderate activity against these strains, with MIC values in the range 7-20 microg/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*
  • Bacillus anthracis / drug effects
  • Bacillus cereus / drug effects
  • Bacillus subtilis / drug effects
  • Betulinic Acid
  • Brazil
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Microbial Sensitivity Tests
  • Micrococcus luteus / drug effects
  • Molecular Structure
  • Mycobacterium phlei / drug effects
  • Mycobacterium smegmatis / drug effects
  • Pentacyclic Triterpenes
  • Plants, Medicinal / chemistry*
  • Scrophulariaceae / chemistry*
  • Sitosterols / isolation & purification
  • Staphylococcus aureus / drug effects
  • Stigmasterol / isolation & purification
  • Triterpenes / isolation & purification

Substances

  • 6alpha-acetoxymanoyl oxide
  • 6alpha-malonyloxy-n-butyl ester manoyl oxide
  • 6alpha-malonyloxymanoyl oxide
  • Anti-Bacterial Agents
  • Diterpenes
  • Pentacyclic Triterpenes
  • Sitosterols
  • Triterpenes
  • gamma-sitosterol
  • Stigmasterol
  • lupeol
  • Betulinic Acid