Antibacterial triterpenoids from Dillenia papuana and their structure-activity relationships

Phytochemistry. 1995 Dec;40(6):1691-5. doi: 10.1016/0031-9422(95)00491-o.

Abstract

Two new oleanene-type triterpenoids, dillenic acids D and E, have been isolated from the leaves and stems of Dillenia papuana together with the new natural product 3-oxoolean-12-en-30-oic acid. Together with these compounds, the known compound, betulinic acid (3 beta-hydroxy-20(29)-lupen-28-oic acid) was isolated as the major component of the fractions studied. Dillenic acids D and E were characterized as 2,3-seco-2-oxoolean-12-en-3-methylester-30-oic acid and 1 alpha,3 beta-dihydroxyolean-12-en-30-oic acid and their nuclear magnetic resonance data were unambiguously assigned using two-dimensional nuclear magnetic resonance techniques. A comparison of antibacterial activities of these compounds with the earlier reported dillenic acids A-C indicated that, aside from a double bond in gamma- or delta-position to a carboxylic group, a ketone function in ring A of an oleanene-skeleton may be required for the observed activity.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Escherichia coli / drug effects*
  • Escherichia coli / growth & development
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Microbial Sensitivity Tests
  • Micrococcus luteus / drug effects*
  • Micrococcus luteus / growth & development
  • Molecular Structure
  • Plant Leaves
  • Plant Stems
  • Plants, Medicinal*
  • Structure-Activity Relationship
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Triterpenes