Antibacterial triterpenoid acids from Dillenia papuana

J Nat Prod. 1994 Sep;57(9):1245-50. doi: 10.1021/np50111a009.

Abstract

Three new oleanene-type triterpenoids, dillenic acids A [1], B [2], and C [3], and two known compounds, 3-oxoolean-1,12-dien-30-oic acid [4] (a new natural product) and the lupene derivative betulinaldehyde, have been isolated from the Papua New Guinean medicinal plant Dillenia papuana. The structures of the new compounds were elucidated as 2 alpha-hydroxy-3-oxoolean-12-en-30-oic acid, 2-oxo-3 beta-hydroxyolean-12-en-30-oic acid and 1 alpha-hydroxy-3-oxoolean-12-en-30-oic acid. The 1H- and 13C-nmr data of all new compounds were assigned unambiguously using a variety of 2D nmr experiments including 1H-1H-COSY, HMQC, HMBC, and NOESY experiments. Of these compounds, 1-4 showed antibacterial activities against Bacillus subtilis, Escherichia coli, and Micrococcus luteus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Bacillus subtilis / drug effects
  • Escherichia coli / drug effects
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Micrococcus luteus / drug effects
  • New Guinea
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / isolation & purification
  • Oleanolic Acid / pharmacology
  • Plant Leaves / chemistry
  • Plant Stems / chemistry
  • Plants, Medicinal / chemistry*
  • Spectrophotometry, Infrared
  • Trees / chemistry

Substances

  • Anti-Bacterial Agents
  • dillenic acid A
  • dillenic acid B
  • dillenic acid C
  • Oleanolic Acid