Olean-27-carboxylic acid-type triterpenes with potent antibacterial activity from Aceriphyllum rossii

J Agric Food Chem. 2008 Dec 24;56(24):11752-6. doi: 10.1021/jf802832w.

Abstract

Aceriphyllum rossii Engler (Saxifragaceae) have been used as a nutritious food in Korea. We found that the methanol extract of the root portion of A. rossii potently inhibited the growth of Staphylococcus aureus , with a minimal inhibitory concentration (MIC) value of 8 microg/mL. Using mass spectrometry and nuclear magnetic resonance (NMR) studies, four active constituents were isolated and identified: aceriphyllic acid A, 3-oxoolean-12-en-27-oic acid, 3alpha-hydroxyolean-12-en-27-oic acid, and 3beta-hydroxyolean-12-en-27-oic acid. Aceriphyllic acid A and 3-oxoolean-12-en-27-oic acid showed a potent antibacterial activity against several strains of S. aureus , including methicillin-resistant S. aureus and quinolone-resistant S. aureus , with MIC values of 2-8 microg/mL, while 3alpha-hydroxyolean-12-en-27-oic acid and 3beta-hydroxyolean-12-en-27-oic acid exhibited a very weak activity, with MIC values of 128 microg/mL. The methyl ester derivative of aceriphyllic acid A lost its antibacterial activity. The time-kill study against S. aureus indicated that aceriphyllic acid A had rapid bactericidal activity. These results indicated that aceriphyllic acid A and 3-oxoolean-12-en-27-oic acid are the most active principles, and both the carboxylic group at C-27 and the hydroxyl group at C-24 in aceriphyllic acid A are critical for the rapid bactericidal activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Bacteria / drug effects*
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / pharmacology*
  • Cell Line
  • Humans
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / pharmacology*
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Saxifragaceae / chemistry*

Substances

  • Anti-Bacterial Agents
  • Carboxylic Acids
  • Plant Extracts
  • Oleanolic Acid