Olean-27-carboxylic acid-type triterpenes with potent antibacterial activity from Aceriphyllum rossii.
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.
Zheng
Chang-Ji
CJ
Functional Metabolites Research Center, Korea Research Institute of Bioscience and Biotechnology, Post Office Box 115, Yusong, Daejeon 305-806, Korea.
Sohn
Mi-Jin
MJ
Kim
Ki-Young
KY
Yu
Hyung-Eun
HE
Kim
Won-Gon
WG
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D002264:Carboxylic Acids / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D006801:Humans; D009828:Oleanolic Acid / Q000737:chemistry / Q000494:pharmacology*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D031995:Saxifragaceae / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D002264:Carboxylic Acids; D010936:Plant Extracts; D009828:Oleanolic Acid