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

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Title
Olean-27-carboxylic acid-type triterpenes with potent antibacterial activity from Aceriphyllum rossii
Author(s)
C J Zheng; Mi Jin Sohn; Ki Young Kim; Hyung Eun Yu; Won Gon Kim
Bibliographic Citation
Journal of Agricultural and Food Chemistry, vol. 56, no. 24, pp. 11752-11756
Publication Year
2008
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 μg/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, 3α-hydroxyolean-12-en-27-oic acid, and 3β-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 μg/mL, while 3α-hydroxyolean-12-en-27-oic acid and 3β-hydroxyolean-12-en-27-oic acid exhibited a very weak activity, with MIC values of 128 μg/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.
Keyword
3-oxo-12-oleanen-27-oic acidAceriphyllic acid AAceriphyllum rossiiAntibacterial activityBactericidal
ISSN
0021-8561
Publisher
Amer Chem Soc
DOI
http://dx.doi.org/10.1021/jf802832w
Type
Article
Appears in Collections:
Division of Research on National Challenges > Infectious Disease Research Center > 1. Journal Articles
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