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Cytotoxic Activity of Ursolic Acid Derivatives Obtained by Isolation and Oxidative Derivatization
Department of Pharmacy, University of Science and Technology Chittagong, Foy's Lake, Chittagong 4202, Bangladesh
Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan
RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan
* Author to whom correspondence should be addressed.
Received: 14 June 2013; in revised form: 22 July 2013 / Accepted: 24 July 2013 / Published: 26 July 2013
Abstract: Structure-activity relationships of ursane-type pentacyclic triterpenes obtained from natural sources and by chemical derivatization are reviewed. Ursolic acid, corosolic acid, and a new ursane-type pentacyclic triterpene, 7,24-dihydroxyursolic acid, were isolated from the methanolic extract of the leaves of the Bangladeshi medicinal plant, Saurauja roxburghii. Derivatization of ursolic acid by oxidation with dioxoruthenium (VI) tetraphenylporphyrins was investigated. Oxidation selectivity on the terpene structure was modulated by the auxiliaries introduced on the tetraphenylporphyrin. The natural triterpenes and oxidized derivatives were tested for cytotoxicity against the C6 rat glioma and A431 human skin carcinoma cell lines. Although they have the same ursane-type pentacyclic triterpene cores, the position and numbers of hydroxyls on the terpene structures significantly affected the activity and the selectivity towards the tested cell lines.
Keywords: ursolic acid; Saurauja roxburghii; cytotoxicity; C6 rat glioma cell line; A431 human skin carcinoma cell line; dioxoruthenium(VI) tetraphenylporphyrin; biomimetic oxidation; cytochrome P450
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Mazumder, K.; Tanaka, K.; Fukase, K. Cytotoxic Activity of Ursolic Acid Derivatives Obtained by Isolation and Oxidative Derivatization. Molecules 2013, 18, 8929-8944.
Mazumder K, Tanaka K, Fukase K. Cytotoxic Activity of Ursolic Acid Derivatives Obtained by Isolation and Oxidative Derivatization. Molecules. 2013; 18(8):8929-8944.
Mazumder, Kishor; Tanaka, Katsunori; Fukase, Koichi. 2013. "Cytotoxic Activity of Ursolic Acid Derivatives Obtained by Isolation and Oxidative Derivatization." Molecules 18, no. 8: 8929-8944.