title: Cytotoxic activity of ursolic acid derivatives obtained by isolation and oxidative derivatization.
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.
authors.affiliation: Department of Pharmacy, University of Science and Technology Chittagong, Foy's Lake, Chittagong 4202, Bangladesh.
authors.forename: Kishor
authors.initials: K
authors.lastname: Mazumder
authors.forename: Katsunori
authors.initials: K
authors.lastname: Tanaka
authors.forename: Koichi
authors.initials: K
authors.lastname: Fukase
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006801:Humans; D010084:Oxidation-Reduction; D010936:Plant Extracts / Q000008:administration & dosage / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry; D011166:Porphyrins / Q000737:chemistry; D051381:Rats; D012878:Skin Neoplasms / Q000188:drug therapy* / Q000473:pathology; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000737:chemistry*; D000097245:Ursolic Acid
chemical_list: D010936:Plant Extracts; D011166:Porphyrins; D014315:Triterpenes; D000097245:Ursolic Acid; C409084:tetraphenylporphyrin; C113861:corosolic acid
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