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Keywords = dioxoruthenium(VI) tetraphenylporphyrin

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16 pages, 610 KiB  
Review
Cytotoxic Activity of Ursolic Acid Derivatives Obtained by Isolation and Oxidative Derivatization
by Kishor Mazumder, Katsunori Tanaka and Koichi Fukase
Molecules 2013, 18(8), 8929-8944; https://doi.org/10.3390/molecules18088929 - 26 Jul 2013
Cited by 41 | Viewed by 9834
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 [...] Read more.
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. Full article
(This article belongs to the Section Natural Products Chemistry)
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