TY - JOUR
T1 - Cytotoxic activity of ursolic acid derivatives obtained by isolation and oxidative derivatization
AU - Mazumder, Kishor
AU - Tanaka, Katsunori
AU - Fukase, Koichi
PY - 2013/8/1
Y1 - 2013/8/1
N2 - 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.
AB - 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.
KW - A431 human skin carcinoma cell line
KW - Biomimetic oxidation
KW - C6 rat glioma cell line
KW - Cytochrome P450
KW - Cytotoxicity
KW - Dioxoruthenium(VI) tetraphenylporphyrin
KW - Saurauja roxburghii
KW - Ursolic acid
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U2 - 10.3390/molecules18088929
DO - 10.3390/molecules18088929
M3 - Review article
C2 - 23896618
AN - SCOPUS:84883157800
VL - 18
SP - 8929
EP - 8944
JO - Molecules
JF - Molecules
SN - 1420-3049
IS - 8
ER -