Auxiliary-directed oxidation of ursolic acid by ‘Ru’-porphyrins: chemical modulation of cytotoxicity against tumor cell lines

Auxiliary-directed oxidation of ursolic acid by ‘Ru’-porphyrins: chemical modulation of cytotoxicity against tumor cell lines

Derivatization of ursolic acid, one of the natural ursene-type pentacyclic triterpenes, was investigated by the oxidation with dioxoruthenium(VI) tetraphenylporphyrins. Oxidation selectivity on the terpene structure was modulated by the auxiliaries introduced on the tetraphenylporphyrin. Chemical ox...

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Veröffentlicht in:Tetrahedron letters 2012-04, Vol.53 (14), p.1756-1759
Hauptverfasser: Tanaka, Katsunori, Mazumder, Kishor, Siwu, Eric R.O., Nozaki, Satoshi, Watanabe, Yasuyoshi, Fukase, Koichi
Format: Artikel
Sprache:eng
Schlagworte:
Biomimetic oxidation
Biotechnology
Cytochrome P450
Cytotoxicity
Dioxoruthenium(VI) tetraphenylporphyrin
Modulation
Oxidation
Selectivity
Terpenes
Tetrahedrons
Tumors
Ursolic acid
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Beschreibung
Zusammenfassung:Derivatization of ursolic acid, one of the natural ursene-type pentacyclic triterpenes, was investigated by the oxidation with dioxoruthenium(VI) tetraphenylporphyrins. Oxidation selectivity on the terpene structure was modulated by the auxiliaries introduced on the tetraphenylporphyrin. Chemical oxidation of the ursolic acid affected the cytotoxic activity against tumor cell lines.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.01.107