Natural Product Research 2013-04-01

Cytotoxicity of semisynthetic acetal triterpenes from one-pot vicinal diol cleavage following by lactolization: reaction promoted by NaIO4/SiO2 gel in THF.

Louis Pergaud Sandjo, Aurelie Vigee Barry Songfack Djoumessi, Vincent Rincheval, Hervé Martial Poumale Poumale, Berhanu M Abegaz, Bonaventure T Ngadjui

Index: Nat. Prod. Res. 27(8) , 711-8, (2013)

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Abstract

In situ C-C bond cleavage of vicinal diol following by the lactolisation resulted from separated treatment of Arjunolic acid (1), 24-hydroxytormentic acid (2) and 3-O-β-D-glucopyranosylsitosterol (3) with sodium periodate and silica gel in dried THF according to the strategic position of hydroxyl functions in the molecule. The reaction led to a lactol pentacyclic triterpenes 1A, 2A and a bicyclotriacetal of β-sitosterol 3A. These products were further acetylated and the cytotoxicity of all molecules was evaluated against human fibrosarcoma HT1080 cancer cells lines.