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Natural Product Research
Formerly Natural Product Letters
Volume 27, 2013 - Issue 8
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Research Article

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 Department of Organic Chemistry Faculty of Sciences, P.O. Box 812 University of Yaoundé 1, Yaoundé, CameroonCorrespondence[email protected]
,
Aurelie Vigee Barry Songfack Djoumessi Department of Organic Chemistry Faculty of Sciences, P.O. Box 812 University of Yaoundé 1, Yaoundé, Cameroon
,
Vincent Rincheval Laboratoire de Génétique et Biologie Cellulaire Bâtiment Fermat – Maison 4, University of Versailles St Quentin-en-Yvelines, Niveau 2; 45, Avenue des Etats-Unis, 78035 Versailles Cedex, France
,
Hervé Martial Poumale Poumale Department of Organic Chemistry Faculty of Sciences, P.O. Box 812 University of Yaoundé 1, Yaoundé, Cameroon
,
Berhanu M. Abegaz Department of Chemistry, University of Botswana, Private Bag 00704, Gaborone, Botswana
&
Bonaventure T. Ngadjui Department of Organic Chemistry Faculty of Sciences, P.O. Box 812 University of Yaoundé 1, Yaoundé, Cameroon; Department of Pharmaceutical Sciences and Traditional Pharmacopeia, Faculty of Medicine and Biomedical Sciences, University of Yaoundé I, P.O. Box. 8664, Yaoundé, Cameroon
Pages 711-718 | Received 25 Jan 2012, Accepted 04 Apr 2012, Published online: 23 May 2012
 
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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.

Acknowledgements

AVBD would like to thank NABSA (Network for Analytical and Bio-assay Services in Africa) for the financial support of a short term visit in the University of Gaberone, Botswana.

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