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

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.

Keywords:

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.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

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

Information for

Open access

Opportunities

Help and information

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

Abstract

Acknowledgements

Reprints and Corporate Permissions

Academic Permissions

Related research

To cite this article:

Download citation

Information for

Open access

Opportunities

Help and information

Keep up to date

Your download is now in progress and you may close this window

Login or register to access this feature

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