2-O-(2-chlorobenzoyl) maslinic acid triggers apoptosis in A2780 human ovarian carcinoma cells

Eur J Med Chem. 2019 Oct 15:180:457-464. doi: 10.1016/j.ejmech.2019.07.049.

Immo Serbian ¹, Bianka Siewert ², Ahmed Al-Harrasi ³, René Csuk ⁴

Affiliations

1 Martin-Luther-University Halle-Wittenberg Organic Chemistry, Kurt-Mothes-Str. 2, D-06120, Halle (Saale), Germany. Electronic address: immo.serbian@chemie.uni-halle.de.
2 University of Innsbruck, Institute of Pharmacy/Pharmacognosy, Center for Molecular Biosciences Innsbruck (CMBI), Center for Chemistry and Biomedicine, Innrain 80-82, A-6020, Innsbruck, Austria. Electronic address: bianka.siewert@uibk.ac.at.
3 University of Nizwa, Natural and Medical Sciences Center, P.O. Box 33, Birkat Al Mauz, Nizwa, 616, Oman. Electronic address: aharrasi@unizwa.edu.om.
4 Martin-Luther-University Halle-Wittenberg Organic Chemistry, Kurt-Mothes-Str. 2, D-06120, Halle (Saale), Germany. Electronic address: rene.csuk@chemie.uni-halle.de.

PMID: 31330447 DOI: 10.1016/j.ejmech.2019.07.049

Abstract

Depending on the conditions of the reactions, maslinic acid can be converted into the corresponding 2-O-, 3-O-, or 2,3-di-O-acylated compounds in good yields. These compounds showed in SRB assays a significantly increased cytotoxicity as compared to the parent compound maslinic acid. For the most active compound of this series, i.e. 2-O-(2-chlorobenzoyl) maslinic acid (5), more detailed cell biological tests (i.e. AO/PI dye exclusion experiments, an annexin V assay, and microscopic investigations) on A2780 (human ovarian carcinoma cells) revealed that this compound triggers Apoptosis.

Keywords

Acylation; Apoptosis; Cytotoxicity; Maslinic acid; Triterpenoids.

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