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Influence of the side chain on the cytotoxicity of betulin derivatives

Katarzyna Sidoryk 1,2Anna Korda 2Piotr Cmoch 2Zbigniew Pakulski 2Lucie Rárová 3Jana Oklešťková 3Miroslav Strnad 3

1. Pharmaceutical Research Institute, Rydygiera 8, Warsaw 01-793, Poland
2. Polish Academy of Science, Institute of Organic Chemistry, Kasprzaka 44/52, Warszawa 01-224, Poland
3. Palacký University and Institute of Experimental Botany ASCR, Šlechtitelů 11, Olomouc 783 71, Czech Republic


Betulin (1) and betulinic acid (2) are natural compounds with proven anticancer, anti-bacterial, antimalarial, antiviral and anti-inflammatory activities [1, 2]. Recent investigations have demonstrated that even a simple modification of the structure can significantly increase their biological activity. Lupane saponins (triterpenes bearing sugar moiety at C-3 or C-28 positions) are also considered as very promising cytotoxic derivatives [3].

In this communication, we will report on the synthesis of new lupane derivatives as well as, novel lupane-type saponins. All new derivatives were examined for the cytotoxic activity against cancer cell lines of various histopathological origins, including T-lymphoblastic leukemia (CEM), breast carcinoma (MCF-7), and cervical carcinoma lines (HeLa) as well as normal fibroblasts (human BJ-H-tert). Our investigations demonstrate that the modifications at C-3 and/or C-28 positions of lupane triterpenes, and saponins obtained thereof, significantly influence the cytotoxic activity of the resulting new compounds. Structure-activity relationships will also be discussed.

The support from the National Science Centre (Grant No. 2012/07/B/ST5/00823) is acknowledged.

[1] Sami A., Taru M., Salme K., Jari Y.K., Eur J. Pharm. Sci. 2006, 29, 1-13.
[2] Moghaddam M.G., Faujan B.H. Ahmad, Samzadeh-Kermani A., Pharmacology & Pharmacy 2012, 3, 119-123.
[3] Cmoch, P., Korda, A., Rárová, L., Oklešťková, J., Strnad, M., Luboradzki, R., Pakulski, Z., Tetrahedron 2014, 70, 2717-2730.


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Submitted: 2014-03-31 09:42
Revised:   2014-05-02 18:58