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Eur J Med Chem. 2013 Jun;64:1-15. doi: 10.1016/j.ejmech.2013.04.016. Epub 2013 Apr 15.

Synthesis and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives.

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  • 1Department of Pharmaceutical Engineering, Northwest University, Xi'an 710069, China.

Abstract

Twenty-six naturally occurring oleanolic acid saponins and their derivatives, 16 of which were synthesized in this study, were preliminarily evaluated against human cancer cells. From SAR studies, the presence of α-l-rhamnosyl residue at the terminal of both C-3 and C-28 position for oleanolic acid bidesmosides was important to enhance cytotoxicity, and introducing more sugar residues at C3-OH of compound 12 with C-28 carboxylic acid is a favorable modification to ameliorate the anticancer activity. Furthermore, α-l-rhamnosyl moiety linked to C2-OH of the first monosaccharide (α-l-alabinose, β-d-xylose, β-d-galactose or β-d-glucose) in C3-OH of oleanolic acid was helpful to improve the cytotoxicity. According to the predicted log P values, lipophilicity of the synthesized saponins was not an important factor for cytotoxicity.

Copyright © 2013 Elsevier Masson SAS. All rights reserved.

PMID:
23639650
[PubMed - indexed for MEDLINE]
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