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Synthesis and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives.
|Title||Synthesis and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives.|
|Publication Type||Journal Article|
|Year of Publication||2013|
|Authors||Liu Q, Liu H, Zhang L, Guo T, Wang P, Geng M, Li Y|
|Journal||European journal of medicinal chemistry|
|Date Published||2013 Jun|
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.
|Alternate Journal||Eur J Med Chem|