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

TitleSynthesis and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives.
Publication TypeJournal Article
Year of Publication2013
AuthorsLiu Q, Liu H, Zhang L, Guo T, Wang P, Geng M, Li Y
JournalEuropean journal of medicinal chemistry
Volume64
Pagination1-15
Date Published2013 Jun
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.

DOI10.1371/journal.pone.0081430
Alternate JournalEur J Med Chem