title: Synthesis and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives.
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.
authors: Department of Pharmaceutical Engineering, Northwest University, Xi'an 710069, China.
authors: Qingchao
authors: Q
authors: Liu
authors: Hongchun
authors: H
authors: Liu
authors: Lei
authors: L
authors: Zhang
authors: Tiantian
authors: T
authors: Guo
authors: Peng
authors: P
authors: Wang
authors: Meiyu
authors: M
authors: Geng
authors: Yingxia
authors: Y
authors: Li
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006801:Humans; D008968:Molecular Conformation; D009828:Oleanolic Acid / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D012503:Saponins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D012503:Saponins; D014315:Triterpenes; D009828:Oleanolic Acid