title: Synthesis and Evaluation of a Series of Oleanolic Acid Saponins as α-Glucosidase and α-Amylase Inhibitors.
abstract: Sixteen naturally occurring oleanolic acid saponins and their derivatives were synthesized in an efficient and practical strategy, and their inhibitory activities against α-glucosidase and α-amylase were evaluated in vitro. Among all the compounds, 28-O-monoglucoside 8 exhibited remarkably potent inhibitory activity against α-glucosidase with an IC50 value of 87.3 µM, which was fivefold stronger than that of the antidiabetic acarbose. Based on the preliminary structure-activity relationships, for 28-O-monoglucosides, the presence of a terminal α-l-rhamnopyranosyl residue enhanced the α-glucosidase and α-amylase inhibitory activities. Furthermore, for 3,28-O-bidesmosides, sugar-substituted moieties attached to the C-3 and C-28 positions of the oleanolic acid scaffold are helpful to increase the inhibitory activities against α-amylase and α-glucosidase.
authors.affiliation: Department of Pharmaceutical Engineering, Northwest University, Xi'an, Shaanxi, P. R. China.
authors.forename: Tiantian
authors.initials: T
authors.lastname: Guo
authors.affiliation: Sorbonne Universités, UPMC University, Paris, France.
authors.forename: Shaoping
authors.initials: S
authors.lastname: Wu
authors.affiliation: Department of Pharmaceutical Engineering, Northwest University, Xi'an, Shaanxi, P. R. China.
authors.forename: Sen
authors.initials: S
authors.lastname: Guo
authors.affiliation: Department of Pharmaceutical Engineering, Northwest University, Xi'an, Shaanxi, P. R. China.
authors.forename: Lu
authors.initials: L
authors.lastname: Bai
authors.affiliation: Department of Pharmaceutical Engineering, Northwest University, Xi'an, Shaanxi, P. R. China.|Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong, P. R. China.
authors.forename: Qingchao
authors.initials: Q
authors.lastname: Liu
authors.affiliation: Department of Pharmaceutical Engineering, Northwest University, Xi'an, Shaanxi, P. R. China.
authors.forename: Naisheng
authors.initials: N
authors.lastname: Bai
mesh_terms: D020909:Acarbose / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D065089:Glycoside Hydrolase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D015394:Molecular Structure; D009828:Oleanolic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*; D012503:Saponins / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D000516:alpha-Amylases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D000520:alpha-Glucosidases / Q000378:metabolism*
chemical_list: D000970:Antineoplastic Agents; D065089:Glycoside Hydrolase Inhibitors; D012503:Saponins; D009828:Oleanolic Acid; D000516:alpha-Amylases; D000520:alpha-Glucosidases; D020909:Acarbose
keywords: Glycosylation; Oleanolic acid saponin; Synthesis; α-Amylase; α-Glucosidase