title: Synthesis of oleanolic acid saponins mimicking components of Chinese folk medicine Di Wu.
abstract: 3,28-Di-O-rhamnosylated oleanolic acid saponins, mimicking components of Chinese folk medicine Di Wu, have been designed and synthesized. One-pot glycosylation and 'inverse procedure' technologies have been applied thus significantly simplifying the preparation of desired saponins. The cytotoxic activity of compounds 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester (3), 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl- (1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester (4), 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl] ester (5), and 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[6-O-(alpha-L-rhamnopyranosyl)hexyl] ester (6) was preliminarily evaluated against HL-60 human promyelocytic leukemia cells. The natural saponin 3 and designed saponin 4 exhibited comparable moderate cytotoxic activity under our testing conditions.
authors.affiliation: Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.
authors.forename: Xing
authors.initials: X
authors.lastname: Huang
authors.forename: Shuihong
authors.initials: S
authors.lastname: Cheng
authors.forename: Yuguo
authors.initials: Y
authors.lastname: Du
authors.forename: Feihong
authors.initials: F
authors.lastname: Bing
mesh_terms: D000818:Animals; D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D049109:Cell Proliferation / Q000187:drug effects; D015195:Drug Design; D004365:Drugs, Chinese Herbal / Q000737:chemistry*; D018922:HL-60 Cells; D006801:Humans; D008516:Medicine, Chinese Traditional; D009828:Oleanolic Acid / Q000737:chemistry*; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D004365:Drugs, Chinese Herbal; D012503:Saponins; C543134:di wu; D009828:Oleanolic Acid