Synthesis of oleanolic acid saponins mimicking components of Chinese folk medicine Di Wu.
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.
Huang
Xing
X
Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.
Cheng
Shuihong
S
Du
Yuguo
Y
Bing
Feihong
F
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
D004365:Drugs, Chinese Herbal; D012503:Saponins; C543134:di wu; D009828:Oleanolic Acid