Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins.
Fourteen ursolic acid and oleanolic acid saponins with N-acetyl-beta-D-glucosamine, and (1-->4)-linked and (1-->6)-linked N-acetyl-beta-D-glucosamine oligosaccharide residues were synthesized in a convergent manner. The structures of all compounds were confirmed by (1)H NMR and (13)C NMR spectroscopy and by mass spectrometry, and their cytotoxic activities were assayed in three cancer cell lines. Only oleanolic acid-3-yl beta-D-GluNAc showed significant cytotoxicity against HL-60 and BGC-823.
Wang
Peng
P
School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China.
Wang
Jun
J
Guo
TianTian
T
Li
Yingxia
Y
D000117:Acetylglucosamine / Q000737:chemistry*; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects*; D018922:HL-60 Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009828:Oleanolic Acid / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013274:Stomach Neoplasms / Q000188:drug therapy*; D014315:Triterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D014407:Tumor Cells, Cultured; D000097245:Ursolic Acid
D000117:Acetylglucosamine; D000972:Antineoplastic Agents, Phytogenic; D009828:Oleanolic Acid; D012503:Saponins; D014315:Triterpenes; D000097245:Ursolic Acid