Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins

• Published in: Carbohydrate research 2010-03, Vol.345 (5), p.607-620
• Main Authors: Wang, Peng, Wang, Jun, Guo, TianTian, Li, Yingxia
• Format: Article
• Language: English
• Subjects: Acetylglucosamine - chemistry; Antineoplastic Agents, Phytogenic - chemical synthesis; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - pharmacology; Cell Proliferation - drug effects; Cytotoxic activity; HL-60 Cells; Humans; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure; N-Acetylglucosamine; Oleanolic acid; Oleanolic Acid - chemical synthesis; Oleanolic Acid - chemistry; Oleanolic Acid - pharmacology; Saponin; Saponins - chemical synthesis; Saponins - chemistry; Saponins - pharmacology; Stomach Neoplasms - drug therapy; Triterpenes - chemical synthesis; Triterpenes - chemistry; Triterpenes - pharmacology; Tumor Cells, Cultured; Ursolic Acid
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2010.01.002

Fourteen ursolic acid and oleanolic acid saponins, where R = GlcNAc or (1→4)-linked and (1→6)-linked GlcNAc oligosaccharide residues were synthesized in a convergent manner and evaluated for their cytotoxic activity in three cancer cell lines. R 1 and R 2 = H or CH 3. Fourteen ursolic acid and oleanolic acid saponins with N-acetyl-β- d-glucosamine, and (1→4)-linked and (1→6)-linked N-acetyl-β- d-glucosamine oligosaccharide residues were synthesized in a convergent manner. The structures of all compounds were confirmed by 1H NMR and 13C NMR spectroscopy and by mass spectrometry, and their cytotoxic activities were assayed in three cancer cell lines. Only oleanolic acid-3-yl β- d-GluNAc showed significant cytotoxicity against HL-60 and BGC-823.