Facile Synthesis and Antitumor Activities of Timosaponin AIII and Its Analogs

REFERENCES

• Takahashi , M. , Konno , C. and Hikino , H. 1985 . Mechanism of antihepatotoxic activity of atractylon, I: Effect on free radical generation and lipid peroxidation . Planta Med. , 51 : 100 – 102 .
   Web of Science ®Google Scholar
• Niwa , A. , Takeda , O. , Ishimaru , M. , Nakamoto , Y. , Yamasaki , K. , Kohda , H. , Nishino , H. , Segawa , T. , Fujimura , K. and Kurimoto , A. 1988 . Screening test for platelet aggregation inhibitor in natural products. The active principle of anemarrhenae rhizoma . Yakugaku Zasshi , 108 : 555 – 561 .
   PubMed Web of Science ®Google Scholar
• Bhattacharya , S. K. , Ghosal , S. , Chandhuri , R. K. and Sanyal , A. K. 1972 . Canscora decussata (Gentianaceae) xanthones III: pharmacological studies . J. Pharm. Sci. , 61 : 1838 – 1840 .
   Web of Science ®Google Scholar
• Kawasaki , T. and Yamauchi , T. 1963 . Saponin of timo (anemarrhenae rhizoma). II. Structure of timosaponin A-III . Chem. Pharm. Bull. , 11 : 1221 – 1224 .
   PubMedGoogle Scholar
• Zhang , J. , Meng , Z. , Zhang , M. , Ma , D. , Xu , S. and Kodama , H. 1999 . Effect of six steroidal saponins isolated from anemarrhenae rhizoma on platelet aggregation and hemolysis in human blood . Clin. Chim. Acta. , 289 : 79 – 88 .
   PubMed Web of Science ®Google Scholar
• Wang , G. J. , Lin , L. C. , Chen , C. F. , Cheng , J. S. , Lo , Y. K. , Chou , K. J. , Lee , K. C. , Liu , C. P. , Wu , Y. Y. , Su , W. , Chen , W. C. and Jan , C. R. 2002 . Effect of timosaponin A-III, from Anemarrhenae asphodeloides Bunge (Liliaceae), on calcium mobilization in vascular endothelial and smooth muscle cells and on vascular tension . Life Sci. , 71 : 1081 – 1090 .
   PubMed Web of Science ®Google Scholar
• Zhang , J. , Zhang , M. , Sugahara , K. , Sagara , Y. , Meng , Z. , Xu , S. and Kodama , H. 1999 . Effect of steroidal saponins of Anemarrhenae rhizoma on superoxide generation in human neutrophils . Biochem. Biophy. Res. Commun. , 259 : 636 – 639 .
   PubMed Web of Science ®Google Scholar
• Lee , B. , Jung , K. and Kim , D. H. 2009 . Timosaponin AIII, a saponin isolated from Anemarrhena asphodeloides, ameliorates learning and memory deficits in mice . Pharmacol. Biochem. Behav. , 93 : 121 – 127 .
   PubMed Web of Science ®Google Scholar
• Sy , L. K. , Yan , S. C. , Lok , C. N. , Man , R. Y.K. and Che , C. M. 2008 . Timosaponin A-III induces autophagy preceding mitochondria-mediated apoptosis in HeLa cancer cells . Cancer Res. , 68 : 10229 – 10237 .
   PubMed Web of Science ®Google Scholar
• King , F. W. , Fong , S. , Griffin , C. , Shoemaker , M. , Staub , R. , Zhang , Y. L. , Cohen , I. and Shtivelman , E. 2009 . Timosaponin AIII is preferentially cytotoxic to tumor cells through inhibition of mTOR and induction of ER stress . PLoS One , 4 : 1 – 12 .
   Google Scholar
• Kang , Y.-J. , Chung , H.-J. , Nam , J.-W. , Park , H. J. , Seo , E. K. , Kim , Y. S. , Lee , D. and Lee , S. K. 2011 . Cytotoxic and antineoplastic activity of timosaponin A-III for human colon cancer cells . J. Nat. Prod. , 74 : 701 – 706 .
   PubMed Web of Science ®Google Scholar
• Koeller , K. M. and Wong , C.-H. 2000 . Synthesis of complex carbohydrates and glycoconjugates: enzyme-based and programmable one-pot strategies . Chem. Rev. , 100 : 4465 – 4493 .
   PubMed Web of Science ®Google Scholar
• Wang , Y. , Ye , X.-S. and Zhang , L.-H. 2004 . A four-component one-pot synthesis of α-Gal pentasaccharide . Org. Lett. , 6 : 4415 – 4417 .
   PubMed Web of Science ®Google Scholar
• Yu , B. , Yang , Z. and Cao , H. 2005 . One-pot glycosylation (OPG) for the chemical synthesis of oligosaccharides . Curr. Org. Chem. , 9 : 179 – 194 .
   Web of Science ®Google Scholar
• Miermont , A. , Zeng , Y. , Jing , Y. , Ye , X.-S. and Huang , X. 2007 . Syntheses of Lewisx and dimeric Lewisx: construction of branched oligosaccharides by a combination of preactivation and reactivity based chemoselective one-pot glycosylations . J. Org. Chem. , 72 : 8958 – 8961 .
   PubMed Web of Science ®Google Scholar
• Wang , Y. , Ye , X.-S. and Zhang , L.-H. 2007 . Oligosaccharide assembly by one-pot multi-step strategy . Org. Biomol. Chem. , 5 : 2189 – 2200 .
   PubMed Web of Science ®Google Scholar
• Du , Y. , Gu , G. , Wei , G. , Hua , Y. and Linhardt , R. J. 2003 . Synthesis of saponins using partially protected glycosyl donors . Org. Lett. , 5 : 3627 – 3630 .
   PubMed Web of Science ®Google Scholar
• Gu , G. , Du , Y. and Linhardt , R. J. 2004 . Facile synthesis of saponins containing 2,3-branched oligosaccharides by using partially protected glycosyl donors . J. Org. Chem. , 69 : 5497 – 5500 .
   PubMed Web of Science ®Google Scholar
• Wei , G. , Wang , J. and Du , Y. 2011 . Total synthesis of solamargine . Bioorg. Med. Chem. Lett. , 21 : 2930 – 2933 .
   PubMed Web of Science ®Google Scholar
• Cheng , S. , Du , Y. , Ma , B. and Tan , D. 2009 . Total synthesis of a furostan saponin, timosaponin BII . Org. Biomol. Chem. , 7 : 3112 – 3118 .
   Web of Science ®Google Scholar
• Sato , Y. , Ikekawa , N. and Mosettig , E. 1960 . The chemistry of the spiroaminoketal side chain of solasodine and tomatidine. I. Improved preparation of 3β-acetoxy-5,16-pregnadien-20-one and 3β-acetoxy-5α-pregn-16-en-20-one from solasodine and tomatidine . J. Org. Chem. , 25 : 783 – 786 .
   Web of Science ®Google Scholar
• Shi , C.-S. and Kehrl , J. H. 2004 . Pyk2 amplifies epidermal growth factor and c-Src-induced Stat3 activation . J. Biol. Chem. , 279 : 17224 – 17231 .
   PubMed Web of Science ®Google Scholar