期刊文献+

Modification of Sugar Chains in Glycoalkaloids and Variation of Anticancer Activity 被引量:4

Modification of Sugar Chains in Glycoalkaloids and Variation of Anticancer Activity
下载PDF
导出
摘要 To study the effect of the sugar chains in glycoalkaloids against cancer cells, 6-0-sulfated solamargine and acidcatalyzed hydrolytic products of α-solamargine and α-solasonine were prepared. The sulfation at 0-6 of solamargine was proceeded in five steps. The 6-OH group was first selectively protected with DMT-Cl, and then the secondary hydroxyl groups on the sugar ring were acetylated. After the protective group DMTr was removed, the free 6-OH group was sulfated. Finally, the acetyl groups were removed to give 6-0-sulfated solamargine in a good yield. The hydrolyses of solamargine and solasonine were performed in diluted hydrogen chlorede. Three and two hydrolyzed products were obtained from solamargine and solasonine, respectively. The antiproliferative activities against HCT-8 tumor cells of two glycoalkaloids and their derivaties were examined via a MTT assay. The results show that α-solamargine and α-solasonine exhibit strong cytotoxic activities with an IC50 of 10. 63 and 11.97 μmol/L, respectively, wheras their derivaties seem to be less activities. To study the effect of the sugar chains in glycoalkaloids against cancer cells, 6-0-sulfated solamargine and acidcatalyzed hydrolytic products of α-solamargine and α-solasonine were prepared. The sulfation at 0-6 of solamargine was proceeded in five steps. The 6-OH group was first selectively protected with DMT-Cl, and then the secondary hydroxyl groups on the sugar ring were acetylated. After the protective group DMTr was removed, the free 6-OH group was sulfated. Finally, the acetyl groups were removed to give 6-0-sulfated solamargine in a good yield. The hydrolyses of solamargine and solasonine were performed in diluted hydrogen chlorede. Three and two hydrolyzed products were obtained from solamargine and solasonine, respectively. The antiproliferative activities against HCT-8 tumor cells of two glycoalkaloids and their derivaties were examined via a MTT assay. The results show that α-solamargine and α-solasonine exhibit strong cytotoxic activities with an IC50 of 10. 63 and 11.97 μmol/L, respectively, wheras their derivaties seem to be less activities.
出处 《Chemical Research in Chinese Universities》 SCIE CAS CSCD 2007年第3期303-309,共7页 高等学校化学研究(英文版)
基金 Supported by the National Natural Science Foundation of China(No30570417) the Natural Science Foundation of JilinProvince(No20040546)
关键词 SOLAMARGINE Solasonine ANTICANCER SULFATION Acidic hydrolysis Solamargine Solasonine Anticancer Sulfation Acidic hydrolysis
  • 相关文献

参考文献22

  • 1Roddick J. G., Steroidal Glycoalkaloids: Nature and Consequences of Bioactivity, Plenum Press, New York, 1996, 277
  • 2Alison M. F., Roddick J. G., Weissenberg M., Phytochemistry, 1994, 37(4), 1007
  • 3Alison M. F., Roddick J. G., Phytochemistry, 1993, 33(2), 323
  • 4Thorne H. V., Clarke G. F., Antiviral Res., 1985, 5(6), 335
  • 5Wanyonyi A. W., Chhabra S. C., Mkoji G., et al., Fitoterapia, 2003, 74(3), 298
  • 6Rayburn J. R., Friedman M., Bantle J. A., Food Chem. To-xicol., 1995, 33(12), 1013
  • 7Blankemeyer J. T., Mcwilliams M. L., Rayburn J. R., et al., Food Chem. Toxicol., 1998, 36(5), 383
  • 8Hsu S. H., Tsai T. R., Lin C. N., et al., Biochem. and Biophysi. Res. Commun., 1996, 229(1), 1
  • 9Kuo K. W., Hsu S. H., Li Y. P., et al., Biochem. Pharmacol., 2000, 60(12), 1865
  • 10Esteves S. A., Sarmento da Silva T. M., Alves C. C. F., et al., J. Braz. Chem. Soc., 2002, 13(6), 838

同被引文献22

引证文献4

二级引证文献23

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部