| Modification of Sugar Chains in Glycoalkaloids and Variation of Anticancer Activity |
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| 作者姓名： | LI Sheng-yu HE Da-jun ZHANG Xu NI Wei-hua ZHOU Yi-fa ZHANG Li-ping |
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| 作者单位： | LI Sheng-yu，HE Da-jun，ZHANG Xu，NI Wei-hua，ZHOU Yi-fa and ZHANG Li-pingSchool of Life Sciences，Northeast Normal University，Changchun 130024，P. R. China |
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| 基金项目： | 国家自然科学基金，吉林省教育厅自然科学基金 |
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| 摘 要： | To study the effect of the sugar chains in glycoalkaloids against cancer cells, 6-O-sulfated solamargine and acid-catalyzed hydrolytic products of α-solamargine and α-solasonine were prepared. The sulfation at O-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-O-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.
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| 关 键 词： | 配糖生物碱 糖链修饰 抗癌活性变化 硫酸盐化作用 酸解 |
| 收稿时间： | 12 October 2006 |
| 修稿时间： | 2006-10-12 |
Modification of Sugar Chains in Glycoalkaloids and Variation of Anticancer Activity |
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| LI Sheng-yu HE Da-jun ZHANG Xu NI Wei-hua ZHOU Yi-fa ZHANG Li-ping.Modification of Sugar Chains in Glycoalkaloids and Variation of Anticancer Activity[J].Chemical Research in Chinese University,2007,23(3):303-309. |
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| Authors: | Sheng-yu Li Da-jun HE Xu ZHANG Wei-hua NI Yi-fa ZHOU Li-ping ZHANG |
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| Institution: | aSchool of Life Sciences, Northeast Normal University, Changchun 130024, P. R. China |
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| Abstract: | To study the effect of the sugar chains in glycoalkaloids against cancer cells, 6-O-sulfated solamargine and acid-catalyzed hydrolytic products of α-solamargine and α-solasonine were prepared. The sulfation at O-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-O-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. |
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| Keywords: | Solamargine Solasonine Anticancer Sulfation Acidic hydrolysis |
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