| 6-O-Sulfated Modification of Natural Glycoalkaloids Chaconine and Solanine |
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| 作者姓名： | ZHAO Ji-min LI Sheng-yu ZHOU Yi-fa ZHANG Li-ping ZHOU Dao-wei |
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| 作者单位： | ZHAO Ji-min 1，2，LI Sheng-yu 1，ZHOU Yi-fa 1，ZHANG Li-ping 1 and ZHOU Dao-wei 1**1. School of Life Sciences，Northeast Normal University，Changchun 130024，P. R. China; 2. Department of Biology，Changchun Normal College，Changchun，130032，P. R. China |
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| 基金项目： | the National Natural Science Foundation of China，吉林省自然科学基金 |
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| 摘 要： | Introduction Glycoalkaloids(GAS)arepotentiallytoxicsecond aryplantmetabolitesfoundinpotatoes,tomatoesand eggplants1].Someinvestigationshaveindicatedthat glycoalkaloidsmusthavebeenevolvedinnaturetopro tectplantsagainstbacteria,fungi,insects,andani mals.Th…
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| 关 键 词： | 6-O-硫酸盐改性 卡茄碱 茄碱 硫酸盐化作用 甘油生物碱 药物活性 |
| 文章编号： | 1005-9040（2006）-02-189-04 |
| 收稿时间： | 2005-12-31 |
6-O-Sulfated Modification of Natural Glycoalkaloids Chaconine and Solanine |
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| ZHAO Ji-min LI Sheng-yu ZHOU Yi-fa ZHANG Li-ping ZHOU Dao-wei.6-O-Sulfated Modification of Natural Glycoalkaloids Chaconine and Solanine[J].Chemical Research in Chinese University,2006,22(2):189-192. |
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| Authors: | Ji-min ZHAO Sheng-yu LI Yi-fa ZHOU Li-ping ZHANG Dao-wei ZHOU |
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| Institution: | aSchool of Life Sciences, Northeast Normal University, Changchun 130024, P. R. China;bDepartment of Biology, Changchun Normal College, Changchun, 130032, P. R. China |
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| Abstract: | Glycoalkaloids(GAS) have important biological and pharmaceutical activities. In order to study the relationship between the structures and the activities of carbohydrate chains, two natural glycoalkaloids, chaconine( compound 1 )and solanine( compound 2) , were isolated from potato stems and leaves( Solanum tuberosum L. ). The selective sulfation to the 6-hydroxy groups of chaconine and solanine was carried out in a strategy by the use of protective groups.The 6-hydroxyl groups of the sugar chains in chaconine and solanine were protected with 4,4'-dimethoxytrityl(DMT)while the other hydroxyl groups were acetylated. The protective group DMT was removed by using 0. 5% TFA in dichloromethane. The free 6-hydroxyl groups were sulfated by chlorosulfonic acid pyridine to give 6-O-sulfated products. After the acetyl groups were removed, the final products obtained were sulfated chaconine and sulfated solanine. 13C NMR spectra confirmed that chaconine and solanine were sulfated at O6 of the carbohydrate moiety. |
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| Keywords: | Glycoalkaloids Chaconine Solanine Sulfation |
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