Asano N, Kato A, Kizu H, Matsui K, Watson A A, Nash R J
Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa, Japan.
Carbohydr Res. 1996 Oct 31;293(2):195-204. doi: 10.1016/0008-6215(96)00204-2.
GLC-MS analysis has been developed for screening plants of the family Solanaceae for new calystegines. GLC-MS analyses of the extract of Scopolia japonica showed the presence of a new tetrahydroxy-nor-tropane alkaloid in addition to the known calystegines A3, A5, B1, B2, B3, and C1. We gave this new alkaloid the trivial name calystegine B4. The structure of calystegine B4 was determined as 1 alpha, 2 beta, 3 alpha, 4 alpha-tetrahydroxy-nor-tropane from a variety of NMR spectral data. Calystegines B1, B2, and C1 are potent competitive inhibitors with Ki values ranging from 10(-6) to 10(-7) M for almond beta-glucosidase, while calystegine B4 inhibited this enzyme in a competitive manner, with a Ki value of 7.3 microM. Calystegine B2 is also a potent inhibitor of green coffee bean alpha-galactosidase, whereas calystegine B4 exhibited no significant activity for this enzyme. Among rat intestinal glycosidases, only trehalase was potently inhibited by calystegine B4, with an IC50 value of 9.8 microM. Furthermore, calystegine B4 potently inhibited pig kidney trehalase in a competitive manner, with a Ki value of 1.2 microM, but it was almost inactive against yeast and fungal trehalases.
已开发出气相色谱 - 质谱分析法用于筛选茄科植物以寻找新的卡利斯廷。对日本东莨菪提取物的气相色谱 - 质谱分析表明，除了已知的卡利斯廷A3、A5、B1、B2、B3和C1外，还存在一种新的四羟基去甲托烷生物碱。我们给这种新生物碱起了个俗名卡利斯廷B4。根据各种核磁共振光谱数据，确定卡利斯廷B4的结构为1α，2β，3α，4α - 四羟基去甲托烷。卡利斯廷B1、B2和C1是杏仁β - 葡萄糖苷酶的强效竞争性抑制剂，其Ki值范围为10（-6）至10（-7）M，而卡利斯廷B4以竞争性方式抑制该酶，Ki值为7.3 microM。卡利斯廷B2也是生咖啡豆α - 半乳糖苷酶的强效抑制剂，而卡利斯廷B4对该酶无显著活性。在大鼠肠道糖苷酶中，只有海藻糖酶被卡利斯廷B4强烈抑制，IC50值为9.8 microM。此外，卡利斯廷B4以竞争性方式强烈抑制猪肾海藻糖酶，Ki值为1.2 microM，但对酵母和真菌海藻糖酶几乎无活性。
