A new resin glycoside from Calystegia soldanella and its antiviral activity towards herpes

A new resin glycoside from Calystegia soldanella and its antiviral activity towards herpes
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DOI:
10.1080/14786419.2017.1280492
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发表时间:
2017-01-01
影响因子:
2.2
通讯作者:
Nohara, Toshihiro
Nohara, Toshihiro
中科院分区:
化学3区
文献类型:
--
作者:
Ono, Masateru;Kanemaru, Yukiyo;Nohara, Toshihiro

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从Calystegia sellanella Roem的叶、茎和根中分离得到一种新的树脂糖苷,命名为Calysolin XVIII (1)。等舒尔特。 (旋花科)。 1的结构定义为11S-墨西哥芥酸11-O-β-D-吡喃葡萄糖基-(1 -> 3)-O-(2-O-2S-甲基丁酰基,4-O-3-羟基-2-亚甲基丁酰基)-α-1-吡喃鼠李糖基-(1 -> 2)-[O-β-D-吡喃葡萄糖基-(1 -> 6)-O-(34-二-O-2S-甲基丁酰)-β-D-吡喃葡萄糖基-(1 -> 3)]-O-β-D-吡喃葡萄糖基-(1 -> 2)-β-D-吡喃喹啉,分子内1,2 ''''''-酯,基于光谱数据。化合物 1 是第一个已知的以 3-羟基-2-亚甲基丁酸为有机酸成分的树脂糖苷。此外,1 对 1 型单纯疱疹病毒具有抗病毒活性,IC50 值为 2.3 mu M。[图表]。
A new resin glycoside, named calysolin XVIII (1), was isolated from the leaves, stems and roots of Calystegia soldanella Roem. et Schult. (Convolvulaceae). The structure of 1 was defined as 11S-jalapinolic acid 11-O-beta-D-glucopyranosyl-(1 -> 3)-O-(2-O-2S-methylbutyryl, 4-O-3-hydroxy-2-methylenebutyryl)-alpha-l-rhamnopyranosyl-(1 -> 2)-[O-beta-D-glucopyranosyl-(1 -> 6)-O-(34-di-O-2S-methylbutyryl)-beta-D-glucopyranosyl-(1 -> 3)]-O-beta-D-glucopyranosyl-(1 -> 2)-beta-D-quinovopyranoside, intramolecular 1,2 ''''''-ester on the basis of spectroscopic data. Compound 1 is the first known resin glycoside to feature 3-hydroxy-2-methylenebutyric acid as a component organic acid. In addition, 1 demonstrated an antiviral activity against herpes simplex virus type 1, with an IC50 value 2.3 mu M.[GRAPHICS].