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五叶参中的巨型环烯醚萜糖苷:绵毛马兜铃苦苷 A-E。

Gynostemosides A-E, megastigmane glycosides from Gynostemma pentaphyllum.

机构信息

Department of Natural Products for Chemical Genetic Research, Key Laboratory of Brain Functional Genomics, Ministry of Education, East China Normal University, Shanghai, PR China.

出版信息

Phytochemistry. 2010 Apr;71(5-6):693-700. doi: 10.1016/j.phytochem.2009.12.017. Epub 2010 Jan 25.

DOI:10.1016/j.phytochem.2009.12.017
PMID:20097393
Abstract

Megastigmane glycosides (1-5) together with seven (6-12) related known compounds were isolated from the whole plants of Gynostemma pentaphyllum. The structures were elucidated by means of spectroscopic methods, including 2D NMR, HR-ESIMS, and circular dichroism (CD), as well as chemical transformations to be (3R,4R,5S,6S,7E)-3,4,6-trihydroxymegastigmane-7-en-9-one-3-O-beta-D-glucopyranoside (gynostemoside A, 1), (3S,4S,5R,6R,7E,9R)-3,4,6,9-tetrahydroxymegastigmane-7-en-3-O-beta-D-glucopyranoside (gynostemoside B, 2), (3S,4S,5S,6S,7E,9R)-3,4,9-trihydroxymegastigmane-7-en-9-O-beta-D-glucopyranoside (gynostemoside C, 3), (3S,4S,5S,6S,7E,9R)-3,4,9-trihydroxymegastigmane-7-en-3-O-beta-D-glucopyranoside (gynostemoside D, 4), and (3S,4S,5S,6S,7E,9R)-3,4,9-trihydroxymegastigmane-7-en-4-O-beta-D-glucopyranoside (gynostemoside E, 5), respectively.

摘要

从绞股蓝全草中分离得到了 5 个新的 megastigmane 糖苷(1-5)和 7 个相关的已知化合物。通过光谱方法,包括 2D NMR、HR-ESIMS 和圆二色性(CD),以及化学转化,确定了它们的结构,分别为(3R,4R,5S,6S,7E)-3,4,6-三羟基 megastigmane-7-烯-9-酮-3-O-β-D-吡喃葡萄糖苷(绞股蓝皂苷 A,1)、(3S,4S,5R,6R,7E,9R)-3,4,6,9-四羟基 megastigmane-7-烯-3-O-β-D-吡喃葡萄糖苷(绞股蓝皂苷 B,2)、(3S,4S,5S,6S,7E,9R)-3,4,9-三羟基 megastigmane-7-烯-9-O-β-D-吡喃葡萄糖苷(绞股蓝皂苷 C,3)、(3S,4S,5S,6S,7E,9R)-3,4,9-三羟基 megastigmane-7-烯-3-O-β-D-吡喃葡萄糖苷(绞股蓝皂苷 D,4)和(3S,4S,5S,6S,7E,9R)-3,4,9-三羟基 megastigmane-7-烯-4-O-β-D-吡喃葡萄糖苷(绞股蓝皂苷 E,5)。

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