Diastereomeric identification of neolignan rhamnosides from Trochodendron aralioides leaves by LC-SPE-NMR and circular dichroism

被引:5
作者
Chang, Chia-Chuan [1 ]
Tsai, Wen-Tsai [1 ]
Chen, Chien-Kuang [1 ]
Chen, Chung-Hsiung [1 ]
Lee, Shoei-Sheng [1 ]
机构
[1] Natl Taiwan Univ, Sch Pharm, Taipei 10050, Taiwan
关键词
Trochodendron aralioides; Neolignan; Oxyneolignan; HPLC-SPE-NMR; CONSTITUENTS; GLYCOSIDES; LIGNANS; WOOD;
D O I
10.1016/j.fitote.2019.104455
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Trochodendron aralioides is an old-existing relic plant with limited availability and only a few identified compounds. Accumulative analysis on the methanolic extract from its leaf part by LC-SPE-NMR resulted in the identification of seven new compounds, including three neolignan alpha-rhamnosides [(7R,8S)-dihydrodehydrodiconiferyl alcohol- 9-O-alpha-rhamnopyranoside (2) and 9'-O-alpha-rhamnopyranoside (3), and (7S,8R)-dehydrodiconiferyl alcohol 9'-O-alpha-rhamnopyranoside (4)], two isomeric oxyneolignan alpha-rhamnosides [(7R,8S)- (5) and (7R,8R)-icariside E-8 (6)), and (7R,8S)- (10) and (7R,8R)-icariside E-9 (11)], and two isomeric acylated fructofuranosyl mevalonolactones (13, 14), along with five known compounds (1, 7-9 and 12). The absolute configuration of the C-7 and C-8 positions for the new compounds 2-6 and 10-11 was assigned by comparison of the reported ECD spectra. Compounds 2, 3, 4, and 6 were further isolated by semi-preparative column chromatography for structure confirmation by 2D NMR spectroscopic analysis.
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页数:7
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