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中国胎叶苔中新的贝壳杉烷型倍半萜。

Two new cadinane-type sesquiterpenes from the Chinese liverwort Frullania serrata.

机构信息

a Key Laboratory of Chemical Biology of Ministry of Education, Department of Natural Products Chemistry , School of Pharmaceutical Science, Shandong University , Jinan 250012 , P.R. China.

出版信息

Nat Prod Res. 2014;28(19):1519-24. doi: 10.1080/14786419.2014.909416. Epub 2014 Jun 27.

Abstract

Two new cadinane-type sesquiterpenes, frullanic acid (1) and frullanic acid methyl ester (2), together with four known bibenzyls, brittonin B (3), 3,3'-dimethoxy-4,5-methylenedioxybibenzyl (4), 3,4,5,3',4'-penlamethoxybibenzyl (5) and (±)-3-(4'-methoxybenzyl)-5,6-dimethoxyphtbalide (6), were isolated from the Chinese liverwort Frullania serrata. The structures of the new metabolites were elucidated by analysing the spectroscopic data (1D NMR, 2D NMR, HR-ESI-MS and IR). The absolute configurations of compounds 1 and 2 were determined by comparing the experimental and calculated electronic circular dichroism spectra predicted by using time-dependent density functional theory as well as the CD exciton chirality method.

摘要

从中国苦苣苔科植物 Frullania serrata 中分离得到两个新的卡丹烷型倍半萜,分别为 frullanic 酸(1)和 frullanic 酸甲酯(2),以及四个已知的联苄类化合物,分别为 brittonin B(3)、3,3'-二甲氧基-4,5-亚甲二氧基联苄(4)、3,4,5,3',4'-二甲氧基联苄(5)和(±)-3-(4'-甲氧基苄基)-5,6-二甲氧基邻苯二甲酸二酯(6)。通过分析光谱数据(1D NMR、2D NMR、HR-ESI-MS 和 IR),阐明了新代谢产物的结构。通过比较使用时间相关密度泛函理论预测的实验和计算电子圆二色谱以及 CD 外消旋手性方法,确定了化合物 1 和 2 的绝对构型。

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