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一对具有前所未有骨架的对映二聚体来自紫丁香茎皮。

A pair of enantiomeric dimers with an unprecedented skeleton from stem barks of Syringa pinnatifolia.

机构信息

Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing 100029, People's Republic of China; Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, People's Republic of China.

Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing 100029, People's Republic of China.

出版信息

Fitoterapia. 2022 Apr;158:105173. doi: 10.1016/j.fitote.2022.105173. Epub 2022 Mar 12.

DOI:10.1016/j.fitote.2022.105173
PMID:35288210
Abstract

A pair of enantiomers with a rearranged dimeric phenylethanol skeleton, namely (±)-disyringol A (1a and 1b), were isolated from the stem barks of Syringa pinnatifolia. The structures were established using IR, UV, MS, and NMR data, and their absolute configurations were resolved by experimental and calculated ECD data analysis. Their biosynthetic pathway was speculated on the basis of a phenylethanoid precursor and was proved by a total synthesis. Compounds 1a and 1b showed the inhibition against NO production in LPS-induced RAW264.7 cells with their IC values of 27.28 and 24.64 μM, respectively, however no protective effect was observed against the hypoxia-induced injuries to H9c2 cells.

摘要

一对具有重排二聚苯乙醇骨架的对映异构体,即(±)-disyringol A(1a 和 1b),从丁香的茎皮中分离得到。结构通过 IR、UV、MS 和 NMR 数据确定,其绝对构型通过实验和计算 ECD 数据分析确定。基于苯乙醇前体推测了它们的生物合成途径,并通过全合成得到证实。化合物 1a 和 1b 对 LPS 诱导的 RAW264.7 细胞中 NO 产生的抑制作用,其 IC50 值分别为 27.28 和 24.64 μM,但对 H9c2 细胞缺氧损伤没有保护作用。

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