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Lignans and neolignans with isovaleroyloxy moiety from Solanum lyratum Thunb.: Chiral resolution, configurational assignment and neuroprotective effects
Phytochemistry ( IF 3.2 ) Pub Date : 2020-10-01 , DOI: 10.1016/j.phytochem.2020.112461
Shuang-Shuang Li 1 , Zi-Lin Hou 1 , Guo-Dong Yao 1 , Rui Guo 1 , Yu-Xi Wang 1 , Bin Lin 2 , Xiao-Xiao Huang 1 , Shao-Jiang Song 1
Affiliation  

Eight pairs of enantiomeric lignans and neolignans including thirteen undescribed compounds, along with an undescribed meso compound, were isolated from the herbs of Solanum lyratum Thunb.(Solanaceae). Their structures and relative configurations were determined by extensive spectroscopic analyses of HRESIMS and nuclear magnetic resonance. The absolute configurations of the pure isomers were established based on the cooperative comparison between the experimental and calculated electronic circular dichroism (ECD) and optical rotation (OR). It is interesting that we obtained several naturally occurring stereoisomers with the identical gross structure possessing several stereogenic carbons from S. lyratum. Additionally, all isolates were assessed for neuroprotective effects toward human neuroblastoma SH-SY5Y cells injury induced by H2O2.

中文翻译:

来自 Solanum lyratum Thunb. 的具有异戊酰氧基部分的木脂素和新木脂素:手性分辨率、构型分配和神经保护作用

从 Solanum lyratum Thunb. (Solanaceae) 的草本植物中分离出八对对映体木脂素和新木脂素,包括 13 种未描述的化合物以及一种未描述的内消旋化合物。它们的结构和相对构型是通过 HRESIMS 和核磁共振的广泛光谱分析确定的。纯异构体的绝对构型是基于实验和计算的电子圆二色性 (ECD) 和旋光度 (OR) 之间的协作比较而建立的。有趣的是,我们从 S. lyratum 中获得了几种具有相同总体结构的天然存在的立体异构体,这些立体异构体具有几个立体碳。此外,还评估了所有分离株对 H2O2 诱导的人神经母细胞瘤 SH-SY5Y 细胞损伤的神经保护作用。
更新日期:2020-10-01
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