Chiral resolution and bioactivity of enantiomeric furofuran lignans from Juglans mandshurica Maxim |
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Authors: | Jie Wang Le Zhou Zhuo-Yang Cheng Yu-Xi Wang Zhi-Yang Yan |
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Institution: | 1. School of Traditional Chinese Materia Medica, Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research &2. Development, Liaoning Province, Shenyang Pharmaceutical University, Shenyang, People’s Republic of China |
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Abstract: | AbstractEnantiomers have generally been reported mostly for racemic mixtures with a 1:1 ratio, as in that case there were weak Cotton effects in the ECD spectrum and negligible optical rotations. A furofuran lignan (sesamin), with a remarkable rotation and significant Cotton effects, was isolated from Juglans mandshurica Maxim. Subsequently, sesamin was resolved by chiral HPLC to afford a pair of enantiomers, (+)-sesamin (a) and (?)-sesamin (b), in a ratio of approximately 1:3. Their absolute configurations were determined by computational analysis of their electronic circular dichroism (ECD) spectrum. In addition, the pair of enantiomers were evaluated for the inhibition of self-induced Aβ aggregation. Interestingly, (+)-sesamin (a) (67.7%) and (?)-sesamin (b) (80.6%) exhibited different degrees of anti-Aβ aggregation activity. The different inhibition profiles were further explained by molecular dynamics and docking simulation study. |
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Keywords: | Sesamin furofuran lignans enantiomers chiral resolution Aβ aggregation |
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