School of Pharmaceutical Sciences and Key Laboratory for Applied Technology of Sophisticated Analytical Instruments of Shandong Province, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014, China.
School of Pharmaceutical Sciences and Key Laboratory for Applied Technology of Sophisticated Analytical Instruments of Shandong Province, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250014, China; Department of Chemistry, Karakoram International University, Gilgit 15100, Pakistan.
J Chromatogr A. 2021 Apr 26;1643:462080. doi: 10.1016/j.chroma.2021.462080. Epub 2021 Mar 18.
Acorus tatarinowii Schott is a traditional Chinese medicine used to treat memory and cognitive dysfunction. Because of their efficacy and lower toxic effects, research on α- and β-asarone, the phytoconstituents, has attracted attention owing to their remarkable pharmacological activities. Silver ion coordination complexation high-speed counter-current chromatography was used to separate these isomers from A. tatarinowii extract, coupled with accelerated solvent extraction. Accelerated solvent extraction parameters were investigated with single-factor and orthogonal testing. A two-phase solvent system composed of n-hexane-ethyl acetate-ethanol-water (2:1:2:1, v/v) with 0.50 mol/L silver ions was selected for separation. From 2.0 g crude extract, 1.4 g of β-asarone and 0.09 g of α-asarone were obtained with purities over 98% by sequential sample loading in 20 h. The isolated compounds were identified by electrospray ionization mass spectrometry, H and C NMR. Silver ions significantly increased the separation factor and retention of the stationary phase. The chromatographic behavior indicated that cis-configuration was more strongly complexed with the silver ion. This was further demonstrated with the help of computational analysis. In conclusion, the established method could be employed to separate other cis-trans or E/Z isomers that form coordination complexes.
石菖蒲是一种传统的中药，用于治疗记忆和认知功能障碍。由于其功效和较低的毒性作用，对其植物成分 α-和 β-细辛脑的研究因其显著的药理活性而受到关注。银离子配位高速逆流色谱法结合加速溶剂萃取法，从菖蒲提取物中分离这些异构体。采用单因素和正交试验对加速溶剂萃取参数进行了研究。选择了由正己烷-乙酸乙酯-乙醇-水（2:1:2:1，v/v）组成的两相溶剂系统，并添加 0.50mol/L 的银离子用于分离。从 2.0g 粗提取物中，通过 20 小时的顺序进样，可获得 1.4g 纯度超过 98%的 β-细辛脑和 0.09g 纯度超过 98%的 α-细辛脑。通过电喷雾电离质谱、H 和 C NMR 对分离得到的化合物进行了鉴定。银离子显著增加了固定相的分离因子和保留。色谱行为表明，顺式构型与银离子的络合更强。这一结果得到了计算分析的进一步证实。总之，所建立的方法可用于分离形成配位络合物的其他顺反异构体或 E/Z 异构体。
