沈阳药科大学学报

2012, v.29;No.197(06) 462-466

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~1H-NMR法测定辽宁紫草中紫草素对映体纯度
Determination of enantiomeric excess of shikonin isolated from Lithospermum erythrorhizon Sieb. et Zucc. using ~1H-NMR

丁静,张敏,李绍顺,周文
DING Jing,ZHANG Min,LI Shao-shun,ZHOU Wen(School of Pharmacy

摘要(Abstract):

目的研究辽宁紫草(Lithospermum erythrorhizon Sieb.et Zucc.)中紫草素对映体纯度。方法在辽宁紫草素侧链上引入S(-)-α-甲氧基-α-(三氟甲基)-苯乙酸形成Mosher酯,并运用1H-NMR测定后者H-1'化学位移的非等价性所产生的峰值相对强度,从而确定辽宁紫草中紫草素对映体纯度。结果辽宁紫草中紫草素对映体过量为72.5%。结论利用天然紫草制备的紫草素可能是紫草素与其对映体阿卡宁不同程度的光学混合物。
Objective To determine enantiomeric excess(e.e.)of shikonin isolated from the roots of Lithospermum erythrorhizon Sieb.et Zucc.Methods Mosher ester was prepared through the introduction of S-(-)-α-methoxy-α-(trifluoromethyl)-phenylacetic acid to hydroxyl group in the side chain of shikonin isolated from the Liaoning gromwell,and then 1H-NMR was used to determine the relative intensity of the resulting peak of H-1′as a result of chemical shift non-equivalence,thereby the e.e.of shikonin was acquired.Results The e.e.value of shikonin from this boraginaceae plant was 72.5%.Conclusions Shikonin isolated from the roots of the boraginaceae probably consists of shikonin and its antipode alkannin with varying degrees.

关键词(KeyWords): 核磁共振氢谱;Mosher酯;对映体纯度;紫草素;辽宁紫草
1H-NMR;Mosher ester;enantiomeric excess;shikonin;Lithospermum erythrorhizon Sieb.et Zucc.

Abstract:

Keywords:

基金项目(Foundation): 上海市自然科学基金资助项目(11ZR1416300);; 博士点新教师基金资助项目(20100071120053);; 第四期国家大学生创新性实验计划资助项目(IPP001002)

作者(Author): 丁静,张敏,李绍顺,周文
DING Jing,ZHANG Min,LI Shao-shun,ZHOU Wen(School of Pharmacy

DOI: 10.14066/j.cnki.cn21-1349/r.2012.06.004

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