柚皮素7-O-葡萄糖苷非对映异构体的NMR波谱分析

发布时间：2018-06-06 18:08

本文选题：核磁共振(NMR) + 柚皮素-O-葡萄糖苷　；参考：《波谱学杂志》2017年04期

【摘要】：二氢黄酮糖苷化后产生的R与S构型非对映异构体在~1H NMR谱上会呈现一些差别,但文献对其差别描述非常有限.为便于利用~1H NMR谱图判断二氢黄酮糖苷的R与S构型非对映异构体,本文首先在植物药皂荚提取物中分离得到一种二氢黄酮苷-柚皮素7-O-葡萄糖苷R与S构型混合物,分析其氘代二甲亚砜(DMSO-d6)溶液的~1H NMR、~(13)C NMR、~1H-~1H COSY、~1H-~(13)C HSQC和~1H-~(13)C HMBC谱,对其~1H和~(13)C NMR谱峰进行了归属;然后,采用手性色谱柱对该混合物进行分离,结合圆二色光谱(CD)技术确定构型;最后,为鉴别R与S构型柚皮素7-O-葡萄糖苷在~1H NMR谱中特征差别谱峰,避免葡萄糖残基质子对二氢黄酮苷元质子化学位移的影响,采集了R与S构型柚皮素7-O-葡萄糖苷及其混合物氘代乙腈(CD_3CN)溶液的NMR谱,结果显示葡萄糖残基端基质子H-1″化学位移差别最为明显,为9.4 Hz;5-位酚羟基质子化学位移差别为5.8 Hz,C环上3个质子化学位移差也较明显.
[Abstract]:There are some differences between R and S enantiomers produced by glycosylation of dihydroflavonoids in 1H NMR spectra, but the difference is very limited in literature. In order to determine the R and S configuration dihydroflavone glycosides enantiomers by 1H NMR spectra, a mixture of dihydroflavone glucoside naringin 7-Oglucoside R and S was isolated from the extract of Gleditsia saponifera. The 1H NMRO ~ (13) C ~ (13) H ~ (-1) H ~ (1) H COSYN ~ (1) H ~ + ~ (13) H ~ (13) C HSQC and ~ (13) H ~ (13) C HMBC spectra of DMSO (DMSO-d6) solution were analyzed, and the peaks of 1H and ~ (13) C NMR spectra were assigned. Then, the mixture was separated by a chiral chromatographic column and determined by circular dichroism spectroscopy (CDCD). In order to identify the characteristic differential peaks of R and S configuration naringin 7-Oglucoside in 1H NMR spectra, to avoid the effect of glucose residue proton on the proton chemical shift of dihydroflavone glycosides. NMR spectra of R and S configuration naringin 7-O- glucoside and its mixture deuterated acetonitrile were collected. The results showed that the chemical shift of the end group proton H-1 "of glucose residue was the most obvious. The proton chemical shift difference of 9.4 HzN 5- phenolic hydroxyl group is 5.8 Hznc ring. The difference of three proton chemical shifts is also obvious.
【作者单位】：湖北大学中药生物技术省重点实验室生物资源绿色转化湖北省协同创新中心;波谱与原子分子物理国家重点实验室武汉磁共振中心(中国科学院武汉物理与数学研究所);
【基金】：国家自然科学基金资助项目(31400304) 波谱与原子分子物理国家重点实验室开放项目(T151203) 中国科学院仪器设备功能开发技术创新项目(YG2012108,YG2012110,YG2011095)
【分类号】：O629;O657.2

【相似文献】