辣椒碱与β-环糊精包合物的核磁共振研究

波谱学杂志

辣椒碱与β-环糊精包合物的核磁共振研究

赵兵1,2，李艺蕾1，李明1，刘宏民1,2*

1. 郑州大学药学院，河南郑州 450001; 2. 新药研发中心，河南郑州 450001

收稿日期:2013-04-28 修回日期:2013-06-19 出版日期:2013-12-05 发布日期:2013-12-05
作者简介:赵兵（1985-），男，河南商丘人，硕士，讲师，研究方向为药物合成与波谱解析.电话：0371-67739015, E-mail：zhaobing@zzu.edu.cn.*通讯联系人：刘宏民，电话：0371-67781739，E-mail：liuhm@zzu.edu.cn.
基金资助:
国家自然科学基金资助项目(81172937).

An NMR Study of Capsaicin/β-cyclodextrin Complex

ZHAO Bing1,2，LI Yi-lei1，LI Ming1，LIU Hong-min1,2*

1. School of Pharmaceutical Science, Zhengzhou University, Zhengzhou 450001, China;
2. Center for Drug Research and Development, Zhengzhou 450001, China

Received:2013-04-28 Revised:2013-06-19 Online:2013-12-05 Published:2013-12-05
About author:*Corresponding author: Liu Hong-min, Tel: 0371-67781739, E-mail: liuhm@zzu.edu.cn.
Supported by:
国家自然科学基金资助项目(81172937).

摘要/Abstract

摘要：

利用核磁共振方法研究了辣椒碱β-环糊精包合物的化学计量比、空间结构信息及其在水溶液中的自扩散系数. 通过测定不同浓度比的辣椒碱和β-环糊精混合溶液的 ¹H NMR数据，绘制Job's曲线，辣椒碱和β-环糊精的Job's曲线均在r=0.5处出现拐点. 同时测定了该包合物的2D ROESY和DOSY谱图，ROESY谱图中NOE交叉信号出现在辣椒碱的H-1~H-8和β-环糊精的H-3′、H-5′、H-6′之间，DOSY测得β-环糊精和辣椒碱形成包合物前后的表观自扩散系数. 结果表明，辣椒碱β-环糊精包合物的主客体分子的化学计量比为1∶1，辣椒碱分子的异丙基端从β-环糊精的宽口端进入疏水腔，其中H-1~H-8部分在空腔内部，包合物的自扩散系数为2.95×10^-10m²/s.

关键词: 核磁共振（NMR）, 辣椒碱, β-环糊精, 包合作用, ROESY, DOSY

Abstract:

NMR spectroscopy was used to investigate the stoichiometry, three-dimensional geometry and formation constant of capsaicin and β-cyclodextrin complex. Capsaicin/β-cyclodextrin solutions with different concentration ratio were measured. Inflection point on Job's curve measured by ¹H NMR appeared at r=0.5. Two-dimensional ROESY and DOSY spectra of the complexes were obtained. Cross peaks in the ROESY spectra appeared between capsaicin H-1 to H-8 and β-cyclodextrin H-3′, H-5′, H-6′. Apparent diffusion coefficients of protons in cyclodextrin and capsaicin were measured with DOSY. The results showed that the stoichiometry of the capsaicin complex was 1∶1 and the isopropyl side of capsaicin entered into the hydrophobic cavity of β-cyclodextrin from the wider rim while H-1 to H-8 of capsaicin were included into the hydrophobic cavity completely. The diffusion coefficient of complex was 2.95×10^-10m²/s.

Key words: NMR, capsaicin, β-cyclodextrin, inclusion effect, ROESY, DOSY

中图分类号:

O482.53

赵兵1,2，李艺蕾1，李明1，刘宏民1,2*. 辣椒碱与β-环糊精包合物的核磁共振研究[J]. 波谱学杂志.

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