[1]滕巧巧,朱信辉,华 佳,等.脂溶性小檗碱衍生物的合成及其表观油水分配系数测定[J].常州大学学报(自然科学版),2019,31(06):23-30.
　TENG Qiaoqiao,ZHU Xinhui,HUA Jia,et al.Synthesis of Lipophilic Berberine Derivatives and Determination of Their Apparent Oil/Water Partition Coefficient[J].Journal of Changzhou University(Natural Science Edition),2019,31(06):23-30.
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脂溶性小檗碱衍生物的合成及其表观油水分配系数测定()
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常州大学学报(自然科学版)[ISSN:2095-0411/CN:32-1822/N]

卷:
第31卷
期数:
2019年06期
页码:
23-30
栏目:
化学化工
出版日期:
2019-11-28

文章信息/Info

Title:
Synthesis of Lipophilic Berberine Derivatives and Determination of Their Apparent Oil/Water Partition Coefficient
文章编号:
2095-0411(2019)06-0023-08
作者:
滕巧巧; 朱信辉; 华 佳; 蒋卫华; 孟 启
(常州大学 石油化工学院,江苏 常州 213164)
Author(s):
TENG Qiaoqiao;  ZHU Xinhui;  HUA Jia;  JIANG Weihua;  MENG Qi
(School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China)
关键词:
小檗碱;  表观油水分配系数;  合成;  脂溶性
Keywords:
berberine;  apparent oil-water partition coefficient;  synthesis;  lipophilic
分类号:
O 629.3
文献标志码:
A
摘要:
以3/4-羟基取代苯甲醛为初始原料,经烷基化、醛胺缩合、还原、环合等步骤分别合成了9-甲氧基-10-烷氧基取代(6f—6h)和10-甲氧基-11-烷氧基取代小檗碱衍生物(5a—5e),其中(5c—5e)为新化合物,结构和纯度经熔点,1H NMR,13C NMR,ESI-MS多重表征确认。采用摇瓶法,结合紫外分光光度法考察了两类衍生物在正辛醇-水体系中的表观油水分配系数(logP),结果显示引入长碳链使得小檗碱衍生物的脂溶性普遍性增强。当碳链长度为12时,油水分配系数增幅最大,由-0.62分别增至1.04(5e)和1.40(6h),将更利于肠道吸收。
Abstract:
Using 3/4-hydroxybenzaldehyde as the initial raw material, the 9-methoxy-10-alkoxy-(6f—6h)and 10-methoxy-11-alkoxy substituted berberines(5a—5e)were synthesized by successive alkylation, condensation, reduction and cyclization, etc. New compounds 5c—5e were characterized by 1H NMR, 13C NMR, ESI-MS and melting point analysis. The apparent oil/water distribution coefficient(logP)of these two types of derivatives in n-octanol/aqueous system was investigated by using Shaker method combined with ultraviolet spectrophotometry. The results showed that introducing carbon long chains at the C10 and C11 positions is effective in enhancing the lipophilicity of berberines. Among the long chains, the C12H25 substituents always lead to the maximum increase of the log P values from -0.62(berberine)to 1.04(5e)and 1.40(6h), respectively. They will thus be better for intestinal absorption.

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备注/Memo

备注/Memo:
收稿日期:2019-04-11。
作者简介:滕巧巧(1988—),女,浙江温州人,博士,讲师。通信联系人:孟启(1965—),E-mail: mengqi@cczu.edu.cn
更新日期/Last Update: 2019-12-02