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烷基没食子酸酯及其与β-环糊精包合物从β-环糊精包合物中释放的控制特性。

Controlled release characteristics of alkyl gallates and gallic acid from β-cyclodextrin inclusion complexes of alkyl gallates.

机构信息

SKL of Marine Food Processing & Safety Control, National Engineering Research Center of Seafood, Collaborative Innovation Center of Seafood Deep Processing, Liaoning Province Key Laboratory for Marine Food Science and Technology, School of Food Science and Technology, Dalian Polytechnic University, Dalian 116034, People's Republic of China.

School of Food and Biological Engineering, Hefei University of Technology, Hefei 230601, People's Republic of China.

出版信息

Food Chem. 2024 Dec 1;460(Pt 3):140726. doi: 10.1016/j.foodchem.2024.140726. Epub 2024 Aug 2.

DOI:10.1016/j.foodchem.2024.140726
PMID:39111044
Abstract

The freeze-drying approach was used to create inclusion complexes utilizing alkyl gallates and β-cyclodextrin, namely dodecyl gallate, octyl gallate, butyl gallate, and ethyl gallate, which are exemplary examples of phenolic esters. The everted-rat-gut-sac model demonstrated that the inclusion complexes released alkyl gallates, which were subsequently hydrolyzed to generate free gallic acid, as evidenced by HPLC-UV analysis. Both gallic acid and short-chain alkyl gallates were capable of permeating the small intestinal membrane. The transport rate of gallic acid (or alkyl gallates) exhibited an initial rise followed by a drop when the carbon-chain lengths varied. The inclusion complex groups exhibited a superior sustained-release effect compared to the comparable alkyl gallates groups, thus possibly leading to higher bioavailability and stronger bioactivity. Moreover, altering the length of the carbon chain will allow for the effortless achievement of regulated release of phenolic compounds and short-chain phenolic esters from such β-cyclodextrin inclusion complexes.

摘要

采用冷冻干燥法制备了包含物复合物,利用烷基没食子酸盐和β-环糊精,即没食子酸十二酯、没食子酸辛酯、没食子酸丁酯和没食子酸乙酯,它们是酚酯的典型例子。外翻鼠肠囊模型表明,包含物复合物释放出烷基没食子酸盐,随后通过 HPLC-UV 分析证实其发生水解生成游离没食子酸。游离没食子酸和短链烷基没食子酸盐均可穿透小肠膜。当碳链长度变化时,没食子酸(或烷基没食子酸盐)的转运速率表现为先上升后下降的趋势。包含物复合物组表现出优于可比的烷基没食子酸盐组的持续释放效果,因此可能导致更高的生物利用度和更强的生物活性。此外,改变碳链的长度可以轻松实现从这种β-环糊精包含物复合物中调节释放酚类化合物和短链酚酯。

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