表儿茶素的碳酰化改性及其紫外吸收和抗氧化活性

doi:10.13305/j.cnki.jts.2024.03.002

茶叶科学 ›› 2024, Vol. 44 ›› Issue (3): 493-500.doi: 10.13305/j.cnki.jts.2024.03.002

表儿茶素的碳酰化改性及其紫外吸收和抗氧化活性

雷响^1,2, 张闽峰¹, 林辉¹, 王丽丽¹, 郑德勇^1,3,*

1.福建农林大学材料工程学院,福建福州 350002;
2.福建理工大学法学院,福建福州 350118;
3.植物纤维功能材料国家林业和草原局重点实验室,福建福州 350002

收稿日期:2023-12-08 修回日期:2024-04-25 出版日期:2024-06-15 发布日期:2024-07-08
通讯作者: *ffczdy@163.com
作者简介:雷响,男,硕士研究生,主要从事精细化学品合成方面的研究,spxykcblx@163.com。
基金资助:
中央财政林业科技推广示范项目（闽[2019]TG17号）、福建省“2011协同创新中心”中国乌龙茶产业协同创新中心专项（闽教科[2015]75号）

Carbonylation Modification of Epicatechin and Its Activities of UV Absorption and Antioxidant

LEI Xiang^1,2, ZHANG Minfeng¹, LIN Hui¹, WANG Lili¹, ZHENG Deyong^1,3,*

1. College of Material Engineering, Fujian Agriculture and Forestry University, Fuzhou 350002, China;
2. Law School, Fujian University of Technology, Fuzhou 350118, China;
3. National Forestry and Grassland Administration Key Laboratory of Plant Fiber Functional Materials, Fuzhou 350002, China

Received:2023-12-08 Revised:2024-04-25 Online:2024-06-15 Published:2024-07-08

摘要/Abstract

摘要： 为增强表儿茶素衍生物的紫外吸收性能、改善其在油脂等非极性溶剂中的溶解度,以甲烷磺酸为溶剂和催化剂,由表儿茶素和对羟基苯甲酸合成了2,2'-二(对羟基苯甲酮基)-表儿茶素,经柱层析分离得到目标产物,采用高效液相色谱（HPLC）验证纯度,运用紫外-可见光（UV-vis）光谱、傅里叶变换红外（FT-IR）光谱、液相色谱-质谱联用（LC-MS）和核磁共振（NMR）波谱等表征手段确证目标产物结构。评价了2,2'-二(对羟基苯甲酮基)-表儿茶素的紫外吸收性能,以及对2,2-联氮-二(3-乙基苯并噻唑-6-磺酸)二铵盐阳离子自由基、1,1-二苯基-2-三硝基苯肼自由基和超氧阴离子自由基清除能力。结果表明,合成的2,2'-二(对羟基苯甲酮基)-表儿茶素与常用紫外线吸收剂4-甲氧基肉桂酸-2-乙基己酯（OMC）具有相似的紫外吸收范围和相当的摩尔吸光系数,有望成为一种性能优良的UVB波段紫外线吸收剂;2,2'-二(对羟基苯甲酮基)-表儿茶素具有良好的体外抗氧化活性,其体外抗氧化能力高于维生素C（VC）、略低于表儿茶素,有望应用于化妆品领域。

关键词: 表儿茶素, 碳酰化, 改性, 紫外吸收, 化妆品

Abstract: In order to enhance the UV absorption characteristic of epicatechin derivatives and improve their solubility in non-polar solvents such as oils and fats, 2,2'-di(p-hydroxybenzocarbonyl)-epicatechin was synthesized from epicatechin and p-hydroxybenzoic acid using methane sulfonic acid as solvent and catalyst. The target products were separated by column chromatography, and the purity was verified by high performance liquid chromatography (HPLC), and the structure of the target products were verified by UV-vis, FT-IR, ¹H NMR, ¹³C NMR, LC-MS spectroscopy. The UV absorption characteristic of 2,2'-di(p-hydroxybenzocarbonyl)-epicatechin and its ability to scavenge ABTS⁺·, DPPH· and O^2-· were evaluated. The results show that the synthesized 2,2'-di(p-hydroxybenzocarbonyl)-epicatechin had similar UV absorption and comparable molar absorptivity to OMC, the commonly used UV absorber, and is expected to be an excellent UV absorber in the UVB band. 2,2'-di(p-hydroxybenzocarbonyl)-epicatechin had good antioxidant activity in vitro, and its antioxidant capacity in vitro was higher than that of VC and slightly lower than that of epicatechin, which is expected to be used for cosmetic applications.

Key words: epicatechin, carbonylation, modification, UV absorption, cosmetic

中图分类号:

雷响, 张闽峰, 林辉, 王丽丽, 郑德勇. 表儿茶素的碳酰化改性及其紫外吸收和抗氧化活性[J]. 茶叶科学, 2024, 44(3): 493-500. doi: 10.13305/j.cnki.jts.2024.03.002.

LEI Xiang, ZHANG Minfeng, LIN Hui, WANG Lili, ZHENG Deyong. Carbonylation Modification of Epicatechin and Its Activities of UV Absorption and Antioxidant[J]. Journal of Tea Science, 2024, 44(3): 493-500. doi: 10.13305/j.cnki.jts.2024.03.002.

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表儿茶素的碳酰化改性及其紫外吸收和抗氧化活性

Carbonylation Modification of Epicatechin and Its Activities of UV Absorption and Antioxidant

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