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第 36 卷第 6 期 精 细 化 工 Vol.36, No.6
201 9 年 6 月 FINE CHEMICALS June 2019

医药与日化原料
4-甲基-7-羟基香豆素及其衍生物的抗氧化性能

*
席高磊，许克静，王宏伟，杨金初，蔡莉莉，陈泽少，杜 佳，陈芝飞
（河南中烟工业有限责任公司技术中心，河南 郑州 450000）

摘要：以间苯二酚和乙酰乙酸乙酯为原料，合成了 4-甲基-7-羟基香豆素（Ⅰ），再经酯化得到 4-甲基-7-乙酰氧
2+
基香豆素（Ⅱ）；采用 2,2-偶氮二异丁基脒二盐酸盐（AAPH）、HO•、Cu /还原型谷胱甘肽（GSH）自由基氧
化 DNA 的反应体系对化合物的抗氧化活性进行了测试；通过淬灭 2,2-偶氮-双-(3-乙基苯并噻唑啉-6-磺酸)二铵
盐自由基（ABTS+•）、二苯苦味酰肼自由基（DPPH•）、2,6-二叔丁基-(3,5-二叔丁基-4-氧代-2,5-环己二烯)-对-甲
苯氧（galvinoxyl）自由基体系探索了化合物还原自由基的能力，进而探究了羟基对香豆素抗氧化性能的影响。
结果表明：在抑制 AAPH 引发的 DNA 氧化反应体系中，每个化合物Ⅰ能够捕获 1.61 个自由基，而化合物Ⅱ不
能捕获自由基；在抑制 HO•和 GS•引发的 DNA 氧化反应体系中，化合物Ⅰ相对空白硫代巴比妥酸活性物质
（TBARS）吸光度分别为 76.5%和 64.1%，化合物Ⅱ相对空白 TBARS 吸光度分别为 87.1%和 81.7%；化合物Ⅰ
能够捕获 ABTS+•、DPPH•、galvinoxyl 自由基，而化合物Ⅱ仅能够捕获 ABTS+•和 DPPH•两种自由基；化合物
Ⅰ抑制自由基引发的 DNA 氧化反应活性和捕获自由基能力均优于化合物Ⅱ，是一种潜在的抗氧化剂。
关键词：4-甲基-7-羟基香豆素；4-甲基-7-乙酰氧基香豆素；抗氧化；医药与日化原料
中图分类号：R914.5 文献标识码：A 文章编号：1003-5214 (2019) 06-1159-08

Antioxidant Properties of 4-Methyl-7-hydroxycoumarin and Derivative

XI Gao-lei, XU Ke-jing, WANG Hong-wei, YANG Jin-chu,
*
CAI Li-li, CHEN Ze-shao, DU Jia, CHEN Zhi-fei
（Technology Center for China Tobacco Henan Industrial Limited Company, Zhengzhou 450000, Henan, China）

Abstract: 4-Methyl-7-hydroxycoumarin was prepared by the reaction of the resorcinol with ethyl
acetoacetate and then 4-methyl-7-acetoxylcoumarin ( Ⅰ ) was obtained by the esterification of
4-methyl-7-hydroxycoumarin (Ⅱ). Antioxidant abilities of the obtained compounds were evaluated by
2+
inhibiting 2,2-azobis(2-amidinopropanehydrochloride) (AAPH)-, Cu /glutathione (GSH)-, and HO•-
induced oxidation of DNA. The radical-scavenging properties of the obtained compounds were estimated
by quenching 2,2-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+•), 2,2-diphenyl-
1-picrylhydrazyl (DPPH•), and galvinoxyl radicals, and then the structure activity relationship of these
compounds could be explored. The results showed: compound Ⅰ can scavenge 1.61 radicals in AAPH-
induced oxidation of DNA, but compound Ⅱ can not scavenge radicals. The TBARS percentage of
compound Ⅰ and Ⅱ were 76.5% and 87.1% in inhibiting HO•-induced oxidation of DNA, respectively.
The TBARS percentage of compound Ⅰ and Ⅱ were 64.1% and 81.7% in inhibiting GS•-induced
oxidation of DNA, respectively. Compound Ⅰ can scavenge ABTS+•, DPPH•, and galvinoxyl radical, but
compound Ⅱ can only scavenge ABTS+• and DPPH• radicals. Compound Ⅰ had antioxidant property,
while antioxidant property was reduced when hydroxyl was protected, and it can be a potential antioxidant.
Key words: 4-methyl-7-hydroxycoumarin; 4-methyl-7-acetoxylcoumarin; antioxidant; drug and cosmetic
materials

[1]
自由基引发的氧化损伤是导致衰老及多种疾病 的直接原因 ，及时清除多余自由基是预防衰老和

收稿日期：2018-09-27; 定用日期：2019-01-23; DOI: 10.13550/j.jxhg.20180722
作者简介：席高磊（1987—），男，博士，工程师，E-mail：xigaoleijida@126.com。联系人：陈芝飞（1979—），男，副研究员，E-mail：
chenzhifei@126.com。