阿魏酰氨基酸乙酯的合成及其抗氧化活性研究

doi:10.3969/j.issn.1001-1803.2020.09.008

日用化学工业 ›› 2020, Vol. 50 ›› Issue (9): 624-628.doi: 10.3969/j.issn.1001-1803.2020.09.008

阿魏酰氨基酸乙酯的合成及其抗氧化活性研究

郭晓丹(),宋京九,祝钧()

北京工商大学理学院,北京 100048

收稿日期:2019-10-23 修回日期:2020-08-30 出版日期:2020-09-22 发布日期:2020-09-23
通讯作者: 祝钧
作者简介:郭晓丹（1993-）,女,满族,河北承德人,硕士研究生,电话：15313937435,E-mail： 18232466472@163.com。
基金资助:
北京市高等学校教学名师支持项目(19005753005);2019年研究生科研项目提升计划

Synthesis and anti-oxidant activity of feruloylamino acid ethyl ester

GUO Xiao-dan(),SONG Jing-jiu,ZHU Jun()

School of Science, Beijing Technology and Business University, Beijing 100048, China

Received:2019-10-23 Revised:2020-08-30 Online:2020-09-22 Published:2020-09-23
Contact: Jun ZHU

摘要/Abstract

摘要：

以阿魏酸和氨基酸乙酯盐酸盐为原料,1-（3-二甲基氨基丙基）-3-乙基碳二亚胺盐酸盐（EDC·HCl）和1-羟基苯并三唑（HOBt）为催化剂,采用EDC缩合法合成阿魏酰蛋氨酸乙酯（Ⅰ）、阿魏酰异亮氨酸乙酯（Ⅱ）、阿魏酰苏氨酸乙酯（Ⅲ）和阿魏酰苯丙氨酸乙酯（Ⅳ）。利用核磁共振氢谱（ ¹H NMR）和高效液相色谱-质谱（HPLC-MS）对产物结构进行表征,并且比较了阿魏酰氨基酸乙酯和阿魏酸在清除DPPH自由基和ABTS自由基方面的活性。结果表明：合成的4种阿魏酰氨基酸乙酯能够较好的清除自由基,且清除率均大于阿魏酸单体;阿魏酰苯丙氨酸乙酯（Ⅳ）清除DPPH自由基和ABTS自由基能力最强,IC₅₀分别为37.567和1.689 μmol/L。红细胞溶血实验表明：合成的阿魏酰氨基酸衍生物Ⅰ、Ⅲ、Ⅳ的刺激性均小于阿魏酸。

关键词: 阿魏酸, 阿魏酰氨基酸酯衍生物, DPPH自由基, ABTS自由基, 化妆品添加剂

Abstract:

Ferulic methionine ethyl ester （Ⅰ）, feruli isoleucine ethyl ester （Ⅱ）, feruli threonine ethyl ester （Ⅲ） and feruli phenylalanine ethyl ester （Ⅳ） were synthesized by EDC condensation using ferulic acid and amino acid ethyl ester hydrochloride as raw materials, and 1-（3-dimethylaminopropyl）-3-ethylcarbodiimide hydrochloride （EDC·HCl） and 1-hydroxybenzotriazole （HOBt） as catalysts. The structure of the products was characterized by ¹H NMR and HPLC-MS, and the activities of ferulic acid and ethyl ferulic acid in scavenging DPPH and ABTS free radicals were compared. The results show that the four kinds of ferulic acid ethyl ester scavenged free radicals better, and the scavenging rates are higher than that of ferulic acid monomer. The ferryl phenylalanine ethyl ester （Ⅳ） has the strongest ability to scavenge DPPH free radicals and ABTS free radicals, with IC₅₀ of 37.567 and 1.689 μmol/L, respectively. The red blood cells hemolysis test show that the irritation of the synthesized derivatives of ferulic acid Ⅰ, Ⅲ and Ⅳ is less than that of ferulic acid.

Key words: ferulic acid, ferulic acid ester derivative, DPPH radical, ABTS radical, additives of cosmetics

中图分类号:

TQ658

郭晓丹,宋京九,祝钧. 阿魏酰氨基酸乙酯的合成及其抗氧化活性研究[J]. 日用化学工业, 2020, 50(9): 624-628.

GUO Xiao-dan,SONG Jing-jiu,ZHU Jun. Synthesis and anti-oxidant activity of feruloylamino acid ethyl ester[J]. China Surfactant Detergent & Cosmetics, 2020, 50(9): 624-628.

图/表 3

参考文献 16

[1]	Srinivasan M, Sudheer A R, Pillai R , et al. Influence of ferulic acid on γ-radiation induced DNA damage,lipid peroxidation and antioxidant status in primary culture of isolated rat heap tocytes[J]. Toxicology, 2006,228 : 249-258. doi: 10.1016/j.tox.2006.09.004 pmid: 17049709
[2]	Yu Yang . Enzymatic synthesis of ferulic acid derivatives in non-aqueous phase and preparation of electrospun instant-soluble ultrafine fiber membranes[D]. Shanghai: Donghua University, 2011.
[3]	Valerian B, Marie H A, Joelle N , et al. Nephroprotective effects of ferulic acid, Z-ligustilide and E-ligustilide isolated from Angelica sinensis against cisplatin toxicity in vitro[J]. Toxicology in Vitro, 2015,29(3) : 458-467. doi: 10.1016/j.tiv.2014.12.017 pmid: 25561245
[4]	Liu Yanhong, Yang Zijia, Zhu Jun . Preparation of ferulic acid esters and thire application in cosmetics[J]. Chemical World, 2014,11:700-704.
[5]	Zhao Wenhong, Zheng Zeyuan, Fan Yawei , et al. Antioxidant properties of ferulic acid in vitro[J]. Food Science, 2010,1(31) : 219-223.
[6]	Li Yang, Yang Zijia, Zhu Jun , et al. Chemical modification of azelaic acid and tyrosinase inhibition activity of the modified product[J]. China Surfactant Detergent＆Cosmetics, 2014,44(9) : 494-496, 528.
[7]	Liu Ce, Wang Wen, Qiao Xin , et al. Synthesis of six ferulic acid amide derivatives and determination of herbicidal activity [J]. Journal Publishing Department of Agricultural University of Hebei, 2018,41(4) : 50-55, 72.
[8]	Wang Qiuan, Li Xing, Xu Yu , et al. Synjournal and structure characterization of ferulamides[J]. Journal of Hunan University (Natural Sciences) , 2018,45(6) : 139-144.
[9]	Zhang Jianxun . Synthesis and activities of substituted cinnamyl amino acid ester derivatives[D]. Wuhan: Huazhong Agricultural University, 2010.
[10]	Maya C, Boyka S, Galya I , et al. N-Hydroxycinnamoyl amides of fluorinated amino acids: synjournal, anti-tyrosinase and DPPH scavenging activities[J]. Journal of Fluorine Chemistry, 2013,156:203-208. doi: 10.1016/j.jfluchem.2013.09.013
[11]	Wei Q Y, Jiang H, Zhang J X , et al. Synjournal of N-hydroxycinnamoyl amino acid ester analogues and their free radical scavenging and antioxidative activities[J]. Med. Chem. Res., 2012,21(8) : 1905-1911. doi: 10.1007/s00044-011-9713-2
[12]	Maya S, Vessela K K, Iskra T , et al. Synjournal of cinnamoyl and hydroxycinnamoyl amino acid conjugates and evaluation of their antioxidant[J]. Journal of Peptide Science, 2006,12:369-375. doi: 10.1002/psc.736 pmid: 16331636
[13]	Fan Q, Jiang H, Yuan E D , et al. Tyrosinase inhibitory effects and antioxidative activities of novel cinnamoyl amides with amino acid ester moiety[J]. Food Chemistry, 2012,134(2) : 1081-1087. doi: 10.1016/j.foodchem.2012.03.021
[14]	Wei Q Y, Jiang H, Zhang J X , et al. Synjournal of N-hydroxy-cinnamoylamino acid ester analogues and their free radical scavenging and antioxidative activities[J]. Medicinal Chemistry Research, 2012,21(8) : 1905-1911. doi: 10.1007/s00044-011-9713-2
[15]	Wang Xiaoqing . Evaluation on anti-oxidant activity of Curcuma longa extracts based on dpph free radical scavenging capability[J]. Drug Evaluation Research, 2011,5:360-363. doi: 10.7501/j.issn.0253-6376.[year].[issue].[sequence]
[16]	Zhang Haifen, Gao Yuntao, Na ji, et al. Scavenging activities of water-soluble ABTS + free radicals from eight species of aquatic vegetables [J]. Food Research and Develop, 2019,40(6) : 8-13, 18.

物质	IC₅₀/（μmol·L^-1）
Ⅰ	45.133
Ⅱ	47.293
Ⅲ	44.528
Ⅳ	37.567
阿魏酸	47.307
Vc	25.187

物质	IC₅₀/（μmol·L^-1）
Ⅰ	14.164
Ⅱ	13.408
Ⅲ	12.454
Ⅳ	1.689
阿魏酸	32.182
Vc	27.873

物质	溶血率/%
Ⅰ	0.134
Ⅱ	0.370
Ⅲ	0.210
Ⅳ	0.162
阿魏酸	0.232
SDS	73.187
DMSO	0.002

阿魏酰氨基酸乙酯的合成及其抗氧化活性研究

Synthesis and anti-oxidant activity of feruloylamino acid ethyl ester

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