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

Abstract

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

CLC Number:

TQ658

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.

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References 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

Synthesis and anti-oxidant activity of feruloylamino acid ethyl ester

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