咖啡酸的化学改性及产物抗氧化性的研究

doi:10.3969/j.issn.1001-1803.2019.02.007

Abstract

Abstract:

Caffeoyl glycine ethyl ester, caffeoyl alanine ethyl ester, caffeoyl serine ethyl ester and caffeoyl threonine ethyl ester were synthesized from L-amino acid ethyl ester hydrochloride with caffeic acid in the presence of a catalytic amount of 1-（3-dimethylaminopropyl）-3-ethylcarbodiimide hydrochloride （EDC） and 1-hydroxybenzotriazole （HOBt） . The structure of the products after the reaction was characterized by ¹H NMR and HPLC-MS. The inhibitory rates against DPPH radical and hydroxyl radical and the erythrocyte membrane irritation were investigated for the chemically modified products of caffeic acid which were compared with caffeic acid. The results show that all these four caffeic acid amide derivatives show good inhibition against DPPH radicals and hydroxyl radicals, which have introduced glycine ethyl ester, alanine ethyl ester, serine ethyl ester, and threonine ethyl ester in the molecular structure of caffeic acid. The caffeic acid amide derived from serine ethyl ester has the strongest scavenging activity against DPPH free radicals （IC₅₀=13.5 μmol/L）, while the one derived from alanine ethyl ester is the strongest in scavenging hydroxyl radicals with an IC₅₀value of 0.214 mmol/L. The results of red blood cell hemolysis show that all these four caffeic acid amide derivatives exihibit lower hemolysis ratios than caffeic acid.

Key words: cosmetic additive, caffeic acid, caffeic acid amide derivative from amino acid ethyl ester, DPPH radical, hydroxyl radical, hemolysis of erythrocytes

CLC Number:

TQ658

Dong WANG,Xue ZHAO,Jing-jiu SONG,Jun ZHU. Synthesis and the antioxidation study of the chemically modified derivatives of caffeic acid[J].China Surfactant Detergent & Cosmetics, 2019, 49(2): 98-102.

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References 16

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物质	IC₅₀/（μmol·L^-1）
a	18.6
b	29.7
c	13.5
d	14.5
CA	27.6
V_C	80.9

物质	IC₅₀/（mmol·L^-1）
a	0.340
b	0.214
c	0.244
d	0.268
CA	0.286
V_C	1.680

物质	溶血率/%
a	2.38
b	1.07
c	-0.85
d	-0.38
CA	2.39
DMSO	0.89
SDS	74.00

Synthesis and the antioxidation study of the chemically modified derivatives of caffeic acid

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