Activation of the Kelch-like ECH-Associated Protein 1 (Keap1)/NF-E2-Related Factor 2 (Nrf2) Pathway through Covalent Modification of the 2-Alkenal Group of Aliphatic Electrophiles in Coriandrum sativum L.

被引：21

作者：

Abiko, Yumi ^{[1
]}

Mizokawa, Mai ^{[2
]}

Kumagai, Yoshito ^{[1
,2
]}

机构：

[1] Univ Tsukuba, Grad Sch Environm Sci, Fac Med, Tsukuba, Ibaraki 3058575, Japan

[2] Univ Tsukuba, Grad Sch Environm Sci, Masters Program Environm Sci, Tsukuba, Ibaraki 3058575, Japan

来源：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 2014年 / 62卷 / 45期

关键词：

Coriandrum sativum; 2-alkenal; Keap1/Nrf2; electrophile; alpha; beta-unsaturated aldehyde; ANTIOXIDANT RESPONSE ELEMENT; OXIDATIVE STRESS; OXIDOREDUCTASE-1; GENE; UNSATURATED ALDEHYDES; MASS-SPECTROMETRY; PHASE-2; ENZYMES; INDUCTION; ACROLEIN; LEAVES; KEAP1;

D O I：

10.1021/jf5030592

中图分类号：

S [农业科学];

学科分类号：

082806 [农业信息与电气工程];

摘要：

Phytochemicals able to activate the transcription factor NF-E2-related factor 2 (Nrf2) were isolated from an extract of Coriandrum sativum L. (C. sativum) leaves by preparative octadecyl silica column chromatography. Ultraperformance liquid chromatography and liquid chromatography-tandem mass spectrometry analysis of the isolated components after derivatization with 2-diphenylacetyl-1,3-inandione-1-hydrazone and experiments with HepG2 cells revealed that (E)-2-alkenals with different carbon numbers play a role in Nrf2 activation in these cells. Such Nrf2 activation appears to be attributable to S-alkylation of Kelch-like ECH-associated protein 1 (Keap1), the negative regulator for Nrf2, as determined by a biotin-PEAC(5)-maleimide assay. Interestingly, (E)-2-butenal caused Keap1 modification and Nrf2 activation, whereas butanal did not. These results suggest that (E)-2-alkenals with an alpha,beta-unsaturated aldehyde moiety, which is a common substituent in phytochemicals isolated from C. sativum leaves, activate the Keap1/Nrf2 pathway associated with cellular protection.

引用

页码：10936 / 10944

页数：9

共 41 条

[1]

Participation of covalent modification of Keap1 in the activation of Nrf2 by tert-butylbenzoquinone, an electrophilic metabolite of butylated hydroxyanisole [J].