Genistein-7-O-octanoate, a lipophilized genistein, exhibits antioxidant activity through activating the Nrf2 signaling pathway in Caco-2 cells
文献类型: 外文期刊
作者: Fu, Gui 1 ; Li, Yongfu 3 ; Fan, Fangyu 4 ; Zhang, Zhaohuan 1 ; Wang, Mingfu 5 ; Zhao, Yueliang 1 ;
作者机构: 1.Shanghai Ocean Univ, Coll Food Sci & Technol, Shanghai 201306, Peoples R China
2.Shanghai Ocean Univ, Int Res Ctr Food & Hlth, Shanghai 201306, Peoples R China
3.Guizhou Acad Agr Sci, Inst Integrated Agr Dev, Guiyang 550009, Peoples R China
4.Southwest Forestry Univ, Coll Biol & Food Engn, Kunming 650224, Yunnan, Peoples R China
5.Shenzhen Univ, Coll Chem & Environm Engn, Shenzhen Key Lab Food Nutr & Hlth, Shenzhen 518060, Peoples R China
6.Shanghai Jiao Tong Univ, Sch Med, Sch Publ Hlth, Shanghai 200025, Peoples R China
关键词: Genistein; Esterification; Antioxidant mechanism; Nrf2; Caco-2
期刊名称:JOURNAL OF FUNCTIONAL FOODS ( 影响因子:3.8; 五年影响因子:4.6 )
ISSN: 1756-4646
年卷期: 2024 年 119 卷
页码:
收录情况: SCI
摘要: Genistein was esterified with nine acyl chlorides. The resulting esters were characterized using HPLC-MS and 1H and 13C NMR. The antioxidant activity of genistein esters was assessed in both chemical models and Caco-2 cells. All genistein esters exhibited lower 1,1-Diphenyl-2-picrylhydrazyl radical 2,2-Diphenyl-1-(2,4,6-trinitrophenyl) hydrazyl (DPPH) and 2, 2 '-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging activities compared to genistein. Seven genistein monoesters exhibited stronger cellular antioxidant activity (CAA) than genistein (CAA unit = 1.1), with genistein-7-O-octanoate (G-C8:0) (CAA unit = 25.9) being the strongest. Further mechanism study revealed that G-C8:0 treatment significantly enhanced the activities of antioxidative enzymes such as superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GSH-PX), along with upregulating the protein expression of nuclear factor E2-related factor (Nrf2) and its downstream antioxidases, including SOD, Heme oxygenase 1 (HO-1), and GSH-PX. Overall, these findings indicate that esterification is a promising method for augmenting the cellular antioxidant activity of parent isoflavones.
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