Literature DB >> 28460970

3,4-Dihydroxyphenylacetic acid is a predominant biologically-active catabolite of quercetin glycosides.

Yue Tang1, Sayaka Nakashima2, Shunya Saiki2, Yui Myoi2, Naomi Abe2, Shoko Kuwazuru3, Beiwei Zhu4, Hitoshi Ashida5, Yoshiyuki Murata2, Yoshimasa Nakamura6.   

Abstract

Since dietary flavonoid glycosides, including quercetin 4'-glucoside from onion, are poorly absorbed from the gastrointestinal tract, they are converted into smaller phenolic acids, which can be absorbed into the circulation. The purpose of this study was to compare the effects of the major phenolic acid catabolites of quercetin 4'-glucoside, including 3,4-dihydroxyphenylacetic acid (DOPAC), 3-hydroxyphenylacetic acid, 3,4-dihydroxybenzoic acid (protocatechuic acid) and hippuric acid, on the antioxidant activity and phase II cytoprotective enzyme induction in vitro. Both DOPAC and protocatechuic acid, having a catechol moiety, exhibited both DPPH radical scavenging and superoxide dismutase-like activities, whereas 3-hydroxyphenyl acetic acid and hippuric acid did not. DOPAC also more potently enhanced the gene expression of several phase II drug-metabolizing enzymes than the other phenolic acid catabolites. DOPAC significantly inhibited the hydrogen peroxide-induced cytotoxicity in hepatocytes with the enhancement of the total glutathione S-transferase activity. In conclusion, DOPAC may play a key role in the antioxidative potential of the colonic lumen after the ingestion of the quercetin glycoside-rich onion.
Copyright © 2016 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  3,4-Dihydroxyphenylacetic acid; 3,4-Dihydroxyphenylacetic acid (PubChem CID: 547); 3-Hydroxyphenylacetic acid (PubChem CID: 12,122); Antioxidant; Hippuric acid (PubChem CID: 464); Phase II drug-metabolizing enzymes; Protocatechuic acid (PubChem CID: 72); Quercetin; Quercetin (PubChem CID: 5,280,343)

Year:  2016        PMID: 28460970     DOI: 10.1016/j.foodres.2016.09.034

Source DB:  PubMed          Journal:  Food Res Int        ISSN: 0963-9969            Impact factor:   6.475


  6 in total

1.  Black Raspberries Suppress Colorectal Cancer by Enhancing Smad4 Expression in Colonic Epithelium and Natural Killer Cells.

Authors:  Yi-Wen Huang; Chien-Wei Lin; Pan Pan; Tianjiao Shan; Carla Elena Echeveste; Yue Yang Mo; Hsin-Tzu Wang; Mohammed Aldakkak; Susan Tsai; Kiyoko Oshima; Martha Yearsley; Jianbo Xiao; Hui Cao; Chongde Sun; Ming Du; Weibin Bai; Jianhua Yu; Li-Shu Wang
Journal:  Front Immunol       Date:  2020-12-14       Impact factor: 7.561

2.  Impact of High-Pressure Processed Onion on Colonic Metabolism Using a Dynamic Gastrointestinal Digestion Simulator.

Authors:  Irene Fernández-Jalao; Claudia Balderas; María V Calvo; Javier Fontecha; Concepción Sánchez-Moreno; Begoña De Ancos
Journal:  Metabolites       Date:  2021-04-22

3.  A Major Intestinal Catabolite of Quercetin Glycosides, 3-Hydroxyphenylacetic Acid, Protects the Hepatocytes from the Acetaldehyde-Induced Cytotoxicity through the Enhancement of the Total Aldehyde Dehydrogenase Activity.

Authors:  Yujia Liu; Takumi Myojin; Kexin Li; Ayuki Kurita; Masayuki Seto; Ayano Motoyama; Xiaoyang Liu; Ayano Satoh; Shintaro Munemasa; Yoshiyuki Murata; Toshiyuki Nakamura; Yoshimasa Nakamura
Journal:  Int J Mol Sci       Date:  2022-02-03       Impact factor: 5.923

4.  Dietary Fibres Differentially Impact on the Production of Phenolic Acids from Rutin in an In Vitro Fermentation Model of the Human Gut Microbiota.

Authors:  Jaroslav Havlik; Vittoria Marinello; Andrew Gardyne; Min Hou; William Mullen; Douglas J Morrison; Thomas Preston; Emilie Combet; Christine A Edwards
Journal:  Nutrients       Date:  2020-05-28       Impact factor: 5.717

Review 5.  Microbial Metabolites of Flavan-3-Ols and Their Biological Activity.

Authors:  Estefanía Márquez Campos; Peter Stehle; Marie-Christine Simon
Journal:  Nutrients       Date:  2019-09-20       Impact factor: 5.717

6.  Quercetin Intervention Alleviates Offspring's Oxidative Stress, Inflammation, and Tight Junction Damage in the Colon Induced by Maternal Fine Particulate Matter (PM2.5) Exposure through the Reduction of Bacteroides.

Authors:  Wei Liu; Yalin Zhou; Yong Qin; Lanlan Yu; Ruijun Li; Yuhan Chen; Yajun Xu
Journal:  Nutrients       Date:  2020-10-11       Impact factor: 5.717

  6 in total

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