Protection of Lipids from Oxidation by Epicatechin, trans-Resveratrol, and Gallic and Caffeic Acids in Intestinal Model Systems
Consumption of polyphenols is associated with health promotion through diet, although many are poorly absorbed in animals and humans alike. Lipid peroxides may reach the intestine and initiate deleterious oxidation. Here we measured inhibition of the oxidation of linoleic acid (LA) in authentic flui...
Gespeichert in:
Veröffentlicht in: | Journal of agricultural and food chemistry 2006-12, Vol.54 (26), p.10288-10293 |
---|---|
Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 10293 |
---|---|
container_issue | 26 |
container_start_page | 10288 |
container_title | Journal of agricultural and food chemistry |
container_volume | 54 |
creator | Kerem, Zohar Chetrit, David Shoseyov, Oded Regev-Shoshani, Gilly |
description | Consumption of polyphenols is associated with health promotion through diet, although many are poorly absorbed in animals and humans alike. Lipid peroxides may reach the intestine and initiate deleterious oxidation. Here we measured inhibition of the oxidation of linoleic acid (LA) in authentic fluid from rat small intestine (RIF) by two dietary polyphenols, a flavonoid, epicatechin (EC), and a stilbene, resveratrol (RV), and by gallic (GA) and caffeic (CA) acids, and their partition coefficients. Both polyphenols inhibited 80%, and CA inhibited 65%, of the production of hexanal. GA was the weakest antioxidant in this assay. Interestingly, measuring peroxides production in RIF showed that only epicatechin inhibited the first stage of oxidation. The oxidizing agent, the antioxidant comound, the solution pH and lipophilicity are known to affect the total antioxidative activity. We suggest that the mechanism of this activity changes in accord with the environment: i.e., RV may act as a free radial scavenger, but here, in protecting lipids in intestinal fluid from oxidation, it acts as a hydrogen atom donor. Since the concentration of phenolics is much higher in the intestinal fluid than is ever achieved in plasma or other body tissues, it is suggested that their antioxidant activity could be exerted in the gastrointestinal tract (GIT), breaking the propagation of lipid peroxides oxidation and production of toxic compounds. Keywords: Gastrointestinal tract; dietary antioxidants; phenolics; partition coefficient |
doi_str_mv | 10.1021/jf0621828 |
format | Article |
fullrecord | <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_jf0621828</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>h05410270</sourcerecordid><originalsourceid>FETCH-LOGICAL-a405t-8826168635478c7fa96251c24c9021f8e0e64eb7de3e8aa0a3e38d49a68714543</originalsourceid><addsrcrecordid>eNptkM1uEzEYRS0EoqGw4AXAmy6QOq3_7SyrqH8iVaOmFUvri8cGh8k4sqeoWfHquE3UbFj5k-7Rte5B6DMlJ5QweroMRDFqmHmDRlQy0khKzVs0IjVsjFT0AH0oZUkIMVKT9-iAaqq11GyE_s5yGrwbYupxCnga17EtOOS0wrdPsYWXYLHB5-vooIK_Yn-Mhwx9ae58-eMzDDl1xxj6Fl9C10X3ck4gBF_vM_dcF3t83Q--DLGHDt-k1nd4vimDX5WP6F2ArvhPu_cQPVyc30-umunt5fXkbNqAIHJojGGKKqO4FNo4HWCsmKSOCTeuG4PxxCvhF7r13BsAAtxz04oxKKOpkIIfom_bXpdTKdkHu85xBXljKbHPEu2rxMp-2bLrx8XKt3tyZ60CRzsAioMuVB0ulj1nuDJcjCvXbLlYtz695pB_W6W5lvZ-Nrc3sx-TO_b9yl5U_uuWD5As_My182HOCOWEaCEJ0_ufwRW7TI-5Ci3_mfAP0tydNQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Protection of Lipids from Oxidation by Epicatechin, trans-Resveratrol, and Gallic and Caffeic Acids in Intestinal Model Systems</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Kerem, Zohar ; Chetrit, David ; Shoseyov, Oded ; Regev-Shoshani, Gilly</creator><creatorcontrib>Kerem, Zohar ; Chetrit, David ; Shoseyov, Oded ; Regev-Shoshani, Gilly</creatorcontrib><description>Consumption of polyphenols is associated with health promotion through diet, although many are poorly absorbed in animals and humans alike. Lipid peroxides may reach the intestine and initiate deleterious oxidation. Here we measured inhibition of the oxidation of linoleic acid (LA) in authentic fluid from rat small intestine (RIF) by two dietary polyphenols, a flavonoid, epicatechin (EC), and a stilbene, resveratrol (RV), and by gallic (GA) and caffeic (CA) acids, and their partition coefficients. Both polyphenols inhibited 80%, and CA inhibited 65%, of the production of hexanal. GA was the weakest antioxidant in this assay. Interestingly, measuring peroxides production in RIF showed that only epicatechin inhibited the first stage of oxidation. The oxidizing agent, the antioxidant comound, the solution pH and lipophilicity are known to affect the total antioxidative activity. We suggest that the mechanism of this activity changes in accord with the environment: i.e., RV may act as a free radial scavenger, but here, in protecting lipids in intestinal fluid from oxidation, it acts as a hydrogen atom donor. Since the concentration of phenolics is much higher in the intestinal fluid than is ever achieved in plasma or other body tissues, it is suggested that their antioxidant activity could be exerted in the gastrointestinal tract (GIT), breaking the propagation of lipid peroxides oxidation and production of toxic compounds. Keywords: Gastrointestinal tract; dietary antioxidants; phenolics; partition coefficient</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf0621828</identifier><identifier>PMID: 17177572</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; antioxidant activity ; Antioxidants - pharmacology ; Biological and medical sciences ; Body Fluids - chemistry ; caffeic acid ; Caffeic Acids - pharmacology ; Catechin - pharmacology ; epicatechin ; Food industries ; Fundamental and applied biological sciences. Psychology ; gallic acid ; Gallic Acid - pharmacology ; gastric juice ; in vitro studies ; intestinal fluid ; Intestines - metabolism ; linoleic acid ; Linoleic Acids ; Lipid Peroxidation - drug effects ; Male ; Models, Biological ; oxidation ; Rats ; Rats, Sprague-Dawley ; resveratrol ; small intestine ; Stilbenes - pharmacology</subject><ispartof>Journal of agricultural and food chemistry, 2006-12, Vol.54 (26), p.10288-10293</ispartof><rights>Copyright © 2006 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a405t-8826168635478c7fa96251c24c9021f8e0e64eb7de3e8aa0a3e38d49a68714543</citedby><cites>FETCH-LOGICAL-a405t-8826168635478c7fa96251c24c9021f8e0e64eb7de3e8aa0a3e38d49a68714543</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf0621828$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf0621828$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18368349$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17177572$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kerem, Zohar</creatorcontrib><creatorcontrib>Chetrit, David</creatorcontrib><creatorcontrib>Shoseyov, Oded</creatorcontrib><creatorcontrib>Regev-Shoshani, Gilly</creatorcontrib><title>Protection of Lipids from Oxidation by Epicatechin, trans-Resveratrol, and Gallic and Caffeic Acids in Intestinal Model Systems</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Consumption of polyphenols is associated with health promotion through diet, although many are poorly absorbed in animals and humans alike. Lipid peroxides may reach the intestine and initiate deleterious oxidation. Here we measured inhibition of the oxidation of linoleic acid (LA) in authentic fluid from rat small intestine (RIF) by two dietary polyphenols, a flavonoid, epicatechin (EC), and a stilbene, resveratrol (RV), and by gallic (GA) and caffeic (CA) acids, and their partition coefficients. Both polyphenols inhibited 80%, and CA inhibited 65%, of the production of hexanal. GA was the weakest antioxidant in this assay. Interestingly, measuring peroxides production in RIF showed that only epicatechin inhibited the first stage of oxidation. The oxidizing agent, the antioxidant comound, the solution pH and lipophilicity are known to affect the total antioxidative activity. We suggest that the mechanism of this activity changes in accord with the environment: i.e., RV may act as a free radial scavenger, but here, in protecting lipids in intestinal fluid from oxidation, it acts as a hydrogen atom donor. Since the concentration of phenolics is much higher in the intestinal fluid than is ever achieved in plasma or other body tissues, it is suggested that their antioxidant activity could be exerted in the gastrointestinal tract (GIT), breaking the propagation of lipid peroxides oxidation and production of toxic compounds. Keywords: Gastrointestinal tract; dietary antioxidants; phenolics; partition coefficient</description><subject>Animals</subject><subject>antioxidant activity</subject><subject>Antioxidants - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Body Fluids - chemistry</subject><subject>caffeic acid</subject><subject>Caffeic Acids - pharmacology</subject><subject>Catechin - pharmacology</subject><subject>epicatechin</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>gallic acid</subject><subject>Gallic Acid - pharmacology</subject><subject>gastric juice</subject><subject>in vitro studies</subject><subject>intestinal fluid</subject><subject>Intestines - metabolism</subject><subject>linoleic acid</subject><subject>Linoleic Acids</subject><subject>Lipid Peroxidation - drug effects</subject><subject>Male</subject><subject>Models, Biological</subject><subject>oxidation</subject><subject>Rats</subject><subject>Rats, Sprague-Dawley</subject><subject>resveratrol</subject><subject>small intestine</subject><subject>Stilbenes - pharmacology</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM1uEzEYRS0EoqGw4AXAmy6QOq3_7SyrqH8iVaOmFUvri8cGh8k4sqeoWfHquE3UbFj5k-7Rte5B6DMlJ5QweroMRDFqmHmDRlQy0khKzVs0IjVsjFT0AH0oZUkIMVKT9-iAaqq11GyE_s5yGrwbYupxCnga17EtOOS0wrdPsYWXYLHB5-vooIK_Yn-Mhwx9ae58-eMzDDl1xxj6Fl9C10X3ck4gBF_vM_dcF3t83Q--DLGHDt-k1nd4vimDX5WP6F2ArvhPu_cQPVyc30-umunt5fXkbNqAIHJojGGKKqO4FNo4HWCsmKSOCTeuG4PxxCvhF7r13BsAAtxz04oxKKOpkIIfom_bXpdTKdkHu85xBXljKbHPEu2rxMp-2bLrx8XKt3tyZ60CRzsAioMuVB0ulj1nuDJcjCvXbLlYtz695pB_W6W5lvZ-Nrc3sx-TO_b9yl5U_uuWD5As_My182HOCOWEaCEJ0_ufwRW7TI-5Ci3_mfAP0tydNQ</recordid><startdate>20061227</startdate><enddate>20061227</enddate><creator>Kerem, Zohar</creator><creator>Chetrit, David</creator><creator>Shoseyov, Oded</creator><creator>Regev-Shoshani, Gilly</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20061227</creationdate><title>Protection of Lipids from Oxidation by Epicatechin, trans-Resveratrol, and Gallic and Caffeic Acids in Intestinal Model Systems</title><author>Kerem, Zohar ; Chetrit, David ; Shoseyov, Oded ; Regev-Shoshani, Gilly</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a405t-8826168635478c7fa96251c24c9021f8e0e64eb7de3e8aa0a3e38d49a68714543</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Animals</topic><topic>antioxidant activity</topic><topic>Antioxidants - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Body Fluids - chemistry</topic><topic>caffeic acid</topic><topic>Caffeic Acids - pharmacology</topic><topic>Catechin - pharmacology</topic><topic>epicatechin</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>gallic acid</topic><topic>Gallic Acid - pharmacology</topic><topic>gastric juice</topic><topic>in vitro studies</topic><topic>intestinal fluid</topic><topic>Intestines - metabolism</topic><topic>linoleic acid</topic><topic>Linoleic Acids</topic><topic>Lipid Peroxidation - drug effects</topic><topic>Male</topic><topic>Models, Biological</topic><topic>oxidation</topic><topic>Rats</topic><topic>Rats, Sprague-Dawley</topic><topic>resveratrol</topic><topic>small intestine</topic><topic>Stilbenes - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kerem, Zohar</creatorcontrib><creatorcontrib>Chetrit, David</creatorcontrib><creatorcontrib>Shoseyov, Oded</creatorcontrib><creatorcontrib>Regev-Shoshani, Gilly</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kerem, Zohar</au><au>Chetrit, David</au><au>Shoseyov, Oded</au><au>Regev-Shoshani, Gilly</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Protection of Lipids from Oxidation by Epicatechin, trans-Resveratrol, and Gallic and Caffeic Acids in Intestinal Model Systems</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2006-12-27</date><risdate>2006</risdate><volume>54</volume><issue>26</issue><spage>10288</spage><epage>10293</epage><pages>10288-10293</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Consumption of polyphenols is associated with health promotion through diet, although many are poorly absorbed in animals and humans alike. Lipid peroxides may reach the intestine and initiate deleterious oxidation. Here we measured inhibition of the oxidation of linoleic acid (LA) in authentic fluid from rat small intestine (RIF) by two dietary polyphenols, a flavonoid, epicatechin (EC), and a stilbene, resveratrol (RV), and by gallic (GA) and caffeic (CA) acids, and their partition coefficients. Both polyphenols inhibited 80%, and CA inhibited 65%, of the production of hexanal. GA was the weakest antioxidant in this assay. Interestingly, measuring peroxides production in RIF showed that only epicatechin inhibited the first stage of oxidation. The oxidizing agent, the antioxidant comound, the solution pH and lipophilicity are known to affect the total antioxidative activity. We suggest that the mechanism of this activity changes in accord with the environment: i.e., RV may act as a free radial scavenger, but here, in protecting lipids in intestinal fluid from oxidation, it acts as a hydrogen atom donor. Since the concentration of phenolics is much higher in the intestinal fluid than is ever achieved in plasma or other body tissues, it is suggested that their antioxidant activity could be exerted in the gastrointestinal tract (GIT), breaking the propagation of lipid peroxides oxidation and production of toxic compounds. Keywords: Gastrointestinal tract; dietary antioxidants; phenolics; partition coefficient</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>17177572</pmid><doi>10.1021/jf0621828</doi><tpages>6</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0021-8561 |
ispartof | Journal of agricultural and food chemistry, 2006-12, Vol.54 (26), p.10288-10293 |
issn | 0021-8561 1520-5118 |
language | eng |
recordid | cdi_crossref_primary_10_1021_jf0621828 |
source | MEDLINE; American Chemical Society Journals |
subjects | Animals antioxidant activity Antioxidants - pharmacology Biological and medical sciences Body Fluids - chemistry caffeic acid Caffeic Acids - pharmacology Catechin - pharmacology epicatechin Food industries Fundamental and applied biological sciences. Psychology gallic acid Gallic Acid - pharmacology gastric juice in vitro studies intestinal fluid Intestines - metabolism linoleic acid Linoleic Acids Lipid Peroxidation - drug effects Male Models, Biological oxidation Rats Rats, Sprague-Dawley resveratrol small intestine Stilbenes - pharmacology |
title | Protection of Lipids from Oxidation by Epicatechin, trans-Resveratrol, and Gallic and Caffeic Acids in Intestinal Model Systems |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-11T12%3A56%3A21IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Protection%20of%20Lipids%20from%20Oxidation%20by%20Epicatechin,%20trans-Resveratrol,%20and%20Gallic%20and%20Caffeic%20Acids%20in%20Intestinal%20Model%20Systems&rft.jtitle=Journal%20of%20agricultural%20and%20food%20chemistry&rft.au=Kerem,%20Zohar&rft.date=2006-12-27&rft.volume=54&rft.issue=26&rft.spage=10288&rft.epage=10293&rft.pages=10288-10293&rft.issn=0021-8561&rft.eissn=1520-5118&rft.coden=JAFCAU&rft_id=info:doi/10.1021/jf0621828&rft_dat=%3Cacs_cross%3Eh05410270%3C/acs_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/17177572&rfr_iscdi=true |