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...

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Veröffentlicht in:Journal of agricultural and food chemistry 2006-12, Vol.54 (26), p.10288-10293
Hauptverfasser: Kerem, Zohar, Chetrit, David, Shoseyov, Oded, Regev-Shoshani, Gilly
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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
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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. 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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. 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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. 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ispartof Journal of agricultural and food chemistry, 2006-12, Vol.54 (26), p.10288-10293
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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
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