Flax phenolic compounds as inhibitors of lipid oxidation: Elucidation of their mechanisms of action
•Lignans were more efficient than phenolic acids to prevent lipid oxidation.•Both classes of compounds presented a structure/antioxidant efficiency relationship.•Membrane inserted compounds significantly inhibited lipid oxidation.•The inner membrane fraction of lignans inhibited ∼70 % of lipid oxida...
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| Veröffentlicht in: | Food chemistry 2019-02, Vol.274, p.651-658 |
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| creator | Socrier, Larissa Quéro, Anthony Verdu, Margaux Song, Yiming Molinié, Roland Mathiron, David Pilard, Serge Mesnard, François Morandat, Sandrine |
| description | •Lignans were more efficient than phenolic acids to prevent lipid oxidation.•Both classes of compounds presented a structure/antioxidant efficiency relationship.•Membrane inserted compounds significantly inhibited lipid oxidation.•The inner membrane fraction of lignans inhibited ∼70 % of lipid oxidation.
Polyunsaturated fatty acids are particularly sensitive to the damages due to reactive oxygen species and lipid oxidation has been reported to be involved in the degradation of food as well as in the early stages of several diseases. Our objective was to study the mechanisms of action of flax (Linum usitatissimum) phenolic compounds to prevent membrane lipid oxidation. To do so, several biophysical techniques (oxidative stress, surface tension, fluorescence spectroscopy and HPLC) were used to investigate the ability of the compounds to prevent lipid oxidation and to interact with membranes. We evidenced a relationship between the structure and the antioxidant efficiency as aglycone compounds were significantly more efficient (p |
| doi_str_mv | 10.1016/j.foodchem.2018.08.126 |
| format | Article |
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Polyunsaturated fatty acids are particularly sensitive to the damages due to reactive oxygen species and lipid oxidation has been reported to be involved in the degradation of food as well as in the early stages of several diseases. Our objective was to study the mechanisms of action of flax (Linum usitatissimum) phenolic compounds to prevent membrane lipid oxidation. To do so, several biophysical techniques (oxidative stress, surface tension, fluorescence spectroscopy and HPLC) were used to investigate the ability of the compounds to prevent lipid oxidation and to interact with membranes. We evidenced a relationship between the structure and the antioxidant efficiency as aglycone compounds were significantly more efficient (p < 0.05) than glucoside compounds. In addition, our results revealed that aglycone lignans spontaneously penetrated the membrane contrary to aglycone hydroxycinnamic acids. To conclude, the comparison of the antioxidant efficiencies revealed that membrane inserted compounds better inhibited lipid oxidation than non-inserted compounds.</description><identifier>ISSN: 0308-8146</identifier><identifier>EISSN: 1873-7072</identifier><identifier>DOI: 10.1016/j.foodchem.2018.08.126</identifier><identifier>PMID: 30372990</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Antioxidant ; Antioxidants - chemistry ; Biochemistry ; Biochemistry, Molecular Biology ; Fatty Acids, Unsaturated - chemistry ; Fatty Acids, Unsaturated - metabolism ; Flax - chemistry ; Flax - metabolism ; Flaxseed ; Life Sciences ; Lignans - chemistry ; Lignans - metabolism ; Lipid oxidation ; Lipid Peroxidation ; Liposomes - chemistry ; Liposomes - metabolism ; Model membranes ; Permeability ; Phenolic compounds ; Phenols - chemistry ; Phenols - metabolism ; Spectrophotometry, Ultraviolet</subject><ispartof>Food chemistry, 2019-02, Vol.274, p.651-658</ispartof><rights>2018 Elsevier Ltd</rights><rights>Copyright © 2018 Elsevier Ltd. All rights reserved.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c439t-562b5e9741e7d92aad25c83775c2b4a34c943b51bdf76412c02088acb666bdea3</citedby><cites>FETCH-LOGICAL-c439t-562b5e9741e7d92aad25c83775c2b4a34c943b51bdf76412c02088acb666bdea3</cites><orcidid>0000-0001-7948-317X ; 0000-0003-4399-8838 ; 0000-0002-9167-526X ; 0000-0002-7626-3902 ; 0000-0002-2119-3089 ; 0000-0001-5478-3029 ; 0000-0001-9673-4356</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.foodchem.2018.08.126$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30372990$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://utc.hal.science/hal-01988885$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Socrier, Larissa</creatorcontrib><creatorcontrib>Quéro, Anthony</creatorcontrib><creatorcontrib>Verdu, Margaux</creatorcontrib><creatorcontrib>Song, Yiming</creatorcontrib><creatorcontrib>Molinié, Roland</creatorcontrib><creatorcontrib>Mathiron, David</creatorcontrib><creatorcontrib>Pilard, Serge</creatorcontrib><creatorcontrib>Mesnard, François</creatorcontrib><creatorcontrib>Morandat, Sandrine</creatorcontrib><title>Flax phenolic compounds as inhibitors of lipid oxidation: Elucidation of their mechanisms of action</title><title>Food chemistry</title><addtitle>Food Chem</addtitle><description>•Lignans were more efficient than phenolic acids to prevent lipid oxidation.•Both classes of compounds presented a structure/antioxidant efficiency relationship.•Membrane inserted compounds significantly inhibited lipid oxidation.•The inner membrane fraction of lignans inhibited ∼70 % of lipid oxidation.
Polyunsaturated fatty acids are particularly sensitive to the damages due to reactive oxygen species and lipid oxidation has been reported to be involved in the degradation of food as well as in the early stages of several diseases. Our objective was to study the mechanisms of action of flax (Linum usitatissimum) phenolic compounds to prevent membrane lipid oxidation. To do so, several biophysical techniques (oxidative stress, surface tension, fluorescence spectroscopy and HPLC) were used to investigate the ability of the compounds to prevent lipid oxidation and to interact with membranes. We evidenced a relationship between the structure and the antioxidant efficiency as aglycone compounds were significantly more efficient (p < 0.05) than glucoside compounds. In addition, our results revealed that aglycone lignans spontaneously penetrated the membrane contrary to aglycone hydroxycinnamic acids. To conclude, the comparison of the antioxidant efficiencies revealed that membrane inserted compounds better inhibited lipid oxidation than non-inserted compounds.</description><subject>Antioxidant</subject><subject>Antioxidants - chemistry</subject><subject>Biochemistry</subject><subject>Biochemistry, Molecular Biology</subject><subject>Fatty Acids, Unsaturated - chemistry</subject><subject>Fatty Acids, Unsaturated - metabolism</subject><subject>Flax - chemistry</subject><subject>Flax - metabolism</subject><subject>Flaxseed</subject><subject>Life Sciences</subject><subject>Lignans - chemistry</subject><subject>Lignans - metabolism</subject><subject>Lipid oxidation</subject><subject>Lipid Peroxidation</subject><subject>Liposomes - chemistry</subject><subject>Liposomes - metabolism</subject><subject>Model membranes</subject><subject>Permeability</subject><subject>Phenolic compounds</subject><subject>Phenols - chemistry</subject><subject>Phenols - metabolism</subject><subject>Spectrophotometry, Ultraviolet</subject><issn>0308-8146</issn><issn>1873-7072</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUtv1TAQhS1ERW8Lf6HyEhYJfiR-sKKq-kC6Ujewthx7ovgqiYOdVOXfk_TedltvLM98Z0Y-B6ErSkpKqPh-KNsYvetgKBmhqiSqpEx8QDuqJC8kkewj2hFOVKFoJc7RRc4HQsjGfkLnnHDJtCY75O56-4ynDsbYB4ddHKa4jD5jm3EYu9CEOaaMY4v7MAWP43Pwdg5x_IFv-8WdHlt_7iAkPIDr7Bjy8KKxbut-Rmet7TN8Od2X6M_d7e-bh2L_eP_r5npfuIrruagFa2rQsqIgvWbWelY7xaWsHWsqyyunK97UtPGtFBVlbv2NUtY1QojGg-WX6Ntxbmd7M6Uw2PTPRBvMw_XebDVCtVpP_URX9uuRnVL8u0CezRCyg763I8QlG0aZpFpoVa2oOKIuxZwTtG-zKTFbGOZgXsMwm8GGKLOGsQqvTjuWZgD_Jnt1fwV-HgFYXXkKkEx2AUYHPiRws_ExvLfjPx4DnpU</recordid><startdate>20190215</startdate><enddate>20190215</enddate><creator>Socrier, Larissa</creator><creator>Quéro, Anthony</creator><creator>Verdu, Margaux</creator><creator>Song, Yiming</creator><creator>Molinié, Roland</creator><creator>Mathiron, David</creator><creator>Pilard, Serge</creator><creator>Mesnard, François</creator><creator>Morandat, Sandrine</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0001-7948-317X</orcidid><orcidid>https://orcid.org/0000-0003-4399-8838</orcidid><orcidid>https://orcid.org/0000-0002-9167-526X</orcidid><orcidid>https://orcid.org/0000-0002-7626-3902</orcidid><orcidid>https://orcid.org/0000-0002-2119-3089</orcidid><orcidid>https://orcid.org/0000-0001-5478-3029</orcidid><orcidid>https://orcid.org/0000-0001-9673-4356</orcidid></search><sort><creationdate>20190215</creationdate><title>Flax phenolic compounds as inhibitors of lipid oxidation: Elucidation of their mechanisms of action</title><author>Socrier, Larissa ; Quéro, Anthony ; Verdu, Margaux ; Song, Yiming ; Molinié, Roland ; Mathiron, David ; Pilard, Serge ; Mesnard, François ; Morandat, Sandrine</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c439t-562b5e9741e7d92aad25c83775c2b4a34c943b51bdf76412c02088acb666bdea3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Antioxidant</topic><topic>Antioxidants - chemistry</topic><topic>Biochemistry</topic><topic>Biochemistry, Molecular Biology</topic><topic>Fatty Acids, Unsaturated - chemistry</topic><topic>Fatty Acids, Unsaturated - metabolism</topic><topic>Flax - chemistry</topic><topic>Flax - metabolism</topic><topic>Flaxseed</topic><topic>Life Sciences</topic><topic>Lignans - chemistry</topic><topic>Lignans - metabolism</topic><topic>Lipid oxidation</topic><topic>Lipid Peroxidation</topic><topic>Liposomes - chemistry</topic><topic>Liposomes - metabolism</topic><topic>Model membranes</topic><topic>Permeability</topic><topic>Phenolic compounds</topic><topic>Phenols - chemistry</topic><topic>Phenols - metabolism</topic><topic>Spectrophotometry, Ultraviolet</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Socrier, Larissa</creatorcontrib><creatorcontrib>Quéro, Anthony</creatorcontrib><creatorcontrib>Verdu, Margaux</creatorcontrib><creatorcontrib>Song, Yiming</creatorcontrib><creatorcontrib>Molinié, Roland</creatorcontrib><creatorcontrib>Mathiron, David</creatorcontrib><creatorcontrib>Pilard, Serge</creatorcontrib><creatorcontrib>Mesnard, François</creatorcontrib><creatorcontrib>Morandat, Sandrine</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Socrier, Larissa</au><au>Quéro, Anthony</au><au>Verdu, Margaux</au><au>Song, Yiming</au><au>Molinié, Roland</au><au>Mathiron, David</au><au>Pilard, Serge</au><au>Mesnard, François</au><au>Morandat, Sandrine</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Flax phenolic compounds as inhibitors of lipid oxidation: Elucidation of their mechanisms of action</atitle><jtitle>Food chemistry</jtitle><addtitle>Food Chem</addtitle><date>2019-02-15</date><risdate>2019</risdate><volume>274</volume><spage>651</spage><epage>658</epage><pages>651-658</pages><issn>0308-8146</issn><eissn>1873-7072</eissn><abstract>•Lignans were more efficient than phenolic acids to prevent lipid oxidation.•Both classes of compounds presented a structure/antioxidant efficiency relationship.•Membrane inserted compounds significantly inhibited lipid oxidation.•The inner membrane fraction of lignans inhibited ∼70 % of lipid oxidation.
Polyunsaturated fatty acids are particularly sensitive to the damages due to reactive oxygen species and lipid oxidation has been reported to be involved in the degradation of food as well as in the early stages of several diseases. Our objective was to study the mechanisms of action of flax (Linum usitatissimum) phenolic compounds to prevent membrane lipid oxidation. To do so, several biophysical techniques (oxidative stress, surface tension, fluorescence spectroscopy and HPLC) were used to investigate the ability of the compounds to prevent lipid oxidation and to interact with membranes. We evidenced a relationship between the structure and the antioxidant efficiency as aglycone compounds were significantly more efficient (p < 0.05) than glucoside compounds. In addition, our results revealed that aglycone lignans spontaneously penetrated the membrane contrary to aglycone hydroxycinnamic acids. To conclude, the comparison of the antioxidant efficiencies revealed that membrane inserted compounds better inhibited lipid oxidation than non-inserted compounds.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>30372990</pmid><doi>10.1016/j.foodchem.2018.08.126</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-7948-317X</orcidid><orcidid>https://orcid.org/0000-0003-4399-8838</orcidid><orcidid>https://orcid.org/0000-0002-9167-526X</orcidid><orcidid>https://orcid.org/0000-0002-7626-3902</orcidid><orcidid>https://orcid.org/0000-0002-2119-3089</orcidid><orcidid>https://orcid.org/0000-0001-5478-3029</orcidid><orcidid>https://orcid.org/0000-0001-9673-4356</orcidid></addata></record> |
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| subjects | Antioxidant Antioxidants - chemistry Biochemistry Biochemistry, Molecular Biology Fatty Acids, Unsaturated - chemistry Fatty Acids, Unsaturated - metabolism Flax - chemistry Flax - metabolism Flaxseed Life Sciences Lignans - chemistry Lignans - metabolism Lipid oxidation Lipid Peroxidation Liposomes - chemistry Liposomes - metabolism Model membranes Permeability Phenolic compounds Phenols - chemistry Phenols - metabolism Spectrophotometry, Ultraviolet |
| title | Flax phenolic compounds as inhibitors of lipid oxidation: Elucidation of their mechanisms of action |
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