Benzoic and Cinnamic Acid Derivatives as Antioxidants: Structure−Activity Relation
The antioxidant activity of four derivatives of benzoic acid was systematically compared with the activity of the four homologous derivatives of cinnamic acid. The couples of compounds differed for the kind of aromatic substitution (p-hydroxy, p-hydroxymethoxy, p-hydroxydimethoxy, dihydroxy). The an...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 1999-04, Vol.47 (4), p.1453-1459 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Natella, Fausta Nardini, Mirella Di Felice, Maurizio Scaccini, Cristina |
| description | The antioxidant activity of four derivatives of benzoic acid was systematically compared with the activity of the four homologous derivatives of cinnamic acid. The couples of compounds differed for the kind of aromatic substitution (p-hydroxy, p-hydroxymethoxy, p-hydroxydimethoxy, dihydroxy). The antioxidant activity was measured using (i) a competition kinetic test, to measure the relative capacity to quench peroxyl radical and (ii) the in vitro oxidative modification of human low-density lipoprotein (LDL), initiated by 2,2‘-azobis(amidinopropane) dihydrochloride or catalyzed by Cu(II). In both models, cinnamic acids were more efficient than their benzoic counterparts. As for the influence of the aromatic substitution, in the kinetic test the antioxidant activity increased in the sequence p-hydroxy < p-hydroxymethoxy < dihydroxy < p-hydroxydimethoxy. In contrast, in the LDL system, the dihydroxy acids had an antioxidant capacity equal to or higher than that of the p-hydroxydimethoxy acids. Keywords: Benzoic acids; cinnamic acids; antioxidants; low-density lipoprotein |
| doi_str_mv | 10.1021/jf980737w |
| format | Article |
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The couples of compounds differed for the kind of aromatic substitution (p-hydroxy, p-hydroxymethoxy, p-hydroxydimethoxy, dihydroxy). The antioxidant activity was measured using (i) a competition kinetic test, to measure the relative capacity to quench peroxyl radical and (ii) the in vitro oxidative modification of human low-density lipoprotein (LDL), initiated by 2,2‘-azobis(amidinopropane) dihydrochloride or catalyzed by Cu(II). In both models, cinnamic acids were more efficient than their benzoic counterparts. As for the influence of the aromatic substitution, in the kinetic test the antioxidant activity increased in the sequence p-hydroxy < p-hydroxymethoxy < dihydroxy < p-hydroxydimethoxy. In contrast, in the LDL system, the dihydroxy acids had an antioxidant capacity equal to or higher than that of the p-hydroxydimethoxy acids. Keywords: Benzoic acids; cinnamic acids; antioxidants; low-density lipoprotein</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf980737w</identifier><identifier>PMID: 10563998</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>2,2'-azobis(amidinopropane) dihydrochloride ; Antioxidants ; azo compounds ; Benzoates - chemistry ; Benzoates - pharmacology ; benzoic acid ; Biological and medical sciences ; Cinnamates - chemistry ; Cinnamates - pharmacology ; cinnamic acid ; copper ; derivatives ; Food additives ; Food industries ; free radicals ; Fundamental and applied biological sciences. Psychology ; General aspects ; Humans ; inhibition ; Kinetics ; Lipoproteins, LDL - blood ; Lipoproteins, LDL - drug effects ; Lipoproteins, LDL - metabolism ; low density lipoprotein ; metal ions ; oxidation ; peroxyl radicals ; reduction ; Structure-Activity Relationship ; structure-activity relationships</subject><ispartof>Journal of agricultural and food chemistry, 1999-04, Vol.47 (4), p.1453-1459</ispartof><rights>Copyright © 1999 American Chemical Society</rights><rights>1999 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a468t-b9912428d687255f2653ebbdc718ac37921811b2a4678b1ad075fd0c874ad1213</citedby><cites>FETCH-LOGICAL-a468t-b9912428d687255f2653ebbdc718ac37921811b2a4678b1ad075fd0c874ad1213</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/jf980737w$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf980737w$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1915697$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10563998$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Natella, Fausta</creatorcontrib><creatorcontrib>Nardini, Mirella</creatorcontrib><creatorcontrib>Di Felice, Maurizio</creatorcontrib><creatorcontrib>Scaccini, Cristina</creatorcontrib><title>Benzoic and Cinnamic Acid Derivatives as Antioxidants: Structure−Activity Relation</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>The antioxidant activity of four derivatives of benzoic acid was systematically compared with the activity of the four homologous derivatives of cinnamic acid. The couples of compounds differed for the kind of aromatic substitution (p-hydroxy, p-hydroxymethoxy, p-hydroxydimethoxy, dihydroxy). The antioxidant activity was measured using (i) a competition kinetic test, to measure the relative capacity to quench peroxyl radical and (ii) the in vitro oxidative modification of human low-density lipoprotein (LDL), initiated by 2,2‘-azobis(amidinopropane) dihydrochloride or catalyzed by Cu(II). In both models, cinnamic acids were more efficient than their benzoic counterparts. As for the influence of the aromatic substitution, in the kinetic test the antioxidant activity increased in the sequence p-hydroxy < p-hydroxymethoxy < dihydroxy < p-hydroxydimethoxy. In contrast, in the LDL system, the dihydroxy acids had an antioxidant capacity equal to or higher than that of the p-hydroxydimethoxy acids. Keywords: Benzoic acids; cinnamic acids; antioxidants; low-density lipoprotein</description><subject>2,2'-azobis(amidinopropane) dihydrochloride</subject><subject>Antioxidants</subject><subject>azo compounds</subject><subject>Benzoates - chemistry</subject><subject>Benzoates - pharmacology</subject><subject>benzoic acid</subject><subject>Biological and medical sciences</subject><subject>Cinnamates - chemistry</subject><subject>Cinnamates - pharmacology</subject><subject>cinnamic acid</subject><subject>copper</subject><subject>derivatives</subject><subject>Food additives</subject><subject>Food industries</subject><subject>free radicals</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General aspects</subject><subject>Humans</subject><subject>inhibition</subject><subject>Kinetics</subject><subject>Lipoproteins, LDL - blood</subject><subject>Lipoproteins, LDL - drug effects</subject><subject>Lipoproteins, LDL - metabolism</subject><subject>low density lipoprotein</subject><subject>metal ions</subject><subject>oxidation</subject><subject>peroxyl radicals</subject><subject>reduction</subject><subject>Structure-Activity Relationship</subject><subject>structure-activity relationships</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0Mtu1DAUBmALgehQWPACkAUgsQj4OOMbu2G4SiOBOq0qsbFOHAd5yDjFTkrLiiVsecQ-CR5lVFiwsqzz-bfOT8h9oM-AMni-abWispLfbpAZcEZLDqBukhnNw1JxAQfkTkobSqnikt4mB0C5qLRWM3L60oXvvbcFhqZY-hBwmy8L65vilYv-HAd_7lKBqViEwfcXvsEwpBdXP34V6yGOdhiju_r5e2Gz88NlceS6_KQPd8mtFrvk7u3PQ3Ly5vXx8l25-vD2_XKxKnEu1FDWWgObM9UIJRnnLRO8cnXdWAkKbSU1AwVQs6ylqgEbKnnbUKvkHBtgUB2SJ1PuWey_ji4NZuuTdV2HwfVjMkIzWTFRZfh0gjb2KUXXmrPotxgvDVCza9Fct5jtg33oWG9d84-casvg0R5gsti1EYP16a_TwIWWmZUT82lwF9djjF-MyB9xc_xxbfT6E1serU4Ny_7h5FvsDX6OOfJkzShUlOndErvEx5NAm8ymH2PI5f5ngz9hiZ86</recordid><startdate>19990401</startdate><enddate>19990401</enddate><creator>Natella, Fausta</creator><creator>Nardini, Mirella</creator><creator>Di Felice, Maurizio</creator><creator>Scaccini, Cristina</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><scope>7X8</scope></search><sort><creationdate>19990401</creationdate><title>Benzoic and Cinnamic Acid Derivatives as Antioxidants: Structure−Activity Relation</title><author>Natella, Fausta ; Nardini, Mirella ; Di Felice, Maurizio ; Scaccini, Cristina</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a468t-b9912428d687255f2653ebbdc718ac37921811b2a4678b1ad075fd0c874ad1213</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>2,2'-azobis(amidinopropane) dihydrochloride</topic><topic>Antioxidants</topic><topic>azo compounds</topic><topic>Benzoates - chemistry</topic><topic>Benzoates - pharmacology</topic><topic>benzoic acid</topic><topic>Biological and medical sciences</topic><topic>Cinnamates - chemistry</topic><topic>Cinnamates - pharmacology</topic><topic>cinnamic acid</topic><topic>copper</topic><topic>derivatives</topic><topic>Food additives</topic><topic>Food industries</topic><topic>free radicals</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General aspects</topic><topic>Humans</topic><topic>inhibition</topic><topic>Kinetics</topic><topic>Lipoproteins, LDL - blood</topic><topic>Lipoproteins, LDL - drug effects</topic><topic>Lipoproteins, LDL - metabolism</topic><topic>low density lipoprotein</topic><topic>metal ions</topic><topic>oxidation</topic><topic>peroxyl radicals</topic><topic>reduction</topic><topic>Structure-Activity Relationship</topic><topic>structure-activity relationships</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Natella, Fausta</creatorcontrib><creatorcontrib>Nardini, Mirella</creatorcontrib><creatorcontrib>Di Felice, Maurizio</creatorcontrib><creatorcontrib>Scaccini, Cristina</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><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Natella, Fausta</au><au>Nardini, Mirella</au><au>Di Felice, Maurizio</au><au>Scaccini, Cristina</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Benzoic and Cinnamic Acid Derivatives as Antioxidants: Structure−Activity Relation</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>1999-04-01</date><risdate>1999</risdate><volume>47</volume><issue>4</issue><spage>1453</spage><epage>1459</epage><pages>1453-1459</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>The antioxidant activity of four derivatives of benzoic acid was systematically compared with the activity of the four homologous derivatives of cinnamic acid. The couples of compounds differed for the kind of aromatic substitution (p-hydroxy, p-hydroxymethoxy, p-hydroxydimethoxy, dihydroxy). The antioxidant activity was measured using (i) a competition kinetic test, to measure the relative capacity to quench peroxyl radical and (ii) the in vitro oxidative modification of human low-density lipoprotein (LDL), initiated by 2,2‘-azobis(amidinopropane) dihydrochloride or catalyzed by Cu(II). In both models, cinnamic acids were more efficient than their benzoic counterparts. As for the influence of the aromatic substitution, in the kinetic test the antioxidant activity increased in the sequence p-hydroxy < p-hydroxymethoxy < dihydroxy < p-hydroxydimethoxy. In contrast, in the LDL system, the dihydroxy acids had an antioxidant capacity equal to or higher than that of the p-hydroxydimethoxy acids. Keywords: Benzoic acids; cinnamic acids; antioxidants; low-density lipoprotein</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>10563998</pmid><doi>10.1021/jf980737w</doi><tpages>7</tpages></addata></record> |
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| ispartof | Journal of agricultural and food chemistry, 1999-04, Vol.47 (4), p.1453-1459 |
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| subjects | 2,2'-azobis(amidinopropane) dihydrochloride Antioxidants azo compounds Benzoates - chemistry Benzoates - pharmacology benzoic acid Biological and medical sciences Cinnamates - chemistry Cinnamates - pharmacology cinnamic acid copper derivatives Food additives Food industries free radicals Fundamental and applied biological sciences. Psychology General aspects Humans inhibition Kinetics Lipoproteins, LDL - blood Lipoproteins, LDL - drug effects Lipoproteins, LDL - metabolism low density lipoprotein metal ions oxidation peroxyl radicals reduction Structure-Activity Relationship structure-activity relationships |
| title | Benzoic and Cinnamic Acid Derivatives as Antioxidants: Structure−Activity Relation |
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