Antioxidant and Membrane Effects of Procyanidin Dimers and Trimers Isolated from Peanut and Cocoa
The antioxidant and membrane effects of dimer (Dim) and trimer (Trim) procyanidins isolated from cocoa (Theobroma cacao) (B- and C-bonded) and peanut (Arachis hypogea L.) skin (A-bonded) were evaluated in phosphatidyl choline liposomes. When liposomes were oxidized with a steady source of oxidants,...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2005-06, Vol.53 (12), p.5041-5048 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Verstraeten, Sandra V Hammerstone, John F Keen, Carl L Fraga, César G Oteiza, Patricia I |
| description | The antioxidant and membrane effects of dimer (Dim) and trimer (Trim) procyanidins isolated from cocoa (Theobroma cacao) (B- and C-bonded) and peanut (Arachis hypogea L.) skin (A-bonded) were evaluated in phosphatidyl choline liposomes. When liposomes were oxidized with a steady source of oxidants, the above dimers and trimers inhibited to a similar extent lipid oxidation in a concentration (0.33−5 μM)-dependent manner. With respect to membrane effects, Dim A1, Dim B, Trim A, and Trim C increased (Dim A1 = Dim B and Trim A = Trim C), while Dim A2 decreased, membrane surface potential. All of the procyanidins tested decreased membrane fluidity as determined by fluorescent probes at the water−lipid interface, an effect that extended into the hydrophobic region of the bilayer. Both dimers and trimers protected the lipid bilayer from disruption by Triton X-100. The magnitude of the protection was Dim A1 > Dim A2 > Dim B and Trim C > Trim A. Thus, dimers and trimers can interact with membrane phospholipids, presumably with their polar headgroup. As a consequence of this interaction, they can provide protection against the attack of oxidants and other molecules that challenge the integrity of the bilayer. Keywords: Flavonoids; polyphenols; procyanidins; antioxidants; lipid oxidation; membrane interactions; Theobroma cacao; Arachis hypogea L. |
| doi_str_mv | 10.1021/jf058018m |
| format | Article |
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When liposomes were oxidized with a steady source of oxidants, the above dimers and trimers inhibited to a similar extent lipid oxidation in a concentration (0.33−5 μM)-dependent manner. With respect to membrane effects, Dim A1, Dim B, Trim A, and Trim C increased (Dim A1 = Dim B and Trim A = Trim C), while Dim A2 decreased, membrane surface potential. All of the procyanidins tested decreased membrane fluidity as determined by fluorescent probes at the water−lipid interface, an effect that extended into the hydrophobic region of the bilayer. Both dimers and trimers protected the lipid bilayer from disruption by Triton X-100. The magnitude of the protection was Dim A1 > Dim A2 > Dim B and Trim C > Trim A. Thus, dimers and trimers can interact with membrane phospholipids, presumably with their polar headgroup. As a consequence of this interaction, they can provide protection against the attack of oxidants and other molecules that challenge the integrity of the bilayer. Keywords: Flavonoids; polyphenols; procyanidins; antioxidants; lipid oxidation; membrane interactions; Theobroma cacao; Arachis hypogea L.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf058018m</identifier><identifier>PMID: 15941354</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>antioxidant activity ; Antioxidants - chemistry ; Antioxidants - isolation & purification ; Antioxidants - pharmacology ; Arachis - chemistry ; Biological and medical sciences ; Cacao - chemistry ; Cell Membrane - drug effects ; cocoa beans ; dimer procyanidins ; Dimerization ; Food industries ; Fundamental and applied biological sciences. Psychology ; Lipid Bilayers ; Lipid Peroxidation - drug effects ; liposomes (artificial) ; Liposomes - chemistry ; membrane fluidity ; Membrane Fluidity - drug effects ; membrane potential ; Oxidation-Reduction ; peanuts ; phosphatidylcholines ; Proanthocyanidins - chemistry ; Proanthocyanidins - isolation & purification ; Proanthocyanidins - pharmacology ; procyanidins ; Seeds - chemistry ; trimer procyanidins</subject><ispartof>Journal of agricultural and food chemistry, 2005-06, Vol.53 (12), p.5041-5048</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a471t-dfe1fc494de15c8c259d9f5306f11a5cb6d3307a2a4164de61b53ae3bd1f7923</citedby><cites>FETCH-LOGICAL-a471t-dfe1fc494de15c8c259d9f5306f11a5cb6d3307a2a4164de61b53ae3bd1f7923</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/jf058018m$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf058018m$$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=16855399$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15941354$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Verstraeten, Sandra V</creatorcontrib><creatorcontrib>Hammerstone, John F</creatorcontrib><creatorcontrib>Keen, Carl L</creatorcontrib><creatorcontrib>Fraga, César G</creatorcontrib><creatorcontrib>Oteiza, Patricia I</creatorcontrib><title>Antioxidant and Membrane Effects of Procyanidin Dimers and Trimers Isolated from Peanut and Cocoa</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>The antioxidant and membrane effects of dimer (Dim) and trimer (Trim) procyanidins isolated from cocoa (Theobroma cacao) (B- and C-bonded) and peanut (Arachis hypogea L.) skin (A-bonded) were evaluated in phosphatidyl choline liposomes. When liposomes were oxidized with a steady source of oxidants, the above dimers and trimers inhibited to a similar extent lipid oxidation in a concentration (0.33−5 μM)-dependent manner. With respect to membrane effects, Dim A1, Dim B, Trim A, and Trim C increased (Dim A1 = Dim B and Trim A = Trim C), while Dim A2 decreased, membrane surface potential. All of the procyanidins tested decreased membrane fluidity as determined by fluorescent probes at the water−lipid interface, an effect that extended into the hydrophobic region of the bilayer. Both dimers and trimers protected the lipid bilayer from disruption by Triton X-100. The magnitude of the protection was Dim A1 > Dim A2 > Dim B and Trim C > Trim A. Thus, dimers and trimers can interact with membrane phospholipids, presumably with their polar headgroup. As a consequence of this interaction, they can provide protection against the attack of oxidants and other molecules that challenge the integrity of the bilayer. Keywords: Flavonoids; polyphenols; procyanidins; antioxidants; lipid oxidation; membrane interactions; Theobroma cacao; Arachis hypogea L.</description><subject>antioxidant activity</subject><subject>Antioxidants - chemistry</subject><subject>Antioxidants - isolation & purification</subject><subject>Antioxidants - pharmacology</subject><subject>Arachis - chemistry</subject><subject>Biological and medical sciences</subject><subject>Cacao - chemistry</subject><subject>Cell Membrane - drug effects</subject><subject>cocoa beans</subject><subject>dimer procyanidins</subject><subject>Dimerization</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Lipid Bilayers</subject><subject>Lipid Peroxidation - drug effects</subject><subject>liposomes (artificial)</subject><subject>Liposomes - chemistry</subject><subject>membrane fluidity</subject><subject>Membrane Fluidity - drug effects</subject><subject>membrane potential</subject><subject>Oxidation-Reduction</subject><subject>peanuts</subject><subject>phosphatidylcholines</subject><subject>Proanthocyanidins - chemistry</subject><subject>Proanthocyanidins - isolation & purification</subject><subject>Proanthocyanidins - pharmacology</subject><subject>procyanidins</subject><subject>Seeds - chemistry</subject><subject>trimer procyanidins</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1v1DAQBmALgehSOPAHIBeQOARm4jhxjtVSaKUiVt0FjtbEHyhLErd2IrX_HpesuhdOtjSPXntexl4jfEQo8NPegZCAcnjCVigKyAWifMpWkIa5FBWesBcx7gFAihqesxMUTYlclCtGZ-PU-bvO0DhlNJrsmx3aQKPNzp2zeoqZd9kmeH1PY2e6MfvcDTbEf3QXlvtl9D1N1mQu-CHbWBrnJWvttaeX7JmjPtpXh_OU7b6c79YX-dX3r5frs6ucyhqn3DiLTpdNaSwKLXUhGtM4waFyiCR0WxnOoaaCSqwSqrAVnCxvDbq6Kfgpe7_E3gR_O9s4qaGL2vZ92sXPUVV1k0rhD_DDAnXwMQbr1E3ag8K9QlAPdarHOpN9cwid28Gaozz0l8C7A6CoqXepOd3Fo6ukELxpkssX18XJ3j3OKfxJH-O1ULvNVm1_yevyZ3WtLpJ_u3hHXtHvkDJ_bAtADghQ1yCPL5OOau_nMKZy_7PCX_aXoSw</recordid><startdate>20050615</startdate><enddate>20050615</enddate><creator>Verstraeten, Sandra V</creator><creator>Hammerstone, John F</creator><creator>Keen, Carl L</creator><creator>Fraga, César G</creator><creator>Oteiza, Patricia I</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>20050615</creationdate><title>Antioxidant and Membrane Effects of Procyanidin Dimers and Trimers Isolated from Peanut and Cocoa</title><author>Verstraeten, Sandra V ; Hammerstone, John F ; Keen, Carl L ; Fraga, César G ; Oteiza, Patricia I</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a471t-dfe1fc494de15c8c259d9f5306f11a5cb6d3307a2a4164de61b53ae3bd1f7923</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>antioxidant activity</topic><topic>Antioxidants - chemistry</topic><topic>Antioxidants - isolation & purification</topic><topic>Antioxidants - pharmacology</topic><topic>Arachis - chemistry</topic><topic>Biological and medical sciences</topic><topic>Cacao - chemistry</topic><topic>Cell Membrane - drug effects</topic><topic>cocoa beans</topic><topic>dimer procyanidins</topic><topic>Dimerization</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Lipid Bilayers</topic><topic>Lipid Peroxidation - drug effects</topic><topic>liposomes (artificial)</topic><topic>Liposomes - chemistry</topic><topic>membrane fluidity</topic><topic>Membrane Fluidity - drug effects</topic><topic>membrane potential</topic><topic>Oxidation-Reduction</topic><topic>peanuts</topic><topic>phosphatidylcholines</topic><topic>Proanthocyanidins - chemistry</topic><topic>Proanthocyanidins - isolation & purification</topic><topic>Proanthocyanidins - pharmacology</topic><topic>procyanidins</topic><topic>Seeds - chemistry</topic><topic>trimer procyanidins</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Verstraeten, Sandra V</creatorcontrib><creatorcontrib>Hammerstone, John F</creatorcontrib><creatorcontrib>Keen, Carl L</creatorcontrib><creatorcontrib>Fraga, César G</creatorcontrib><creatorcontrib>Oteiza, Patricia I</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>Verstraeten, Sandra V</au><au>Hammerstone, John F</au><au>Keen, Carl L</au><au>Fraga, César G</au><au>Oteiza, Patricia I</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antioxidant and Membrane Effects of Procyanidin Dimers and Trimers Isolated from Peanut and Cocoa</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2005-06-15</date><risdate>2005</risdate><volume>53</volume><issue>12</issue><spage>5041</spage><epage>5048</epage><pages>5041-5048</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>The antioxidant and membrane effects of dimer (Dim) and trimer (Trim) procyanidins isolated from cocoa (Theobroma cacao) (B- and C-bonded) and peanut (Arachis hypogea L.) skin (A-bonded) were evaluated in phosphatidyl choline liposomes. When liposomes were oxidized with a steady source of oxidants, the above dimers and trimers inhibited to a similar extent lipid oxidation in a concentration (0.33−5 μM)-dependent manner. With respect to membrane effects, Dim A1, Dim B, Trim A, and Trim C increased (Dim A1 = Dim B and Trim A = Trim C), while Dim A2 decreased, membrane surface potential. All of the procyanidins tested decreased membrane fluidity as determined by fluorescent probes at the water−lipid interface, an effect that extended into the hydrophobic region of the bilayer. Both dimers and trimers protected the lipid bilayer from disruption by Triton X-100. The magnitude of the protection was Dim A1 > Dim A2 > Dim B and Trim C > Trim A. Thus, dimers and trimers can interact with membrane phospholipids, presumably with their polar headgroup. As a consequence of this interaction, they can provide protection against the attack of oxidants and other molecules that challenge the integrity of the bilayer. Keywords: Flavonoids; polyphenols; procyanidins; antioxidants; lipid oxidation; membrane interactions; Theobroma cacao; Arachis hypogea L.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15941354</pmid><doi>10.1021/jf058018m</doi><tpages>8</tpages></addata></record> |
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| subjects | antioxidant activity Antioxidants - chemistry Antioxidants - isolation & purification Antioxidants - pharmacology Arachis - chemistry Biological and medical sciences Cacao - chemistry Cell Membrane - drug effects cocoa beans dimer procyanidins Dimerization Food industries Fundamental and applied biological sciences. Psychology Lipid Bilayers Lipid Peroxidation - drug effects liposomes (artificial) Liposomes - chemistry membrane fluidity Membrane Fluidity - drug effects membrane potential Oxidation-Reduction peanuts phosphatidylcholines Proanthocyanidins - chemistry Proanthocyanidins - isolation & purification Proanthocyanidins - pharmacology procyanidins Seeds - chemistry trimer procyanidins |
| title | Antioxidant and Membrane Effects of Procyanidin Dimers and Trimers Isolated from Peanut and Cocoa |
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