The stereochemical configuration of flavanols influences the level and metabolism of flavanols in humans and their biological activity in vivo
Extensive epidemiological and clinical evidence associates diets high in flavanol-containing foods with cardiovascular health benefits in humans. Catechin and epicatechin, the most common flavanols in foods, are present in the diet in different enantiomeric forms. This study investigated the influen...
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| Veröffentlicht in: | Free radical biology & medicine 2011-01, Vol.50 (2), p.237-244 |
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| creator | Ottaviani, Javier I. Momma, Tony Y. Heiss, Christian Kwik-Uribe, Catherine Schroeter, Hagen Keen, Carl L. |
| description | Extensive epidemiological and clinical evidence associates diets high in flavanol-containing foods with cardiovascular health benefits in humans. Catechin and epicatechin, the most common flavanols in foods, are present in the diet in different enantiomeric forms. This study investigated the influence of the stereochemical configuration of flavanols on their absorption, metabolism, and biological activity. Healthy adult males were asked to consume equal amounts of the stereochemically pure flavanols (−)epicatechin, (−)catechin, (+)catechin, and (+)epicatechin (1.5
mg/kg bw) in a well-defined cocoa-based, dairy-containing drink matrix, and flavanol levels were subsequently determined in plasma and 24-h urine. The results obtained show that the stereochemical configuration of flavanols has a profound influence on their uptake and metabolism in humans. In addition, we assessed the vasodilatory activity of each flavanol stereoisomer in vivo and found (−)-epicatechin to be the single stereoisomer capable of mediating a significant arterial dilation response. Importantly, this effect was independent of the classic antioxidant properties of flavanols. Overall, these results indicate that the proposed beneficial health effects associated with the consumption of flavanol-containing foods will significantly depend on the stereochemical configuration of the flavanols ingested. |
| doi_str_mv | 10.1016/j.freeradbiomed.2010.11.005 |
| format | Article |
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mg/kg bw) in a well-defined cocoa-based, dairy-containing drink matrix, and flavanol levels were subsequently determined in plasma and 24-h urine. The results obtained show that the stereochemical configuration of flavanols has a profound influence on their uptake and metabolism in humans. In addition, we assessed the vasodilatory activity of each flavanol stereoisomer in vivo and found (−)-epicatechin to be the single stereoisomer capable of mediating a significant arterial dilation response. Importantly, this effect was independent of the classic antioxidant properties of flavanols. Overall, these results indicate that the proposed beneficial health effects associated with the consumption of flavanol-containing foods will significantly depend on the stereochemical configuration of the flavanols ingested.</description><identifier>ISSN: 0891-5849</identifier><identifier>EISSN: 1873-4596</identifier><identifier>DOI: 10.1016/j.freeradbiomed.2010.11.005</identifier><identifier>PMID: 21074608</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>absorption ; Adolescent ; Adult ; adults ; Animals ; Antioxidant ; antioxidant activity ; Cacao - chemistry ; catechin ; Catechin - blood ; Catechin - chemistry ; Catechin - pharmacology ; Catechin - urine ; Catechol O-Methyltransferase - metabolism ; Chromatography, High Pressure Liquid ; Cross-Over Studies ; diet ; Epicatechin ; Femoral Artery - drug effects ; Flavanols ; foods ; Free radicals ; Humans ; Male ; males ; metabolism ; Polyphenols ; Rats ; Rats, Sprague-Dawley ; Reactive Oxygen Species - metabolism ; Stereoisomerism ; stereoisomers ; urine ; Vasodilator Agents - blood ; Vasodilator Agents - pharmacology ; Vasodilator Agents - urine ; Young Adult</subject><ispartof>Free radical biology & medicine, 2011-01, Vol.50 (2), p.237-244</ispartof><rights>2010 Elsevier Inc.</rights><rights>Copyright © 2010 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c438t-947cf46e55408529a99496d889ca622e1b9ae4549c8b45cc34c9f03254ce9eb83</citedby><cites>FETCH-LOGICAL-c438t-947cf46e55408529a99496d889ca622e1b9ae4549c8b45cc34c9f03254ce9eb83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0891584910013596$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21074608$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ottaviani, Javier I.</creatorcontrib><creatorcontrib>Momma, Tony Y.</creatorcontrib><creatorcontrib>Heiss, Christian</creatorcontrib><creatorcontrib>Kwik-Uribe, Catherine</creatorcontrib><creatorcontrib>Schroeter, Hagen</creatorcontrib><creatorcontrib>Keen, Carl L.</creatorcontrib><title>The stereochemical configuration of flavanols influences the level and metabolism of flavanols in humans and their biological activity in vivo</title><title>Free radical biology & medicine</title><addtitle>Free Radic Biol Med</addtitle><description>Extensive epidemiological and clinical evidence associates diets high in flavanol-containing foods with cardiovascular health benefits in humans. Catechin and epicatechin, the most common flavanols in foods, are present in the diet in different enantiomeric forms. This study investigated the influence of the stereochemical configuration of flavanols on their absorption, metabolism, and biological activity. Healthy adult males were asked to consume equal amounts of the stereochemically pure flavanols (−)epicatechin, (−)catechin, (+)catechin, and (+)epicatechin (1.5
mg/kg bw) in a well-defined cocoa-based, dairy-containing drink matrix, and flavanol levels were subsequently determined in plasma and 24-h urine. The results obtained show that the stereochemical configuration of flavanols has a profound influence on their uptake and metabolism in humans. In addition, we assessed the vasodilatory activity of each flavanol stereoisomer in vivo and found (−)-epicatechin to be the single stereoisomer capable of mediating a significant arterial dilation response. Importantly, this effect was independent of the classic antioxidant properties of flavanols. Overall, these results indicate that the proposed beneficial health effects associated with the consumption of flavanol-containing foods will significantly depend on the stereochemical configuration of the flavanols ingested.</description><subject>absorption</subject><subject>Adolescent</subject><subject>Adult</subject><subject>adults</subject><subject>Animals</subject><subject>Antioxidant</subject><subject>antioxidant activity</subject><subject>Cacao - chemistry</subject><subject>catechin</subject><subject>Catechin - blood</subject><subject>Catechin - chemistry</subject><subject>Catechin - pharmacology</subject><subject>Catechin - urine</subject><subject>Catechol O-Methyltransferase - metabolism</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Cross-Over Studies</subject><subject>diet</subject><subject>Epicatechin</subject><subject>Femoral Artery - drug effects</subject><subject>Flavanols</subject><subject>foods</subject><subject>Free radicals</subject><subject>Humans</subject><subject>Male</subject><subject>males</subject><subject>metabolism</subject><subject>Polyphenols</subject><subject>Rats</subject><subject>Rats, Sprague-Dawley</subject><subject>Reactive Oxygen Species - metabolism</subject><subject>Stereoisomerism</subject><subject>stereoisomers</subject><subject>urine</subject><subject>Vasodilator Agents - blood</subject><subject>Vasodilator Agents - pharmacology</subject><subject>Vasodilator Agents - urine</subject><subject>Young Adult</subject><issn>0891-5849</issn><issn>1873-4596</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkU1v1DAQhi0EokvhL4AlDpyy2PHH2uKEqvIhVeJAe7YcZ7zrlRMXO4nUP9HfjNNtD3CB0xzmeWdG8yD0npItJVR-PG59Bsi270IaoN-2ZO3QLSHiGdpQtWMNF1o-RxuiNG2E4voMvSrlSAjhgqmX6KylZMclURt0f30AXCbIkNwBhuBsxC6NPuznbKeQRpw89tEudkyx4DD6OMPooOCpBiMsELEdezzAZLsUQxn-DuDDPNixPFA1EzKud8e0f1hl3RSWMN2t3BKW9Bq98DYWePNYz9HNl8vri2_N1Y-v3y8-XzWOMzU1mu-c5xKE4ESJVlutuZa9UtpZ2bZAO22BC66d6rhwjnGnPWGt4A40dIqdow-nubc5_ZqhTGYIxUGMdoQ0F6OlorJlWvyTVExQqqSQlfx0Il1OpWTw5jaHweY7Q4lZzZmj-cOcWc0ZSk01V9NvH_fM3dp7yj6pqsC7E-BtMnafQzE3P-sEQQhlkglSicsTAfVzS4BsigurrD5kcJPpU_ivU34DM8e9iA</recordid><startdate>20110115</startdate><enddate>20110115</enddate><creator>Ottaviani, Javier I.</creator><creator>Momma, Tony Y.</creator><creator>Heiss, Christian</creator><creator>Kwik-Uribe, Catherine</creator><creator>Schroeter, Hagen</creator><creator>Keen, Carl L.</creator><general>Elsevier Inc</general><scope>FBQ</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><scope>7U7</scope><scope>C1K</scope></search><sort><creationdate>20110115</creationdate><title>The stereochemical configuration of flavanols influences the level and metabolism of flavanols in humans and their biological activity in vivo</title><author>Ottaviani, Javier I. ; Momma, Tony Y. ; Heiss, Christian ; Kwik-Uribe, Catherine ; Schroeter, Hagen ; Keen, Carl L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c438t-947cf46e55408529a99496d889ca622e1b9ae4549c8b45cc34c9f03254ce9eb83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>absorption</topic><topic>Adolescent</topic><topic>Adult</topic><topic>adults</topic><topic>Animals</topic><topic>Antioxidant</topic><topic>antioxidant activity</topic><topic>Cacao - chemistry</topic><topic>catechin</topic><topic>Catechin - blood</topic><topic>Catechin - chemistry</topic><topic>Catechin - pharmacology</topic><topic>Catechin - urine</topic><topic>Catechol O-Methyltransferase - metabolism</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Cross-Over Studies</topic><topic>diet</topic><topic>Epicatechin</topic><topic>Femoral Artery - drug effects</topic><topic>Flavanols</topic><topic>foods</topic><topic>Free radicals</topic><topic>Humans</topic><topic>Male</topic><topic>males</topic><topic>metabolism</topic><topic>Polyphenols</topic><topic>Rats</topic><topic>Rats, Sprague-Dawley</topic><topic>Reactive Oxygen Species - metabolism</topic><topic>Stereoisomerism</topic><topic>stereoisomers</topic><topic>urine</topic><topic>Vasodilator Agents - blood</topic><topic>Vasodilator Agents - pharmacology</topic><topic>Vasodilator Agents - urine</topic><topic>Young Adult</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ottaviani, Javier I.</creatorcontrib><creatorcontrib>Momma, Tony Y.</creatorcontrib><creatorcontrib>Heiss, Christian</creatorcontrib><creatorcontrib>Kwik-Uribe, Catherine</creatorcontrib><creatorcontrib>Schroeter, Hagen</creatorcontrib><creatorcontrib>Keen, Carl L.</creatorcontrib><collection>AGRIS</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><collection>Toxicology Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><jtitle>Free radical biology & medicine</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ottaviani, Javier I.</au><au>Momma, Tony Y.</au><au>Heiss, Christian</au><au>Kwik-Uribe, Catherine</au><au>Schroeter, Hagen</au><au>Keen, Carl L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The stereochemical configuration of flavanols influences the level and metabolism of flavanols in humans and their biological activity in vivo</atitle><jtitle>Free radical biology & medicine</jtitle><addtitle>Free Radic Biol Med</addtitle><date>2011-01-15</date><risdate>2011</risdate><volume>50</volume><issue>2</issue><spage>237</spage><epage>244</epage><pages>237-244</pages><issn>0891-5849</issn><eissn>1873-4596</eissn><abstract>Extensive epidemiological and clinical evidence associates diets high in flavanol-containing foods with cardiovascular health benefits in humans. Catechin and epicatechin, the most common flavanols in foods, are present in the diet in different enantiomeric forms. This study investigated the influence of the stereochemical configuration of flavanols on their absorption, metabolism, and biological activity. Healthy adult males were asked to consume equal amounts of the stereochemically pure flavanols (−)epicatechin, (−)catechin, (+)catechin, and (+)epicatechin (1.5
mg/kg bw) in a well-defined cocoa-based, dairy-containing drink matrix, and flavanol levels were subsequently determined in plasma and 24-h urine. The results obtained show that the stereochemical configuration of flavanols has a profound influence on their uptake and metabolism in humans. In addition, we assessed the vasodilatory activity of each flavanol stereoisomer in vivo and found (−)-epicatechin to be the single stereoisomer capable of mediating a significant arterial dilation response. Importantly, this effect was independent of the classic antioxidant properties of flavanols. Overall, these results indicate that the proposed beneficial health effects associated with the consumption of flavanol-containing foods will significantly depend on the stereochemical configuration of the flavanols ingested.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>21074608</pmid><doi>10.1016/j.freeradbiomed.2010.11.005</doi><tpages>8</tpages></addata></record> |
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| subjects | absorption Adolescent Adult adults Animals Antioxidant antioxidant activity Cacao - chemistry catechin Catechin - blood Catechin - chemistry Catechin - pharmacology Catechin - urine Catechol O-Methyltransferase - metabolism Chromatography, High Pressure Liquid Cross-Over Studies diet Epicatechin Femoral Artery - drug effects Flavanols foods Free radicals Humans Male males metabolism Polyphenols Rats Rats, Sprague-Dawley Reactive Oxygen Species - metabolism Stereoisomerism stereoisomers urine Vasodilator Agents - blood Vasodilator Agents - pharmacology Vasodilator Agents - urine Young Adult |
| title | The stereochemical configuration of flavanols influences the level and metabolism of flavanols in humans and their biological activity in vivo |
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