Metabolic Fate of Luteolin in Rats: Its Relationship to Anti-inflammatory Effect
Luteolin is a naturally occurring flavone that reportedly has anti-inflammatory effects. Because most luteolin is conjugated following intestinal absorption, free luteolin is likely present at low levels in the body. Therefore, luteolin metabolites are presumably responsible for luteolin bioactivity...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2016-06, Vol.64 (21), p.4246-4254 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Kure, Ayako Nakagawa, Kiyotaka Kondo, Momoko Kato, Shunji Kimura, Fumiko Watanabe, Akio Shoji, Naoki Hatanaka, Sakiko Tsushida, Tojiro Miyazawa, Teruo |
| description | Luteolin is a naturally occurring flavone that reportedly has anti-inflammatory effects. Because most luteolin is conjugated following intestinal absorption, free luteolin is likely present at low levels in the body. Therefore, luteolin metabolites are presumably responsible for luteolin bioactivity. Here we confirmed that luteolin glucuronides, especially luteolin-3′-O-glucuronide, are the major metabolites found in plasma after oral administration of luteolin (aglycone) or luteolin glucoside (luteolin-7-O-glucoside) to rats. Luteolin-4′-O-glucuronide and luteolin-7-O-glucuronide were also detectable together with luteolin-3′-O-glucuronide in the liver, kidney, and small intestine. Next, we prepared these luteolin glucuronides and compared the anti-inflammatory effects of luteolin and luteolin glucuronides on gene expression in lipopolysaccharide-treated RAW264.7 cells. Luteolin glucuronides, especially luteolin-7-O-glucuronide, reduced expression of inflammatory genes in the cells, although their effects were weaker than those of luteolin. These results indicate that the active compound responsible for the anti-inflammatory effect of luteolin in vivo would be luteolin glucuronide and/or residual luteolin. |
| doi_str_mv | 10.1021/acs.jafc.6b00964 |
| format | Article |
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Because most luteolin is conjugated following intestinal absorption, free luteolin is likely present at low levels in the body. Therefore, luteolin metabolites are presumably responsible for luteolin bioactivity. Here we confirmed that luteolin glucuronides, especially luteolin-3′-O-glucuronide, are the major metabolites found in plasma after oral administration of luteolin (aglycone) or luteolin glucoside (luteolin-7-O-glucoside) to rats. Luteolin-4′-O-glucuronide and luteolin-7-O-glucuronide were also detectable together with luteolin-3′-O-glucuronide in the liver, kidney, and small intestine. Next, we prepared these luteolin glucuronides and compared the anti-inflammatory effects of luteolin and luteolin glucuronides on gene expression in lipopolysaccharide-treated RAW264.7 cells. Luteolin glucuronides, especially luteolin-7-O-glucuronide, reduced expression of inflammatory genes in the cells, although their effects were weaker than those of luteolin. These results indicate that the active compound responsible for the anti-inflammatory effect of luteolin in vivo would be luteolin glucuronide and/or residual luteolin.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/acs.jafc.6b00964</identifier><identifier>PMID: 27170112</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Anti-Inflammatory Agents - chemistry ; Anti-Inflammatory Agents - metabolism ; Anti-Inflammatory Agents - pharmacology ; Intestinal Absorption - drug effects ; Intestine, Small - metabolism ; Kidney - metabolism ; Liver - metabolism ; Luteolin - chemistry ; Luteolin - metabolism ; Luteolin - pharmacology ; Macrophages - drug effects ; Macrophages - immunology ; Male ; Mice ; Molecular Structure ; Rats ; Rats, Sprague-Dawley ; RAW 264.7 Cells</subject><ispartof>Journal of agricultural and food chemistry, 2016-06, Vol.64 (21), p.4246-4254</ispartof><rights>Copyright © 2016 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a402t-2637fdca96eea5b8294aaca061f15f2b64a7e01fde8281f1666a7b8e70138bb3</citedby><cites>FETCH-LOGICAL-a402t-2637fdca96eea5b8294aaca061f15f2b64a7e01fde8281f1666a7b8e70138bb3</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/acs.jafc.6b00964$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jafc.6b00964$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27170112$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kure, Ayako</creatorcontrib><creatorcontrib>Nakagawa, Kiyotaka</creatorcontrib><creatorcontrib>Kondo, Momoko</creatorcontrib><creatorcontrib>Kato, Shunji</creatorcontrib><creatorcontrib>Kimura, Fumiko</creatorcontrib><creatorcontrib>Watanabe, Akio</creatorcontrib><creatorcontrib>Shoji, Naoki</creatorcontrib><creatorcontrib>Hatanaka, Sakiko</creatorcontrib><creatorcontrib>Tsushida, Tojiro</creatorcontrib><creatorcontrib>Miyazawa, Teruo</creatorcontrib><title>Metabolic Fate of Luteolin in Rats: Its Relationship to Anti-inflammatory Effect</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Luteolin is a naturally occurring flavone that reportedly has anti-inflammatory effects. Because most luteolin is conjugated following intestinal absorption, free luteolin is likely present at low levels in the body. Therefore, luteolin metabolites are presumably responsible for luteolin bioactivity. Here we confirmed that luteolin glucuronides, especially luteolin-3′-O-glucuronide, are the major metabolites found in plasma after oral administration of luteolin (aglycone) or luteolin glucoside (luteolin-7-O-glucoside) to rats. Luteolin-4′-O-glucuronide and luteolin-7-O-glucuronide were also detectable together with luteolin-3′-O-glucuronide in the liver, kidney, and small intestine. Next, we prepared these luteolin glucuronides and compared the anti-inflammatory effects of luteolin and luteolin glucuronides on gene expression in lipopolysaccharide-treated RAW264.7 cells. Luteolin glucuronides, especially luteolin-7-O-glucuronide, reduced expression of inflammatory genes in the cells, although their effects were weaker than those of luteolin. These results indicate that the active compound responsible for the anti-inflammatory effect of luteolin in vivo would be luteolin glucuronide and/or residual luteolin.</description><subject>Animals</subject><subject>Anti-Inflammatory Agents - chemistry</subject><subject>Anti-Inflammatory Agents - metabolism</subject><subject>Anti-Inflammatory Agents - pharmacology</subject><subject>Intestinal Absorption - drug effects</subject><subject>Intestine, Small - metabolism</subject><subject>Kidney - metabolism</subject><subject>Liver - metabolism</subject><subject>Luteolin - chemistry</subject><subject>Luteolin - metabolism</subject><subject>Luteolin - pharmacology</subject><subject>Macrophages - drug effects</subject><subject>Macrophages - immunology</subject><subject>Male</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Rats</subject><subject>Rats, Sprague-Dawley</subject><subject>RAW 264.7 Cells</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kMFLwzAUh4Mobk7vniRHD3a-pG2aeZOx6WCijN3DS5dgR9vMJj3svzdz05sQEnh8vx8vHyG3DMYMOHvE0o-3aMux0AATkZ2RIcs5JDlj8pwMITKJzAUbkCvvtwAg8wIuyYAXrADG-JB8vJmA2tVVSecYDHWWLvtg4qCl8aww-Ce6CJ6uTI2hcq3_rHY0OPrchiqpWltj02Bw3Z7OrDVluCYXFmtvbk7viKzns_X0NVm-vyymz8sEM-Ah4SIt7KbEiTAGcy35JEMsEQSzLLdciwwLA8xujOQyzoQQWGhp4tqp1Dodkftj7a5zX73xQTWVL01dY2tc7xUrJmku4pVFFI5o2TnvO2PVrqsa7PaKgTpoVFGjOmhUJ40xcndq73VjNn-BX28ReDgCP1HXd2386_9931hfffc</recordid><startdate>20160601</startdate><enddate>20160601</enddate><creator>Kure, Ayako</creator><creator>Nakagawa, Kiyotaka</creator><creator>Kondo, Momoko</creator><creator>Kato, Shunji</creator><creator>Kimura, Fumiko</creator><creator>Watanabe, Akio</creator><creator>Shoji, Naoki</creator><creator>Hatanaka, Sakiko</creator><creator>Tsushida, Tojiro</creator><creator>Miyazawa, Teruo</creator><general>American Chemical Society</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></search><sort><creationdate>20160601</creationdate><title>Metabolic Fate of Luteolin in Rats: Its Relationship to Anti-inflammatory Effect</title><author>Kure, Ayako ; Nakagawa, Kiyotaka ; Kondo, Momoko ; Kato, Shunji ; Kimura, Fumiko ; Watanabe, Akio ; Shoji, Naoki ; Hatanaka, Sakiko ; Tsushida, Tojiro ; Miyazawa, Teruo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a402t-2637fdca96eea5b8294aaca061f15f2b64a7e01fde8281f1666a7b8e70138bb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Animals</topic><topic>Anti-Inflammatory Agents - chemistry</topic><topic>Anti-Inflammatory Agents - metabolism</topic><topic>Anti-Inflammatory Agents - pharmacology</topic><topic>Intestinal Absorption - drug effects</topic><topic>Intestine, Small - metabolism</topic><topic>Kidney - metabolism</topic><topic>Liver - metabolism</topic><topic>Luteolin - chemistry</topic><topic>Luteolin - metabolism</topic><topic>Luteolin - pharmacology</topic><topic>Macrophages - drug effects</topic><topic>Macrophages - immunology</topic><topic>Male</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>Rats</topic><topic>Rats, Sprague-Dawley</topic><topic>RAW 264.7 Cells</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kure, Ayako</creatorcontrib><creatorcontrib>Nakagawa, Kiyotaka</creatorcontrib><creatorcontrib>Kondo, Momoko</creatorcontrib><creatorcontrib>Kato, Shunji</creatorcontrib><creatorcontrib>Kimura, Fumiko</creatorcontrib><creatorcontrib>Watanabe, Akio</creatorcontrib><creatorcontrib>Shoji, Naoki</creatorcontrib><creatorcontrib>Hatanaka, Sakiko</creatorcontrib><creatorcontrib>Tsushida, Tojiro</creatorcontrib><creatorcontrib>Miyazawa, Teruo</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><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kure, Ayako</au><au>Nakagawa, Kiyotaka</au><au>Kondo, Momoko</au><au>Kato, Shunji</au><au>Kimura, Fumiko</au><au>Watanabe, Akio</au><au>Shoji, Naoki</au><au>Hatanaka, Sakiko</au><au>Tsushida, Tojiro</au><au>Miyazawa, Teruo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metabolic Fate of Luteolin in Rats: Its Relationship to Anti-inflammatory Effect</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2016-06-01</date><risdate>2016</risdate><volume>64</volume><issue>21</issue><spage>4246</spage><epage>4254</epage><pages>4246-4254</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><abstract>Luteolin is a naturally occurring flavone that reportedly has anti-inflammatory effects. Because most luteolin is conjugated following intestinal absorption, free luteolin is likely present at low levels in the body. Therefore, luteolin metabolites are presumably responsible for luteolin bioactivity. Here we confirmed that luteolin glucuronides, especially luteolin-3′-O-glucuronide, are the major metabolites found in plasma after oral administration of luteolin (aglycone) or luteolin glucoside (luteolin-7-O-glucoside) to rats. Luteolin-4′-O-glucuronide and luteolin-7-O-glucuronide were also detectable together with luteolin-3′-O-glucuronide in the liver, kidney, and small intestine. Next, we prepared these luteolin glucuronides and compared the anti-inflammatory effects of luteolin and luteolin glucuronides on gene expression in lipopolysaccharide-treated RAW264.7 cells. Luteolin glucuronides, especially luteolin-7-O-glucuronide, reduced expression of inflammatory genes in the cells, although their effects were weaker than those of luteolin. These results indicate that the active compound responsible for the anti-inflammatory effect of luteolin in vivo would be luteolin glucuronide and/or residual luteolin.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>27170112</pmid><doi>10.1021/acs.jafc.6b00964</doi><tpages>9</tpages></addata></record> |
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| subjects | Animals Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - metabolism Anti-Inflammatory Agents - pharmacology Intestinal Absorption - drug effects Intestine, Small - metabolism Kidney - metabolism Liver - metabolism Luteolin - chemistry Luteolin - metabolism Luteolin - pharmacology Macrophages - drug effects Macrophages - immunology Male Mice Molecular Structure Rats Rats, Sprague-Dawley RAW 264.7 Cells |
| title | Metabolic Fate of Luteolin in Rats: Its Relationship to Anti-inflammatory Effect |
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