In Vitro Metabolism of Plant Lignans: New Precursors of Mammalian Lignans Enterolactone and Enterodiol
The metabolism of the plant lignans matairesinol, secoisolariciresinol, pinoresinol, syringaresinol, arctigenin, 7-hydroxymatairesinol, isolariciresinol, and lariciresinol by human fecal microflora was investigated to study their properties as mammalian lignan precursors. The quantitative analyses o...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2001-07, Vol.49 (7), p.3178-3186 |
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| container_title | Journal of agricultural and food chemistry |
| container_volume | 49 |
| creator | Heinonen, Satu Nurmi, Tarja Liukkonen, Kirsi Poutanen, Kaisa Wähälä, Kristiina Deyama, Takeshi Nishibe, Sansei Adlercreutz, Herman |
| description | The metabolism of the plant lignans matairesinol, secoisolariciresinol, pinoresinol, syringaresinol, arctigenin, 7-hydroxymatairesinol, isolariciresinol, and lariciresinol by human fecal microflora was investigated to study their properties as mammalian lignan precursors. The quantitative analyses of lignan precursors and the mammalian lignans enterolactone and enterodiol were performed by HPLC with coulometric electrode array detector. The metabolic products, including mammalian lignans, were characterized as trimethylsilyl derivatives by gas chromatography−mass spectrometry. Matairesinol, secoisolariciresinol, lariciresinol, and pinoresinol were converted to mammalian lignans only. Several metabolites were isolated and tentatively identified as for syringaresinol and arctigenin in addition to the mammalian lignans. Metabolites of 7-hydroxymatairesinol were characterized as enterolactone and 7-hydroxyenterolactone by comparison with authentic reference compounds. A metabolic scheme describing the conversion of the most abundant new mammalian lignan precursors, pinoresinol and lariciresinol, is presented. Keywords: Phytoestrogens; lignans; matairesinol; secoisolariciresinol; lariciresinol; pinoresinol; syringaresinol; isolariciresinol; arctigenin; 7-hydroxymatairesinol; mammalian lignans; enterolactone; enterodiol |
| doi_str_mv | 10.1021/jf010038a |
| format | Article |
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The quantitative analyses of lignan precursors and the mammalian lignans enterolactone and enterodiol were performed by HPLC with coulometric electrode array detector. The metabolic products, including mammalian lignans, were characterized as trimethylsilyl derivatives by gas chromatography−mass spectrometry. Matairesinol, secoisolariciresinol, lariciresinol, and pinoresinol were converted to mammalian lignans only. Several metabolites were isolated and tentatively identified as for syringaresinol and arctigenin in addition to the mammalian lignans. Metabolites of 7-hydroxymatairesinol were characterized as enterolactone and 7-hydroxyenterolactone by comparison with authentic reference compounds. A metabolic scheme describing the conversion of the most abundant new mammalian lignan precursors, pinoresinol and lariciresinol, is presented. Keywords: Phytoestrogens; lignans; matairesinol; secoisolariciresinol; lariciresinol; pinoresinol; syringaresinol; isolariciresinol; arctigenin; 7-hydroxymatairesinol; mammalian lignans; enterolactone; enterodiol</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf010038a</identifier><identifier>PMID: 11453749</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>4-Butyrolactone - analogs & derivatives ; 4-Butyrolactone - metabolism ; Biological and medical sciences ; Chromatography, High Pressure Liquid ; Feces - microbiology ; Food industries ; Fundamental and applied biological sciences. Psychology ; Gas Chromatography-Mass Spectrometry ; General aspects ; General aspects. Body compartment ; Lignans - analysis ; Lignans - metabolism ; Metabolisms and neurohumoral controls ; Methods of analysis, processing and quality control, regulation, standards ; Plant Extracts - analysis ; Plant Extracts - metabolism ; Vertebrates: anatomy and physiology, studies on body, several organs or systems</subject><ispartof>Journal of agricultural and food chemistry, 2001-07, Vol.49 (7), p.3178-3186</ispartof><rights>Copyright © 2001 American Chemical Society</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a444t-53431e333cf0287b702720ef2115fde7e542778861f5fab97f7864afa278cf073</citedby><cites>FETCH-LOGICAL-a444t-53431e333cf0287b702720ef2115fde7e542778861f5fab97f7864afa278cf073</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/jf010038a$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf010038a$$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=1071489$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11453749$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Heinonen, Satu</creatorcontrib><creatorcontrib>Nurmi, Tarja</creatorcontrib><creatorcontrib>Liukkonen, Kirsi</creatorcontrib><creatorcontrib>Poutanen, Kaisa</creatorcontrib><creatorcontrib>Wähälä, Kristiina</creatorcontrib><creatorcontrib>Deyama, Takeshi</creatorcontrib><creatorcontrib>Nishibe, Sansei</creatorcontrib><creatorcontrib>Adlercreutz, Herman</creatorcontrib><title>In Vitro Metabolism of Plant Lignans: New Precursors of Mammalian Lignans Enterolactone and Enterodiol</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>The metabolism of the plant lignans matairesinol, secoisolariciresinol, pinoresinol, syringaresinol, arctigenin, 7-hydroxymatairesinol, isolariciresinol, and lariciresinol by human fecal microflora was investigated to study their properties as mammalian lignan precursors. The quantitative analyses of lignan precursors and the mammalian lignans enterolactone and enterodiol were performed by HPLC with coulometric electrode array detector. The metabolic products, including mammalian lignans, were characterized as trimethylsilyl derivatives by gas chromatography−mass spectrometry. Matairesinol, secoisolariciresinol, lariciresinol, and pinoresinol were converted to mammalian lignans only. Several metabolites were isolated and tentatively identified as for syringaresinol and arctigenin in addition to the mammalian lignans. Metabolites of 7-hydroxymatairesinol were characterized as enterolactone and 7-hydroxyenterolactone by comparison with authentic reference compounds. A metabolic scheme describing the conversion of the most abundant new mammalian lignan precursors, pinoresinol and lariciresinol, is presented. Keywords: Phytoestrogens; lignans; matairesinol; secoisolariciresinol; lariciresinol; pinoresinol; syringaresinol; isolariciresinol; arctigenin; 7-hydroxymatairesinol; mammalian lignans; enterolactone; enterodiol</description><subject>4-Butyrolactone - analogs & derivatives</subject><subject>4-Butyrolactone - metabolism</subject><subject>Biological and medical sciences</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Feces - microbiology</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Gas Chromatography-Mass Spectrometry</subject><subject>General aspects</subject><subject>General aspects. Body compartment</subject><subject>Lignans - analysis</subject><subject>Lignans - metabolism</subject><subject>Metabolisms and neurohumoral controls</subject><subject>Methods of analysis, processing and quality control, regulation, standards</subject><subject>Plant Extracts - analysis</subject><subject>Plant Extracts - metabolism</subject><subject>Vertebrates: anatomy and physiology, studies on body, several organs or systems</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E9PFDEYBvDGaGQFDn4B04OYcBjp32nXm0FEkkUWXD14ad6dbU3XmRbamSg3rn5NP4nd7IgeODXp--uTvg9Czyl5TQmjR2tHKCFcwyM0oZKRSlKqH6MJKcNKy5ruoGc5rwkhWiryFO1QKiRXYjpB_izgL75PEZ_bHpax9bnD0eF5C6HHM_8tQMhvft_9wh_tDzxPthlSjilvzDl0HbQewl-HT0JvU2yh6WOwGMJqvFn52O6hJw7abPfHcxd9fn-yOP5QzS5Oz47fzioQQvSV5IJTyzlvHGFaLRVhihHrGKXSrayyUjCltK6pkw6WU-WUrgU4YEqXJ4rvolfb3OsUbwabe9P53Ni2LGTjkI2ipax6Sgo83MImxZyTdeY6-Q7SraHEbHo1970W-2IMHZadXf2TY5EFvBwB5AZalyA0Pv-XqKjQG1Ztmc-9_Xk_hvTd1IoraRbzT2b29fJKv2MLc1X8wdZDk806DimU6h743x-7EprQ</recordid><startdate>20010701</startdate><enddate>20010701</enddate><creator>Heinonen, Satu</creator><creator>Nurmi, Tarja</creator><creator>Liukkonen, Kirsi</creator><creator>Poutanen, Kaisa</creator><creator>Wähälä, Kristiina</creator><creator>Deyama, Takeshi</creator><creator>Nishibe, Sansei</creator><creator>Adlercreutz, Herman</creator><general>American Chemical Society</general><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>20010701</creationdate><title>In Vitro Metabolism of Plant Lignans: New Precursors of Mammalian Lignans Enterolactone and Enterodiol</title><author>Heinonen, Satu ; Nurmi, Tarja ; Liukkonen, Kirsi ; Poutanen, Kaisa ; Wähälä, Kristiina ; Deyama, Takeshi ; Nishibe, Sansei ; Adlercreutz, Herman</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a444t-53431e333cf0287b702720ef2115fde7e542778861f5fab97f7864afa278cf073</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>4-Butyrolactone - analogs & derivatives</topic><topic>4-Butyrolactone - metabolism</topic><topic>Biological and medical sciences</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Feces - microbiology</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>General aspects</topic><topic>General aspects. Body compartment</topic><topic>Lignans - analysis</topic><topic>Lignans - metabolism</topic><topic>Metabolisms and neurohumoral controls</topic><topic>Methods of analysis, processing and quality control, regulation, standards</topic><topic>Plant Extracts - analysis</topic><topic>Plant Extracts - metabolism</topic><topic>Vertebrates: anatomy and physiology, studies on body, several organs or systems</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Heinonen, Satu</creatorcontrib><creatorcontrib>Nurmi, Tarja</creatorcontrib><creatorcontrib>Liukkonen, Kirsi</creatorcontrib><creatorcontrib>Poutanen, Kaisa</creatorcontrib><creatorcontrib>Wähälä, Kristiina</creatorcontrib><creatorcontrib>Deyama, Takeshi</creatorcontrib><creatorcontrib>Nishibe, Sansei</creatorcontrib><creatorcontrib>Adlercreutz, Herman</creatorcontrib><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>Heinonen, Satu</au><au>Nurmi, Tarja</au><au>Liukkonen, Kirsi</au><au>Poutanen, Kaisa</au><au>Wähälä, Kristiina</au><au>Deyama, Takeshi</au><au>Nishibe, Sansei</au><au>Adlercreutz, Herman</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>In Vitro Metabolism of Plant Lignans: New Precursors of Mammalian Lignans Enterolactone and Enterodiol</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2001-07-01</date><risdate>2001</risdate><volume>49</volume><issue>7</issue><spage>3178</spage><epage>3186</epage><pages>3178-3186</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>The metabolism of the plant lignans matairesinol, secoisolariciresinol, pinoresinol, syringaresinol, arctigenin, 7-hydroxymatairesinol, isolariciresinol, and lariciresinol by human fecal microflora was investigated to study their properties as mammalian lignan precursors. The quantitative analyses of lignan precursors and the mammalian lignans enterolactone and enterodiol were performed by HPLC with coulometric electrode array detector. The metabolic products, including mammalian lignans, were characterized as trimethylsilyl derivatives by gas chromatography−mass spectrometry. Matairesinol, secoisolariciresinol, lariciresinol, and pinoresinol were converted to mammalian lignans only. Several metabolites were isolated and tentatively identified as for syringaresinol and arctigenin in addition to the mammalian lignans. Metabolites of 7-hydroxymatairesinol were characterized as enterolactone and 7-hydroxyenterolactone by comparison with authentic reference compounds. A metabolic scheme describing the conversion of the most abundant new mammalian lignan precursors, pinoresinol and lariciresinol, is presented. Keywords: Phytoestrogens; lignans; matairesinol; secoisolariciresinol; lariciresinol; pinoresinol; syringaresinol; isolariciresinol; arctigenin; 7-hydroxymatairesinol; mammalian lignans; enterolactone; enterodiol</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>11453749</pmid><doi>10.1021/jf010038a</doi><tpages>9</tpages></addata></record> |
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| identifier | ISSN: 0021-8561 |
| ispartof | Journal of agricultural and food chemistry, 2001-07, Vol.49 (7), p.3178-3186 |
| issn | 0021-8561 1520-5118 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_71010690 |
| source | MEDLINE; ACS Publications |
| subjects | 4-Butyrolactone - analogs & derivatives 4-Butyrolactone - metabolism Biological and medical sciences Chromatography, High Pressure Liquid Feces - microbiology Food industries Fundamental and applied biological sciences. Psychology Gas Chromatography-Mass Spectrometry General aspects General aspects. Body compartment Lignans - analysis Lignans - metabolism Metabolisms and neurohumoral controls Methods of analysis, processing and quality control, regulation, standards Plant Extracts - analysis Plant Extracts - metabolism Vertebrates: anatomy and physiology, studies on body, several organs or systems |
| title | In Vitro Metabolism of Plant Lignans: New Precursors of Mammalian Lignans Enterolactone and Enterodiol |
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