Fate of Xanthohumol and Related Prenylflavonoids from Hops to Beer
The fate of three prenylated flavonoids of the chalcone type, xanthohumol, desmethylxanthohumol, and 3‘-geranylchalconaringenin, was monitored with LC/MS-MS from hops (Humulus lupulus L.) to beer in two brewing trials. The three prenylchalcones were largely converted into their isomeric flavanones,...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 1999-06, Vol.47 (6), p.2421-2428 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Stevens, Jan F Taylor, Alan W Clawson, Jeff E Deinzer, Max L |
| description | The fate of three prenylated flavonoids of the chalcone type, xanthohumol, desmethylxanthohumol, and 3‘-geranylchalconaringenin, was monitored with LC/MS-MS from hops (Humulus lupulus L.) to beer in two brewing trials. The three prenylchalcones were largely converted into their isomeric flavanones, isoxanthohumol, prenylnaringenins, and geranylnaringenins, respectively, in the boiling wort. Losses of prenylflavonoids were due to incomplete extraction from the hops into the wort (13−25%), adsorption to insoluble malt proteins (18−26%), and adsorption to yeast cells (11−32%) during fermentation. The overall yield of xanthohumol, after lagering of the beer and largely in the form of isoxanthohumol, amounted to 22−30% of the hops' xanthohumol. About 10% of the hops' desmethylxanthohumol, completely converted into prenylnaringenins, remained in the beers. 3‘-Geranylchalconaringenin behaved similarly to desmethylxanthohumol. Solubility experiments indicated that (1) malt carbohydrates form soluble complexes with xanthohumol and isoxanthohumol and (2) solubility does not dictate the isoxanthohumol levels of finished beers. Keywords: Beer; hops; Humulus lupulus; prenylated flavonoids; xanthohumol |
| doi_str_mv | 10.1021/jf990101k |
| format | Article |
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The three prenylchalcones were largely converted into their isomeric flavanones, isoxanthohumol, prenylnaringenins, and geranylnaringenins, respectively, in the boiling wort. Losses of prenylflavonoids were due to incomplete extraction from the hops into the wort (13−25%), adsorption to insoluble malt proteins (18−26%), and adsorption to yeast cells (11−32%) during fermentation. The overall yield of xanthohumol, after lagering of the beer and largely in the form of isoxanthohumol, amounted to 22−30% of the hops' xanthohumol. About 10% of the hops' desmethylxanthohumol, completely converted into prenylnaringenins, remained in the beers. 3‘-Geranylchalconaringenin behaved similarly to desmethylxanthohumol. Solubility experiments indicated that (1) malt carbohydrates form soluble complexes with xanthohumol and isoxanthohumol and (2) solubility does not dictate the isoxanthohumol levels of finished beers. Keywords: Beer; hops; Humulus lupulus; prenylated flavonoids; xanthohumol</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf990101k</identifier><identifier>PMID: 10794646</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Beer ; Beers ; Biological and medical sciences ; Fermentation ; Fermented food industries ; Flavonoids - analysis ; Flavonoids - chemistry ; Flavoring Agents ; Food industries ; Fundamental and applied biological sciences. Psychology ; Isomerism ; Mass Spectrometry ; Propiophenones - analysis ; Propiophenones - chemistry</subject><ispartof>Journal of agricultural and food chemistry, 1999-06, Vol.47 (6), p.2421-2428</ispartof><rights>Copyright © 1999 American Chemical Society</rights><rights>2000 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a444t-67c8f908a13ffe53fdc33ac1d2f61d521862fb16cd1ad11fbf078714b623fd813</citedby><cites>FETCH-LOGICAL-a444t-67c8f908a13ffe53fdc33ac1d2f61d521862fb16cd1ad11fbf078714b623fd813</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/jf990101k$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf990101k$$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=1210830$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10794646$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Stevens, Jan F</creatorcontrib><creatorcontrib>Taylor, Alan W</creatorcontrib><creatorcontrib>Clawson, Jeff E</creatorcontrib><creatorcontrib>Deinzer, Max L</creatorcontrib><title>Fate of Xanthohumol and Related Prenylflavonoids from Hops to Beer</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>The fate of three prenylated flavonoids of the chalcone type, xanthohumol, desmethylxanthohumol, and 3‘-geranylchalconaringenin, was monitored with LC/MS-MS from hops (Humulus lupulus L.) to beer in two brewing trials. The three prenylchalcones were largely converted into their isomeric flavanones, isoxanthohumol, prenylnaringenins, and geranylnaringenins, respectively, in the boiling wort. Losses of prenylflavonoids were due to incomplete extraction from the hops into the wort (13−25%), adsorption to insoluble malt proteins (18−26%), and adsorption to yeast cells (11−32%) during fermentation. The overall yield of xanthohumol, after lagering of the beer and largely in the form of isoxanthohumol, amounted to 22−30% of the hops' xanthohumol. About 10% of the hops' desmethylxanthohumol, completely converted into prenylnaringenins, remained in the beers. 3‘-Geranylchalconaringenin behaved similarly to desmethylxanthohumol. Solubility experiments indicated that (1) malt carbohydrates form soluble complexes with xanthohumol and isoxanthohumol and (2) solubility does not dictate the isoxanthohumol levels of finished beers. Keywords: Beer; hops; Humulus lupulus; prenylated flavonoids; xanthohumol</description><subject>Beer</subject><subject>Beers</subject><subject>Biological and medical sciences</subject><subject>Fermentation</subject><subject>Fermented food industries</subject><subject>Flavonoids - analysis</subject><subject>Flavonoids - chemistry</subject><subject>Flavoring Agents</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Isomerism</subject><subject>Mass Spectrometry</subject><subject>Propiophenones - analysis</subject><subject>Propiophenones - chemistry</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>eNpt0E9P2zAYBnALbYIOOOwLIB_GpB0CfhPHdo4UjbGtEhUUMe1iuf4jUpy42Mm0fvsFpeo4cHoPz0-PXj0IfQRyBiSH85WrKgIEnvbQBMqcZCWAeIcmZAgzUTI4QB9SWhFCRMnJPjoAwivKKJug6ZXqLA4O_1Jt9xge-yZ4rFqDb60fEoPn0bYb77z6E9pQm4RdDA2-DuuEu4Cn1sYj9N4pn-zx9h6i-6uvi8vrbHbz7fvlxSxTlNIuY1wLVxGhoHDOloUzuiiUBpM7BqbMQbDcLYFpA8oAuKUjXHCgS5YPVkBxiD6PvesYnnubOtnUSVvvVWtDnySrKBeUv8AvI9QxpBStk-tYNypuJBD5MpjcDTbYk21pv2yseSXHhQbwaQtU0sq7qFpdp_8uByIKMrBsZHXq7N9drOKTZLzgpVzM7-SPn9MH8bukcjb409ErneQq9LEdpnvjv3-epYy-</recordid><startdate>19990601</startdate><enddate>19990601</enddate><creator>Stevens, Jan F</creator><creator>Taylor, Alan W</creator><creator>Clawson, Jeff E</creator><creator>Deinzer, Max L</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>19990601</creationdate><title>Fate of Xanthohumol and Related Prenylflavonoids from Hops to Beer</title><author>Stevens, Jan F ; Taylor, Alan W ; Clawson, Jeff E ; Deinzer, Max L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a444t-67c8f908a13ffe53fdc33ac1d2f61d521862fb16cd1ad11fbf078714b623fd813</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>Beer</topic><topic>Beers</topic><topic>Biological and medical sciences</topic><topic>Fermentation</topic><topic>Fermented food industries</topic><topic>Flavonoids - analysis</topic><topic>Flavonoids - chemistry</topic><topic>Flavoring Agents</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Isomerism</topic><topic>Mass Spectrometry</topic><topic>Propiophenones - analysis</topic><topic>Propiophenones - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Stevens, Jan F</creatorcontrib><creatorcontrib>Taylor, Alan W</creatorcontrib><creatorcontrib>Clawson, Jeff E</creatorcontrib><creatorcontrib>Deinzer, Max L</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>Stevens, Jan F</au><au>Taylor, Alan W</au><au>Clawson, Jeff E</au><au>Deinzer, Max L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Fate of Xanthohumol and Related Prenylflavonoids from Hops to Beer</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>1999-06-01</date><risdate>1999</risdate><volume>47</volume><issue>6</issue><spage>2421</spage><epage>2428</epage><pages>2421-2428</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>The fate of three prenylated flavonoids of the chalcone type, xanthohumol, desmethylxanthohumol, and 3‘-geranylchalconaringenin, was monitored with LC/MS-MS from hops (Humulus lupulus L.) to beer in two brewing trials. The three prenylchalcones were largely converted into their isomeric flavanones, isoxanthohumol, prenylnaringenins, and geranylnaringenins, respectively, in the boiling wort. Losses of prenylflavonoids were due to incomplete extraction from the hops into the wort (13−25%), adsorption to insoluble malt proteins (18−26%), and adsorption to yeast cells (11−32%) during fermentation. The overall yield of xanthohumol, after lagering of the beer and largely in the form of isoxanthohumol, amounted to 22−30% of the hops' xanthohumol. About 10% of the hops' desmethylxanthohumol, completely converted into prenylnaringenins, remained in the beers. 3‘-Geranylchalconaringenin behaved similarly to desmethylxanthohumol. Solubility experiments indicated that (1) malt carbohydrates form soluble complexes with xanthohumol and isoxanthohumol and (2) solubility does not dictate the isoxanthohumol levels of finished beers. Keywords: Beer; hops; Humulus lupulus; prenylated flavonoids; xanthohumol</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>10794646</pmid><doi>10.1021/jf990101k</doi><tpages>8</tpages></addata></record> |
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| subjects | Beer Beers Biological and medical sciences Fermentation Fermented food industries Flavonoids - analysis Flavonoids - chemistry Flavoring Agents Food industries Fundamental and applied biological sciences. Psychology Isomerism Mass Spectrometry Propiophenones - analysis Propiophenones - chemistry |
| title | Fate of Xanthohumol and Related Prenylflavonoids from Hops to Beer |
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