Isolation of phenolic compounds from hop extracts using polyvinylpolypyrrolidone: Characterization by high-performance liquid chromatography–diode array detection–electrospray tandem mass spectrometry
The aim of the present work was the development of a suitable methodology for the separation and determination of phenolic compounds in the hop plant. The developed methodology was based on the sample purification by adsorption of phenolic compounds from the matrix to polyvinylpolypyrrolidone (PVPP)...
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| creator | Magalhães, Paulo J. Vieira, Joana S. Gonçalves, Luís M. Pacheco, João G. Guido, Luís F. Barros, Aquiles A. |
| description | The aim of the present work was the development of a suitable methodology for the separation and determination of phenolic compounds in the hop plant. The developed methodology was based on the sample purification by adsorption of phenolic compounds from the matrix to polyvinylpolypyrrolidone (PVPP) and subsequent desorption of the adsorbed polyphenols with acetone/water (70:30, v/v). At last, the extract was analyzed by HPLC–DAD and HPLC–ESI-MS/MS. The first phase of this work consisted of the study of the adsorption behavior of several classes of phenolic compounds (e.g. phenolic acids, flavonols, and flavanols) by PVPP in model solutions. It has been observed that the process of adsorption of the different phenolic compounds to PVPP (at low concentrations) is differentiated, depending on the structure of the compound (number of OH groups, aromatic rings, and stereochemistry hindrance). For example, within the phenolic acids class (benzoic,
p-hydroxybenzoic, protocatechuic and gallic acids) the PVPP adsorption increases with the number of OH groups of the phenolic compound. On the other hand, the derivatization of OH groups (methylation and glycosylation) resulted in a greatly diminished binding. The use of PVPP revealed to be very efficient for adsorption of several phenolic compounds such as catechin, epicatechin, xanthohumol and quercetin, since high adsorption and recovery values were obtained. The methodology was further applied for the extraction and isolation of phenolic compounds from hops. With this methodology, it was possible to obtain high adsorption values (≥80%) and recovery yield values (≥70%) for the most important phenolic compounds from hops such as xanthohumol, catechin, epicatechin, quercetin and kaempferol glycosides, and in addition it allows the identification of about 30 phenolic compounds by HPLC–DAD and HPLC–ESI-MS/MS. |
| doi_str_mv | 10.1016/j.chroma.2009.10.068 |
| format | Article |
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p-hydroxybenzoic, protocatechuic and gallic acids) the PVPP adsorption increases with the number of OH groups of the phenolic compound. On the other hand, the derivatization of OH groups (methylation and glycosylation) resulted in a greatly diminished binding. The use of PVPP revealed to be very efficient for adsorption of several phenolic compounds such as catechin, epicatechin, xanthohumol and quercetin, since high adsorption and recovery values were obtained. The methodology was further applied for the extraction and isolation of phenolic compounds from hops. With this methodology, it was possible to obtain high adsorption values (≥80%) and recovery yield values (≥70%) for the most important phenolic compounds from hops such as xanthohumol, catechin, epicatechin, quercetin and kaempferol glycosides, and in addition it allows the identification of about 30 phenolic compounds by HPLC–DAD and HPLC–ESI-MS/MS.</description><identifier>ISSN: 0021-9673</identifier><identifier>EISSN: 1873-3778</identifier><identifier>DOI: 10.1016/j.chroma.2009.10.068</identifier><identifier>PMID: 19913228</identifier><identifier>CODEN: JOCRAM</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject><![CDATA[Adsorption ; Beers ; Biological and medical sciences ; Catechin - isolation & purification ; Chromatography, High Pressure Liquid - methods ; diode array detection ; Equipment Reuse ; Fermented food industries ; Flavonoids - isolation & purification ; Food industries ; Fundamental and applied biological sciences. Psychology ; General pharmacology ; high performance liquid chromatography ; Hops ; HPLC–DAD ; HPLC–ESI-MS/MS ; Humulus - chemistry ; Humulus lupulus ; mass spectrometry ; Medical sciences ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Phenolic compounds ; Phenols - isolation & purification ; plant extracts ; Plant Extracts - chemistry ; Polyphenols ; polyvinylpolypyrrolidone ; Polyvinylpolypyrrolidone (PVPP) ; Povidone - analogs & derivatives ; Povidone - chemistry ; Propiophenones - isolation & purification ; Quercetin - isolation & purification ; separation ; Spectrometry, Mass, Electrospray Ionization - methods ; Tandem Mass Spectrometry - methods ; Temperature]]></subject><ispartof>Journal of Chromatography A, 2010-05, Vol.1217 (19), p.3258-3268</ispartof><rights>2009 Elsevier B.V.</rights><rights>2015 INIST-CNRS</rights><rights>Copyright (c) 2009 Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c447t-c19be584adec0b3700550af9a7018fb1f3f9bf76fda4b8da146a6778554f758b3</citedby><cites>FETCH-LOGICAL-c447t-c19be584adec0b3700550af9a7018fb1f3f9bf76fda4b8da146a6778554f758b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.chroma.2009.10.068$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>309,310,314,780,784,789,790,3550,23930,23931,25140,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22758889$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19913228$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Magalhães, Paulo J.</creatorcontrib><creatorcontrib>Vieira, Joana S.</creatorcontrib><creatorcontrib>Gonçalves, Luís M.</creatorcontrib><creatorcontrib>Pacheco, João G.</creatorcontrib><creatorcontrib>Guido, Luís F.</creatorcontrib><creatorcontrib>Barros, Aquiles A.</creatorcontrib><title>Isolation of phenolic compounds from hop extracts using polyvinylpolypyrrolidone: Characterization by high-performance liquid chromatography–diode array detection–electrospray tandem mass spectrometry</title><title>Journal of Chromatography A</title><addtitle>J Chromatogr A</addtitle><description>The aim of the present work was the development of a suitable methodology for the separation and determination of phenolic compounds in the hop plant. The developed methodology was based on the sample purification by adsorption of phenolic compounds from the matrix to polyvinylpolypyrrolidone (PVPP) and subsequent desorption of the adsorbed polyphenols with acetone/water (70:30, v/v). At last, the extract was analyzed by HPLC–DAD and HPLC–ESI-MS/MS. The first phase of this work consisted of the study of the adsorption behavior of several classes of phenolic compounds (e.g. phenolic acids, flavonols, and flavanols) by PVPP in model solutions. It has been observed that the process of adsorption of the different phenolic compounds to PVPP (at low concentrations) is differentiated, depending on the structure of the compound (number of OH groups, aromatic rings, and stereochemistry hindrance). For example, within the phenolic acids class (benzoic,
p-hydroxybenzoic, protocatechuic and gallic acids) the PVPP adsorption increases with the number of OH groups of the phenolic compound. On the other hand, the derivatization of OH groups (methylation and glycosylation) resulted in a greatly diminished binding. The use of PVPP revealed to be very efficient for adsorption of several phenolic compounds such as catechin, epicatechin, xanthohumol and quercetin, since high adsorption and recovery values were obtained. The methodology was further applied for the extraction and isolation of phenolic compounds from hops. With this methodology, it was possible to obtain high adsorption values (≥80%) and recovery yield values (≥70%) for the most important phenolic compounds from hops such as xanthohumol, catechin, epicatechin, quercetin and kaempferol glycosides, and in addition it allows the identification of about 30 phenolic compounds by HPLC–DAD and HPLC–ESI-MS/MS.</description><subject>Adsorption</subject><subject>Beers</subject><subject>Biological and medical sciences</subject><subject>Catechin - isolation & purification</subject><subject>Chromatography, High Pressure Liquid - methods</subject><subject>diode array detection</subject><subject>Equipment Reuse</subject><subject>Fermented food industries</subject><subject>Flavonoids - isolation & purification</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General pharmacology</subject><subject>high performance liquid chromatography</subject><subject>Hops</subject><subject>HPLC–DAD</subject><subject>HPLC–ESI-MS/MS</subject><subject>Humulus - chemistry</subject><subject>Humulus lupulus</subject><subject>mass spectrometry</subject><subject>Medical sciences</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Phenolic compounds</subject><subject>Phenols - isolation & purification</subject><subject>plant extracts</subject><subject>Plant Extracts - chemistry</subject><subject>Polyphenols</subject><subject>polyvinylpolypyrrolidone</subject><subject>Polyvinylpolypyrrolidone (PVPP)</subject><subject>Povidone - analogs & derivatives</subject><subject>Povidone - chemistry</subject><subject>Propiophenones - isolation & purification</subject><subject>Quercetin - isolation & purification</subject><subject>separation</subject><subject>Spectrometry, Mass, Electrospray Ionization - methods</subject><subject>Tandem Mass Spectrometry - methods</subject><subject>Temperature</subject><issn>0021-9673</issn><issn>1873-3778</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kUuO1DAQhiMEYoaBGyDwBrFKY-flhMVIqMVjpJFYwKytil3uuJXEHjsZEVbcgWtxCk6CM2nBjpWtqq9e_58kzxndMcqqN8ed7LwdYJdR2sTQjlb1g-Sc1TxPc87rh8k5pRlLm4rnZ8mTEI6UMk559jg5Y03D8iyrz5NfV8H2MBk7EquJ63C0vZFE2sHZeVSB6DiDdNYR_DZ5kFMgczDjgTjbL3dmXPr14xbvY52yI74l-w5WEL35vjVuF9KZQ5c69Nr6AUaJpDe3s1FkO2GyBw-uW37_-KmMVUjAe1iIwgnl2iHGsY9fb4NbExOMCgcyQAgkuPvEgJNfniaPNPQBn53ei-Tmw_uv-0_p9eePV_t316ksCj6lkjUtlnUBCiVtc05pWVLQDXDKat0yneum1bzSCoq2VsCKCqqoaFkWmpd1m18kr7e-ztvbGcMkBhMk9j2MaOcgmrKoaMOKMpLFRsq4e_CohfNmAL8IRsVqoziKTQOx2rhGo42x7MVpwNwOqP4VnXyLwKsTAEFCr30U1YS_XJbFPeu6idzLjdNgBRx8ZG6-ZJTl8dKcZfcbXm4ERsHuDHoRpMFokTI-KiuUNf_f9Q-N5NFy</recordid><startdate>20100507</startdate><enddate>20100507</enddate><creator>Magalhães, Paulo J.</creator><creator>Vieira, Joana S.</creator><creator>Gonçalves, Luís M.</creator><creator>Pacheco, João G.</creator><creator>Guido, Luís F.</creator><creator>Barros, Aquiles A.</creator><general>Elsevier B.V</general><general>Amsterdam; New York: Elsevier</general><general>Elsevier</general><scope>FBQ</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>7QH</scope><scope>7U7</scope><scope>7UA</scope><scope>C1K</scope><scope>F1W</scope><scope>H97</scope><scope>L.G</scope></search><sort><creationdate>20100507</creationdate><title>Isolation of phenolic compounds from hop extracts using polyvinylpolypyrrolidone: Characterization by high-performance liquid chromatography–diode array detection–electrospray tandem mass spectrometry</title><author>Magalhães, Paulo J. ; Vieira, Joana S. ; Gonçalves, Luís M. ; Pacheco, João G. ; Guido, Luís F. ; Barros, Aquiles A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c447t-c19be584adec0b3700550af9a7018fb1f3f9bf76fda4b8da146a6778554f758b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Adsorption</topic><topic>Beers</topic><topic>Biological and medical sciences</topic><topic>Catechin - isolation & purification</topic><topic>Chromatography, High Pressure Liquid - methods</topic><topic>diode array detection</topic><topic>Equipment Reuse</topic><topic>Fermented food industries</topic><topic>Flavonoids - isolation & purification</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General pharmacology</topic><topic>high performance liquid chromatography</topic><topic>Hops</topic><topic>HPLC–DAD</topic><topic>HPLC–ESI-MS/MS</topic><topic>Humulus - chemistry</topic><topic>Humulus lupulus</topic><topic>mass spectrometry</topic><topic>Medical sciences</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Phenolic compounds</topic><topic>Phenols - isolation & purification</topic><topic>plant extracts</topic><topic>Plant Extracts - chemistry</topic><topic>Polyphenols</topic><topic>polyvinylpolypyrrolidone</topic><topic>Polyvinylpolypyrrolidone (PVPP)</topic><topic>Povidone - analogs & derivatives</topic><topic>Povidone - chemistry</topic><topic>Propiophenones - isolation & purification</topic><topic>Quercetin - isolation & purification</topic><topic>separation</topic><topic>Spectrometry, Mass, Electrospray Ionization - methods</topic><topic>Tandem Mass Spectrometry - methods</topic><topic>Temperature</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Magalhães, Paulo J.</creatorcontrib><creatorcontrib>Vieira, Joana S.</creatorcontrib><creatorcontrib>Gonçalves, Luís M.</creatorcontrib><creatorcontrib>Pacheco, João G.</creatorcontrib><creatorcontrib>Guido, Luís F.</creatorcontrib><creatorcontrib>Barros, Aquiles A.</creatorcontrib><collection>AGRIS</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>Aqualine</collection><collection>Toxicology Abstracts</collection><collection>Water Resources Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 3: Aquatic Pollution & Environmental Quality</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><jtitle>Journal of Chromatography A</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Magalhães, Paulo J.</au><au>Vieira, Joana S.</au><au>Gonçalves, Luís M.</au><au>Pacheco, João G.</au><au>Guido, Luís F.</au><au>Barros, Aquiles A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isolation of phenolic compounds from hop extracts using polyvinylpolypyrrolidone: Characterization by high-performance liquid chromatography–diode array detection–electrospray tandem mass spectrometry</atitle><jtitle>Journal of Chromatography A</jtitle><addtitle>J Chromatogr A</addtitle><date>2010-05-07</date><risdate>2010</risdate><volume>1217</volume><issue>19</issue><spage>3258</spage><epage>3268</epage><pages>3258-3268</pages><issn>0021-9673</issn><eissn>1873-3778</eissn><coden>JOCRAM</coden><abstract>The aim of the present work was the development of a suitable methodology for the separation and determination of phenolic compounds in the hop plant. The developed methodology was based on the sample purification by adsorption of phenolic compounds from the matrix to polyvinylpolypyrrolidone (PVPP) and subsequent desorption of the adsorbed polyphenols with acetone/water (70:30, v/v). At last, the extract was analyzed by HPLC–DAD and HPLC–ESI-MS/MS. The first phase of this work consisted of the study of the adsorption behavior of several classes of phenolic compounds (e.g. phenolic acids, flavonols, and flavanols) by PVPP in model solutions. It has been observed that the process of adsorption of the different phenolic compounds to PVPP (at low concentrations) is differentiated, depending on the structure of the compound (number of OH groups, aromatic rings, and stereochemistry hindrance). For example, within the phenolic acids class (benzoic,
p-hydroxybenzoic, protocatechuic and gallic acids) the PVPP adsorption increases with the number of OH groups of the phenolic compound. On the other hand, the derivatization of OH groups (methylation and glycosylation) resulted in a greatly diminished binding. The use of PVPP revealed to be very efficient for adsorption of several phenolic compounds such as catechin, epicatechin, xanthohumol and quercetin, since high adsorption and recovery values were obtained. The methodology was further applied for the extraction and isolation of phenolic compounds from hops. With this methodology, it was possible to obtain high adsorption values (≥80%) and recovery yield values (≥70%) for the most important phenolic compounds from hops such as xanthohumol, catechin, epicatechin, quercetin and kaempferol glycosides, and in addition it allows the identification of about 30 phenolic compounds by HPLC–DAD and HPLC–ESI-MS/MS.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><pmid>19913228</pmid><doi>10.1016/j.chroma.2009.10.068</doi><tpages>11</tpages></addata></record> |
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| ispartof | Journal of Chromatography A, 2010-05, Vol.1217 (19), p.3258-3268 |
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| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Adsorption Beers Biological and medical sciences Catechin - isolation & purification Chromatography, High Pressure Liquid - methods diode array detection Equipment Reuse Fermented food industries Flavonoids - isolation & purification Food industries Fundamental and applied biological sciences. Psychology General pharmacology high performance liquid chromatography Hops HPLC–DAD HPLC–ESI-MS/MS Humulus - chemistry Humulus lupulus mass spectrometry Medical sciences Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Phenolic compounds Phenols - isolation & purification plant extracts Plant Extracts - chemistry Polyphenols polyvinylpolypyrrolidone Polyvinylpolypyrrolidone (PVPP) Povidone - analogs & derivatives Povidone - chemistry Propiophenones - isolation & purification Quercetin - isolation & purification separation Spectrometry, Mass, Electrospray Ionization - methods Tandem Mass Spectrometry - methods Temperature |
| title | Isolation of phenolic compounds from hop extracts using polyvinylpolypyrrolidone: Characterization by high-performance liquid chromatography–diode array detection–electrospray tandem mass spectrometry |
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