Antioxidant Activity of Prune (Prunus domestica L.) Constituents and a New Synergist
Ethanol extract of prune was separated into hexane-soluble and H2O-soluble fractions, and the H2O-soluble fraction was further separated into a methanol (MeOH) eluate and an H2O eluate by Diaion HP-20 column chromatography. The MeOH eluate exhibited the strongest antioxidant activity among the separ...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2002-06, Vol.50 (13), p.3708-3712 |
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| creator | Kayano, Shin-ichi Kikuzaki, Hiroe Fukutsuka, Naoko Mitani, Takahiko Nakatani, Nobuji |
| description | Ethanol extract of prune was separated into hexane-soluble and H2O-soluble fractions, and the H2O-soluble fraction was further separated into a methanol (MeOH) eluate and an H2O eluate by Diaion HP-20 column chromatography. The MeOH eluate exhibited the strongest antioxidant activity among the separated fractions evaluated by oxygen radical absorbance capacity (ORAC). Further purification of the MeOH eluate led to isolation of a novel compound, 4-amino-4-carboxychroman-2-one, together with four known compounds (p-coumaric acid, vanillic acid β-glucoside, protocatechuic acid, and caffeic acid), structures of which were identified by NMR and MS analyses. The ORAC values of these isolated compounds showed 0.15−1.43 units (μmol of Trolox equiv)/μmol, and the new compound showed a remarkable synergistic effect on caffeoylquinic acid isomers. The antioxidant activity of the MeOH eluate was highly dependent on the major prune components, caffeoylquinic acid isomers, with a contribution from the new synergist. Keywords: Prune (Prunus domestica L.); oxygen radical absorbance capacity (ORAC); HPLC; caffeoylquinic acid isomers; 4-amino-4-carboxychroman-2-one; synergist |
| doi_str_mv | 10.1021/jf0200164 |
| format | Article |
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Constituents and a New Synergist</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Kayano, Shin-ichi ; Kikuzaki, Hiroe ; Fukutsuka, Naoko ; Mitani, Takahiko ; Nakatani, Nobuji</creator><creatorcontrib>Kayano, Shin-ichi ; Kikuzaki, Hiroe ; Fukutsuka, Naoko ; Mitani, Takahiko ; Nakatani, Nobuji</creatorcontrib><description>Ethanol extract of prune was separated into hexane-soluble and H2O-soluble fractions, and the H2O-soluble fraction was further separated into a methanol (MeOH) eluate and an H2O eluate by Diaion HP-20 column chromatography. The MeOH eluate exhibited the strongest antioxidant activity among the separated fractions evaluated by oxygen radical absorbance capacity (ORAC). Further purification of the MeOH eluate led to isolation of a novel compound, 4-amino-4-carboxychroman-2-one, together with four known compounds (p-coumaric acid, vanillic acid β-glucoside, protocatechuic acid, and caffeic acid), structures of which were identified by NMR and MS analyses. The ORAC values of these isolated compounds showed 0.15−1.43 units (μmol of Trolox equiv)/μmol, and the new compound showed a remarkable synergistic effect on caffeoylquinic acid isomers. The antioxidant activity of the MeOH eluate was highly dependent on the major prune components, caffeoylquinic acid isomers, with a contribution from the new synergist. Keywords: Prune (Prunus domestica L.); oxygen radical absorbance capacity (ORAC); HPLC; caffeoylquinic acid isomers; 4-amino-4-carboxychroman-2-one; synergist</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf0200164</identifier><identifier>PMID: 12059147</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject><![CDATA[Agronomy. Soil science and plant productions ; Antioxidants - isolation & purification ; Antioxidants - pharmacology ; Biological and medical sciences ; Caffeic Acids - isolation & purification ; Caffeic Acids - pharmacology ; Chemical constitution ; Chromans - isolation & purification ; Chromans - pharmacology ; Coumaric Acids - isolation & purification ; Coumaric Acids - pharmacology ; Drug Synergism ; Economic plant physiology ; Ethanol ; Fundamental and applied biological sciences. Psychology ; General pharmacology ; Hexanes ; Hydroxybenzoates - isolation & purification ; Hydroxybenzoates - pharmacology ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Medical sciences ; Methanol ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plant Extracts - chemistry ; Propionates ; Prunus - chemistry ; Reactive Oxygen Species - chemistry ; Vanillic Acid - isolation & purification ; Vanillic Acid - pharmacology ; Water]]></subject><ispartof>Journal of agricultural and food chemistry, 2002-06, Vol.50 (13), p.3708-3712</ispartof><rights>Copyright © 2002 American Chemical Society</rights><rights>2002 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-5968782791178aa72ad90f0a4731780704a8de3e213e664f979f55c18d452f073</citedby><cites>FETCH-LOGICAL-a445t-5968782791178aa72ad90f0a4731780704a8de3e213e664f979f55c18d452f073</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/jf0200164$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf0200164$$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=13726201$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12059147$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kayano, Shin-ichi</creatorcontrib><creatorcontrib>Kikuzaki, Hiroe</creatorcontrib><creatorcontrib>Fukutsuka, Naoko</creatorcontrib><creatorcontrib>Mitani, Takahiko</creatorcontrib><creatorcontrib>Nakatani, Nobuji</creatorcontrib><title>Antioxidant Activity of Prune (Prunus domestica L.) Constituents and a New Synergist</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Ethanol extract of prune was separated into hexane-soluble and H2O-soluble fractions, and the H2O-soluble fraction was further separated into a methanol (MeOH) eluate and an H2O eluate by Diaion HP-20 column chromatography. The MeOH eluate exhibited the strongest antioxidant activity among the separated fractions evaluated by oxygen radical absorbance capacity (ORAC). Further purification of the MeOH eluate led to isolation of a novel compound, 4-amino-4-carboxychroman-2-one, together with four known compounds (p-coumaric acid, vanillic acid β-glucoside, protocatechuic acid, and caffeic acid), structures of which were identified by NMR and MS analyses. The ORAC values of these isolated compounds showed 0.15−1.43 units (μmol of Trolox equiv)/μmol, and the new compound showed a remarkable synergistic effect on caffeoylquinic acid isomers. The antioxidant activity of the MeOH eluate was highly dependent on the major prune components, caffeoylquinic acid isomers, with a contribution from the new synergist. Keywords: Prune (Prunus domestica L.); oxygen radical absorbance capacity (ORAC); HPLC; caffeoylquinic acid isomers; 4-amino-4-carboxychroman-2-one; synergist</description><subject>Agronomy. Soil science and plant productions</subject><subject>Antioxidants - isolation & purification</subject><subject>Antioxidants - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Caffeic Acids - isolation & purification</subject><subject>Caffeic Acids - pharmacology</subject><subject>Chemical constitution</subject><subject>Chromans - isolation & purification</subject><subject>Chromans - pharmacology</subject><subject>Coumaric Acids - isolation & purification</subject><subject>Coumaric Acids - pharmacology</subject><subject>Drug Synergism</subject><subject>Economic plant physiology</subject><subject>Ethanol</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General pharmacology</subject><subject>Hexanes</subject><subject>Hydroxybenzoates - isolation & purification</subject><subject>Hydroxybenzoates - pharmacology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Medical sciences</subject><subject>Methanol</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plant Extracts - chemistry</subject><subject>Propionates</subject><subject>Prunus - chemistry</subject><subject>Reactive Oxygen Species - chemistry</subject><subject>Vanillic Acid - isolation & purification</subject><subject>Vanillic Acid - pharmacology</subject><subject>Water</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEtPwzAQhC0EouVx4A8gX5DoIWXtxHFyrCpeUnhIFKk3a0lslNI6le1A--8JatVeOI1259Nodwi5YDBkwNnNzAAHYGlyQPpMcIgEY9kh6UNnRplIWY-ceD8DgExIOCY9xkHkLJF9MhnZUDerukIb6KgM9Xcd1rQx9NW1VtPrP2k9rZqF9qEukRbDAR03thtCq23wFG1FkT7rH_q2ttp91j6ckSODc6_Pt3pK3u9uJ-OHqHi5fxyPigiTRIRI5GkmMy5zxmSGKDlWORjARMbdAiQkmFU61pzFOk0Tk8vcCFGyrEoENyDjUzLY5Jau8d5po5auXqBbKwbqrxm1a6ZjLzfssv1Y6GpPbqvogKstgL7EuXFoy9rvuVjylAPruGjDdY_q1c5H96VSGUuhJq9valrIOH-aCvW0z8XSq1nTOttV8s-BvzVmg3E</recordid><startdate>20020619</startdate><enddate>20020619</enddate><creator>Kayano, Shin-ichi</creator><creator>Kikuzaki, Hiroe</creator><creator>Fukutsuka, Naoko</creator><creator>Mitani, Takahiko</creator><creator>Nakatani, Nobuji</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></search><sort><creationdate>20020619</creationdate><title>Antioxidant Activity of Prune (Prunus domestica L.) Constituents and a New Synergist</title><author>Kayano, Shin-ichi ; Kikuzaki, Hiroe ; Fukutsuka, Naoko ; Mitani, Takahiko ; Nakatani, Nobuji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-5968782791178aa72ad90f0a4731780704a8de3e213e664f979f55c18d452f073</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Agronomy. Soil science and plant productions</topic><topic>Antioxidants - isolation & purification</topic><topic>Antioxidants - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Caffeic Acids - isolation & purification</topic><topic>Caffeic Acids - pharmacology</topic><topic>Chemical constitution</topic><topic>Chromans - isolation & purification</topic><topic>Chromans - pharmacology</topic><topic>Coumaric Acids - isolation & purification</topic><topic>Coumaric Acids - pharmacology</topic><topic>Drug Synergism</topic><topic>Economic plant physiology</topic><topic>Ethanol</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General pharmacology</topic><topic>Hexanes</topic><topic>Hydroxybenzoates - isolation & purification</topic><topic>Hydroxybenzoates - pharmacology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Medical sciences</topic><topic>Methanol</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plant Extracts - chemistry</topic><topic>Propionates</topic><topic>Prunus - chemistry</topic><topic>Reactive Oxygen Species - chemistry</topic><topic>Vanillic Acid - isolation & purification</topic><topic>Vanillic Acid - pharmacology</topic><topic>Water</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kayano, Shin-ichi</creatorcontrib><creatorcontrib>Kikuzaki, Hiroe</creatorcontrib><creatorcontrib>Fukutsuka, Naoko</creatorcontrib><creatorcontrib>Mitani, Takahiko</creatorcontrib><creatorcontrib>Nakatani, Nobuji</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><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kayano, Shin-ichi</au><au>Kikuzaki, Hiroe</au><au>Fukutsuka, Naoko</au><au>Mitani, Takahiko</au><au>Nakatani, Nobuji</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antioxidant Activity of Prune (Prunus domestica L.) Constituents and a New Synergist</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2002-06-19</date><risdate>2002</risdate><volume>50</volume><issue>13</issue><spage>3708</spage><epage>3712</epage><pages>3708-3712</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Ethanol extract of prune was separated into hexane-soluble and H2O-soluble fractions, and the H2O-soluble fraction was further separated into a methanol (MeOH) eluate and an H2O eluate by Diaion HP-20 column chromatography. The MeOH eluate exhibited the strongest antioxidant activity among the separated fractions evaluated by oxygen radical absorbance capacity (ORAC). Further purification of the MeOH eluate led to isolation of a novel compound, 4-amino-4-carboxychroman-2-one, together with four known compounds (p-coumaric acid, vanillic acid β-glucoside, protocatechuic acid, and caffeic acid), structures of which were identified by NMR and MS analyses. The ORAC values of these isolated compounds showed 0.15−1.43 units (μmol of Trolox equiv)/μmol, and the new compound showed a remarkable synergistic effect on caffeoylquinic acid isomers. The antioxidant activity of the MeOH eluate was highly dependent on the major prune components, caffeoylquinic acid isomers, with a contribution from the new synergist. Keywords: Prune (Prunus domestica L.); oxygen radical absorbance capacity (ORAC); HPLC; caffeoylquinic acid isomers; 4-amino-4-carboxychroman-2-one; synergist</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12059147</pmid><doi>10.1021/jf0200164</doi><tpages>5</tpages></addata></record> |
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| ispartof | Journal of agricultural and food chemistry, 2002-06, Vol.50 (13), p.3708-3712 |
| issn | 0021-8561 1520-5118 |
| language | eng |
| recordid | cdi_crossref_primary_10_1021_jf0200164 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Agronomy. Soil science and plant productions Antioxidants - isolation & purification Antioxidants - pharmacology Biological and medical sciences Caffeic Acids - isolation & purification Caffeic Acids - pharmacology Chemical constitution Chromans - isolation & purification Chromans - pharmacology Coumaric Acids - isolation & purification Coumaric Acids - pharmacology Drug Synergism Economic plant physiology Ethanol Fundamental and applied biological sciences. Psychology General pharmacology Hexanes Hydroxybenzoates - isolation & purification Hydroxybenzoates - pharmacology Magnetic Resonance Spectroscopy Mass Spectrometry Medical sciences Methanol Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plant Extracts - chemistry Propionates Prunus - chemistry Reactive Oxygen Species - chemistry Vanillic Acid - isolation & purification Vanillic Acid - pharmacology Water |
| title | Antioxidant Activity of Prune (Prunus domestica L.) Constituents and a New Synergist |
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