Enzymatic Preparation of Kaempferol from Green Tea Seed and Its Antioxidant Activity
Among the flavonols in green tea, kaempferol has many biological activities but kaempferol of plant origin is too expensive to be used in commercial products. Recently, we confirmed that green tea seed (GTS) contained a reasonable amount of kaempferol glycoside. After conducting structure analysis,...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2006-04, Vol.54 (8), p.2951-2956 |
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| creator | Park, Jun Seong Rho, Ho Sik Kim, Duck Hee Chang, Ih Seop |
| description | Among the flavonols in green tea, kaempferol has many biological activities but kaempferol of plant origin is too expensive to be used in commercial products. Recently, we confirmed that green tea seed (GTS) contained a reasonable amount of kaempferol glycoside. After conducting structure analysis, two kaempferol glycosides were identified, kaempferol-3-O-[2-O-β-d-galactopyranosyl-6-O-α-l-rhamnopyranosyl]-β-d-glucopyranoside (compound 1) and kaempferol-3-O-[2-O-β-d-xylopyranosyl-6-O-α-l-rhamnopyranosyl]-β-d-glucopyranoside (compound 2), respectively. Also, a commercially useful method for kaempferol preparation was suggested by enzymatic hydrolysis using these two flavonoids. After several enzyme reactions were performed for the complete bioconversion of compounds 1 and 2 to kaempferol, we found that the optimum enzyme combination was reaction with β-galactosidase and hesperidinase. Finally, we produced pure kaempferol with over 95% purity. We also compared the antioxidant effect of these two GTS flavonoids and its aglycone, kaempferol. Kaempferol is a more efficient scavenger of 1,1-diphenyl-2-picrylhydrazyl radicals and a better inhibitor of xanthine/xanthine oxidase than the two glycosides. Keywords: Tea seed; enzymatic hydrolysis; antioxidant; kaempferol; kaempferol glycoside |
| doi_str_mv | 10.1021/jf052900a |
| format | Article |
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Recently, we confirmed that green tea seed (GTS) contained a reasonable amount of kaempferol glycoside. After conducting structure analysis, two kaempferol glycosides were identified, kaempferol-3-O-[2-O-β-d-galactopyranosyl-6-O-α-l-rhamnopyranosyl]-β-d-glucopyranoside (compound 1) and kaempferol-3-O-[2-O-β-d-xylopyranosyl-6-O-α-l-rhamnopyranosyl]-β-d-glucopyranoside (compound 2), respectively. Also, a commercially useful method for kaempferol preparation was suggested by enzymatic hydrolysis using these two flavonoids. After several enzyme reactions were performed for the complete bioconversion of compounds 1 and 2 to kaempferol, we found that the optimum enzyme combination was reaction with β-galactosidase and hesperidinase. Finally, we produced pure kaempferol with over 95% purity. We also compared the antioxidant effect of these two GTS flavonoids and its aglycone, kaempferol. Kaempferol is a more efficient scavenger of 1,1-diphenyl-2-picrylhydrazyl radicals and a better inhibitor of xanthine/xanthine oxidase than the two glycosides. Keywords: Tea seed; enzymatic hydrolysis; antioxidant; kaempferol; kaempferol glycoside</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf052900a</identifier><identifier>PMID: 16608214</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>antioxidant activity ; antioxidants ; Antioxidants - pharmacology ; beta-galactosidase ; beta-Galactosidase - metabolism ; Biological and medical sciences ; Camellia sinensis ; Camellia sinensis - chemistry ; Coffee, tea and other stimulative beverage industries ; enzymatic treatment ; Enzyme Inhibitors - pharmacology ; Food industries ; Free Radical Scavengers ; free radicals ; Fundamental and applied biological sciences. Psychology ; Glycoside Hydrolases - metabolism ; glycosides ; hesperidinase ; Hydrolysis ; isolation ; kaempferol ; kaempferol glycoside ; Kaempferols - isolation & purification ; Kaempferols - pharmacology ; O-glycoside hydrolases ; seeds ; Seeds - chemistry ; Xanthine Oxidase - antagonists & inhibitors</subject><ispartof>Journal of agricultural and food chemistry, 2006-04, Vol.54 (8), p.2951-2956</ispartof><rights>Copyright © 2006 American Chemical Society</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a471t-8ac9331cbc6e39860ad9e589c0d44f3a4ffa3a9790126fefc1feafdf725c79fd3</citedby><cites>FETCH-LOGICAL-a471t-8ac9331cbc6e39860ad9e589c0d44f3a4ffa3a9790126fefc1feafdf725c79fd3</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/jf052900a$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf052900a$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17708998$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16608214$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Park, Jun Seong</creatorcontrib><creatorcontrib>Rho, Ho Sik</creatorcontrib><creatorcontrib>Kim, Duck Hee</creatorcontrib><creatorcontrib>Chang, Ih Seop</creatorcontrib><title>Enzymatic Preparation of Kaempferol from Green Tea Seed and Its Antioxidant Activity</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Among the flavonols in green tea, kaempferol has many biological activities but kaempferol of plant origin is too expensive to be used in commercial products. Recently, we confirmed that green tea seed (GTS) contained a reasonable amount of kaempferol glycoside. After conducting structure analysis, two kaempferol glycosides were identified, kaempferol-3-O-[2-O-β-d-galactopyranosyl-6-O-α-l-rhamnopyranosyl]-β-d-glucopyranoside (compound 1) and kaempferol-3-O-[2-O-β-d-xylopyranosyl-6-O-α-l-rhamnopyranosyl]-β-d-glucopyranoside (compound 2), respectively. Also, a commercially useful method for kaempferol preparation was suggested by enzymatic hydrolysis using these two flavonoids. After several enzyme reactions were performed for the complete bioconversion of compounds 1 and 2 to kaempferol, we found that the optimum enzyme combination was reaction with β-galactosidase and hesperidinase. Finally, we produced pure kaempferol with over 95% purity. We also compared the antioxidant effect of these two GTS flavonoids and its aglycone, kaempferol. Kaempferol is a more efficient scavenger of 1,1-diphenyl-2-picrylhydrazyl radicals and a better inhibitor of xanthine/xanthine oxidase than the two glycosides. Keywords: Tea seed; enzymatic hydrolysis; antioxidant; kaempferol; kaempferol glycoside</description><subject>antioxidant activity</subject><subject>antioxidants</subject><subject>Antioxidants - pharmacology</subject><subject>beta-galactosidase</subject><subject>beta-Galactosidase - metabolism</subject><subject>Biological and medical sciences</subject><subject>Camellia sinensis</subject><subject>Camellia sinensis - chemistry</subject><subject>Coffee, tea and other stimulative beverage industries</subject><subject>enzymatic treatment</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Food industries</subject><subject>Free Radical Scavengers</subject><subject>free radicals</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Glycoside Hydrolases - metabolism</subject><subject>glycosides</subject><subject>hesperidinase</subject><subject>Hydrolysis</subject><subject>isolation</subject><subject>kaempferol</subject><subject>kaempferol glycoside</subject><subject>Kaempferols - isolation & purification</subject><subject>Kaempferols - pharmacology</subject><subject>O-glycoside hydrolases</subject><subject>seeds</subject><subject>Seeds - chemistry</subject><subject>Xanthine Oxidase - antagonists & inhibitors</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE1vEzEQhi1ERdPCgT8AvoDEYct4v2wfo6qUfkgEZXvhYk29Y7Rhd53aG9T01-MqUXrhNK80z7wz8zL2XsCZgFx8XTmocg2Ar9hMVDlklRDqNZtBamaqqsUxO4lxBQCqkvCGHYu6BpWLcsaai_FpO-DUWb4ItMaQpB-5d_wGaVg7Cr7nLviBXwaikTeEfEnUchxbfjVFPh_TwGPX4jjxuZ26v920fcuOHPaR3u3rKbv7dtGcf89uf1xenc9vMyylmDKFVheFsPe2pkKrGrDVVCltoS1LV2DpHBaopQaR146cFY7QtU7mlZXatcUp-7zzXQf_sKE4maGLlvoeR_KbaGqZTAupEvhlB9rgYwzkzDp0A4atEWCeIzSHCBP7YW-6uR-ofSH3mSXg0x7AaLF3AUfbxRdOSlBaPy_NdlwXJ3o89DH8SYcVsjLNYml-_soXjb4WBhL_ccc79AZ_h-R5t8xBFCBA1pDEYTPaaFZ-E8aU7n9e-AfmKp09</recordid><startdate>20060419</startdate><enddate>20060419</enddate><creator>Park, Jun Seong</creator><creator>Rho, Ho Sik</creator><creator>Kim, Duck Hee</creator><creator>Chang, Ih Seop</creator><general>American Chemical Society</general><scope>FBQ</scope><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>20060419</creationdate><title>Enzymatic Preparation of Kaempferol from Green Tea Seed and Its Antioxidant Activity</title><author>Park, Jun Seong ; Rho, Ho Sik ; Kim, Duck Hee ; Chang, Ih Seop</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a471t-8ac9331cbc6e39860ad9e589c0d44f3a4ffa3a9790126fefc1feafdf725c79fd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>antioxidant activity</topic><topic>antioxidants</topic><topic>Antioxidants - pharmacology</topic><topic>beta-galactosidase</topic><topic>beta-Galactosidase - metabolism</topic><topic>Biological and medical sciences</topic><topic>Camellia sinensis</topic><topic>Camellia sinensis - chemistry</topic><topic>Coffee, tea and other stimulative beverage industries</topic><topic>enzymatic treatment</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Food industries</topic><topic>Free Radical Scavengers</topic><topic>free radicals</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Glycoside Hydrolases - metabolism</topic><topic>glycosides</topic><topic>hesperidinase</topic><topic>Hydrolysis</topic><topic>isolation</topic><topic>kaempferol</topic><topic>kaempferol glycoside</topic><topic>Kaempferols - isolation & purification</topic><topic>Kaempferols - pharmacology</topic><topic>O-glycoside hydrolases</topic><topic>seeds</topic><topic>Seeds - chemistry</topic><topic>Xanthine Oxidase - antagonists & inhibitors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Park, Jun Seong</creatorcontrib><creatorcontrib>Rho, Ho Sik</creatorcontrib><creatorcontrib>Kim, Duck Hee</creatorcontrib><creatorcontrib>Chang, Ih Seop</creatorcontrib><collection>AGRIS</collection><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>Park, Jun Seong</au><au>Rho, Ho Sik</au><au>Kim, Duck Hee</au><au>Chang, Ih Seop</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enzymatic Preparation of Kaempferol from Green Tea Seed and Its Antioxidant Activity</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2006-04-19</date><risdate>2006</risdate><volume>54</volume><issue>8</issue><spage>2951</spage><epage>2956</epage><pages>2951-2956</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Among the flavonols in green tea, kaempferol has many biological activities but kaempferol of plant origin is too expensive to be used in commercial products. Recently, we confirmed that green tea seed (GTS) contained a reasonable amount of kaempferol glycoside. After conducting structure analysis, two kaempferol glycosides were identified, kaempferol-3-O-[2-O-β-d-galactopyranosyl-6-O-α-l-rhamnopyranosyl]-β-d-glucopyranoside (compound 1) and kaempferol-3-O-[2-O-β-d-xylopyranosyl-6-O-α-l-rhamnopyranosyl]-β-d-glucopyranoside (compound 2), respectively. Also, a commercially useful method for kaempferol preparation was suggested by enzymatic hydrolysis using these two flavonoids. After several enzyme reactions were performed for the complete bioconversion of compounds 1 and 2 to kaempferol, we found that the optimum enzyme combination was reaction with β-galactosidase and hesperidinase. Finally, we produced pure kaempferol with over 95% purity. We also compared the antioxidant effect of these two GTS flavonoids and its aglycone, kaempferol. Kaempferol is a more efficient scavenger of 1,1-diphenyl-2-picrylhydrazyl radicals and a better inhibitor of xanthine/xanthine oxidase than the two glycosides. Keywords: Tea seed; enzymatic hydrolysis; antioxidant; kaempferol; kaempferol glycoside</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16608214</pmid><doi>10.1021/jf052900a</doi><tpages>6</tpages></addata></record> |
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| subjects | antioxidant activity antioxidants Antioxidants - pharmacology beta-galactosidase beta-Galactosidase - metabolism Biological and medical sciences Camellia sinensis Camellia sinensis - chemistry Coffee, tea and other stimulative beverage industries enzymatic treatment Enzyme Inhibitors - pharmacology Food industries Free Radical Scavengers free radicals Fundamental and applied biological sciences. Psychology Glycoside Hydrolases - metabolism glycosides hesperidinase Hydrolysis isolation kaempferol kaempferol glycoside Kaempferols - isolation & purification Kaempferols - pharmacology O-glycoside hydrolases seeds Seeds - chemistry Xanthine Oxidase - antagonists & inhibitors |
| title | Enzymatic Preparation of Kaempferol from Green Tea Seed and Its Antioxidant Activity |
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