Kinetic Comparisons of Anthocyanin Reactivities towards 2,2′-Azobis(2-amidinopropane) (AAPH) Radicals, Hydrogen Peroxide and tert-Buthylhydroperoxide by Capillary Zone Electrophoresis
Twelve major anthocyanins identified in bilberry extracts were studied in vitro using capillary zone electrophoresis (CZE) for their reactions towards 2,2′-azobis(2-amidinopropane) (AAPH) radicals, hydrogen peroxides (H2O2) and tert-buthylhydroperoxides (t-BuOOH). Reactivity towards AAPH radicals wa...
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| Veröffentlicht in: | Chemical & Pharmaceutical Bulletin 2004, Vol.52(4), pp.434-438 |
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| creator | Ichiyanagi, Takashi Hatano, Yoshihiko Matsugo, Seiichi Konishi, Tetsuya |
| description | Twelve major anthocyanins identified in bilberry extracts were studied in vitro using capillary zone electrophoresis (CZE) for their reactions towards 2,2′-azobis(2-amidinopropane) (AAPH) radicals, hydrogen peroxides (H2O2) and tert-buthylhydroperoxides (t-BuOOH). Reactivity towards AAPH radicals was primarily determined by the aglycon structure, not by the type of sugar moiety. Delphinidins carrying three-hydroxyl groups on the B ring were most reactive followed by cyanidins, with two-hydroxyl groups. Further, methylation of the hydroxyl groups reduced reactivity towards AAPH radicals. However, reactivity of anthocyanins towards H2O2 was not significantly affected by aglycon structure or by the type of sugar moiety; there being no marked difference in reaction rates among the anthocyanins. Reactivity towards t-BuOOH was essentially the same as towards H2O2, although the reaction rate was several times smaller. Also, the reaction rate of anthocyanin towards peroxide was relatively high compared to that of (+)-catechin (approximately 30 times larger) measured as a reference antioxidant, whereas the reactivities of anthocyanins and (+)-catechin towards AAPH radicals were similar. |
| doi_str_mv | 10.1248/cpb.52.434 |
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Reactivity towards AAPH radicals was primarily determined by the aglycon structure, not by the type of sugar moiety. Delphinidins carrying three-hydroxyl groups on the B ring were most reactive followed by cyanidins, with two-hydroxyl groups. Further, methylation of the hydroxyl groups reduced reactivity towards AAPH radicals. However, reactivity of anthocyanins towards H2O2 was not significantly affected by aglycon structure or by the type of sugar moiety; there being no marked difference in reaction rates among the anthocyanins. Reactivity towards t-BuOOH was essentially the same as towards H2O2, although the reaction rate was several times smaller. Also, the reaction rate of anthocyanin towards peroxide was relatively high compared to that of (+)-catechin (approximately 30 times larger) measured as a reference antioxidant, whereas the reactivities of anthocyanins and (+)-catechin towards AAPH radicals were similar.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.52.434</identifier><identifier>PMID: 15056958</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Amidines - chemistry ; anthocyanin ; Anthocyanins - chemistry ; bilberry ; capillary zone electrophoresis ; Electrophoresis, Capillary ; Free Radicals - chemistry ; Hydrogen Peroxide - chemistry ; hydroperoxide ; Kinetics ; Oxidants - chemistry ; reactive oxygen species ; Structure-Activity Relationship ; structure–reactivity relationship ; tert-Butylhydroperoxide - chemistry</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2004, Vol.52(4), pp.434-438</ispartof><rights>2004 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2004</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c623t-3f7b3d674fc0dc3d52e88fee9d3c3f9cae9168e8620fd00d7e685c93436b67153</citedby><cites>FETCH-LOGICAL-c623t-3f7b3d674fc0dc3d52e88fee9d3c3f9cae9168e8620fd00d7e685c93436b67153</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15056958$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ichiyanagi, Takashi</creatorcontrib><creatorcontrib>Hatano, Yoshihiko</creatorcontrib><creatorcontrib>Matsugo, Seiichi</creatorcontrib><creatorcontrib>Konishi, Tetsuya</creatorcontrib><creatorcontrib>Niigata University of Pharmacy and Applied Life Sciences</creatorcontrib><creatorcontrib>aFaculty of Applied Life Sciences</creatorcontrib><creatorcontrib>University of Yamanashi</creatorcontrib><creatorcontrib>bFaculty of Pharmaceutical Sciences</creatorcontrib><creatorcontrib>cDivision of Biotechnology</creatorcontrib><creatorcontrib>Interdisciplinary Graduate School of Medicine and Engineering</creatorcontrib><title>Kinetic Comparisons of Anthocyanin Reactivities towards 2,2′-Azobis(2-amidinopropane) (AAPH) Radicals, Hydrogen Peroxide and tert-Buthylhydroperoxide by Capillary Zone Electrophoresis</title><title>Chemical & Pharmaceutical Bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Twelve major anthocyanins identified in bilberry extracts were studied in vitro using capillary zone electrophoresis (CZE) for their reactions towards 2,2′-azobis(2-amidinopropane) (AAPH) radicals, hydrogen peroxides (H2O2) and tert-buthylhydroperoxides (t-BuOOH). Reactivity towards AAPH radicals was primarily determined by the aglycon structure, not by the type of sugar moiety. Delphinidins carrying three-hydroxyl groups on the B ring were most reactive followed by cyanidins, with two-hydroxyl groups. Further, methylation of the hydroxyl groups reduced reactivity towards AAPH radicals. However, reactivity of anthocyanins towards H2O2 was not significantly affected by aglycon structure or by the type of sugar moiety; there being no marked difference in reaction rates among the anthocyanins. Reactivity towards t-BuOOH was essentially the same as towards H2O2, although the reaction rate was several times smaller. Also, the reaction rate of anthocyanin towards peroxide was relatively high compared to that of (+)-catechin (approximately 30 times larger) measured as a reference antioxidant, whereas the reactivities of anthocyanins and (+)-catechin towards AAPH radicals were similar.</description><subject>Amidines - chemistry</subject><subject>anthocyanin</subject><subject>Anthocyanins - chemistry</subject><subject>bilberry</subject><subject>capillary zone electrophoresis</subject><subject>Electrophoresis, Capillary</subject><subject>Free Radicals - chemistry</subject><subject>Hydrogen Peroxide - chemistry</subject><subject>hydroperoxide</subject><subject>Kinetics</subject><subject>Oxidants - chemistry</subject><subject>reactive oxygen species</subject><subject>Structure-Activity Relationship</subject><subject>structure–reactivity relationship</subject><subject>tert-Butylhydroperoxide - chemistry</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkcFu1DAQhiMEokvhwgMgS1xa1CyOHTvJCS2r0kVUoqrgwsVy7EnjVdYOthdYTjwTN16HJ8HRLtvLzGE-__OP_yx7XuB5Qcr6tRrbOSPzkpYPsllByypnhNCH2Qxj3OSEcnqSPQlhjTFhuKKPs5OCYcYbVs-yPx-MhWgUWrrNKL0JzgbkOrSwsXdqJ62x6BakiuabiQYCiu679DogckH-_vqdL3661oQzksuN0ca60btRWjhHZ4vFzeoc3UptlBzCBVrttHd3YNENePfDaEDSahTBx_ztNva7oZ-A8f-w3aGlHM0wSL9DX5wFdDmAiononYdgwtPsUZeE4dmhn2af311-Wq7y649X75eL61xxQmNOu6qlmldlp7BWVDMCdd0BNJoq2jVKQlPwGmpOcKcx1hXwmqmGlpS3vCoYPc1e7nXTaV-3EKJYu623aaUoSo5pTTkuE_VqTynvQvDQidGbTfIuCiymlERKSTAiUkoJfnGQ3LYb0PfoIZYEXO2BNJ2-z9khxXS_WIVK9bAxgmBcCowZmVpBRHJSTqUuMG8aViWlN3uldYjyDo6rpE-hD3B0tS_T6-Okl16Apf8AGqm-pg</recordid><startdate>20040401</startdate><enddate>20040401</enddate><creator>Ichiyanagi, Takashi</creator><creator>Hatano, Yoshihiko</creator><creator>Matsugo, Seiichi</creator><creator>Konishi, Tetsuya</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope></search><sort><creationdate>20040401</creationdate><title>Kinetic Comparisons of Anthocyanin Reactivities towards 2,2′-Azobis(2-amidinopropane) (AAPH) Radicals, Hydrogen Peroxide and tert-Buthylhydroperoxide by Capillary Zone Electrophoresis</title><author>Ichiyanagi, Takashi ; Hatano, Yoshihiko ; Matsugo, Seiichi ; Konishi, Tetsuya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c623t-3f7b3d674fc0dc3d52e88fee9d3c3f9cae9168e8620fd00d7e685c93436b67153</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Amidines - chemistry</topic><topic>anthocyanin</topic><topic>Anthocyanins - chemistry</topic><topic>bilberry</topic><topic>capillary zone electrophoresis</topic><topic>Electrophoresis, Capillary</topic><topic>Free Radicals - chemistry</topic><topic>Hydrogen Peroxide - chemistry</topic><topic>hydroperoxide</topic><topic>Kinetics</topic><topic>Oxidants - chemistry</topic><topic>reactive oxygen species</topic><topic>Structure-Activity Relationship</topic><topic>structure–reactivity relationship</topic><topic>tert-Butylhydroperoxide - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ichiyanagi, Takashi</creatorcontrib><creatorcontrib>Hatano, Yoshihiko</creatorcontrib><creatorcontrib>Matsugo, Seiichi</creatorcontrib><creatorcontrib>Konishi, Tetsuya</creatorcontrib><creatorcontrib>Niigata University of Pharmacy and Applied Life Sciences</creatorcontrib><creatorcontrib>aFaculty of Applied Life Sciences</creatorcontrib><creatorcontrib>University of Yamanashi</creatorcontrib><creatorcontrib>bFaculty of Pharmaceutical Sciences</creatorcontrib><creatorcontrib>cDivision of Biotechnology</creatorcontrib><creatorcontrib>Interdisciplinary Graduate School of Medicine and Engineering</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><jtitle>Chemical & Pharmaceutical Bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ichiyanagi, Takashi</au><au>Hatano, Yoshihiko</au><au>Matsugo, Seiichi</au><au>Konishi, Tetsuya</au><aucorp>Niigata University of Pharmacy and Applied Life Sciences</aucorp><aucorp>aFaculty of Applied Life Sciences</aucorp><aucorp>University of Yamanashi</aucorp><aucorp>bFaculty of Pharmaceutical Sciences</aucorp><aucorp>cDivision of Biotechnology</aucorp><aucorp>Interdisciplinary Graduate School of Medicine and Engineering</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Kinetic Comparisons of Anthocyanin Reactivities towards 2,2′-Azobis(2-amidinopropane) (AAPH) Radicals, Hydrogen Peroxide and tert-Buthylhydroperoxide by Capillary Zone Electrophoresis</atitle><jtitle>Chemical & Pharmaceutical Bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2004-04-01</date><risdate>2004</risdate><volume>52</volume><issue>4</issue><spage>434</spage><epage>438</epage><pages>434-438</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>Twelve major anthocyanins identified in bilberry extracts were studied in vitro using capillary zone electrophoresis (CZE) for their reactions towards 2,2′-azobis(2-amidinopropane) (AAPH) radicals, hydrogen peroxides (H2O2) and tert-buthylhydroperoxides (t-BuOOH). Reactivity towards AAPH radicals was primarily determined by the aglycon structure, not by the type of sugar moiety. Delphinidins carrying three-hydroxyl groups on the B ring were most reactive followed by cyanidins, with two-hydroxyl groups. Further, methylation of the hydroxyl groups reduced reactivity towards AAPH radicals. However, reactivity of anthocyanins towards H2O2 was not significantly affected by aglycon structure or by the type of sugar moiety; there being no marked difference in reaction rates among the anthocyanins. Reactivity towards t-BuOOH was essentially the same as towards H2O2, although the reaction rate was several times smaller. Also, the reaction rate of anthocyanin towards peroxide was relatively high compared to that of (+)-catechin (approximately 30 times larger) measured as a reference antioxidant, whereas the reactivities of anthocyanins and (+)-catechin towards AAPH radicals were similar.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>15056958</pmid><doi>10.1248/cpb.52.434</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Amidines - chemistry anthocyanin Anthocyanins - chemistry bilberry capillary zone electrophoresis Electrophoresis, Capillary Free Radicals - chemistry Hydrogen Peroxide - chemistry hydroperoxide Kinetics Oxidants - chemistry reactive oxygen species Structure-Activity Relationship structure–reactivity relationship tert-Butylhydroperoxide - chemistry |
| title | Kinetic Comparisons of Anthocyanin Reactivities towards 2,2′-Azobis(2-amidinopropane) (AAPH) Radicals, Hydrogen Peroxide and tert-Buthylhydroperoxide by Capillary Zone Electrophoresis |
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