Characterization of Creaming Precipitate of Tea Catechins and Caffeine in Aqueous Solution
The content of a crude precipitate formed by creaming, which was made from a catechin mixture and caffeine, was investigated by an integral volume of H-2 proton signals of tea catechins in the 1H-NMR spectrum. Gallated catechins formed a crude precipitate more predominantly than non-gallated catechi...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2012/09/01, Vol.60(9), pp.1182-1187 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | Sato, Takashi Kinoshita, Yoshifumi Tsutsumi, Hiroyuki Yamamoto, Hideji Ishizu, Takashi |
| description | The content of a crude precipitate formed by creaming, which was made from a catechin mixture and caffeine, was investigated by an integral volume of H-2 proton signals of tea catechins in the 1H-NMR spectrum. Gallated catechins formed a crude precipitate more predominantly than non-gallated catechins. The 2,3-cis-non-gallated catechin (−)-epicatechin (EC) formed a 1 : 1 complex with caffeine, and 2,3-cis-gallated catechin (−)-epicatechin gallate (ECg) formed a 2 : 4 complex with caffeine. The π-π complexation site of EC with caffeine was only the A ring, whereas that of ECg included all aromatic rings, A, B, and B′. It was thought that the hydrophobicity of the 2 : 4 complex of ECg and caffeine was stronger than that of the 1 : 1 complex of EC and caffeine, with the result that the 2 : 4 complex of ECg and caffeine precipitated by creaming more predominantly than the 1 : 1 complex of EC and caffeine in aqueous solution. |
| doi_str_mv | 10.1248/cpb.c12-00433 |
| format | Article |
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Gallated catechins formed a crude precipitate more predominantly than non-gallated catechins. The 2,3-cis-non-gallated catechin (−)-epicatechin (EC) formed a 1 : 1 complex with caffeine, and 2,3-cis-gallated catechin (−)-epicatechin gallate (ECg) formed a 2 : 4 complex with caffeine. The π-π complexation site of EC with caffeine was only the A ring, whereas that of ECg included all aromatic rings, A, B, and B′. It was thought that the hydrophobicity of the 2 : 4 complex of ECg and caffeine was stronger than that of the 1 : 1 complex of EC and caffeine, with the result that the 2 : 4 complex of ECg and caffeine precipitated by creaming more predominantly than the 1 : 1 complex of EC and caffeine in aqueous solution.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.c12-00433</identifier><identifier>PMID: 22976328</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>(−)-epicatechin ; (−)-epicatechin-3-O-gallate ; caffeine ; Caffeine - chemistry ; Catechin - analogs & derivatives ; Catechin - chemistry ; Chemical Precipitation ; creaming down ; Crystallography, X-Ray ; Magnetic Resonance Spectroscopy ; Models, Molecular ; Solutions ; X-ray crystallographic analysis ; π-π interaction</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2012/09/01, Vol.60(9), pp.1182-1187</ispartof><rights>2012 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2012</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c678t-a8b11e57ebacdda034a0771a14bb0845976c0439e0763208cbed3265fb62f04c3</citedby><cites>FETCH-LOGICAL-c678t-a8b11e57ebacdda034a0771a14bb0845976c0439e0763208cbed3265fb62f04c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22976328$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sato, Takashi</creatorcontrib><creatorcontrib>Kinoshita, Yoshifumi</creatorcontrib><creatorcontrib>Tsutsumi, Hiroyuki</creatorcontrib><creatorcontrib>Yamamoto, Hideji</creatorcontrib><creatorcontrib>Ishizu, Takashi</creatorcontrib><creatorcontrib>aFaculty of Pharmacy and Pharmaceutical Sciences</creatorcontrib><creatorcontrib>Faculty of Engineering</creatorcontrib><creatorcontrib>Fukuyama University</creatorcontrib><creatorcontrib>bDepartment of Applied Biological Science</creatorcontrib><title>Characterization of Creaming Precipitate of Tea Catechins and Caffeine in Aqueous Solution</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>The content of a crude precipitate formed by creaming, which was made from a catechin mixture and caffeine, was investigated by an integral volume of H-2 proton signals of tea catechins in the 1H-NMR spectrum. Gallated catechins formed a crude precipitate more predominantly than non-gallated catechins. The 2,3-cis-non-gallated catechin (−)-epicatechin (EC) formed a 1 : 1 complex with caffeine, and 2,3-cis-gallated catechin (−)-epicatechin gallate (ECg) formed a 2 : 4 complex with caffeine. The π-π complexation site of EC with caffeine was only the A ring, whereas that of ECg included all aromatic rings, A, B, and B′. It was thought that the hydrophobicity of the 2 : 4 complex of ECg and caffeine was stronger than that of the 1 : 1 complex of EC and caffeine, with the result that the 2 : 4 complex of ECg and caffeine precipitated by creaming more predominantly than the 1 : 1 complex of EC and caffeine in aqueous solution.</description><subject>(−)-epicatechin</subject><subject>(−)-epicatechin-3-O-gallate</subject><subject>caffeine</subject><subject>Caffeine - chemistry</subject><subject>Catechin - analogs & derivatives</subject><subject>Catechin - chemistry</subject><subject>Chemical Precipitation</subject><subject>creaming down</subject><subject>Crystallography, X-Ray</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Models, Molecular</subject><subject>Solutions</subject><subject>X-ray crystallographic analysis</subject><subject>π-π interaction</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkc1v1DAQxS0EokvhyBVF4sIlZfyR2DlWERSkSiBRLlwsx5l0vco6i50cyl_PZLdsJS7-mqc3P79h7C2HKy6U-egP3ZXnogRQUj5jGy6VLish5HO2AYCmFLKWF-xVzjsAUYGWL9mFEI2upTAb9qvduuT8jCn8cXOYYjENRZvQ7UO8L74n9OEQZjfj-n6Hrmjp7Lch5sLFnm7DgCFiEWJx_XvBacnFj2lcVqfX7MXgxoxvHvdL9vPzp7v2S3n77eZre31b-lqbuXSm4xwrjZ3zfe9AKgdac8dV14FRFZF6-luDsCKD8R32UtTV0NViAOXlJftw8j2kiRDybPchexxHF1cey0E2xjTcAEnf_yfdTUuKRGe5qkFVklcVqcqTyqcp54SDPaSwd-mBrOwauqXQLYVuj6GT_t2j69LtsT-r_6VMgpuTgKrBu3GKI2X21Ntn7be4D1bA0bSmuVngynJuxLpoggfDNTm1J6ddnt09nlu5NAc_4hGsBtusyxnwqUqzthjlXzqbqlQ</recordid><startdate>20120901</startdate><enddate>20120901</enddate><creator>Sato, Takashi</creator><creator>Kinoshita, Yoshifumi</creator><creator>Tsutsumi, Hiroyuki</creator><creator>Yamamoto, Hideji</creator><creator>Ishizu, Takashi</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><scope>7X8</scope></search><sort><creationdate>20120901</creationdate><title>Characterization of Creaming Precipitate of Tea Catechins and Caffeine in Aqueous Solution</title><author>Sato, Takashi ; Kinoshita, Yoshifumi ; Tsutsumi, Hiroyuki ; Yamamoto, Hideji ; Ishizu, Takashi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c678t-a8b11e57ebacdda034a0771a14bb0845976c0439e0763208cbed3265fb62f04c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>(−)-epicatechin</topic><topic>(−)-epicatechin-3-O-gallate</topic><topic>caffeine</topic><topic>Caffeine - chemistry</topic><topic>Catechin - analogs & derivatives</topic><topic>Catechin - chemistry</topic><topic>Chemical Precipitation</topic><topic>creaming down</topic><topic>Crystallography, X-Ray</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Models, Molecular</topic><topic>Solutions</topic><topic>X-ray crystallographic analysis</topic><topic>π-π interaction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sato, Takashi</creatorcontrib><creatorcontrib>Kinoshita, Yoshifumi</creatorcontrib><creatorcontrib>Tsutsumi, Hiroyuki</creatorcontrib><creatorcontrib>Yamamoto, Hideji</creatorcontrib><creatorcontrib>Ishizu, Takashi</creatorcontrib><creatorcontrib>aFaculty of Pharmacy and Pharmaceutical Sciences</creatorcontrib><creatorcontrib>Faculty of Engineering</creatorcontrib><creatorcontrib>Fukuyama University</creatorcontrib><creatorcontrib>bDepartment of Applied Biological Science</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><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sato, Takashi</au><au>Kinoshita, Yoshifumi</au><au>Tsutsumi, Hiroyuki</au><au>Yamamoto, Hideji</au><au>Ishizu, Takashi</au><aucorp>aFaculty of Pharmacy and Pharmaceutical Sciences</aucorp><aucorp>Faculty of Engineering</aucorp><aucorp>Fukuyama University</aucorp><aucorp>bDepartment of Applied Biological Science</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Characterization of Creaming Precipitate of Tea Catechins and Caffeine in Aqueous Solution</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2012-09-01</date><risdate>2012</risdate><volume>60</volume><issue>9</issue><spage>1182</spage><epage>1187</epage><pages>1182-1187</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>The content of a crude precipitate formed by creaming, which was made from a catechin mixture and caffeine, was investigated by an integral volume of H-2 proton signals of tea catechins in the 1H-NMR spectrum. Gallated catechins formed a crude precipitate more predominantly than non-gallated catechins. The 2,3-cis-non-gallated catechin (−)-epicatechin (EC) formed a 1 : 1 complex with caffeine, and 2,3-cis-gallated catechin (−)-epicatechin gallate (ECg) formed a 2 : 4 complex with caffeine. The π-π complexation site of EC with caffeine was only the A ring, whereas that of ECg included all aromatic rings, A, B, and B′. It was thought that the hydrophobicity of the 2 : 4 complex of ECg and caffeine was stronger than that of the 1 : 1 complex of EC and caffeine, with the result that the 2 : 4 complex of ECg and caffeine precipitated by creaming more predominantly than the 1 : 1 complex of EC and caffeine in aqueous solution.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>22976328</pmid><doi>10.1248/cpb.c12-00433</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | (−)-epicatechin (−)-epicatechin-3-O-gallate caffeine Caffeine - chemistry Catechin - analogs & derivatives Catechin - chemistry Chemical Precipitation creaming down Crystallography, X-Ray Magnetic Resonance Spectroscopy Models, Molecular Solutions X-ray crystallographic analysis π-π interaction |
| title | Characterization of Creaming Precipitate of Tea Catechins and Caffeine in Aqueous Solution |
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