Isolation and Characterization of Water-Soluble Intermediates of Blue Pigments Transformed from Geniposide of Gardenia jasminoides
Gardenia blue dye was obtained through the reaction of methylamine with genipin, the aglycone of geniposide isolated from the fruits of Gardenia jasminoides. The resulting blue pigments were passed through Bio-Gel P-2 resin yielding five fractions, GM1−GM5. Four fractions (GM1−GM4) were all blue pig...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2002-10, Vol.50 (22), p.6511-6514 |
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| container_issue | 22 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Park, Jee-Eun Lee, Jae-Youn Kim, Hong-Gyu Hahn, Tae-Ryong Paik, Young-Sook |
| description | Gardenia blue dye was obtained through the reaction of methylamine with genipin, the aglycone of geniposide isolated from the fruits of Gardenia jasminoides. The resulting blue pigments were passed through Bio-Gel P-2 resin yielding five fractions, GM1−GM5. Four fractions (GM1−GM4) were all blue pigments, and the first eluted higher molecular weight fraction GM1 had a higher tinctorial strength than the later eluted lower molecular weight fractions, GM2−GM4. The last eluted GM5 fraction with λmax of 292 nm was colorless and was confirmed as the true intermediate of the blue pigments on the basis of UV−vis spectrophotometric evidence. The GM5 fraction was composed of two epimeric isomers, and their structures were characterized by 1H NMR, 1H−1H COSY, 13C NMR, and HMQC and HMBC spectral measurements. Keywords: Gardenia jasminoides; genipine; methylamine; intermediates; gardenia blue dye |
| doi_str_mv | 10.1021/jf020499b |
| format | Article |
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The resulting blue pigments were passed through Bio-Gel P-2 resin yielding five fractions, GM1−GM5. Four fractions (GM1−GM4) were all blue pigments, and the first eluted higher molecular weight fraction GM1 had a higher tinctorial strength than the later eluted lower molecular weight fractions, GM2−GM4. The last eluted GM5 fraction with λmax of 292 nm was colorless and was confirmed as the true intermediate of the blue pigments on the basis of UV−vis spectrophotometric evidence. The GM5 fraction was composed of two epimeric isomers, and their structures were characterized by 1H NMR, 1H−1H COSY, 13C NMR, and HMQC and HMBC spectral measurements. Keywords: Gardenia jasminoides; genipine; methylamine; intermediates; gardenia blue dye</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf020499b</identifier><identifier>PMID: 12381142</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Agronomy. Soil science and plant productions ; Biological and medical sciences ; Chemical constitution ; Economic plant physiology ; Fundamental and applied biological sciences. Psychology ; Gardenia - chemistry ; Iridoids ; Isomerism ; Methylamines ; Molecular Weight ; Pigments, Biological - chemistry ; Pyrans - analysis ; Pyrans - chemistry ; Solubility</subject><ispartof>Journal of agricultural and food chemistry, 2002-10, Vol.50 (22), p.6511-6514</ispartof><rights>Copyright © 2002 American Chemical Society</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-630001faae33b89c4c082dc84bbfd2c7cad4f84d61e6bb2cfd396d5aaaad3dd93</citedby><cites>FETCH-LOGICAL-a445t-630001faae33b89c4c082dc84bbfd2c7cad4f84d61e6bb2cfd396d5aaaad3dd93</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/jf020499b$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf020499b$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>309,310,314,780,784,789,790,2765,23930,23931,25140,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14353423$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12381142$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Park, Jee-Eun</creatorcontrib><creatorcontrib>Lee, Jae-Youn</creatorcontrib><creatorcontrib>Kim, Hong-Gyu</creatorcontrib><creatorcontrib>Hahn, Tae-Ryong</creatorcontrib><creatorcontrib>Paik, Young-Sook</creatorcontrib><title>Isolation and Characterization of Water-Soluble Intermediates of Blue Pigments Transformed from Geniposide of Gardenia jasminoides</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Gardenia blue dye was obtained through the reaction of methylamine with genipin, the aglycone of geniposide isolated from the fruits of Gardenia jasminoides. The resulting blue pigments were passed through Bio-Gel P-2 resin yielding five fractions, GM1−GM5. Four fractions (GM1−GM4) were all blue pigments, and the first eluted higher molecular weight fraction GM1 had a higher tinctorial strength than the later eluted lower molecular weight fractions, GM2−GM4. The last eluted GM5 fraction with λmax of 292 nm was colorless and was confirmed as the true intermediate of the blue pigments on the basis of UV−vis spectrophotometric evidence. The GM5 fraction was composed of two epimeric isomers, and their structures were characterized by 1H NMR, 1H−1H COSY, 13C NMR, and HMQC and HMBC spectral measurements. Keywords: Gardenia jasminoides; genipine; methylamine; intermediates; gardenia blue dye</description><subject>Agronomy. Soil science and plant productions</subject><subject>Biological and medical sciences</subject><subject>Chemical constitution</subject><subject>Economic plant physiology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Gardenia - chemistry</subject><subject>Iridoids</subject><subject>Isomerism</subject><subject>Methylamines</subject><subject>Molecular Weight</subject><subject>Pigments, Biological - chemistry</subject><subject>Pyrans - analysis</subject><subject>Pyrans - chemistry</subject><subject>Solubility</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>eNptkE9v1DAQxS0EokvhwBdAvoDUQ8CO48Q5wopuVyqiUhfRmzXxH_CSxFtPIlGOfHK82lX3gi_WvPfT08wj5DVn7zkr-YetZyWr2rZ7QhZclqyQnKunZMGyWShZ8zPyAnHLGFOyYc_JGS-F4rwqF-TvGmMPU4gjhdHS5U9IYCaXwp-DGD39DnkubmM_d72j6zFPg7Mhq7i3P_Wzozfhx-DGCekmwYg-7gnqUxzoyo1hFzFYt4dXkGwWgG4BhzDGLONL8sxDj-7V8T8n3y4_b5ZXxfXX1Xr58bqAqpJTUYu8P_cATohOtaYyTJXWqKrrvC1NY8BWXlW25q7uutJ4K9raSsjPCmtbcU7eHXJ3Kd7PDic9BDSu72F0cUbdlFwxJVQGLw6gSRExOa93KQyQHjRnel-4fiw8s2-OoXOXbz6Rx4Yz8PYIABrofe7HBDxxlZAiY5krDlzAyf1-9CH90nUjGqk3N7f6i7gTzdXdpZanXDCot3FOY-7uPwv-A12jppU</recordid><startdate>20021023</startdate><enddate>20021023</enddate><creator>Park, Jee-Eun</creator><creator>Lee, Jae-Youn</creator><creator>Kim, Hong-Gyu</creator><creator>Hahn, Tae-Ryong</creator><creator>Paik, Young-Sook</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><scope>7X8</scope></search><sort><creationdate>20021023</creationdate><title>Isolation and Characterization of Water-Soluble Intermediates of Blue Pigments Transformed from Geniposide of Gardenia jasminoides</title><author>Park, Jee-Eun ; Lee, Jae-Youn ; Kim, Hong-Gyu ; Hahn, Tae-Ryong ; Paik, Young-Sook</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-630001faae33b89c4c082dc84bbfd2c7cad4f84d61e6bb2cfd396d5aaaad3dd93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Agronomy. Soil science and plant productions</topic><topic>Biological and medical sciences</topic><topic>Chemical constitution</topic><topic>Economic plant physiology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Gardenia - chemistry</topic><topic>Iridoids</topic><topic>Isomerism</topic><topic>Methylamines</topic><topic>Molecular Weight</topic><topic>Pigments, Biological - chemistry</topic><topic>Pyrans - analysis</topic><topic>Pyrans - chemistry</topic><topic>Solubility</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Park, Jee-Eun</creatorcontrib><creatorcontrib>Lee, Jae-Youn</creatorcontrib><creatorcontrib>Kim, Hong-Gyu</creatorcontrib><creatorcontrib>Hahn, Tae-Ryong</creatorcontrib><creatorcontrib>Paik, Young-Sook</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><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, Jee-Eun</au><au>Lee, Jae-Youn</au><au>Kim, Hong-Gyu</au><au>Hahn, Tae-Ryong</au><au>Paik, Young-Sook</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isolation and Characterization of Water-Soluble Intermediates of Blue Pigments Transformed from Geniposide of Gardenia jasminoides</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2002-10-23</date><risdate>2002</risdate><volume>50</volume><issue>22</issue><spage>6511</spage><epage>6514</epage><pages>6511-6514</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Gardenia blue dye was obtained through the reaction of methylamine with genipin, the aglycone of geniposide isolated from the fruits of Gardenia jasminoides. The resulting blue pigments were passed through Bio-Gel P-2 resin yielding five fractions, GM1−GM5. Four fractions (GM1−GM4) were all blue pigments, and the first eluted higher molecular weight fraction GM1 had a higher tinctorial strength than the later eluted lower molecular weight fractions, GM2−GM4. The last eluted GM5 fraction with λmax of 292 nm was colorless and was confirmed as the true intermediate of the blue pigments on the basis of UV−vis spectrophotometric evidence. The GM5 fraction was composed of two epimeric isomers, and their structures were characterized by 1H NMR, 1H−1H COSY, 13C NMR, and HMQC and HMBC spectral measurements. Keywords: Gardenia jasminoides; genipine; methylamine; intermediates; gardenia blue dye</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12381142</pmid><doi>10.1021/jf020499b</doi><tpages>4</tpages></addata></record> |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Agronomy. Soil science and plant productions Biological and medical sciences Chemical constitution Economic plant physiology Fundamental and applied biological sciences. Psychology Gardenia - chemistry Iridoids Isomerism Methylamines Molecular Weight Pigments, Biological - chemistry Pyrans - analysis Pyrans - chemistry Solubility |
| title | Isolation and Characterization of Water-Soluble Intermediates of Blue Pigments Transformed from Geniposide of Gardenia jasminoides |
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