Photoisomerization of 2-[3-(2-thioxopyrrolidin-3-ylidene)methyl]-tryptophan, a yellow pigment in salted radish [Raphanus sativus] roots
The photostability of (E)-2-[3-(2-thioxopyrrolidin-3-ylidene)methyl]-tryptophan ((E)-TPMT), the main yellow pigment in salted radish, was studied. First we analyzed the photoproduct generated from (E)-TPMT under longwave UV irradiation. On the basis of NMR spectroscopy, the photoproduct was identifi...
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| Veröffentlicht in: | Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2008-09, Vol.72 (9), p.2262-2268 |
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| creator | Matsuoka, H.(Takasaki Univ. of Health and Welfare, Gunma (Japan)) Honzawa, S Takahashi, A Yoshikawa, H Watanabe, E Watanabe, T Ozawa, Y Yamada, Y Iizuka, T Uda, Y |
| description | The photostability of (E)-2-[3-(2-thioxopyrrolidin-3-ylidene)methyl]-tryptophan ((E)-TPMT), the main yellow pigment in salted radish, was studied. First we analyzed the photoproduct generated from (E)-TPMT under longwave UV irradiation. On the basis of NMR spectroscopy, the photoproduct was identified as Z-configurated TPMT, and isomerization from the Z- to the E-form was reversibly induced by Vis-light irradiation. The optimum wavelength for isomerization from the E- to the Z-form was 360-380 nm, and that for isomerization from the Z- to the E-form was 440-460 nm. The E/Z-ratios in the photostationary state under UV- and Vis-light irradiation conditions were approximately 0.95:1 and 26:1 respectively. The (Z)-isomer was more sensitive to light irradiation than the (E)-isomer in the quantum yield measurement. Yellowing was dependent on the ratio of the (Z)-isomer, because the b* and chroma value rose with increases in the (Z)-isomer by the colorimeters. Hence, it is possible that the formation of the (Z)-isomer contribute to the yellow color of takuan-zuke during long salting and fermentation. |
| doi_str_mv | 10.1271/bbb.80092 |
| format | Article |
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First we analyzed the photoproduct generated from (E)-TPMT under longwave UV irradiation. On the basis of NMR spectroscopy, the photoproduct was identified as Z-configurated TPMT, and isomerization from the Z- to the E-form was reversibly induced by Vis-light irradiation. The optimum wavelength for isomerization from the E- to the Z-form was 360-380 nm, and that for isomerization from the Z- to the E-form was 440-460 nm. The E/Z-ratios in the photostationary state under UV- and Vis-light irradiation conditions were approximately 0.95:1 and 26:1 respectively. The (Z)-isomer was more sensitive to light irradiation than the (E)-isomer in the quantum yield measurement. Yellowing was dependent on the ratio of the (Z)-isomer, because the b* and chroma value rose with increases in the (Z)-isomer by the colorimeters. Hence, it is possible that the formation of the (Z)-isomer contribute to the yellow color of takuan-zuke during long salting and fermentation.</description><identifier>ISSN: 0916-8451</identifier><identifier>EISSN: 1347-6947</identifier><identifier>DOI: 10.1271/bbb.80092</identifier><identifier>PMID: 18776682</identifier><language>eng</language><publisher>Tokyo: Japan Society for Bioscience, Biotechnology, and Agrochemistry</publisher><subject>Biological and medical sciences ; ENCURTIDOS ; ESTABILIDAD ; Fundamental and applied biological sciences. Psychology ; Hydrogen-Ion Concentration ; IRRADIACION ULTRAVIOLETA ; IRRADIATION ULTRAVIOLETTE ; ISOMERISATION ; Isomerism ; ISOMERIZACION ; ISOMERIZATION ; Light ; Nuclear Magnetic Resonance, Biomolecular ; Photochemistry ; photochromic compound ; photoisomerization ; PICKLES ; PIGMENT ; PIGMENTOS ; PIGMENTS ; Pigments, Biological - chemistry ; Pigments, Biological - isolation & purification ; Plant Roots - chemistry ; RABANO ; RADIS ; RADISHES ; Raphanus - chemistry ; RAPHANUS SATIVUS ; salted radish roots ; Sodium Chloride - chemistry ; Spectrophotometry, Ultraviolet ; STABILITE ; STABILITY ; Temperature ; tetrahydro-β-carboline derivative ; Thiones ; Time Factors ; Tryptophan - analogs & derivatives ; Tryptophan - chemistry ; Tryptophan - isolation & purification ; ULTRAVIOLET IRRADIATION ; Ultraviolet Rays ; yellow pigment</subject><ispartof>Bioscience, biotechnology, and biochemistry, 2008-09, Vol.72 (9), p.2262-2268</ispartof><rights>2008 by Japan Society for Bioscience, Biotechnology, and Agrochemistry 2008</rights><rights>2008 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 2008</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c544t-21261ea7e826fd107ad353bd8e84bbdaf617966db7189241a5b471bc0d31d22a3</citedby><cites>FETCH-LOGICAL-c544t-21261ea7e826fd107ad353bd8e84bbdaf617966db7189241a5b471bc0d31d22a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20804619$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18776682$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Matsuoka, H.(Takasaki Univ. of Health and Welfare, Gunma (Japan))</creatorcontrib><creatorcontrib>Honzawa, S</creatorcontrib><creatorcontrib>Takahashi, A</creatorcontrib><creatorcontrib>Yoshikawa, H</creatorcontrib><creatorcontrib>Watanabe, E</creatorcontrib><creatorcontrib>Watanabe, T</creatorcontrib><creatorcontrib>Ozawa, Y</creatorcontrib><creatorcontrib>Yamada, Y</creatorcontrib><creatorcontrib>Iizuka, T</creatorcontrib><creatorcontrib>Uda, Y</creatorcontrib><title>Photoisomerization of 2-[3-(2-thioxopyrrolidin-3-ylidene)methyl]-tryptophan, a yellow pigment in salted radish [Raphanus sativus] roots</title><title>Bioscience, biotechnology, and biochemistry</title><addtitle>Biosci Biotechnol Biochem</addtitle><description>The photostability of (E)-2-[3-(2-thioxopyrrolidin-3-ylidene)methyl]-tryptophan ((E)-TPMT), the main yellow pigment in salted radish, was studied. First we analyzed the photoproduct generated from (E)-TPMT under longwave UV irradiation. On the basis of NMR spectroscopy, the photoproduct was identified as Z-configurated TPMT, and isomerization from the Z- to the E-form was reversibly induced by Vis-light irradiation. The optimum wavelength for isomerization from the E- to the Z-form was 360-380 nm, and that for isomerization from the Z- to the E-form was 440-460 nm. The E/Z-ratios in the photostationary state under UV- and Vis-light irradiation conditions were approximately 0.95:1 and 26:1 respectively. The (Z)-isomer was more sensitive to light irradiation than the (E)-isomer in the quantum yield measurement. Yellowing was dependent on the ratio of the (Z)-isomer, because the b* and chroma value rose with increases in the (Z)-isomer by the colorimeters. Hence, it is possible that the formation of the (Z)-isomer contribute to the yellow color of takuan-zuke during long salting and fermentation.</description><subject>Biological and medical sciences</subject><subject>ENCURTIDOS</subject><subject>ESTABILIDAD</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hydrogen-Ion Concentration</subject><subject>IRRADIACION ULTRAVIOLETA</subject><subject>IRRADIATION ULTRAVIOLETTE</subject><subject>ISOMERISATION</subject><subject>Isomerism</subject><subject>ISOMERIZACION</subject><subject>ISOMERIZATION</subject><subject>Light</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Photochemistry</subject><subject>photochromic compound</subject><subject>photoisomerization</subject><subject>PICKLES</subject><subject>PIGMENT</subject><subject>PIGMENTOS</subject><subject>PIGMENTS</subject><subject>Pigments, Biological - chemistry</subject><subject>Pigments, Biological - isolation & purification</subject><subject>Plant Roots - chemistry</subject><subject>RABANO</subject><subject>RADIS</subject><subject>RADISHES</subject><subject>Raphanus - chemistry</subject><subject>RAPHANUS SATIVUS</subject><subject>salted radish roots</subject><subject>Sodium Chloride - chemistry</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>STABILITE</subject><subject>STABILITY</subject><subject>Temperature</subject><subject>tetrahydro-β-carboline derivative</subject><subject>Thiones</subject><subject>Time Factors</subject><subject>Tryptophan - analogs & derivatives</subject><subject>Tryptophan - chemistry</subject><subject>Tryptophan - isolation & purification</subject><subject>ULTRAVIOLET IRRADIATION</subject><subject>Ultraviolet Rays</subject><subject>yellow pigment</subject><issn>0916-8451</issn><issn>1347-6947</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0l1r1jAUB_AiinucXvgBlIIoDszMW5P0UoavDByiV2OUkyZdM9qmS9Jt9Qv4tc18HhXEq4Tkd5JD_imKxwQfEirJa631ocK4pneKDWFcIlFzebfY4JoIpHhF9ooHMV7gTEhF7hd7REkphKKb4sdJ75N30Y82uO-QnJ9K35UUnTL0kqLUO3_j5zUEPzjjJsTQmid2sgejTf06nKEU1jn5uYfpVQnlaofBX5ezOx_tlEo3lRGGZE0ZwLjYl6df4JYuMa8nd7XEszJ4n-LD4l4HQ7SPduN-8e3d269HH9Dx5_cfj94co7biPCFKqCAWpFVUdIZgCYZVTBtlFdfaQCeIrIUwWhJVU06g0lwS3WLDiKEU2H7xYnvuHPzlYmNqRhfb3DRM1i-xEXWV3whXGT77B174JUy5t4ZwXiuOqRBZHWxVG3yMwXbNHNwIYW0Ibm6zaXI2za9ssn26O3HRozV_5S6MDJ7vAMQWhi7A1Lr4x1GsMBekzo5vnZs6H0a49mEwTYJ18OF3Efvf_U-2ZR34Bs5DVp9OaN7K_6JiNfsJ-vCyug</recordid><startdate>20080901</startdate><enddate>20080901</enddate><creator>Matsuoka, H.(Takasaki Univ. of Health and Welfare, Gunma (Japan))</creator><creator>Honzawa, S</creator><creator>Takahashi, A</creator><creator>Yoshikawa, H</creator><creator>Watanabe, E</creator><creator>Watanabe, T</creator><creator>Ozawa, Y</creator><creator>Yamada, Y</creator><creator>Iizuka, T</creator><creator>Uda, Y</creator><general>Japan Society for Bioscience, Biotechnology, and Agrochemistry</general><general>Japan Society for Bioscience Biotechnology and Agrochemistry</general><general>Oxford University Press</general><scope>FBQ</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>20080901</creationdate><title>Photoisomerization of 2-[3-(2-thioxopyrrolidin-3-ylidene)methyl]-tryptophan, a yellow pigment in salted radish [Raphanus sativus] roots</title><author>Matsuoka, H.(Takasaki Univ. of Health and Welfare, Gunma (Japan)) ; Honzawa, S ; Takahashi, A ; Yoshikawa, H ; Watanabe, E ; Watanabe, T ; Ozawa, Y ; Yamada, Y ; Iizuka, T ; Uda, Y</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c544t-21261ea7e826fd107ad353bd8e84bbdaf617966db7189241a5b471bc0d31d22a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Biological and medical sciences</topic><topic>ENCURTIDOS</topic><topic>ESTABILIDAD</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Hydrogen-Ion Concentration</topic><topic>IRRADIACION ULTRAVIOLETA</topic><topic>IRRADIATION ULTRAVIOLETTE</topic><topic>ISOMERISATION</topic><topic>Isomerism</topic><topic>ISOMERIZACION</topic><topic>ISOMERIZATION</topic><topic>Light</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Photochemistry</topic><topic>photochromic compound</topic><topic>photoisomerization</topic><topic>PICKLES</topic><topic>PIGMENT</topic><topic>PIGMENTOS</topic><topic>PIGMENTS</topic><topic>Pigments, Biological - chemistry</topic><topic>Pigments, Biological - isolation & purification</topic><topic>Plant Roots - chemistry</topic><topic>RABANO</topic><topic>RADIS</topic><topic>RADISHES</topic><topic>Raphanus - chemistry</topic><topic>RAPHANUS SATIVUS</topic><topic>salted radish roots</topic><topic>Sodium Chloride - chemistry</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>STABILITE</topic><topic>STABILITY</topic><topic>Temperature</topic><topic>tetrahydro-β-carboline derivative</topic><topic>Thiones</topic><topic>Time Factors</topic><topic>Tryptophan - analogs & derivatives</topic><topic>Tryptophan - chemistry</topic><topic>Tryptophan - isolation & purification</topic><topic>ULTRAVIOLET IRRADIATION</topic><topic>Ultraviolet Rays</topic><topic>yellow pigment</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Matsuoka, H.(Takasaki Univ. of Health and Welfare, Gunma (Japan))</creatorcontrib><creatorcontrib>Honzawa, S</creatorcontrib><creatorcontrib>Takahashi, A</creatorcontrib><creatorcontrib>Yoshikawa, H</creatorcontrib><creatorcontrib>Watanabe, E</creatorcontrib><creatorcontrib>Watanabe, T</creatorcontrib><creatorcontrib>Ozawa, Y</creatorcontrib><creatorcontrib>Yamada, Y</creatorcontrib><creatorcontrib>Iizuka, T</creatorcontrib><creatorcontrib>Uda, Y</creatorcontrib><collection>AGRIS</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>Bioscience, biotechnology, and biochemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Matsuoka, H.(Takasaki Univ. of Health and Welfare, Gunma (Japan))</au><au>Honzawa, S</au><au>Takahashi, A</au><au>Yoshikawa, H</au><au>Watanabe, E</au><au>Watanabe, T</au><au>Ozawa, Y</au><au>Yamada, Y</au><au>Iizuka, T</au><au>Uda, Y</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photoisomerization of 2-[3-(2-thioxopyrrolidin-3-ylidene)methyl]-tryptophan, a yellow pigment in salted radish [Raphanus sativus] roots</atitle><jtitle>Bioscience, biotechnology, and biochemistry</jtitle><addtitle>Biosci Biotechnol Biochem</addtitle><date>2008-09-01</date><risdate>2008</risdate><volume>72</volume><issue>9</issue><spage>2262</spage><epage>2268</epage><pages>2262-2268</pages><issn>0916-8451</issn><eissn>1347-6947</eissn><abstract>The photostability of (E)-2-[3-(2-thioxopyrrolidin-3-ylidene)methyl]-tryptophan ((E)-TPMT), the main yellow pigment in salted radish, was studied. First we analyzed the photoproduct generated from (E)-TPMT under longwave UV irradiation. On the basis of NMR spectroscopy, the photoproduct was identified as Z-configurated TPMT, and isomerization from the Z- to the E-form was reversibly induced by Vis-light irradiation. The optimum wavelength for isomerization from the E- to the Z-form was 360-380 nm, and that for isomerization from the Z- to the E-form was 440-460 nm. The E/Z-ratios in the photostationary state under UV- and Vis-light irradiation conditions were approximately 0.95:1 and 26:1 respectively. The (Z)-isomer was more sensitive to light irradiation than the (E)-isomer in the quantum yield measurement. Yellowing was dependent on the ratio of the (Z)-isomer, because the b* and chroma value rose with increases in the (Z)-isomer by the colorimeters. Hence, it is possible that the formation of the (Z)-isomer contribute to the yellow color of takuan-zuke during long salting and fermentation.</abstract><cop>Tokyo</cop><pub>Japan Society for Bioscience, Biotechnology, and Agrochemistry</pub><pmid>18776682</pmid><doi>10.1271/bbb.80092</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Bioscience, biotechnology, and biochemistry, 2008-09, Vol.72 (9), p.2262-2268 |
| issn | 0916-8451 1347-6947 |
| language | eng |
| recordid | cdi_fao_agris_JP2009000539 |
| source | MEDLINE; Oxford University Press Journals All Titles (1996-Current); J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; Open Access Titles of Japan; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Biological and medical sciences ENCURTIDOS ESTABILIDAD Fundamental and applied biological sciences. Psychology Hydrogen-Ion Concentration IRRADIACION ULTRAVIOLETA IRRADIATION ULTRAVIOLETTE ISOMERISATION Isomerism ISOMERIZACION ISOMERIZATION Light Nuclear Magnetic Resonance, Biomolecular Photochemistry photochromic compound photoisomerization PICKLES PIGMENT PIGMENTOS PIGMENTS Pigments, Biological - chemistry Pigments, Biological - isolation & purification Plant Roots - chemistry RABANO RADIS RADISHES Raphanus - chemistry RAPHANUS SATIVUS salted radish roots Sodium Chloride - chemistry Spectrophotometry, Ultraviolet STABILITE STABILITY Temperature tetrahydro-β-carboline derivative Thiones Time Factors Tryptophan - analogs & derivatives Tryptophan - chemistry Tryptophan - isolation & purification ULTRAVIOLET IRRADIATION Ultraviolet Rays yellow pigment |
| title | Photoisomerization of 2-[3-(2-thioxopyrrolidin-3-ylidene)methyl]-tryptophan, a yellow pigment in salted radish [Raphanus sativus] roots |
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