Chemical Assignment of Structural Isomers of Sulfur-Containing Metabolites in Garlic by Liquid Chromatography-Fourier Transform Ion Cyclotron Resonance-Mass Spectrometry
The chemical assignment of metabolites is crucial to understanding the relation between food composition and biological activity. This study was designed to detect and chemically assign sulfur-containing metabolites by using LC-Fourier transform ion cyclotron resonance-mass spectrometry (FTICR-MS) i...
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| Veröffentlicht in: | The Journal of nutrition 2016-02, Vol.146 (2), p.397S-402S |
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| container_title | The Journal of nutrition |
| container_volume | 146 |
| creator | Nakabayashi, Ryo Sawada, Yuji Aoyagi, Morihiro Yamada, Yutaka Hirai, Masami Yokota Sakurai, Tetsuya Kamoi, Takahiro Rowan, Daryl D Saito, Kazuki |
| description | The chemical assignment of metabolites is crucial to understanding the relation between food composition and biological activity.
This study was designed to detect and chemically assign sulfur-containing metabolites by using LC-Fourier transform ion cyclotron resonance-mass spectrometry (FTICR-MS) in Allium plants.
Ultrahigh resolution (>250,000 full width at half-maximum) and mass accuracy ( |
| doi_str_mv | 10.3945/jn.114.202317 |
| format | Article |
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This study was designed to detect and chemically assign sulfur-containing metabolites by using LC-Fourier transform ion cyclotron resonance-mass spectrometry (FTICR-MS) in Allium plants.
Ultrahigh resolution (>250,000 full width at half-maximum) and mass accuracy (<1 mDa) by FTICR-MS allowed us to distinguish ions containing sulfur isotopes ((32)S and (34)S).
Putative 69 S-containing monoisotopic ions (S-ions) were extracted from the metabolome data of onion (Allium cepa), green onion (Allium fistulosum), and garlic (Allium sativum) on the basis of theoretical mass differences between (32)S-ions and their (34)S-substituted counterparts and on the natural abundance of (34)S. Eight S-ions were chemically assigned by using the reference data according to the guidelines of the Metabolomics Standards Initiative. Three ions detected in garlic were assigned as derived from the isomers γ-glutamyl-S-1-propenylcysteine and γ-glutamyl-S-2-propenylcysteine and as S-2-propenylmercaptoglutathione on the basis of differences in key product ions identified in reference tandem MS spectra.
The ability to discriminate between such geometric isomers will be extremely useful for the chemical assignment of unknown metabolites in MS-based metabolomics.</description><identifier>ISSN: 0022-3166</identifier><identifier>EISSN: 1541-6100</identifier><identifier>DOI: 10.3945/jn.114.202317</identifier><identifier>PMID: 26764333</identifier><language>eng</language><publisher>United States</publisher><subject>Chromatography, Liquid - methods ; Cyclotrons ; Cysteine - analysis ; Garlic - chemistry ; Glutathione - analysis ; Ions - analysis ; Isomerism ; Metabolome ; Metabolomics ; Onions - chemistry ; Spectroscopy, Fourier Transform Infrared - methods ; Sulfur - analysis ; Sulfur Isotopes - analysis</subject><ispartof>The Journal of nutrition, 2016-02, Vol.146 (2), p.397S-402S</ispartof><rights>2016 American Society for Nutrition.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c398t-a0537b006eae813e6b568f174db3a4cadebdbab691d51f40c8c85f373cb8a8b13</citedby><cites>FETCH-LOGICAL-c398t-a0537b006eae813e6b568f174db3a4cadebdbab691d51f40c8c85f373cb8a8b13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,27907,27908</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26764333$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nakabayashi, Ryo</creatorcontrib><creatorcontrib>Sawada, Yuji</creatorcontrib><creatorcontrib>Aoyagi, Morihiro</creatorcontrib><creatorcontrib>Yamada, Yutaka</creatorcontrib><creatorcontrib>Hirai, Masami Yokota</creatorcontrib><creatorcontrib>Sakurai, Tetsuya</creatorcontrib><creatorcontrib>Kamoi, Takahiro</creatorcontrib><creatorcontrib>Rowan, Daryl D</creatorcontrib><creatorcontrib>Saito, Kazuki</creatorcontrib><title>Chemical Assignment of Structural Isomers of Sulfur-Containing Metabolites in Garlic by Liquid Chromatography-Fourier Transform Ion Cyclotron Resonance-Mass Spectrometry</title><title>The Journal of nutrition</title><addtitle>J Nutr</addtitle><description>The chemical assignment of metabolites is crucial to understanding the relation between food composition and biological activity.
This study was designed to detect and chemically assign sulfur-containing metabolites by using LC-Fourier transform ion cyclotron resonance-mass spectrometry (FTICR-MS) in Allium plants.
Ultrahigh resolution (>250,000 full width at half-maximum) and mass accuracy (<1 mDa) by FTICR-MS allowed us to distinguish ions containing sulfur isotopes ((32)S and (34)S).
Putative 69 S-containing monoisotopic ions (S-ions) were extracted from the metabolome data of onion (Allium cepa), green onion (Allium fistulosum), and garlic (Allium sativum) on the basis of theoretical mass differences between (32)S-ions and their (34)S-substituted counterparts and on the natural abundance of (34)S. Eight S-ions were chemically assigned by using the reference data according to the guidelines of the Metabolomics Standards Initiative. Three ions detected in garlic were assigned as derived from the isomers γ-glutamyl-S-1-propenylcysteine and γ-glutamyl-S-2-propenylcysteine and as S-2-propenylmercaptoglutathione on the basis of differences in key product ions identified in reference tandem MS spectra.
The ability to discriminate between such geometric isomers will be extremely useful for the chemical assignment of unknown metabolites in MS-based metabolomics.</description><subject>Chromatography, Liquid - methods</subject><subject>Cyclotrons</subject><subject>Cysteine - analysis</subject><subject>Garlic - chemistry</subject><subject>Glutathione - analysis</subject><subject>Ions - analysis</subject><subject>Isomerism</subject><subject>Metabolome</subject><subject>Metabolomics</subject><subject>Onions - chemistry</subject><subject>Spectroscopy, Fourier Transform Infrared - methods</subject><subject>Sulfur - analysis</subject><subject>Sulfur Isotopes - analysis</subject><issn>0022-3166</issn><issn>1541-6100</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kcFu1DAURS0EotPCki3yko0HO3YcZ1lFtIw0FRIt68h2XmY8iu2p7SzySfwlgSldvad7j-7mIPSJ0S1vRf31FLaMiW1FK86aN2jDasGIZJS-RRtKq4pwJuUVus75RCllolXv0VUlGyk45xv0uzuCd1ZP-DZndwgeQsFxxI8lzbbMaS12OXpI-V86T-OcSBdD0S64cMAPULSJkyuQsQv4XqfJWWwWvHfPsxtwd0zR6xIPSZ-PC7mLc3KQ8FPSIY8xebyLAXeLnWJJ6_cTcgw6WCAPOmf8eAa75h5KWj6gd6OeMnx8uTfo1923p-472f-433W3e2J5qwrRtOaNoVSCBsU4SFNLNbJGDIZrYfUAZjDayJYNNRsFtcqqeuQNt0ZpZRi_QV8uu-cUn2fIpfcuW5gmHSDOuWeNrLioWsVXlFxQm2LOCcb-nJzXaekZ7f_a6U-hX-30Fzsr__llejYehlf6vw7-B07lj5g</recordid><startdate>20160201</startdate><enddate>20160201</enddate><creator>Nakabayashi, Ryo</creator><creator>Sawada, Yuji</creator><creator>Aoyagi, Morihiro</creator><creator>Yamada, Yutaka</creator><creator>Hirai, Masami Yokota</creator><creator>Sakurai, Tetsuya</creator><creator>Kamoi, Takahiro</creator><creator>Rowan, Daryl D</creator><creator>Saito, Kazuki</creator><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>20160201</creationdate><title>Chemical Assignment of Structural Isomers of Sulfur-Containing Metabolites in Garlic by Liquid Chromatography-Fourier Transform Ion Cyclotron Resonance-Mass Spectrometry</title><author>Nakabayashi, Ryo ; Sawada, Yuji ; Aoyagi, Morihiro ; Yamada, Yutaka ; Hirai, Masami Yokota ; Sakurai, Tetsuya ; Kamoi, Takahiro ; Rowan, Daryl D ; Saito, Kazuki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c398t-a0537b006eae813e6b568f174db3a4cadebdbab691d51f40c8c85f373cb8a8b13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Chromatography, Liquid - methods</topic><topic>Cyclotrons</topic><topic>Cysteine - analysis</topic><topic>Garlic - chemistry</topic><topic>Glutathione - analysis</topic><topic>Ions - analysis</topic><topic>Isomerism</topic><topic>Metabolome</topic><topic>Metabolomics</topic><topic>Onions - chemistry</topic><topic>Spectroscopy, Fourier Transform Infrared - methods</topic><topic>Sulfur - analysis</topic><topic>Sulfur Isotopes - analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nakabayashi, Ryo</creatorcontrib><creatorcontrib>Sawada, Yuji</creatorcontrib><creatorcontrib>Aoyagi, Morihiro</creatorcontrib><creatorcontrib>Yamada, Yutaka</creatorcontrib><creatorcontrib>Hirai, Masami Yokota</creatorcontrib><creatorcontrib>Sakurai, Tetsuya</creatorcontrib><creatorcontrib>Kamoi, Takahiro</creatorcontrib><creatorcontrib>Rowan, Daryl D</creatorcontrib><creatorcontrib>Saito, Kazuki</creatorcontrib><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>The Journal of nutrition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nakabayashi, Ryo</au><au>Sawada, Yuji</au><au>Aoyagi, Morihiro</au><au>Yamada, Yutaka</au><au>Hirai, Masami Yokota</au><au>Sakurai, Tetsuya</au><au>Kamoi, Takahiro</au><au>Rowan, Daryl D</au><au>Saito, Kazuki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemical Assignment of Structural Isomers of Sulfur-Containing Metabolites in Garlic by Liquid Chromatography-Fourier Transform Ion Cyclotron Resonance-Mass Spectrometry</atitle><jtitle>The Journal of nutrition</jtitle><addtitle>J Nutr</addtitle><date>2016-02-01</date><risdate>2016</risdate><volume>146</volume><issue>2</issue><spage>397S</spage><epage>402S</epage><pages>397S-402S</pages><issn>0022-3166</issn><eissn>1541-6100</eissn><abstract>The chemical assignment of metabolites is crucial to understanding the relation between food composition and biological activity.
This study was designed to detect and chemically assign sulfur-containing metabolites by using LC-Fourier transform ion cyclotron resonance-mass spectrometry (FTICR-MS) in Allium plants.
Ultrahigh resolution (>250,000 full width at half-maximum) and mass accuracy (<1 mDa) by FTICR-MS allowed us to distinguish ions containing sulfur isotopes ((32)S and (34)S).
Putative 69 S-containing monoisotopic ions (S-ions) were extracted from the metabolome data of onion (Allium cepa), green onion (Allium fistulosum), and garlic (Allium sativum) on the basis of theoretical mass differences between (32)S-ions and their (34)S-substituted counterparts and on the natural abundance of (34)S. Eight S-ions were chemically assigned by using the reference data according to the guidelines of the Metabolomics Standards Initiative. Three ions detected in garlic were assigned as derived from the isomers γ-glutamyl-S-1-propenylcysteine and γ-glutamyl-S-2-propenylcysteine and as S-2-propenylmercaptoglutathione on the basis of differences in key product ions identified in reference tandem MS spectra.
The ability to discriminate between such geometric isomers will be extremely useful for the chemical assignment of unknown metabolites in MS-based metabolomics.</abstract><cop>United States</cop><pmid>26764333</pmid><doi>10.3945/jn.114.202317</doi><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; EZB-FREE-00999 freely available EZB journals; Alma/SFX Local Collection |
| subjects | Chromatography, Liquid - methods Cyclotrons Cysteine - analysis Garlic - chemistry Glutathione - analysis Ions - analysis Isomerism Metabolome Metabolomics Onions - chemistry Spectroscopy, Fourier Transform Infrared - methods Sulfur - analysis Sulfur Isotopes - analysis |
| title | Chemical Assignment of Structural Isomers of Sulfur-Containing Metabolites in Garlic by Liquid Chromatography-Fourier Transform Ion Cyclotron Resonance-Mass Spectrometry |
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