Electrospray ionization Fourier transform ion cyclotron resonance mass spectrometric and semi-empirical calculations study of five isoflavone aglycones
Five isoflavones, daidzein, genistein, formononetin, prunetin and biochanin A, known for their biological properties, are investigated by electrospray ionization mass spectrometry in the positive ion mode. The most probable protonation sites are determined taking into account semi‐empirical calculat...
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| Veröffentlicht in: | Rapid communications in mass spectrometry 2010-12, Vol.24 (23), p.3432-3440 |
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| creator | Madeira, Paulo J. Amorim Borges, Carlos M. Florêncio, M. Helena |
| description | Five isoflavones, daidzein, genistein, formononetin, prunetin and biochanin A, known for their biological properties, are investigated by electrospray ionization mass spectrometry in the positive ion mode. The most probable protonation sites are determined taking into account semi‐empirical calculations using the PM6 Hamiltonian. Fragmentation mechanisms are proposed based on accurate mass measurements, MS3 experiments and supported by the semi‐empirical calculations. Some of the fragmentation pathways were found to be dependent on the substitution pattern of the B‐ring and the ions afforded by these fragmentations can be considered as diagnostic. It was possible to distinguish between prunetin and biochanin A, two isobaric isoflavone aglycones included in this study. Furthermore, a comparison of the fragmentation patterns of genistein and biochanin A, two isoflavones, with those of their flavone counterparts, apigenin and acacetin, enabled us to identify some key ions mainly due to structural features, allowing distinction to be made between these two classes of compounds. Copyright © 2010 John Wiley & Sons, Ltd. |
| doi_str_mv | 10.1002/rcm.4791 |
| format | Article |
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Amorim ; Borges, Carlos M. ; Florêncio, M. Helena</creator><creatorcontrib>Madeira, Paulo J. Amorim ; Borges, Carlos M. ; Florêncio, M. Helena</creatorcontrib><description>Five isoflavones, daidzein, genistein, formononetin, prunetin and biochanin A, known for their biological properties, are investigated by electrospray ionization mass spectrometry in the positive ion mode. The most probable protonation sites are determined taking into account semi‐empirical calculations using the PM6 Hamiltonian. Fragmentation mechanisms are proposed based on accurate mass measurements, MS3 experiments and supported by the semi‐empirical calculations. Some of the fragmentation pathways were found to be dependent on the substitution pattern of the B‐ring and the ions afforded by these fragmentations can be considered as diagnostic. It was possible to distinguish between prunetin and biochanin A, two isobaric isoflavone aglycones included in this study. Furthermore, a comparison of the fragmentation patterns of genistein and biochanin A, two isoflavones, with those of their flavone counterparts, apigenin and acacetin, enabled us to identify some key ions mainly due to structural features, allowing distinction to be made between these two classes of compounds. 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Amorim</creatorcontrib><creatorcontrib>Borges, Carlos M.</creatorcontrib><creatorcontrib>Florêncio, M. Helena</creatorcontrib><title>Electrospray ionization Fourier transform ion cyclotron resonance mass spectrometric and semi-empirical calculations study of five isoflavone aglycones</title><title>Rapid communications in mass spectrometry</title><addtitle>Rapid Commun. Mass Spectrom</addtitle><description>Five isoflavones, daidzein, genistein, formononetin, prunetin and biochanin A, known for their biological properties, are investigated by electrospray ionization mass spectrometry in the positive ion mode. The most probable protonation sites are determined taking into account semi‐empirical calculations using the PM6 Hamiltonian. Fragmentation mechanisms are proposed based on accurate mass measurements, MS3 experiments and supported by the semi‐empirical calculations. Some of the fragmentation pathways were found to be dependent on the substitution pattern of the B‐ring and the ions afforded by these fragmentations can be considered as diagnostic. It was possible to distinguish between prunetin and biochanin A, two isobaric isoflavone aglycones included in this study. Furthermore, a comparison of the fragmentation patterns of genistein and biochanin A, two isoflavones, with those of their flavone counterparts, apigenin and acacetin, enabled us to identify some key ions mainly due to structural features, allowing distinction to be made between these two classes of compounds. Copyright © 2010 John Wiley & Sons, Ltd.</description><subject>Cyclotron resonance</subject><subject>Cyclotrons</subject><subject>Diagnostic systems</subject><subject>Fourier Analysis</subject><subject>Fourier transforms</subject><subject>Fragmentation</subject><subject>Ionization</subject><subject>Isoflavones</subject><subject>Isoflavones - chemistry</subject><subject>Mass spectrometry</subject><subject>Mathematical analysis</subject><subject>Molecular Structure</subject><subject>Molecular Weight</subject><subject>Spectrometry, Mass, Electrospray Ionization - instrumentation</subject><subject>Spectrometry, Mass, Electrospray Ionization - methods</subject><issn>0951-4198</issn><issn>1097-0231</issn><issn>1097-0231</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU1v1DAQhi0EoktB4hcg3-CS4nE-nBzRqrsgtSDxIY6W44yRwY6DnRTCH-Hv4u0uvSEOoxnZj56R_RLyFNgFMMZfRu0vKtHBPbIB1omC8RLukw3raigq6Noz8iilr4wB1Jw9JGccmOCi6zbk96VDPceQpqhWasNof6k5N7oLS7QY6RzVmEyI_nBJ9apdyPhII6YwqlEj9SolmqZbjcc5Wk3VONCE3hboJ5sPlKO59OJu3Zmel2GlwVBjb5DaFIxTN2FEqr64VechPSYPjHIJn5z6Ofm0u_y4fV1cvdu_2b66KnTZsfy4gQ0MWj60pmetEhqgV4x3BqEHjiVUjVHQ9AZb3tbYdKpWJYAAwVsxCCzPyfOjd4rh-4Jplt4mjc6pEcOSZF7SNEJU_L-kaKq6YlBCJl8cSZ3_NUU0corWq7hKYPKQl8x5yUNeGX12ki69x-EO_BtQBooj8MM6XP8pku-31yfhibdpxp93vIrfZCNKUcvPb_dyf13tdx9aLqH8A87Jse0</recordid><startdate>20101215</startdate><enddate>20101215</enddate><creator>Madeira, Paulo J. Amorim</creator><creator>Borges, Carlos M.</creator><creator>Florêncio, M. Helena</creator><general>John Wiley & Sons, Ltd</general><scope>BSCLL</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><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20101215</creationdate><title>Electrospray ionization Fourier transform ion cyclotron resonance mass spectrometric and semi-empirical calculations study of five isoflavone aglycones</title><author>Madeira, Paulo J. Amorim ; Borges, Carlos M. ; Florêncio, M. Helena</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3901-4d0d0182d8fb08a7c11ba029fe1b12e3146fa16bfe8285e69a5a311717287d7e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Cyclotron resonance</topic><topic>Cyclotrons</topic><topic>Diagnostic systems</topic><topic>Fourier Analysis</topic><topic>Fourier transforms</topic><topic>Fragmentation</topic><topic>Ionization</topic><topic>Isoflavones</topic><topic>Isoflavones - chemistry</topic><topic>Mass spectrometry</topic><topic>Mathematical analysis</topic><topic>Molecular Structure</topic><topic>Molecular Weight</topic><topic>Spectrometry, Mass, Electrospray Ionization - instrumentation</topic><topic>Spectrometry, Mass, Electrospray Ionization - methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Madeira, Paulo J. Amorim</creatorcontrib><creatorcontrib>Borges, Carlos M.</creatorcontrib><creatorcontrib>Florêncio, M. Helena</creatorcontrib><collection>Istex</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><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Rapid communications in mass spectrometry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Madeira, Paulo J. 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Fragmentation mechanisms are proposed based on accurate mass measurements, MS3 experiments and supported by the semi‐empirical calculations. Some of the fragmentation pathways were found to be dependent on the substitution pattern of the B‐ring and the ions afforded by these fragmentations can be considered as diagnostic. It was possible to distinguish between prunetin and biochanin A, two isobaric isoflavone aglycones included in this study. Furthermore, a comparison of the fragmentation patterns of genistein and biochanin A, two isoflavones, with those of their flavone counterparts, apigenin and acacetin, enabled us to identify some key ions mainly due to structural features, allowing distinction to be made between these two classes of compounds. Copyright © 2010 John Wiley & Sons, Ltd.</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Ltd</pub><pmid>21072799</pmid><doi>10.1002/rcm.4791</doi><tpages>9</tpages></addata></record> |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Cyclotron resonance Cyclotrons Diagnostic systems Fourier Analysis Fourier transforms Fragmentation Ionization Isoflavones Isoflavones - chemistry Mass spectrometry Mathematical analysis Molecular Structure Molecular Weight Spectrometry, Mass, Electrospray Ionization - instrumentation Spectrometry, Mass, Electrospray Ionization - methods |
| title | Electrospray ionization Fourier transform ion cyclotron resonance mass spectrometric and semi-empirical calculations study of five isoflavone aglycones |
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