Characterization of C-glycosyl flavones O-glycosylated by liquid chromatography–tandem mass spectrometry
Fifty three O-glycosyl- C-glycosyl flavones with O-glycosylation on phenolic hydroxyl or on the C-glycosyl residue or combination of both forms have been studied by liquid chromatography-UV diode array detection-electrospray ionisation mass spectrometry ion trap in the negative mode. The study of th...
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| creator | Ferreres, F. Gil-Izquierdo, A. Andrade, P.B. Valentão, P. Tomás-Barberán, F.A. |
| description | Fifty three
O-glycosyl-
C-glycosyl flavones with
O-glycosylation on phenolic hydroxyl or on the
C-glycosyl residue or combination of both forms have been studied by liquid chromatography-UV diode array detection-electrospray ionisation mass spectrometry ion trap in the negative mode. The study of the relative abundance of the main ions from the MS preferential fragmentation on
–MS2 and/or
–MS3 events allows the differentiation of the position of the
O-glycosylation, either on phenolic hydroxyl or on the sugar moiety of
C-glycosylation. In addition, it is possible to discriminate between
O-glycosylation at 2″ and at 6″ positions. The occurrence of an abundant ion
Y
0
−
([(
M
−
H
)
-132/-146/-162]
−, mono-
O-pentosyl/rhamnosyl/hexosyl-
C-glycosyl derivatives) after
–MS2 fragmentation characterizes the
O-glycosylation on phenolic hydroxyls. The preferential fragmentation leading to a relevant
Z
1
−
(
[Y
1
-18]
−) fragment is characteristic of 2″-
O-glycosyl-
C-glycosyl derivatives. The 6″-
O-glycosyl-
C-glycosyl derivatives are characterized by
0,2
X
0
−
, which is generated by a global loss of the sugar moiety from the
O-glycosylation at 6″ and the glycosidic fraction that involves the carbons 6″-3″ of the
C-glycosyl residue (
[(
M
−
H
)
-162-120]
−
, in the case of 6″-
O-hexosyl-
C-hexosyl derivatives). Regarding the combined
O-glycosylated compounds (both on phenolic hydroxyl and on sugar moiety at
C-glycosylation), the main fragmentation on
–MS2 events produces a
Y
0
−
characterizing the
O-glycosylation on the phenolic hydroxyl, and the –
MS3[(
M
−
H
)
→
Y
0
]
− fragmentation of the
O-glycosylation on the
C-glycosyl residue. |
| doi_str_mv | 10.1016/j.chroma.2007.05.103 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_68096824</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0021967307009922</els_id><sourcerecordid>68096824</sourcerecordid><originalsourceid>FETCH-LOGICAL-c480t-623325499a9e0ceef2ab6e1e469bf4a6ee88ab25dea95b1719cd04ba39c1cc73</originalsourceid><addsrcrecordid>eNp9kM1u1DAURr0A0VJ4AwTewC7Ta8dx4g0SGlFAqtRF27V149zMeJTEUztTKax4B96QJ2lGGdFdV5Y-n_t3GPsgYCVA6Mvdym1j6HElAcoVFHOav2LnAFJkRpf5GXub0g5AlFDKN-xMlBqkNsU52623GNGNFP1vHH0YeGj5Ott0kwtp6njb4WMYKPGb_xmO1PB64p1_OPiGL5PHsIm4307__vwdcWio5z2mxNOe3Dj_0xind-x1i12i96f3gt1dfb9b_8yub378Wn-7zpyqYMy0zHNZKGPQEDiiVmKtSZDSpm4VaqKqwloWDaEpalEK4xpQNebGCefK_IJ9WdruY3g4UBpt75OjrsOBwiFZXYHRlVQzqBbQxZBSpNbuo-8xTlaAPWq1O7scZ49aLRRzms9lH0_9D3VPzXPRyekMfD4BmBx2bcTB-fTMVaYotDrO_7RwLQaLmzgz97cSRA5QKSXK4ylfF4JmXY-eok3O0-Co8XH2apvgX971CSaFp1A</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>68096824</pqid></control><display><type>article</type><title>Characterization of C-glycosyl flavones O-glycosylated by liquid chromatography–tandem mass spectrometry</title><source>MEDLINE</source><source>ScienceDirect Journals (5 years ago - present)</source><creator>Ferreres, F. ; Gil-Izquierdo, A. ; Andrade, P.B. ; Valentão, P. ; Tomás-Barberán, F.A.</creator><creatorcontrib>Ferreres, F. ; Gil-Izquierdo, A. ; Andrade, P.B. ; Valentão, P. ; Tomás-Barberán, F.A.</creatorcontrib><description>Fifty three
O-glycosyl-
C-glycosyl flavones with
O-glycosylation on phenolic hydroxyl or on the
C-glycosyl residue or combination of both forms have been studied by liquid chromatography-UV diode array detection-electrospray ionisation mass spectrometry ion trap in the negative mode. The study of the relative abundance of the main ions from the MS preferential fragmentation on
–MS2 and/or
–MS3 events allows the differentiation of the position of the
O-glycosylation, either on phenolic hydroxyl or on the sugar moiety of
C-glycosylation. In addition, it is possible to discriminate between
O-glycosylation at 2″ and at 6″ positions. The occurrence of an abundant ion
Y
0
−
([(
M
−
H
)
-132/-146/-162]
−, mono-
O-pentosyl/rhamnosyl/hexosyl-
C-glycosyl derivatives) after
–MS2 fragmentation characterizes the
O-glycosylation on phenolic hydroxyls. The preferential fragmentation leading to a relevant
Z
1
−
(
[Y
1
-18]
−) fragment is characteristic of 2″-
O-glycosyl-
C-glycosyl derivatives. The 6″-
O-glycosyl-
C-glycosyl derivatives are characterized by
0,2
X
0
−
, which is generated by a global loss of the sugar moiety from the
O-glycosylation at 6″ and the glycosidic fraction that involves the carbons 6″-3″ of the
C-glycosyl residue (
[(
M
−
H
)
-162-120]
−
, in the case of 6″-
O-hexosyl-
C-hexosyl derivatives). Regarding the combined
O-glycosylated compounds (both on phenolic hydroxyl and on sugar moiety at
C-glycosylation), the main fragmentation on
–MS2 events produces a
Y
0
−
characterizing the
O-glycosylation on the phenolic hydroxyl, and the –
MS3[(
M
−
H
)
→
Y
0
]
− fragmentation of the
O-glycosylation on the
C-glycosyl residue.</description><identifier>ISSN: 0021-9673</identifier><identifier>DOI: 10.1016/j.chroma.2007.05.103</identifier><identifier>PMID: 17602695</identifier><identifier>CODEN: JOCRAM</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Agronomy. Soil science and plant productions ; Avena sativa ; Beta vulgaris ; Biological and medical sciences ; Briza media ; Chemical constitution ; chemical structure ; Chromatography, Liquid - methods ; Economic plant physiology ; flavones ; Flavones - chemistry ; Fundamental and applied biological sciences. Psychology ; General pharmacology ; Glycosylation ; Gypsophila paniculata ; liquid chromatography ; Mass spectrometry ; Medical sciences ; O-Glycosyl- C-glycosyl flavones ; Passiflora incarnata ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; plant extracts ; Rumex induratus ; Spectrometry, Mass, Electrospray Ionization - methods ; Tandem Mass Spectrometry - methods ; Triticum aestivum ; ultraviolet radiation diode array detection</subject><ispartof>Journal of Chromatography A, 2007-08, Vol.1161 (1), p.214-223</ispartof><rights>2007 Elsevier B.V.</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c480t-623325499a9e0ceef2ab6e1e469bf4a6ee88ab25dea95b1719cd04ba39c1cc73</citedby><cites>FETCH-LOGICAL-c480t-623325499a9e0ceef2ab6e1e469bf4a6ee88ab25dea95b1719cd04ba39c1cc73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.chroma.2007.05.103$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3549,27923,27924,45994</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18955644$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17602695$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ferreres, F.</creatorcontrib><creatorcontrib>Gil-Izquierdo, A.</creatorcontrib><creatorcontrib>Andrade, P.B.</creatorcontrib><creatorcontrib>Valentão, P.</creatorcontrib><creatorcontrib>Tomás-Barberán, F.A.</creatorcontrib><title>Characterization of C-glycosyl flavones O-glycosylated by liquid chromatography–tandem mass spectrometry</title><title>Journal of Chromatography A</title><addtitle>J Chromatogr A</addtitle><description>Fifty three
O-glycosyl-
C-glycosyl flavones with
O-glycosylation on phenolic hydroxyl or on the
C-glycosyl residue or combination of both forms have been studied by liquid chromatography-UV diode array detection-electrospray ionisation mass spectrometry ion trap in the negative mode. The study of the relative abundance of the main ions from the MS preferential fragmentation on
–MS2 and/or
–MS3 events allows the differentiation of the position of the
O-glycosylation, either on phenolic hydroxyl or on the sugar moiety of
C-glycosylation. In addition, it is possible to discriminate between
O-glycosylation at 2″ and at 6″ positions. The occurrence of an abundant ion
Y
0
−
([(
M
−
H
)
-132/-146/-162]
−, mono-
O-pentosyl/rhamnosyl/hexosyl-
C-glycosyl derivatives) after
–MS2 fragmentation characterizes the
O-glycosylation on phenolic hydroxyls. The preferential fragmentation leading to a relevant
Z
1
−
(
[Y
1
-18]
−) fragment is characteristic of 2″-
O-glycosyl-
C-glycosyl derivatives. The 6″-
O-glycosyl-
C-glycosyl derivatives are characterized by
0,2
X
0
−
, which is generated by a global loss of the sugar moiety from the
O-glycosylation at 6″ and the glycosidic fraction that involves the carbons 6″-3″ of the
C-glycosyl residue (
[(
M
−
H
)
-162-120]
−
, in the case of 6″-
O-hexosyl-
C-hexosyl derivatives). Regarding the combined
O-glycosylated compounds (both on phenolic hydroxyl and on sugar moiety at
C-glycosylation), the main fragmentation on
–MS2 events produces a
Y
0
−
characterizing the
O-glycosylation on the phenolic hydroxyl, and the –
MS3[(
M
−
H
)
→
Y
0
]
− fragmentation of the
O-glycosylation on the
C-glycosyl residue.</description><subject>Agronomy. Soil science and plant productions</subject><subject>Avena sativa</subject><subject>Beta vulgaris</subject><subject>Biological and medical sciences</subject><subject>Briza media</subject><subject>Chemical constitution</subject><subject>chemical structure</subject><subject>Chromatography, Liquid - methods</subject><subject>Economic plant physiology</subject><subject>flavones</subject><subject>Flavones - chemistry</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General pharmacology</subject><subject>Glycosylation</subject><subject>Gypsophila paniculata</subject><subject>liquid chromatography</subject><subject>Mass spectrometry</subject><subject>Medical sciences</subject><subject>O-Glycosyl- C-glycosyl flavones</subject><subject>Passiflora incarnata</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>plant extracts</subject><subject>Rumex induratus</subject><subject>Spectrometry, Mass, Electrospray Ionization - methods</subject><subject>Tandem Mass Spectrometry - methods</subject><subject>Triticum aestivum</subject><subject>ultraviolet radiation diode array detection</subject><issn>0021-9673</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kM1u1DAURr0A0VJ4AwTewC7Ta8dx4g0SGlFAqtRF27V149zMeJTEUztTKax4B96QJ2lGGdFdV5Y-n_t3GPsgYCVA6Mvdym1j6HElAcoVFHOav2LnAFJkRpf5GXub0g5AlFDKN-xMlBqkNsU52623GNGNFP1vHH0YeGj5Ott0kwtp6njb4WMYKPGb_xmO1PB64p1_OPiGL5PHsIm4307__vwdcWio5z2mxNOe3Dj_0xind-x1i12i96f3gt1dfb9b_8yub378Wn-7zpyqYMy0zHNZKGPQEDiiVmKtSZDSpm4VaqKqwloWDaEpalEK4xpQNebGCefK_IJ9WdruY3g4UBpt75OjrsOBwiFZXYHRlVQzqBbQxZBSpNbuo-8xTlaAPWq1O7scZ49aLRRzms9lH0_9D3VPzXPRyekMfD4BmBx2bcTB-fTMVaYotDrO_7RwLQaLmzgz97cSRA5QKSXK4ylfF4JmXY-eok3O0-Co8XH2apvgX971CSaFp1A</recordid><startdate>20070817</startdate><enddate>20070817</enddate><creator>Ferreres, F.</creator><creator>Gil-Izquierdo, A.</creator><creator>Andrade, P.B.</creator><creator>Valentão, P.</creator><creator>Tomás-Barberán, F.A.</creator><general>Elsevier B.V</general><general>Elsevier</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>20070817</creationdate><title>Characterization of C-glycosyl flavones O-glycosylated by liquid chromatography–tandem mass spectrometry</title><author>Ferreres, F. ; Gil-Izquierdo, A. ; Andrade, P.B. ; Valentão, P. ; Tomás-Barberán, F.A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c480t-623325499a9e0ceef2ab6e1e469bf4a6ee88ab25dea95b1719cd04ba39c1cc73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Agronomy. Soil science and plant productions</topic><topic>Avena sativa</topic><topic>Beta vulgaris</topic><topic>Biological and medical sciences</topic><topic>Briza media</topic><topic>Chemical constitution</topic><topic>chemical structure</topic><topic>Chromatography, Liquid - methods</topic><topic>Economic plant physiology</topic><topic>flavones</topic><topic>Flavones - chemistry</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General pharmacology</topic><topic>Glycosylation</topic><topic>Gypsophila paniculata</topic><topic>liquid chromatography</topic><topic>Mass spectrometry</topic><topic>Medical sciences</topic><topic>O-Glycosyl- C-glycosyl flavones</topic><topic>Passiflora incarnata</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>plant extracts</topic><topic>Rumex induratus</topic><topic>Spectrometry, Mass, Electrospray Ionization - methods</topic><topic>Tandem Mass Spectrometry - methods</topic><topic>Triticum aestivum</topic><topic>ultraviolet radiation diode array detection</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ferreres, F.</creatorcontrib><creatorcontrib>Gil-Izquierdo, A.</creatorcontrib><creatorcontrib>Andrade, P.B.</creatorcontrib><creatorcontrib>Valentão, P.</creatorcontrib><creatorcontrib>Tomás-Barberán, F.A.</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>Journal of Chromatography A</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ferreres, F.</au><au>Gil-Izquierdo, A.</au><au>Andrade, P.B.</au><au>Valentão, P.</au><au>Tomás-Barberán, F.A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Characterization of C-glycosyl flavones O-glycosylated by liquid chromatography–tandem mass spectrometry</atitle><jtitle>Journal of Chromatography A</jtitle><addtitle>J Chromatogr A</addtitle><date>2007-08-17</date><risdate>2007</risdate><volume>1161</volume><issue>1</issue><spage>214</spage><epage>223</epage><pages>214-223</pages><issn>0021-9673</issn><coden>JOCRAM</coden><abstract>Fifty three
O-glycosyl-
C-glycosyl flavones with
O-glycosylation on phenolic hydroxyl or on the
C-glycosyl residue or combination of both forms have been studied by liquid chromatography-UV diode array detection-electrospray ionisation mass spectrometry ion trap in the negative mode. The study of the relative abundance of the main ions from the MS preferential fragmentation on
–MS2 and/or
–MS3 events allows the differentiation of the position of the
O-glycosylation, either on phenolic hydroxyl or on the sugar moiety of
C-glycosylation. In addition, it is possible to discriminate between
O-glycosylation at 2″ and at 6″ positions. The occurrence of an abundant ion
Y
0
−
([(
M
−
H
)
-132/-146/-162]
−, mono-
O-pentosyl/rhamnosyl/hexosyl-
C-glycosyl derivatives) after
–MS2 fragmentation characterizes the
O-glycosylation on phenolic hydroxyls. The preferential fragmentation leading to a relevant
Z
1
−
(
[Y
1
-18]
−) fragment is characteristic of 2″-
O-glycosyl-
C-glycosyl derivatives. The 6″-
O-glycosyl-
C-glycosyl derivatives are characterized by
0,2
X
0
−
, which is generated by a global loss of the sugar moiety from the
O-glycosylation at 6″ and the glycosidic fraction that involves the carbons 6″-3″ of the
C-glycosyl residue (
[(
M
−
H
)
-162-120]
−
, in the case of 6″-
O-hexosyl-
C-hexosyl derivatives). Regarding the combined
O-glycosylated compounds (both on phenolic hydroxyl and on sugar moiety at
C-glycosylation), the main fragmentation on
–MS2 events produces a
Y
0
−
characterizing the
O-glycosylation on the phenolic hydroxyl, and the –
MS3[(
M
−
H
)
→
Y
0
]
− fragmentation of the
O-glycosylation on the
C-glycosyl residue.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><pmid>17602695</pmid><doi>10.1016/j.chroma.2007.05.103</doi><tpages>10</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0021-9673 |
| ispartof | Journal of Chromatography A, 2007-08, Vol.1161 (1), p.214-223 |
| issn | 0021-9673 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_68096824 |
| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Agronomy. Soil science and plant productions Avena sativa Beta vulgaris Biological and medical sciences Briza media Chemical constitution chemical structure Chromatography, Liquid - methods Economic plant physiology flavones Flavones - chemistry Fundamental and applied biological sciences. Psychology General pharmacology Glycosylation Gypsophila paniculata liquid chromatography Mass spectrometry Medical sciences O-Glycosyl- C-glycosyl flavones Passiflora incarnata Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments plant extracts Rumex induratus Spectrometry, Mass, Electrospray Ionization - methods Tandem Mass Spectrometry - methods Triticum aestivum ultraviolet radiation diode array detection |
| title | Characterization of C-glycosyl flavones O-glycosylated by liquid chromatography–tandem mass spectrometry |
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