Multiple-Stage Tandem Mass Spectrometry for Structural Characterization of Saponins
Nanoelectrospray ion trap multiple-stage tandem mass spectrometry was applied to characterize saponins present in HPLC fractions from Quil A, a commercially available bark extract. An analytical strategy was developed based on recognition of carbohydrate sequence ions as well as glycosidic ring-cros...
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| Veröffentlicht in: | Analytical chemistry (Washington) 1998-10, Vol.70 (20), p.4401-4409 |
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| container_title | Analytical chemistry (Washington) |
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| creator | van Setten, Dirk C Jan ten Hove, G Wiertz, Emmanuel J. H. J Kamerling, Johannis P van de Werken, Gerrit |
| description | Nanoelectrospray ion trap multiple-stage tandem mass spectrometry was applied to characterize saponins present in HPLC fractions from Quil A, a commercially available bark extract. An analytical strategy was developed based on recognition of carbohydrate sequence ions as well as glycosidic ring-cross ions formed by γ-hydrogen rearrangements and successive retro-Diels−Alder fragmentations. These ions could be used for the determination of several glycosidic linkages, ring sizes, and positions of acyl groups. The presence of an acyl group on a monosaccharide residue facilitated the determination of the substitution pattern, due to the induction of ring-cross fragmentation. Deuteriomethylation resulted in a more extended set of ring-cross ions, thus allowing determination of additional glycosidic linkages. An analysis typically consumed 200 ng of sample and a total of 1−4 h for measurement and interpretation. The applied method is attractive as a pre-NMR analysis, especially because it resulted rapidly in an overall idea of the structure even when starting from scratch. The multiple-stage tandem approach enabled structural determination of saponins to a more detailed level than achievable with current single-stage tandem mass spectrometry. |
| doi_str_mv | 10.1021/ac980365q |
| format | Article |
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H. J ; Kamerling, Johannis P ; van de Werken, Gerrit</creator><creatorcontrib>van Setten, Dirk C ; Jan ten Hove, G ; Wiertz, Emmanuel J. H. J ; Kamerling, Johannis P ; van de Werken, Gerrit</creatorcontrib><description>Nanoelectrospray ion trap multiple-stage tandem mass spectrometry was applied to characterize saponins present in HPLC fractions from Quil A, a commercially available bark extract. An analytical strategy was developed based on recognition of carbohydrate sequence ions as well as glycosidic ring-cross ions formed by γ-hydrogen rearrangements and successive retro-Diels−Alder fragmentations. These ions could be used for the determination of several glycosidic linkages, ring sizes, and positions of acyl groups. The presence of an acyl group on a monosaccharide residue facilitated the determination of the substitution pattern, due to the induction of ring-cross fragmentation. Deuteriomethylation resulted in a more extended set of ring-cross ions, thus allowing determination of additional glycosidic linkages. An analysis typically consumed 200 ng of sample and a total of 1−4 h for measurement and interpretation. The applied method is attractive as a pre-NMR analysis, especially because it resulted rapidly in an overall idea of the structure even when starting from scratch. The multiple-stage tandem approach enabled structural determination of saponins to a more detailed level than achievable with current single-stage tandem mass spectrometry.</description><identifier>ISSN: 0003-2700</identifier><identifier>EISSN: 1520-6882</identifier><identifier>DOI: 10.1021/ac980365q</identifier><identifier>PMID: 9796423</identifier><identifier>CODEN: ANCHAM</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Analytical, structural and metabolic biochemistry ; Biological and medical sciences ; Carbohydrate Sequence ; Chemistry ; Chromatography, High Pressure Liquid ; Deuterium ; Fundamental and applied biological sciences. Psychology ; Ions ; Mass Spectrometry - methods ; Molecular Sequence Data ; Monosaccharides - analysis ; Other biological molecules ; Quillaja Saponins ; Reproducibility of Results ; Saponins - analysis ; Saponins - chemistry ; Scientific imaging ; Terpenes, steroids. Hormones ; Triterpenes - chemistry</subject><ispartof>Analytical chemistry (Washington), 1998-10, Vol.70 (20), p.4401-4409</ispartof><rights>Copyright © 1998 American Chemical Society</rights><rights>1998 INIST-CNRS</rights><rights>Copyright American Chemical Society Oct 15, 1998</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a470t-67ba8e4b3b84db5c1c91acea5ccbb3e930626938f4e1df8e11d1176cc5889c8e3</citedby><cites>FETCH-LOGICAL-a470t-67ba8e4b3b84db5c1c91acea5ccbb3e930626938f4e1df8e11d1176cc5889c8e3</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/ac980365q$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ac980365q$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2441400$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9796423$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>van Setten, Dirk C</creatorcontrib><creatorcontrib>Jan ten Hove, G</creatorcontrib><creatorcontrib>Wiertz, Emmanuel J. H. J</creatorcontrib><creatorcontrib>Kamerling, Johannis P</creatorcontrib><creatorcontrib>van de Werken, Gerrit</creatorcontrib><title>Multiple-Stage Tandem Mass Spectrometry for Structural Characterization of Saponins</title><title>Analytical chemistry (Washington)</title><addtitle>Anal. Chem</addtitle><description>Nanoelectrospray ion trap multiple-stage tandem mass spectrometry was applied to characterize saponins present in HPLC fractions from Quil A, a commercially available bark extract. An analytical strategy was developed based on recognition of carbohydrate sequence ions as well as glycosidic ring-cross ions formed by γ-hydrogen rearrangements and successive retro-Diels−Alder fragmentations. These ions could be used for the determination of several glycosidic linkages, ring sizes, and positions of acyl groups. The presence of an acyl group on a monosaccharide residue facilitated the determination of the substitution pattern, due to the induction of ring-cross fragmentation. Deuteriomethylation resulted in a more extended set of ring-cross ions, thus allowing determination of additional glycosidic linkages. An analysis typically consumed 200 ng of sample and a total of 1−4 h for measurement and interpretation. The applied method is attractive as a pre-NMR analysis, especially because it resulted rapidly in an overall idea of the structure even when starting from scratch. The multiple-stage tandem approach enabled structural determination of saponins to a more detailed level than achievable with current single-stage tandem mass spectrometry.</description><subject>Analytical, structural and metabolic biochemistry</subject><subject>Biological and medical sciences</subject><subject>Carbohydrate Sequence</subject><subject>Chemistry</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Deuterium</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Ions</subject><subject>Mass Spectrometry - methods</subject><subject>Molecular Sequence Data</subject><subject>Monosaccharides - analysis</subject><subject>Other biological molecules</subject><subject>Quillaja Saponins</subject><subject>Reproducibility of Results</subject><subject>Saponins - analysis</subject><subject>Saponins - chemistry</subject><subject>Scientific imaging</subject><subject>Terpenes, steroids. 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H. J ; Kamerling, Johannis P ; van de Werken, Gerrit</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a470t-67ba8e4b3b84db5c1c91acea5ccbb3e930626938f4e1df8e11d1176cc5889c8e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>Analytical, structural and metabolic biochemistry</topic><topic>Biological and medical sciences</topic><topic>Carbohydrate Sequence</topic><topic>Chemistry</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Deuterium</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Ions</topic><topic>Mass Spectrometry - methods</topic><topic>Molecular Sequence Data</topic><topic>Monosaccharides - analysis</topic><topic>Other biological molecules</topic><topic>Quillaja Saponins</topic><topic>Reproducibility of Results</topic><topic>Saponins - analysis</topic><topic>Saponins - chemistry</topic><topic>Scientific imaging</topic><topic>Terpenes, steroids. Hormones</topic><topic>Triterpenes - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>van Setten, Dirk C</creatorcontrib><creatorcontrib>Jan ten Hove, G</creatorcontrib><creatorcontrib>Wiertz, Emmanuel J. H. 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H. J</au><au>Kamerling, Johannis P</au><au>van de Werken, Gerrit</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Multiple-Stage Tandem Mass Spectrometry for Structural Characterization of Saponins</atitle><jtitle>Analytical chemistry (Washington)</jtitle><addtitle>Anal. Chem</addtitle><date>1998-10-15</date><risdate>1998</risdate><volume>70</volume><issue>20</issue><spage>4401</spage><epage>4409</epage><pages>4401-4409</pages><issn>0003-2700</issn><eissn>1520-6882</eissn><coden>ANCHAM</coden><abstract>Nanoelectrospray ion trap multiple-stage tandem mass spectrometry was applied to characterize saponins present in HPLC fractions from Quil A, a commercially available bark extract. An analytical strategy was developed based on recognition of carbohydrate sequence ions as well as glycosidic ring-cross ions formed by γ-hydrogen rearrangements and successive retro-Diels−Alder fragmentations. These ions could be used for the determination of several glycosidic linkages, ring sizes, and positions of acyl groups. The presence of an acyl group on a monosaccharide residue facilitated the determination of the substitution pattern, due to the induction of ring-cross fragmentation. Deuteriomethylation resulted in a more extended set of ring-cross ions, thus allowing determination of additional glycosidic linkages. An analysis typically consumed 200 ng of sample and a total of 1−4 h for measurement and interpretation. The applied method is attractive as a pre-NMR analysis, especially because it resulted rapidly in an overall idea of the structure even when starting from scratch. The multiple-stage tandem approach enabled structural determination of saponins to a more detailed level than achievable with current single-stage tandem mass spectrometry.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>9796423</pmid><doi>10.1021/ac980365q</doi><tpages>9</tpages></addata></record> |
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| subjects | Analytical, structural and metabolic biochemistry Biological and medical sciences Carbohydrate Sequence Chemistry Chromatography, High Pressure Liquid Deuterium Fundamental and applied biological sciences. Psychology Ions Mass Spectrometry - methods Molecular Sequence Data Monosaccharides - analysis Other biological molecules Quillaja Saponins Reproducibility of Results Saponins - analysis Saponins - chemistry Scientific imaging Terpenes, steroids. Hormones Triterpenes - chemistry |
| title | Multiple-Stage Tandem Mass Spectrometry for Structural Characterization of Saponins |
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