Bin Huang, Fangjun Chen, Xiang Zhang, Yanzhen Hu, Yuanyuan Zhang, Le Chen, Yan Meng, Ping Wen
{"title":"利用三重四极杆质谱对双糖黄酮 C-糖苷的片段研究及其在鉴定小柴胡中黄酮 C-糖苷中的应用。","authors":"Bin Huang, Fangjun Chen, Xiang Zhang, Yanzhen Hu, Yuanyuan Zhang, Le Chen, Yan Meng, Ping Wen","doi":"10.1002/rcm.9936","DOIUrl":null,"url":null,"abstract":"<div>\n \n <section>\n \n <h3> Rationale</h3>\n \n <p>Flavonoid C-glycosides have a wide range of pharmacological activities. However, there are few mass spectrometric research on C,O-disaccharide flavonoid C-glycosides and di-C,O-saccharide flavonoid C-glycosides. Their low-energy collision-induced dissociation (ESI-CID-MS/MS) fragmentation pattern and differences have not been reported, and the fragment ion library is incomplete. Therefore, it was essential to elucidate the fragmentation patterns of disaccharide flavonoid C-glycosides, which is described in this study.</p>\n </section>\n \n <section>\n \n <h3> Methods</h3>\n \n <p>Four disaccharide flavonoid C-glycosides such as vitexin-4″-<i>O</i>-glucoside were analyzed by ultra-performance liquid chromatography-triple quadrupole tandem mass spectrometer (UPLC-MS/MS) using electrospray ionization (ESI) in both positive and negative ion modes. Each ion and its proposed fragmentation pathways of the four disaccharide flavonoid C-glycosides were analyzed comprehensively. Finally, ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS/MS) and the established fragmentation patterns have been used to identify disaccharide flavonoid C-glycosides in <i>Odontosoria Chinensis</i>.</p>\n </section>\n \n <section>\n \n <h3> Results</h3>\n \n <p>The fragmentation pathways of C,O-disaccharide flavonoid C-glycosides and di-C,O-saccharide flavonoid C-glycosides are similar. They both have the mass spectrometric characteristics of O-glycoside and C-glycoside. Product ions after mixed pathways of neutral fragments such as saccharide ring fragment, O-glycosides, H<sub>2</sub>O, and CH<sub>2</sub>O elimination appeared in both types of flavonoid C-glycosides, but their relative abundances are significantly different. According to the established fragmentation patterns, di-C,O-saccharide flavonoid glycosides were also found in <i>Odontosoria chinensis</i>.</p>\n </section>\n \n <section>\n \n <h3> Conclusion</h3>\n \n <p>The fragment ions at <i>m</i>/<i>z</i> 431, 413, 341, 311, 293, and 282 in negative ion mode and <i>m</i>/<i>z</i> 293, 282, 577, 559, 541, 523, 529, and 499 in positive ion mode can serves as the main characteristics for identifying C,O-disaccharide flavonoid C-glycosides and di-C,O-saccharide flavonoid C-glycosides.</p>\n </section>\n </div>","PeriodicalId":225,"journal":{"name":"Rapid Communications in Mass Spectrometry","volume":"39 2","pages":""},"PeriodicalIF":1.8000,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A fragmentation study of disaccharide flavonoid C-glycosides using triple quadrupole mass spectrometry and its application for identification of flavonoid C-glycosides in Odontosoria chinensis\",\"authors\":\"Bin Huang, Fangjun Chen, Xiang Zhang, Yanzhen Hu, Yuanyuan Zhang, Le Chen, Yan Meng, Ping Wen\",\"doi\":\"10.1002/rcm.9936\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div>\\n \\n <section>\\n \\n <h3> Rationale</h3>\\n \\n <p>Flavonoid C-glycosides have a wide range of pharmacological activities. However, there are few mass spectrometric research on C,O-disaccharide flavonoid C-glycosides and di-C,O-saccharide flavonoid C-glycosides. Their low-energy collision-induced dissociation (ESI-CID-MS/MS) fragmentation pattern and differences have not been reported, and the fragment ion library is incomplete. Therefore, it was essential to elucidate the fragmentation patterns of disaccharide flavonoid C-glycosides, which is described in this study.</p>\\n </section>\\n \\n <section>\\n \\n <h3> Methods</h3>\\n \\n <p>Four disaccharide flavonoid C-glycosides such as vitexin-4″-<i>O</i>-glucoside were analyzed by ultra-performance liquid chromatography-triple quadrupole tandem mass spectrometer (UPLC-MS/MS) using electrospray ionization (ESI) in both positive and negative ion modes. Each ion and its proposed fragmentation pathways of the four disaccharide flavonoid C-glycosides were analyzed comprehensively. Finally, ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS/MS) and the established fragmentation patterns have been used to identify disaccharide flavonoid C-glycosides in <i>Odontosoria Chinensis</i>.</p>\\n </section>\\n \\n <section>\\n \\n <h3> Results</h3>\\n \\n <p>The fragmentation pathways of C,O-disaccharide flavonoid C-glycosides and di-C,O-saccharide flavonoid C-glycosides are similar. They both have the mass spectrometric characteristics of O-glycoside and C-glycoside. Product ions after mixed pathways of neutral fragments such as saccharide ring fragment, O-glycosides, H<sub>2</sub>O, and CH<sub>2</sub>O elimination appeared in both types of flavonoid C-glycosides, but their relative abundances are significantly different. According to the established fragmentation patterns, di-C,O-saccharide flavonoid glycosides were also found in <i>Odontosoria chinensis</i>.</p>\\n </section>\\n \\n <section>\\n \\n <h3> Conclusion</h3>\\n \\n <p>The fragment ions at <i>m</i>/<i>z</i> 431, 413, 341, 311, 293, and 282 in negative ion mode and <i>m</i>/<i>z</i> 293, 282, 577, 559, 541, 523, 529, and 499 in positive ion mode can serves as the main characteristics for identifying C,O-disaccharide flavonoid C-glycosides and di-C,O-saccharide flavonoid C-glycosides.</p>\\n </section>\\n </div>\",\"PeriodicalId\":225,\"journal\":{\"name\":\"Rapid Communications in Mass Spectrometry\",\"volume\":\"39 2\",\"pages\":\"\"},\"PeriodicalIF\":1.8000,\"publicationDate\":\"2024-11-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Rapid Communications in Mass Spectrometry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/rcm.9936\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"BIOCHEMICAL RESEARCH METHODS\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Rapid Communications in Mass Spectrometry","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/rcm.9936","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMICAL RESEARCH METHODS","Score":null,"Total":0}
A fragmentation study of disaccharide flavonoid C-glycosides using triple quadrupole mass spectrometry and its application for identification of flavonoid C-glycosides in Odontosoria chinensis
Rationale
Flavonoid C-glycosides have a wide range of pharmacological activities. However, there are few mass spectrometric research on C,O-disaccharide flavonoid C-glycosides and di-C,O-saccharide flavonoid C-glycosides. Their low-energy collision-induced dissociation (ESI-CID-MS/MS) fragmentation pattern and differences have not been reported, and the fragment ion library is incomplete. Therefore, it was essential to elucidate the fragmentation patterns of disaccharide flavonoid C-glycosides, which is described in this study.
Methods
Four disaccharide flavonoid C-glycosides such as vitexin-4″-O-glucoside were analyzed by ultra-performance liquid chromatography-triple quadrupole tandem mass spectrometer (UPLC-MS/MS) using electrospray ionization (ESI) in both positive and negative ion modes. Each ion and its proposed fragmentation pathways of the four disaccharide flavonoid C-glycosides were analyzed comprehensively. Finally, ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS/MS) and the established fragmentation patterns have been used to identify disaccharide flavonoid C-glycosides in Odontosoria Chinensis.
Results
The fragmentation pathways of C,O-disaccharide flavonoid C-glycosides and di-C,O-saccharide flavonoid C-glycosides are similar. They both have the mass spectrometric characteristics of O-glycoside and C-glycoside. Product ions after mixed pathways of neutral fragments such as saccharide ring fragment, O-glycosides, H2O, and CH2O elimination appeared in both types of flavonoid C-glycosides, but their relative abundances are significantly different. According to the established fragmentation patterns, di-C,O-saccharide flavonoid glycosides were also found in Odontosoria chinensis.
Conclusion
The fragment ions at m/z 431, 413, 341, 311, 293, and 282 in negative ion mode and m/z 293, 282, 577, 559, 541, 523, 529, and 499 in positive ion mode can serves as the main characteristics for identifying C,O-disaccharide flavonoid C-glycosides and di-C,O-saccharide flavonoid C-glycosides.
期刊介绍：
Rapid Communications in Mass Spectrometry is a journal whose aim is the rapid publication of original research results and ideas on all aspects of the science of gas-phase ions; it covers all the associated scientific disciplines. There is no formal limit on paper length ("rapid" is not synonymous with "brief"), but papers should be of a length that is commensurate with the importance and complexity of the results being reported. Contributions may be theoretical or practical in nature; they may deal with methods, techniques and applications, or with the interpretation of results; they may cover any area in science that depends directly on measurements made upon gaseous ions or that is associated with such measurements.
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