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

IF 1.8 3区化学 Q4 BIOCHEMICAL RESEARCH METHODS Rapid Communications in Mass Spectrometry Pub Date : 2024-11-09 DOI:10.1002/rcm.9936

Bin Huang, Fangjun Chen, Xiang Zhang, Yanzhen Hu, Yuanyuan Zhang, Le Chen, Yan Meng, Ping Wen

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Abstract

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.

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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。

理由黄酮 C-糖苷具有广泛的药理活性。然而，有关 C,O-二糖黄酮 C-苷和二 C,O-二糖黄酮 C-苷的质谱研究却很少。它们的低能碰撞诱导解离（ESI-CID-MS/MS）碎片模式和差异尚未见报道，碎片离子库也不完整。因此，阐明双糖黄酮 C-糖苷的碎片模式至关重要，本研究对此进行了描述：方法：采用超高效液相色谱-三重四极杆串联质谱仪（UPLC-MS/MS），以正、负离子模式电喷雾离子化（ESI）分析了牡荆素-4″-O-葡萄糖苷等四种双糖黄酮 C-糖苷。对四种双糖黄酮 C-糖苷的每个离子及其碎片路径进行了全面分析。最后，利用超高效液相色谱-四极杆飞行时间质谱法（UPLC-Q-TOF-MS/MS）和已建立的碎片模式鉴定了麦冬中的双糖黄酮 C-糖苷：结果：C,O-二糖黄酮C-糖苷和二糖黄酮C-糖苷的破碎途径相似。它们都具有 O-糖苷和 C-糖苷的质谱特征。两类黄酮 C-糖苷中都出现了糖环片段、O-糖苷、H2O 和 CH2O 等中性片段混合消除后的产物离子，但其相对丰度有显著差异。根据已建立的碎片模式，在小龙蔘中还发现了二-C,O-糖黄酮苷：结论：在负离子模式下，m/z 431、413、341、311、293和282的碎片离子；在正离子模式下，m/z 293、282、577、559、541、523、529和499的碎片离子是鉴定C,O-二糖黄酮C-糖苷和二-C,O-糖黄酮C-糖苷的主要特征。

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来源期刊

Rapid Communications in Mass Spectrometry 化学-分析化学

CiteScore

4.10

自引率

5.00%

发文量

219

审稿时长

2.6 months

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.