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Approach to the study of flavone di-C-glycosides by high performance liquid chromatography-tandem ion trap mass spectrometry and its application to characterization of flavonoid composition in Viola yedoensis.
J Mass Spectrom. 2014 Oct; 49(10):1010-24.JM

Abstract

The mass spectrometric (MS) analysis of flavone di-C-glycosides has been a difficult task due to pure standards being unavailable commercially and to that the reported relative intensities of some diagnostic ions varied with MS instruments. In this study, five flavone di-C-glycoside standards from Viola yedoensis have been systematically studied by high performance liquid chromatography-electrospray ionization-tandem ion trap mass spectrometry (HPLC-ESI-IT-MS(n)) in the negative ion mode to analyze their fragmentation patterns. A new MS(2) and MS(3) hierarchical fragmentation for the identification of the sugar nature (hexoses or pentoses) at C-6 and C-8 is presented based on previously established rules of fragmentation. Here, for the first time, we report that the MS(2) and MS(3) structure-diagnostic fragments about the glycosylation types and positions are highly dependent on the configuration of the sugars at C-6 and C-8. The base peak ((0,2) X1 (0,2) X(2)(-) ion) in MS(3) spectra of di-C-glycosides could be used as a diagnostic ion for flavone aglycones. These newly proposed fragmentation behaviors have been successfully applied to the characterization of flavone di-C-glycosides found in V. yedoensis. A total of 35 flavonoid glycosides, including 1 flavone mono-C-hexoside, 2 flavone 6,8-di-C-hexosides, 11 flavone 6,8-di-C-pentosides, 13 flavone 6,8-C-hexosyl-C-pentosides, 5 acetylated flavone C-glycosides and 3 flavonol O-glycosides, were identified or tentatively identified on the base of their UV profiles, MS and MS(n) (n = 5) data, or by comparing with reference substances. Among these, the acetylated flavone C-glycosides were reported from V. yedoensis for the first time.

Authors+Show Affiliations

Department of Pharmacognosy, School of Pharmacy, Fudan University, Shanghai, 201203, China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25303391

Citation

Cao, Jie, et al. "Approach to the Study of Flavone di-C-glycosides By High Performance Liquid Chromatography-tandem Ion Trap Mass Spectrometry and Its Application to Characterization of Flavonoid Composition in Viola Yedoensis." Journal of Mass Spectrometry : JMS, vol. 49, no. 10, 2014, pp. 1010-24.
Cao J, Yin C, Qin Y, et al. Approach to the study of flavone di-C-glycosides by high performance liquid chromatography-tandem ion trap mass spectrometry and its application to characterization of flavonoid composition in Viola yedoensis. J Mass Spectrom. 2014;49(10):1010-24.
Cao, J., Yin, C., Qin, Y., Cheng, Z., & Chen, D. (2014). Approach to the study of flavone di-C-glycosides by high performance liquid chromatography-tandem ion trap mass spectrometry and its application to characterization of flavonoid composition in Viola yedoensis. Journal of Mass Spectrometry : JMS, 49(10), 1010-24. https://doi.org/10.1002/jms.3413
Cao J, et al. Approach to the Study of Flavone di-C-glycosides By High Performance Liquid Chromatography-tandem Ion Trap Mass Spectrometry and Its Application to Characterization of Flavonoid Composition in Viola Yedoensis. J Mass Spectrom. 2014;49(10):1010-24. PubMed PMID: 25303391.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Approach to the study of flavone di-C-glycosides by high performance liquid chromatography-tandem ion trap mass spectrometry and its application to characterization of flavonoid composition in Viola yedoensis. AU - Cao,Jie, AU - Yin,Chengle, AU - Qin,Yan, AU - Cheng,Zhihong, AU - Chen,Daofeng, PY - 2014/03/20/received PY - 2014/06/05/revised PY - 2014/06/12/accepted PY - 2014/10/11/entrez PY - 2014/10/11/pubmed PY - 2015/6/11/medline KW - LC-MSn KW - Viola yedoensis KW - flavone di-C-glycoside KW - fragmentation KW - ion trap SP - 1010 EP - 24 JF - Journal of mass spectrometry : JMS JO - J Mass Spectrom VL - 49 IS - 10 N2 - The mass spectrometric (MS) analysis of flavone di-C-glycosides has been a difficult task due to pure standards being unavailable commercially and to that the reported relative intensities of some diagnostic ions varied with MS instruments. In this study, five flavone di-C-glycoside standards from Viola yedoensis have been systematically studied by high performance liquid chromatography-electrospray ionization-tandem ion trap mass spectrometry (HPLC-ESI-IT-MS(n)) in the negative ion mode to analyze their fragmentation patterns. A new MS(2) and MS(3) hierarchical fragmentation for the identification of the sugar nature (hexoses or pentoses) at C-6 and C-8 is presented based on previously established rules of fragmentation. Here, for the first time, we report that the MS(2) and MS(3) structure-diagnostic fragments about the glycosylation types and positions are highly dependent on the configuration of the sugars at C-6 and C-8. The base peak ((0,2) X1 (0,2) X(2)(-) ion) in MS(3) spectra of di-C-glycosides could be used as a diagnostic ion for flavone aglycones. These newly proposed fragmentation behaviors have been successfully applied to the characterization of flavone di-C-glycosides found in V. yedoensis. A total of 35 flavonoid glycosides, including 1 flavone mono-C-hexoside, 2 flavone 6,8-di-C-hexosides, 11 flavone 6,8-di-C-pentosides, 13 flavone 6,8-C-hexosyl-C-pentosides, 5 acetylated flavone C-glycosides and 3 flavonol O-glycosides, were identified or tentatively identified on the base of their UV profiles, MS and MS(n) (n = 5) data, or by comparing with reference substances. Among these, the acetylated flavone C-glycosides were reported from V. yedoensis for the first time. SN - 1096-9888 UR - https://www.unboundmedicine.com/medline/citation/25303391/Approach_to_the_study_of_flavone_di_C_glycosides_by_high_performance_liquid_chromatography_tandem_ion_trap_mass_spectrometry_and_its_application_to_characterization_of_flavonoid_composition_in_Viola_yedoensis_ L2 - https://doi.org/10.1002/jms.3413 DB - PRIME DP - Unbound Medicine ER -