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Characterization of aromatic glycosides in the extracts of Trollius species by ultra high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry.
J Pharm Biomed Anal. 2013 Mar 05; 75:55-63.JP

Abstract

Ultra high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC/ESI-Q-TOF MS/MS) was used to investigate the MS fragmentation behaviors of flavone C-glycosides present in the extracts of five Trollius species. In this study, the primary MS fragmentation pathways and key diagnostic fragment ions of flavone C-glycosides were systematically investigated and summarized to distinguish different types of derivatives and to trace other analogs in Trollius species. This method was useful, rapid, efficient and sensitive and allowed the simultaneous identification of different types of flavone C-glycosides present in other medicinal plants. The features of the MS fragmentation of these compounds indicated that the product ions were primarily the result of cleavage in the saccharide moiety, followed by hydrogen rearrangement and dehydration. In this study, thirty-six components including thirty-two flavone C-glycosides, two flavone O-glycosides and two phenylethanoid glycosides, were identified in the extracts of five Trollius species. Eleven of the flavone C-glycosides were identified by comparison with reference standards, and twenty-one flavone C-glycosides were tentatively identified based on their retention times, exact mass information and fragment ions. Two potentially new flavone C-glycosides (2″-O-vanilloylorientin and 2″-O-feruloylvitexin) were successfully characterized based on the summarized fragmentation pathways, and six known flavone C-glycosides (2″-O-glucosylvitexin, 2″-O-acetylorientin, 2″-O-acetylvitexin, 3″-O-acetylorientin, 3″-O-acetylvitexin and 6″-O-acetylvitexin) were identified in these plant species for the first time. In conclusion, the fragmentation pathways proposed in this paper were helpful for the identification of different types of flavone C-glycosides when no reference standards were available.

Authors+Show Affiliations

Chinese Academy of Medical Sciences and Peking Union Medical College, Institute of Medicinal Plant Development, Malianwa North Road 151#, Haidian District, Beijing 100193, China.No affiliation info availableNo 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

23312385

Citation

Wu, Li-Zhen, et al. "Characterization of Aromatic Glycosides in the Extracts of Trollius Species By Ultra High-performance Liquid Chromatography Coupled With Electrospray Ionization Quadrupole Time-of-flight Tandem Mass Spectrometry." Journal of Pharmaceutical and Biomedical Analysis, vol. 75, 2013, pp. 55-63.
Wu LZ, Zhang XP, Xu XD, et al. Characterization of aromatic glycosides in the extracts of Trollius species by ultra high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. J Pharm Biomed Anal. 2013;75:55-63.
Wu, L. Z., Zhang, X. P., Xu, X. D., Zheng, Q. X., Yang, J. S., & Ding, W. L. (2013). Characterization of aromatic glycosides in the extracts of Trollius species by ultra high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis, 75, 55-63. https://doi.org/10.1016/j.jpba.2012.11.015
Wu LZ, et al. Characterization of Aromatic Glycosides in the Extracts of Trollius Species By Ultra High-performance Liquid Chromatography Coupled With Electrospray Ionization Quadrupole Time-of-flight Tandem Mass Spectrometry. J Pharm Biomed Anal. 2013 Mar 5;75:55-63. PubMed PMID: 23312385.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Characterization of aromatic glycosides in the extracts of Trollius species by ultra high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. AU - Wu,Li-Zhen, AU - Zhang,Xiao-Po, AU - Xu,Xu-Dong, AU - Zheng,Qing-Xia, AU - Yang,Jun-Shan, AU - Ding,Wan-Long, Y1 - 2012/11/16/ PY - 2012/08/16/received PY - 2012/11/07/revised PY - 2012/11/09/accepted PY - 2013/1/15/entrez PY - 2013/1/15/pubmed PY - 2013/7/5/medline SP - 55 EP - 63 JF - Journal of pharmaceutical and biomedical analysis JO - J Pharm Biomed Anal VL - 75 N2 - Ultra high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC/ESI-Q-TOF MS/MS) was used to investigate the MS fragmentation behaviors of flavone C-glycosides present in the extracts of five Trollius species. In this study, the primary MS fragmentation pathways and key diagnostic fragment ions of flavone C-glycosides were systematically investigated and summarized to distinguish different types of derivatives and to trace other analogs in Trollius species. This method was useful, rapid, efficient and sensitive and allowed the simultaneous identification of different types of flavone C-glycosides present in other medicinal plants. The features of the MS fragmentation of these compounds indicated that the product ions were primarily the result of cleavage in the saccharide moiety, followed by hydrogen rearrangement and dehydration. In this study, thirty-six components including thirty-two flavone C-glycosides, two flavone O-glycosides and two phenylethanoid glycosides, were identified in the extracts of five Trollius species. Eleven of the flavone C-glycosides were identified by comparison with reference standards, and twenty-one flavone C-glycosides were tentatively identified based on their retention times, exact mass information and fragment ions. Two potentially new flavone C-glycosides (2″-O-vanilloylorientin and 2″-O-feruloylvitexin) were successfully characterized based on the summarized fragmentation pathways, and six known flavone C-glycosides (2″-O-glucosylvitexin, 2″-O-acetylorientin, 2″-O-acetylvitexin, 3″-O-acetylorientin, 3″-O-acetylvitexin and 6″-O-acetylvitexin) were identified in these plant species for the first time. In conclusion, the fragmentation pathways proposed in this paper were helpful for the identification of different types of flavone C-glycosides when no reference standards were available. SN - 1873-264X UR - https://www.unboundmedicine.com/medline/citation/23312385/Characterization_of_aromatic_glycosides_in_the_extracts_of_Trollius_species_by_ultra_high_performance_liquid_chromatography_coupled_with_electrospray_ionization_quadrupole_time_of_flight_tandem_mass_spectrometry_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0731-7085(12)00627-9 DB - PRIME DP - Unbound Medicine ER -