title: 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.
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: Chinese Academy of Medical Sciences and Peking Union Medical College, Institute of Medicinal Plant Development, Malianwa North Road 151#, Haidian District, Beijing 100193, China.
authors: Li-Zhen
authors: LZ
authors: Wu
authors: Xiao-Po
authors: XP
authors: Zhang
authors: Xu-Dong
authors: XD
authors: Xu
authors: Qing-Xia
authors: QX
authors: Zheng
authors: Jun-Shan
authors: JS
authors: Yang
authors: Wan-Long
authors: WL
authors: Ding
mesh_terms: D000890:Anti-Infective Agents / Q000032:analysis* / Q000737:chemistry; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000032:analysis / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D055808:Drug Discovery; D004365:Drugs, Chinese Herbal / Q000737:chemistry*; D020834:Ethnopharmacology; D047309:Flavones / Q000032:analysis* / Q000737:chemistry; D005419:Flavonoids / Q000737:chemistry; D006027:Glycosides / Q000032:analysis* / Q000737:chemistry; D015394:Molecular Structure; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000032:analysis / Q000737:chemistry; D029626:Ranunculaceae / Q000737:chemistry*; D013045:Species Specificity; D021241:Spectrometry, Mass, Electrospray Ionization; D053719:Tandem Mass Spectrometry
chemical_list: C581946:2''-O-vanilloylorientin; D000890:Anti-Infective Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D004365:Drugs, Chinese Herbal; D047309:Flavones; D005419:Flavonoids; D006027:Glycosides; D010626:Phenylethyl Alcohol