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Characterisation of Homoflavonoids from Three Ophioglossum Species Using Liquid Chromatography with Diode Array Detection and Electrospray Ionisation Tandem Mass Spectrometry
Author(s) -
Wan ChuanXing,
Luo JianGuang,
Gu YuCheng,
Xu DeRan,
Kong LingYi
Publication year - 2013
Publication title -
phytochemical analysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.574
H-Index - 72
eISSN - 1099-1565
pISSN - 0958-0344
DOI - 10.1002/pca.2430
Subject(s) - chemistry , fragmentation (computing) , tandem mass spectrometry , electrospray , chromatography , electrospray ionization , mass spectrometry , high performance liquid chromatography , aglycone , tandem , analytical chemistry (journal) , stereochemistry , glycoside , materials science , computer science , composite material , operating system
Homoflavonoids, characterised by one more carbon atom directly added to C 6 –C 3 –C 6 backbone of flavonoids, are rich in the species of genus Ophioglossum . Up to now we have little knowledge about their MS fragmentation patterns. It is therefore necessary to investigate their MS fragmentation pathways so as to distinguish them from other types of flavonoids. Objective To develop a rapid method for identifying homoflavonoids from Ophioglossum based on their characteristic MS fragmentation. Methods Mass spectrometry fragmentation pathways and qualitative analysis of homoflavonoids in three ferns of Ophioglosssum were investigated by using high‐performance liquid chromatography coupled with diode‐array detection and electrospray ionisation tandem mass spectrometry (HPLC–DAD–ESI/MS n ). Results The analyses of the MS n spectra of the homoflavonoids allowed us to classify them into two types according to their fragmentation characteristics. The type I homoflavonoids, with an attached additional carbon atom to the C‐3 position of the C‐ring, presented the initial competing loss of H 2 O and CH 2 O from their aglycone ions, compared to the initial removal of H 2 O or CO in the case of the type II homoflavonoids, which bear the additional carbon atom at the C‐2’ site of the B‐ring and forming ring D. The above characteristic fragmentations of homoflavonoids were quite different from those of other flavonoids, and were successfully applied to identify homoflavonoids in the crude extracts of three Ophioglossum species. Conclusion The HPLC–DAD–ESI/MS n method obtained in the present study provided a powerful tool for identifying homoflavonoids from ferns in the genus Ophioglossum . Copyright © 2013 John Wiley & Sons, Ltd.