Approach to the study of C‐glycosyl flavones by ion trap HPLC‐PAD‐ESI/MS/MS: application to seeds of quince (Cydonia oblonga)

Abstract

Ion trap HPLC-PAD-ESI/MS/MS has been used to study C-glycosyl flavones in quince seeds. Comparative analysis of the ions [(M-H)-60]-, [(M-H)-90]- and [(M-H)-120]- from 6-C- and 8-C-glycosyl flavone isomers, together with their respective retention times, allowed deductions to be made about the nature of the sugar units and the positions of C-glycosylation. Vicenin-2 (6,8-di-C-glucosyl apigenin), lucenin-2 (6,8-di-C-glucosyl luteolin), stellarin-2 (6,8-di-C-glucosyl chrysoeriol), isoschaftoside (6-C-arabinosyl-8-C-glucosyl apigenin), schaftoside (6-C-glucosyl-8-C-arabinosyl apigenin), 6-C-pentosyl-8-C-glucosyl chrysoeriol and 6-C-glucosyl-8-C-pentosyl chrysoeriol were identified in quince seed.

Bioactivity and phytochemical characterization of Arenaria montana L.

“…30 The loss of À120 mu is typical of C-attached hexoses, whereas that of À90 mu is observed for C-attached pentoses and it is also usual in the case of 6-C-hexoses but less common in the case of Table 3 Retention time (R t ), wavelengths of maximum absorption in the UV-vis region (l max ), pseudomolecular and MS 2 fragment ions (in brackets, relative abundances), tentative identification and quantification of phenolic compounds in wild Arenaria montana 8-C-hexoses. 31 These observations allowed the tentative identication of peak 2 as apigenin 6-C-hexoside-8-C-pentoside. The fragmentation of peak 4 would be more coherent with an O,C-diglycoside.…”

Selective separation of flavonoid glycosides in Dalbergia odorifera by matrix solid‐phase dispersion using titania

“…The sugar in the C-glycosyl flavonoid always connects to the 6-C or 8-C with the carbon-carbon band, so compound 1 was a 6,8-di-glycosyl flavonoid. Peak 5 0 was tentatively identified as di-C-hexosyl-pentosyl flavonoid, and fragment ion at m/z 365 and 335 might result from simultaneous rupture of two sugars [34]. MS characterization showed that the flavonoid glycoside in D. odorifera are C-glycosyl flavonoids.…”

“…Taking compound 1 0 as an example, the MS spectrum showed the [M1H] 1 at m/z 597, and its MS 2 spectrum is shown in Fig. 5 , respectively, which are produced by cleaving at two sugars simultaneously [33,34]. Many fragment ions produced by combining the loss of H 2 O and the cleavage in the sugar were found in MS 2 spectrum ( Table 2).…”

Bryonia dioica, Tamus communis and Lonicera periclymenum fruits: Characterization in phenolic compounds and incorporation of their extracts in hydrogel formulations for topical application

“…The ion at m/z 353 has been associated to apigenin aglycone bearing some sugar residues (270 + 83 u) that remained attached to it (Ferreres et al, 2003;. Although the identity of the hexoside moieties cannot be established, they might be well associated as being glucose.…”

“…This type of compounds is characterized by the loss of characteristics fragments from the cleavage of the sugar pyrano ring, namely -120 u and 90 u in the case hexosides (Ferreres et al, 2003).…”