Detection of flavone C-glycosides in the extracts from the bark ofPrunus aviumL. andPrunus cerasusL.

Abstract

The extracts from the bark of Prunus avium and Prunus cerasus have been analyzed by using high pressure liquid chromatography/electrospray ionization mass spectrometry. For the first time in the bark of Prunus species flavonoid C-glycosides have been detected. On the basis of the characteristic fragmentation patterns of their [M-H]− and [M + H]+ ions, three flavonoid C-glycosides have been identified, namely apigenin-6,8-di-C-glucoside (vicenin-2), apigenin-6-C-glucoside (isovitexin) and chrysin-8-C-glucoside. Taking into account the widely studied biological activities of flavonoid C-glycosides, the barks of these common fruit trees seem to be interesting materials of potential medical or cosmetic application.

Antioxidant capacity and fragmentation features of C‐glycoside isoflavones by high‐resolution electrospray ionization tandem mass spectrometry using collision‐induced and high‐energy collisional dissociation techniques

“…The ESI-CID-MS/MS, in negative mode of ionization (25 eV), shows an important tool to annotation of flavone and isoflavones structural isomers.These data can indicate that, in the negative mode of ionization, C-glycosil isoflavones require most intense energy to fragment in comparison with C-glycosil flavones, with analogous substitution pattern. In addition to the examples cited, in measurements using ESI-CID at 25 eV, flavones such as vitexin, isovitexin,10,27 and chrysin 8-C-glycoside28 showed similar behavior compared to our work; that is, they presented [M À H] À ≤ 10%, whereas isoflavones in the present study showed [M À H] À $ 60% at the same conditions.…”

Sustainable valorization of cherry (Prunus avium L.) pomace waste via the combined use of (NA)DESs and bio-ILs

“…Saccharide chains were composed of one to three sugar units, represented by hexosyl (−162 u) or deoxyhexosyl (−146 u) moieties linked to the aglycones through an O -glycoside bond, except compound 10 that was identified as apigenin C -glucoside ([M − H] − at m / z 431.0989) by the observation in the ESI fragmentation pathway of the diagnostic product ions ([M − H − 90] − at m / z 341.07 and [M − H − 120] − at m / z 311.06) characteristic of flavonoid C -glycosides. 62 Flavone C -glycosides have not been previously reported in cherry fruits, but they have been recently found in the bark, 63 thus the occurrence of compound 10 could be attributed to woody plant parts in the cherry waste. All aglycones were also detected in the last region of the chromatograms.…”

“…Finally, peak 2 ([M − H] − at m/z 353.0881) was assigned as chlorogenic acid (3-Ocaffeoylquinic acid), as deduced by the presence in the MS/MS spectra of a product ion at m/z 191.06 due to the loss of a caffeoyl moiety. 61 62 Flavone C-glycosides have not been previously reported in cherry fruits, but they have been recently found in the bark, 63 thus the occurrence of compound 10 could be attributed to woody plant parts in the cherry waste. All aglycones were also detected in the last region of the chromatograms.…”

Microwave-Assisted Extraction of Condensed Tannins from Branches of Prunus spinosa L.: Response Surface Modeling and Optimization

“…In fact, the branches of genus Prunus may be a great source of tannins with important biological properties. The bark of P. cerasus and P. avium contain flavone Cglycosides (vicenin-2, isovitexin and chrysin-8-C-glucoside) [19]. P. domestica bark has in its composition flavan-3-ols (catechin and epicatechin), a phenolic glucoside (annphenone and six dimeric A-type proanthocyanidins with antimicrobial activity [20].…”