Characterization of C‐glycosyl quinochalcones in Carthamus tinctorius L. by ultraperformance liquid chromatography coupled with quadrupole‐time‐of‐flight mass spectrometry

Abstract

C-Glycosyl quinochalcones are unique components in Carthamus tinctorius L. The reported C-glycosyl quinochalcones have the same quinochalcone skeleton with a hydroxyl group at the 5'-position and a glucose linked to this position with a carbon-carbon bond. In this study, the standard hydroxysafflor yellow A and water-extracted fraction of Carthamus tinctorius L. were analyzed by ultraperformance liquid chromatography coupled with quadrupole-time-of-flight mass spectrometry (UPLC/Q-TOFMS) in both positive and negative ion modes. The fragmentation pathways of C-glycosyl quinochalcones were interpreted and validated by accurate mass measurement. Their fragmentation showed a special cleavage at the C-C bond except for the typical internal cleavage at the sugar moiety of other C-glycosyl flavonoids. In positive ion mode, cleavage of the 5'-glucose produced an [M+H-162](+) ion by a neutral loss, while cleavage of the 5'-glucose in negative ion mode led to an [M-H-163](-.) ion by radical cleavage. The cleavage from the carbonyl group produced fragment ions containing an A or a B ring. The fragment ions containing an A ring were common product ions of seven compounds in both ion modes, and fragment ions containing the B ring were used to judge the different substituent groups at the 3'-position. The fragmentation patterns of seven structurally related C-glycosyl quinochalcones were analyzed systematically and the formation of the fragment ions in two modes is explained in detail in this report. UPLC/Q-TOFMS is an effective tool for characterizing a complex sample, which gives higher resolution separation and generates accurate mass measurement of the product ions.

Markers for Identification of Faded Safflower (Carthamus tinctoriusL.) Colorants by HPLC-PDA-MS - Ancient Fibres, Pigments, Paints and Cosmetics Derived from Antique Recipes

“…Besides carthamin (Figure 1), kaempferol and apigenin, other products are present with yellow quinochalcone uv-vis spectral characteristics (Y in Figure 4) [15,25], and four other components with very particular uvvis and mass spectra, but not contributing to color (ct in Figure 4). Since the main emphasis of this paper was on markers for safflower red, yellow components were not investigated further.…”

Making of Natural Dyeing Scarves by Tie-Dyeing Technique

“…Carthamin is the major red pigment in safflower and it has antioxidant activity [7]. The basic structure of those pigments is a C-glucosyl quinochalcone [8]. Figure 1 showed the chemical structure of carthamin contained in safflower.…”

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

“…The UV and MS data of eight compounds are summarized in Table 2. According to their fragmentation in MS 2 , they can be identified as C-glycosyl flavonoids since successive losses of H 2 O were observed obviously and cleavages at the bonds in the sugar were main fragmentation [31,32]. 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.…”