Characterization of phenolic compounds in Erigeron breviscapus by liquid chromatography coupled to electrospray ionization mass spectrometry

Abstract

Erigeron breviscapus is an important herbal drug for the treatment of cardiovascular and cerebral vessel diseases. In this study, phenolic compounds were extracted from the whole plant of E. breviscapus and analyzed by high-performance liquid chromatography/electrospray ionization mass spectrometry. A total of 53 compounds were identified or tentatively characterized based on their UV and mass spectra. These compounds included caffeoylquinic acids (CQAs), CQA glucosides, malonyl-CQAs, acetyl-CQAs, caffeoyl-2,7-anhydro-3-deoxy-2-octulopyranosonic acids (CDOAs), caffeoyl-2,7-anhydro-2-octulopyranosonic acids (COAs), flavones, flavonols and flavonones. Most of them were reported for the first time from E. breviscapus and nineteen of them belonged to new compounds. The MS(n) spectra of CQA glucosides were similar to CQAs and they were discriminated by their retention times. No caffeic acid related ions (X(0) (-), Y(0) (-) and Z(0) (-)) were observed in MS(n) spectra of acyl-CQAs compared to those of CQAs. Fragment ions ((2,5)O(-), (3,6)O(-) and (4,6)O(-)) corresponding to ring cleavage were shown in MS(n) spectra of CDOAs and COAs, characteristic of this class of compounds. The 5,6,7-trihydroxyl-substituted flavones were dominant in E. breviscapus. Their [A--H](-) ions underwent the loss of a molecule of H(2)O, followed by the loss of CO, which was used to discriminate from other hydroxyl-substituted flavones. Our results are the first comprehensive analysis of E. breviscapus constituents and will be helpful for the quality control of the herb of E. breviscapus and its related preparations.

Development of a functional dairy food: Exploring bioactive and preservation effects of chamomile (Matricaria recutita L.)

“…These compounds presented a similar fragmentation pattern to the ones previously reported by Guimarães et al (2013). MS compounds with similar characteristics were also detected in E. breviscapus samples (Zhang et al, 2007Liao et al, 2010), which were respectively identified as erigoster B (3,9-diCDOA) and 4,9-diCDOA (or 3,4 diCDOA), so that those identities were tentatively assumed for the compounds observed in our case. The…”

“…-m/z at 705) could be associated to 3,4,9-triCDOA (Zhang et al, 2007 or to a diCDOA glucoside, as reported by Liao et al (2010). In our case, an identity as 3,4,9-triCDOA was assumed taking into account that for the diCDOA glucoside an elution earlier to the diCDOAs should be expected due to its greater polarity.…”

Hairy roots of Hypericum perforatum L.: a promising system for xanthone production

“…Five groups of phenolic compounds such as phenolic acids, flavonol glycosides, flavan-3-ols, flavonoid aglycones and xanthones were recorded in HR cultures (Table 1). Their identification was based on the typical UV/Vis spectral data and LC/MS in the negative ionization mode [M-H] -with the subsequent MS 2 , MS 3 and MS 4 analysis for further identification with reference to similar data previously reported [24][25][26][27][28][29][30][31][32][33]. The HPLC analysis of secondary metabolites revealed marked differences between control roots ( Figure 3A) and HR cultures ( Figure 3B).…”

“…HPLC chromatograms confirmed the presence of 5 phenolic acids (F1, F2, F4, F6 and F15) in root extracts (Table 1, Figure 3). Compound F1 with a molecular ion [M-H] -at m/z 191 was identified as quinic acid, taking in account its MS n fragmentation pattern [24]. Quinic acid (F1) was the only detectable phenolic acid in HR cultures.…”

Characterisation of phenolic acid derivatives and flavonoids from different morphological parts of Helichrysum obconicum by a RP-HPLC–DAD-(−)–ESI-MSn method

“…Compounds 20 (t R = 13.9 min), 21 (t R = 14.5 min), 23 (t R = 15.0 min), 26 (t R = 17.0 min) and 30 (t R = 19.6 min) displayed a [MÀH] À ion at m/z 601 and gave characteristic fragment ions of malonyl [MÀHÀ44] À at m/z 557 and [MÀHÀ86] À at m/z 515 (Zhang, Shi, Qu, & Cheng, 2007). However, their MS n fragment ions intensities were different and it was possible to characterise them by comparison with literature data.…”