Phytochemistry and Comprehensive Chemical Profiling Study of Flavonoids and Phenolic Acids in the Aerial Parts of Allium Mongolicum Regel and Their Intestinal Motility Evaluation

Abstract

To clarify whether flavonoids and phenols in Allium mongolicum Regel have the effect of improving gastrointestinal function and analyze its quality, this study was designed to isolate and identify them from the aerial parts of A. mongolicum by using various chromatographic and spectrophotometric methods, a bioassay on motility of mouse isolated intestine tissue, as well as qualitative analysis using liquid chromatography/mass spectrometry (LC-MS) analysis. As a result, 31 flavonoids and phenolic acids were obtained and identified, including six new flavonoid glycosides, mongoflavonosides A1 (1), A2 (2), A3 (3), A4 (4), B1 (5), B2 (6), and four new phenolic acid glycosides, mongophenosides A1 (7), A2 (8), A3 (9), B (10). Among them, eleven flavonoids and three phenolic acids showed significant increase in the height of mouse small intestinal muscle. It was a first systematic bioactive constituents’ study for A. mongolicum on gastrointestinal tract. Furthermore, according to the retention time (tR) and the exact mass-to-charge ratio (m/z), thirty-one compounds were unambiguously identified by comparing to the standard references by using LC-MS. Then, on the basis of generalized rules of MS/MS fragmentation pattern, chromatographic behaviors, as well as biosynthetic laws of the 31 isolates, five flavonoid glycosides and one phenolic acid glycoside were tentatively speculated. On the basis of the study, a fast analysis method for flavonoids and phenolic acids in A. mongolicum was established.

Antifungal effects and active compounds of the leaf of Allium mongolicum Regel

“…Data for compound 11 : white powder, m. p. 142–144°C; ESI-MS: Calcd for C 15 H 18 O 9 ([M-H] - ), 341.17; 1 H NMR (400 MHz, DMSO- d 6 ) δ : 7.55 (d, J = 15.8 Hz, 1H, H-7), 7.08 (d, J = 2.1 Hz, 1H, H-2), 7.01 (dd, J = 8.2, 2.0 Hz, 1H, H-6), 6.78 (d, J = 8.2 Hz, 1H, H-5), 6.26 (d, J = 15.9 Hz, 1H,H-8), 5.45 (d, J = 7.9 Hz, 1H), 5.28 (s, 1H), 5.06 (s, 2H,H-6′), 4.58 (s, 1H), 3.69–3.62 (m, 2H), 3.31–3.10 (m, 6H); 13 C NMR (100 MHz, DMSO- d 6 ) δ : 165.39 (C-9), 148.81 (C-4), 146.47 (C-7), 145.70 (C-3), 125.42 (C-1), 121.74 (C-6), 115.86 (C-5), 114.91 (C-8), 113.41 (C-2), 94.31 (C-1′), 77.86 (C-5′), 76.52 (C-3′), 72.56 (C-2′), 69.60 (C-4′), and 60.67 (C-6′). According to the abovementioned data and literature ( Dong et al, 2020 ), compound 11 was identified as 1-Caffeoyl glucoside and its molecular formula is shown in Figure 7 . MS diagrams and 1 H-NMR and 13 C-NMR spectra were shown in Supplementary Figures S31–S33 , respectively.…”

“…Data for compound 7 : pale yellow powder, m. p. 187–189°C; ESI-MS: Calcd for C 33 H 38 O 23 ([M + H] + ), 803.05; 1 H NMR (400 MHz, DMSO- d 6 ) δ : 12.56 (s, 1H, H-5), 8.93 (s, 1H, H-3′), 7.68 (d, J = 2.2 Hz, 1H, H-2′), 7.64 (dd, J = 8.6, 2.3 Hz, 1H, H-6′), 7.23 (d, J = 8.7 Hz, 1H, H-5′), 6.85 (d, J = 2.1 Hz, 1H, H-8), 6.46 (d, J = 2.1 Hz, 1H, H-6) , 5.56–5.44 (m, 4H), 5.30 (t, J = 2.4 Hz, 1H), 5.23 (d, J = 7.3 Hz, 2H), 5.09 (s, 3H), 4.97 (s, 1H), 4.87 (d, J = 7.1 Hz, 1H, H-1‴), 4.63 (t, J = 5.7 Hz, 1H), 4.31 (t, J = 5.8 Hz, 1H), 3.92 (d, J = 7.9 Hz, 1H), 3.77–3.70 (m, 2H), 3.59 (dd, J = 11.3, 5.0 Hz, 2H), 3.49 (d, J = 6.1 Hz, 2H), 3.26–3.15 (m, 7H), 3.10 (d, J = 4.1 Hz, 3H); 13 C NMR (100 MHz, DMSO- d 6 ) δ : 177.75 (C-4), 172.00 (C-6‴'), 162.68 (C-7), 160.85 (C-5), 156.07 (C-2), 156.07 (C-9), 147.67 (C-4′), 146.19 (C-3′), 134.16 (C-3), 124.33 (C-1′), 121.06 (C-6′), 116.64 (C-2′), 115.45 (C-5′), 105.81 (C-10), 101.48 (C-1‴), 100.65 (C-1″), 99.35 (C-1‴'), 99.20 (C-6), 94.33 (C-8),77.69 (C-5″), 77.26 (C-5‴), 76.50 (C-3″), 75.94 (C-3‴'), 75.83 (C-3‴), 74.85 (C-5‴'), 74.12 (C-2″), 73.26 (C-2‴), 72.80 (C-2‴'), 71.49 (C-4‴'), 70.00 (C-4″), 69.78 (C-4‴), 60.97 (C-6″), and 60.72 (C-6‴). According to the abovementioned data and literature ( Fossen et al, 2006 ; Dong et al, 2020 ), compound 7 was identified as Quercetin-3,7- O -diglucoside-4′- O -glucuronide and its molecular formula is shown in Figure 4 . MS diagrams and 1 H-NMR and 13 C-NMR spectra were shown in Supplementary Figures S19–S21 , respectively.…”

“…Data for compound 10 : pale yellow crystal solid, m. p. 140–145°C; ESI-MS: Calcd forC 21 H 28 O 14 ([M-H] - ), 503.20; 1 H NMR (400 MHz, DMSO- d 6 ) δ : 7.55 (d, J = 15.9 Hz, 1H, H-7), 7.40 (d, J = 15.9 Hz, 1H, H-7), 7.06 (d, J = 2.1 Hz, 1H, H-2), 7.07–7.00 (m, 1H, H-2), 7.04–6.98 (m, 1H, H-6), 6.95 (dd, J = 8.2, 2.1 Hz, 1H, H-6), 6.76 (dd, J = 8.2, 6.0 Hz, 2H, H-5), 6.27 (d, J = 15.9 Hz, 1H, H-8), 6.16 (d, J = 15.9 Hz, 1H, H-8), 5.60–5.52 (m, 1H, H-3′), 5.15 (d, J = 3.4 Hz, 1H), 5.16–4.35 (m, 16H), 3.70–3.32 (m, 15H), 3.25–2.85 (m, 13H), 2.06 (s, 1H); 13 C NMR (100 MHz, DMSO- d 6 ) δ : 167.83 (C-9), 164.95 (C-9), 148.58 (C-4), 148.11 (C-4), 146.17 (C-7), 145.54 (C-3), 144.54 (C-3), 125.68 (C-1), 125.56 (C-1), 121.58 (C-6), 121.09 (C-6), 115.73 (C-5), 115.09 (C-5), 114.88 (C-2), 114.61 (C-2), 113.53 (C-8), 105.09 (C-1″), 104.56 (C-1″), 92.46 (C-1′), 91.44 (C-1′), 82.22 (C-2′), 81.66 (C-2′), 77.63 (C-5″), 76.83 (C-3″), 76.72 (C-3″), 76.38 (C-5′), 76.18 (C-5′), 75.75 (C-4′), 74.56 (C-3′), 73.87 (C-3′), 71.83 (C-2″), 71.68 (C-2″), 70.18 (C-2′), 70.08 (C-2′), 69.46 (C-4″), 69.17 (C-4″), 61.20 (C-6′), 61.11 (C-6″), 60.46 (C-6′), and 60.41 (C-6″). According to the abovementioned data and literature ( Duan, et al, 2012 ; Dong et al, 2020 ), compound 10 was identified as 1-Caffeoyl gentiobioside (two kinds of sugar configurations: α and β ) and its molecular formula is shown in Figure 6 . MS diagrams and 1 H-NMR and 13 C-NMR spectra were shown in Supplementary Figures S27–S30 , respectively.…”

“…In the course of studying the effect of A. mongolicum on mutton quality, it found that volatile oil, polysaccharide, and flavonoids showed an inhibitory effect on animal-related foodborne pathogens ( Sa et al, 2014 ; Muqier et al, 2017 ). As an important material for finding antimicrobial compounds, some monomeric compounds of flavonoid and ethyl cinnamate, dibutyl oxalate, and 2-hexenal from the essential oil of A. mongolicum were gained in recent years ( Wang et al, 2012 ; Dong et al, 2015 ; Dong et al, 2020 ). However, the antimicrobial activity compounds of A. mongolicum have not been systematically explored at present.…”

Food and Drug Analysis

“…Dong et al [7] designed to isolate and identify the flavonoids and phenols from the aerial parts of Allium mongolicum Regel by using various chromatographic and spectrophotometric methods, a bioassay on motility of mouse isolated intestine tissue, as well as qualitative analysis using liquid chromatography/mass spectrometry (LC-MS). The aim of this study is to clarify whether these isolates have the effect of improving gastrointestinal function.…”