UPLC-ESI-MS/MS Profiling of Secondary Metabolites from Methanol Extracts of In Vivo and In Vitro Tissues of Daucus capillifolius Gilli (A Comparative Study)
Abstract
:1. Introduction
2. Results and Discussion
2.1. Identification of Phenolic Compounds of Methanol Extracts of In Vivo and In Vitro Tissues of D. capillifoliusby UPLC–ESI-MS/MS
2.1.1. Identification of Phenolic Acids and Acid Derivatives in Methanol Extracts of In Vivo and In Vitro Tissues of D. capillifolius Gilli
No. | Rt (min) | Name | Parent Ion (m/z) | MS2 Fragments (m/z) | I | II | III | IV | Reference |
---|---|---|---|---|---|---|---|---|---|
1 | 0.87 | Malic acid | 133 | − | − | 4.92 | − | [20] | |
2 | 1.92 | Benzoic acid derivative | 279 | 121.0 (100%) | − | + | − | − | [21] |
3 | 1.96 | Syringic acid pentoside | 329 | 131.1 (100%) | + | − | + | + | [22] |
4 | 2.88 | Coumaric acid | 327/165 | 163.7 (100%) | + | − | − | − | [23,24] |
5 | 2.95 | Hydroxy benzoic acid isomer-1 | 137 | 121.0, 92.9 (100%) | − | + | − | − | [25,26] |
6 | 3.59 | gallic acid derivative | 293 | 171.0 (100%) | − | + | − | − | [21] |
7 | 4.91 | Hydroxy benzoic acid isomer-2 | 137 | 94 [M+H−44], 77 [M+H−44-OH] | − | 2.41 | 4.01 | 6.13 | [25,26] |
8 | 5.21 | Caffeic acid | 179 | 135.2 (100%) [M-H-COOH] | + | − | − | + | [24,25] |
9 | 5.41 | Gallic acid derivative | 259 | 169.0 | − | + | − | − | [21] |
10 | 5.82 | Vanillic acid derivative | 279 | 167.4 (100%) | + | − | − | − | [22] |
11 | 6.15 | Chlorogenic acid isomer-1 | 353/355 | 191.3 (100%),137.3 | + | − | − | + | [25,26] |
12 | 6.43 | Cinnamic acid derivative | 329 | 146.6 (100%) [M−182]− | + | − | − | − | [22] |
13 | 6.80 | Caffeic acid derivative | 371 | 178.9 (100%) | + | − | − | − | [24] |
14 | 7.59 | Quinic acid derivative | 271 | 191.0 100%) | − | + | − | − | [22] |
15 | 7.69 | Ferulic acid derivative | 273 | 192.7 (100%), 148.7 99 | + | − | − | − | [24] |
16 | 7.88 | Hydroxyl gallic acid | 185 | 1.99 | − | − | − | [27] | |
17 | 8.50 | Chlorogenic acid isomer 2 | 355 | − | 9.29 | − | − | [25,26] | |
18 | 8.22 | Caffeic acid derivative (malonyl rhamnoside) | 367 | 135.0 (100%) [M-H−232]− | + | − | − | + | [24] |
19 | 9.56 | Ellagic acid | 303 | 257.0, 229, 201.2, 164.9, 153.1, (100%)137.0, 123.0, 108.4 | + | − | − | − | [28] |
20 | 9.81 | Quinic acid | 193 | 119.0, 105.1, 91.0, 79 | + | − | − | − | [28,29] |
21 | 9.97 | Sinapic acid isomer 1 | 225 | 6.35 | − | − | − | [30] | |
22 | 10.13 | Sinapicacid isomer-2 | 225 | 2.21 | − | − | − | [30] | |
23 | 10.93 | Methyl gallate isomer 1 | 185 | 171, 125 | − | − | 1.81 | − | [20] |
24 | 10.91 | Methyl gallate isomer 2 | 185 | 171, 125 | − | − | − | 0.67 | [20] |
25 | 12.86 | Coumaric acid derivative | 279 | 162.6, 121.6 (100%) | − | + | − | − | [21] |
26 | 13.95 | Coumaric acid | 163 | − | − | 2.95 | − | [21] | |
27 | 15.29 | Hydroxy ferulic acid | 209 | 11.4 | − | − | − | [31] | |
28 | 15.92 | Benzoic acid derivative | 307 | 120.8 (100%) | + | − | − | + | [21] |
29 | 16.21 | Chlorogenic acid isomer-3 | 353 | − | − | 9.69 | − | [25,26] | |
30 | 16.55 | Benzoic acid methyl ester | 137 | 4.14 | − | − | − | [21] | |
31 | 21.44 | Quinic acid derivative | 371 | 191.0 (100%) | − | + | − | − | [21] |
32 | 22.31 | Coumaric acid glucuronide | 339 | 163.0 | − | 0.18 | − | − | [21] |
No. | Rt (min) | Name | Parent Ion (m/z) | MS2 Fragments (m/z) | I | II | III | IV | Reference |
---|---|---|---|---|---|---|---|---|---|
Flavonoid aglycones | |||||||||
33 | 13.56 | Diosmetin | 299/301 | -ve/284.9 (100%) [M-CH3], 255.6 [M−15-CO]; or +ve/286.1, 258.0 (100%), 168.4, 146.9, 135, 130.0 | + | − | − | − | [32] |
34 | 11.77 | Dimethoxyflavone | 281 | 149.3 (100%) [ring A], 132.0 [ring B] 149(A)/132(B) | + | − | − | − | [33] |
35 | 12.07 | Luteolin | 285 | 175.1, 132.8 (100%) | + | + | − | + | [34,35] |
36 | 13.21 | Apigenin | 269 | 148.9, 119.2, 117.2 (100%) | + | − | − | − | [34] |
37 | 16.20 | Galangin | 269/271 | 119.9 (100%), 152.9 (100%), 118.9 | + | + | − | − | [25,36] |
38 | 16.20 | 5,4′-dihydroxy-3,7-dimethoxyflavone | 313 | 283.0 [M-H−30], 254.8 (100%) [M-H−30−28] | + | + | − | − | [33] |
39 | 16.42 | Methyl apigenin (Acacetin) | 283 | 268.0 (100%) [M-H-CH3] | + | + | − | − | [33,37] |
40 | 16.51 | 5-hydroxy-3′,4′,7-trimethoxy-flavanone | 329 | 314, 299 | − | 2.51 | − | 3.11 | [37] |
41 | 17.32 | Isorhamnetin | 317 | 1.25 | − | − | − | [20] | |
42 | 22.92 | Dihydroxyflavone(chrysin) | 255 | 135.0, 119.0(100%) | − | + | − | − | [33] |
Flavonoid-O-glycosides | |||||||||
43 | 1.76 | Diosmetin-7-O-glucuronopyranosyl-O-rhamnoside | 621 | 445.0 (100%) [M-H−176] | + | + | − | − | [38] |
44 | 6.75 | Myricetin-3-O-glucoside | 479 | 317.0, 183.7, 161.1, 159.0 | + | + | − | − | [39] |
45 | 6.80 | Myricetin-3-O- acetyl glucoside | 491 | 317.1 (100%) | − | + | + | [40] | |
46 | 8.15 | Quercetin-3-O-acetyl glucoside pentoside | 639 | 303.0 (100%) | + | − | − | − | [41] |
47 | 8.50 | Quercetin diglucoside | 625 | 301 | 1.08 | − | − | − | [20] |
48 | 8.75 | Quercetin glucoside | 463 | 301 | 1.83 | − | − | − | [20] |
49 | 9.14 | Luteolin-7-O-rutinoside | 593 | 285.2, 284.2 (100%) | + | − | − | − | [26,42] |
50 | 9.25 | Quercetin-O-rhamnoside | 447 | 301 | 0.89 | − | − | − | [20] |
51 | 9.43 | Apigenin-7-O-caffoeylhexoside | 593 | 269.4 (100%) | + | − | − | − | [43] |
52 | 9.43 | Diosmetin-O-coumaroyhexoside | 607 | 299.0 (100%), 163, 131.1 | + | − | − | + | [44] |
53 | 9.58 | Quercetin-3-O-galactoside | 463 | 300.6 (100%), 178.9 | 3.03 | − | − | − | [24] |
54 | 10.04 | Apigenin-7-O-glucoside | 431/433 | 268.0, 269.0 (100%), 108.0 | + | + | − | + | [45] |
55 | 10.14 | Luteolin-7-O-glucoside | 447 | 285.0 (100%) | + | + | − | − | [26,42] |
56 | 10.32 | Luteolin-7-O-glucuronoside | 461 | 284.5, 283.3 (100%) | + | + | − | + | [26,32] |
57 | 10.26 | Apigenin-7-O-glucoside | 431 | 270 | 0.77 | − | − | − | [45] |
58 | 10.40 | Quercetin-O- rhamnoside | 447 | 299.0 | 2.02 | − | − | [20] | |
59 | 12.85 | Diosmetin-O-rutinoside | 609 | 2.22 | − | − | − | [46] | |
60 | 13.27 | Diosmetin-7-O-hexoside | 461 | 299.3 (100%), 284.5 | + | − | − | + | [47] |
61 | 13.38 | Luteolin derivative | 567 | 285 (100%) | + | − | − | − | [34,35] |
62 | 15.36 | Luteolin acetyl glucoside | 489 | 285 | − | 1.12 | − | − | [34,35] |
63 | 19.44 | Diosmetin-7-O-rutinoside | 609 | 300.9, 206.3 (100%), 157.4 | − | − | − | − | [46] |
64 | 21.91 | Myricetin-3-O-rhamnoside | 463 | 316.6 (100%) | + | + | + | + | [20] |
Flavonoid-C-glycosides | |||||||||
65 | 13.27 | Diosmetin-8-C-rhamnoside | 445 | 341 [M−104]− | + | − | − | + | [35,46] |
66 | 23.27 | Apigenin-8-C-hexoside | 433 | 313.1 [M+H−120] 150.6, 130.7 (100%) | − | + | + | + | [48] |
67 | 23.39 | Diosmetin-8-C-glucoside | 461 | 341.0 (M-H−120) (100%) | + | + | − | + | [46] |
68 | 24.49 | Diosmetin-8-C-glucoside-O-rhamnoside | 609 | 489.2 [M+H−120], 462.5 [M+H−146], 341.9 [aglycone+H+41] | − | + | + | − | [48] |
No. | Rt (min) | Name | Parent Ion (m/z) | MS2 Fragments (m/z) | I | II | III | IV | Reference |
---|---|---|---|---|---|---|---|---|---|
Anthocyanins | |||||||||
69 | 6.36 | Pelargonidin-3-O-glucuronosyl-O-glucoside | 610 | 271.3 | + | − | − | − | [49,50] |
70 | 10.51 | Cyanidin-3-O-glucoside | 449 | 287.0 | 0.80 | + | + | + | [51,52] |
71 | 10.60 | Cyanidin-3-O-glucoside | 449 | 287.0 | 5.78 | − | − | − | [51,52] |
72 | 12.90 | Cyanidin derivative | 620 | 287(100%) | + | − | + | + | [49] |
73 | 13.21 | Cyanidin-O-glucuronosyl-O-glucoside Or feruloyl-O-glucoside | 625 | 287.0 (100%) | + | − | − | + | [49,52] |
74 | 16.95 | Cyanidin derivative | 721 | 287.4 (100%) | + | + | + | + | [49,52,53] |
75 | 28.31 | Malvidin-3-O-glucoside-malonyl-glucoside | 741 | 331.4 [M−410] | + | + | − | + | [54] |
Tannins | |||||||||
76 | 7.17 | Gallocatechin | 305 | 261, 119, 97.0 (100%) | 2.55 | − | − | − | [55] |
77 | 7.59 | Epigallocatechin | 305/307 | 261, 119, 97.0 (100%) | 5.31 | − | − | − | [55] |
78 | 7.68 | Epigallocotechin derivatives | 721 | 304.7 (100%) | + | − | − | − | [55] |
79 | 11.25 | Catechin-3-O-hexoside-pentoside | 585 | 294 [M−291] | − | − | + | − | [55] |
80 | 14.54 | Catechin-O-acetyl glucoside pentoside | 625 | 288.5 (100%) | + | − | − | − | [50] |
81 | 16.07 | Catechin | 291 | 174.9, 147.3, 137.3, 121, 106.9 | − | − | − | − | [50] |
Acetylenic compounds | |||||||||
82 | 20.85 | 9-[Heptadeca-1-en-4,6,9-triyne-3,8-diol] | 281 | 57.3, 56.7, 43.2, 54.9, 66.7, 79.0, 81.1, 95.0, 109.2, 83.1, 122.8, 71.0(100%) | + | + | + | − | [12,56,57] |
83 | 23.45 | 11-[8-hydroxytetradeca-1-en-4,6,9-triyn-3-yl acetate] | 281 | 97.0, 56.9, 80.9, 69.2, 95.4 106.6, 107.2 146.8 55.0 (100%) | + | + | + | − | [12,56,57] |
84 | 28.27 | Falcaridiol-8-O-methyl ether | 297 | 167.3, 149.4, 134.9, 121.1, 106.8, 105, 97.0, 83.1 ,81.0, 69.1, 55.0 (100%), 42.8 | + | + | + | − | [12,56,57] |
Nitrogenous compounds | |||||||||
85 | 1.35 | 3-Methyl-Indole | 132 | 76.0 | − | +11 | 18.55 | 17.6 | [58] |
86 | 1.77 | 4-(aminoethyl) benzoic acid | /166 or 120 | 119.9, 103.0 (100%), 93.0, 91.0, 76.9 | − | +12 | 22.67 | + | [59] |
87 | 2.23 | 4-(aminoethyl) benzoic acid isomer | 164/166 | 119.9, 103.0 (100%), 93.0, 91.0, 76.9 | − | +20.9 | 1.82 | 21.57 | [59] |
2.1.2. Identification of Flavonoids
Flavonoids Aglycones
Identification of Flavonoid Glycosides
- Identification of O-glycosides
2.1.3. Identification of Anthocyanins
2.1.4. Identification of Tannins
2.1.5. Identification of Acetylenic Compounds
2.1.6. Identification of Nitrogenous Compounds
3. Materials and Methods
3.1. Plant Materials
3.1.1. Induction of Calli from In Vitro Germinated Seedlings
3.1.2. Extract Preparation
3.2. UPLC-ESI-MS/MS Analysis and Separation Method of D. capillifolius Extracts
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Abdallah, R.H.; Hassan, W.H.B.; Al-Massarani, S.M.; Abdel-Mageed, W.M.; Eldahmy, S.I.; Basudan, O.A.; Parveen, M.; El Senosy, E.; Abdelaziz, S. UPLC-ESI-MS/MS Profiling of Secondary Metabolites from Methanol Extracts of In Vivo and In Vitro Tissues of Daucus capillifolius Gilli (A Comparative Study). Molecules 2024, 29, 2694. https://doi.org/10.3390/molecules29112694
Abdallah RH, Hassan WHB, Al-Massarani SM, Abdel-Mageed WM, Eldahmy SI, Basudan OA, Parveen M, El Senosy E, Abdelaziz S. UPLC-ESI-MS/MS Profiling of Secondary Metabolites from Methanol Extracts of In Vivo and In Vitro Tissues of Daucus capillifolius Gilli (A Comparative Study). Molecules. 2024; 29(11):2694. https://doi.org/10.3390/molecules29112694
Chicago/Turabian StyleAbdallah, Rehab H., Wafaa H. B. Hassan, Shaza M. Al-Massarani, Wael M. Abdel-Mageed, Samih I. Eldahmy, Omer A. Basudan, Mehtab Parveen, Entesar El Senosy, and Sahar Abdelaziz. 2024. "UPLC-ESI-MS/MS Profiling of Secondary Metabolites from Methanol Extracts of In Vivo and In Vitro Tissues of Daucus capillifolius Gilli (A Comparative Study)" Molecules 29, no. 11: 2694. https://doi.org/10.3390/molecules29112694