Identification of Xanthine Oxidase Inhibitors from Celery Seeds Using Affinity Ultrafiltration–Liquid Chromatography–Mass Spectrometry
Abstract
:1. Introduction
2. Results
2.1. Chemical Profiles of Celery Seed Extracts
2.2. Identification of XOD-Binding Compounds from Celery Seed Extracts
2.3. Validation of Inhibitory Activities
2.4. The Study of Molecular Recognition
3. Discussion
3.1. Identification of Chemical Constituents in Celery Seed Extracts
3.2. Identification of XOD-Binding Compounds from Celery Seed Extracts
3.3. Validation of Inhibitory Activities
3.4. The Study of Molecular Recognition
3.5. UF–LC–MS Assay for Screening Novel XOD Inhibitors
4. Materials and Methods
4.1. Materials and Reagents
4.2. Instruments
4.3. Chromatographic Analysis
4.4. Mass Spectrometry Conditions
4.5. Preparation of Celery Seed Extract
4.6. XOD Activity Assay
4.7. Screening for XOD Inhibitors Using UF–LC–MS
4.8. Molecular Docking
4.9. Statistical Analysis
5. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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NO | Rt (min) | Identification | MS+ (m/z) | ppm | Element Composition | MS2 Fragment Ion (m/z) | References |
---|---|---|---|---|---|---|---|
1 | 1.89 | Adenosine | 268.1042 | 0.6 | C10H13N5O4 | 136.0620; 119.0350 | * |
2 | 2.50 | Fructose-phenylalanine | 328.1390 | −0.2 | C15H21NO7 | 310.1326; 292.1213; 254.1228; 246.1097; 166.0861; 132.0792 | [18] |
3 | 2.99 | Pantothenic acid | 220.1176 | −1.6 | C9H17NO5 | 220.1164; 202.1063; 184.0972; 128.0257; 90.0550 | * |
4 | 4.38 | Tryptophan | 205.0972 | −0.8 | C11H12N2O2 | 188.0696; 146.0593; 118.0645; 115.0539 | [19] * |
5 | 8.35 | Chlorogenic acid | 355.1020 | −1.0 | C16H18O9 | NA | [20] * |
6 | 10.62 | p-Hydroxybenzaldehyde | 123.0441 | 0.4 | C7H6O2 | 123.0465; 95.0482; 77.0383 | [21] * |
7 | 11.54 | Coumaroylquinic acid | 339.1075 | 0.2 | C16H18O8 | 147.0436; 119.0481; 91.0532 | [20] |
8 | 13.54 | Coumaroylquinic acid or isomer | 339.1076 | 0.5 | C16H18O8 | 147.0440; 119.0489; 91.0541 | [20] |
9 | 17.11 | Luteolin 7-O-apiosylglucoside | 581.1502 | 0.2 | C26H28O15 | 287.0554 | [20] |
10 | 17.38 | Luteolin 7-O-glucoside | 449.1075 | −0.8 | C21H20O11 | 287.0543 | [20] * |
11 | 18.91 | Senkyunolide J | 227.1274 | −1.7 | C12H18O4 | 209.1164; 191.1134; 153.0542 | [19,22] |
12 | 19.20 | Apiin | 565.1553 | 0.2 | C26H28O14 | 271.0609 | [20] * |
13 | 19.65 | Chrysoeriol 7-O-apiosylglucoside | 595.1652 | −0.9 | C27H30O15 | 463.1226; 301.0701; 286.0463; 258.0526 | [20] |
14 | 19.85 | Luteolin 7-O-malonyl-apiosylglucoside | 667.1488 | −2.5 | C29H30O18 | 535.1115; 287.0558; | [20] |
15 | 20.22 | Luteolin 7-O-6′-malonyl glucoside | 535.1082 | −0.1 | C24H22O14 | 535.1062; 449.1039; 287.0529 | [20] |
16 | 20.32 | Chrysoeriol 7-O-glucoside | 463.1234 | −0.2 | C22H22O11 | 301.0694; 286.0507 | [20] |
17 | 20.85 | Malonylapiin A | 651.1539 | −2.6 | C29H30O17 | NA | [20] |
18 | 21.15 | Malonylapiin B | 651.1547 | −1.3 | C29H30O17 | 519.1109; 271.0594 | [20] |
19 | 21.91 | 6″-Malonylapiin | 651.1549 | −1.0 | C29H30O17 | 519.1121; 271.0556 | [20] |
20 | 22.22 | Chrysoeriol 7-O-6″-malonyl apiosylglucoside | 681.1661 | −0.1 | C30H32O18 | 549.1281; 301.0717; 286.0474 | [20] |
21 | 25.19 | Luteolin | 287.0552 | 0.6 | C15H10O6 | NA | [23] * |
22 | 26.91 | Sedanolide | 195.1380 | 0.2 | C12H18O2 | 177.1276; 149.1323; 125.0617; 111.0436; 97.0645; 79.0542 | [23,24] * |
23 | 27.22 | Isomer of procyanidin B1 | 579.1487 | −1.7 | C30H26O12 | 427.0852; 409.0739; 291.0699; 247.0802; 205.0693 | [25] |
24 | 27.50 | Apigenin | 271.0605 | 1.5 | C15H10O5 | 271.0584; 163.0352; 153.0182; 119.0480 | [26] * |
25 | 27.75 | Chrysoeriol | 301.0707 | −0.9 | C16H12O6 | 301.0710; 286.0476; 258.0500; 229.0465 | [20,26] |
26 | 27.82 | Dihydroxy-3-butylphthalide | 223.0969 | 1.9 | C12H14O4 | 177.0905; 167.0327; 149.0218; 121.0271 | [27] |
27 | 28.22 | Lunularic acid | 257.0841 | 8.4 | C15H14O4 | 213.0919; 171.0809; 107.0497; 106.0415 | * |
28 | 28.53 | 3-Butylphthalide | 191.1067 | 0.2 | C12H14O2 | 129.0684; 117.0703; 91.0526; 77.0383 | [21,28] |
29 | 28.92 | Senkyunolide F | 207.1016 | 0.1 | C12H14O3 | 189.0882; 161.0959; 151.0386; 146.0726; 105.0328; 77.0381 | [11,19] |
30 | 29.56 | Cinnamaldehyde | 133.0648 | 0.1 | C9H8O | 133.0644; 105.0700; 79.0536; 77.0739 | * |
31 | 30.19 | Sedenenolide | 193.1222 | −0.6 | C12H16O2 | 175.1126; 147.1175; 137.0603; 105.0696; 91.0540; 77.0383 | [29] |
32 | 31.91 | Linolenic acid | 279.2317 | −0.6 | C18H30O2 | 131.0828; 95.0853; 67.0531 | * |
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Gan, X.; Peng, B.; Chen, L.; Jiang, Y.; Li, T.; Li, B.; Liu, X. Identification of Xanthine Oxidase Inhibitors from Celery Seeds Using Affinity Ultrafiltration–Liquid Chromatography–Mass Spectrometry. Molecules 2023, 28, 6048. https://doi.org/10.3390/molecules28166048
Gan X, Peng B, Chen L, Jiang Y, Li T, Li B, Liu X. Identification of Xanthine Oxidase Inhibitors from Celery Seeds Using Affinity Ultrafiltration–Liquid Chromatography–Mass Spectrometry. Molecules. 2023; 28(16):6048. https://doi.org/10.3390/molecules28166048
Chicago/Turabian StyleGan, Xiaona, Bo Peng, Liang Chen, Yanjun Jiang, Tingzhao Li, Bo Li, and Xiaodong Liu. 2023. "Identification of Xanthine Oxidase Inhibitors from Celery Seeds Using Affinity Ultrafiltration–Liquid Chromatography–Mass Spectrometry" Molecules 28, no. 16: 6048. https://doi.org/10.3390/molecules28166048