Metabolic Profiling for Unveiling Mechanisms of Kushenol F against Imiquimod-Induced Psoriasis with UHPLC/MS Analysis
Abstract
:1. Introduction
2. Results and Discussion
2.1. KSCF Mitigated the Psoriatic Dermatitis Induced by IMQ
2.2. Effect of KSCF on Inflammatory Reactions in Psoriasis-like Mice
2.3. Effect of KSCF on Metabolites in the Injured Skin of Psoriasis-like Mice
2.4. Identification of Differential Metabolites
2.5. Metabolic Pathway Analysis
3. Materials and Methods
3.1. Chemicals, Reagents, and Materials
3.2. Animals and Experimental Protocol
3.3. Psoriasis Area and Severity Index (PASI) Assessment
3.4. Image Acquisition and Skin Sample Collection
3.5. Histopathology Analyses
3.6. Measurement of Skin Inflammatory Factors
3.7. Metabolomic Analysis
3.7.1. Sample Pre-Treatment
3.7.2. UHPLC/MS Analysis
3.8. Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Retention Time (min) | Molecular Weight (Da) | VIP | Potential Biomarker | Formula | Change Trend |
---|---|---|---|---|---|
ESI− | |||||
4.843 | 308.124 | 2.604 | Glutaminyltyrosine | C14H19N3O5 | DOWN |
6.468 | 453.202 | 2.054 | 2-Hydroxy-imipramine glucuronide | C25H32N2O7 | UP |
6.183 | 581.300 | 2.676 | Serylarginine | C9H19N5O4 | UP |
2.626 | 263.076 | 1.478 | 3,4,5-trihydroxy-6-[(2-methylpropanoyl)oxy]oxane-2-carboxylic acid | C10H16O8 | DOWN |
2.821 | 374.095 | 2.080 | 7-Hydroxygliclazide | C15H21N3O4S | DOWN |
2.829 | 299.070 | 1.075 | Methionyl-Glutamate | C10H18N2O5S | DOWN |
4.270 | 315.163 | 2.005 | 3-[8-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-2H-chromen-5-yl]propanoic acid | C19H24O4 | DOWN |
4.791 | 165.059 | 1.301 | 3-Mercapto-2-methyl-1-butanol | C5H12OS | DOWN |
6.240 | 480.249 | 2.770 | Dynorphin A (6–8) | C18H37N9O4 | UP |
6.278 | 457.197 | 2.666 | Deoxypyridinoline | C18H28N4O7 | UP |
6.308 | 469.161 | 2.372 | Melleolide B | C24H32O7 | UP |
6.308 | 667.171 | 1.090 | Hydroxychlorpromazine | C17H19ClN2OS | UP |
6.347 | 455.181 | 2.248 | Armillane | C23H32O7 | UP |
6.378 | 437.170 | 2.123 | Nevskin | C24H32O5 | UP |
6.431 | 177.023 | 1.656 | 3,3′-Thiobispropanoic acid | C6H10O4S | UP |
6.442 | 295.031 | 2.518 | Cis,trans-5′-Hydroxythalidomide | C13H10N2O5 | UP |
6.456 | 421.175 | 2.033 | Euglobal IIb | C23H30O5 | UP |
6.462 | 465.202 | 1.909 | Homofukinolide | C25H34O6 | UP |
6.493 | 486.187 | 1.533 | 4-Hydroxyvalsartan | C24H29N5O4 | UP |
5.583 | 451.185 | 1.071 | 7-[(2,6-dihydroxy-2,5,5,8a-tetramethyl-decahydronaphthalen-1-yl)methoxy]-6-hydroxy-2H-chromen-2-one | C24H32O6 | UP |
6.601 | 467.217 | 2.471 | Colupdox a | C25H36O6 | UP |
6.630 | 553.297 | 1.078 | Phytolaccinic acid | C31H48O6 | DOWN |
6.969 | 492.117 | 2.575 | 2-amino-4-({1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-[(2,3-dihydroxy-1-phenylpropyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)butanoic acid | C19H27N3O8S | UP |
7.023 | 609.361 | 1.208 | Lactapiperanol C | C16H26O4 | DOWN |
7.434 | 810.583 | 1.023 | PE(18:0/20:0) | C43H86NO8P | DOWN |
7.480 | 606.500 | 2.048 | 1,1′-(1,4-Dihydro-4-nonyl-3,5-pyridinediyl)bis[1-dodecanone] | C38H69NO2 | DOWN |
8.936 | 453.202 | 1.579 | Colupox a | C25H36O5 | UP |
8.915 | 701.421 | 1.880 | PG(a-13:0/a-15:0) | C34H67O10P | UP |
8.846 | 465.314 | 1.130 | (2β,3α,9α,24R)-Ergosta-7,22-diene-2,3,9-triol | C28H46O3 | DOWN |
7.712 | 865.522 | 1.182 | PG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) | C46H77O10P | DOWN |
7.365 | 820.589 | 1.091 | PE(18:1(11Z)/22:1(13Z)) | C45H86NO8P | DOWN |
7.157 | 463.293 | 2.768 | Palmitoyl glucuronide | C22H42O7 | DOWN |
7.057 | 361.174 | 0.993 | Perindoprilat | C17H28N2O5 | DOWN |
6.541 | 379.218 | 2.167 | 3′-Hydroxystanozolol | C21H32N2O2 | DOWN |
6.475 | 439.185 | 2.144 | Lucidone A | C24H34O5 | UP |
6.456 | 423.154 | 2.463 | 5,7-dihydroxy-4-(1-hydroxypropyl)-6-(3-methylbut-2-en-1-yl)-8-(2-methylbutanoyl)-2H-chromen-2-one | C22H28O6 | UP |
6.451 | 455.217 | 2.656 | Cavipetin D | C25H38O5 | UP |
6.431 | 475.163 | 2.153 | α-CEHC glucuronide | C22H30O10 | UP |
6.378 | 500.167 | 2.330 | 2-amino-4-({1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[4-(2,6-dihydroxyphenyl)-3-hydroxy-2-methylbutan-2-yl]sulfanyl}ethyl}-C-hydroxycarbonimidoyl)butanoic acid | C21H31N3O9S | UP |
6.371 | 453.165 | 2.610 | Diosbulbin H | C23H30O7 | UP |
6.354 | 439.186 | 1.945 | 1α-O-Methylquassin | C23H32O6 | UP |
6.347 | 507.174 | 2.465 | L-Nicotianine | C10H12N2O4 | UP |
6.284 | 520.193 | 2.082 | Hydroxynefazodone | C25H32ClN5O3 | UP |
6.240 | 452.218 | 1.926 | Chondroitin sulfate E (GalNAc4,6diS-GlcA), precursor 5a | C7H9N3O | UP |
6.222 | 369.211 | 1.248 | 3-keto-Digoxigenin | C23H32O5 | DOWN |
6.218 | 476.279 | 1.123 | LysoPE(0:0/18:2(9Z,12Z)) | C23H44NO7P | DOWN |
6.134 | 457.160 | 1.105 | Valechlorin | C22H31ClO8 | UP |
5.718 | 371.226 | 2.685 | Digoxigenin | C23H34O5 | DOWN |
5.114 | 348.156 | 1.934 | (+)-O-Methylarmepavine | C20H25NO3 | DOWN |
5.065 | 329.179 | 2.313 | 12,20-Dioxo-leukotriene B4 | C20H28O5 | DOWN |
4.974 | 357.211 | 1.896 | 17-Hydroxy-E4-neuroprostane | C22H32O5 | DOWN |
4.589 | 357.222 | 1.037 | Kinetensin 1-3 | C15H30N6O4 | UP |
2.829 | 365.143 | 1.110 | Valproic acid glucuronide | C14H24O8 | DOWN |
2.814 | 296.106 | 1.004 | 7-Aminonitrazepam | C15H13N3O | DOWN |
1.685 | 295.040 | 1.398 | N-Acetyldjenkolic acid | C9H16N2O5S2 | UP |
1.527 | 183.044 | 1.218 | Mevalonic acid | C6H12O4 | UP |
6.371 | 383.161 | 1.501 | 21-Hydroxy-5b-pregnane-3,11,20-trione | C21H30O4 | DOWN |
6.278 | 581.263 | 1.973 | S-(3-Methylbutanoyl)-dihydrolipoamide-E | C13H25NO2S2 | UP |
8.922 | 689.351 | 1.131 | Zeranol | C18H26O5 | UP |
ESI+ | |||||
6.444 | 453.200 | 3.257 | Pro Ser Ser Tyr | C20H28N4O8 | UP |
4.727 | 828.534 | 0.976 | 3-O-Sulfogalactosylceramide (d18:1/18:1(9Z)) | C42H79NO11S | DOWN |
3.285 | 404.222 | 1.210 | Ser Ala Ala Arg | C15H29N7O6 | UP |
4.253 | 317.177 | 1.919 | Capillartemisin A | C19H24O4 | DOWN |
5.069 | 331.193 | 2.827 | 16-Hydroxy-4-oxoretinoic acid | C20H26O4 | DOWN |
6.224 | 371.225 | 1.960 | 17-phenyl trinor-13,14-dihydro Prostaglandin A2 | C23H30O4 | DOWN |
6.254 | 395.252 | 1.328 | (3R, 6′Z)-3,4-Dihydro-8-hydroxy-3-(6-pentadecenyl)-1H-2-benzopyran-1-one | C24H36O3 | UP |
6.304 | 565.350 | 1.002 | PG(22:2(13Z,16Z)/0:0) | C28H53O9P | UP |
6.324 | 313.077 | 2.457 | Inosine-5′-carboxylate | C11H12N4O7 | UP |
7.031 | 626.533 | 1.139 | Muricatenol | C37H68O6 | UP |
6.338 | 301.077 | 2.967 | Temazepam | C16H13ClN2O2 | UP |
1.543 | 286.157 | 2.191 | Tryptophyl-Valine | C16H21N3O3 | UP |
3.194 | 298.150 | 1.266 | Histidinyl-Threonine | C10H16N4O4 | DOWN |
3.319 | 281.119 | 1.191 | 6-hydroxy-7E,9E-Octadecadiene-11,13,15,17-tetraynoic acid | C18H16O3 | UP |
4.064 | 534.323 | 1.347 | Cys Lys Lys Arg | C21H43N9O5S | DOWN |
4.235 | 255.129 | 1.186 | Isoleucyl-Threonine | C10H20N2O4 | DOWN |
4.305 | 622.377 | 1.446 | Tyr Arg Lys Arg | C27H47N11O6 | DOWN |
4.474 | 277.124 | 1.256 | Isobutyrylcarnitine | C11H22NO4+ | UP |
4.604 | 386.246 | 1.473 | Pseudoginsenoside RT3 | C41H70O13 | DOWN |
4.654 | 549.172 | 1.514 | Myricatomentoside I | C26H32O10 | DOWN |
4.987 | 359.225 | 1.475 | 7,8-epoxy-17S-HDHA | C22H30O4 | DOWN |
5.118 | 696.452 | 1.502 | PA(16:1(9Z)/15:0) | C34H65O8P | DOWN |
5.170 | 828.533 | 1.338 | PE(MonoMe(11,3)/MonoMe(11,3)) | C43H74NO10P | DOWN |
5.994 | 242.134 | 0.972 | Lysyl-Methionine | C11H23N3O3S | UP |
6.016 | 548.287 | 1.511 | 11-Hydroxyprogesterone 11-glucuronide | C27H38O9 | UP |
6.082 | 465.259 | 1.132 | (−)-Jolkinol B | C29H36O5 | UP |
6.136 | 502.163 | 2.001 | 3-(3-hydroxyphenyl)-2-(4-hydroxyphenyl)-5-[(E)-2-(3hydroxyphenyl)ethenyl]-2,3-dihydro-1 benzofuran-6-ol | C28H22O5 | UP |
6.149 | 467.275 | 1.316 | 1,25-Dihydroxyvitamin D3-26,23-lactone | C27H40O5 | UP |
6.205 | 363.225 | 1.097 | 5α-Pregnan-20α-ol-3-one | C21H34O2 | UP |
6.224 | 453.221 | 1.813 | Australigenin | C27H42O4 | UP |
6.283 | 534.221 | 1.608 | Cyclocalopin D | C23H32O13 | UP |
6.297 | 365.241 | 1.267 | Adipostatin A | C21H36O2 | UP |
6.324 | 574.253 | 1.565 | Glaucarubolone 15-O-β-d-glucopyranoside | C26H36O13 | UP |
6.360 | 427.276 | 1.508 | Asymmetric dimethylarginine | C8H18N4O2 | UP |
6.360 | 455.179 | 3.227 | Gly Glu Ser Tyr | C19H26N4O9 | UP |
6.367 | 441.200 | 4.192 | Gly Thr Tyr Thr | C19H28N4O8 | UP |
6.416 | 435.294 | 2.760 | Alanyl-Lysine | C9H19N3O3 | UP |
6.437 | 527.345 | 2.800 | Pro Val Arg Arg | C22H42N10O5 | UP |
6.451 | 355.125 | 2.024 | Meta-O-Dealkylated flecainide | C15H19F3N2O3 | UP |
6.472 | 463.182 | 2.851 | PA(8:0/8:0) | C19H37O8P | UP |
6.479 | 441.200 | 3.151 | (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate | C18H37O7P | UP |
6.500 | 714.509 | 1.058 | PA(18:1(9Z)/18:3(9Z,12Z,15Z)) | C39H69O8P | UP |
6.521 | 523.411 | 2.648 | Panaxydol linoleate | C35H54O3 | DOWN |
6.604 | 411.225 | 1.903 | Pro Pro Thr Pro | C19H30N4O6 | UP |
6.646 | 722.519 | 1.386 | PE(18:4(6Z,9Z,12Z,15Z)/P-18:1(11Z)) | C41H72NO7P | UP |
6.660 | 678.492 | 1.312 | PE(18:4(6Z,9Z,12Z,15Z)/P-16:0) | C39H70NO7P | UP |
6.674 | 634.465 | 1.471 | Tsugarioside B | C37H60O7 | UP |
6.856 | 670.523 | 1.605 | PE(15:0/18:0) | C38H76NO8P | UP |
7.010 | 904.712 | 1.184 | PC(o-20:0/22:0) | C50H102NO7P | UP |
7.066 | 407.153 | 1.119 | 3b,16a-Dihydroxyandrostenone sulfate | C19H28O6S | UP |
8.944 | 425.205 | 4.129 | O-Desmethylcarvedilol | C23H24N2O4 | UP |
9.287 | 423.189 | 2.131 | Cys Val Thr Thr | C16H30N4O7S | UP |
8.685 | 895.754 | 1.939 | TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/18:3(9Z,12Z,15Z)) | C61H102O6 | DOWN |
6.940 | 539.360 | 1.721 | 3-methyl-4-(methylamino)-1,2-diphenylbutan-2-ol | C18H23NO | UP |
6.870 | 626.496 | 1.675 | PE(15:0/P-16:0) | C36H72NO7P | UP |
6.870 | 614.353 | 1.399 | LysoPC(22:2(13Z,16Z)) | C30H58NO7P | UP |
6.849 | 714.550 | 1.546 | PC(14:1(9Z)/18:0) | C40H78NO8P | UP |
6.828 | 802.604 | 1.578 | PC(18:0/22:4(7Z,10Z,13Z,16Z)) | C48H88NO8P | UP |
6.737 | 696.496 | 1.312 | CL(i-12:0/18:2(9Z,11Z)/i-18:0/i-19:0) | C76H144O17P2 | UP |
6.730 | 740.523 | 1.185 | CL(18:0/18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) | C83H148O17P2 | UP |
6.646 | 840.578 | 1.939 | PG(18:0/22:4(7Z,10Z,13Z,16Z)) | C46H83O10P | DOWN |
6.604 | 163.076 | 1.060 | 4-Hydroxy-2,6,6-trimethyl-3-oxo-1,4-cyclohexadiene-1-carboxaldehyde | C10H12O3 | UP |
6.590 | 295.066 | 1.816 | 2-hydroxy-3-[3-(3-methylbut-2-en-1-yl)-4-(sulfooxy)phenyl]propanoic acid | C14H18O7S | UP |
6.583 | 459.187 | 2.136 | Ser Glu Ser His | C17H26N6O9 | UP |
6.542 | 355.194 | 1.101 | Nigakihemiacetal B | C22H30O6 | DOWN |
6.493 | 764.516 | 1.715 | CL(16:0/18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)) | C83H152O17P2 | DOWN |
6.472 | 700.493 | 1.413 | PA(15:0/18:2(9Z,12Z)) | C36H67O8P | UP |
6.472 | 385.136 | 3.206 | 2′,7-Dihydroxy-4′-methoxy-8-prenylflavan | C21H24O4 | UP |
6.465 | 351.130 | 1.754 | N-Ribosylhistidine | C11H17N3O6 | UP |
6.451 | 521.396 | 1.727 | Ginsenoyne A linoleate | C35H52O3 | DOWN |
6.388 | 285.081 | 1.654 | (2S)-2-hydrazinyl-3-(4-hydroxy-3-methoxyphenyl)-2-methylpropanoic acid | C11H16N2O4 | DOWN |
6.381 | 439.184 | 3.069 | Gln Glu Tyr | C19H26N4O8 | UP |
6.345 | 375.115 | 1.271 | Cyclic N-Acetylserotonin glucuronide | C18H20N2O8 | DOWN |
6.338 | 361.135 | 2.023 | 7-Hydroxy-6-methyl-8-ribityl lumazine | C12H16N4O7 | UP |
6.324 | 538.255 | 1.523 | Rubraflavone B | C30H34O5 | UP |
6.311 | 618.283 | 2.136 | 3′-Deaminofusarochromanone | C15H19NO4 | UP |
6.297 | 424.221 | 2.812 | Sphingosine 1-phosphate | C18H38NO5P | UP |
6.290 | 508.280 | 2.746 | LysoPE(0:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) | C27H44NO7P | UP |
6.283 | 510.296 | 4.312 | LysoPE(0:0/22:5(7Z,10Z,13Z,16Z,19Z)) | C27H46NO7P | UP |
6.276 | 583.277 | 3.375 | (4E)-6-hydroxy-1,7-diphenylhept-4-en-3-one | C19H20O2 | UP |
6.241 | 451.279 | 0.944 | PA(19:1(9Z)/0:0) | C22H43O7P | UP |
6.231 | 498.259 | 3.159 | PE(18:3/0:0) | C23H42NO7P | UP |
6.199 | 437.264 | 1.065 | 1-Oleoyl Lysophosphatidic Acid (sodium salt) | C21H41O7P | UP |
6.186 | 175.123 | 2.811 | α-Methyltryptamine (AMT) | C11H14N2 | UP |
6.174 | 569.298 | 3.370 | 11-α-O-β-d-Glucopyranosyl-16α-O-methylneoquassin | C29H44O11 | UP |
6.075 | 487.359 | 1.085 | Lys Ile Val Lys | C23H46N6O5 | UP |
6.005 | 618.340 | 1.903 | Pentasine | C30H49N6O10+ | UP |
6.000 | 349.209 | 1.127 | Oryzalexin E | C20H32O2 | UP |
5.554 | 183.082 | 1.526 | 2-Methyl-4-propyl-1,3-oxathiane | C8H16OS | UP |
5.112 | 740.479 | 1.500 | PS(14:0/20:3(8Z,11Z,14Z)) | C40H72NO10P | DOWN |
5.006 | 240.142 | 0.993 | Isopropyl β-d-glucoside | C9H18O6 | UP |
4.945 | 336.130 | 0.976 | Gynocardin | C12H17NO8 | DOWN |
4.897 | 352.161 | 1.890 | (+/−)-Rollipyrrole | C16H20N2O3 | DOWN |
4.615 | 338.145 | 1.145 | N-Acetyl-3-hydroxyprocainamide | C15H23N3O3 | DOWN |
4.391 | 233.097 | 1.094 | L-Targinine | C7H16N4O2 | UP |
3.611 | 402.242 | 1.022 | N-Didesmethylmifepristone (RU 42848) | C27H31NO2 | DOWN |
3.396 | 261.150 | 1.327 | Methyl dihydrophaseate | C16H24O5 | UP |
3.222 | 229.123 | 1.660 | Blennin B | C15H20O4 | UP |
2.566 | 267.140 | 1.527 | (S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid | C18H20O3 | UP |
1.360 | 217.134 | 1.518 | Girgensonine | C13H16N2O | DOWN |
0.013 | 300.208 | 1.040 | 2-hydroxydesipramine | C18H22N2O | UP |
6.800 | 524.283 | 1.270 | 11-β-Hydroxyandrosterone-3-glucuronide | C25H38O9 | UP |
No. | Pathway | p-Value | Details |
---|---|---|---|
1 | Sphingolipid metabolism | 0.001 | KEGG |
2 | Linoleic acid metabolism | 0.036 | KEGG |
3 | Steroid hormone biosynthesis | 0.021 | KEGG |
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Yang, X.; Cheng, J.; Yin, X.; Ao, T.; He, X.; Yang, Y.; Lin, Y.; Chen, Z. Metabolic Profiling for Unveiling Mechanisms of Kushenol F against Imiquimod-Induced Psoriasis with UHPLC/MS Analysis. Molecules 2024, 29, 2410. https://doi.org/10.3390/molecules29112410
Yang X, Cheng J, Yin X, Ao T, He X, Yang Y, Lin Y, Chen Z. Metabolic Profiling for Unveiling Mechanisms of Kushenol F against Imiquimod-Induced Psoriasis with UHPLC/MS Analysis. Molecules. 2024; 29(11):2410. https://doi.org/10.3390/molecules29112410
Chicago/Turabian StyleYang, Xingxin, Jiaoli Cheng, Xunqing Yin, Ting Ao, Xudong He, Yaqin Yang, Yuping Lin, and Zhen Chen. 2024. "Metabolic Profiling for Unveiling Mechanisms of Kushenol F against Imiquimod-Induced Psoriasis with UHPLC/MS Analysis" Molecules 29, no. 11: 2410. https://doi.org/10.3390/molecules29112410