Metabolic Profile of C-Prenyl Coumarins Using Mass Spectrometry-Based Metabolomics
Abstract
:1. Introduction
2. Results
2.1. In Vitro Metabolism of MH, ISM, and MER by HLM and MLM
2.2. Metabolomic Profiling of MH, ISM, and MER Metabolites in Mice
2.3. Structure Elucidation of MH, ISM, and MER Metabolites
2.3.1. Structure Elucidation of MH Metabolites
2.3.2. Structure Elucidation of ISM Metabolites
2.3.3. Structure Elucidation of MER Metabolites
2.4. CYPs Involved in the Formation of MH, ISM, and MER Metabolites
2.5. Anti-Inflammatory Activity of MH, ISM, and MER
2.5.1. Cytotoxicity of MH, ISM, and MER in RAW 264.7 Macrophages
2.5.2. Inhibition of MH, ISM, and MER on LPS-Induced NO Production in RAW 264.7 Cells
2.5.3. Inhibition of MH, ISM, and MER on LPS-Induced over Expression of Pro-Inflammatory Mediators
3. Discussions
4. Materials and Methods
4.1. Chemicals and Reagents
4.2. In Vivo Metabolism of MH, ISM, and MER
4.3. In Vitro Metabolism of Coumarins
4.4. Sample Preparation
4.5. UPLC-ESI-QTOFMS Analysis
4.6. Multivariate Data Analysis
4.7. Anti-Inflammatory Assays
4.7.1. Cell Culture
4.7.2. Cell Viability Assay
4.7.3. NO Inhibition Assay
4.7.4. Real-Time PCR
4.8. Statistical Analysis
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Metabolite | Molecular Formula | RT (min) | m/z [M + H]+ | Mass Error (ppm) | MS/MS Fragments | Identification | Source |
---|---|---|---|---|---|---|---|
Me0 | C15H16O4 | 8.15 | 261.1121 | 0.27 | 243, 231, 217, 189 | Meranzin | P, F, U, H, M |
Me1 * | C14H14O4 | 6.79 | 247.0965 | −1.13 | 229, 221, 201, 187 | Mer-CH2 | U, F, H, M |
Me2 * | C15H14O4 | 6.47 | 259.0965 | 3.94 | 243, 231, 217, 201, 189 | Mer-2H | H, M |
Me2a * | C15H14O4 | 6.85 | 259.0965 | −8.03 | 243, 231, 217, 189 | Mer-2H | H, M |
Me2b * | C15H14O4 | 7.68 | 259.0965 | −6.49 | 243, 229, 217, 203, 189 | Mer-2H | F, U, H, M |
Me3 * | C14H14O5 | 6.67 | 263.0914 | 4.20 | 245, 207, 191, 175 | Mer + O-CH2 | U |
Me4 * | C15H14O5 | 5.43 | 275.0914 | 5.83 | 259, 247, 231, 219, 205 | Mer + CH2 | U |
Me5 * | C15H16O5 | 6.47 | 277.1070 | −3.05 | 259, 247, 219, 205 | Mer + O | F, H, M |
Me5a * | C15H16O5 | 6.83 | 277.1070 | 7.78 | 259, 243, 227, 217, 205 | Mer + O | M |
Me5b * | C15H16O5 | 7.67 | 277.1070 | 4.90 | 259, 233, 217, 205 | Mer + O | F, U, H, M |
Me5c * | C15H16O5 | 7.84 | 277.1070 | −7.02 | 261, 243, 215, 205, 191 | Mer + O | U |
Me6 * | C15H18O5 | 6.29 | 279.1227 | 9.70 | 261, 243, 217, 207, 189 | Mer + H2O | H |
Me6a * | C15H18O5 | 7.70 | 279.1227 | −7.14 | 261, 235, 221, 207, 189 | Mer + H2O | H, M |
Me7 * | C15H14O6 | 6.68 | 291.0863 | 0.65 | 275, 263, 245, 217, 203 | Mer + O + CH2 | U |
Me8 * | C15H18O6 | 5.62 | 295.1176 | 7.42 | 259, 231, 221, 203, 189 | Mer + 2O + 2H | H |
Me9 * | C18H21NO5S | 5.36 | 380.1162 | 1.24 | 334, 305 | Mer + Cysteine | U |
Me9a * | C18H21NO5S | 5.84 | 380.1162 | 3.08 | 364, 334, 291 | Mer + Cysteine | U |
Me10 * | C20H23NO7S | 7.11 | 422.1268 | 0.02 | 404, 380, 376, 362, 334 | Mer + N-acetylcysteine | F, U |
Me10a * | C20H23NO7S | 7.35 | 422.1268 | 7.02 | 404, 380, 358, 376, 334 | Mer + N-acetylcysteine | F |
Me11 * | C21H24O10 | 6.12 | 437.1442 | 4.08 | 359, 261, 243, 189 | Mer + Gluc | U |
Me12 * | C21H24O11 | 4.95 | 453.1391 | 2.36 | 437, 419, 395, 291, 237 | Mer + O + Gluc | U |
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Cheng, Y.; Ma, X.; Zhao, Q.; Wang, C.; Yan, D.; Li, F. Metabolic Profile of C-Prenyl Coumarins Using Mass Spectrometry-Based Metabolomics. Molecules 2021, 26, 6558. https://doi.org/10.3390/molecules26216558
Cheng Y, Ma X, Zhao Q, Wang C, Yan D, Li F. Metabolic Profile of C-Prenyl Coumarins Using Mass Spectrometry-Based Metabolomics. Molecules. 2021; 26(21):6558. https://doi.org/10.3390/molecules26216558
Chicago/Turabian StyleCheng, Yan, Xiaofang Ma, Qi Zhao, Chunyan Wang, Dongmei Yan, and Fei Li. 2021. "Metabolic Profile of C-Prenyl Coumarins Using Mass Spectrometry-Based Metabolomics" Molecules 26, no. 21: 6558. https://doi.org/10.3390/molecules26216558