Molecular Characterization of Thymus capitellatus Extracts and Their Antioxidant, Neuroprotective and Anti-Proliferative Activities
Abstract
:1. Introduction
2. Results and Discussion
2.1. Extraction Yield, Total Phenolic, Total Flavonoid and Ortho-Diphenols Content
2.2. Profiling and Quantification of Individual Compounds by HPLC-DAD and HPLC-ESI-MSn
2.3. In Vitro Antioxidant Activity Assessment
2.4. T. capitellatus Extracts Inhibit Key Enzymes and Show Therapeutic Potential
2.5. Anti-Proliferative Activity of T. capitellatus Extracts
3. Materials and Methods
3.1. Standards and Reagents
3.2. Plant Material
3.3. Preparation of Extracts
3.4. Total Phenolic Compounds, Ortho-Diphenols and Total Flavonoids Content
3.5. Profiling and Quantification of Individual Phenolic Compounds by HPLC-DAD and HPLC-ESI-MSn
3.6. Quantification of Oleanolic and Ursolic Acids in Hydroethanolic Extracts
3.7. In Vitro Antioxidant Activity Assessment
3.7.1. ABTS Radical Cation (ABTS+•) Scavenging Assay
3.7.2. Hydroxyl Radicals Scavenging Assay
3.7.3. Nitric Oxide Radical Scavenging Assay
3.7.4. Superoxide Radical (O2•−) Scavenging Assay
3.7.5. β-Carotene Bleaching Assay
3.8. In Vitro Enzymatic Inhibition Assays
3.9. Cell Cultures and In Vitro Cell Viability Assay
3.10. Data and Statistical Analysis
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Thymus capitellatus | ||||
---|---|---|---|---|
AD | HE | E.M.E. | ||
Extraction yield (%, w/w) | 15.82 ± 2.30 | 16.84 ± 2.43 | n.s. | |
Chemical composition | ||||
Total phenols content (mg caffeic acid equivalent/g) | Ext. | 150.29 ± 5.29 | 140.81 ± 5.42 | n.s. |
D.P. | 23.77 ± 0.84 | 23.72 ± 0.91 | n.s. | |
Ortho-diphenols content (mg caffeic acid equivalent/g) | Ext. | 134.01 ± 5.08 | 146.02 ± 3.62 | * |
D.P. | 21.36 ± 0.80 | 24.60 ± 0.61 | * | |
Total flavonoids content (mg catechin equivalent/g) | Ext. | 174.26 ± 11.58 | 188.84 ± 7.81 | n.s. |
D.P. | 27.56 ± 1.83 | 31.81 ± 1.31 | * |
Compound | R.T. (min) | ESI-MS2 | Quantification | |||||
---|---|---|---|---|---|---|---|---|
HE | AD | E.M.E. Sig. | ||||||
mg/g D.P. | mg/g Extract | mg/g D.P. | mg/g Extract | |||||
1 | Unknown | 21.73 ± 0.11 | [459]:161 | n.q. | n.q. | n.q. | n.q. | |
2 | Unknown | 23.13 ± 0.08 | [509]:463;441;329;295 | n.q. | n.q. | n.q. | n.q. | |
3 | Apigenin-(6,8)-C-diglucoside | 23.19 ± 0.08 | [593]:575;503;473;383;353 | n.q. | n.q. | n.q. | n.q. | |
4 | Unknown | 23.48 ± 0.02 | [455]:409;387;317;233;173 | n.q. | n.q. | n.q. | n.q. | |
5 | Hydroxyjasmonic acid-(?)-O-hexoside | 23.44 ± 0.11 | [387]:369;225;207;163 | n.q. | n.q. | n.q. | n.q. | |
6 | Caffeic acid | 23.76 ± 0.08 | [179]:135 | 0.25 ± 0.02 | 1.49 ± 0.13 | 0.63 ± 0.12 | 3.99 ± 0.73 | * |
7 | Eriodictyol-(?)-O-hexoside | 24.20 ± 0.14 | [449]:287 | 0.49 ± 0.06 | 2.9 ± 0.38 | 0.25 ± 0.14 | 1.61 ± 0.9 | * |
8 | Unknown | 24.27 ± 0.09 | [495]:427;341;333;315 | n.q. | n.q. | n.q. | n.q. | |
9 | Eriodictyol-(?)-O-hexoside | 27.16 ± 0.21 | [449]:287 | 0.84 ± 0.1 | 4.99 ± 0.61 | 0.38 ± 0.12 | 2.43 ± 0.79 | * |
10 | Quercetin-(?)-O-hexoside | 27.33 ± 0.22 | [463]:301 | 5.91 ± 0.68 | 35.11 ± 4.02 | 0.67 ± 0.44 | 4.23 ± 2.78 | * |
11 | Luteolin-(?)-O-hexoside | 29.28 ± 0.12 | [447]:285 | 0.55 ± 0.06 | 3.26 ± 0.35 | 0.16 ± 0.07 | 1.01 ± 0.42 | * |
12 | Luteolin-(?)-O-hexoside | 31.17 ± 0.18 | [447]:285 | 3.94 ± 0.44 | 23.38 ± 2.6 | 0.42 ± 0.13 | 2.63 ± 0.84 | * |
13 | Salvianolic acid A isomer | 33.84 ± 0.19 | [493]:383;313;295 | 0.32 ± 0.04 | 1.92 ± 0.24 | 0.25 ± 0.04 | 1.6 ± 0.26 | * |
14 | Luteolin-(?)-O-hexuronide | 33.87 ± 0.24 | [461]:285 | n.q. | n.q. | n.q. | n.q. | |
15 | Quercetin-(?)-O-(caffeoyl)-hexoside | 33.96 ± 0.25 | [625]:463;323;301 | 1.7 ± 0.08 | 10.07 ± 0.49 | 0.56 ± 0.28 | 3.51 ± 1.76 | * |
16 | Chrysoeriol-(?)-O-hexoside | 34.83 ± 0.08 | [461]:299 | n.q. | n.q. | n.q. | n.q. | |
17 | Rosmarinic acid | 35.19 ± 0.04 | [359]:223;179;161 | 3.66 ± 0.34 | 21.71 ± 2.03 | 1.01 ± 0.61 | 6.37 ± 3.84 | * |
18 | Apigenin-(?)-O-hexoside | 35.79 ± 0.06 | [431]:269 | 0.12 ± 0.02 | 0.7 ± 0.13 | 0.1 ± 0.03 | 0.61 ± 0.19 | n.s. |
19 | Acetyl-luteolin-(?)-O-hexoside-pentoside | 36.09 ± 0.40 | [621]:579;561;447;327;285 | 0.44 ± 0.02 | 2.59 ± 0.13 | 0.84 ± 0.17 | 5.33 ± 1.1 | * |
20 | Unknown | 36.37 ± 0.05 | [549]:531;489;387;207;161 | n.q. | n.q. | n.q. | n.q. | |
21 | Salvianolic acid K | 36.95 ± 0.10 | [555]:537;493;359 | 0.83 ± 0.06 | 4.91 ± 0.37 | 0.64 ± 0.2 | 4.06 ± 1.25 | n.s. |
22 | Quercetin -(?)-O-hexoside-deoxy-hexoside | 38.17 ± 0.05 | [609]:463;301 | 0.28 ± 0.03 | 1.64 ± 0.15 | 0.08 ± 0.03 | 0.51 ± 0.21 | * |
23 | Quercetin-(?)-O-hexoside-hexuronide | 39.07 ± 0.38 | [639]:301 | 1.03 ± 0.05 | 6.09 ± 0.31 | 0.4 ± 0.14 | 2.51 ± 0.91 | * |
24 | Salvianolic acid K isomer | 40.76 ± 0.14 | [555]:493;359 | 0.16 ± 0.01 | 0.93 ± 0.03 | 0.03 ± 0.01 | 0.16 ± 0.05 | * |
25 | Luteolin-(?)-O-hexoside-hexoside | 43.06 ± 0.25 | [609]:447;323;285 | 0.85 ± 0.09 | 5.06 ± 0.53 | 0.22 ± 0.03 | 1.36 ± 0.2 | * |
26 | Chrysoeriol-(?)-O-hexoside-hexoside | 43.10 ± 0.15 | [623]:461;323;299;285 | 0.33 ± 0.03 | 1.94 ± 0.19 | 0.23 ± 0.05 | 1.48 ± 0.32 | n.s. |
27 | Luteolin | 49.05 ± 0.23 | [285]:241;217;199;75;151 | 0.65 ± 0.11 | 3.85 ± 0.66 | 0.42 ± 0.15 | 2.67 ± 0.93 | n.s. |
28 | Oleanolic acid | 6.02 ± 1.35 | 35.77 ± 8.04 | n.d. | n.d. | * | ||
29 | Ursolic acid | 4.88 ± 1.07 | 28.97 ± 6.38 | n.d. | n.d. | * | ||
Total phenolic compounds | 23.07 ± 1.48 | 137.67 ± 8.77 | 7.84 ± 2.14 | 49.55 ± 13.51 | * | |||
Total flavonoids | 17.68 ± 1.17 | 104.97 ± 6.95 | 5.19 ± 1.33 | 32.8 ± 8.42 | * | |||
Total phenolic acids | 5.21 ± 0.44 | 30.96 ± 2.63 | 2.65 ± 0.89 | 16.75 ± 5.64 | * | |||
Total terpenoids | 10.90 ± 2.43 | 64.74 ± 14.4 | n.d. | n.d. | * |
Thymus capitellatus Extracts (mg/mL) | ||||
---|---|---|---|---|
AD | HE | E.M.E. | ||
Acetylcholinesterase | IC50 | 0.79 ± 0.05 | 0.36 ± 0.04 | * |
0.5 mg/mL | 34.03 ± 3.83 | 54.22 ± 6.84 | * | |
1 mg/mL | 55.72 ± 6.39 | 69.28 ± 10.22 | n.s. | |
Tyrosinase | 0.5 mg/mL | 16.56 ± 4.26 | 17.58 ± 0.33 | n.s. |
1 mg/mL | 22.37 ± 1.29 | 28.17 ± 1.73 | * | |
Elastase | 0.5 mg/mL | - | - | n.s. |
1 mg/mL | 7.16 ± 1.50 | - | * | |
α-Amylase | 0.5 mg/mL | 3.17 ± 0.5 | 4.92 ± 0.19 | * |
1 mg/mL | 4.10 ± 0.18 | 8.71 ± 0.59 | * | |
α-Glucosidase | 0.5 mg/mL | 16.74 ± 1.01 | 13.30 ± 1.4 | * |
1 mg/mL | 24.57 ± 0.24 | 23.02 ± 1.12 | n.s |
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Martins-Gomes, C.; Steck, J.; Keller, J.; Bunzel, M.; Nunes, F.M.; Silva, A.M. Molecular Characterization of Thymus capitellatus Extracts and Their Antioxidant, Neuroprotective and Anti-Proliferative Activities. Int. J. Mol. Sci. 2022, 23, 15187. https://doi.org/10.3390/ijms232315187
Martins-Gomes C, Steck J, Keller J, Bunzel M, Nunes FM, Silva AM. Molecular Characterization of Thymus capitellatus Extracts and Their Antioxidant, Neuroprotective and Anti-Proliferative Activities. International Journal of Molecular Sciences. 2022; 23(23):15187. https://doi.org/10.3390/ijms232315187
Chicago/Turabian StyleMartins-Gomes, Carlos, Jan Steck, Judith Keller, Mirko Bunzel, Fernando M. Nunes, and Amélia M. Silva. 2022. "Molecular Characterization of Thymus capitellatus Extracts and Their Antioxidant, Neuroprotective and Anti-Proliferative Activities" International Journal of Molecular Sciences 23, no. 23: 15187. https://doi.org/10.3390/ijms232315187