Extracts from Cephalaria Uralensis (Murray) Roem. & Schult. and Cephalaria Gigantea (Ledeb.) Bobrov as Potential Agents for Treatment of Acne Vulgaris: Chemical Characterization and In Vitro Biological Evaluation
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals and Reagents
2.2. Plant Material
2.3. Preparation of the Extracts
2.4. LC-ESI-MS/MS Analysis
Quantification of Major Compounds by UHPLC–DAD
2.5. Antioxidant Activity
2.5.1. DPPH● Assay
2.5.2. ABTS●+ Assay
2.5.3. Metal Chelating Activity
2.6. Anti-Inflammatory Activity
2.7. Antimicrobial Activity
2.7.1. Bacterial Strains
2.7.2. Agar Disc Diffusion Assay
2.7.3. MIC and MBC Determination
2.7.4. Synergy Test
2.8. Cytotoxicity Evaluation
2.9. Statistical Analysis
3. Results and Discussion
3.1. Qualitative LC-DAD-MS3 Analysis of the Chemical Composition of C. uralensis and C. gigantea
3.2. Antioxidant Activity
3.3. Anti-Inflammatory Activity
3.4. Antimicrobial Activity
3.5. Cytotoxic Activity
4. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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No | Compound Name | Retention Time [min] | UV Maxima [nm] | [M-H]- m/z | MS2 Ions | CUA | CUE | CUM | CUEf | CUMf | CGA | CGE | CGM |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1 | 3-O-caffeoylquinic acid (neochlorogenic acid) c | 16.1 | 300sh,324 | 353 | 191b, 179 | 4.43 ± 0.13 | 8.75 ± 0.62 | 3.87 ± 0.08 | 3.42 ± 0.11 | 8.54 ± 0.42 | 5.45 ± 0.32 | 9.35 ± 0.17 | 5.13 ± 0.18 |
2 | phenolic acid derivative | 20.4 | 300sh 324 | 369 | 207b | 0.61 ± 0.04 | - | - | - | 20.65 ± 0.17 | - | - | - |
3 | loganic acid s | 20.6 | 231 | 375 | 213b, 169 | 3.92 ± 0.11 | 4.60 ± 0.07 | 0.83 ± 0.02 | 1.35 ± 0.23 | - | 13.47 ± 0.23 | 22.17 ± 0.45 | 14.05 ± 0.17 |
4 | loganic acid isomer | 21.9 | 231 | 375 | 213b, 169 | - | - | - | - | - | 14.14 ± 0.09 | 22.45 ± 0.11 | 14.78 ± 0.25 |
5 | caffeic acid s | 22.2 | 300sh, 325 | 179 | - | 0.84 ± 0.19 | 1.27 ± 0.09 | - | 0.91 ± 0.05 | 0.79 ± 0.11 | - | - | - |
6 | caffeoylquinic acid isomer | 22.3 | 300sh, 325 | 353 | 191b | 4.27 ± 0.10 | 4.99 ± 0.05 | - | 1.96 ± 0.02 | - | - | - | - |
7 | 5-O-caffeoylquinic acid (chlorogenic acid) c | 22.8 | 300sh, 325 | 353 | 191b,179 | 123.75 ± 0.54 | 114.90 ± 1.06 | 132.18 ± 1.07 | 94.90 ± 0.42 | 98.75 ± 0.61 | 101.79 ± 0.51 | 135.83 ± 1.47 | 130.88 ± 0.77 |
8 | undefined iridoid | 23.2 | 245 | 389 | - | - | - | - | - | - | 16.03 ± 0.19 | 31.48 ± 0.62 | 22.02 ± 0.15 |
9 | 4-O-caffeoylquinic acid (cryptochlorogenic acid) c | 24.3 | 299sh, 324 | 353 | 191, 179, 173b | 1.89 ± 0.01 | 4.01 ± 0.05 | 1.68 ± 0.06 | - | 7.45 ± 0.19 | 16.02 ± 0.06 | 20.80 ± 0.16 | 16.38 ± 0.08 |
10 | undefined compound | 27.8 | 213, 280 | 355 | 225, 179b | - | - | - | - | - | 14.72 ± 0.09 | 17.71 ± 0.12 | 4.97 ± 0.10 |
11 | caffeoylquinic acid isomer | 26.1 | 299, 325 | 353 | 191b | 3.69 ± 0.05 | 3.92 ± 0.09 | - | - | - | - | - | - |
12 | deoxyloganic acid t | 27.0 | 242 | 359 | 322b, 209 | 2.14 ± 0.17 | 2.67 ± 0.42 | 2.39 ± 0.08 | 1.85 ± 0.12 | - | 14.82 ± 0.12 | 17.05 ± 0.31 | 15.21 ± 0.62 |
13 | caffeoylquinic acid isomer | 27.3 | 300sh, 324 | 353 | 191b | 7.50 ± 0.08 | 4.15 ± 0.01 | 1.97 ± 0.05 | 12.62 ± 0.35 | 2.76 ± 0.02 | 3.84 ± 0.05 | 4.85 ± 0.15 | 3.92 ± 0.01 |
14 | flavonoid derivative | 27.5 | 261, 353 | 625 | 607, 535, 505b, 463, 343 | 8.28 ± 0.18 | 4.62 ± 0.05 | 3.51 ± 0.10 | 2.69 ± 0.07 | - | 14.89 ± 0.15 | 8.00 ± 0.09 | 15.23 ± 0.08 |
15 | loganin s | 28.7 | 249 | 435f | 389, 227b | - | - | - | 0.51 ± 0.02 | - | 4.33 ± 0.12 | 6.64 ± 0.18 | 4.56 ± 0.05 |
16 | undefined iridoid | 29.9 | 248 | 535f | 489b, 399, 293, 195 | 0.17 ± 0.03 | - | - | 0.47 ± 0.01 | - | - | - | - |
17 | undefined iridoid | 30.7 | 230 | 433f | 387b, 355, 265, 225, 155 | - | - | - | - | - | 3.41 ± 0.12 | 5.55 ± 0.21 | 3.18 ± 0.02 |
18 | undefined iridoid | 31.6 | 230 | 433f | 387b, 355, 265, 225, 155 | - | - | - | - | - | 2.75 ± 0.11 | 2.53 ± 0.08 | 1.61 ± 0.01 |
19 | undefined iridoid | 32.0 | 224 | 403f | 371b, 333, 223, 121 | - | - | - | - | - | 3.52 ± 0.05 | 2.72 ± 0.10 | 1.72 ± 0.01 |
20 | undefined iridoid | 33.9 | 248 | 488 | 471, 350, 341b, 281, 146 | - | - | - | 1.20 ± 0.07 | - | - | - | - |
21 | isovitexin O-hexoside | 34.8 | 267, 334 | 593 | 473, 431b, 341, 311, 283 | - | - | - | - | - | 2.82 ± 0.06 | 2.98 ± 0.05 | 2.15 ± 0.02 |
22 | isoorientin s | 36.5 | 270, 349 | 447 | 429, 357, 327b | 65.18 ± 0.23 | 41.71 ± 0.50 | 61.90 ± 0.81 | 51.72 ± 0.16 | 48.50 ± 0.23 | 108.42 ± 0.79 | 86.84 ± 0.43 | 79.15 ± 0.17 |
23 | swertiajaponin t | 37.4 | 270, 348 | 461 | 341b, 313, 297 | 93.05 ± 1.33 | 72.63 ± 0.86 | 104.72 ± 0.67 | 7.91 ± 0.08 | 40.19 ± 0.38 | 115.10 ± 0.45 | 82.17 ± 0.57 | 80.45 ± 1.11 |
24 | isovitexin s | 40.8 | 269, 337 | 431 | 413, 341, 311b | 4.67 ± 0.15 | 1.87 ± 0.03 | 1.28 ± 0.11 | 4.20 ± 0.09 | - | - | - | - |
25 | phenolic acid derivative | 40.8 | 267, 330 | 545 | 375b, 195 | 2.19 ± 0.02 | 0.98 ± 0.01 | 1.12 ± 0.02 | 2.83 ± 0.08 | - | - | - | - |
26 | quercetin 3-O-galactoside (hyperoside) s | 41.1 | 260, 353 | 463 | 301b, 179 | 0.86 ± 0.03 | - | - | - | - | - | - | - |
27 | ferulic acid s | 41.7 | 300sh, 325 | 193 | - | - | 1.16 ± 0.05 | - | - | - | - | - | - |
28 | apigenin derivative | 42.1 | 269, 333 | 445 | 413, 325b, 293, 231 | 8.53 ± 0.15 | 5.97 ± 0.11 | 8.17 ± 0.09 | - | - | 12.41 ± 0.21 | 10.69 ± 0.13 | 9.66 ± 0.07 |
29 | undefined iridoid | 44.6 | 240 | 527 | 365b, 295, 179 | 4.63 ± 0.08 | 4.27 ± 0.02 | 1.17 ± 0.05 | - | - | - | - | - |
30 | phenolic acid derivative | 45.8 | 300sh, 322 | 587 | 555, 375b, 195 | 1.73 ± 0.03 | - | - | - | - | 1.52 ± 0.08 | 1.27 ± 0.05 | 1.61 ± 0.05 |
31 | flavonoid derivative with p-coumaroyl moiety | 46.1 | 282, 315 | 747 | 601, 585b, 485, 357, 227 | 13.02 ± 0.12 | 23.19 ± 0.35 | 14.09 ± 0.17 | 196.02 ± 0.62 | 10.51 ± 0.27 | 8.17 ± 0.15 | 10.05 ± 0.18 | 11.76 ± 0.23 |
32 | 3,5-O-dicaffeoylquinic acid c | 47.3 | 300sh, 324 | 515 | 353b, 191, 179 | 64.93 ± 0.25 | 58.35 ± 0.11 | 70.26 ± 0.36 | 48.30 ± 1.01 | 41.29 ± 0.18 | 105.75 ± 0.37 | 118.90 ± 0.46 | 73.53 ± 1.12 |
33 | undefined compound | 49.3 | 225 | 745 | 583b, 565, 513, 459 | 1.94 ± 0.03 | 2.47 ± 0.05 | - | 31.52 ± 0.17 | - | - | - | - |
34 | 4,5-O-dicaffeoylquinic acid c | 50.9 | 300sh, 325 | 515 | 353b, 179, 173 | 17.81 ± 1.01 | 8.07 ± 0.35 | 9.75 ± 0.62 | 7.65 ± 0.30 | 7.18 ± 0.15 | 11.57 ± 0.06 | 13.43 ± 0.20 | 12.12 ± 0.08 |
35 | phenolic acid derivative | 54.9 | 290, 324 | 631 | 583, 373, 193 | - | - | - | 92.85 ± 0.71 | - | 0.78 ± 0.02 | 1.79 ± 0.05 | 0.83 ± 0.01 |
36 | undefined compound | 55.6 | 233 | 791 | 630b, 495, 459, 419, 239 | 1.18 ± 0.04 | 1.54 ± 0.02 | 1.38 ± 0.02 | - | - | - | - | - |
37 | undefined compound | 57.6 | 225 | 633 | 419b, 239 | - | - | - | 0.81 ± 0.01 | - | - | - | - |
38 | undefined compound | 62.2 | 227 | 629 | 597,419b,239 | - | - | - | 0.49 ± 0.02 | - | - | - | - |
39 | tiliroside s | 63.0 | 260, 316 | 593 | 447,285b | - | - | - | - | - | 0.57 ± 0.05 | 0.61 ± 0.02 | 0.44 ± 0.02 |
40 | flavonoid derivative with p-coumaroyl moiety | 69.1 | 261, 315 | 635 | 575,489,349,285b | - | - | - | - | - | 20.20 ± 0.19 | 23.52 ± 0.25 | 7.92 ± 0.05 |
41 | flavonoid derivative with p-coumaroyl moiety | 69.5 | 261, 315 | 635 | 575, 489, 349, 285b | - | - | - | - | - | 7.52 ± 0.11 | 8.12 ± 0.09 | 8.27 ± 0.01 |
Extract | DPPH● [mg/mL ± SD] | ABTS●+ [mg/mL ± SD] | CHEL [mg/mL ± SD] |
---|---|---|---|
CUA | 4.42 ± 0.53 *** | 0.61 ± 0.12 ** | 0.49 ± 0.17 |
CUM | 2.86 ± 0.12 *** | 0.58 ± 0.16 ** | 0.25 ± 0.11 |
CUE | 5.55 ± 0.10 *** | 0.72 ± 0.11 *** | 1.01 ± 0.13 ** |
CUMf | 6.07 ± 0.40 *** | 0.45 ± 0.21 * | 1.20 ± 0.13 *** |
CUEf | 6.87 ± 0.72 *** | 0.66 ± 0.27 *** | 1.07 ± 0.25 *** |
CGA | 5.56 ± 0.23 *** | 0.53 ± 0.16 ** | 4.04 ± 0.53 *** |
CGM | 7.28 ± 0.52 *** | 0.54 ± 0.21 ** | 1.32 ± 0.70 *** |
CGE | 4.90 ± 0.62 *** | 0.57 ± 0.33 ** | 2.95 ± 0.13 *** |
AA | 0.48 ± 0.30 | - | - |
Trolox | - | 0.09 ± 0.10 | - |
Na2EDTA·2H2O | - | - | 0.01 ± 0.01 |
Extract | COX-1 Inibition [% ± SD] | COX-2 Inhibition [% ± SD] | ||
---|---|---|---|---|
50 µg/mL | 100 µg/mL | 50 µg/mL | 100 µg/mL | |
CUA | 56.99 ± 1.81 *** | 90.82 ± 3.43 *** | 60.60 ± 2.46 *** | 91.12 ± 4.38 |
CUM | 80.07 ± 2.65 ** | 97.90 ± 2.32 *** | 68.31 ± 1.34 *** | 94.85 ± 3.29 * |
CUE | 76.69 ± 1.29 | 92.54 ± 3.28 *** | 71.52 ± 2.38 *** | 75.31 ± 2.15 ** |
CUMf | 74.44 ± 3.18 | 94.64 ± 2.26 *** | 55.24 ± 1.10 *** | 87.50 ± 2.29 |
CUEf | 46.07 ± 2.25 *** | 67.80 ± 2.34 | 23.52 ± 1.37 *** | 35.33 ± 0.93 *** |
CGA | 32.23 ± 1.28 *** | 45.44 ± 1.23 *** | 52.28 ± 2.19 *** | 55.75 ± 1.26 *** |
CGM | 17.01 ± 0.79 *** | 31.04 ± 1.15 *** | 22.83 ± 1.13 *** | 43.07 ± 2.25 *** |
CGE | 50.99 ± 1.35 *** | 58.11 ± 3.36 *** | 69.00 ± 2.27 *** | 81.49 ± 1.28 |
Bacterial Strains | Zones of Bacterial Growth Inhibition [mm] | |||||||
---|---|---|---|---|---|---|---|---|
CUA | CUM | CUE | CUMf | CUEf | CGA | CGM | CGE | |
S. aureus ATCC 25923 | 13 | 17 | 12 | 13.5 | 10 | 8 | 7 | 8 |
S. epidermidis ATCC 12228 | 12.5 | 19 | 14.5 | 10.5 | 10 | 10 | 8 | 10 |
P. acnes PCM 2400 | 18 | 23 | 15 | 13 | 11 | 6 | 4 | 8 |
P. acnes PCM 2334 | 17.5 | 21.5 | 16 | 13 | 11.5 | 8 | 7 | 10 |
Bacterial Strains | CUA | CUM | CUE | CUMf | CUEf | CGA | CGM | CGE | ||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
MIC | MBC/MIC | MIC | MBC/MIC | MIC | MBC/MIC | MIC | MBC/MIC | MIC | MBC/MIC | MIC | MBC/MIC | MIC | MBC/MIC | MIC | MBC/MIC | |
S. aureus ATCC 25923 | 50 | 8 | 25 | 8 | 100 | 8 | 50 | 8 | 200 | 8 | >200 | - | >200 | - | >200 | - |
S. epidermidis ATCC 12228 | 100 | 8 | 25 | 8 | 50 | 8 | 100 | 8 | 200 | 8 | >200 | - | >200 | - | >200 | - |
P. acnes PCM 2400 | 25 | 8 | 12.5 | 2 | 50 | 8 | 50 | 8 | 100 | 8 | >200 | - | >200 | - | >200 | - |
P. acnes PCM 2334 | 25 | 8 | 12.5 | 4 | 50 | 8 | 50 | 8 | 100 | 8 | >200 | - | >200 | - | 200 | - |
Bacterial Strains | FICIa Index of Different Combinations of Antibiotics and C. uralensis Extracts | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
CUA | CUM | CUE | ||||||||||
Cefepime | Ceftriaxone | Ciprofloxacin | Sparfloxacin | Cefepime | Ceftriaxone | Ciprofloxacin | Sparfloxacin | Cefepime | Ceftriaxone | Ciprofloxacin | Sparfloxacin | |
S. aureus | 2 d | 1.5 d | 1.06 d | 1.5 d | 2 d | 1.06 d | 1.5 d | 1.5 d | 1.5 d | 2 d | 2 d | 2 d |
S. epidermidis | 1.06 d | 1.5 d | 1.06 d | 1.5 d | 1.06 d | 1.06 d | 1.5 d | 1.06 d | 1.5 d | 1.5 d | 1.5 d | 2 d |
P. acnes PCM 2400 | 1.06 d | 2 d | 2 d | 1.5 d | 0.5 b | 0.5 b | 1.0 d | 1.06 d | 1.5 d | 1.5 d | 1.06 d | 1.5 d |
P. acnes PCM 2334 | 1.06 d | 1.06 d | 1.5 d | 1.06 d | 0.5 b | 0.375 b | 0.562 c | 1.06 d | 1.06 d | 1.5 d | 1.06 d | 1.06 d |
Extract | CC50 [μg/mL] | TI | |||
---|---|---|---|---|---|
S. aureus ATCC 25923 | S. epidermidis ATCC 12228 | P. acnes PCM 2400 | P. acnes PCM 2334 | ||
CUA | 191.60 ± 3.25 | 3.83 | 1.92 | 7.66 | 7.66 |
CUM | 61.27 ± 2.74 | 2.45 | 2.45 | 4.90 | 4.90 |
CUE | > 1000 | > 10 | > 20 | > 20 | > 20 |
CUMf | 72.09 ± 2.16 | 1.44 | 0.72 | 1.44 | 1.44 |
CUEf | > 1000 | > 5 | > 5 | > 10 | >10 |
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Chrząszcz, M.; Miazga-Karska, M.; Klimek, K.; Granica, S.; Tchórzewska, D.; Ginalska, G.; Szewczyk, K. Extracts from Cephalaria Uralensis (Murray) Roem. & Schult. and Cephalaria Gigantea (Ledeb.) Bobrov as Potential Agents for Treatment of Acne Vulgaris: Chemical Characterization and In Vitro Biological Evaluation. Antioxidants 2020, 9, 796. https://doi.org/10.3390/antiox9090796
Chrząszcz M, Miazga-Karska M, Klimek K, Granica S, Tchórzewska D, Ginalska G, Szewczyk K. Extracts from Cephalaria Uralensis (Murray) Roem. & Schult. and Cephalaria Gigantea (Ledeb.) Bobrov as Potential Agents for Treatment of Acne Vulgaris: Chemical Characterization and In Vitro Biological Evaluation. Antioxidants. 2020; 9(9):796. https://doi.org/10.3390/antiox9090796
Chicago/Turabian StyleChrząszcz, Małgorzata, Małgorzata Miazga-Karska, Katarzyna Klimek, Sebastian Granica, Dorota Tchórzewska, Grażyna Ginalska, and Katarzyna Szewczyk. 2020. "Extracts from Cephalaria Uralensis (Murray) Roem. & Schult. and Cephalaria Gigantea (Ledeb.) Bobrov as Potential Agents for Treatment of Acne Vulgaris: Chemical Characterization and In Vitro Biological Evaluation" Antioxidants 9, no. 9: 796. https://doi.org/10.3390/antiox9090796