Chemical Composition and Antioxidant, Anti-Inflammatory, and Enzyme Inhibitory Activities of an Endemic Species from Southern Algeria: Warionia saharae
Abstract
:1. Introduction
2. Results and Discussion
2.1. UHPLC-DAD-ESI-MS/MSn Characterization of W. saharae Extract
2.2. GC–MS Characterization of W. saharae Extract
2.3. Total Bioactive Content
2.4. Antioxidant Activities
2.5. Anti-Inflammatory Activity
2.6. Enzyme Inhibitory Activities
2.7. Molecular Docking
3. Materials and Methods
3.1. Chemicals
3.2. Extract Preparation
3.3. Total Bioactive Content
3.3.1. Total Phenolic Content
3.3.2. Total Flavonoid Content
3.4. UHPLC-DAD-ESI-MS/MSn Characterization of W. saharae Extract
3.5. GC–MS Characterization of W. saharae Extract
3.6. Antioxidant Activities
3.6.1. Determination of 1,1-Diphenyl-2-Picrylhydrazyl Radical Scavenging Activity
3.6.2. Determination of 2,2′-Azinobis(3-Ethylbenzothiazoline-6-Sulfonic Acid) Scavenging Activity
3.6.3. Galvinoxyl Radical Scavenging Activity
3.6.4. Ferric Reducing Power Assay
3.6.5. Cupric Ion Reducing Antioxidant Capacity Assay
3.7. Anti-Inflammatory Activity
3.8. Inhibition of Enzymatic Activities
3.8.1. Inhibition of α-Glucosidase Activity
3.8.2. Inhibition of α-Amylase Activity
3.8.3. Inhibition of Acetylcholinesterase Activity
3.9. Molecular Docking Study
3.10. Statistical Analysis
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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N° | RT | Λmax | [M − H]− | MS2 (m/z) | Identified Compound | Quantification (µg/mg Extract) |
---|---|---|---|---|---|---|
1 | 1.53 | 256 | 215 | 179,160 | Caffeic acid adduct with chloride | NQ |
2 | 1.75 | 194 | 137 | 110,82 | Hydroxybenzoic acid | 0.855 ± 0.037 |
3 | 6.58 | 204,224,250,289,340 | 339 | 177 | Esculetin-6-O-glucoside | NQ |
4 | 8.05 | 325,238,218 | 353 | 191,179 | 5-O-CQA | 10.333 ± 2.360 |
5 | 8.29 | 203,225,337 | 353 | 191,179 | 3-O-CQA | 1.537 ± 0.239 |
6 | 8.46 | 202,225,298,342 | 353 | 191,179,173,135 | 4-O-CQA | 3.039 ± 0.420 |
7 | 8.84 | 299,235,322 | 179 | 135 | Caffeic acid | 1.380 ± 0.790 |
8 | 9.06 | 260 | 536 | - | Unknown | NQ |
9 | 10.54 | 198,229,288 | 515 | 353 | O-diCQA isomer | 1.631 ± 0.430 |
10 | 10.96 | 234,288,330 | 477 | 301 | Quercetin glucuronide | 0.560 ± 0.110 |
11 | 11.23 | 232,290 | 515 | 353,335,179 | 3,5-O-diCQA | 1.280 ± 0.190 |
12 | 11.76 | 261 | 609 | 459,315,299 | Unknown | NQ |
13 | 12.03 | 204,256,353 | 463 | 301,300 | Quercetin-O-hexoside | 2.460 ± 0.790 |
14 | 12.15 | 227,289 | 303 | 285,175,125 | Taxifolin | 62.800 ± 16.690 |
15 | 12.47 | 231,290 | 303 | 285,177 | Taxifolin isomer | 1.540 ± 0.590 |
16 | 12.60 | 236,256,268,341 | 477 | 315,300 | Isorhamnetin-O-hexoside | 0.640 ± 0.130 |
17 | 12.78 | 220,241,324 | 515 | 353,335,172,191 | 3,4-O-diCQA | 4.185 ± 1.340 |
18 | 13.03 | 220,241,324 | 515 | 353,335,191 | 1,3-O-diCQA | 43.120 ± 17.390 |
19 | 13.67 | 219,242,326 | 515 | 353,299,255,203 | 4,5-O-diCQA | 9.660 ± 2.970 |
20 | 15.97 | 207,254,351 | 285 | 241,217,199,175 | Luteolin | 7.410 ± 0.530 |
21 | 17.91 | 245,274,332 | 299 | 284 | 3′-O-Methylluteolin (Chrysoeriol) | 0.740 ± 0.520 |
22 | 18.07 | 246,342 | 299 | 284 | Luteolin 4′-methyl ether (Diosmetin) | Tr |
23 | 18.43 | 296,234 | 315 | 300 | Isorhamnetin | 3.435 ± 1.390 |
24 | 18.76 | 200,230,290 | 299 | 271,255,243 | Naringenin derivative | NQ |
Families | Peak | Rt (min) | Identified Compound * | Quantification |
---|---|---|---|---|
Carboxylic acids and esters Total=124.6 µg/mg | 4 | 24.259 | Malic acid | 50.79 ± 5.67 |
11 | 33.568 | Citric acid | 4.01 ± 1.98 | |
13 | 34.517 | Quinic acid | 18.53 ± 2.19 | |
14 | 34.960 | 2-n-Propyl valerate | 4.63 ± 0.47 | |
23 | 37.945 | D-Gluconic acid | 17.11 ± 1.37 | |
28 | 41.191 | Caffeic acid | 6.02 ± 0.72 | |
37 | 62.690 | Chlorogenic acid 1 | 19.89 ± 2.89 | |
39 | 65.073 | Chlorogenic acid 2 | 3.62 ± 0.77 | |
Fatty acids Total=11.364 µg/mg | 3 | 18.452 | Butanedioic acid | 3.58 ± 0.56 |
25 | 39.147 | Palmitic acid | 5.73 ± 0.12 | |
29 | 42.814 | Linoelaidic acid | 1.056 ± 0.80 | |
30 | 42.961 | Oleic acid | 0.98 ± 0.11 | |
Alcohols Total=128.520 µg/mg | 2 | 17.099 | Glycerol | 12.03 ± 2.07 |
5 | 30.892 | D-arabitol | 2.17 ± 0.66 | |
16 | 35.335 | Dulcitol | 31.99 ± 1.93 | |
21 | 36.916 | Myo-inositol | 60.91 ± 6.91 | |
24 | 38.630 | Scyllo-Inositol | 4.24 ± 0.90 | |
26 | 40.015 | Myo-Inositol | 17.18 ± 3.16 | |
Sugars Total=214.735 µg/mg | 6 | 32.041 | Ribonic acid | Tr |
7 | 32.222 | D-Talose | Tr | |
8 | 32.379 | D-Tagatose | Tr | |
9 | 33.230 | D-Fructose (isomer 1) a | 51.21 ± 14.36 | |
10 | 33.442 | D-Fructose (isomer 2) a | 32.19 ± 19.31 | |
12 | 34.249 | D-Galactose (isomer 1) b | 2.18 ± 0.14 | |
17 | 35.393 | D-Galactose (isomer 2) b | 34.57 ± 0.46 | |
18 | 35.615 | D-Galactose (isomer 3) b | Tr | |
22 | 37.677 | D-Galactose (isomer 4) b | 19.81 ± 4.66 | |
31 | 51.024 | D-Fructose (isomer 3) a | Tr | |
32 | 51.153 | D-Turanose | Tr | |
33 | 51.515 | Sucrose derivative | 36.27 ± 12.46 | |
34 | 53.916 | D-Trehalose | Tr | |
35 | 56.602 | β-Lyxose | 0.075 ± 0.01 | |
38 | 62.999 | D-Glucose (isomer 1) c | 26.06 ± 4.58 | |
40 | 68.978 | D-Gulose | Tr | |
41 | 69.824 | Sucrose | 12.37 ± 0.03 | |
43 | 71.578 | D-Glucose (isomer 2) c | Tr | |
44 | 72.381 | D-Glucose (isómer 3) c | Tr | |
Other compounds | 1 | 16.930 | Phosphoric acid | NQ |
15 | 35.172 | Gluconolactone | NQ | |
36 | 59.258 | Catechin | NQ | |
27 | 40.082 | Esculetin | NQ | |
19 | 35.829 | Acrylsaeure | NQ | |
42 | 70.226 | 5-Methyluridine | NQ |
Sample | Radical Scavenging Activity IC50 (μg/mL) | Radical Scavenging Activity A0.5 (μg/mL) | |||
---|---|---|---|---|---|
DPPH● | ABTS●+ | Galvinoxyl | FRP | CUPRAC | |
W. saharae | 7.12 ± 0.09 | 4.19 ± 0.35 | 3.55 ± 0.08 | 31.21 ± 0.14 | 3.84 ± 0.16 |
Trolox | 5.12 ± 0.21 | 3.21 ± 0.06 | 4.31 ± 0.05 | 5.25 ± 0.20 | 8.69 ± 0.14 |
BHA | 6.14 ± 0.41 | 1.81 ± 0.10 | 5.38 ± 0.06 | 7.99 ± 0.87 | 6.62 ± 0.05 |
BHT | 12.99 ± 0.41 | 1.29 ± 0.30 | 3.32 ± 0.18 | >200 | 8.97 ± 3.94 |
Ascorbic acid | 4.39 ± 0.01 | 3.04 ± 0.05 | 5.02 ± 0.01 | 3.62 ± 0.29 | 8.31 ± 0.15 |
Sample | Enzyme Inhibitory Activity | ||
---|---|---|---|
α-Glucosidase IC50 (μg/mL) | α-Amylase (% inhibition) | Acetylcholinesterase (% inhibition) | |
W. saharae extract | 23.52 ± 6.33 A | 38.41 ± 5.51 a | 28.578 ± 2.979 b |
Acarbose (μg/mL) | 405.77 ± 34.83 B | ND | ND |
Compound | BE | Amino Acid Involved in Interaction |
---|---|---|
Taxifolin | −5.89 | Asn715, Ile691, Ala687, Gly690. |
4,5-O-Dicaffeoylquinic acid | −4.02 | His206, Ile691, Asn415, Tyr717, Ser693, Ser692, Gly690, Gln219, Val686, Gln208. |
1,3-O-Dicaffeoylquinic acid | −4.17 | Met801, Gln533, Tyr561, Arg536, Asn668, Asp802. |
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Rechek, H.; Haouat, A.; Hamaidia, K.; Allal, H.; Boudiar, T.; Pinto, D.C.G.A.; Cardoso, S.M.; Bensouici, C.; Soltani, N.; Silva, A.M.S. Chemical Composition and Antioxidant, Anti-Inflammatory, and Enzyme Inhibitory Activities of an Endemic Species from Southern Algeria: Warionia saharae. Molecules 2021, 26, 5257. https://doi.org/10.3390/molecules26175257
Rechek H, Haouat A, Hamaidia K, Allal H, Boudiar T, Pinto DCGA, Cardoso SM, Bensouici C, Soltani N, Silva AMS. Chemical Composition and Antioxidant, Anti-Inflammatory, and Enzyme Inhibitory Activities of an Endemic Species from Southern Algeria: Warionia saharae. Molecules. 2021; 26(17):5257. https://doi.org/10.3390/molecules26175257
Chicago/Turabian StyleRechek, Habiba, Ammar Haouat, Kaouther Hamaidia, Hamza Allal, Tarek Boudiar, Diana C. G. A. Pinto, Susana M. Cardoso, Chawki Bensouici, Noureddine Soltani, and Artur M. S. Silva. 2021. "Chemical Composition and Antioxidant, Anti-Inflammatory, and Enzyme Inhibitory Activities of an Endemic Species from Southern Algeria: Warionia saharae" Molecules 26, no. 17: 5257. https://doi.org/10.3390/molecules26175257