Ziziphora taurica subsp. taurica: Analytical Characterization and Biological Activities
Abstract
:1. Introduction
2. Materials and Methods
2.1. Plant Material
2.2. Solvent Extraction
2.3. Chemicals
2.4. Quantification of Phenolic Compounds in the Extracts
2.5. Biological Activity
2.6. Statistical Analysis
3. Results and Discussion
3.1. Total Phenolic (TPC) and Flavonoid (TFC) Content
3.2. LC-ESI-MS/MS Analysis
3.3. Biological Activities
3.3.1. Antioxidant Activities
3.3.2. Enzyme Inhibitory Activities
3.4. Correlations among Phenolic Compounds and Assays
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Extracts | Abbreviation | Yield (%) | Total Phenolics (mg GAEs/g extract) | Total Flavonoids (mg QEs/g extract) |
---|---|---|---|---|
Ethyl Acetate | ZTT-EtOAc | 3.23 | 34.82 ± 0.79 a | 20.87 ± 1.38 b |
Methanol | ZTT-MeOH | 8.93 | 27.49 ± 0.74 b | 37.39 ± 2.54 a |
Water | ZTT-W | 13.69 | 15.10 ± 0.45 c | 7.08 ± 0.58 c |
Compound | ZTT-EtOAc | ZTT-MeOH | ZTT-W | Linear Equation | R2 | LOD (μg/L) | LOQ (μg/L) |
---|---|---|---|---|---|---|---|
(-)-Epicatechin | nd | nd | nd | y = 9.11x−9.99 | 0.9971 | 1.85 | 6.18 |
(+)-Catechin | nd | 11.79 ± 0.21 | nd | y = 1.45x+1.95 | 0.9974 | 3.96 | 13.20 |
2,5-Dihydroxybenzoic Acid | 15.98 ± 0.84 c | 60.48 ± 1.77 b | 268.65 ± 5.24 a | y = 3.79x−14.12 | 0.9980 | 2.12 | 7.08 |
2-Hydroxycinnamic Acid | nd | nd | nd | y = 16.72x−26.94 | 0.9996 | 0.61 | 2.03 |
3,4-Dihydroxyphenylacetic Acid | nd | 3.20 ± 0.21 b | 17.87 ± 0.11 a | y = 5.13x−12.39 | 0.9990 | 1.35 | 4.51 |
3-Hydroxybenzoic Acid | 10.75 ± 0.38 a | 9.16 ± 0.58 ab | 8.12 ± 0.72 c | y = 3.69x−12.29 | 0.9991 | 1.86 | 6.20 |
4-Hydroxybenzoic Acid | 74.92 ± 0.60 b | 76.71 ± 0.88 b | 94.84 ± 1.44 a | y = 7.62x+22.79 | 0.9996 | 1.72 | 5.72 |
Apigenin | 1457.99 ± 24.48 a | 1270.90 ± 0.30 b | 201.25 ± 3.53 c | y = 11.29x+38.05 | 0.9987 | 0.96 | 3.20 |
Apigenin 7-glucoside | 293.07 ± 1.22 b | 847.22 ± 5.96 a | nd | y = 21.33x−31.69 | 0.9983 | 0.41 | 1.35 |
Caffeic acid | 17.42 ± 0.07 c | 44.12 ± 0.92 b | 415.94 ± 2.44 a | y = 11.09x+16.73 | 0.9997 | 3.15 | 10.50 |
Chlorogenic Acid | 48.33 ± 13.46 c | 136.14 ± 1.56 b | 2135.92 ± 2.02 a | y = 12.14x+32.34 | 0.9995 | 0.55 | 1.82 |
Eriodictyol | 82.66 ± 0.31 a | 31.32 ± 0.54 b | 7.39 ± 0.25 c | y = 14.24x−0.50 | 0.9998 | 0.80 | 2.68 |
Ferulic Acid | 1478.13 ± 24.89 b | 1540.91 ± 1.31 a | 1118.92 ± 7.20 c | y = 3.32x−4.30 | 0.9992 | 1.43 | 4.76 |
Gallic Acid | nd | 4.13 ± 0.10 a | 3.66 ± 0.07 b | y = 4.82x−26.48 | 0.9988 | 1.46 | 4.88 |
Hesperidin | 63.47 ± 3.16 c | 2389.83 ± 16.55 a | 158.20 ± 0.13 b | y = 5.98x+0.42 | 0.9993 | 1.73 | 5.77 |
Hyperoside | 117.67 ± 0.07 c | 956.75 ± 3.28 a | 139.13 ± 4.04 b | y = 16.32x−1.26 | 0.9998 | 0.99 | 3.31 |
Kaempferol | nd | nd | 3.17 ± 0.36 | y = 0.82x−3.06 | 0.9959 | 3.30 | 10.99 |
Luteolin | 5347.32 ± 54.96 a | 5339.91 ± 72.76 a | 780.53 ± 32.25 b | y = 8.96x+26.80 | 0.9992 | 1.34 | 4.46 |
Luteolin 7-glucoside | 270.77 ± 3.42 b | 1281.14 ± 39.03 a | 9.80 ± 0.66 c | y = 45.25x+156.48 | 0.9996 | 0.45 | 1.51 |
p-Coumaric Acid | 97.06 ± 1.72 c | 109.55 ± 0.73 b | 174.73 ± 2.53 a | y = 17.51x+53.73 | 0.9997 | 1.93 | 6.44 |
Pinoresinol | 262.78 ± 0.40 a | 79.11 ± 0.85 c | 107.54 ± 0.52 b | y = 0.80x−2.69 | 0.9966 | 3.94 | 13.12 |
Protocatechuic Acid | 74.35 ± 1.88 c | 175.75 ± 1.86 b | 378.73 ± 1.26 a | y = 5.65x−9.99 | 0.9990 | 1.17 | 3.88 |
Pyrocatechol | nd | nd | nd | y = 0.11x−0.52 | 0.9916 | 9.62 | 32.08 |
Quercetin | nd | 12.82 ± 0.20 b | 57.12 ± 0.70 a | y = 14.68x−18.25 | 0.9997 | 1.23 | 4.10 |
Rosmarinic Acid | 29.39 ± 1.49 c | 524.65 ± 14.24 b | 2074.40 ± 3.55 a | y = 9.82x−17.98 | 0.9989 | 0.57 | 1.89 |
Sinapic Acid | 449.82 ± 15.76 a | 35.79 ± 0.30 b | 23.75 ± 0.77 b | y = 2.09x−6.79 | 0.9974 | 2.64 | 8.78 |
Syringic Acid | 76.05 ± 3.45 c | 103.67 ± 2.51 b | 157.88 ± 2.09 a | y = 0.74x−1.54 | 0.9975 | 3.75 | 12.50 |
Taxifolin | nd | nd | 0.95 ± 0.32 | y = 12.32x+9.98 | 0.9993 | 1.82 | 6.05 |
Vanillic Acid | 694.01 ± 64.38 a | 735.80 ± 24.67 a | 476.23 ± 9.98 b | y = 0.49x−1.61 | 0.9968 | 2.56 | 8.54 |
Vanillin | 31.36 ± 1.39 a | 15.89 ± 0.29 b | nd | y = 2.02x+135.49 | 0.9926 | 15.23 | 50.77 |
Verbascoside | 41.47 ± 12.61 a | 4.57 ± 0.31 b | 41.99 ± 0.66 a | y = 8.59x−28.05 | 0.9988 | 0.82 | 2.75 |
Assays | ZTT-EtOAc | ZTT-MeOH | ZTT-W | Trolox | EDTA |
---|---|---|---|---|---|
Inhibition Concentration (IC50: mg/mL) | |||||
DPPH Radical Scavenging | 15.75 ± 0.66 c | 5.74 ± 0.08 b | 7.02 ± 0.23 b | 0.25 ± 0.01 a | - |
ABTS Radical Scavenging | 6.30 ± 0.03 d | 2.74 ± 0.10 c | 2.39 ± 0.10 b | 0.26 ± 0.01 a | - |
Phosphomolybdenum | 2.60 ± 0.03 c | 1.84 ± 0.08 b | 3.80 ± 0.17 d | 1.15 ± 0.01 a | - |
CUPRAC Reducing Power | 2.39 ± 0.10 b | 2.24 ± 0.11 b | 2.80 ± 0.02 c | 0.31 ± 0.02 a | - |
FRAP Reducing Power | 3.41 ± 0.28 c | 1.42 ± 0.04 b | 1.71 ± 0.02 b | 0.1 ± 0.01 a | - |
Ferrous Ion Chelating | 51.40 ± 1.32 c | 3.77 ± 0.09 b | 1.04 ± 0.01 b | - | 0.034 ± 0.003 a |
Antioxidant Activity | |||||
DPPH Radical Scavenging (mg TE/g extract) | 15.01 ± 0.68 c | 42.15 ± 0.6 1a | 33.99 ± 1.21 b | - | - |
ABTS Radical Scavenging (mg TE/g extract) | 42.06 ± 0.22 c | 97.01 ± 3.45 b | 111.94 ± 4.74 a | - | - |
Phosphomolybdenum (mg TE/g extract) | 446.22 ± 4.94 b | 630.08 ± 28.80 a | 304.30 ± 13.99 c | - | - |
CUPRAC Reducing Power (mg TE/g extract) | 131.89 ± 5.95 a | 134.66 ± 7.00 a | 105.47 ± 0.70 b | - | - |
FRAP Reducing Power (mg TE/g extract) | 30.79 ± 2.55 c | 73.62 ± 1.85 a | 61.27 ± 0.67 b | - | - |
Ferrous Ion Chelating (mg EDTAE/g extract) | 1.03 ± 0.04 c | 18.53 ± 0.47 b | 69.31 ± 0.18 a | - | - |
Assays | ZTT-EtOAc | ZTT-MeOH | ZTT-W | Kojic acid | Acarbose |
---|---|---|---|---|---|
Inhibition Concentration (IC50: mg/mL) | |||||
Tyrosinase Inhibition | 1.37 ± 0.07 b | 1.46 ± 0.06 b | 2.29 ± 0.13 c | 0.37 ± 0.02 a | - |
α-Amylase Inhibition | 1.82 ± 0.08 ab | 2.69 ± 0.14 b | 62.56 ± 0.56 c | - | 1.21 ± 0.07 a |
Enzyme inhibition activity | |||||
Tyrosinase Inhibition (mg KAE/g extract) | 262.76 ± 13.82 a | 246.27 ± 9.75 a | 156.88 ± 8.88 b | - | - |
α-Amylase Inhibition (mg ACE/g extract) | 672.87 ± 28.68 a | 452.44 ± 23.81 b | 16.03 ± 0.18 c | - | - |
Assays and Compounds | Tyrosinase | α-Amylase | CUPRAC | FRAP | ABTS | DPPH | Phosphomolybdenum | Ferrous Ion Chelating |
---|---|---|---|---|---|---|---|---|
α-Amylase | 0.982 | 1 | ||||||
CUPRAC | 0.973 | 0.912 | 1 | |||||
FRAP | –0.376 | –0.544 | –0.153 | 1 | ||||
ABTS | –0.766 | –0.874 | –0.599 | 0.883 | 1 | |||
DPPH | –0.363 | –0.533 | –0.14 | 0.999 z | 0.877 | 1 | ||
Phosphomolybdenum | 0.736 | 0.595 | 0.872 | 0.350 | –0.13 | 0.363 | 1 | |
Ferrous Ion Chelating | –0.995 | –0.996 | –0.944 | 0.470 | 0.829 | 0.458 | –0.662 | 1 |
Total Flavonoid | 0.751 | 0.612 | 0.883 | 0.330 | –0.152 | 0.342 | 0.999 y | –0.679 |
Total Phenolic | 0.973 | 0.999 y | 0.895 | –0.578 | –0.893 | –0.567 | 0.562 | –0.992 |
Caffeic Acid | –0.996 | –0.962 | –0.989 | 0.295 | 0.709 | 0.282 | –0.791 | 0.982 |
Vanillic Acid | 0.957 | 0.884 | 0.988 | –0.09 | –0.543 | –0.091 | 0.901 | –0.919 |
Chlorogenic Acid | –0.994 | –0.956 | –0.992 | 0.273 | 0.693 | 0.260 | –0.805 | 0.978 |
Sinapic Acid | 0.639 | 0.774 | 0.446 | –0.953 | –0.984 | –0.949 | –0.049 | –0.716 |
Ferulic Acid | 0.960 | 0.890 | 0.999 y | –0.101 | –0.556 | –0.088 | 0.896 | –0.926 |
Luteolin 7-glucoside | 0.543 | 0.374 | 0.721 | 0.574 | 0.124 | 0.585 | 0.968 | –0.453 |
Hesperidin | 0.336 | 0.151 | 0.543 | 0.747 | 0.348 | 0.756 | 0.884 | –0.236 |
Hyperoside | 0.348 | 0.164 | 0.554 | 0.738 | 0.335 | 0.747 | 0.891 | –0.249 |
Rosmarinic Acid | –0.996 | –0.995 | –0.949 | 0.456 | 0.820 | 0.444 | –0.673 | 0.999 z |
Luteolin | 0.990 | 0.945 | 0.996 | –0.239 | –0.666 | –0.226 | 0.826 | –0.969 |
Apigenin | 0.999 z | 0.981 | 0.975 | –0.369 | –0.762 | –0.357 | 0.741 | –0.994 |
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Tomczyk, M.; Ceylan, O.; Locatelli, M.; Tartaglia, A.; Ferrone, V.; Sarikurkcu, C. Ziziphora taurica subsp. taurica: Analytical Characterization and Biological Activities. Biomolecules 2019, 9, 367. https://doi.org/10.3390/biom9080367
Tomczyk M, Ceylan O, Locatelli M, Tartaglia A, Ferrone V, Sarikurkcu C. Ziziphora taurica subsp. taurica: Analytical Characterization and Biological Activities. Biomolecules. 2019; 9(8):367. https://doi.org/10.3390/biom9080367
Chicago/Turabian StyleTomczyk, Michał, Olcay Ceylan, Marcello Locatelli, Angela Tartaglia, Vincenzo Ferrone, and Cengiz Sarikurkcu. 2019. "Ziziphora taurica subsp. taurica: Analytical Characterization and Biological Activities" Biomolecules 9, no. 8: 367. https://doi.org/10.3390/biom9080367