Biological Activity of Hybrid Molecules Based on Major Constituents of Cinnammomun verum and Thymus vulgaris Essential Oils
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals and Reagents
2.2. Chemical Synthesis of the Hybrid Molecules
2.3. Enzymatic Synthesis of the Hybrid Molecules
2.4. GC-MS Analysis
2.5. NMR Analysis
2.6. In Vitro Antifungal Activity Assay
2.6.1. Mycelial Growth Inhibition
2.6.2. Spore Germination Inhibition
2.7. Brine Shrimp Lethality Bioassay
2.8. Statistical Analysis
3. Results
3.1. Chemical Synthesis of Hybrid Molecules Based on Major Constituents of Thymus vulgaris and Cinnamomun verum EOs
3.2. Enzymatic Synthesis of Hybrid Molecules Based on Major Constituents of Thymus vulgaris and Cinnamomun verum EOs
3.3. Biological Activity
3.3.1. Mycelial Growth Inhibition
3.3.2. Spore Germination Inhibition
3.3.3. Cytotoxic Activity
4. Discussion
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Hybrid | Mycelial Growth Inhibition (MGI) | ||||||||
---|---|---|---|---|---|---|---|---|---|
C. gloeosporioides | F. oxysporum | A. niger | |||||||
Concentration (w/v) | Concentration (w/v) | Concentration (w/v) | |||||||
0.5% | 0.25% | 0.125% | 0.5% | 0.25% | 0.125% | 0.5% | 0.25% | 0.125% | |
(1) | 94.76 ± 0.14 * | 76.83 ± 0.12 * | 65.56 ± 0.13 * | 75.04 ± 0.14 * | 63.20 ± 0.11 * | 48.23 ± 0.07 * | 65.13 ± 0.02 * | 62.66 ± 0.05 * | 57.19 ± 0.08 * |
(2) | 94.74 ± 0.06 * | 86.77 ± 0.04 * | 76.22 ± 0.09 * | 69.74 ± 0.06 * | 54.96 ± 0.08 * | 29.48 ± 0.15 * | 60.11 ± 0.02 * | 58.97 ± 0.04 * | 51.10 ± 0. 07 * |
(3) | 91.22 ± 0.08 * | 88.24 ± 0.11 * | 78.33 ± 0.10 * | 83.09 ± 0.02 * | 60.07 ± 0.10 * | 51.48 ± 0.06 * | 59.56 ± 0.03 * | 57.27 ± 0.07 * | 50.61 ± 0.03 * |
(4) | 100 ± 0.00 * | 83.61 ± 0.04 * | 73.82 ± 0.09 * | 70.07 ± 0.18 * | 61.62 ± 0.09 * | 32.87 ± 0.12 * | 18.34 ± 0.05 * | 12.28 ± 0.08 * | 3.31 ± 0.07 * |
(5) | 96.41 ± 0.03 * | 80.67 ± 0.18 * | 70.07 ± 0.09 * | 86.82 ± 0.10 * | 51.63 ± 0.07 * | 30.81 ± 0.04 * | 28.37 ± 0.06 * | 23.10 ± 0.02 * | 20.34 ± 0.05 * |
(6) | 100 ± 0.00 * | 70.51 ± 0.04 * | 64.23 ± 0.18 * | 82.77 ± 0.08 * | 64.23 ± 0.17 * | 20.56 ± 0.05 * | 27.92 ± 0.08 * | 12.95 ± 0.11 * | 11.19 ± 0.03 * |
Hybrid | Spore Germination Inhibition (SGI) | ||||||||
---|---|---|---|---|---|---|---|---|---|
C. gloeosporioides | F. oxysporum | A. niger | |||||||
Concentration (w/v) | Concentration (w/v) | Concentration (w/v) | |||||||
0.5% | 0.25% | 0.125% | 0.5% | 0.25% | 0.125% | 0.5% | 0.25% | 0.125% | |
(1) | 34.40 ± 2.98 * | 13.89 ± 1.84 * | 11.24 ± 2.29 | 16.82 ± 0.25 * | 11.84 ± 2.57 | 0.00 ± 0.00 | 13.68 ± 2.54 * | 10.24± 1.87 | 0.00 ± 0.00 |
(2) | 27.32 ± 1.86 * | 2.57 ± 0.05 | 1.19 ± 0.76 | 5.92 ± 1.12 | 0.00 ± 0.00 | 0.00 ± 0.00 | 23.62 ± 3.05 * | 10.91 ± 3.04 | 6.49 ± 1.12 |
(3) | 11.94 ± 0.43 * | 8.09 ± 0.30 | 1.64 ± 0.26 | 37.69 ± 6.3 * | 24.92 ± 3.5 * | 14.64 ± 0.75 * | 0.00 ± 0.00 | 0.00 ± 0.00 | 0.00 ± 0.00 |
(4) | 7.00 ± 1.89 | 5.60 ± 1.42 | 0.00 ± 0.00 | 16.52 ± 4.75 * | 12.86 ± 1.23 * | 0.00 ± 0.00 | 0.00 ± 0.00 | 0.00 ± 0.00 | 0.00 ± 0.00 |
(5) | 4.68 ± 1.49 | 4.50 ± 0.93 | 0.00 ± 0.00 | 0.16 ± 0.11 | 0.00 ± 0.00 | 0.00 ± 0.00 | 0.00 ± 0.00 | 0.00 ± 0.00 | 0.00 ± 0.00 |
(6) | 10.90 ± 5.3 | 2.72 ± 0.71 | 2.20 ± 0.87 | 0.00 ± 0.00 | 0.00 ± 0.00 | 0.00 ± 0.00 | 0.00 ± 0.00 | 0.00 ± 0.00 | 0.00 ± 0.00 |
Hybrid | Concentrations (µg/mL) | % Mortality | LC50 (µg/mL) |
---|---|---|---|
(1) | 600 | 100 ± 0.00 * | 50.39 |
300 | 100 ± 0.00 * | ||
150 | 96.67 ± 5.77 * | ||
100 | 76.67 ± 15.27 * | ||
75 | 70.00 ± 10.00 * | ||
50 | 46.67 ± 15.27 * | ||
25 | 43.33 ± 10.00 * | ||
10 | 33.33 ± 5.77 * | ||
1 | 13.33 ± 5.77 * | ||
(2) | 600 | 96.67 ± 5.77 * | 68.22 |
300 | 96.67 ± 5.77 * | ||
150 | 83.33 ± 15.27 * | ||
100 | 63.33 ± 15.27 * | ||
75 | 60.00 ± 10.00 * | ||
50 | 50.22 ± 10.00 * | ||
25 | 30.68 ± 10.00 * | ||
10 | 22.34 ± 0.00 * | ||
1 | 10.12 ± 10.00 * | ||
(3) | 600 | 66.67 ± 5.77 * | 418.56 |
300 | 26.67 ± 5.77 * | ||
150 | 16.98 ± 5.77 * | ||
100 | 16.42 ± 5.77 * | ||
75 | 15.38 ± 0.00 * | ||
50 | 12.11 ± 5.77 * | ||
25 | 10.8 ± 0.00 * | ||
10 | 8.7 ± 0.00 * | ||
1 | 5.6 ± 0.00 * | ||
(4) | 600 | 100 ± 0.00 * | 64.41 |
300 | 93.30 ± 5.77 * | ||
150 | 86.67 ± 5.77 * | ||
100 | 63.33 ± 5.77 * | ||
75 | 60.00 ± 5.77 * | ||
50 | 33.33 ± 5.77 * | ||
25 | 36.67 ± 11.33 * | ||
10 | 33.33 ± 5.77 * | ||
1 | 20.00 ± 0.00 * | ||
(5) | 600 | 80.00 ± 17.32 * | 71.95 |
300 | 70.00 ± 10.00 * | ||
150 | 70.00 ± 10.00 * | ||
100 | 63.33 ± 15.27 * | ||
75 | 54.85 ± 5.77 * | ||
50 | 40.00 ± 17.32 * | ||
25 | 33.33 ± 5.77 * | ||
10 | 36.67 ± 5.77 * | ||
1 | 23.33 ± 0.00 * | ||
(6) | 600 | 66.67 ± 15.27 * | 465.87 |
300 | 33.33 ± 5.77 * | ||
150 | 30.00 ± 10.00 * | ||
100 | 30.00 ± 0.00 * | ||
75 | 23.33 ± 5.77 * | ||
50 | 21.48± 5.77 * | ||
25 | 16.67 ± 0.00 * | ||
10 | 16.00± 5.77 * | ||
1 | 15.00 ± 0.00 * |
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Valverde Sancho, J.; Carreño Amate, C.; Caparrós Pérez, M.d.M.; Santana Méridas, O.; Julio, L.F. Biological Activity of Hybrid Molecules Based on Major Constituents of Cinnammomun verum and Thymus vulgaris Essential Oils. Life 2023, 13, 499. https://doi.org/10.3390/life13020499
Valverde Sancho J, Carreño Amate C, Caparrós Pérez MdM, Santana Méridas O, Julio LF. Biological Activity of Hybrid Molecules Based on Major Constituents of Cinnammomun verum and Thymus vulgaris Essential Oils. Life. 2023; 13(2):499. https://doi.org/10.3390/life13020499
Chicago/Turabian StyleValverde Sancho, Juan, Cristina Carreño Amate, María del Mar Caparrós Pérez, Omar Santana Méridas, and Luis F. Julio. 2023. "Biological Activity of Hybrid Molecules Based on Major Constituents of Cinnammomun verum and Thymus vulgaris Essential Oils" Life 13, no. 2: 499. https://doi.org/10.3390/life13020499