In Vitro Antifungal Activity of Sanguinarine and Chelerythrine Derivatives against Phytopathogenic Fungi
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Antifungal Activity
2.2.1. Screening of Antifungal Activity in Vitro
Compd. | Seven Tested Phytopathogenic Fungi * | ||||||
---|---|---|---|---|---|---|---|
C.L. | V.M. | F.S. | F.O.N. | F.O.V. | P. O. | A.A. | |
S | 78.6 ± 3.4DE ** | 84.8 ± 0.8BC | 81.4 ± 1.0BC | 72.1 ± 3.1E | 82.0 ± 2.2D | 60.4 ± 2.1D | 71.2 ± 0.0C |
S1 | 80.8 ± 2.0BCDE | 88.1 ± 0.4AB | 83.8 ± 2.6BC | 86.6 ± 1.5C | 84.0 ± 0.0CD | 70.8 ± 2.1C | 74.6 ± 0.9C |
S2 | 87.5 ± 2.8A | 85.8 ± 5.9BC | 85.4 ± 2.6B | 69.7 ± 1.7E | 85.6 ± 1.6CD | 70.1 ± 3.2C | 70.0 ± 2.3C |
S3 | 86.1 ± 0.8AB | 93.2 ± 0.6A | 86.9 ± 4.6AB | 87.6 ± 2.3C | 87.2 ± 1.6C | 69.4 ± 1.2C | 73.6 ± 0.9C |
S4 | 78.1 ± 1.5DE | 84.6 ± 1.8BC | 82.0 ± 2.1BC | 79.6 ± 5.4D | 84.5 ± 1.0CD | 61.1 ± 1.2D | 64.9 ± 1.5D |
S5 | 79.7 ± 0.8CDE | 80.1 ± 0.4C | 73.3 ± 0.0D | 63.2 ± 0.0F | 71.6 ± 0.7E | 47.0 ± 0.6E | 44.9 ± 1.6E |
S6 | 19.1 ± 2.0HI | −4.0 ± 3.5FG | −0.1 ± 3.2F | −0.5 ± 0.9K | −4.4 ± 0.9J | 9.7 ± 1.2HI | 16.2 ± 1.5H |
S7 | 33.0 ± 1.3F | −8.3 ± 1.7H | 7.5 ± 1.9E | 2.0 ± 3.4JK | −0.1 ± 1.8HI | 20.8 ± 0.0G | 21.2 ± 0.9G |
S8 | 18.0 ± 1.3I | 3.4 ± 0.7DE | 6.3 ± 0.7E | 0.5 ± 0.9JK | 2.6 ± 3.9H | 5.8 ± 1.2IJ | 11.0 ± 1.5I |
C | 81.5 ± 2.2BCDE | 88.5 ± 2.0AB | 87.3 ± 0.2AB | 85.6 ± 0.9C | 94.2 ± 0.0B | 74.3 ± 1.2BC | 83.7 ± 1.8B |
C1 | 79.9 ± 3.5CDE | 93.0 ± 1.7A | 92.4 ± 0.4A | 94.0 ± 0.0B | 100.0 ± 0.0A | 77.1 ± 2.1AB | 85.8 ± 0.9AB |
C2 | 76.3 ± 0.8E | 86.9 ± 0.4AB | 83.4 ± 0.2BC | 100.0 ± 0.0A | 95.7 ± 3.7AB | 79.9 ± 1.2AB | 86.8 ± 0.9AB |
C3 | 85.7 ± 5.1ABC | 89.8 ± 2.1AB | 86.4 ± 6.4AB | 94.0 ± 0.0B | 100.0 ± 0.0A | 81.9 ± 2.4A | 87.3 ± 0.9AB |
C4 | 82.6 ± 4.0ABCD | 83.5 ± 0.8BC | 82.2 ± 0.9BC | 90.5 ± 0.9BC | 92.0 ± 0.0B | 83.0 ± 0.6A | 88.8 ± 0.9A |
C5 | 80.8 ± 0.3BCDE | 84.4 ± 0.4BC | 78.7 ± 0.4CD | 40.2 ± 3.4G | 69.1 ± 1.1E | 48.4 ± 1.1E | 62.5 ± 0.8D |
C6 | 5.7 ± 3.4J | −1.4 ± 2.8EF | 8.6 ± 3.9E | 5.0 ± 0.9IJ | −3.3 ± 3.3IJ | 1.4 ± 2.4J | 5.5 ± 1.5J |
C7 | 18.0 ± 1.3I | 5.1 ± 6.9D | 10.5 ± 3.2E | 13.4 ± 0.0H | 12.7 ± 2.4F | 28.9 ± 5.9F | 47.9 ± 5.9E |
C8 | 24.0 ± 2.0GH | −5.2 ± 2.4FG | 10.5 ± 1.3E | 9.5 ± 4.8HI | 6.8 ± 0.9G | 11.9 ± 1.3H | 24.7 ± 1.8G |
TBZ *** | 27.1 ± 1.5G | 88.4 ± 0.8AB | 83.9 ± 3.5BC | 100.0 ± 0.0A | 100.0 ± 0.0A | 15.3 ± 6.7GH | 30.6 ± 4.0F |
2.2.2. Antifungal Toxicity
Fungus | Compd. | Toxicity regression equation * | R2 | EC50 value | CI 95% ** (µg/mL) | CA *** | |
---|---|---|---|---|---|---|---|
(µg/mL) | (µM) | ||||||
C.L. | S | y = 0.5758x − 0.3905 | 0.9628 | 35.20 | 76.6 | 35.13–35.27 | 16.4 |
S1 | y = 0.5452x − 0.2960 | 0.9848 | 28.84 | 79.4 | 28.81–28.85 | 18.9 | |
C | y = 0.3413x + 0.0944 | 0.9621 | 15.43 | 32.5 | 15.21–15.65 | 22.1 | |
C1 | y = 0.3635x + 0.0808 | 0.9914 | 14.23 | 37.5 | 14.18–14.28 | 25.5 | |
V.M. | S | y = 0.6317x − 0.3751 | 0.9901 | 24.28 | 52.9 | 24.24–24.32 | 26.0 |
S1 | y = 0.5275x − 0.2329 | 0.9860 | 24.51 | 67.5 | 23.97–25.05 | 21.5 | |
C | y = 0.6918x − 0.6038 | 0.9505 | 39.40 | 82.9 | 39.30–39.50 | 17.6 | |
C1 | y = 0.6420x − 0.4423 | 0.9904 | 29.36 | 77.4 | 29.34–29.38 | 21.9 | |
F.S. | S | y = 0.7415x − 0.6922 | 0.9717 | 40.53 | 88.3 | 40.46–40.60 | 18.3 |
S1 | y = 0.5949x − 0.4189 | 0.957 | 35.04 | 96.4 | 34.95–35.13 | 17.0 | |
C | y = 0.5005x − 0.2123 | 0.9600 | 26.50 | 55.8 | 26.41–26.59 | 18.9 | |
C1 | y = 0.5949x − 0.3540 | 0.9925 | 27.26 | 71.8 | 27.24–27.28 | 21.8 | |
F.O.N. | S | y = 0.5139x − 0.3676 | 0.9768 | 48.79 | 106.2 | 48.73–48.85 | 10.9 |
S1 | y = 0.5487x − 0.3317 | 0.9705 | 32.79 | 90.2 | 32.73–32.85 | 16.7 | |
C | y = 0.6186x − 0.4076 | 0.9891 | 29.32 | 61.7 | 29.30–29.34 | 21.1 | |
C1 | y = 0.6629x − 0.4624 | 0.9836 | 28.30 | 74.6 | 28.26–28.34 | 23.4 | |
F.O.V. | S | y = 0.6007x − 0.4137 | 0.9735 | 33.20 | 72.3 | 33.14–33.26 | 18.1 |
S1 | y = 0.6320x − 0.4735 | 0.9826 | 34.70 | 95.5 | 34.66–34.74 | 18.2 | |
C | y = 1.0309x − 1.2677 | 0.9600 | 51.84 | 109.1 | 51.80–51.88 | 19.9 | |
C1 | y = 0.6303x − 0.4308 | 0.9684 | 29.98 | 79.0 | 29.91–30.06 | 21.0 | |
P.O. | S | y = 0.3182x − 0.1386 | 0.9687 | 101.6 | 221.2 | 101.2–102.00 | 3.1 |
S1 | y = 0.4238x − 0.3413 | 0.9914 | 96.63 | 265.9 | 96.61-96.63 | 4.4 | |
C | y = 0.7447x − 0.7550 | 0.9727 | 48.44 | 101.9 | 48.41–48.47 | 15.4 | |
C1 | y = 0.7178x − 0.6779 | 0.9843 | 43.75 | 115.3 | 43.72–43.78 | 16.4 | |
A.A. | S | y = 0.7921x − 0.8663 | 0.9608 | 53.08 | 115.6 | 53.03–53.13 | 14.9 |
S1 | y = 0.5176x − 0.3453 | 0.9193 | 43.47 | 119.6 | 43.10–43.84 | 11.9 | |
C | y = 0.9270x − 1.0756 | 0.9572 | 50.08 | 105.4 | 50.03–50.13 | 18.5 | |
C1 | y = 0.6218x − 0.4104 | 0.9659 | 29.11 | 76.7 | 29.04–29.18 | 21.4 |
2.3. Structure-Activity Relationship
3. Experimental
3.1. General
3.2. Synthesis of S1–S8 and C1–C8
3.3. Screening of Antifungal Activity in Vitro
3.4. Toxicity Assays
3.5. Statistic Analysis
4. Conclusions
Acknowledgments
References
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Yang, X.-J.; Miao, F.; Yao, Y.; Cao, F.-J.; Yang, R.; Ma, Y.-N.; Qin, B.-F.; Zhou, L. In Vitro Antifungal Activity of Sanguinarine and Chelerythrine Derivatives against Phytopathogenic Fungi. Molecules 2012, 17, 13026-13035. https://doi.org/10.3390/molecules171113026
Yang X-J, Miao F, Yao Y, Cao F-J, Yang R, Ma Y-N, Qin B-F, Zhou L. In Vitro Antifungal Activity of Sanguinarine and Chelerythrine Derivatives against Phytopathogenic Fungi. Molecules. 2012; 17(11):13026-13035. https://doi.org/10.3390/molecules171113026
Chicago/Turabian StyleYang, Xin-Juan, Fang Miao, Yao Yao, Fang-Jun Cao, Rui Yang, Yan-Ni Ma, Bao-Fu Qin, and Le Zhou. 2012. "In Vitro Antifungal Activity of Sanguinarine and Chelerythrine Derivatives against Phytopathogenic Fungi" Molecules 17, no. 11: 13026-13035. https://doi.org/10.3390/molecules171113026