In Vitro Antifungal Activity of New and Known Geranylated Phenols against Phytophthora cinnamomi Rands
Abstract
:1. Introduction
2. Results and Discussion
2.1. Antifungal Activity of Linear Geranylated Phenols/Methoxyphenols Derivatives against P. cinnamomi In Vitro
2.2. Chemistry
3. Materials and Methods
3.1. Antifungal Activity of Linear Geranylated Phenols/Methoxyphenols against Phytophthora Cinnamomi In Vitro
3.2. General Chemistry
3.3. Synthesis
3.3.1. (E)-3-(3,7-Dimethylocta-2,6-Dienyl)Benzene-1,2-Diol (4); (E)-4-(3,7-Dimethylocta-2,6-Dienyl)Benzene-1,2-Diol (5); 4,5-Bis((E)-3,7-Dimethylocta-2,6-Dienyl)Benzene-1,2-Diol (24)
3.3.2. (E)-4-(3,7-Dimethylocta-2,6-Dienyl)Benzene-1,3-Diol (6); 2,4-Bis((E)-3,7-Dimethylocta-2,6-Dienyl)Benzene-1,3-Diol (25); 4,6-Bis((E)-3,7-Dimethylocta-2,6-Dienyl)Benzene-1,3-Diol (26)
3.3.3. (E)-2-(3,7-Dimethylocta-2,6-Dienyl)-6-Methoxyphenol (10); (E)-3-(3,7-Dimethylocta-2,6-Dienyl)-2-Methoxyphenol (11); (E)-5-(3,7-Dimethylocta-2,6-Dienyl)-2-Methoxyphenol (12); 4,5-Bis((E)-3,7-Dimethylocta-2,6-Dienyl)-2-Methoxyphenol (29)
3.3.4. (E)-5-(3,7-Dimethylocta-2,6-Dienyl)Benzene-1,2,4-Triol (14)
3.3.5. (E)-6-(3,7-Dimethylocta-2,6-Dienyl)-2,3-Dimethoxyphenol (17); (E)-4-(3,7-Dimethylocta-2,6-Dienyl)-2,3-Dimethoxyphenol (18)
3.3.6. (E)-2-(3,7-Dimethylocta-2,6-Dienyl)-3,4,5-Trimethoxyphenol (21); 2,6-Bis((E)-3,7-Dimethylocta-2,6-Dienyl)-3,4,5-Trimetoxyphenol (32)
4. Conclusions
Supplementary Materials
Author Contributions
Acknowledgments
Conflicts of Interest
References
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Linear Geranylated Phenols/Methoxyphenols Derivatives | Percentage of Inhibition* on In Vitro Mycelial Growth of P. cinnamomi (%) | ||
---|---|---|---|
50 mg/L | 150 mg/L | 250 mg/L | |
1 | 87 ± 0.0 | 100 ± 0.0 * | 100 ± 0.0 * |
2 | 53 ± 8.8 | 78 ± 3.8 | 96 ± 2.5 * |
3 | 86 ± 1.3 | 95 ± 2.5 * | 96 ± 2.5 * |
4 | 56 ± 2.6 | 81 ± 10.7 | 85 ± 7.5 |
5 | 56 ± 2.5 | 73 ± 6.3 | 84 ± 1.3 |
6 | 82 ± 5.5 | 96 ± 2.5 * | 98 ± 0.0 * |
7 | 62 ± 3.3 | 73 ± 2.5 | 78 ± 3.8 |
8 | 77 ± 5.0 | 72 ± 3.0 | 75 ± 5.0 |
9 | 23 ± 2.5 | 45 ± 2.5 | 56 ± 2.5 |
10 | 0.0 ± 0.0 | 0.0 ± 0.0 | 0.0 ± 0.0 |
11 | 12 ± 1.3 | 12 ± 1.3 | 20 ± 2.5 |
13 | 45±2.5 | 68 ± 1.3 | 70 ± 1.3 |
14 | 15 ± 6.3 | 50 ± 5.8 | 73 ± 8.2 |
15 | 26 ± 3.8 | 44 ± 0.0 | 55 ± 1.3 |
16 | 39 ± 0.0 | 47 ± 1.3 | 55 ± 1.3 |
17 | 36 ± 2.5 | 44 ± 0.0 | 59 ± 3.8 |
18 | 22 ± 0.0 | 44 ± 0.0 | 46 ± 2.5 |
19 | 32 ± 1.3 | 30 ± 3.8 | 26 ± 4.5 |
20 | 39 ± 0.0 | 43 ± 1.3 | 51 ± 6.3 |
21 | 29 ± 3.3 | 31 ± 2.5 | 33 ± 0.0 |
22 | 22 ± 0.0 | 17 ± 0.0 | 17 ± 0.0 |
23 | 33 ± 0.0 | 25 ± 1.3 | 21 ± 1.3 |
25 | 28 ± 1.3 | 23 ± 1.3 | 00 ± 0.0 |
27 | 8 ± 7.0 | 27 ± 2.5 | 36 ± 3.3 |
28 | 0 ± 0.0 | 22 ± 0.0 | 23 ± 1.3 |
29 | 2 ± 2.2 | 9 ± 0.0 | 1 ± 1.3 |
30 | 0 ± 0.0 | 0 ± 0.0 | 0 ± 0.0 |
31 | 22 ± 0.0 | 21 ± 1.3 | 14 ± 3.3 |
32 | 2 ± 2.5 | 2 ± 2.5 | 3 ± 2.5 |
C+ | 99 ± 2.1 | 99 ± 1.1 | 100 ± 1.3 |
C− | 00 ± 0.0 | 00 ± 0.0 | 00 ± 0.0 |
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Chavez, M.I.; Soto, M.; Cimino, F.A.; Olea, A.F.; Espinoza, L.; Díaz, K.; Taborga, L. In Vitro Antifungal Activity of New and Known Geranylated Phenols against Phytophthora cinnamomi Rands. Int. J. Mol. Sci. 2018, 19, 1601. https://doi.org/10.3390/ijms19061601
Chavez MI, Soto M, Cimino FA, Olea AF, Espinoza L, Díaz K, Taborga L. In Vitro Antifungal Activity of New and Known Geranylated Phenols against Phytophthora cinnamomi Rands. International Journal of Molecular Sciences. 2018; 19(6):1601. https://doi.org/10.3390/ijms19061601
Chicago/Turabian StyleChavez, María I., Mauricio Soto, Franco A. Cimino, Andrés F. Olea, Luis Espinoza, Katy Díaz, and Lautaro Taborga. 2018. "In Vitro Antifungal Activity of New and Known Geranylated Phenols against Phytophthora cinnamomi Rands" International Journal of Molecular Sciences 19, no. 6: 1601. https://doi.org/10.3390/ijms19061601