Laboratorio de Micología, Facultad de Biología y Química, Universidad de Santiago de Chile, Alameda 3363, Estación Central, Santiago 9160000, Chile.
Núcleo de Química y Bioquímica, Facultad de Estudios Interdisciplinarios, Universidad Mayor, Camino La Pirámide 5750, Huechuraba, Santiago 8580000, Chile.
Molecules. 2019 Feb 2;24(3):544. doi: 10.3390/molecules24030544.
The effect of 8,8-dimethyl-3-[(-phenyl)amino]-1,4,5(8)-naphthalentrione derivatives (compounds ⁻) on the mycelial growth of was evaluated. The fungitoxic effect depended on the substituent and its position in the aromatic ring. Compounds substituted with halogens in meta and/or para positions (compounds , , and ), methyl (compounds and ), methoxyl (compounds and ), or ethoxy-carbonyl groups (compound ) presented higher antifungal activity than compound , which had an unsubstituted aromatic ring. In addition, compounds with halogens in the ortho position, such as compounds and , and a substitution with an acetyl group in the para position (compound ) were less active. The role of the ABC efflux pump Bctr B-type as a defense mechanism of against these naphthalentrione derivatives was analyzed. This pump could be involved in the detoxification of compounds , , and . On the contrary, this mechanism would not participate in the detoxification of compounds , , and . Finally, the biotransformation of compound by was studied. A mixture of two biotransformed products was obtained. One of them was compound , which is reduced at C1 and C4, compared to compound . The other product of biotransformation, 7B, is oxidized at C7.
评估了 8,8-二甲基-3-[[(-苯基)氨基]-1,4,5(8)-萘三酮衍生物（化合物 ⁻）对菌丝生长的影响。抑菌效果取决于取代基及其在芳环上的位置。在间位和/或对位带有卤素（化合物 、 、 和 ）、甲基（化合物 、 和 ）、甲氧基（化合物 、 和 ）或乙氧羰基（化合物 ）取代的化合物比具有未取代芳环的化合物 具有更高的抗真菌活性。此外，邻位带有卤素的化合物，如化合物 和 ，以及对位带有乙酰基取代的化合物 （化合物 ）活性较低。分析了 ABC 外排泵 Bctr B 型作为 对这些萘三酮衍生物的防御机制的作用。该泵可能参与化合物 、 和 的解毒。相反，这种机制不会参与化合物 、 、 和 的解毒。最后，研究了化合物 被 生物转化。得到了两种生物转化产物的混合物。其中一种是化合物 ，与化合物 相比，在 C1 和 C4 处被还原。生物转化的另一种产物 7B 在 C7 处被氧化。
