Abstract
The effect of 8,8-dimethyl-3-[(R-phenyl)amino]-1,4,5(8H)-naphthalentrione derivatives (compounds 1–13) on the mycelial growth of Botrytis cinerea 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 3, 4, 5 and 7), methyl (compounds 8 and 9), methoxyl (compounds 10 and 11), or ethoxy-carbonyl groups (compound 12) presented higher antifungal activity than compound 1, which had an unsubstituted aromatic ring. In addition, compounds with halogens in the ortho position, such as compounds 2 and 6, and a substitution with an acetyl group in the para position (compound 13) were less active. The role of the ABC efflux pump Bctr B-type as a defense mechanism of B. cinerea against these naphthalentrione derivatives was analyzed. This pump could be involved in the detoxification of compounds 2, 6, and 13. On the contrary, this mechanism would not participate in the detoxification of compounds 1, 7, 9 and 12. Finally, the biotransformation of compound 7 by B. cinerea was studied. A mixture of two biotransformed products was obtained. One of them was compound 7A, which is reduced at C1 and C4, compared to compound 7. The other product of biotransformation, 7B, is oxidized at C7.
Highlights
Botrytis cinerea is a common phytopathogenic fungus that causes serious pre- and post-harvest diseases in at least 200 plant species
The effect of 13 synthetic compounds on the mycelial growth of B05.10 isolate from B. cinerea in solid media was determined at 72 h of incubation and it was expressed in IC50
It can be concluded that the antifungal effect against B. cinerea would be favored when the aromatic ring presents substitutions in the para position, except for the acetyl group substitution
Summary
Botrytis cinerea is a common phytopathogenic fungus that causes serious pre- and post-harvest diseases in at least 200 plant species. The broad host range of B. cinerea results in great economic losses during growth and during storage and transport [1,2] This fungus is able to defend itself against toxic compounds through drug efflux transporters [3]. It has been reported that this fungus can biotransform various families of compounds, such as steroids, flavonoids, monoterpenes, and sesquiterpenes, among others These modifications are carried out by enzymes, such as hydroxylases, oxygenases, or reductases, producing generally hydroxylations, epoxidations, oxidations, or reductions of the molecules [9,10,11,12,13].
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