Design and Synthesis of Eugenol Derivatives Bearing a 1,2,3-Triazole Moiety for Papaya Protection against Colletotrichum gloeosporioides

A series of 19 novel eugenol derivatives containing a 1,2,3-triazole moiety was synthesized via a two-step process, with the key step being a copper­(I)-catalyzed azide–alkyne cycloaddition reaction. The compounds were assessed for their antifungal activities against Colletotrichum gloeosporioides,...

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Published in:Journal of agricultural and food chemistry 2024-05, Vol.72 (22), p.12459-12468
Main Authors: Almeida lima, Ângela Maria, Moreira, Luíza Carvalheira, Gazolla, Poliana Rodrigues, Oliveira, Mariana Belizario, Teixeira, Róbson Ricardo, Queiroz, Vagner Tebaldi, Rocha, Matheus Ricardo, Moraes, Willian Bucker, dos Santos, Nayara Araújo, Romão, Wanderson, Bezerra Morais, Pedro Alves, Oliveira, Osmair Vital de, Júnior, Waldir Cintra de Jesus, Barbosa, Luiz C. A., Nascimento, Cláudia Jorge, Junker, Jochen, Costa, Adilson Vidal
Format: Article
Language:English
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Agricultural and Environmental Chemistry
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Summary:A series of 19 novel eugenol derivatives containing a 1,2,3-triazole moiety was synthesized via a two-step process, with the key step being a copper­(I)-catalyzed azide–alkyne cycloaddition reaction. The compounds were assessed for their antifungal activities against Colletotrichum gloeosporioides, the causative agent of papaya anthracnose. Triazoles 2k, 2m, 2l, and 2n, at 100 ppm, were the most effective, reducing mycelial growth by 88.3, 85.5, 82.4, and 81.4%, respectively. Molecular docking calculations allowed us to elucidate the binding mode of these derivatives in the catalytic pocket of C. gloeosporioides CYP51. The best-docked compounds bind closely to the heme cofactor and within the channel access of the lanosterol (LAN) substrate, with crucial interactions involving residues Tyr102, Ile355, Met485, and Phe486. From such studies, the antifungal activity is likely attributed to the prevention of substrate LAN entry by the 1,2,3-triazole derivatives. The triazoles derived from natural eugenol represent a novel lead in the search for environmentally safe agents for controlling C. gloeosporioides.
ISSN:0021-8561
1520-5118
1520-5118
DOI:10.1021/acs.jafc.4c00440