Design and synthesis of eugenol derivatives bearing a 1,2,3- triazole moiety for papaya protection against colletotrichum gloeosporioides

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dc.creatorÂngela Maria Almeida Lima
dc.creatorLuíza Carvalheira Moreira
dc.creatorPoliana Rodrigues Gazolla
dc.creatorMariana Belizario Oliveira
dc.creatorRóbson Ricardo Teixeira
dc.creatorVagner Tebaldi Queiroz
dc.creatorMatheus Ricardo Rocha
dc.creatorWillian Bucker Moraes
dc.creatorNayara Araujo dos Santos
dc.creatorWanderson Romão
dc.creatorValdemar Lacerda Jr.
dc.creatorPedro Alves Bezerra Morais
dc.creatorOsmair Vital de Oliveira
dc.creatorWaldir Cintra de Jesus Junior
dc.creatorLuiz Claudio de Almeida Barbosa
dc.creatorCláudia Jorge Nascimento
dc.creatorJochen Junker
dc.creatorAdilson Vidal Costa
dc.date.accessioned2026-03-04T18:09:22Z
dc.date.issued2024-05-21
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipOutra Agência
dc.identifier.doihttps://doi.org/10.1021/acs.jafc.4c00440
dc.identifier.issn0021-8561
dc.identifier.urihttps://hdl.handle.net/1843/1931
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofJournal of Agricultural and Food Chemistry
dc.rightsAcesso aberto
dc.rightsCC0 1.0 Universalen
dc.rights.urihttp://creativecommons.org/publicdomain/zero/1.0/
dc.subjectEugenol
dc.subject1,2,3- triazóis
dc.subjectFungicidas
dc.subjectMetabólitos
dc.subjectAntracnose
dc.subject.otherColletotrichum gloeosporioide
dc.subject.otherFungicide activity
dc.subject.other1,2,3-triazole
dc.subject.otherPapaya
dc.subject.otherMolecular docking
dc.subject.otherEugenol
dc.titleDesign and synthesis of eugenol derivatives bearing a 1,2,3- triazole moiety for papaya protection against colletotrichum gloeosporioides
dc.typeArtigo de periódico
local.citation.epage12468
local.citation.issue22
local.citation.spage12459
local.citation.volume72
local.creator.Latteshttp://lattes.cnpq.br/9158036916035187
local.creator.Latteshttp://lattes.cnpq.br/6900574220406100
local.creator.Latteshttp://lattes.cnpq.br/6104660258664620
local.creator.Latteshttp://lattes.cnpq.br/9963384168622230
local.creator.Latteshttps://orcid.org/0000-0003-3230-9101
local.creator.Latteshttp://lattes.cnpq.br/6727861982577995
local.creator.Latteshttp://lattes.cnpq.br/9121022613112821
local.description.resumoA 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 e(ective, 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.
local.identifier.orcidhttps://orcid.org/0000-0002-9654-8622
local.identifier.orcidhttps://orcid.org/0000-0002-5341-2151
local.identifier.orcidhttps://orcid.org/0000-0003-3181-1108
local.identifier.orcidhttps://orcid.org/0000-0002-8170-125X
local.identifier.orcidhttps://orcid.org/0000-0003-2754-2013
local.identifier.orcidhttps://orcid.org/0000-0002-2254-6683
local.identifier.orcidhttps://orcid.org/0000-0001-9463-2567
local.identifier.orcidhttps://orcid.org/0000-0002-5395-9608
local.identifier.orcidhttps://orcid.org/0000-0002-7968-8586
local.identifier.orcidhttps://orcid.org/0000-0002-8257-5443
local.identifier.orcidhttps://orcid.org/0000-0001-5501-7350
local.identifier.orcidhttps://orcid.org/0000-0001-5711-0268
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.subject.cnpqCIENCIAS EXATAS E DA TERRA
local.url.externahttps://pubs.acs.org/doi/10.1021/acs.jafc.4c00440

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