Nematostatic activity of isoprenylated guanidine alkaloids from Pterogyne nitens and their interaction with acetylcholinesterase

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dc.contributor.authorCoqueiro, Aline [UNESP]
dc.contributor.authorFernandes, Daniara Cristina [UNESP]
dc.contributor.authorDanuello, Amanda [UNESP]
dc.contributor.authorRegasini, Luis Octávio [UNESP]
dc.contributor.authorCardoso-Lopes, Elaine Monteiro
dc.contributor.authorYoung, Maria Cláudia Marx
dc.contributor.authorBrandão Torres, Luce Maria
dc.contributor.authorCampos, Vicente Paulo
dc.contributor.authorSilva, Dulce Helena Siqueira [UNESP]
dc.contributor.authorda Silva Bolzani, Vanderlan [UNESP]
dc.contributor.authorde Oliveira, Denilson Ferreira
dc.contributor.institutionUniversidade Estadual Paulista (UNESP)
dc.contributor.institutionFederal University of Technology – Paraná (UTFPR)
dc.contributor.institutionScience and Technology of São Paulo (IFSP)
dc.contributor.institutionUniversidade Federal de Uberlândia (UFU)
dc.contributor.institutionInstitute of Environmental Research
dc.contributor.institutionUniversidade Federal de Lavras (UFLA)
dc.date.accessioned2023-07-29T13:55:36Z
dc.date.available2023-07-29T13:55:36Z
dc.date.issued2023-07-01
dc.description.abstractAlthough new nematicides have appeared, the demand for new products less toxic and more efficient for the control of plant-parasitic nematodes are still high. Consequently, studies on natural secondary metabolites from plants, to develop new nematicides, have increased. In this work, nineteen extracts from eleven Brazilian plant species were screened for activity against Meloidogyne incognita. Among them, the extracts of Piterogyne nitens showed a potent nematostatic activity. The alkaloid fraction obtained from the ethanol extract of leaves of P. nitens was more active than the coming extract. Due to the promising activity from the alkaloid fraction, three isoprenylated guanidine alkaloids isolated from this fraction, galegine (1), pterogynidine (2), and pterogynine (3) were tested, showing similar activity to the alkaloid fraction, which was comparable to that of the positive control Temik at 250 μg/mL. At lower concentrations (125−50 μg/mL), compound 2 showed to be the most active one. As several nematicides act through inhibition of acetylcholinesterase (AChE), the guanidine alkaloids were also employed in two in vitro AChE assays. In both cases, compound 2 was more active than compounds 1 and 3. Its activity was considered moderated compared to the control (physostigmine). Compound 2 was selected for an in silico study with the electric eel (Electrophorus electricus) AChE, showing to bind mostly to the same site of physostigmine in the AChEs, pointing out that this could be the mechanism of action for this compound. These results suggested that the guanidine alkaloids 1, 2 and 3 from P. nitens are promising for the development of new products to control M. incognita, especially guanidine 2, and encourage new investigations to confirm the mechanism of action, as well as to determine the structure-activity relationship of the guanidine alkaloids.en
dc.description.affiliationNuclei of Bioassays Biosynthesis and Ecophysiology of Natural Products (NuBBE) Department of Organic Chemistry Institute of Chemistry São Paulo State University (UNESP), SP
dc.description.affiliationDepartment of Chemistry Federal University of Technology – Paraná (UTFPR), PR
dc.description.affiliationFederal Institute of Education Science and Technology of São Paulo (IFSP), SP
dc.description.affiliationInstitute of Chemistry Federal University of Uberlândia (UFU), MG
dc.description.affiliationDepartme nt of Chemistry and Environmental Sciences Institute of Biosciences Humanities and Exact Sciences São Paulo State University (UNESP), SP
dc.description.affiliationInstitute of Environmental Research, SP
dc.description.affiliationDepartment of Phytopathology Federal University of Lavras (UFLA), MG
dc.description.affiliationDepartment of Chemistry Federal University of Lavras (UFLA), MG
dc.description.affiliationUnespNuclei of Bioassays Biosynthesis and Ecophysiology of Natural Products (NuBBE) Department of Organic Chemistry Institute of Chemistry São Paulo State University (UNESP), SP
dc.description.affiliationUnespDepartme nt of Chemistry and Environmental Sciences Institute of Biosciences Humanities and Exact Sciences São Paulo State University (UNESP), SP
dc.description.sponsorshipCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG)
dc.identifierhttp://dx.doi.org/10.1016/j.exppara.2023.108542
dc.identifier.citationExperimental Parasitology, v. 250.
dc.identifier.doi10.1016/j.exppara.2023.108542
dc.identifier.issn1090-2449
dc.identifier.issn0014-4894
dc.identifier.scopus2-s2.0-85159864455
dc.identifier.urihttp://hdl.handle.net/11449/248858
dc.language.isoeng
dc.relation.ispartofExperimental Parasitology
dc.sourceScopus
dc.subjectBiodiversity
dc.subjectGalegine
dc.subjectMeloidogyne incognita
dc.subjectNematodes
dc.subjectPterogynidine
dc.subjectPterogynine
dc.titleNematostatic activity of isoprenylated guanidine alkaloids from Pterogyne nitens and their interaction with acetylcholinesteraseen
dc.typeArtigo
unesp.author.orcid0000-0002-9597-1322 0000-0002-9597-1322[1]
unesp.author.orcid0000-0001-9326-8716[11]

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