title: Activity of chalcones derived from 2,4,5-trimethoxybenzaldehyde against Meloidogyne exigua and in silico interaction of one chalcone with a putative caffeic acid 3-O-methyltransferase from Meloidogyne incognita.
abstract: Meloidogyne exigua is a parasitic nematode of plants that causes great losses to coffee farmers. In an effort to develop parasitic controls, 154 chalcones were synthesized and screened for activity against this nematode. The best results were obtained with (2E)-1-(4'-nitrophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one (6) with a 50% lethal concentration (LC50) of 171 μg/ml against M. exigua second-stage juveniles, in comparison to the commercially-available nematicide carbofuran which had an LC50 of 260 μg/ml under the same conditions. When coffee plants were used, 6 reduced the nematode population to ~50% of that observed in control plants. To investigate the mechanism of action of 6, an in silico study was carried out, which indicated that 6 may act against M. exigua through inhibition of a putative caffeic acid 3-O-methyltransferase homodimer, the amino acid sequence of which was determined by examining the genome of Meloidogyne incognita.
authors.affiliation: Universidade Federal de Lavras, Departamento de Química, 37200-000 Lavras, MG, Brazil.
authors.forename: Alexandro Silva
authors.initials: AS
authors.lastname: Nunes
authors.forename: Vicente Paulo
authors.initials: VP
authors.lastname: Campos
authors.forename: Alessandra
authors.initials: A
authors.lastname: Mascarello
authors.forename: Taisa Regina
authors.initials: TR
authors.lastname: Stumpf
authors.forename: Louise Domenghini
authors.initials: LD
authors.lastname: Chiaradia-Delatorre
authors.forename: Alan Rodrigues Teixeira
authors.initials: AR
authors.lastname: Machado
authors.forename: Helvécio Martins
authors.initials: HM
authors.lastname: Santos Júnior
authors.forename: Rosendo Augusto
authors.initials: RA
authors.lastname: Yunes
authors.forename: Ricardo José
authors.initials: RJ
authors.lastname: Nunes
authors.forename: Denilson Ferreira
authors.initials: DF
authors.lastname: Oliveira
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D001547:Benzaldehydes / Q000737:chemistry*; D047188:Chalcones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D040503:Coffea / Q000469:parasitology*; D007928:Lethal Dose 50; D008024:Ligands; D000455:Medicago sativa / Q000201:enzymology; D008780:Methyltransferases / Q000037:antagonists & inhibitors* / Q000737:chemistry; D008969:Molecular Sequence Data; D010935:Plant Diseases / Q000469:parasitology / Q000517:prevention & control; D014431:Tylenchoidea / Q000187:drug effects* / Q000201:enzymology
chemical_list: D001547:Benzaldehydes; D047188:Chalcones; D008024:Ligands; C034031:2,4,5-trimethoxybenzaldehyde; D008780:Methyltransferases; C019608:caffeate O-methyltransferase
keywords: (2E)-1-(4′-Nitrophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one; Chalcone; Meloidogyne; Nematicide; Protein modeling; Root-knot nematode