title: 3β-O-tigloylmelianol from Guarea kunthiana: a new potential agent to control Rhipicephalus (Boophilus) microplus, a cattle tick of veterinary significance.
abstract: Chemical investigation of Guarea kunthiana fruits, guided by their effect on the reproductive cycle of engorged females of the cattle tick Rhipicephalus (Boophilus) microplus-a major economic problem to the livestock industry worldwide-led to isolation of 3β-O-tigloylmelianol, a new protolimonoid, from the bioactive hexane phase obtained by partitioning the crude ethanol extract. An adult immersion test was performed. The compound strongly inhibited egg-laying and hatchability (99.2% effectiveness at a 0.01% concentration). Melianone, isolated from the same phase, yielded unremarkable results in the adult immersion test. From the dichloromethane phase, melianol, melianodiol, meliantriol, and a new protolimonoid, 3β-O-tigloylmeliantriol, were isolated, all of which, in the same manner as melianone, exhibited unremarkable results in the test. The structures of new and known compounds were mostly established by 1D- and 2D-NMR analyses and mass spectrometry data. This is the first report on the bioactivity of protolimonoids on the reproductive cycle of engorged females of R. (B.) microplus. 3β-O-Tigloylmelianol proved a promising candidate for the development of a biocontrol agent against the cattle tick investigated, as an alternative to environmentally hazardous synthetic acaricides.
authors.affiliation: Laboratório de Pesquisa de Produtos Naturais Bioativos, Instituto de Química, Universidade Federal de Mato Grosso do Sul, 79074-460 Campo Grande, MS, Brazil. miguita_carloshenrique@hotmail.com.
authors.forename: Carlos Henrique
authors.initials: CH
authors.lastname: Miguita
authors.affiliation: Laboratório de Parasitologia Animal, Universidade Estadual de Mato Grosso do Sul, 79200-000 Aquidauana, MS, Brazil. csmangarosa@gmail.com.
authors.forename: Carolina da Silva
authors.initials: Cda S
authors.lastname: Barbosa
authors.affiliation: Laboratório de Pesquisa de Produtos Naturais Bioativos, Instituto de Química, Universidade Federal de Mato Grosso do Sul, 79074-460 Campo Grande, MS, Brazil. hamerski_l@hotmail.com.
authors.forename: Lidilhone
authors.initials: L
authors.lastname: Hamerski
authors.affiliation: Laboratório de Pesquisa de Produtos Naturais Bioativos, Instituto de Química, Universidade Federal de Mato Grosso do Sul, 79074-460 Campo Grande, MS, Brazil. ulanachaves@hotmail.com.
authors.forename: Ulana Chaves
authors.initials: UC
authors.lastname: Sarmento
authors.affiliation: Laboratório de Insetos Frugíforos, Faculdade de Ciências Biológicas e Ambientais, Universidade Federal da Grande Dourados, 79804-970 Dourados, MS, Brazil. nicacioj.n@gmail.com.
authors.forename: José Nicácio do
authors.initials: JN
authors.lastname: Nascimento
authors.affiliation: Laboratório de Pesquisa de Produtos Naturais Bioativos, Instituto de Química, Universidade Federal de Mato Grosso do Sul, 79074-460 Campo Grande, MS, Brazil. inqui@ufms.br.
authors.forename: Walmir Silva
authors.initials: WS
authors.lastname: Garcez
authors.affiliation: Laboratório de Pesquisa de Produtos Naturais Bioativos, Instituto de Química, Universidade Federal de Mato Grosso do Sul, 79074-460 Campo Grande, MS, Brazil. fernandargarcez@gmail.com.
authors.forename: Fernanda Rodrigues
authors.initials: FR
authors.lastname: Garcez
mesh_terms: D056810:Acaricides / Q000494:pharmacology*; D000818:Animals; D002417:Cattle / Q000523:psychology*; D002418:Cattle Diseases / Q000469:parasitology*; D005260:Female; D036701:Limonins / Q000302:isolation & purification / Q000494:pharmacology*; D029582:Meliaceae / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D048494:Rhipicephalus / Q000187:drug effects* / Q000472:pathogenicity; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: C000601870:3beta-O-tigloylmelianol; D056810:Acaricides; D036701:Limonins