3β-O-Tigloylmelianol from Guarea kunthiana: A New Potential Agent to Control Rhipicephalus (Boophilus) microplus, a Cattle Tick of Veterinary Significance
Carlos Henrique Miguita,
Carolina da Silva Barbosa,
Lidilhone Hamerski,
Ulana Chaves Sarmento,
José Nicácio do Nascimento,
Walmir Silva Garcez,
Fernanda Rodrigues Garcez
Affiliations
Carlos Henrique Miguita
Laboratório de Pesquisa de Produtos Naturais Bioativos, Instituto de Química, Universidade Federal de Mato Grosso do Sul, 79074-460 Campo Grande, MS, Brazil
Carolina da Silva Barbosa
Laboratório de Parasitologia Animal, Universidade Estadual de Mato Grosso do Sul, 79200-000 Aquidauana, MS, Brazil
Lidilhone Hamerski
Laboratório de Pesquisa de Produtos Naturais Bioativos, Instituto de Química, Universidade Federal de Mato Grosso do Sul, 79074-460 Campo Grande, MS, Brazil
Ulana Chaves Sarmento
Laboratório de Pesquisa de Produtos Naturais Bioativos, Instituto de Química, Universidade Federal de Mato Grosso do Sul, 79074-460 Campo Grande, MS, Brazil
José Nicácio do Nascimento
Laboratório de Insetos Frugíforos, Faculdade de Ciências Biológicas e Ambientais, Universidade Federal da Grande Dourados, 79804-970 Dourados, MS, Brazil
Walmir Silva Garcez
Laboratório de Pesquisa de Produtos Naturais Bioativos, Instituto de Química, Universidade Federal de Mato Grosso do Sul, 79074-460 Campo Grande, MS, Brazil
Fernanda Rodrigues Garcez
Laboratório de Pesquisa de Produtos Naturais Bioativos, Instituto de Química, Universidade Federal de Mato Grosso do Sul, 79074-460 Campo Grande, MS, Brazil
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.
