2. Academic Validation
  3. 3β-O-tigloylmelianol from Guarea kunthiana: a new potential agent to control Rhipicephalus (Boophilus) microplus, a cattle tick of veterinary significance

3β-O-tigloylmelianol from Guarea kunthiana: a new potential agent to control Rhipicephalus (Boophilus) microplus, a cattle tick of veterinary significance

  • Molecules. 2014 Dec 23;20(1):111-26. doi: 10.3390/molecules20010111.
Carlos Henrique Miguita 1,  Carolina da Silva Barbosa 2,  Lidilhone Hamerski 3,  Ulana Chaves Sarmento 4,  José Nicácio do Nascimento 5,  Walmir Silva Garcez 6,  Fernanda Rodrigues Garcez 7
Affiliations

Affiliations

  • 1 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.
  • 2 Laboratório de Parasitologia Animal, Universidade Estadual de Mato Grosso do Sul, 79200-000 Aquidauana, MS, Brazil. csmangarosa@gmail.com.
  • 3 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.
  • 4 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.
  • 5 Laboratório de Insetos Frugíforos, Faculdade de Ciências Biológicas e Ambientais, Universidade Federal da Grande Dourados, 79804-970 Dourados, MS, Brazil. nicacioj.n@gmail.com.
  • 6 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.
  • 7 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.
PMID: 25546624 DOI: 10.3390/molecules20010111
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.

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