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, OPEN ACCESSMolecules 2015, 20 112 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.

Insecticidal, biological and biochemical response of Musca domestica (Diptera: Muscidae) to some indigenous weed plant extracts

“…C. murale showed highest oviposition deterrence activity (81.88%) followed by D. stramonium (79.58%), A. indica (74.10%), P. harmala , (68.14%) and T. terrestris (48.96%). Inhibition of egg-laying and hatchability (99.2% effectiveness at a 0.01% concentration) due to compound extracted from Guarea kunthiana against cattle tick Rhipicephalus (Boophilus) microplus is reported by Miguita et al (2014). Lantana camara extract caused significant reduction in number of eggs of M. domestica as reported by Elkattan et al (2011).…”

Larvicidal efficacies of plants from Midwestern Brazil: melianodiol from Guarea kunthiana as a potential biopesticide against Aedes aegypti

“…This phase was then subjected to column chromatography procedures and the resulting bioactive fraction (LC 50 = 15.20 mg/mL, Table II ), containing two principal components, was further separated, leading to the isolation and characterisation of the known protolimonoids melianodiol ( 1 , major compound) and meliantriol ( 2 ) ( Figure ). Their structures were established on the basis of 1 H and 13 C NMR spectroscopic techniques supported by mass spectra, as well as by comparison with previously reported data, and authentic samples ( Puripattanavong et al 2000 , Kurimoto et al 2014 , Miguita et al 2015 ).…”

“…Meliaceae, the family to which the genus Guarea belongs, is a rich source of secondary metabolites, including limonoids and protolimonoids ( Taylor 1984 , Tan & Luo 2011 ). In a previous investigation of G. kunthiana , we isolated 1 and 2 from the fruits, and di- and sesquiterpenes, poliprenol-12, and α- and d-tocopherols from the leaves ( Garcez et al 2004 , Miguita et al 2015) . The fruits also yielded the limonoids humilinolide E, 2-hydroxy-6-deoxyswietenine, swietenin acetate and methyl angolensate ( Miguita et al 2014) , none of which were found to be present in our G. kunthiana bioactive fraction from which melianodiol ( 1 ) was obtained, despite the fact that limonoids are known for their biological, and particularly insecticidal, properties ( Tan & Luo 2011) .…”

Inhibitory Effect and Antimicrobial Activity of Secondary Metabolites of <i>Khaya Senegalensis</i> (Desr.) A. Juss. (Meliaceae)

“…On its 13 . By comparison of its spectral data with those described in the literature, the structure of compound 3 is identified with that of Methyl angolensate compound isolated for the first time from the fruits of Guarea kunthiana and exhibiting numerous biological activities: antiappetant, insecticide, anti-tumor against human cells (liver, kidney) [41,42].…”