Aliphatic Ketones from Ruta chalepensis (Rutaceae) Induce Paralysis on Root Knot Nematodes

Department of Pharmaceutical Chemistry and Technology, University of Cagliari, Cagliari, Italy.
Journal of Agricultural and Food Chemistry (Impact Factor: 2.91). 06/2011; 59(13):7098-103. DOI: 10.1021/jf2013474
Source: PubMed


This paper reports on the use of Ruta chalepensis L. extracts as a potential nematicide against root knot nematodes Meloidogyne incognita and Meloidogyne javanica . The essential oil (REO) and methanol extract (RME) of R. chalepensis were tested against second-stage juveniles, with REO inducing paralysis in both species (EC(50/1d) = 77.5 and 107.3 mg/L) and RME being selective for M. incognita (EC(50/1d) = 1001 mg/L). Chemical characterization of extracts was done by means of GC-MS and LC-MS, revealing mainly aliphatic ketones and coumarins, respectively. The first-ranking volatile nematicidal component in terms of individual activity against both species was 2-undecanone (EC(50) = 20.6 and 22.5 mg/L for M. incognita and M. javanica, respectively). This fact together with its high concentration in the most active extract found in this study, namely, REO (2926 mg/kg), categorizes 2-undecanone among the nematicidal principles of R. chalepensis. On the contrary, coumarins rutin and 8-methoxypsoralen were not found to be nematicidal at concentrations of ≤500 mg/L. Interestingly, M. incognita was found more sensitive than M. javanica.

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    • "The fragmentation molecular produces a fragment at m/z 465 and 303. This compound was tentatively identified as rutin which was earlier reported in the aerial part of R. chalepensis L. (Ntalli et al., 2011). – Isorhamnetin 3-O-Rutinoside (molecular formula C 28 H 31 O 16 ) is identified in peak 5 (t R ¼11.13) with a positive molecular ion at [M þH] þ at an m/z of 624 and fragmentation product at m/z of 316 and 301. "
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    ABSTRACT: In this paper, the chemical composition of different solvent extracts from Ruta chalepensis L was determined and their antioxidant and antimicrobial activities were evaluated. Indeed, the total phenol, flavonoids, ortho-diphenols, tannin and flavonols contents of these extracts were quantified, with a total phenolic content varying from 120.57 to 178.00 mg Gallic acid equivalents per gram of dry extract. The chemical analysis of the composition of these Ruta chalepensis L. extracts has shown a high content of coumarins and alkaloid compounds. Besides, their antioxidant activities were examined using various in vitro assays: DPPH radical scavenging, β-carotene bleaching method, reducing power and quantification of the total antioxidant capacity. The obtained results have confirmed that the ethanol extract exhibits the most potent antioxidant effect, followed by methanol and methanol/water (1/1) extracts. Furthermore, the ethanol, methanol, methanol/water (1/1) and ethyl acetate extracts were found to have an antibacterial activity against gram positive and gram negative strains.
    Food Bioscience 08/2015; 12(13). DOI:10.1016/j.fbio.2015.08.001
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    • "Furthermore, its ability in controlling root-knot nematodes shows a higher reduction of galling index and nematode eggs if compared with the treatment with conventional nematicides fenamiphos or oxamyl [4]. The limited number of categories of nematicidal agents has prompted a search for compounds preferably of plant origin with alternative modes of action [5] [6] [7]. Moreover , in order to prevent or delay the rapid development of resistance, one of the major issues in resistance management strategies has been the rotation of compounds with different modes of action [8]. "
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    ABSTRACT: Carbonyl groups are known to form covalent adducts with endogenous proteins, but so far, their nematicidal mechanism of action of has been overlooked. The nematicidal activity of ten lactones was tested in vitro against the root knot nematodes Meloidogyne incognita and Meloidogynearenaria. In particular, the saturated lactones α-methylene-γ-butyrolactone or tulipaline A (1) and γ-butyrolactone (3) were active against M. incognita with an EC50/48h of 19.3±10.0 and 40.0±16.2mg/L respectively. Moreover the α, β-unsaturated lactone 5,6-dihydro-2H-pyran-2-one (2) exhibited the strongest nematicidal activity against the two species with EC50/48h 14.5±5.3 and 21.2±9.7mg/L respectively. Here we propose that the toxic effects of lactones and aldehydes on M.incognita and M. arenaria might be a consequence of their vacuolar-type H(+)-ATPase (V-ATPase) inhibition activity; in fact α-methylene-γ-butyrolactone (1) and salicylaldehyde (12) produced an increased pH in lysosomal-like organelles on HeLa human cell line and this alteration was most likely related to a V-ATPase impairment.
    Pesticide Biochemistry and Physiology 06/2014; 112(1). DOI:10.1016/j.pestbp.2014.05.002 · 2.01 Impact Factor
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    • "The concentrates consist of a mixture of many volatile compounds, such as alcohols, aldehydes, ketones, esters, aromatic phenols, and lactones, as well as monoterpenes and sesquiterpenes . While the essential oils and their components have demonstrated a broad insecticidal or nematicidal activity [11] [12] [13], many previous studies have also shown that some essential oils or their constituents have showed a strong nematicidal activity, specifically against the pinewood nematode [14] [15] [16] [17] [18] [19] [20] [21] [22]. Although, the primary mode of action of these essential oils is unclear, an insight into its mechanism is necessary to enable efficient screening for effective nematicidal agents. "
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    ABSTRACT: To understand the nematicidal mode of action of phytochemicals derived from plant essential oils against the pinewood nematode (Bursaphelenchus xylophilus), we evaluated 97 compounds (49 monoterpenes, 17 phenylpropenes, 16 sesquiterpenes, and 15 sulfides) for their inhibitory effects on B. xylophilus acetylcholinesterases (BxACEs). In the primary inhibition assay using B. xylophilus crude protein, more than 50% BxACE inhibition activity was observed with 3 monoterpenes, (+)-α-pinene, (-)-α-pinene, and 3-carene; 2 phenylpropenes, ο-anisaldehyde, and coniferyl alcohol; and 1 sesquiterpene, cis-nerolidol. Other compounds showed moderate or weak inhibitory activity. The inhibitory activities against 3 recombinant BxACEs were subsequently estimated using the identified active compounds in a primary inhibition assay. (+)-α-Pinene showed the strongest inhibition of BxACE-1 followed by 3-carene, coniferyl alcohol, (-)-α-pinene, o-anisaldehyde, and cis-nerolidol. The half maximal inhibitory concentration (IC50) values of (+)-α-pinene, 3-carene, o-anisaldehyde, cis-nerolidol, and (-)-α-pinene against BxACE-2 were found to be 0.64, 1.41, 8.18, 8.53, 15.28, and 18.03mM, respectively. Coniferyl alcohol showed the strongest inhibition of BxACE-3 followed by (+)-α-pinene and cis-nerolidol.
    Pesticide Biochemistry and Physiology 11/2013; 105(1):50-6. DOI:10.1016/j.pestbp.2012.11.007 · 2.01 Impact Factor
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