Thymol and its Derivatives for Management of Phytopathogenic fungi of maize

Background: Thymol is a bioactive compound having many pharmacological activities. Objective: The present study was carried out to evaluate the fungi toxic effects of thymol and derivatives against phytopathogenic fungi of maize. Method: Thymol was derivatized to get formylated thymol, Mannich bases, and imine derivatives. All the synthesized thymol derivatives were characterized by their physical and spectral properties. Synthesized thymol derivatives were screened for their in vitro antifungal effects using poisoned food technique against three maize pathogenic fungi namely Fusarium moniliforme, Rhizoctonia solani and Dreschlera maydis. Results: Thymol and formylated thymol showed promising results for control of D. maydis with ED50 values less than standard carbendazim and comparable to standard mancozeb. These two compounds were further evaluated for control of D. maydis causative maydis leaf blight disease on maize plants grown in the field during the Kharif season (June to October) 2018. Conclusion: Thymol exhibited significant control of maydis leaf blight disease of maize and emerged as a potential alternative to synthetic fungicides used in cereal crops.

Eugenol and Thymol Derivatives as Antifeedant Agents against Red Palm Weevil, Rhynchophorus ferrugineus (Coleoptera: Dryophthoridae) Larvae

Coconut palms in Malaysia are infested by a destructive invasive pest, RPW since 2007, and the pest’s population is difficult to control. At present, RPW control management mainly relies on the use of monocrotophos, which is administered by the trunk injection method. However, this pesticide can negatively impact human health and the ecosystem. Plant EO that can be used as a bio-pesticide is highly recommended as an alternative to monocrotophos because of its target-specific and eco-friendly properties. The antifeedant activity of eight eugenol and thymol derivatives from clove and thyme EOs were tested against the fourth instar larvae of RPW through oral bioassay for 14 days. Relative growth rate (RGR), relative consumption rate (RCR), the efficiency of conversion of ingested food (ECI), and the feeding deterrent index (FDI) were compared and analyzed. All of the derivatives showed antifeedant activity, particularly the eugenol derivative, 4-allyl-2-methoxy-1-(4-trifluoromethyl-benzyloxy)-benzene (FDI = 54.14%) and the thymol derivative, 2-isopropyl-4-methyl-2-((4-nitrobenzyl) oxy) benzene (FDI = 53.88%). Both of them showed promising results on their ability to be the most effective antifeedant agents in each derivative group. There was no significant difference in the effectiveness of the eugenol-based and thymol-based derivatives, but the ether derivative group (FDI = 45.63%) had a significantly stronger effect than the ester derivative group (FDI = 39.71%). This study revealed that the compound in ether form is more effective than the compound in ester form as an antifeedant agent against RPW larvae, regardless of the plant EO that the compound is derived from.

Comparative Protective Effect of Nigella sativa Oil and Vitis vinifera Seed Oil in an Experimental Model of Isoproterenol-Induced Acute Myocardial Ischemia in Rats

The study’s aim was to characterize the composition of Nigella sativa seed (NSO) and grape seed (GSO) oils, and to evaluate their cardioprotective and anti-inflammatory effect on isoproterenol (ISO)-induced ischemia in rats. Materials and Methods: NSO and GSO supplements were physicochemically characterized. Liquid chromatography–mass spectrometry (HPLC-MS), Fourier-transform infrared spectroscopy (FTIR), and gas chromatography–mass spectrometry (GC-MS) analyses were used to determine the phytochemical composition in the oils. Total polyphenol content (TPC) and in vitro antioxidant activity were also determined. Pretreatment with 4 mL/kg/day NSO or GSO was administered to rats for 14 days. The experimental ischemia was induced by a single administration of ISO 45 mg/kg after 14 days. An electrocardiogram (ECG) was performed initially and 24 h after ISO. Biological evaluation was done at the end of experiment. Results: The HPLC-MS, GC-MS, and FTIR analyses showed that both NSO and GSO are important sources of bioactive compounds, especially catechin and phenolic acids in GSO, while NSO was enriched in flavonoids and thymol derivatives. Pretreatment with GSO and NSO significantly reduced ventricular conduction, prevented the cardiotoxic effect of ISO in ventricular myocardium, and reduced the level of proinflammatory cytokines and CK-Mb. Conclusion: Both NSO and GSO were shown to have an anti-inflammatory and cardioprotective effect in ISO-induced ischemia.

4-Chlorothymol Exerts Antiplasmodial Activity Impeding Redox Defense System in Plasmodium falciparum

Malaria remains one of the major health concerns due to the resistance of Plasmodium species toward the existing drugs warranting an urgent need for new antimalarials. Thymol derivatives were known to exhibit enhanced antimicrobial activities; however, no reports were found against Plasmodium spp. In the present study, the antiplasmodial activity of thymol derivatives was evaluated against chloroquine-sensitive (NF-54) and -resistant (K1) strains of Plasmodium falciparum. Among the thymol derivatives tested, 4-chlorothymol showed potential activity against sensitive and resistant strains of P. falciparum. 4-Chlorothymol was found to increase the reactive oxygen species and reactive nitrogen species level. Furthermore, 4-chlorothymol could perturb the redox balance by modulating the enzyme activity of GST and GR. 4-Chlorothymol also showed synergy with chloroquine against chloroquine-resistant P. falciparum. 4-Chlorothymol was found to significantly suppress the parasitemia and increase the mean survival time in in vivo assays. Interestingly, in in vivo assay, 4-chlorothymol in combination with chloroquine showed higher chemosuppression as well as enhanced mean survival time at a much lower concentration as compared to individual doses of chloroquine and 4-chlorothymol. These observations clearly indicate the potential use of 4-chlorothymol as an antimalarial agent, which may also be effective in combination with the existing antiplasmodial drugs against chloroquine-resistant P. falciparum infection. In vitro cytotoxicity/hemolytic assay evidently suggests that 4-chlorothymol is safe for further exploration of its therapeutic properties.

Thymol derivatives with antibacterial and cytotoxic activity from the aerial parts of Ageratina adenophora

Eight thymol derivatives including three new ones (1–3) were obtained from the aerial parts of Ageratina adenophora, with most of them, in particular 1 and 5, showing notable in vitro antimicrobial and cytotoxic activity.

New carvacrol and thymol derivatives as potential insecticides: synthesis, biological activity, computational studies and nanoencapsulation

Thymol and carvacrol derivatives were synthesised. Two of them proved to be mildly active against Sf9 insect cell line and one has presented selectivity by proving to be less toxic to human cells than the naturally derived starting materials.

Constituents of Xerolekia speciosissima (L.) Anderb. (Inuleae), and Anti-Inflammatory Activity of 7,10-Diisobutyryloxy-8,9-epoxythymyl Isobutyrate

Xerolekia speciosissima (L.) Anderb., a rare plant from the north of Italy, is a member of the Inuleae-Inulinae subtribe of the Asteraceae. Despite its close taxonomic relationship with many species possessing medicinal properties, the chemical composition of the plant has remained unknown until now. A hydroalcoholic extract from the aerial parts of X. speciosissima was analyzed by HPLC-DAD-MSn, revealing the presence of caffeic acid derivatives and flavonoids. In all, 19 compounds, including commonly found chlorogenic acids and less frequently occurring butyryl and methylbutyryl conjugates of dicaffeoylquinic and tricaffeoylhexaric acids, plus two flavonoids, were tentatively identified. Chromatographic separation of a hydroalcoholic extract from the capitula of the plant led to the isolation of (+)-dehydrodiconiferyl alcohol 4-O-β-glucopyranoside, quercimeritrin, astragalin, isoquercitrin, 6-hydroxykaempferol-7-O-β-glucoside, quercetagitrin, methyl caffeate, caffeic acid, protocatechuic acid, chlorogenic acid and 1,5-dicaffeoylquinic acid. Composition of a nonpolar extract from the aerial parts of the plant was analyzed by chromatographic methods supported with 1H-NMR spectroscopy. The analysis revealed the presence of loliolide, reynosin, samtamarine, 2,3-dihydroaromaticin, 2-deoxy-4-epi-pulchellin and thymol derivatives as terpenoid constituents of the plant. One of the latter compounds—7,10-diisobutyryloxy-8,9-epoxythymyl isobutyrate—at concentrations 0.5, 1.0 and 2.5 μM, significantly reduced IL-8, IL-1β and CCL2 excretion by LPS-stimulated human neutrophils.

Synthesis and Biological Evaluation of Thymol Functionalized Oxadiazole thiol, Triazole thione and β-lactam Derivatives

Abstract:: In the present study, different derivatives of thymol (1) viz. hydrazide (2), oxadiazole thiol (3), triazole thione (4), hydrazones (5-7) and β-lactams (8-10) were synthesized. All synthesized compounds were identified and characterized using elemental analysis, UV-Visible, 1H NMR, 13C NMR, IR spectroscopic techniques. Synthesized thymol derivatives were evaluated for antifungal potential against phytopathogenic fungi Fusarium moniliforme, Rhizoctonia solani, Dreschlera madis of maize in comparison to recommended standards in terms of percent inhibition and ED50 values. Thymol was more effective as compared to its derivatives against all three tested fungi. Hydrazones (5-7) and β-lactams (8-10) having m-NO2 substituted phenyl ring (6, 9) were less effective as compared to o-NO2 and p-NO2 analogues against F. moniliforme and R. solani, however reverse trend was observed against D. maydis. Thymol and its derivatives were also tested for insecticidal activity against stored grain (chickpea) insect Callosobruchus chinensis and various parameters viz. egg laying, adult emergence and grain damage were recorded and compared. Compounds having oxadiazole thiol (3) and triazole thione (4) moiety showed promising effects against insect C. chinensis.

Bioassay-Guided Isolation of Antiproliferative Compounds from Limbarda crithmoides (L.) Dumort

Limbarda crithmoides (L.) Dumort (Asteraceae) n-hexane extract displayed high cell proliferation inhibitory activity against acute myeloid leukaemia cells (OCI-AML3) and was therefore subjected to a bioassay-guided multistep separation procedure. Two thymol derivatives, namely 10-acetoxy-8,9-epoxythymol tiglate (1) and 10-acetoxy-9-chloro-8,9-dehydrothymol (2), were isolated and identified by means of NMR spectroscopy. Both of them exhibited a significant dose-dependent inhibition of cell proliferation.