Compounds isolated from botanical sources represent innovative and promising alternatives to conventional insecticides. Carlina oxide is a compound isolated from Carlina acaulis L. (Asteraceae) essential oil (EO) with great potential as bioinsecticide, being effective on various arthropod vectors and agricultural pests, with moderate toxicity on non-target species. Since the production from the wild source is limited, there is the need of exploring new synthetic routes for obtaining this compound and analogues with improved bioactivity and lower toxicity. Herein, the chemical synthesis of carlina oxide analogues was developed. Their insecticidal activity was assessed on the vectors Musca domestica L. and Culex quinquefasciatus Say, and their cytotoxicity was evaluated on a human keratinocyte cell line (HaCaT). The compounds' activity was compared with that of the natural counterparts EO and carlina oxide. In housefly tests, the analogues were comparably effective to purified carlina oxide. In Cx. quinquefasciatus assays, the meta-chloro analogue provided a significantly higher efficacy (LC50 of 0.71 μg mL-1) than the EO and carlina oxide (LC50 1.21 and 1.31 μg mL-1, respectively) and a better safety profile than carlina oxide on keratinocytes. Overall, this study can open the way to an agrochemical production of carlina oxide analogues employable as nature-inspired insecticides.
- MeSH
- Asteraceae * chemie MeSH
- Culex * MeSH
- insekticidy * farmakologie MeSH
- komáří přenašeči MeSH
- larva MeSH
- lidé MeSH
- oleje prchavé * farmakologie chemie MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
In recent years, agrochemical industries have been focused on the development of essential oil (EO)-based biopesticides, which can be considered valuable alternatives to traditional chemical products. The genus Mentha (Lamiaceae) comprises 30 species characterized by a wide range of biological activities, and some of their EOs showed good potential as pesticidal agents. In this regard, the aim of this study was to evaluate the insecticidal activity of the EO obtained from a rare linalool/linalool acetate chemotype of Mentha aquatica L. The EO was found to be highly effective against Culex quinquefasciatus (Say) 2nd instar larvae, Metopolophium dirhodum (Walker) adults, Spodoptera littoralis (Boisduval) 2nd instar larvae, and Tetranychus urticae (Koch) adults, showing lethal concentrations (LC50) or doses (LD50) of 31.5 ± 2.2 μL L-1, 4.9 ± 0.8 mL L-1, 18.5 ± 2.1 μg larvae-1, and 3.3 ± 0.5 mL L-1, respectively. On the contrary, Musca domestica L. adults and 3rd instar larvae of C. quinquefasciatus and S. littoralis were moderately affected by the treatment (LC50 or LD50: 71.4 ± 7.2 μg adult-1, 79.4 ± 5.2 μL L-1, 44.2 ± 5.8 μg larvae-1, respectively). The results obtained in this work demonstrated that various insects and pests could be differently sensible to the same EO and may lead to the exploitation of this plant or its major volatile compounds as novel ingredients of botanical insecticides and pesticides.
- Publikační typ
- časopisecké články MeSH
Coumarin (2H-1-benzopyran-2-one) is a phenolic compound derived from the shikimate pathway and synthesized by various medicinal and aromatic plants as parent molecule of a large group of secondary metabolites, namely coumarins. Its main utilization is as fixative in perfumes and flavour enhancer. Given its role as phytoalexin and phagodepression activity, herein we evaluated for the first time its efficacy against several insect species: the green peach aphid, Myzus persicae, the moth Spodoptera littoralis, the housefly, Musca domestica and the filariasis vector Culex quinquefasciatus. Two non-target species were also included in our toxicity evaluation experiments: the ladybug Harmonia axyridis and the earthworm Eisenia fetida. Results highlighted remarkable selectivity of coumarin, being highly toxic to M. persicae aphids (LC50(90) values of 1.3(1.9) mg L-1) and friendly to natural enemies of aphids as well as soil invertebrates.
- MeSH
- Culex účinky léků MeSH
- inhibiční koncentrace 50 MeSH
- insekticidy toxicita MeSH
- kumariny toxicita MeSH
- larva účinky léků MeSH
- moucha domácí účinky léků MeSH
- mšice účinky léků MeSH
- můry účinky léků MeSH
- rostlinné extrakty chemie MeSH
- semena rostlinná chemie MeSH
- Spodoptera účinky léků MeSH
- testy toxicity MeSH
- zvířata MeSH
- Check Tag
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
Four unprecedented acetylenic alcohols, (Z)-non-7-en-5-yn-1,2,4-triol (1), (Z)-non-7-en-5-yn-1,4-diol (2), (Z)-1,2-dihydroxynon-7-en-5-yn-4-one (3), and (Z)-1-hydroxynon-7-en-5-yn-4-one (4) were isolated from the poisonous mushroom Tricholoma pardinum (Agaricales, Basidiomycota), together with the known compounds 1H-indole-3-carbaldehyde (5) and 6-hydroxy-1H-indole-3-carbaldehyde (6). Their structures were determined by NMR and IR spectroscopy, and mass spectrometry. The crude acetone extract of the mushroom showed potent anti-arthropod activity against Tetranychus urticae (Acarinae), a dangerous crop pest.[Figure: see text].
Carlina acaulis (Compositae) is traditionally used for food and medicinal purposes in central and southern Europe. Its root essential oil (EO), mainly composed by carlina oxide, is included in the BELFRIT botanical list of food supplements. It is also recognized as a potent mosquito larvicide. It is matter of concern whether this EO could be endowed with intrinsic toxicity to limit its use on a food level. Focusing on the insecticidal activity of this EO, we investigated the acute toxicity and sublethal effects on Musca domestica. In topical assays, the EO was extremely effective (LD50 = 2.74 and 5.96 μg fly-1, on males and females, respectively). The exposure to a sublethal dose (LD30) led to significant reductions of female longevity (LT50 = 6.7-9.0 days vs. control LT50 = 12.9-13.7 days). Treated females laid 2.5 times fewer eggs over control ones. F1 vitality decreased: F1 larvae and pupae showed high mortality, 2-4-fold higher over the control. The EO also showed high cytotoxicity on normal human fibroblasts (NHF-A12, IC50 = 9.4-14.2 μg mL-1 after 6-48 h). Overall, our findings support the employ of this EO for developing botanical insecticides. At the same time, they encourage food safety authorities to perform a full toxicological assessment for possible restrictions at food level.
- MeSH
- buněčné linie MeSH
- insekticidy toxicita MeSH
- kořeny rostlin chemie MeSH
- kukla účinky léků MeSH
- larva účinky léků MeSH
- lidé MeSH
- Magnoliopsida chemie MeSH
- moucha domácí účinky léků MeSH
- oleje prchavé toxicita MeSH
- oleje rostlin toxicita MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- mužské pohlaví MeSH
- ženské pohlaví MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
ETHNOPHARMACOLOGICAL RELEVANCE: The use of Hazomalania voyronii, popularly known as hazomalana, to repel mosquitoes and resist against insect attacks is handed down from generation to generation in Madagascar. In the present study, we investigated the ability of the essential oils (EOs) obtained from the stem wood, fresh and dry bark of H. voyronii to keep important mosquito vectors (Aedes aegypti and Culex quinquefasciatus) away, as well as their toxicity on three insect species of agricultural and public health importance (Cx. quinquefasciatus, Musca domestica and Spodoptera littoralis). MATERIALS AND METHODS: Hydrodistillation was used to obtain EOs from stem wood, fresh and dry bark. The chemical compositions were achieved by gas chromatography-mass spectrometry (GC-MS). Toxicity assays using stem wood and bark EOs were performed on larvae of Cx. quinquefasciatus and S. littoralis, and adults of M. domestica by WHO and topical application methods, respectively. Mosquito repellent activity of the most effective EO, i.e. the bark one, was determined on human volunteers by arm-in-cage tests, and results were compared with that of the commercial repellent N,N-ddiethyl-m-toluamide (DEET). RESULTS: The H. voyronii EOs were characterized by oxygenated monoterpenes with perilla aldehyde (30.9-47.9%) and 1,8-cineole (19.7-33.2%) as the main constituents. The fresh and dry bark EOs were the most active on Cx. quinquefasciatus and S. littoralis larvae, respectively, with LC50/LD50 of 65.5 mg L-1, and 50.5 μg larva-1; the EOs from wood and fresh bark displayed the highest toxicity on M. domestica (LD50 values 60.8 and 65.8 μg adult-1, respectively). Repellence assay revealed an almost complete protection (>80%) from both mosquito species for 30 min when pure fresh bark EO was applied on the volunteers' arm, while DEET 10% repelled >80% of the mosquitoes up to 120 min from application. CONCLUSION: The traditional use of the bark EO to repel insects has been demonstrated although an extended-release formulation based on H. voyronii EOs is needed to increase the repellent effect over time. A wide spectrum of insecticidal activity has been provided as well, suggesting a possible use of H. voyronii EOs in the fabrication of green repellents and insecticides useful to control mosquito vectors and agricultural pests.
- MeSH
- Aedes účinky léků růst a vývoj MeSH
- časové faktory MeSH
- Culex účinky léků embryologie MeSH
- diethyltoluamid farmakologie MeSH
- dřevo * chemie MeSH
- Hernandiaceae * chemie MeSH
- kůra rostlin * chemie MeSH
- larva účinky léků růst a vývoj MeSH
- lidé MeSH
- moskyti - kontrola * MeSH
- moucha domácí účinky léků růst a vývoj MeSH
- oleje prchavé izolace a purifikace farmakologie MeSH
- oleje rostlin izolace a purifikace farmakologie MeSH
- repelenty proti hmyzu izolace a purifikace farmakologie MeSH
- Spodoptera účinky léků embryologie MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- srovnávací studie MeSH
Medicinal and aromatic plants represent an outstanding source of green active ingredients for a broad range of real-world applications. In the present study, we investigated the insecticidal potential of the essential oils obtained from three medicinal and aromatic plants of economic importance in Algeria, Artemisia campestris, Pulicaria arabica, and Saccocalyx satureioides. Gas chromatography coupled with mass spectrometry (GC-MS) was used to study the essential oil chemical compositions. The three essential oils were tested against a mosquito vectoring filariasis and arboviruses, i.e., Culex quinquefasciatus, a fly pest acting also as pathogens vector, Musca domestica, and an agricultural moth pest, i.e., Spodoptera littoralis, using WHO and topical application methods, respectively. The essential oil from A. campestris, containing β-pinene (15.2%), α-pinene (11.2%), myrcene (10.3%), germacrene D (9.0%) (Z)-β-ocimene (8.1%) and γ-curcumene (6.4%), showed remarkable toxicity against C. quinquefasciatus (LC50 of 45.8 mg L-1) and moderate effects (LD50 of 99.8 μg adult-1) against M. domestica. Those from P. arabica and S. satureioides, containing epi-α-cadinol (23.9%), δ-cadinene (21.1%), α-cadinol (19.8%) and germacrene D-4-ol (8.4%), and thymol (25.6%), α-terpineol (24.6%), borneol (17.4%) and p-cymene (11.4%), respectively, were more active on S. littoralis showing LD50 values of 68.9 and 61.2 μg larva-1, respectively. Based on our results, the essential oil from A. campestris may be further considered a candidate ingredient for developing botanical larvicides.
- MeSH
- Culex * MeSH
- insekticidy * MeSH
- larva MeSH
- léčivé rostliny * MeSH
- oleje prchavé * MeSH
- pelyněk * MeSH
- Pulicaria * MeSH
- zvířata MeSH
- Check Tag
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Geografické názvy
- Alžírsko MeSH
Echinophora spinosa (Apiaceae) is a psammophilous species growing along Mediterranean coastal sand dunes. This species secretes essential oils made up of monoterpenoids, phenylpropanoids, and polyacetylenes, which may represent effective, eco-friendly and safe active ingredients for the preparation of green insecticides. Based on this, in the present study, we selected a French accession of E. spinosa growing on the coastal dunes of Corsica, extracting the essential oils from aerial parts and roots by hydrodistillation. The essential oils were analyzed by GC-MS for chemical composition and screened for their insecticidal activity on three target insects, Culex quinquefasciatus, Spodoptera littoralis, and Musca domestica. The essential oil from roots was dominated by the phenylpropanoid myristicin and the monoterpene hydrocarbon terpinolene, with a minor contribution of (Z)-falcarinol. The oil from the aerial parts was characterized by monoterpenes, mainly p-cymene, a-phellandrene, and α-pinene. The root essential oil exhibited promising toxicity on the target insects, with special reference to C. quinquefasciatus larvae (LC50 = 15.7 mg L-1), while on M. domestica and S. littoralis, it showed LD50 of 38.3 μg adult-1 and 55.6 μg larva-1, respectively. Based on our findings, E. spinosa can be viewed as a new potential crop to produce insecticidal essential oils in arid salty areas. However, synergistic and antagonistic effects of the major constituents of both oils tested here deserve future research. Further studies on the efficacy of stable formulations of the E. spinosa root essential oil, with special reference to micro- and nanoformulations, are ongoing.
- MeSH
- Apiaceae * MeSH
- halotolerantní rostliny MeSH
- insekticidy * MeSH
- larva MeSH
- monoterpeny MeSH
- oleje prchavé * MeSH
- ostrovy MeSH
- zvířata MeSH
- Check Tag
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Geografické názvy
- Francie MeSH
- ostrovy MeSH
Since time immemorial, the oleo-gum-resins of Ferula assa-foetida and F. gummosa are used in the traditional medical systems as well as in foodstuffs, perfumery and cosmetics. In the present study, we explored the insecticidal efficacy of the essential oils obtained from these oleo-gum-resins to widen their fields of industrial applications. The two essential oils were mainly composed of sulfides [sec-butyl (Z)-propenyl disulfide, sec-butyl (E)-propenyl disulfide, sec-butyl (Z)-propenyl trisulfide and sec-butyl (E)-propenyl trisulfide)] and monoterpenes (α-pinene, β-pinene and β-phellandrene), respectively, as determined by GC-MS analysis. The two essential oils were assayed for toxicity on a panel of insects, represented by species of public health relevance (Culex quinquefasciatus and Musca domestica), agricultural (Spodoptera littoralis) and stored-product pests (Prostephanus truncatus and Trogoderma granarium). The ecotoxicological effects of the essential oils were assessed on the aquatic microcrustacean Daphnia magna and the earthworm Eisenia fetida, as well as on human cells. Overall, the two essential oils were effective against important insect pests and vectors. On the other hand, they resulted cytotoxic to fibroblasts and non-target aquatic microcrustaceans. Thus, further insights are needed to determine the full spectrum of their eco-toxicological effects.
- MeSH
- Ferula chemie MeSH
- hmyz účinky léků MeSH
- insekticidy farmakologie toxicita MeSH
- oleje prchavé farmakologie toxicita MeSH
- oleje rostlin farmakologie toxicita MeSH
- plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
- zvířata MeSH
- Check Tag
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
Thymus alternans and Teucrium montanum subsp. jailae are medicinal and aromatic plants, typical of Slovakian flora, producing bioactive essential oils. In the present study, we evaluated the insecticidal potential of the essential oils, obtained by hydrodistillation from the plant aerial parts and analysed by GC-MS, as insecticidal agents. For the purpose, they were assayed against three insect species acting as agricultural pests or vectors of medical relevance, such as the common housefly, Musca domestica L., the lymphatic filariasis vector, Culex quinquefasciatus and the Egyptian cotton leafworm Spodoptera littoralis; α-cypermethrin was tested as positive control. The two essential oils exhibited a different chemical profile, with monoterpenes and sesquiterpenes being the main fractions in the essential oils from Th. alternans and T. montanum subsp. jailae, respectively. Insecticidal tests showed that the T. montanum essential oil was effective against S. littoralis (LD50(90) = 56.7 (170.0) μg larva-1) and Cx. quinquefasciatus larvae (LC50(90) = 180.5 (268.7) mg L-1), whereas T. alternans essential oil displayed good toxicity against M. domestica adults (LD50(90) = 103.7 (223.9) μg adult-1). Overall, our results add useful knowledge about the potential of Slovakian flora as a source of botanicals for the eco-friendly management of insect pests and vectors.
- MeSH
- Culex účinky léků metabolismus MeSH
- insekticidy analýza farmakologie MeSH
- larva účinky léků metabolismus MeSH
- léčivé rostliny chemie MeSH
- monoterpeny analýza farmakologie MeSH
- moucha domácí účinky léků metabolismus MeSH
- oleje prchavé analýza farmakologie MeSH
- ožanka chemie MeSH
- plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
- pyrethriny analýza farmakologie MeSH
- seskviterpeny analýza farmakologie MeSH
- Spodoptera účinky léků metabolismus MeSH
- Thymus (rostlina) chemie MeSH
- zvířata MeSH
- Check Tag
- ženské pohlaví MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Geografické názvy
- Slovenská republika MeSH
