Exploring Contact Toxicity of Essential Oils against Sitophilus zeamais through a Meta-Analysis Approach.

Sitophilus zeamais is a primary pest of maize. Our aim was to perform a qualitative review and meta-analyses with 56 scientific articles published from 1 January 2000 to 1 October 2022 dealing with direct (topical application) and indirect (impregnation of essential oils, EOs, onto filter paper or maize grains) contact toxicity of EOs against S. zeamais. Three independent meta-analyses of single means of LD50 (direct contact) and LC50 (indirect contact) were conducted using a random effect model. Essential oils more frequently evaluated were those belonging to Asteraceae, Apiaceae, Lamiaceae, Myrtaceae, Piperaceae, and Rutaceae. The LC50 global mean values were 33.19 µg/insect (CI95 29.81-36.95) for topical application; 0.40 µL/cm2 (CI95 0.25-0.65) for filter paper indirect contact; and 0.50 µL/g maize (CI95 0.27-0.90) for maize grains indirect contact. The species Carum carvi, Salvia umbratica, Ilicium difengpi, Periploca sepium, Cephalotaxus sinensis, Murraya exotica, Rhododendron anthopogonoides, Ruta graveolens, Eucalyptus viminalis, Ocotea odorifera, Eucalyptus globulus, Eucalyptus dunnii, Anethum graveolens, Ilicium verum, Cryptocarya alba, Azadirachta indica, Chenopodium ambrosioides, Cupressus semperivens, Schinus molle, Piper hispidinervum, Mentha longifolia, and Croton pulegiodorus showed LC50 or LD50 values lower than the global means, indicating good insecticidal properties. Our results showed that EOs have great potential to be used as bioinsecticides against S. zeamais.

Fungal diversity and mycotoxins detected in maize stored in silo-bags: a review.

Silo-bags are hermetic storage systems that inhibit fungal growth because of their atmosphere with low humidity, as well as low pH and O2 concentrations, and a high CO2 concentration. If a silo-bag with stored maize loses its hermetic nature, it favors the development of fungi and the production of mycotoxins. To the best of our knowledge, this is the first review on the diversity of fungal species and mycotoxins that were reported in maize stored under the environmental conditions provided by silo-bags. The genera Penicillium, Aspergillus and Fusarium were found more frequently, whereas Acremonium spp., Alternaria sp., Candida sp., Cladosporium sp., Debaryomyces spp., Epiconum sp., Eupenicillium spp., Eurotium sp., Eurotium amstelodami, Hyphopichia spp., Hyphopichia burtonii, Moniliella sp., Wallemia sp. and genera within the orden Mucorales were reported less recurrently. Despite finding a great fungal diversity, all of the studies focused their investigations on a small group of toxins: fumonisins (FBs), aflatoxins (AFs), deoxynivalenol (DON), zearalenone (ZEA), patulin (PAT), toxin T2 (T2) and ochratoxin (OT). Of the FBs, fumonisin B1 and fumonisin B2 presented higher incidence percentages, followed by fumonisin B3 . Of the AFs, the only one reported was aflatoxin B1. The mycotoxins DON, ZEA and OT were found with lower incidences, whereas PAT and T2 were not detected. Good management practices of the silo-bags are necessary to achieve a hermetically sealed environment, without exchange of gases and water with the external environment during the storage period. © 2022 Society of Chemical Industry.

Can Essential Oils Be a Natural Alternative for the Control of Spodoptera frugiperda? A Review of Toxicity Methods and Their Modes of Action

Spodoptera frugiperda is a major pest of maize crops. The application of synthetic insecticides and the use of Bt maize varieties are the principal strategies used for its control. However, due to the development of pesticide resistance and the negative impact of insecticides on the environment, natural alternatives are constantly being searched for. Accordingly, the objective of this review was to evaluate the use of essential oils (EOs) as natural alternatives for controlling S. frugiperda. This review article covers the composition of EOs, methods used for the evaluation of EO toxicity, EO effects, and their mode of action. Although the EOs of Ocimum basilicum, Piper marginatum, and Lippia alba are the most frequently used, Ageratum conyzoides, P. septuplinervium. O. gratissimum and Siparuna guianensis were shown to be the most effective. As the principal components of these EOs vary, then their mode of action on the pest could be different. The results of our analysis allowed us to evaluate and compare the potential of certain EOs for the control of this insect. In order to obtain comparable results when evaluating the toxicity of EOs on S. frugiperda, it is important that methodological issues are taken into account.

Cinnamaldehyde and related phenylpropanoids, natural repellents, and insecticides against Sitophilus zeamais (Motsch.). A chemical structure-bioactivity relationship.

BACKGROUND: The insecticidal and repellent effects on adult Sitophilus zeamais of 12 cinnamaldehyde-related compounds was evaluated by contact toxicity bioassays and a two-choice olfactometer. To determine non-toxicity in mammals, body weight, serum biochemical profiles, liver weight, physiological parameters, sperm motility, and histopathological data were obtained as complementary information in C57BL/6 mice treated with the best natural compound. RESULTS: Based on 24 h LC95 and LC50 values, α-methyl-cinnamaldehyde and cinnamaldehyde exhibited better insecticidal action than the other compounds. The best repellent effect was observed with α-bromo-cinnamaldehyde, which even repelled at the lowest concentration studied (0.28 µmol L-1 ). The evaluation of a quantitative structure-activity relationship found a linear relationship between the LC50 values for adult weevil toxicity and dipolo with Q values (giving the difference between orbital electronegativity carbon 1 and orbital electronegativity carbon 3 of the molecule) in cinnamaldehyde-related compounds. The polar surface and Log P descriptors also revealed a linear relationship with the S. zeamais repellent effect for cinnamaldehyde analogues. Cinnamaldehyde did not show toxicity in the parameters evaluated in mice. CONCLUSION: From the phenylpropanoid components studied, the natural compound that had the best insecticidal and repellent action against S. zeamais was cinnamaldehyde. It presented no mammalian toxicity. © 2018 Society of Chemical Industry.

Thymol feed supplementation in quail alters the percentages of nutritionally relevant egg yolk fatty acids: effects throughout incubation.

BACKGROUND: Polyunsaturated fatty acids (PUFA) are crucial components of egg yolk and particularly prone to oxidative damage, generating losses of nutrients for embryonic development and influencing the quality of eggs for human consumption. The aim of this study was to evaluate whether dietary thymol (a natural antioxidant) is related to changes in quail egg yolk total (T), triglyceride (TG) and phospholipid (PL) fatty acid composition at different stages of embryo development. Thus female Japanese quail (100 days of age) were assigned to one of two dietary treatments (12 individuals each): CON (basal diet) or THY (0.0016 mol thymol day-1 per bird). After 2 weeks of supplementation, eggs were incubated and samples were obtained at 0, 4 and 16 days of embryonic development. RESULTS: In 0 day THY eggs, α-linolenic acid and n-3 PUFA in T and TG, docosahexaenoic acid and PUFA in T and arachidonic acid in TG were increased, while saturated fatty acids (SFA) in T were reduced. From 4 days on, PUFA, n-3 PUFA and SFA from T and TG in THY eggs were found to be similar to those of CON eggs. The changes in PL throughout incubation were similar in both dietary treatments. CONCLUSION: Thymol would provide the embryo with PUFA for synthesis/deposition in membranes and/or assign to supply energy. Additionally, thymol supplementation would be advisable for the production of healthier table eggs. © 2017 Society of Chemical Industry.

Effect of Selected Volatiles on Two Stored Pests: The Fungus Fusarium verticillioides and the Maize Weevil Sithophilus zeamais.

New agronomic practices and technology enabled Argentina a larger production of cereal grains, reaching a harvest yield of 26.5 million metric tons of maize, of which, about 40% was exported. However, much of the maize production is lost annually by the attack of fungi and insects (2.6 million tons). In this study, the antifungal effect of selected volatiles on Fusarium verticillioides, its mycotoxin production, and the repellent and insecticidal activities against the weevill Sithophilus zeamais, an insect vector of F. verticillioides, were evaluated. The compounds tested were (2E)-2-hexenal, (2E)-2-nonenal, (2E,6Z)-2,6-nonadienal, 1-pentanol, 1-hexanol, 1-butanol, 3-methyl-1-butanol, pentanal, 2-decanone, and 3-decanone, which occur in the blend of volatile compounds emitted by various cereal grains. The most active antifungals were the aldehydes (2E)-2-nonenal, (2E)-2-hexenal, and (2E,6Z)-2,6-nonadienal (minimum inhibitory concentration values of <0.03, 0.06, and 0.06 mM, respectively). The occurrence of fumonisin B1 also was prevented because these compounds completely inhibited fungal growth. The best insecticidal fumigant activities against the maize weevil were shown by 2-decanone and 3-decanone (lethal concentration ≤ 54.6 µL/L (<0.28 mM)). Although, all tested compounds showed repellent activity against S. zeamais at a concentration of 4 µL/L, (2E,6Z)-2,6-nonadienal was the most active repellent compound. These results demonstrate the potential of (2E,6Z)-2,6-nonadienal to be used as a natural alternative to synthetic pesticides on F. verticillioides and S. zeamais.

Bioactivities of Ketones Terpenes: Antifungal Effect on F. verticillioides and Repellents to Control Insect Fungal Vector, S. zeamais.

Maize is one the most important staple foods in the world. However, numerous pests, such as fungal pathogens, e.g., Fusarium verticillioides, and insects, such as Sitophlilus zeamais, attack maize grains during storage. Many F. verticillioides strains produce fumonisins, one of the most important mycotoxin that causes toxic effects on human and animal health. This situation is aggravated by the insect fungal vector, Sitophlilus zeamais, which contributes to the dispersal of fungal spores, and through feeding damage, provide entry points for fungal infections. The aim of this study was to evaluate in vitro bioassays, the antifungal activity on F. verticillioides M3125 and repellent effects against S. zeamais of ketone terpenes. In addition, we performed Quantitative structure-activity relationship (Q-SAR) studies between physico-chemical properties of ketone terpenes and the antifungal effect. Thymoquinone was the most active compound against F. verticillioides (Minimum Inhibitory Concentration, MIC: 0.87) affecting the lag phase and the growth rate showing a total inhibition of growth at concentration higher than 2 mM (p < 0.05). The Q-SAR model revealed that the antifungal activity of ketone compounds is related to the electronic descriptor, Pi energy. Thymoquinone showed a strong repellent effect (-77.8 ± 8.5, p < 0.001) against S. zeamais. These findings make an important contribution to the search for new compounds to control two stored pests of maize.

Bio-efficacy of the essential oil of oregano (Origanum vulgare Lamiaceae. Ssp. Hirtum).

The aim of this study was to investigate the bioactivity of the essential oil isolated from Origanum vulgare L. (EOv). We analyzed the in vivo anti-inflammatory properties in a mouse-airway inflammation model and the in vitro antimicrobial activity, genotoxicity over the anaphase-telophase with the Allium cepa strain and its cytotoxicity/viability in A549 culture cells. In vivo, EOv modified the levels of tumor necrosis factor -α and viable activated macrophages and was capable to mitigate the effects of degradation of conjugated dienes. In vitro, EOv reduced the viability of cultured A549 cells as well as the mitotic index and a number of chromosomal aberrations; however, it did not change the number of phases. We found that EOv presents antimicrobial activity against different Gram (-) and (+) strains, measured by disc-diffusion test and confirmed with a more accurate method, the AutoCad software. We postulate that EOv presents antibacterial, antioxidant and chemopreventive properties and could be play an important role as bioprotector agent.

Effect of peanut skin extract on chemical stability and sensory properties of salami during storage.

BACKGROUND: Peanut skin extracts (PSEs) have proven antioxidant properties in different food products. The objective of this study was to evaluate the effect of peanut skin extract as natural preserving compounds on chemical stability and sensory properties of salami during storage. RESULTS: PSE was obtained with ethanol-water and added during the preparation of salami samples. Raw salami samples were cured and stored at 15 °C and 65% relative humidity. Moisture, peroxide value, conjugated dienes, free fatty acids and sensory descriptive attributes were evaluated on the samples. Peroxide values increased during storage in all samples and were 82.9 in control (salami without additives), 18.0 in salami with 0.2 g kg(-1) PSE (E0.02), 13.0 in salami with 1.0 g kg(-1) PSE (E0.1), and 0.63 meqO2 kg(-1) in salami with butylated hydroxytoluene (BHT) after 42 days of storage. BHT and E0.1 treatments resulted in a lower increase in the intensity of oxidized flavor and a lower decrease in the intensity of salami flavor. CONCLUSION: Chemical indicators and descriptive results indicated that PSE retards lipid oxidation and preserves sensory properties of salami, prolonging its shelf life.

Chemical compositions and properties of Schinus areira L. essential oil on airway inflammation and cardiovascular system of mice and rabbits.

The main purpose was to investigate the effects of essential plant-oil of Schinus areira L. on hemodynamic functions in rabbits, as well as myocardial contractile strength and airways inflammation associated to bacterial endotoxin lipopolysaccharide (LPS) in mice. This study shows the important properties of the essential oil (EO) of S. areira studied and these actions on lung with significant inhibition associated to LPS, all of which was assessed in mice bronchoalveolar lavage fluid and evidenced by stability of the percentage of alveolar macrophages, infiltration of polymorphonuclear leukocytes and tumor necrosis factor-α concentration, and without pathway modifications in conjugated dienes activity. Clinical status (morbidity or mortality), macroscopic morphology and lung/body weight index were unaffected by the administration of the EO S. areira. Furthermore, the ex vivo analysis of isolated hearts demonstrated the negative inotropic action of the EO of S. areira in a mice model, and in rabbits changes in the hemodynamic parameters, such as a reduction of systolic blood pressure. We conclude that EO S. areira could be responsible for modifications on the cardiovascular and/or airway parameters.

Insecticidal activity of three essential oils against two new important soybean pests: Sternechus pinguis (Fabricius) and Rhyssomatus subtilis Fiedler (Coleoptera: Curculionidae) / Actividad insecticida de tres aceites esenciales contra dos nuevas plagas importantes de la soja: Sternechus pinguis (Fabricius) y Rhyssomatus subtilis Fiedler (Coleoptera: Curculionidae)

In the present study, the essential oils from Eucalyptus globulus Labill., Citrus sinensis L. Osbeck and Citrus limon L. were analysed by GC-MS (gas chromatography–mass spectrometry) and evaluated for their toxic effects on Sternechus subsignatus and Rhyssomatus subtilis, two important pest of soybean in South America. Contact toxicity assayed by impregnation on filter paper discs showed that these oils caused significant mortality of the test insects (100 percent of mortality at 5 uL/cm2). Eucalyptus oil (98.9 percent of 1,8-cineole) had the greatest contact toxicity (LD50 = 0.40 and 0.84 uL/cm2 for S. pinguis and R. subtilis, respectively), whereas orange (87.6 percent of limonene) and lemon oils (62.5 and 12.6 percent of limonenen and beta pinene, respectively) were less toxic (LD50 > 1 uL/cm2 for both insects). All the responses were found dose-dependent. Rhyssomatus subtilis was more resistant than Sternechus pinguis to the toxicity of the essential oils studied.

En el presente estudio se analizaron por CG-EM (cromatografía de gases-espectrometría de masas) los aceites esenciales de eucalipto (Eucalyptus globulus Labill.), naranja (Citrus sinensis L. Osbeck) y limón (Citrus limon L) y se evaluaron sus efectos tóxicos contra dos especies de plagas importantes para la soja en Sud América: Sternechus subsignatus y Rhyssomatus subtilis. La toxicidad por contacto, ensayada por discos de papel de filtro impregnados, mostró que estos aceites causaron una mortalidad significativa de los insectos testeados (100 por ciento de mortalidad a 5 uL/cm2). El aceite de eucalipto (98.9 por ciento de 1,8-cineol) presentó la mayor toxicidad por contacto (LD50 = 0.40 y 0.84 uL/cm2 para S. pinguis y R. subtilis, respectivamente), mientras que el aceite de naranja (87.6 por ciento de limoneno) y el de limón (62.5 y 12.6 por ciento de limoneno y beta pineno, respectivamente) fueron menos tóxicos (LD50 > 1 uL/cm2 para ambos insectos). Todas las respuestas fueron dosis dependiente. Rhyssomatus subtilis fue más resistente que Sternechus pinguis a la toxicidad de los aceites esenciales estudiados.

Stereoselective effects of monoterpenes on the microviscosity and curvature of model membranes assessed by DPH steady-state fluorescence anisotropy and light scattering analysis.

Here, we evaluated stereoselectivity in monoterpenes (MTs) ability to disturb membrane dynamics. Correlations between molecular structure and physicochemical properties of pinenes, menthols, and carvones enantiomers were investigated through cluster and principal component analysis. Therefore, MTs' concentration-dependent changes in light scattering and diphenylhexatriene (DPH) fluorescence polarization induced by MTs were measured on large unilamellar vesicles (LUVs) of dipalmitoylphosphatidylcholine. The behavior of the less polar compounds (hydrocarbons) was characterized by a membrane expansion (increase in light scattering), detectable within the low-concentration range. They remained in the membrane up to the highest concentrations tested exhibiting a concentration-dependent anisotropy decrease. Within the more polar terpenes (alcohols) prevailed a budding phenomenon with the production of small LUVs with roughly constant curvature (more evident at medium and high concentrations), which explains the slight change in microviscosity (DPH fluorescence anisotropy). These behaviors were compatible with the deeper localization within the membrane core of the formers compared with the latters as predicted from the corresponding polar charge distribution in their molecular structures. The enantioselectivity was expressed by neomenthol at low concentration and carvone at medium concentration. Inhibition and potentiation were evidenced, within the low-concentration range, by the racemic mixtures in neomenthol and ß-pinenes, respectively.

Actividad antifúngica del aceite esencial de cinco especies de Juniperus de Argentina / Antifungal activities of the essential oil of five species of Juniperus from Argentina

The chemical composition of the leaf oils of five Juniperus species (Juniperus sabina L., Juniperus communis Lam., Juniperus scopulorum Sarg., Juniperus virginiana L., Juniperus chinensis L., Cupressaceae) was determined by co-chromatography with authentic samples, GC-MS and Kováts retention indices. Sabinene was the most abundant component in the oils of Juniperus from western Patagonia Argentina. However, limonene and germacrene B constituted 25.1 percent and 11.5 percent of the oil of J. sabina. J. virginiana showed high concentration of alpha-humulene and limonene (31.4 and 15.9 percent respectively), while isobornyl acetate and germacrene B were also the main compounds of J. chinensis. Essential oils extracted of Juniperus were evaluated in vitro for their efficacy against Fusarium verticillioides, Aspergillus flavus, Aspergillus parasiticus, Candida albicans and Rhodotorula infection. Candida albicans was not inhibited for the essential oils of Juniperus. However, F. verticillioides, A. flavus, A. parasiticus and Rhodotorula were inhibited for these oils.

La composición de los aceites esenciales de la hoja de cinco especies de Juniperus (Juniperus sabina L., Juniperus communis Lam., Juniperus scopulorum Sarg., Juniperus virginiana L., Juniperus chinensis L., Cupressaceae), se determinó mediante una co-cromatografía con muestras auténticas de dos columnas de diferente polaridad, CG-EM y los índices de retención de Kovats. El sabineno fue el componente más abundante en los aceites de Juniperus del oeste de la Patagonia Argentina. Sin embargo, el limoneno y el germacreno B son otros componentes importantes del aceite esencial de J. sabina con el 25,1 por ciento y 11,5 por ciento respectivamente. En J. virginiana el alfa-humuleno y el limoneno (con el 31,4 por ciento y 15.9 por ciento respectivamente) mostraron ser también importantes, mientras que el acetato de isobornilo y el germacreno B fueron también los principales componentes de la J. chinensis. Los aceites esenciales extraídos de Juniperus se evaluaron in vitro para determinar su eficacia contra Fusarium verticillioides, Aspergillus flavus, Aspergillus parasiticus, Candida albicans y Rhodotorula. Candida albicans no se inhibió por la acción de los aceites esenciales de Juniperus. Sin embargo, F. verticillioides, A. flavus, A. parasiticus y Rhodotorula fueron inhibidos.

Total phenolic content, radical scavenging properties, and essential oil composition of Origanum species from different populations.

The aim of this work was to compare the antiradical activity, total phenol content (TPC), and essential oil composition of Origanum vulgare spp. virens, Origanum x applii, Origanum x majoricum, and O. vulgare spp. vulgare cultivated in Argentina in different localities. The experiment was conducted in the research station of La Consulta (INTA-Mendoza), the research station of Santa Lucia (INTA-San Juan), and Agronomy Faculty of National University of La Pampa, from 2007 to 2008. The composition of the essential oils of oregano populations was independent of cultivation conditions. In total, 39 compounds were identified in essential oils of oregano from Argentina by means of GC-MS. Thymol and trans-sabinene hydrate were the most prominent compounds, followed by gamma-terpinene, terpinen-4-ol, and alpha-terpinene. O. vulgare vulgare is the only Origanum studied which is rich in gamma-terpinene. Among tested oregano, O. x majoricum showed the highest essential oil content, 3.9 mg g(-1) dry matter. The plant extract of O. x majoricum had greater total phenol content values, 19.36 mg/g dry weight, than the rest of oregano studied. To find relationships among TPC, free radical scavenging activity (FRSA), and climate variables, canonical correlations were calculated. The results obtained allow us to conclude that 70% of the TPC and FRSA variability can be explained by the climate variables (R(2) = 0.70; p = 8.3 x 10(-6)), the temperature being the most important climatic variable.

Changes in the composition of phospholipid fatty acids and sterols of maize root in response to monoterpenes.

Terpenes are thought to be important in plant plant interactions because of their phytotoxic action on seed germination and growth. Herein, the effects of five volatile monoterpenes on root sterols and phospholipid fatty acid (PLFA) composition have been studied during maize seedling germination. The investigated monoterpenes (camphor, 1-8 cineole, geraniol, menthol, and thymol) were applied at their respective IC80 (concentration causing 80% inhibition). They quantitatively affected free sterols and PLFA composition, thus producing an increase in the percentage of unsaturated PLFAs, stigmasterol of the free sterol fraction, and saturated steryl ester fatty acids. Alcoholic and nonalcoholic monoterpenes appeared to have different modes of action. The former affected unsaturated fatty acid and stigmasterol to a greater extent, and accordingly they could interfere in seedling growth by changes in the membrane lipids.

Effect of monoterpenes on lipid oxidation in maize.

The monoterpenes 1,8-cineole, thymol, geraniol, menthol and camphor strongly inhibited the root growth of Zea mays L. seedlings. They induced an oxidative stress as measured by the production of malondialdehyde, conjugated dienes and peroxides. This oxidative stress depended on the length of the exposure and on the monoterpene applied. The total fatty acid content was measured and fatty acid composition was analyzed. Unsaturated fatty acids increased in the treated samples. The alcoholic and non-alcoholic monoterpenes appeared to have different modes of action.