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Item Corymbia spp. and Eucalyptus spp. essential oils have insecticidal activity against Plutella xylostella(Industrial Crops and Products, 2017-12-15) Filomeno, Claudinei Andrade; Barbosa, Luiz Claudio Almeida; Teixeira, Robson Ricardo; Pinheiro, Antônio Lelis; Farias, Elizeu de Sá; Silva, Eliete Meire de Paula; Picanço, Marcelo CoutinhoPlutella xylostella (L.) is the main brassica pest worldwide and is difficult to control even with commercial insecticides. In this study, assessments were made of the contact toxicity of essential oils (EOs) from ten Myrtaceae species. For this, the leaves of four Corymbia species (C. citriodora, C. intermedia, C. maculata, and C. ptychocarpa) and six Eucalyptus species (E. andrewsii, E. crebra, E. punctata, E. pyrocarpa, E. siderophloia, and E. sphaerocarpa) were collected during the Brazilian dry season and subjected to hydrodistillation for extraction of EOs. For C. citriodora, another sample was also collected during the rainy season. The essential oil (EO) content of all samples ranged from 0.07% w/w to 3.3% w/w and GC–MS analyses allowed the identification of 52 compounds. For E. andrewsii, E. pyrocarpa, and C. ptychocarpa there was no previous report on EO chemical composition. For C. citriodora, a higher EO content for the samples collected during the dry season was found (2.72% versus 1.53% for the rainy season). The insecticidal activity of all eleven EOs was evaluated via topical application on the second-instar larvae of P. xylostella. The most active EOs were produced by C. citriodora collected during the dry season, with citronellal (86.8%) and isopulegol (4.7%) being the main constituents. At 30 μg/mg of insect, these EOs caused 80% P. xylostella mortality, being more active than neem oil used as positive control. These EOs presented low toxicity for Solenopsis saevissima, a natural predator of P. xylostella. Bioassays also demonstrated a synergistic effect between citronellal and (-)-isopulegol at all tested proportions. The results described here suggest that C. citriodora EOs can be an environmentally friendly alternative method to control P. xylostella.Item An optimized and validated 1H NMR method for the quantification of α-pinene in essentials oils(Talanta, 2015-10-31) Cerceau, Cristiane I.; Barbosa, Luiz C.A.; Filomeno, Claudinei A.; Alvarenga, Elson S.; Demuner, Antônio J.; Fidencio, Paulo H.The authenticity and composition of commercial essential oils requires strict quality control. Due to the importance of α-pinene containing essential oils, a rapid and efficient method for quantification of this terpene in oils of eucalyptus, pink pepper and turpentine using 1H NMR was developed and validated. All evaluated parameters (selectivity, linearity, accuracy/precision, repeatability, robustness, stability of analyte and internal standard in solutions) showed satisfactory results. The limit of detection (LOD) and limit of quantification (LOQ) were 0.1 and 2.5 mg respectively. These values indicated that α-pinene was detected in 35 mg samples containing at least 0.3% of this compound. In addition, a minimum of 8% of α-pinene in the sample was required for quantification. Furthermore, the standard deviations found in the 1H NMR methodology were less than 1% and were lower than those obtained by gas chromatographic analysis. Statistical tests have shown that the results obtained by 1H NMR methodology are similar to those obtained by GC-FID technique using external and internal standardization and normalization within 95% confidence. R&R values lower than 10% have shown that all the methods are appropriate and the 1H NMR method is suitable for quantification of α-pinene in samples of essential oils since this method possessed the smallest R&R (1.81) value.Item A validated 1 H NMR method for quantitative analysis of α -bisabolol in essential oils of Eremanthus erythropappus(Talanta, 2016-08-10) Cerceau, Cristiane I.; Barbosa, Luiz C.A.; Alvarenga, Elson S.; Ferreira, Antonio G.; Thomasi, Sérgio S.α-Bisabolol is a natural terpene produced by Eremanthus erythropappus and is widely used in cosmetics and pharmaceuticals due to its anti-inflammatory, antibacterial and antimycotic properties. Due to these applications, a control of composition and authenticity of commercial oils rich in this terpene is required, resulting in a demand for new methodologies for quality control. In this work a rapid and efficient method for quantification of α-bisabolol in the essential oil of E. erythropappus (candeia) using 1H NMR was developed, validated and compared to gas chromatography (GC) method. The quantification of α-bisabolol by 1H NMR was successfully achieved for most of the essential oil samples of E. erythropappus evaluated, except for those with a more complex composition. To circumvent this limitation a 2D NMR COSY contour map was used. This method proved to be a fast and efficient alternative, providing results with standard deviations SD<0.3%. All evaluated parameters (selectivity, linearity, accuracy/precision, repeatability, robustness and stability of analyte and internal standard in solution) gave satisfactory results. Using the 1H NMR signals at 5.36 and 5.13 ppm, the limit of detection (LOD) and limit of quantification (LOQ) were 0.26 and 2.59 mg, respectively. The results obtained by the 1H NMR method presented SD=0.59%, smaller than the value found for GC (SD=1.18%). Tukey tests have shown that the results obtained by 1H NMR and COSY methodology are similar to the obtained by the traditional GC-FID technique using external and internal standardization and normalization with 95% confidence.Item Chemical composition and histochemistry of Sphagneticola trilobata essential oil(Revista Brasileira de Farmacognosia, 2012-01-17) Silva, Cleber José da; Barbosa, Luiz C. A.; Demuner, Antonio J.; Montanari, Ricardo M.; Francino, Dayana; Meira, Renata M. S. A.; Souza, Ana Olívia deAnatomical and histochemical investigations of Sphagneticola trilobata (L.) Pruski, Asteraceae, secretory structures in leaves and stems and the seasonal variation of essential oils were carried out. Histochemical techniques enabled the specific location of the essential oil accumulation in the internal (canals) and external structures (trichomes). Histochemical analysis showed that the secretory trichomes produced steroids. The highest yield was obtained from plants collected in winter, when it was registered low temperature and precipitation. The essential oil was characterized by high percentage of hydrocarbon sesquiterpenes, hydrocarbon monoterpenes and low levels of oxygenated sesquiterpenes. The major components were germacrene D (11.9-35.8%), α-phellandrene (1.4-28.5%), α-pinene (7.3-23.8%), E-caryophyllene (4.6-19.0%), bicyclogermacrene (6.0-17.0%), limonene (1.8-15.1%) and α-humulene (4.0-11.6%). The percentage of most of the individual constituents present in S. trilobata essential oil changed significantly during the months.Item Assessing the chemical composition and antimicrobial activity of essential oils from Brazilian plants—Eremanthus erythropappus (Asteraceae), Plectrantuns barbatus, and P. amboinicus (Lamiaceae)(Molecules, 2015-05-11) Santos, Nara O. dos; Mariane, Bruna; Lago, João Henrique G.; Sartorelli, Patricia; Rosa, Welton; Soares, Marisi G.; Silva, Adalberto M. da; Lorenzi, Harri; Vallim, Marcelo A.; Pascon, Renata C.The chemical composition and antimicrobial activity of essential oils obtained from three Brazilian plant species—leaves and branches of Eremanthus erythropappus (Asteraceae), leaves of Plectranthus barbatus, and leaves of P. amboinicus (Lamiaceae)—were determined. Analysis by GC/MS and determination of Kovats indexes both indicated δ-elemene (leaves—42.61% and branches—23.41%) as well as (−)-α-bisabolol (leaves—24.80% and stem bark—66.16%) as major constituents of E. erythropappus essential oils. The main components of leaves of P. barbatus were identified as (Z)-caryophyllene (17.98%), germacrene D (17.35%), and viridiflorol (14.13%); whereas those of leaves of P. amboinicus were characterized as p-cymene (12.01%), γ-terpinene (14.74%), carvacrol (37.70%), and (Z)-caryophyllene (14.07%). The antimicrobial activity against yeasts and bacteria was assessed in broth microdilution assays to determine the minimum inhibitory concentration (MIC) necessary to inhibit microbial growth. In addition, the crude oil of branches of E. erythropappus was subjected to chromatographic separation procedures to afford purified (−)-α-bisabolol. This compound displayed biological activity against pathogenic yeasts, thus suggesting that the antimicrobial effect observed with crude oils of E. erythropappus leaves and branches may be related to the occurrence of (−)-α-bisabolol as their main component. Our results showed that crude oils of Brazilian plants, specifically E. erythropappus, P. barbatus, and P. amboinicus and its components, could be used as a tool for the developing novel and more efficacious antimicrobial agents.Item Seasonal variation in the chemical composition and antimicrobial activity of volatile oils of three species of Leptospermum (Myrtaceae) grown in Brazil(Molecules, 2011-01-26) Demuner, Antonio Jacinto; Barbosa, Luiz Claudio Almeida; Magalhaes, Cassia Gonçalves; Silva, Cleber Jose Da; Maltha, Celia Regina Alvares; Pinheiro, Antonio LelisThis study investigates the seasonal variation of three species of Leptospermum (Myrtaceae) grown in Brazil. The chemical composition of the volatile oils of L. flavescens and L. petersonii did not show any significant seasonal variation in the major components, while for Leptospermum madidum subsp. sativum the levels of major constituents of the volatile oils varied with the harvest season. Major fluctuations in the composition of L. madidum subsp. sativum oil included α-pinene (0–15.2%), β-pinene (0.3–18.5%), α-humulene (0.8–30%), 1,8-cineole (0.4–7.1%) and E-caryophyllene (0.4–11.9%). Levels of β-pinene (0.3–5.6%), terpinen-4-ol (4.7–7.2%) and nerolidol (55.1–67.6%) fluctuated seasonally in the L. flavescens oil. In L. petersonii, changes were noted for geranial (29.8–32.8%), citronellal (26.5–33.9%) and neral (22.7–23.5%). The activity of the volatile oils against the tested bacteria differed, depending on season the oils were obtained. In general, the volatile oils were more active against Gram-positive bacteria.Item Chemical variability and biological activities of Eucalyptus spp. essential oils(Molecules, 2016-09-07) Barbosa, Luiz Claudio Almeida; Filomeno, Claudinei Andrade; Teixeira, Robson RicardoMany plant species produce mixtures of odorous and volatile compounds known as essential oils (EOs). These mixtures play important roles in Nature and have been utilized by mankind for different purposes, such as pharmaceuticals, agrochemicals, aromatherapy, and food flavorants. There are more than 3000 EOs reported in the literature, with approximately 300 in commercial use, including the EOs from Eucalyptus species. Most EOs from Eucalyptus species are rich in monoterpenes and many have found applications in pharmaceuticals, agrochemicals, food flavorants, and perfumes. Such applications are related to their diverse biological and organoleptic properties. In this study, we review the latest information concerning the chemical composition and biological activities of EOs from different species of Eucalyptus. Among the 900 species and subspecies of the Eucalyptus genus, we examined 68 species. The studies associated with these species were conducted in 27 countries. We have focused on the antimicrobial, acaricidal, insecticidal and herbicidal activities, hoping that such information will contribute to the development of research in this field. It is also intended that the information described in this study can be useful in the rationalization of the use of Eucalyptus EOs as components for pharmaceutical and agrochemical applications as well as food preservatives and flavorants. View Full-Text