Insecticidal activity of essential oils on Spodoptera frugiperda and selectivity to Euborellia annulipes / Atividade inseticida de óleos essenciais sobre Spodoptera frugiperda e seletividade para Euborellia annulipes

Fall armyworm (Spodoptera frugiperda) is the main species that causes damage to the maize crop in Brazil. In the perspective of studying alternatives of control of this pest that preserve the natural enemies, the aim of this research was to evaluate the insecticidal efficiency of the essential oils of Vanillosmopsis arborea and Lippia microphylla on S. frugiperda and verify the selectivity to the predator Euborellia annulipes. The bioassays were carried out in the Agricultural Entomology Laboratory of the Federal University of Paraiba, using insects, from 3rd instar of S. frugiperda and E. annulipes, originating from mass rearing in the laboratory itself. Dilutions of the oils were performed in Tween® 80 at concentrations of 0, 100, 150 and 200 mg mL-1. 1.0 µL from each dilution was applied to the prothoracic region of the insects. The S. frugiperda mortality was verified by topical contact of V. arborea oil with LC10 = 74.3 mg mL-1 and LC50 = 172.86 mg mL-1, for L. microphyla, LC10 = 51.26 mg mL-1 and LC50 = 104.52 mg mL-1. The observed lethal concentrations for E. annulipes were V. arborea LC10 = 71.3 mg mL-1 and LC50 = 160.2 mg mL-1. While L. microphyla, were LC10 = 50.3 mg mL-1 and LC50 = 134.67 mg mL-1. The essential oils of V. arborea and L. microphylla are efficient in the control of S. frugiperda, but are not selective to the predator E. Annulipes.

A lagarta-do-cartucho (Spodoptera frugiperda) é a principal espécie que causa danos à cultura do milho no Brasil. Na perspectiva de estudar alternativas de controle desta praga que preservem os inimigos naturais, o objetivo desta pesquisa foi avaliar a eficiência inseticida dos óleos essenciais de Vanillosmopsis arborea e Lippia microphylla sobre S. frugiperda e verificar a seletividade ao predador Euborellia annulipes. Os bioensaios foram realizados no Laboratório de Entomologia Agropecuária da Universidade Federal da Paraíba, utilizando insetos, de 3º instar de S. frugiperda e E. annulipes, oriundos de criação massal no próprio laboratório. As diluições dos óleos foram realizadas em Tween® 80 nas concentrações de 0, 100, 150 e 200 mg mL-1. 1,0 µL de cada diluição foi aplicado na região protorácica dos insetos. A mortalidade de S. frugiperda foi verificada pelo contato tópico do óleo de V. arborea com LC10 = 74,3 mg mL-1 e LC50 = 172,86 mg mL-1, para L. microphyla, LC10 = 51,26 mg mL-1 e LC50 = 104,52 mg mL-1. As concentrações letais observadas para E. annulipes foram V. arborea LC10 = 71,3 mg mL-1 e LC50 = 160,2 mg mL-1. Enquanto L. microphyla, foram LC10 = 50,3 mg mL-1 e LC50 = 134,67 mg mL-1. Os óleos essenciais de V. arborea e L. microphylla são eficientes no controle de S. frugiperda, mas não são seletivos ao predador E. Annulipes.

Evaluation of antibacterial and antioxidant activity of purple araçá essential oil (Psidium rufum, Myrtaceae) / Avaliação das atividades antibacteriana e antioxidante do óleo essencial do araçá-roxo (Psidium rufum, Myrtaceae)

The aim of this study was to evaluate the antibacterial and antioxidant activities of essential oil (EO) from fresh leaves of Psidium rufum. The EO was extracted by hydrodistillation and identified by gas chromatography coupled to mass spectrometry. The antibacterial activity was evaluated by determining the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC). Antioxidant activity was determined by ß-carotene/linoleic acid co-oxidation system, 2,2-diphenyl-1-picrylhydrazyl radical scavenging and iron reduction methods. Hydrocarbon sesquiterpenes were the predominant class, indicating 1,8 cineole, α-longipinene as major. The EO was tested against the bacteria Staphylococcus aureus and Pseudomonas aeruginosa (MIC = 2,500 µg/mL and MBC = 20,000 µg/mL); Enterococcus faecalis (MIC = 2,500µg/mL and MBC > 20,000µg/mL) and Escherichia coli (MIC > 20,000µg/mL and MBC > 20,000µg/mL). The EO showed antioxidant potential due to ß-carotene/linoleic acid co-oxidation system, with 76.63% of oxidation inhibition (1.0mg/mL) and due to the iron reduction power (5,38 µmol Fe 2+ /mg sample). The results are promising in recommending this species for the development of food, cosmetic and pharmaceutical products.

O objetivo deste estudo foi avaliar as atividades antibacteriana e antioxidante do óleo essencial (OE) das folhas frescas de Psidium rufum. O OE foi extraído por hidrodestilação e identificado por cromatografia gasosa acoplada à espectrometria de massas. Foi avaliada a atividade antibacteriana, determinando-se a concentração inibitória mínima (CIM) e a concentração bactericida mínima (CBM). A atividade antioxidante foi determinada pelo sistema de co-oxidação ß-caroteno/ácido linoleico, pelos métodos de sequestro do radical 2,2-difenil-1-picrilhidrazil e de redução do ferro. Sesquiterpenos hidrocarbonetos foram a classe predominante, indicando 1,8 cineol, α-longipineno como majoritário. O OE foi testado contra as bactérias Staphylococcus aureus e Pseudomonas aeruginosa (CIM = 2,500µg/mL e CBM = 20.000µg/mL); Enterococcus faecalis (CIM=2,500µg/mL e CBM > 20.000µg/mL) e Escherichia coli (CIM > 20.000µg/mL e CBM > 20.000µg/mL). O OE apresentou potencial antioxidante pelo sistema co-oxidação ß-caroteno/ácido linoleico com 76,63% de inibição da oxidação (1,0mg/mL) e pelo poder de redução de ferro (5,38 µmol Fe2+/mg amostra). Os resultados são promissores em indicar essa espécie para o desenvolvimento de produtos alimentícios, cosméticos e farmacêuticos.

Estudio de las Propiedades Moleculares y Reactivas del eucaliptol usando la Teoría Funcional de la Densidad DFT B3LYP/6-31G* / Reactive and Molecular properties of eucaliptol using Density Functional Theory DFT B3LYP/6-31G*

Introducción: El eucalipto fue utilizado el 2020 para tratar síntomas del coronavirus, en un intento de comprender el comportamiento reactivo del componente principal el eucaliptol, y con la finalidad de disponer de información preliminar para estudios posteriores, es que se escogió a esta molécula en el presente estudio. Se realizó un estudio químico teórico computacional, se calcularon propiedades moleculares, valores de longitudes de enlace y ángulos, así como propiedades químicas y descriptores químicos de interés en estudios QSAR, de energías y de reactividad. Objetivo: Determinar las propiedades moleculares, y descriptores de reactividad del eucaliptol con el fin de comprender el comportamiento reactivo mediante la Teoría Funcional de la Densidad (DFT). Método: Este estudio computacional utilizo los métodos Hartree Fock y la Teoría Funcional de densidad DFT, las propiedades químicas y descriptores moleculares para el eucaliptol, simulado en condiciones de vacío y en medio etanólico, fueron comparadas con los datos de referencia del Banco de Datos Europeo. Los descriptores ADME se calcularon con la estructura optimizada, usando los servidores en línea SwissADME y ADMETlab. Resultados: En cuanto se refiere a las longitudes de enlace intramolecular se encontró que no hay diferencia estadística significativa entre las longitudes de enlace en los cuatro tratamientos cuánticos. En los orbitales frontera, un band gap de 8,1 eV entre los orbitales HOMO LUMO muestra que la molécula es muy estable, los orbitales HOMO-1 y LUMO+1 de 9,8eV indica que se necesitaría mucha energía para que ocurra una transición electrónica. Conclusión: La teoría DFT B3LYP/6-31G fue aplicada sobre la estructura del eucaliptol, se investigaron algunas propiedades geométricas, electrónicas, de reactividad química y descriptores ADME intentando comprender el comportamiento reactivo de esta molécula, la energía de los orbitales HOMO-LUMO mostraron que la molécula tiene estabilidad energética, y los descriptores ADME sugieren una buena absorción a través de las membranas, finalmente el eucaliptol no es mutagénico desde el punto de vista de la química teórica.

Introduction: Eucalyptol was used in 2020 to treat coronavirus symptoms, in an attempt to understand the reactive behavior of the eucalyptol, a main molecule, and in order to have preliminary information for subsequent studies, this molecule was chosen in this study. A computational theoretical chemical study was carried out, molecular properties, values ​​of bond lengths and angles, as well as chemical properties and chemical descriptors of interest in QSAR, energy and reactivity studies were calculated. Objective: To determine the molecular properties and reactivity descriptors of eucalyptol in order to understand the reactive behavior through the Density Functional Theory (DFT). Method: This computational study used the Hartree Fock methods and the DFT Density Functional Theory, the chemical properties and molecular descriptors for eucalyptol, simulated under vacuum conditions and in ethanolic medium, were compared with the reference data from the Data Bank. European. The ADME descriptors were calculated with the optimized structure, using the online servers SwissADME and ADMETlab. Results: Regarding the intramolecular bond lengths, it was found that there is no statistically significant difference between the bond lengths in the four quantum treatments. In the frontier orbitals, a band gap of 8.1 eV between the HOMO LUMO orbitals shows that the molecule is very stable, the HOMO-1 and LUMO+1 orbitals of 9.8eV indicate that a lot of energy would be needed for a transition to occur. electronics. Conclusion: The DFT B3LYP/6-31G theory was applied to the structure of eucalyptol, some geometric, electronic, chemical reactivity properties and ADME descriptors were investigated trying to understand the reactive behavior of this molecule, the energy of the HOMO-LUMO orbitals showed that the molecule has energetic stability, and the ADME descriptors suggest a good absorption through the membranes, finally eucalyptol is not mutagenic from the point of view of theoretical chemistry.

Bioinsecticide potential of Curcuma zedoaria rhizome essential oil / Potencial bioinseticida do óleo essencial dos rizom as de curcuma zedoaria

In this study the potential bioinseticide of the essential oil (OE) extracted from the rhizomes of the species Curcuma zedoaria (Zingiberaceae) was evaluated. The rhizomes were collected during dormancy (winter) and budding (summer). The EO was obtained by hydrodistillation (2h) and identified by GC/MS. In addition, a multivariate exploratory analysis was done to determine the analysis of the major compounds (PCA). The EO yield in dormancy was 0.61± 0.07 (%) and in budding 0.55 ± 0.08 (%). The bioassays on Aedes aegypti larvae and pupae were done by immersion test at different EO concentrations which ranged from 500.00 to 0.003 mg mL-1 (v/v). The results on the larvae and pupae indicated LC99.9 of (0.01 and 1.38 mg mL-1) for EO in dormancy, and (0.08 and 2.63 mg mL-1) for EO during budding, respectively. The action mechanism of EOs in both periods was determined by autobiographic method evaluating the inhibitory potential on the acetylcholinesterase enzyme, indicating greater inhibition of the EO enzyme during dormancy (0.039 mg mL-1) when compared to the EO during budding (0.156 mg mL-1). The projection representation of the EO chemical classes in both evaluated periods indicated that oxygenated sesquiterpenes are the major compound class (46.99% in dormancy) and (43.59% in budding). The projection of major chemical compounds of EOs presented three compounds with greater mass flow distancing: epicurzerenone (18.20% and 12.10%); 1.8 cineole (15.76% and 12.10%) and ß-elemene (4.43 and 0.01%) that are found in greater amounts in the dormancy EO when compared to budding, respectively. These results corroborate with the greater potential on Ae. aegypti larvae and pupae found for the dormancy EO. The results are promising because they show in which vegetative cycle phase C. zedoaria EO presents greater bioinsecticidepotential.

Neste trabalho foi avaliado o potencial bioinseticida do óleo essencial (OE) extraído dos rizomas da espécie Curcuma zedoaria (Zingiberaceae), coletados no período de dormência (inverno) e brotação das gemas (verão). O OE foi obtido por hidrodestilação (2h) e identificado por CG/EM foi observado rendimento 0,61 ± 0,07 (%) no óleo da dormência, quando comparado no período de brotação 0,55 ± 0,08 (%). Os bioensaios sobre as larvas e pupas de Aedes aegypti foram realizados pelo teste de imersão em diferentes concentrações dos OEs, que variaram de 500,00 a 0,003 mg mL-1 (v/v). Os resultados sobre as larvas e pupas indicaram uma CL99,9 de (0,01 e 1,38 mg mL-1) para o OE da dormência, e (0,08 e 2,63 mg mL-1) para o OE do período de brotação, respectivamente. Indicando maior atividade do OE da dormência. O mecanismo de ação dos OEs nos dois períodos foi determinado pelo método autobiográfico avaliando o potencial inibitório sobre a enzima acetilcolinesterase. Os resultados indicaram maior inibição da enzima do OE no período de dormência (0,039 mg mL-1), quando comparado ao OE de brotação (0,156 mg mL-1). A análise química destacou três compostos: epicurzerenone (18,20% e 12,10%) e 1,8 cineol (15,76% e 14,05%) e ß- elemeno (4,43 e 0,01%) em maior quantidade no período de dormência quando comparado ao período de brotação, respectivamente. Esta diferença pode explicar a maior ação inseticida do OE de dormência sobre as larvas e pupas do Ae. aegypti. Os resultados são promissores, pois estabelece em qual período do ciclo vegetativo o OE da C. zedoaria apresenta maior potencial bioinseticida.

Study on peel components and juice quality of three mandarin hybrids (Citrus reticulata) on sour orange rootstock cultivated in Ramsar, Iran / Estudio sobre los componentes de la cáscara y la calidad del jugo de tres híbridos de mandarina (Citrus reticulata) en patrones de naranja agria cultivados en Ramsar, Irán

The peel components and juice quality of three mandarin hybrids were investigated in this study. Peel components were extracted using the cold-press method and analyzed using GC-FID and GC-MS. Total soluble solids, total acid, pH value, ascorbic acid as well as density were determined in juice obtained from mandarin hybrids. Twenty-six, thirty-five and nineteen peel components were identified in Fortune, Robinson and Osceola respectively including: aldehydes, alcohols, esters, monoterpenes, sesquiterpenes and other components. The major components were limonene, γ-terpinene, (E)-ß-ocimene, ß-myrcene, sabinene, linalool and α-Pinene. Among the three scions examined, Fortune showed the highest content of aldehydes and Robinson showed the highest content of TSS. This study shows that scion has a profound influence on aldehyd and TSS that are important to quality improvement.

Los componentes de la cáscara y la calidad del jugo de tres híbridos de mandarina fueron investigados en este estudio. Los componentes de la cáscara fueron extraídos por el método de prensado en frío y se analizaron mediante GC-FID y GC-MS. el total de sólidos solubles, acidez total, pH, ácido ascórbico, así como la densidad se determinaron en el jugo obtenido a partir de híbridos de mandarina. Veintiséis, treinta y cinco y diecinueve componentes de la cáscara de Fortuna, Robinson y Osceola respectivamente fueron identificados, incluyendo: aldehídos, alcoholes, ésteres, monoterpenos, sesquiterpenos y otros componentes. Los componentes principales eran limoneno, γ-terpineno, (E) -ß-ocimeno, ß-mirceno, sabineno, linalool y α-pineno. Entre los tres vástagos examinados, Fortune mostró el mayor contenido de aldehídos y Robinson mostró el mayor contenido de SST. Este estudio muestra que el vástago tiene una profunda influencia en aldehído y SST que son importantes para mejorar la calidad.

Antibacterial activity of essential oils of aloysia polystachya and lippia turbinata (Verbenaceae) / Actividad antibacteriana de los aceites esenciales de aloysia polystachya y lippia turbinata (Verbenaceae)

Aloysia polystachya and Lippia turbinata are medicinal and aromatic plants. Nevertheless, there are few reports in literature concerning the biological properties of species that grow in northeastern Argentina. The antibacterial activity and the chemical composition of both essential oils were evaluated in this work. The extraction was performed by steam distillation and their volatile compounds were determined by gas chromatography/mass spectrometry. The antibacterial activity was evaluated by disc diffusion and broth microdilution assay. The main compounds were carvone (78.9 percent) and limonene (14.2 percent) in A. polystachya and carvone (80.77 percent), limonene (8.73 percent), beta- caryophyllene (2.13 percent) and 1,8-cineole (1.70 percent) in L. turbinata. Both essential oils were bactericide against Escherichia coli ATCC 35218 and clinical isolates of Enterobacter cloacae and Klebsiella pneumoniae. Essential oil of A. polystachya was also bactericide against Staphylococcus aureus ATCC 29212, S. aureus ATCC 25923 and clinical strain of S. aureus methicillin susceptible.

Aloysia polystachya y Lippia turbinata son plantas medicinales y aromáticas. Hay pocos informes en la literatura sobre las propiedades biológicas de especies que crecen en el nordeste de Argentina. La actividad antibacteriana y la composición química de ambas especies se evaluaron en este trabajo. La extracción se realizó por destilación con vapor y sus compuestos se determinaron por cromatografía gaseosa/espectrometría de masa. La actividad antibacteriana fue evaluada por difusión en discos y microdilución en caldo. Los principales compuestos fueron carvona (78.9 por ciento) y limoneno (14.2 por ciento) en A. polystachya y carvona (80.77 por ciento), limoneno (8.73 por ciento), beta-cariofileno (2.13 por ciento) y 1,8-cineol (1.70 por ciento) en L. turbinata. Ambos aceites esenciales fueron activos contra Escherichia coli ATCC 35218 y aislamientos clínicos de Enterobacter cloacae y Klebsiella pneumoniae. El aceite esencial de A. polystachya fue bactericida contra Staphylococcus aureus ATCC 29212, S. aureus ATCC 25923 y aislamientos clínicos de S. aureus sensible a meticilina.

Composition of the essential oil from leaves of Smallanthus quichensis (Asteraceae) from Costa Rica / Composición química del aceite esencial de las hojas de Smallanthus quichensis (Asteraceae) de Costa Rica

Smallanthus is a genus of flowering plants in the Asteraceae family, which has about 24 species, ranging mostly from southern Mexico and Central America to the Andes in South America. The aim of the present study was to identify the chemical composition of leaf essential oil of S. quichensis, growing wild in Costa Rica. The extraction of the oils was carried out by the hydrodistillation method, using a modified Clevenger type apparatus. The chemical composition of the oils was analyzed by capillary GC-FID and GC-MS using the retention indices on DB-5 type capillary column. A total of 100 compounds were identified, accounting for about 90 percent of the total amount of the oils. Smallanthus quichensis leaf produced a monoterpenoid-rich oil, whose composition was dominated by αlfa-pinene (64.5 percent) and 1,8-cineole (9.7 percent) or, in a different sample, by αlfa-pinene (35.5 percent) with moderate amounts of p-cymene (11.5 percent), beta-phellandrene (9.2 percent), alfa-phellandrene (9.0 percent) and limonene (5.8 percent). This is the first report of the chemical composition of the essential oil obtained from this plant species.

Smallanthus es un género de plantas perteneciente a la familia Asteraceae que contiene aproximadamente 24 especies, la mayoría ubicadas desde el sur de México, América Central y hasta la cordillera de los Andes en América del Sur. El objetivo del presente estudio fue el de identificar la composición química del aceite esencial de las hojas de S. quichensis. La extracción se realizó mediante el método de hidrodestilación, empleando un instrumento de tipo Clevenger. Se analizó la composición de los aceites mediante CG-FID y CG-EM, utilizando índices de retención obtenidos en una columna capilar tipo DB-5. Se identificaron 100 compuestos, correspondientes a un 90 por ciento de los constituyentes totales. Los aceites están constituidos principalmente por monoterpenoides (ca. 85 por ciento). Los componentes mayoritarios se identificaron como alfa-pineno (64.5 por ciento), acompañado por 1,8-cineol (9.7 por ciento) o, en otra muestra distinta, αlfa-pineno (35.5 por ciento) junto a cantidades moderadas de p-cimeno (11.5 por ciento), beta-felandreno (9.2 por ciento), alfa-felandreno (9.0 por ciento) y limoneno (5.8 por ciento). Este es el primer informe acerca de la composición química de aceites esenciales obtenidos de S. quichensis.

Análisis multivariable de la composición química de aceite esencial dehojas de Melaleuca quinquenervia que crece en Cuba / Multivariate analysis of the chemical composition of the essential oil from leaves of Melaleuca quinquenervia growing in Cuba

El aceite esencial de Melaleuca quinquenervia de la Ciénaga de Zapata, Cuba, obtenido a escala piloto con un rendimiento promedio de 0,8%, presentó una densidad relativa y un índice de refracción promedios de 0,9253g/mL y 1,4827 respectivamente. La determinación de su composición química por cromatografía de gases acoplada a espectrometría de masas permitió identificar 42 compuestos, de los cuales 26 se sometieron al Análisis por Componentes Principales y al Análisis por Conglomerados. Dichos análisis permitieron la separación de las muestras en dos grupos con diferencias significativas (p<0,05) entre los contenidos promedios de sus principales constituyentes. A partir de dichos análisis se estableció la presencia de dos quimiotipos diferentes: uno con elevados contenidos de viridiflorol (33,8 por ciento), seguido por el 1,8-cineol (21,8 por ciento), y otro quimiotipo del tipo 1,8-cineol (30,0 por ciento) con un contenido relativamente elevado de viridiflorol (24,6 por ciento). Ambos quimiotipos presentaron concentraciones similares de los monoterpenos limoneno y αlfa-pineno.

The essential oil of Melaleuca quinquenervia from Ciénaga de Zapata, Cuba, obtained at pilot scale with average yield of 0.8%, showed average relative density and refraction index of 0.9253g/mL and 1.4827 respectively. It ́s chemical composition determination by gas chromatography coupled to Mass Spectrometry allow identifying 42 compounds, 26 of which were submitted to Principal Components Analysis and to Conglomerates Analysis. Such analyses allowed the separation of the samples into two groups with significant differences (p<0.05) between the average contents of its main components. From such analyses, it was established the presence of two different chemotypes: one with high contents of viridiflorol (33.8 percent), followed by 1,8-cineol (21.8 percent), and another chemotype rich in 1,8-cineol (30,0 percent) with a relatively high content in viridiflorol (24.6 percent). Both chemotypes showed similar concentrations of limonene and αlfa-pinene monoterpenes.

In vitro inhibition of the bovine viral diarrhoea virus by the essential oil of Ocimum basilicum (basil) and monoterpenes.

The bovine viral diarrhoea virus (BVDV) is suggested as a model for antiviral studies of the hepatitis C virus (HCV). The antiviral activity of the essential oil of Ocimum basilicum and the monoterpenes camphor, thymol and 1,8-cineole against BVDV was investigated. The cytotoxicities of the compounds were measured by the MTT (3-(4.5-dimethylthiazol-2-yl)-2.5-diphenyltetrazolium bromide) test, and the antiviral activities were tested by the plaque reduction assay. The oil or compounds were added to the assay in three different time points: a) pre-treatment of the virus (virucidal assay); b) pre-treatment of the cells; or c) post-treatment of the cells (after virus inoculation). The percentage of plaques inhibition for each compound was determined based on the number of plaques in the viral control. The results were expressed by CC50 (50% cytotoxic concentration), IC50 (inhibitory concentration for 50% of plaques) and SI (selectivity index = CC50/IC50). Camphor (CC50 = 4420.12 µg mL(-1)) and 1,8-cineole (CC50 = 2996.10 µg mL(-1)) showed the lowest cytotoxicities and the best antiviral activities (camphor SI = 13.88 and 1,8-cineol SI = 9.05) in the virucidal assay. The higher activities achieved by the monoterpenes in the virucidal assay suggest that these compounds act directly on the viral particle.

In vitro inhibition of the bovine viral diarrhoea virus by the essential oil of Ocimum basilicum (basil) and monoterpenes

The bovine viral diarrhoea virus (BVDV) is suggested as a model for antiviral studies of the hepatitis C virus (HCV). The antiviral activity of the essential oil of Ocimum basilicum and the monoterpenes camphor, thymol and 1,8-cineole against BVDV was investigated. The cytotoxicities of the compounds were measured by the MTT (3-(4.5-dimethylthiazol-2-yl)-2.5-diphenyltetrazolium bromide) test, and the antiviral activities were tested by the plaque reduction assay. The oil or compounds were added to the assay in three different time points: a) pre-treatment of the virus (virucidal assay); b) pre-treatment of the cells; or c) post-treatment of the cells (after virus inoculation). The percentage of plaques inhibition for each compound was determined based on the number of plaques in the viral control. The results were expressed by CC50 (50% cytotoxic concentration), IC50 (inhibitory concentration for 50% of plaques) and SI (selectivity index = CC50/IC50). Camphor (CC50 = 4420.12 µgmL-1) and 1,8-cineole (CC50 = 2996.10 µgmL-1) showed the lowest cytotoxicities and the best antiviral activities (camphor SI = 13.88 and 1,8-cineol SI = 9.05) in the virucidal assay. The higher activities achieved by the monoterpenes in the virucidal assay suggest that these compounds act directly on the viral particle.

In vitro inhibition of the bovine viral diarrhoea virus by the essential oil of Ocimum basilicum (basil) and monoterpenes

The bovine viral diarrhoea virus (BVDV) is suggested as a model for antiviral studies of the hepatitis C virus (HCV). The antiviral activity of the essential oil of Ocimum basilicum and the monoterpenes camphor, thymol and 1,8-cineole against BVDV was investigated. The cytotoxicities of the compounds were measured by the MTT (3-(4.5-dimethylthiazol-2-yl)-2.5-diphenyltetrazolium bromide) test, and the antiviral activities were tested by the plaque reduction assay. The oil or compounds were added to the assay in three different time points: a) pre-treatment of the virus (virucidal assay); b) pre-treatment of the cells; or c) post-treatment of the cells (after virus inoculation). The percentage of plaques inhibition for each compound was determined based on the number of plaques in the viral control. The results were expressed by CC50 (50% cytotoxic concentration), IC50 (inhibitory concentration for 50% of plaques) and SI (selectivity index = CC50/IC50). Camphor (CC50 = 4420.12 µgmL-1) and 1,8-cineole (CC50 = 2996.10 µgmL-1) showed the lowest cytotoxicities and the best antiviral activities (camphor SI = 13.88 and 1,8-cineol SI = 9.05) in the virucidal assay. The higher activities achieved by the monoterpenes in the virucidal assay suggest that these compounds act directly on the viral particle.(AU)

Composição química e atividade antimicrobiana dos óleos essenciais das folhas e flores de Callistemon viminalis (sol. ex Gaertn.) G. Don ex. Loudon (Myrtaceae) / Chemical composition and antimicrobial activity of essential oils of leaves and flowers of Callistemon viminalis (sol. ex Gaertn.) G. Don ex. Loudon (Myrtaceae)

O presente trabalho teve como objetivo determinar a composição química e avaliar a atividade antimicrobiana dos óleos essenciais obtidos das folhas (frescas e secas) e flores da Callistemon viminalis. Os óleos essenciais foram analisados por CG/EM. A concentração inibitória mínima (CIM) foi determinada utilizando o método de microdiluição em caldo frente a bactérias Gram-positivas e Gram-negativas. De um total de 96,72%, 98,70% dos compostos identificados nos óleos essenciais foram monoterpenos. O 1,8-cineol foi o componente majoritário no óleo essencial das folhas frescas (70,43%), folhas secas (71,71%) e flores (42,39%), seguido do tricicleno com 12,97% nas folhas frescas, 8,20% nas folhas secas e 28,08% nas flores. A CIM para todos os micro-organismos testados foi ≥ a 2.000 μg/mL. Esse estudo é o primeiro relato sobre a composição química e atividade antimicrobiana do óleo essencial das flores de C. viminalis.

The aim of this study was to determine the chemical composition and the antimicrobial activity of essential oils of Callistemon viminalis leaves (fresh and dried) and flowers. The essential oils were analyzed by GC/MS and the minimum inhibitory concentration (MIC) against Gram-positive and Gram-negative bacteria was determined by the broth microdilution method. Between 96.72% and 98.70% of the compounds identified in the essential oils were monoterpenes. 1,8-Cineole was the major component in the essential oils of fresh leaves (70.43%), dried leaves (71.71%) and flowers (42.39%), followed by tricyclene: 12.97% in the fresh leaves, 8.20% in the dried leaves and 28.08% in the flowers. The MIC for all microorganisms tested was ≥ 2,000 μg/mL, for all the essential oil samples. This study is the first report on the chemical composition and antimicrobial activity of essential oil from the flowers of C. viminalis.

Antibacterial activity and chemical composition of essential oil of Lippia microphylla Cham / Atividade antibacteriana e composição química do óleo essencial de Lippia microphylla Cham

The essential oil from the fresh leaves of Lippia microphylla Cham. wasobtained by hydrodistillation and characterized by gas chromatography-mass spectrometry(GC-MS). Major constituents of the oil were 1.8-cineole (18.12%), -ocimene (15.20%),bicyclogermacrene (11.63%) and caryophyllene oxide (8.32%). Antimicrobial activity of theoil against Gram-positive and Gram-negative bacteria was determined by gel diffusionmethod. The oil showed good antibacterial activity against Shigella flexneri, Escherichia coli andStreptococcus pyogenes and very good antibacterial activity against Staphylococcus aureus.(AU)

O óleo essencial das folhas frescas de Lippia microphylla Cham.foi obtido por hidrodestilação e caracterizado por cromatografia gasosa acoplada aespectrometria de massas (CG-EM). O constituinte majoritário do óleo foi 1.8-cineol(18,12%), -ocimeno (15,20%), bicyclogermacreno (11,63%) e óxido de caryophylleno(8,32%). A atividade antimicrobiana do óleo frente às bactérias Gram-positivas e Gramnegativasfoi determinada pelo método de difusão em gel. O óleo apresentou uma boaatividade antibacteriana frente a Shigella flexneri, Escherichia coli e Streptococcus pyogenes sendo omelhor resultado frente a Staphylococcus aureus.(AU)

Antibacterial activity and chemical composition of essential oil of Lippia microphylla Cham / Atividade antibacteriana e composição química do óleo essencial de Lippia microphylla Cham

The essential oil from the fresh leaves of Lippia microphylla Cham. was obtained by hydrodistillation and characterized by gas chromatography-mass spectrometry (GC-MS). Major constituents of the oil were 1.8-cineole (18.12%), -ocimene (15.20%), bicyclogermacrene (11.63%) and caryophyllene oxide (8.32%). Antimicrobial activity of the oil against Gram-positive and Gram-negative bacteria was determined by gel diffusion method. The oil showed good antibacterial activity against Shigella flexneri, Escherichia coli and Streptococcus pyogenes and very good antibacterial activity against Staphylococcus aureus.

O óleo essencial das folhas frescas de Lippia microphylla Cham. foi obtido por hidrodestilação e caracterizado por cromatografia gasosa acoplada a espectrometria de massas (CG-EM). O constituinte majoritário do óleo foi 1.8-cineol (18,12%), -ocimeno (15,20%), bicyclogermacreno (11,63%) e óxido de caryophylleno (8,32%). A atividade antimicrobiana do óleo frente às bactérias Gram-positivas e Gram-negativas foi determinada pelo método de difusão em gel. O óleo apresentou uma boa atividade antibacteriana frente a Shigella flexneri, Escherichia coli e Streptococcus pyogenes sendo o melhor resultado frente a Staphylococcus aureus.

Teor e composição do óleo essencial de inflorescências e folhas de Lavandula dentata L. em diferentes estádios de desenvolvimento floral e épocas de colheita / Yield and composition of essential oil from inflorescences and leaves of lavender (Lavandula dentata L.) in different flower development stages and harvest times

O óleo essencial de Lavandula dentata L. possui importância econômica devido à utilização nas indústrias farmacêutica, cosmética e de higiene pessoal. O presente trabalho teve como objetivo avaliar o teor e a composição do óleo essencial de inflorescências e folhas de lavanda em diferentes estádios de desenvolvimento. O delineamento experimental foi inteiramente casualizado em esquema fatorial 2 x 3, sendo três estádios de desenvolvimento floral (botão, pré-antese/antese e senescente) e duas épocas de colheita (janeiro e abril), com cinco repetições. As amostras de óleo essencial foram obtidas por hidrodestilação, sendo os constituintes analisados por cromatografia em fase gasosa acoplada à espectrometria de massas (CG/EM). Houve interação entre os fatores épocas de colheita e desenvolvimento floral no teor de óleo essencial das inflorescências, sendo observada média superior em botões florais colhidos em janeiro. Os estádios de desenvolvimento não alteraram o teor do óleo essencial das folhas. Os estádios de desenvolvimento influenciaram nos teores dos constituintes dos óleos essenciais das inflorescências e folhas. No óleo essencial em estádio de flor senescente da colheita de abril, observou-se teor elevado de 1,8-cineol, enquanto nos demais estádios de desenvolvimento os teores foram menores em ambas as épocas de colheita. Teores elevados de cânfora foram observados nos estádios de pré-antese/antese e senescente, na colheita de janeiro. O óleo essencial das folhas apresentou teor superior de 1,8-cineol em ramos com flores em estádio de pré-antese/antese. Os teores de cânfora e fenchona foram superiores em ramos contendo botões. O óleo essencial das folhas de ramos com botões e flores senescentes apresentou teor superior de linalol em relação ao óleo essencial das inflorescências.

The essential oil of Lavandula dentata L. has economic importance due to its utilization by pharmaceutical, cosmetic and personal care industries. The aim of this study was to evaluate the yield and composition of essential oil from lavender inflorescences and leaves in different development stages. The experimental design was completely randomized in 2 x 3 factorial arrangement, with three flower development stages (bud, pre-anthesis/anthesis and senescence) and two harvest periods (January and April), and 5 replicates. The essential oil samples were obtained by hydrodistillation, and the compounds were analyzed by gas chromatography coupled to mass spectrometry (GC/MS). There was an interaction between the factors harvest time and flower development on essential oil yield of inflorescences, and a superior average was observed for flower buds harvested in January. The development stages did not alter the essential oil yield of leaves. The development stages influenced the levels of compounds of the essential oil from inflorescences and leaves. For essential oil in senescent flower stage harvested in April, there was a high level of 1,8-cineol, whereas in the remaining development stages, the levels were lower in both harvest times. The levels of camphor increased in the pre-anthesis/anthesis and senescence in January harvest. The essential oil from leaves presented higher levels of 1,8-cineol in branches with flowers in pre-anthesis/anthesis. Camphor and fenchone levels were higher in branches with buds. The essential oil from leaves of branches with buds and senescent flowers showed higher levels of linalool than that from inflorescences.

Estudo químico e da atividade biológica cardiovascular do óleo essencial de folhas de Alpinia zerumbet (Pers.) B.L.Burtt & R.M.Sm. em ratos / Phytochemistry and cardiovascular biological activity of the essential oil from leaves of Alpinia zerumbet (Pers.) B.L. Burtt & R.M.Sm. in rats

A espécie vegetal Alpinia zerumbet (Pers.) B.L.Burtt & R.M. Sm. é popularmente empregada para o tratamento de diversas enfermidades, entre elas a hipertensão. Avaliar a composição química, a atividade antihipertensiva e ação na hipertrofia cardíaca do óleo essencial das folhas de Alpinia zerumbet (OEAZ) em ratos foram os objetivos deste estudo. O OEAZ, obtido por hidrodestilação em aparelho Clevenger, teve sua composição química analisada em cromatografia gasosa acoplada à espectrometria de massas (CG-EM). Foram identificados 14 constituintes, sendo terpinen-4-ol (37,45 por cento) o majoritário, seguido pelos óxido de cariofileno (7,56 por cento), trans-hidrato de sabineno (6,61 por cento) e 1,8-cineol (4,02 por cento). A avaliação cardiovascular foi feita após o tratamento crônico de ratos espontaneamente hipertensos (SHR) e seus respectivos controles, ratos Wistar-Kyoto (WKY). Os dados hemodinâmicos revelaram redução da pressão arterial média (PAM) no grupo tratado (SHRP: 160 ± 7 mm Hg; p<0,01) em relação ao não tratado (SHR: 180 ± 5 mm Hg). A relação entre peso do ventrículo esquerdo e peso corporal (VE/PC) do SHRP (2,50 ± 0,03 mg g-1; p<0,01) mostrou-se inferior ao SHR (2,61 ± 0,01 mg g-1), confirmando a redução da hipertrofia cardíaca (HC). Os dados de PAM e VE/PC dos animais SHRP foram estatisticamente diferentes quando comparados com os ratos controle (WKY: 116 ± 2 mm Hg e WKYP: 119 ± 4 mm Hg; p<0,05; WKY: 2,15 ± 0,04 mg g-1 e WKYP: 2,17 ± 0,04 mg g-1 ; p<0,01), indicando não ter havido normalização dos mesmos. Conclui-se que o tratamento crônico com OEAZ foi capaz de determinar redução, mas não a normalização, da PAM e da HC de ratos SHR, provavelmente pela presença dos componentes terpinen-4-ol e 1,8-cineol. Estudos com doses maiores ou período de tratamento superior são necessários para avaliar a possibilidade de o OEAZ normalizar os parâmetros analisados (PAM e HC).

Alpinia zerumbet (Pers.) B.L. Burtt & R.M.Sm. is traditionally employed to treat several diseases such as hypertension. The aim of this study was to evaluate the chemical composition, the anti-hypertensive activity and the capacity to reduce cardiac hypertrophy of the essential oil of A. zerumbet leaves (EOAZ) in rats. EOAZ was obtained through hydrodistillation in Clevenger apparatus and its chemical composition was analyzed by gas chromatography-mass spectrometry (GC-MS). Several constituents (14) were identified, terpen-4-ol (37.45 percent) being the major component, followed by caryophyllene oxide (7.56 percent), trans-sabinene hydrate (6.61 percent) and 1,8-cineol (4.02 percent). The cardiovascular effect was investigated after chronic treatment with spontaneously hypertensive rats (SHR) and their respective controls, Wistar-Kyoto rats (WKY). The treated group showed a lower mean arterial pressure (MAP) (SHRP: 160 ± 7 mm Hg; p<0.01) than the untreated group (SHR: 180 ± 5 mm Hg). The ratio of left ventricle-to-body weight (LV/BW) for SHRP was lower (2.504 ± 0.03 mg g-1; p<0.01) than that for SHR (2.162 ± 0.01 mg g-1), confirming the cardiac hypertrophy (CH) reduction. There were significant differences in MAP and CH between SHRP animals and control rats (WKY: 116 ± 2 mm Hg and WKYP: 119 ± 4 mm Hg; p<0.05. WKY: 2.152 ± 0.04 mg g-1 and WKYP: 2.168 ± 0.04 mg g-1; p<0.01), indicating that these values were not normalized. Those data showed that the chronic treatment with EOAZ reduces MAP and CH in SHR probably due to the presence of the compounds terpinen-4-ol and 1,8-cineol. Studies with higher doses or longer treatment periods are necessary to evaluate whether EOAZ can reduce the analyzed parameters (MAP and CH) to normal values.

Composition of the essential oil from the leaves of tree domestic varieties and one wild variety of the guava plant (Psidium guajava L., Myrtaceae) / Avaliação dos constituintes dos óleos essenciais de folhas de goiabeira (Psidium guajava L., Myrtaceae) de três cultivares e da planta silvestre

The compositions of the essential oils from the leaves of three domestic varieties of the guava tree Psidium guajava L. (Paluma, Século XXI and Pedro Sato) and of one wild variety were compared. Essential oils were extracted by steam distillation, the components were identified by gas chromatography coupled to mass spectrometry GC-MS, and the apparent concentrations were determined by gas chromatography with a flame ionization detector. The results demonstrated that the three essential oils contained many common substances with a prevalence of 1,8-cineole, whereas the essential oil of the Paluma variety contained 1,8-cineole (42.68 percent) as the major constituent, as well as α-terpineol (38.68 percent). The principal components of the essential oil of the Século XXI variety were 1,8-cineole (18.83 percent), trans-caryophyllene (12.08 percent), and selin-11-en-4-αol (20.98 percent), while those of the Pedro Sato variety and of the wild plant were 1,8-cineole (17.68 percent) and (12.83 percent), caryophyllene oxide (9.34 percent) and (9.09 percent), and selin-11-en-4-α-ol (21.46 percent) and (22.19 percent), respectively.

Os óleos essenciais de folhas de goiabeira Psidium guajava L. de três diferentes cultivares (Paluma, Século XXI e Pedro Sato) e da planta silvestre foram analisados a fim de comparar os seus constituintes. O óleo essencial foi obtido por hidrodestilação em aparelho de Clevenger modificado. Para a caracterização e quantificação dos compostos presentes por CG-EM e CG respectivamente. Os resultados mostraram que os três óleos essenciais analisados apresentam inúmeras substâncias em comum com a predominância do 1,8-cineol. O óleo essencial da cultivar Paluma se difere dos demais devido a alta concentração de 1,8-cineol (42,68 por cento) e do α-terpineol (38,68 por cento). No óleo essencial da cultivar Século XXI observase a presença do 1,8 cineol (18,83 por cento), trans-carifileno (12,08 por cento) e o selin-11-en-4-α-ol (20,98 por cento) como majoritários, enquanto que a cultivar Pedro Sato e a planta silvestre apresentaram com o 1,8 cineol com (17,68 por cento) e (12,83 por cento), oxido de cariofileno (9,34 por cento) e (9,09 por cento) e o selin-11-en-4-α-ol com (21,46 por cento) e (22,19 por cento), respectivamente.

Caracterização química do óleo essencial de folhas de goiabeira (Psidium guajava L.) e seus efeitos no comportamento da lagarta-do-cartucho do milho Spodoptera frugiperda (J. E. Smith, 1797) (Lepidoptera: Noctuidae) / Essential oil chemical composition from leaves of guava (Psidium guajava L.) and its effects on the fall armyworm Spodoptera frugiperda (J. E. Smith, 1797). (Lepidoptera: Noctuidae) behavior

Nesta pesquisa, objetivou-se a obtenção e caracterização do óleo essencial de folhas da goiabeira Psidium guajava cv. Pedro Sato, e seus possíveis efeitos no comportamento da lagarta-do-cartucho do milho Spodoptera frugiperda. O óleo essencial foi obtido pela técnica "arraste a vapor d'água", utilizando-se de um aparelho de Clevenger modificado e submetido, posteriormente, à análise por cromatografia gasosa acoplada a um espectrômetro de massas CG-EM, a fim de investigar sua composição. Para a avaliação dos efeitos do óleo essencial no comportamento das lagartas de 1º ínstar foram testados quatro tratamentos, dois com o óleo essencial na concentração de 0,01 por cento e 0,001 por cento, diluídos em etanol/água 1:1, e duas testemunhas, uma com água e outra com etanol/água 1:1. Os resultados obtidos mostraram que o óleo essencial de folhas de goiabeira apresenta na sua constituição o α-terpineol (0,9 por cento), 1,8-cineol (7,0 por cento), β-cariofileno (7,2 por cento) e o óxido de cariofileno (13,8 por cento). Constatou-se, também, que o óleo essencial demonstrou efeito repelente para a lagarta-do-cartucho na concentração de 0,01 por cento.

The aim of this research was to obtain and characterize essential oil from leaves of Psidium guajava cv. Pedro Sato, and its possible effects on fall armyworm Spodoptera frugiperda behavior. The essential oil was obtained through steam distillation, by using a modified Clevenger apparatus, and the chemical composition was later analyzed by gas chromatography coupled to mass spectroscopy GC-MS. In order to evaluate the essential oil effect on the armyworm of 1st instars behavior, four treatments were tested; two with oil at 0.01 and 0.001 percent in ethanol/water 1:1 concentration; two controls with water and the other with ethanol/water 1:1. The results showed that the above analyzed essential oil constituted of á-terpineole (0.9 percent), 1,8-cineole (7.0 percent), â-caryophyllene (7.2 percent) and the caryophyllene oxide (13.8 percent). It was also found that the essential oil showed a repellent effect toward the fall armyworm at 0.01 percent concentration.

Composição química do óleo volátil de Myrcianthes nativas da região sul do Brasil / Chemical composition of the volatile oils of native Myrcianthes species from South Brazil

O óleo essencial das folhas de Myrcianthes gigantea (Myrtaceae), coletadas no Rio Grande do Sul, foi obtido por hidrodestilação em Clevenger e analisado por CG/detector de ionização de chamas e CG/EM. Trinta e seis compostos foram identificados, totalizando 90,1 por cento do conteúdo do óleo. A composição do óleo demonstrou predominância de sesquiterpenos cíclicos, principalmente da via de ciclização do germacrano, apresentando espatulenol (28,8 por cento) e seu isômero, iso-espatulenol (9,5 por cento), como principais constituintes. A composição do óleo das folhas de M. cisplatensis e M. pungens, coletadas na mesma região, também foi analisada e comparada com estudos prévios reportados para estas espécies coletadas em outros países da América da Sul. O óleo essencial de M. cisplatensis apresentou um alto conteúdo de monoterpenos (56,3 por cento), especialmente das séries pinano e p-mentano, com três compostos majoritários: 1,8-cineol (29,8 por cento), limoneno (10,9 por cento) e a-pineno (8,9 por cento), sendo similar ao reportado. Para o óleo de M. pungens 36 compostos foram identificados, porém sem predomínio majoritário, onde b-cariofileno (10,1 por cento), foi o principal deles. O óleo desta espécie difere do relatado para exemplares coletados na Argentina, rico em monoterpenos, sugerindo uma possível ocorrência de quimiotipos.

The essential oil of Myrcianthes gigantea (Myrtaceae) leaves, which were collected in Rio Grande do Sul (Southern Brazil), was obtained by hydrodistillation in a Clevenger apparatus. The chemical investigation was performed by GC-FID and GC-MS. Thirty-six compounds were identified accounting for 90.1 percent of the oil content. The analyzed species was rich in cyclic sesquiterpenes, mainly those from the germecrane cyclization pathway, among them spathulenol (28.8 percent) and its isomer, iso-spathulenol (9.5 percent). Leaves of M. cisplatensis and M. pungens were also collected in the same region and the analysis of the oil composition was compared with those previously reported for collections from other countries in South America. M. cisplatensis oil showed a high content of monoterpenes (56.3 percent), specially from the p-mentane and pinane groups, with three major compounds: 1,8-cineole (29.8 percent), limonene (10.9 percent) and a-pinene (8.9 percent). These findings are in agreement with those reported previously. For M. pungens, thirty-six compounds were identified without a predominant component. b-caryophyllene (10.1 percent), with caryophyllane skeleton, was the main substance for this sample. For this species the oil composition was quite different from those related for two exemplars collected in Argentina, in which both oil were rich in monoterpenes. This result suggests the occurrence of chemotypes.