Tetradenia riparia leaves, flower buds, and stem essential oils to control of Aedes aegypti larvae

Abstract Tetradenia riparia (Hochst.) Codd (Lamiaceae) is a species native to the African continent and used as an insect repellent. The objective of the study was to evaluate the larvicidal potential of essential oils (EOs) from the leaves, flower buds, and stem of T. riparia, collected in winter against Aedes aegypti larvae. The EOs were extracted by hydrodistillation (3 h) and identified by GC/MS. The EOs were tested against larvae of A. aegypti at concentrations ranging from 12500 to 1.5 µg/mL for 24 h. The insecticide activity was evaluated by probit analysis, and the anticholinesterase activity was determined by bioautographic method. The results of the class projection indicated sesquiterpenes as the majority class, corresponding to 60.66% (leaves), 64.70% (flower buds) and 83.99% (stem), and the bioassays on A. aegypti larvae indicated LC50 of 1590, 675 and 665 µg/mL, respectively. The anticholinesterase activity indicated that the EO of the leaves inhibited the enzyme at a concentration of 780 µg/mL, and those from the flower buds and stem inhibited up to 1560 µg/mL. The results indicated weak activity of essential oils against A. aegypti larvae.

Seasonal variation in the essential oil from Varronia curassavica jacq. accessions / Variación estacional en el aceite esencial de accesiones de Varronia curassavica Jacq

Varronia curassavica has anti-inflammatory properties because of the terpenes, α-humulene and ß-caryophyllene, present in the essential oil. The objective of this study was to evaluate the influence of seasonality on the essential oil of V. curassavica accessions. Leaves from six accessions were collected from the Germplasm Bank of the Federal University of Minas Gerais over 12 months. Correlations between the essential oil content and meteorological factors were determined. Gas chromatography analysis coupled with mass spectrometry was conducted to determine the chemical composition of the essential oil. The content and chemical composition of the oil varied throughout the year. Relative humidity was correlated with accessions ICA-VC2 (-0.64) and ICA-VC4 (0.68). ß-bourbonene, ß-elemene, spathulenol, germacrene, caryophyllene oxide, α-humulene, and ß-caryophyllene occurred in all accessions. Accession ICA-VC3 exhibited lower variation (22.17%), higher average (0.97%) essential oil, and maintained an average abundance of α-humulene greater than 2.6%, which is the amount necessary for phytotherapeutics.

Varronia curassavica tiene propiedades antiinflamatorias debido a los terpenos, α-humuleno y ß-cariofileno, presentes en el aceite esencial. El objetivo de este estudio fue evaluar la influencia de la estacionalidad en el aceite esencial de las accesiones de V. curassavica. Se recolectaron hojas de seis accesiones del Banco de Germoplasma de la Universidad Federal de Minas Gerais durante 12 meses. Se determinaron las correlaciones entre el contenido de aceite esencial y los factores meteorológicos. Se realizó un análisis de cromatografía de gases junto con espectrometría de masas para determinar la composición química del aceite esencial. El contenido y la composición química del aceite varió a lo largo del año. La humedad relativa se correlacionó con las accesiones ICA-VC2 (-0,64) e ICA-VC4 (0,68). En todas las accesiones aparecieron ß-bourboneno, ß-elemeno, espatulenol, germacreno, óxido de cariofileno, α-humuleno y ß-cariofileno. La accesión ICA-VC3 mostró una menor variación (22,17%), un promedio más alto (0,97%) de aceite esencial y mantuvo una abundancia media de α-humuleno superior al 2,6%, que es la cantidad necesaria para los fitoterápicos.

Essential oil composition and cytotoxic activity in twospecies ofthe plant genus Vismia (Hypericaceae) from the Venezuelan Andes

Introduction: The Vismia genus belongs to the Hypericaceae family and comprises around 57 species of which 17 have been located in Venezuela. Previous investigations have been carried out in extracts as well as pure isolated compounds, revealing antimicrobial, antioxidant and anti-HIV, among other, biological activities. Objective: This investigation aims to determine the cytotoxic activity of essential oils from leaves of Vismia baccifera Triana & Planch (VBJ and VBV) and Vismia macrophylla Kunth (VM) collected in three different locations of the Venezuelan Andean region. Methods: Essential oils obtained by hydrodistillation were analyzed using gas chromatography-mass spectrometry (GC-MS) and their cytotoxic activity was analyzed following the MTT (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide) assay. Human tumor cell lines from SKBr3, MCF-7 and PANC-1, two breast carcinomas and one pancreatic adenocarcinoma of ductal type, were tested with the oil samples and human dermis fibroblasts were used as non-tumor cells. Results: β-caryophyllene and trans-caryophyllene were present as major components in VBJ and VBV, respectively, while γ-bisabolene was the main component in the VM sample. Anticancer activity was observed on V. baccifera essential oil against SKBr3, MCF-7 and PANC-1. The selectivity index showed that VBV is highly selective against the SKBr3 cell line and has no activity against non-tumor cells. Conclusions: These results are considered a contribution to natural products research and may provide supportive data for future studies on cancer.

Introducción: El género Vismia pertenece a la familia Hypericaceae y comprende alrededor de 57 especies de las cuales 17 han sido ubicadas en Venezuela. Se han realizado investigaciones previas tanto en extractos como en compuestos puros aislados revelando actividad antimicrobiana, antioxidante y anti-VIH, entre otras actividades biológicas. Objetivo: El propósito de esta investigación es determinar la actividad citotóxica de los aceites esenciales de las hojas de Vismia baccifera Triana & Planch (VBJ y VBV) y Vismia macrophylla Kunth (VM) recolectadas en tres localidades de la región andina venezolana. Métodos: Aceites esenciales obtenidos por hidrodestilación fueron analizados por cromatografía de gases-espectrometría de masas y su actividad citotóxica fue analizada siguiendo el método MTT (bromuro de 3-[4,5-dimetiltiazol-2-il]-2,5-difeniltetrazolio). Los aceites esenciales fueron ensayados frente a células tumorales humanas SKBr3, MCF-7 y PANC-1, dos carcinomas de mama y un adenocarcinoma pancreático del tipo ductal, usando cultivos primarios de fibroblastos de dermis humana como células no tumorales. Resultados: β-cariofileno y trans-cariofileno estuvieron presentes como compuestos mayoritarios en VBJ y VBV, respectivamente, mientras que γ-bisaboleno fue el componente principal en la muestra VM. El aceite esencial de V. baccifera mostró actividad anticancerígena frente a SKBr3, MCF-7 y PANC-1. El índice de selectividad reveló que VBV es altamente selectivo frente a la línea celular SKBr3 y no presenta actividad contra las células no tumorales. Conclusiones: Estos resultados se consideran una contribución a la investigación de los productos naturales y los datos pueden ser de utilidad en futuras investigaciones sobre el cáncer.

β-caryophyllene alleviates cerebral ischemia/ reperfusion injury in mice by activating autophagy / 中国中药杂志

Cerebral ischemia-reperfusion(I/R) injury is an important cause of acute ischemic stroke. Timely elimination of damaged proteins and organelles by regulating autophagy during cerebral ischemia-reperfusion plays an important role in relieving brain damage. In order to investigate whether β-caryophyllene(BCP) could protect neurons from cerebral I/R injury by regulating auto-phagy, C57 BL/6 J male mice were randomly divided into sham operation group, model group, and drug-administered group. After intra-gastric administration was given for 5 days, the middle cerebral artery occlusion(MCAO) model was established by suture method. Twenty four hours after surgery, the infarct volume and neurological function were assessed; the pathological changes of cortical tissue were observed by HE staining; Western blot was used to detect the expression of autophagy-related proteins beclin1, p62, LC3 B and apoptosis-related protein Bcl-2; immunofluorescence was used to observe the expression of LC3 B in the ischemic cortex. The autophagy of cortical tissue in the ischemic area was observed by transmission electron microscopy. The experimental results showed that as compared with the model group, the BCP pretreatment significantly reduced the neurological deficit, decreased the percentage of cerebral infarction volume, reduced the death of brain tissue cells in the ischemic area, up-regulated the expression of beclin1, LC3 B and Bcl-2 protein, down-regulated p62 protein expression, and significantly increased the number of autophagosomes in the cortical tissue of the ischemic area. It was finally determined that BCP could protect neurons from cerebral ischemia-reperfusion injury by activating autophagy.

Light and carbon dioxide-driven synthesis of high-density fuel in Synechococcus elongates UTEX 2973 / 生物工程学报

Development of "liquid sunshine" could be a key technology to deal with the issue of fossil fuel depletion. β-caryophyllene is a terpene compound with high energy density and has attracted attention for its potential application as a jet fuel. The high temperature and high light-tolerant photosynthetic cyanobacterium Synechococcus elongatus UTEX 2973 (hereafter Synechococcus 2973), whose doubling time is as short as 1.5 h, has great potential for synthesizing β-caryophyllene using sunlight and CO₂. In this study, a production of ~121.22 μg/L β-caryophyllene was achieved at 96 h via a combined strategy of pathway construction, key enzyme optimization and precursor supply enhancement. In addition, a final production of ~212.37 μg/L at 96 h was realized in a high-density cultivation. To our knowledge, this is the highest production reported for β-caryophyllene using cyanobacterial chassis and our study provide important basis for high-density fuel synthesis in cyanobacteria.

Ocotea (Lauraceae) Amazonian essential oils chemical composition and their tyrosinase inhibition to use in cosmetics / Ocotea (Lauraceae) composición química de aceites esenciales amazónicos y su inhibición de la tirosinasa para usar en cosméticos

This study presents analyses on the chemistry, biology, pharmacology and chromatography of essential oils extracted from three species of the Ocotea genus: O. minor, O. ceanothifolia and O. leucoxylon. Leaves and stems, as well as the bark of O. minor, were processed using a modified Clevenger apparatus. Seven essential oils were obtained and analyzed using GC-FID and GC-MS, and their chemical compositions were determined. Assays of cytotoxicity, antioxidant and free radical scavenging activity, as well as tyrosinase and elastase inhibition were performed. In total, 25 constituents were identified, the principal being sesquiterpenes, such as spathulenol caryophyllene and its oxide. The oils did not present cytotoxicity using a hemolytic model, but also did not show antioxidant activity in the DPPH assay. Essential oil from stems of O. ceanothifolia, rich in spathulenol and caryophyllene oxide, demonstrated the capacity to inhibit 49.08% of tyrosinase activity at a concentration of 100 µg/mL. This research contributes to the chemical profile analysis of the three species of Ocoteathrough chemical investigations and biological activity, which are reported for the first time here in this study.

Este trabajo realiza un estudio químico, biológico, farmacológico y cromatográfico de aceites esenciales extraídos de tres especies del género Ocotea: O. minor, O. ceanothifoliay O. leucoxylon. Las hojas y tallos, así como la corteza de O. minor, se procesaron utilizando un aparato Clevenger modificado. Se obtuvieron siete aceites esenciales y se analizaron usando GC-FID y GC-MS, y se determinaron sus composiciones químicas. Se realizaron ensayos de citotoxicidad, actividad antioxidante y de atrapamiento de radicales libres, así como inhibición de tirosinasa y elastasa. En total, se identificaron 25 componentes, siendo los principales sesquiterpenos, como el spathulenol cariofileno y su óxido. Los aceites no presentaron citotoxicidad en un modelo hemolítico y tampoco mostraron actividad antioxidante en el ensayo con DPPH. El aceite esencial de tallos de O. ceanothifolia, rico en espatulenol y óxido de cariofileno, mostró capacidad para inhibir el 49.08% de la actividad de tirosinasa a una concentración de 100 µg/mL. Esta investigación contribuye al análisis del perfil químico de las tres especies de Ocotea a través de investigaciones químicas y actividad biológica la cual se informan por primera vez.

Biocidal potential of Eugenia pyriformis essential oil in the control of Rhipicephalus (Boophilus) microplus in the free-living cycle / Potencial biocida do óleo essencial de Eugenia pyriformis Cambess no controle de Rhipicephalus (Boophilus) microplus no ciclo de vida livre

Brazil has one of the largest commercial cattle herds in the world, which naturally coexist with an enormous number of parasitic species. Southern cattle tick, Rhipicephalus (Boophilus) microplus, is among these species, interfering with animal productivity and causing losses to the beef and dairy cattle sector. The use of chemical acaricides in the control of this mite has resulted in the emergence of resistant populations. In this sense, alternative control measures using plants as sources of botanical acaricides have shown to be effective. Eugenia pyriformis Cambess is a Brazilian plant with antioxidant and antimicrobial activity; however, there are no reports on its acaricidal activity in the literature. The present study aimed to evaluate the acaricidal and larvicidal potential of E. pyriformis leaf essential oil (EO) on southern cattle tick at different stages of the reproductive cycle. E. pyriformis leaves were collected and dried, and had their EO extracted by hydrodistillation (3h) using a modified Clevenger apparatus. Chemical analysis was performed by gas chromatography coupled with mass spectrometry (GC/MS), and 32 compounds belonging to the sesquiterpene class were identified: hydrocarbons (17.98%) and oxygenated forms (81.96%), with spathulenol (43.65%) and caryophyllene oxide (12.17%) as the most common. The EO was evaluated by the Adult Immersion Test at the concentrations (500.00 to 3.12mg/mL) in which the following parameters were measured: mortality of females (%), hatchability of eggs (%), and product efficiency (%). Larvae were assessed by the Larval Packet Test at concentrations ranging from 25.00 to 0.00004mg/mL. Lethal concentrations (LC) required for killing 50 and 99.9% of adult females and larvae were determined using Probit analysis. LC50 and LC99.9 of EO were 0.06 and 24.60mg/mL and 1,208.80 and 2,538mg/mL for larvae and adult females, respectively. Action of the EO in the free-living cycle of R. (B.) microplus larvae was another parameter assessed. To this end, the larvae were deposited in pots containing Brachiaria decumbens and, after migration to the leaf apex, a solution containing LC99.9 (24.60mg/mL) of the EO was sprayed. After 24h, 72.25% of the larvae had died, indicating stability of the EO when subjected to uncontrolled temperature and humidity conditions. The mechanism of action through which the EO killed the larvae and adult females was investigated by the Bioautographic Method, which showed inhibition of 3.15mg/mL of the EO on the acetylcholinesterase (AChE) enzyme. The results found in the present experiment indicate that E. pyriformis essential oil is an alternative in the control of southern cattle tick in the larval (parasitic) and free-living cycle (non-parasitic) stages under field conditions.(AU)

O Brasil dispõe de um dos maiores rebanhos bovinos comerciais do mundo, sendo natural que junto a esse rebanho, coexista uma enorme quantidade de espécies parasitárias; dentre estes o carrapato Rhipicephalus (Boophilus) microplus que interfere na produtividade animal, causando prejuízos à pecuária de corte e leite. A utilização de acaricidas químicos no controle deste ácaro tem causado o surgimento de populações resistentes e neste sentido, controles alternativos utilizando plantas como fontes de acaricidas botânicos têm se mostrado eficazes. Eugenia pyriformis Cambess é uma planta brasileira com atividades antioxidante e antimicrobiana, entretanto não há relatos da atividade acaricida. O objetivo do presente estudo consistiu na avaliação do potencial acaricida e larvicida do óleo essencial das folhas de E. pyriformis sobre o carrapato bovino nos diferentes estágios do ciclo reprodutivo. As folhas foram coletadas, secas e o OE extraído por hidrodestilação (3 horas) em aparelho Clevenger modificado. A análise química foi realizada por cromatografia gasosa acoplada à espectrometria de massas (CG/EM) sendo identificados 32 compostos, pertencentes à classe sesquiterpenos: hidrocarbonetos (17.98%) e oxigenados (81.96%); tendo como majoritários o spathulenol (43,65%) e caryophylene oxide (12,17%). O OE foi avaliado pelo teste de imersão de adultos nas concentrações (500,00 a 3,12mg/mL) onde foram mensurados os parâmetros: mortalidade das fêmeas (%), eclodibilidade dos ovos (%) e eficiência do produto (%). As larvas foram avaliadas pelo teste de imersão larval (Larval Packet Test) nas concentrações que variaram de 25,00 a 0,00004mg/mL. Foram determinadas as concentrações letais (CLs) necessárias para matar 50 e 99,9% das fêmeas adultas e das larvas utilizando a análise de Probitos. As CL50 e CL99,9 do OE foram (0,06 e 24,60mg/mL) para as larvas e (1.208,80 e 2.538mg/mL) para as fêmeas adultas, respectivamente. Outro parâmetro avaliado em nossa pesquisa foi mensurar a ação do OE no ciclo de vida livre das larvas de R.(B.) microplus; onde as larvas foram depositadas em vasos com Brachiaria decumbens e após migração destas para o ápice das folhas, foi aspergido solução contendo a CL99,9 (24,60mg/mL) do OE. Após 24 horas, 72,25% das larvas morreram indicando que houve estabilidade do OE quando submetido a condições de temperatura e umidade não controladas. O mecanismo de ação pelo qual o OE matou as larvas e fêmeas adultas foi investigado pelo método bioautográfico, indicando uma inibição de 3,15mg/mL do óleo essencial sobre a enzima acetilcolinesterase (AChE). Os resultados encontrados no presente experimento indicaram que o óleo essencial de E. pyriformis é uma alternativa no controle do carrapato bovino no estágio larval (parasitário) e no ciclo de vida livre (estágio não parasitário) em condições de campo.(AU)

β-Caryophyllene causes remyelination and modifies cytokines expression in C57BL/6 mice with experimental autoimmune encephalomyelitis

The aim of this study is to evaluate the effect of β-Caryophyllene (BCP) on the production of IL-17, transcription factors(T-bet and GATA-3), and remyellination in C57BL/6 mice induced for experimental autoimmune encephalomyelitis(EAE), the model for studying pathogenesis and new therapies for multiple sclerosis. EAE was induced in threegroups of C57BL/6, with administration of BCP in two groups (25 and 50 mg/kg/day) by gavage, after the 10th dayof induction. At 9 days of treatment, mice were euthanized and CNS was removed for the analysis. The profiles ofIL-17, T-bet, GATA-3, and the possible remyelination properties were investigated in the central nervous system(CNS) by immunohistochemistry and Weigert–Pal–Russel’s method, respectively. BCP group (50 mg/kg/day) showeda reduction of IL-17 in brain, cerebellum, and medulla (p < 0.05) and a decrease of T-bet (p < 0.05) in medullaand cerebellum, while GATA-3 was increased (p < 0.05) in cerebellum. In both BCP-treated groups were observedremyelination and better organization of myelin. In conclusion, BCP possesses markedly in vivo anti-inflammatoryand neuroprotective activities and remyelination properties in EAE-mice.

Development and validation of a quantification method for α-humulene and trans-caryophyllene in Cordia verbenacea by high performance liquid chromatography

ABSTRACT Acheflan® herbal medicine is the first medicine developed and produced in Brazil using Cordia verbenacea DC., Boraginaceae, essential oil as a constituent. C. verbenacea has anti-inflammatory properties, which have been directly related to α-humulene and trans-caryophyllene. Currently, the quantification of α-humulene and trans-caryophyllene in C. verbenacea has only been described by GC-MS. Although this technique is widely used it cannot be directly applied to finished medicinal products since they contain aqueous constituents. In this context, the objective of this work was to develop a methodology for quantifying C. verbenacea in raw materials and in pharmaceutical formulations using liquid chromatography. The Box-Behnken experimental design was used successfully to optimize the analytical method. The method developed in this study was validated and proven to be effective in the proper separation of α-humulene and trans-caryophyllene. In addition, the developed method was applied to commercial formulations (cream and aerosol) containing C. verbenacea essential oil, which resulted in very satisfactory separation without interference from excipients. C. verbenacea oil contains four times higher concentrations of trans-caryophyllene than α-humulene. Therefore, we propose that trans-caryophyllene can be used as a marker of C. verbenacea essential oil. Evaluation of trans-caryophyllene content would be especially valuable for applications where the concentrations are very low such as in permeation and release studies of dermatological formulations.

Simultaneous Determination of Contents of 6 Components in the Oil of Blumea balsamifera by GC / 中国药房

OBJECTIVE： To establish a method for simultaneous determination of contents of β-pinene， linalool， L-camphor， L-borneol， β-caryophyllene and xanthoxylin in the oil of Blumea balsamifera. METHODS： GC method was adopted. The determination was performed on RTX-1701 capillary column （programmed temperature）. The FID detector was controlled at 240 ℃. The inlet temperature was set at 240 ℃. The carrier gas was high-purity nitrogen 3 mL/min. The the sample size was 0.5 μL， and split ratio was 50 ∶ 1. RESULTS： The linear range of β-pinene， linalool， L-camphor， L-borneol， β-caryophyllene and xanthoxylin were 0.029 7-0.267 1 mg/mL （r＝0.999 9）， 0.024 3-0.218 9 mg/mL （r＝0.999 9）， 0.126 0-1.134 0 mg/mL （r＝0.999 9）， 0.217 2-1.954 8 mg/mL （r＝0.999 9）， 0.136 3-1.226 9 mg/mL （r＝0.999 9）， 0.044 5-0.400 3 mg/mL（r＝0.999 5）， respectively. The limits of quantitation were 0.028 5， 0.008 7， 0.018 6， 0.016 8， 0.014 5， 0.042 1 mg/mL； the limits of detection were 0.009 4， 0.002 9， 0.006 1， 0.005 5， 0.004 8， 0.013 9 mg/mL， respectively. RSDs of precision， stability， reproducibility and durability tests were all lower than 3％. The average recoveries were 98.13％-101.30％（RSD＝1.20％，n＝9），98.44％-101.81％（RSD＝1.28％，n＝9），98.26％-101.05％（RSD＝1.19％，n＝9），99.08％-101.58％（RSD＝0.89％，n＝9），98.66％-101.66％（RSD＝1.17％，n＝9），98.84％-103.60％（RSD＝0.96％，n＝9）， respectively. The contents of 6 components in the sample were 14.552-46.766， 16.951-22.096， 80.597-113.115， 205.224-242.537， 47.761-135.697， 26.493-45.771 mg/g， respectively. CONCLUSIONS： The established method is simple， accurate， precise and reproducible， which can be used for simultaneous determination of contents of 6 components in the oil of B. balsamifera. It can provide reference for comprehensive evaluation and extraction technology study of the oil of B. balsamifera.

Inhibitory Effects of β-caryophyllene on Helicobacter pylori Infection: A Randomized Double-blind, Placebo-controlled Study / 대한소화기학회지

BACKGROUND/AIMS: Helicobacter pylori (H. pylori) infections, which cause a variety of gastrointestinal symptoms, are common in South Korea. Recent reports have shown a decline in the H. pylori eradication rates. β-caryophyllene is a natural bicyclic sesquiterpene that occurs in a wide range of plant species, such as cloves, basil, and cinnamon. β-caryophyllene has been reported to have anti-inflammatory and anti-bacterial effects. This study investigated the inhibitory effects of β-caryophyllene on H. pylori and its potential role as an alternative gastrointestinal drug. METHODS: This 8-week, randomized double-blind, placebo-controlled trial categorized subjects into a β-caryophyllene group (33 patients who received 126 mg/day of β-caryophyllene) and a placebo group (33 patients who received a placebo preparation). The inflammation level of H. pylori infiltration and the eradication rates were evaluated endoscopically and with the urea breath test (UBT) in both groups before and after administering the medication. The serum cytokine levels (tumor necrosis factor-α, and interleukin [IL]-1β and IL-6) were compared in both groups before and after administering the medication. RESULTS: Complete eradication was not observed in either group. Moreover, there was no significant change in the UBT and updated Sydney score. On the other hand, the β-caryophyllene group showed significant improvement in nausea (p=0.025) and epigastric pain (p=0.018), as well as a decrease in the serum IL-1β levels (p=0.038). CONCLUSIONS: β-caryophyllene improves dyspepsia symptoms and can be considered a useful supplementary treatment for gastrointestinal disease.

Inhibitory Effects of β-caryophyllene on Helicobacter pylori Infection: A Randomized Double-blind, Placebo-controlled Study / 대한소화기학회지

BACKGROUND/AIMS: Helicobacter pylori (H. pylori) infections, which cause a variety of gastrointestinal symptoms, are common in South Korea. Recent reports have shown a decline in the H. pylori eradication rates. β-caryophyllene is a natural bicyclic sesquiterpene that occurs in a wide range of plant species, such as cloves, basil, and cinnamon. β-caryophyllene has been reported to have anti-inflammatory and anti-bacterial effects. This study investigated the inhibitory effects of β-caryophyllene on H. pylori and its potential role as an alternative gastrointestinal drug.METHODS: This 8-week, randomized double-blind, placebo-controlled trial categorized subjects into a β-caryophyllene group (33 patients who received 126 mg/day of β-caryophyllene) and a placebo group (33 patients who received a placebo preparation). The inflammation level of H. pylori infiltration and the eradication rates were evaluated endoscopically and with the urea breath test (UBT) in both groups before and after administering the medication. The serum cytokine levels (tumor necrosis factor-α, and interleukin [IL]-1β and IL-6) were compared in both groups before and after administering the medication.RESULTS: Complete eradication was not observed in either group. Moreover, there was no significant change in the UBT and updated Sydney score. On the other hand, the β-caryophyllene group showed significant improvement in nausea (p=0.025) and epigastric pain (p=0.018), as well as a decrease in the serum IL-1β levels (p=0.038).CONCLUSIONS: β-caryophyllene improves dyspepsia symptoms and can be considered a useful supplementary treatment for gastrointestinal disease.

Chemical composition of essential oil from Myrcia oblongata DC and potencial antimicrobial, antioxidant and acaricidal activity against Dermanyssus gallinae (Degeer, 1778) / Composição química do óleo essencial de Myrcia oblongata DC e potencial antimicrobiano, antioxidante e acaricida contra Dermanyssus gallinae (DEGEER, 1778)

Essential oils have aroused interest in the industrial sector due to the multitude of potential applications, especially with respect their antimicrobial and antioxidant properties, among others. The objective of this study was to determine the chemical composition of the essential oil from the leaves of Myrcia oblongata DC by gas chromatography coupled to mass spectrometry (GC-MS). To evaluate the antioxidant potential of the oil by using the free radical capture method with 2,2-diphenyl-1-picryl hydrazyl (DPPH); to test the oil antimicrobial activity using the broth microdilution method; and to evaluate the repellency and fumigant potential of the oil on Dermanyssus gallinae (Degeer, 1778). The GC-MS analysis resulted in the identification of 30 oil constituents, with the bulk of the composition identified as caryophyllene oxide (22.03%) and trans-verbenol (11.94%). The oil presented moderate antioxidant activity compared to the synthetic antioxidant 2,6-di-tert-butyl-4-hydroxytoluene (BHT). Antimicrobial activity of the essential oil showed an inhibitory activity on Gram-positive bacteria, Enterococcus faecalis, Staphylococcus aureus, Bacillus subtilis and Staphylococcus epidermidis and for the yeast Candida albicans, and showed no activity against Gram-negative bacteria. All concentrations of the essential oil used in the fumigation test on D. gallinae resulted in mortality below 20%. For the repellency test, significant potential was observed for the concentration of 10%.

Os óleos essenciais tem despertado interesse no setor industrial por apresentarem multiplicidade de aplicações, destacando-se por suas propriedades antimicrobianas, antioxidantes dentre outras. Diante disto, o objetivo deste estudo foi determinar a composição química do óleo essencial das folhas de Myrcia oblongata DC pelo método de cromatografia gasosa acoplada à espectrometria de massas (CG-EM), avaliar o potencial antioxidante do óleo pelo método de captura do radical livre 2,2- difenil-1-picril hidrazil (DPPH), testar a atividade antimicrobiana pelo método de microdiluição em caldo, bem como avaliar a repelência e potencial fumigante deste óleo sobre Dermanyssus gallinae (Degeer, 1778). As análises de CG-EM resultaram na identificação de 30 constituintes, sendo majoritários o óxido de cariofileno (22.03%) e o trans-verbenol (11.94%). O óleo apresentou atividade antioxidante moderada quando comparada ao antioxidante sintético 2,6-di-tert-butil-4-hidroxitolueno (BHT). Em relação à atividade antimicrobiana, o óleo essencial demonstrou atividade inibitória para as bactérias Gram-positivas, Enterococcus faecalis, Staphylococcus aureus, Bacillus subtilis e Staphylococcus epidermidis, e para levedura Candida albicans e não apresentou atividade para bactérias Gram negativas. Todas as concentrações do óleo essencial testadas no teste de fumigação sobre D. gallinae apresentaram mortalidade inferior a 20%. Para o teste de repelência, observou-se um potencial significativo para a concentração de 10%.

Larvicidal effect of Clinopodium macrostemum essential oil extracted by microwave-assisted hydrodistillation against Culex quinquefasciatus (Diptera: Culicidae)

Abstract INTRODUCTION: In the present study, we determined the chemical composition of Clinopodium macrostemum essential oil obtained by microwave-assisted hydrodistillation and its effect on the growth and development of Culex quinquefasciatus mosquito larvae. METHODS: The essential oil compounds were identified by gas chromatography-mass spectrometry analysis, and bioassays were conducted to evaluate the influence on the developmental stages of early second instar larvae of Cx. quinquefasciatus until the emergence of adults, using essential oil concentrations of 50, 100, 200, 400, and 800mg/L. RESULTS: The gas chromatography-mass spectrometry analyses revealed that the leaf essential oil of C. macrostemum contained 32 compounds and the major chemical compounds identified were linalool (55.4%), nerol (6.4%), caryophyllene (6.25%), menthone (5.8%), geraniol acetate (4.1%), terpineol (3.7%), and pulegone (2.8%). The essential oil yield obtained by microwave-assisted hydrodistillation was 0.8% at 20 min. The treatments showed lethal concentrations (LC50 and LC90) of 22.49 and 833.35mg/L, respectively, after the final measurement of the total number of dead larvae (second, third, and fourth instars), and LC50 and LC90 of 6.62 and 693.35mg/L, respectively, at the end of the experimental period. The essential oil inhibited the growth and development of the mosquito larvae by 32% (relative growth index = 0.68) at 50mg/L, and up to 47% (relative growth index = 0.53) at 800mg/L. CONCLUSION: The present study demonstrated the larvicidal effect of C. macrostemum essential oil on Cx. quinquefasciatus, which can be attributed to the oxygenate compounds obtained by the extraction method.

First phytochemical description of essential oils from Piper cachimboense (Piperales, Piperaceae) / Primeira descrição fitoquímica de óleos essenciais de Piper cachimboense (Piperales, Piperaceae)

Piper cachimboense is recorded only for the Amazon region of Brazil and Colombia, and the objective of this study was to report the first phytochemical assessment of the composition of the essential oils (EOs) from this species collected in the Amazon rainforest, in Novo Progresso, Pará State, Brazil. Samples of leaves were subjected to hydrodistillation in a Clevenger-type apparatus. The chemical identification was carried out by gas chromatography. The yield of oils was of 11.03 ± 5.94% for fresh leaves, and 1.07 ± 0.27% for dry leaves. The analysis showed 36 volatile compounds from fresh leaves and 49 from dried leaves. Main constituents in EOs of both fresh and dried leaves from P. cachimboense were (E)-caryophyllene, germacrene-D, -amorfene, -cadinene and apiole.

Piper cachimboense é registrada apenas para a região amazônica do Brasil e Colômbia, e o objetivo deste estudo foi relatar, pela primeira vez, a composição fitoquímica dos óleos essenciais (OEs) desta espécie coletada na floresta amazônica, em Novo Progresso/PA, Brasil. Amostras de folhas foram submetidas a hidrodestilação em aparelho tipo Clevenger. A identificação química foi realizada por cromatografia gasosa e o rendimento dos óleos foi de 11,03 ± 5,94% para as folhas frescas e de 1,07 ± 0,27% para as folhas secas. A análise mostrou 36 compostos voláteis para folhas frescas e 49 para folhas secas. Os constituintes principais dos OEs de folhas frescas e secas de P. cachimboense foram (E)-cariofileno, germacreno-D, -amorfeno, -cadineno e apiol.

Essential oil of Pterodon polygalaeflorus Benth attenuates nociception in mice

Essential oils (EO) are volatile liquids responsible for the aroma of plants. Pterodon polygalaeflorus seeds have received widespread use in folk medicine for the treatment of inflammatory diseases. For this reason and because Pterodon polygalaeflorus seeds have great EO content, which is frequently pharmacologically active, the present study aimed to evaluate the antinociceptive effect of EO from Pterodon polygalaeflorus (EOPPgfl) and its acute toxic effects. The EEOPPgfl sample, which was extracted by steam distillation of the seeds, had a yield of 2.4% of the seeds weight and had, as major constituents, beta-elemene (48.19%), trans-caryophyllene (19.51%), and epi-bicyclosesquiphellandrene (12.24%). The EOPPgfl sample showed mild acute toxicity and its calculated median lethal dose (LD50) was 3.38 g/kg. EOPPgfl (20-60 mg/kg) showed antinociceptive activity as evidenced by several tests and inhibited writhing induced by acetic acid. The maximum effect was obtained with the 30 mg/kg dose and at 60 min after its administration. EOPPgfl also decreased formalin-induced nociception, as verified by the inhibition of the first and second phase of the formalin test. At 30 mg/kg, EOPPgfl also decreased thermally stimulated nociception. Nociception may be related to inflammatory and antiedematogenic activity and at doses ranging 10-100 mg/kg, EOPPgfl blocked dextran- and carrageenan-induced edema. The results demonstrated that EOPPgfl presented, at doses approximately 100 times smaller than LD50, an antinociceptive effect that probably was due to anti-inflammatory activities.

Chemical Composition, Anticancer, Anti-neuroinflammatory, and Antioxidant Activities of the Essential Oil of Patrinia scabiosaefolia / 中国结合医学杂志

<p><b>OBJECTIVE</b>To study the chemical composition, anticancer, anti-neuroinflflammatory, and antioxidant activities of the essential oil of Patrinia scabiosaefolia (EO-PS).</p><p><b>METHODS</b>Patrinia scabiosaefolia was analyzed by gas chromatography-mass spectrometry. Eight human carcinoma cell lines, including SGC-7901, AGS, HepG2, HT-29, HCT-8, 5-FU/HCT-8, HeLa, and MDA-MB-231, were assessed by methylthiazolyldiphenyltetrazolium bromide (MTT) assay. Anti-neuroinflflammatory activity was assessed by production of interleukin (IL)-1β and IL-6 induced by lipopolysaccharide in BV-2 cells (microglia from mice). The antioxidant activity was evaluated with a 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging assay.</p><p><b>RESULTS</b>Forty-four components, representing 83.919% of the total oil, were identifified in the EO-PS. The major constituents were caryophyllene oxide (12.802%), caryophyllene (6.909%), α-caryophyllene (2.927%), β-damascenone (3.435%), calarene (5.621%), and phenol (3.044%). The MTT assay showed that the EO-PS exhibited significant dose-dependent growth inhibition in the 50-200 μg/mL dilution range. The EO-PS exhibited a dose-dependent scavenging activity against the DPPH radical, with an half of maximal inhibitory concentration 1.455 mg/mL.</p><p><b>CONCLUSIONS</b>The EO-PS possesses a wide range of antitumor, anti-neuroinflflammatory and antioxidant activities, suggesting that it may be a good candidate for further investigations of new bioactive substances.</p>

Chemical composition, antimicrobial and antioxidant activities of Echinophora platyloba essential oil / Composición química y actividades antimicrobianas y antioxidantes del aceite esencial de Echinophora platyloba

Objetivo: Echinophora platyloba se utiliza tradicionalmente como agente antimicrobiano con el fin de preservar los productos caseros de deterioro. El objetivo de este estudio fue evaluar la composición química del aceite esencial, actividad antimicrobiana y antioxidante del aceite esencial de E. platyloba de la provincia de Shahr-e-Kord. Materiales y métodos: la composición química del aceite esencial de E. platyloba mediante técnicas de GC-MS y GC y evaluar su efecto antibacteriano frente a Staphylococcus aureus, Salmonella enterica y Helicobacter pylori por ensayos de difusión en disco y de micro dilución en caldo. La actividad antioxidante del aceite esencial de E. platyloba se evaluó por los radicales ABST. β-ocimeno y α-cariofileno eran los componentes principales del aceite esencial de E. platyloba. El aceite esencial mostró la actividad antibacteriana prometido contra S. aureus, seguido de S. enterica y H. pylori. El aceite esencial presenta actividad antioxidante del aceite esencial mostró la IC50 de 0. 32 mg/ml que fue mayor que la IC50 de ácido ascórbico (0.20 mg/ml). En conclusión : Aceite esencial de E. platyloba ha se recomienda ß-ocimeno y quimiotipo α-cariofileno y su uso como agentes antioxidantes y antibacterianas como sus usos tradicionales.

Objective: Echinophora platyloba is traditionally used as antimicrobial agent in order to preserve the home-made products from deterioration. The aim of this study was to evaluate chemical composition of essential oil, antimicrobial and antioxidant activity of E. platyloba essential oil from Shahr-E-Kord city, Chaharmahal and Bakhtiari Province. Materials and methods: chemical composition of E. platyloba essential oil by GC and GC-MS techniques and evaluate its antibacterial effect against Staphylococcus aureus, Salmonella enterica and Helicobacter pylori by disc diffusion and micro broth dilution assays. The antioxidant activity of E. platyloba essential oil was evaluated by ABST radicals. β-ocimene and α-caryophyllene were the main components of E. platyloba essential oil. The essential oil showed the promised antibacterial activity against S. aureus, followed by S. enterica and H. pylori. The antioxidant activity evaluation of essential oil showed the IC50 of 0.32 mg/ml that was higher than the IC50 of ascorbic acid (0.20 mg/ml). In conclusion , E. platyloba essential oil has β-ocimene and α-caryophyllene chemotype and its use as antioxidant and antibacterial agents is recommended as its traditional uses.

Comparative toxicity of essential oil and blends of selected terpenes of Ocotea species from Pernambuco, Brazil, against Tetranychus urticae Koch

ABSTRACT Essential oils from the leaves of two species of the genus Ocotea that occur in the Atlantic Forest in the state of Pernambuco, Brazil, were analyzed using gas chromatography-mass spectrometry. The acaricidal activity of these oils as well as 11 selected components and blends were evaluated in fumigation and residual contact tests against the two-spotted spider mite (Tetranychus urticae). Sixty-seven constituents were identified, totaling 97.3 ± 0.3% and 97.8 ± 0.5% of the oils from O. duckei and O. glomerata, respectively. Sesquiterpene was the dominant class. The compounds β-caryophyllene (18.6 ± 0.1%) and aromadendrene (17.3 ± 0.6%) were the main constituents of the oils from O. duckei and O. glomerata, respectively. Acaricidal action varied depending on the method employed, species and chemical nature of the selected constituents. The mites were susceptible to the oils and chemical constituents using the fumigation method. The O. duckei oil was respectively 2.5-fold and 1.5-fold more toxic than the O. glomerata oil using the fumigation and residual contact methods. Among the selected constituents, β-caryophyllene was the most toxic, independently of the method employed. The individual toxicity of the selected compounds and their blends as well as the role of these constituents in the overall toxicity of the essential oils are also discussed.

Chemical composition and antibacterial activity of essential oil from leaves of Croton heliotropiifolius in different seasons of the year

ABSTRACT This paper reports the first study of the variation of the chemical composition and abundance of the essential oil of Croton heliotropiifolius, in four seasons, and the evaluation of its antibacterial activity. Essential oil obtained from leaves of C. heliotropiifolius were analyzed by GC/MS and evaluated against eight bacteria strains by broth microdilution method. The chemical constituents identified were the same in all samples, but with different proportions. The total percentages identified were 96.58% in summer, 92.08% in autumn, 98.44% in winter and 90.78% in spring. The majors constituents are β-caryophyllene, bicyclogermacrene, germacrene-D, limonene and 1,8-cineole. β-Caryophyllene was the major compound in all samples. The results of the antibacterial evaluations showed weak to moderate activity against the analyzed strains. In all analyzes was observed that essential oil sample collected in summer stands out from the others, displaying stronger activity against Gram-positive as Gram-negative bacteria.