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)

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%.

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 and antibacterial activity of essential oils from the rhizomes of cyperus papyrus L. grown in South Africa / Composición química y actividad antibacterial de los aceites esenciales de los rizomas de cyperus papurus L., crecidos en Sudafrica

Essential oils hydrodistilled from the rhizomes of Cyperus papyrus L. growing wild in two localities (KwaDlangezwa and Richard’s Bay) of uMhlathuze City, KwaZulu-Natal Province, South Africa has been studied. The major components of KwaDlangezwa oil were caryophyllene oxide (12.7 percent), cyperene (10.2 percent) and 1,8-cineole (8.4 percent). The oil of Richard’s Bay comprised mainly of caryophyllene oxide (24.4 percent), humulene epoxide II (13.2 percent), aristolene (9.1 percent) and aromadendrene epoxide II (7.3 percent). The antibacterial activity of the oils was assayed using agar-disc diffusion and broth-microdilution methods. The minimum inhibitory concentration (MIC) revealed that the oil samples inhibited the growth of Staphylococcus aureus (ATCC 3983 and ATCC 6538), with MIC of 1.25 and 0.31 mg/mL for each oil. Streptococcus faecalis (ATCC 29212; MIC of 1.25 and 0.6 mg/mL, respectively) and Escherichia coli (ATCC 4983; MIC of 1.25 mg/mL for both oils). Only the Richard Bay oil showed activity against Bacillus cereus and Bacillus pumilus with MIC of 1.25mg/mL, respectively.

Los aceites esenciales hidrodestilados de los rizomas de Cyperus papyrus L., que crecen en dos localidades (KwaDlangezwa y Bahía Richard) de la ciudad de uMhlathuze, la provincia KwaZulu-Natal, de Sudafrica han sido estudiados. Los mayores componentes del aceite de KwaDlangezwa fueron óxido de cariofileno (12,7 por ciento), cipereno (10,2 por ciento) y 1,8-cineol (8,4 por ciento). El aceite de la bahía de Richard consistió principalmente cariofileno (24,4 por ciento), epóxido II de humuleno (13,2 por ciento), aristoleno (9,1 por ciento) y epóxido II de aromandreno (7,3 por ciento). La actividad antibacterial de los aceites fueron ensayados utilizando la difusión en discos de agar y el método de microdilución en caldo. La concentración mínima inhibitoria (CMI) reveló que las muestras inhibieron el crecimiento de Staphylococcus aureus (ATCC 3983 y ATCC 6538), con una MIC de 1,25 y 0,31 mg/ml de cada aceite. Streptococcus faecalis (ATCC 29212; CMI de 1,25 y 0.6 mg/mL, respectivamente) y Escherichia coli (ATCC 4983; CMI de 1,25 mg/mL para ambos aceites). Solo el aceite de la bahía Richard mostró actividad contra Bacillus cereus y Bacillus pumilis con CMI de 1,25 mg/mL, respectivamente.

Essential oils and major compounds of Hedychium coronarium Koenig (Zingiberaceae) against pathogenic yeast of Candida and Cryptococcus genus / Óleos essenciais e compostos majoritários de Hedychium coronarium Koenig (Zingiberaceae) contra leveduras patogênicas dos gêneros Candida e Cryptococcus

Among the major causative agents of invasive fungal infections stands out the opportunistic yeasts of Candida and Cryptococcus. Regarding the problem of the high incidence of infections by these agents and the difculty of treating the low stockpile of antifungal drugs and the high toxicity of most therapies, the search for new antifungal compounds has been highlighted in recent decades. Hedychium coronarium, popularly known as "lírio-do-brejo" or "gengibre-branco" features several previously reported biological activities, including antimicrobial activity. Compound 1.8-cineole is the major compound in essential oil extracted from roots of H. coronarium, while caryophyllene oxide presents itself as the major in essential oil extracted from leaves of this plant. Our data show strong antifungal activity of compounds, against species of Candida albicans, Candida parapsilosis, Candida krusei, Cryptococcus neoformans and Cryptococcus gattii, with minimal inhibitory concentration and minimal fungicidal concentration equal to 0.2 % (v/v) for essential oil extracted from roots, while the essential oil extracted from leaves showed no activity against yeasts. The caryophyllene oxide showed higher antifungal activity for Cryptococcus spp. Thus, our results showed that the essential oil of rhizome is a promising antifungal agent against pathogenic yeasts.(AU)

Candida spp e Cryptococcus spp estão classifcadas entre os maiores causadores de infecções fúngicas invasivas em pacientes imunocomprometidos. Diante a alta incidência destas infecções por estes agentes e a difculdade do sucesso no tratamento, decorrente do baixo arsenal de fármacos antifúngicos e da alta toxicidade presente na maioria dos esquemas terapêuticos, a busca por novos compostos antifúngicos tem sido alvo de diversos estudos nas últimas décadas. Hedychium coronarium, popularmente conhecido como "lírio-do-brejo" ou "gengibre-branco", apresenta diversas atividades biológicas já descritas, entre elas a atividade antimicrobiana. O composto 1.8-Cineol é o composto majoritário presente no óleo essencial extraído de raízes de H. coronarium e o composto óxido de cariofleno é o composto majoritário extraído das folhas desta planta. Nossos resultados mostram que os compostos extraídos de H. coronarium apresentam forte atividade contra Candida albicans, Candida parapsilosis, Candida krusei, Cryptococcus neoformans e Cryptococcus gattii, com valores de concentração inibitória minima e concentração fungicida minima igual a 0,2 % (v/v) para o óleo essencial extraído das raízes, enquanto que o óleo essencial extraído das folhas, não mostrou atividade contras as leveduras. O composto óxido de cariofleno mostrou maior atividade antifúngica para Crytopcoccus spp. Assim, nossos dados mostraram que o óleo essencial extraído das raízes de H. coronarium, é um agente antifúngico promissor contra leveduras patogênicas.(AU)

Leaf and fruit essential oil compositions of Pimenta guatemalensis (Myrtaceae) from Costa Rica / Aceites volátiles de hojas y frutos de Pimenta guatemalensis (Myrtaceae) de Costa Rica

Pimenta is a genus of flowering plants in the Myrtaceae family, which has about 15 species, mostly found in the Caribbean region of the Americas. Commonly used for culinary and medicinal purposes, the best known commercial species are allspice, P. dioica (P. officinalis) and bay rum, P. racemosa, but there is little information concerning P. guatemalensis. The aim of the present study was to identify the chemical composition of the leaf and fruit essential oils of P. guatemalensis. The extraction of essential oils of P. guatemalensis growing wild in Costa Rica was carried out by the hydrodistillation method at atmospheric pressure, using a modified Clevenger type apparatus. The chemical composition of the oils was analyzed by capillary gas chromatographyflame ionization detector (GC/FID) and gas chromatography-mass spectrometry (GC/MS) using the retention indices on DB-5 type capillary column. A total of 103 and 63 compounds were identified in the leaf and fruit oils, respectively, corresponding to 96.8% and 86.1% of the total amount of the oils. The leaf oil consisted mainly of eugenol (72.8%), and mono- and sesquiterpene hydrocarbons (18.2%). Among terpenes the major components were β-caryophyllene (8.2%) and terpinolene (3.0%). The fruit oil also consisted mainly of eugenol (74.7%) and minor amounts of oxygenated mono- and sesquiterpenes (7.3%), mainly caryophyllene oxide (3.3%). This is the first report of the chemical composition of the essential oils obtained from this plant species. Rev. Biol. Trop. 63 (1): 303-311. Epub 2015 March 01.

Pimenta es un género de plantas perteneciente a la familia Myrtaceae que contiene cerca de 15 especies, la mayoría ubicadas en las regiones del Caribe del Continente Americano, donde es utilizado con propósitos culinarios y medicinales. Las especies comerciales mejor conocidas son “pimienta de Jamaica” (P. dioica o P. officinalis) y “bay-rum” (P. racemosa) y existe muy poca información científica acerca de la especie P. guatemalensis. Cuando las hojas y frutos son triturados, desprenden un aroma de composición desconocida. El objetivo del presente estudio fue identificar la composición química de los aceites esenciales de las hojas y frutos de P. guatemalensis. La extracción de los aceites esenciales de P. guatemalensis, una especie arbórea silvestre en Costa Rica, se efectuó mediante el método de hidrodestilación a presión atmosférica, empleando un aparato de vidrio de tipo Clevenger. Se analizó la composición química de los aceites esenciales mediante cromatografía de gases con detector de ionización de flama (GC/FID) y cromatografía de gases acoplada a un detector de masas (GC/MS) y, utilizando índices de retención en una columna cromatográfica capilar tipo DB-5. En los aceites de hojas se identificaron 103 y en los de frutos 63 compuestos, correspondiendo a 96.8% y 86.1%, respectivamente, de los constituyentes totales. El aceite de las hojas está constituido principalmente por compuestos de naturaleza fenilpropanoide (72.9%) y de hidrocarburos monoterpénicos y sesquiterpénicos (18.2%). Los componentes mayoritarios del aceite de las hojas se identificaron como eugenol (72.8%), β-cariofileno (8.2%) y terpinoleno (3.0%). El aceite de los frutos está constituido principalmente por eugenol (74.7%), monoterpenos y sesquiterpenos oxigenados (7.3%) principalmente óxido de cariofileno (3.3%). Este es el primer informe acerca de la composición química de aceites esenciales obtenidos a partir de esta especie vegetal.

Light affects Varronia curassavica essential oil yield by increasing trichomes frequency

Light can act on essential oil yield directly on synthesis of secondary metabolites, or indirectly on plant growth. Varronia curassavica Jacq., Boraginaceae, is a native medicinal species from Brazil known as “erva-baleeira”, with anti-inflammatory activity related to its essential oil. Despite pharmacological evidences of this species and its economic importance for herbal medicine production, little is known about the effect of light on growth and essential oil production. This study aimed to analyze the influence of different irradiances on growth, frequency of trichomes, essential oil yield and composition of V. curassavica. The irradiance affected plant growth, but no significant alteration on leaf biomass was detected. The increase in essential oil content under higher irradiance reflected on essential oil yield, and is associated with higher frequency of glandular, globular trichomes. The essential oil composition, rich in caryophyllene derivatives was affected by irradiance, but α-humulene, the constituent of pharmaceutical interest, remained unchanged.

Gastroprotective activity of caryophyllene oxide: the role of nitric oxide, prostaglandins and sulfhydryls.

The present study was carried out to evaluate the gastroprotective effect of caryophyllene oxide, and investigate the gastroprotective mechanism. For this purpose, Wistar rats received vehicle, caryophyllene oxide (10-100 mg/kg) or carbenoxolone (1-100 mg/kg, used as the reference drug). Thirty minutes later absolute ethanol was given orally, and 2 h later the stomach was dissected and the damaged area measured. In other experiments, the rats received L-NAME (70 mg/kg, i. p.), indomethacin (10 mg/kg, s. c.), and N-ethylmaleimide (10 mg/kg, s. c.), before the administration of the caryophyllene oxide (100 mg/kg) or carbenoxolone (100 mg/kg). Two control groups were included in these evaluations. Again, thirty minutes later absolute ethanol was given orally, and 2 hours later the animals were sacrificed to measure the ulcer index. Treatment of rats with caryophyllene oxide and carbenoxolone elicited a dose-dependent gastroprotective effect. The gastroprotection observed with the administration of caryophyllene oxide was attenuated in rats pretreated with the inhibitors. This suggests that the gastroprotective mechanism of action of caryophyllene oxide involves NO, prostaglandins and sulfhydryl groups. In the case of carbenoxolone, the partial participation of NO, prostaglandins and sulfhydryls was observed.

Phytochemical screening, antinociceptive and anti-inflammatory effects of the essential oil of Myrcia pubiflora in mice

This report aimed to investigate the chemical composition and possible antinociceptive and anti-inflammatory effects of the essential oil from fresh leaves of Myrcia pubiflora DC., Myrtaceae (EOMP), through different experimental tests. The essential oil of M. pubiflora (EOMP) was obtained by hydrodistillation, analyzed by GC-MS, and tested at doses of 25, 50, and 100 mg/kg (i.p.) in three different tests of nociception (acetic acid-induced writhing test, formalin test, and hot plate test) and one test of inflammation (leukocyte migration to the peritoneal cavity) in order to evaluate the motor activity in mice treated with EOMP. The major component of EOMP was caryophyllene oxide (22.16 percent). This oil significantly reduced the number of writhes in an acetic acid test and the time spent licking the paw at the second phase of the formalin test. Furthermore, EOMP inhibited the carrageenan-induced leukocyte migration to the peritoneal cavity. However, administration of EOMP did not alter reaction time in the hot plate test, and did not affect the motor coordination test. These results indicate antinociceptive and anti-inflammatory properties of EOMP probably mediated via inhibition of inflammatory mediator synthesis or other peripheral pathway.

Sesquiterpenoids of Senecio bonariensis Hook. & Arn., Asteraceae / Sesquiterpenóides de Senecio bonariensis Hook. & Arn., Asteraceae

Das folhas de Senecio bonariensis Hook. & Arn. foram isolados três sesquiterpenóides. β-Cariofileno (1), óxido de β-cariofileno (2) e germacreno D (3) foram identificados por CG-IE-EM, IV, ¹H and 13C-RMN. A importância ecológica e quimiotaxionômica para o gênero Senecio é discutida, assim como a correlação biossintética entre as substâncias isoladas. As substâncias 1 e 2 tiveram sua atividade antimicrobiana avaliada pelo método de microdiluição em caldo contra cepas bacterianas e fúngicas. Ambas não inibiram o crescimento microbiano nas concentrações testadas.

From the leaves of Senecio bonariensis Hook. & Arn. three sesquiterpenoids were isolated. β-caryophyllene (1), β-caryophyllene oxide (2) and germacrene D (3) were characterized by GC-EI-MS, IR, ¹H and 13C-NMR data. Their ecological and chemotaxonomical significance for the genus Senecio are discussed, as well as the biosynthetic correlation between the isolated substances. The antimicrobial activity of substances 1 and 2 were evaluated by the microdilution method against bacterial and fungal strains. Both compounds did not inhibit the microorganism growth at the tested concentrations.