RESUMO

Introduction: Lung cancer is the most commonly diagnosed and the main cause of cancer death, usually related to cigarette smoking. Furthermore, the microbiota of people exposed to cigarette smoke can be modified, making it difficult to eliminate opportunistic microorganisms. The leaves of Eugenia pyriformis are a by-product of fruit production and, to date, there have been no studies addressing the antiproliferative, anti-inflammatory, and antimicrobial activities. Objective: Investigate the antimicrobial, Nitric Oxide (NO)-production inhibition, and antiproliferative activities of the essential oil from E. pyriformis leaves and its possible effect on the treatment and prevention of damage caused by tobacco. Methods: The essential oil (EO) was obtained by hydrodistillation (3 h). Its chemical composition was investigated by GC-MS. It was proposed to investigate antiproliferative activity against human tumor cell lines, namely, breast adenocarcinoma (MCF-7), lung (NCI-H460), cervical (HeLa), and hepatocellular (HepG2) carcinomas. A non-tumor primary culture from pig liver (PLP2) was also tested. The EO capacity to inhibit nitric oxide (NO) production was evaluated by a lipopolysaccharide stimulated murine macrophage cell line. Antibacterial and antifungal activities against opportunistic pathogens were investigated against seven strains of bacteria and eight fungi. Results: The results indicated the presence of 23 compounds in the essential oil, the majority were spathulenol (45.63%) and ß-caryophyllene oxide (12.72%). Leaf EO provided 50% inhibition of nitric oxide production at a concentration of 92.04 µg mL-1. The EO also demonstrated antiproliferative activity against all human tumor cell lines studied, with GI50 values comprised between 270.86 and 337.25 µg mL-1. The essential oil showed antimicrobial potential against the bacteria Listeria monocytogenes (Murray et al.) Pirie (NCTC 7973) and Salmonella Typhimurium ATCC 13311 (MIC 1870 µg mL-1) and fungi Aspergillus versicolor ATCC 11730, Aspergillus ochraceus ATCC 12066, Penicillium ochrochloron ATCC 90288, Penicillium verrucosum var. cyclopium (Westling) Samson, Stolk & Hadlok (food isolate) (MIC 1870 µg mL-1) and Trichoderma viride Pers. IAM 5061 (1,400 µg mL-1). Conclusion: The demonstrated anti-inflammatory, antiproliferative, and antimicrobial activities in the leaves of E. pyriformis can add value to the production chain of this plant, being a possible option for preventing and combating cancer, including lung cancer.

RESUMO

Pain is the most frequent symptom of disease. In treating pain, a lower incidence of adverse effects is found for paracetamol versus other non-steroidal anti-inflammatory drugs. Nevertheless, paracetamol can trigger side effects when taken regularly. Combined therapy is a common way of lowering the dose of a drug and thus of reducing adverse reactions. Since ß-caryophyllene oxide (a natural bicyclic sesquiterpene) is known to produce an analgesic effect, this study aimed to determine the anti-nociceptive and gastroprotective activity of administering the combination of paracetamol plus ß-caryophyllene oxide to CD1 mice. Anti-nociception was evaluated with the formalin model and gastroprotection with the model of ethanol-induced gastric lesions. According to the isobolographic analysis, the anti-nociceptive interaction of paracetamol and ß-caryophyllene oxide was synergistic. Various pain-related pathways were explored for their possible participation in the mechanism of action of the anti-nociceptive effect of ß-caryophyllene oxide, finding that NO, opioid receptors, serotonin receptors, and K+ATP channels are not involved. The combined treatment showed gastroprotective activity against ethanol-induced gastric damage. Hence, the synergistic anti-nociceptive effect of combining paracetamol with ß-caryophyllene oxide could be advantageous for the management of inflammatory pain, and the gastroprotective activity should help to protect against the adverse effects of chronic use.

RESUMO

This study aimed to evaluate the antibacterial and inhibitory action of NorA, Tet(K), MsrA and MepA efflux pumps in S. aureus strains using the sesquiterpenes named trans-caryophyllene and caryophyllene oxide, both isolated and encapsulated in liposomes. The antibacterial and inhibitory action of these efflux pumps was evaluated through the serial microdilution test in 96-well microplates. Each sesquiterpene and liposome/sesquiterpene was combined with antibiotics and ethidium bromide (EtBr). The antibiotics named norfloxacin, tetracycline and erythromycin were used. The 1199 B, IS-58, RN4220 and K2068 S. aureus strains carrying NorA, Tet(K), MsrA and MepA, respectively, were tested. In the fluorescence measurement test, K2068 S. aureus was incubated with the sesquiterpenes and EtBr, and the fluorescence emission by EtBr was measured. The tested substances did not show direct antibacterial activity, with MIC >1024 µg/mL. Nonetheless, the isolated trans-caryophyllene and caryophyllene oxide reduced the MIC of antibiotics and EtBr, indicating inhibition of NorA, Tet(K) and MsrA. In the fluorescence test, these same sesquiterpenes increased fluorescence emission, indicating inhibition of MepA. Therefore, the sesquiterpenes named trans-caryophyllene and caryophyllene oxide did not show direct antibacterial action; however, in their isolated form, they showed possible inhibitory action on NorA, Tet(K), MsrA and MepA efflux pumps. They may also act in antibiotic potentiation. Further studies are needed to identify the mechanisms involved in antibiotic potentiation and efflux pump inhibitory action.

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RESUMO

Several Baccharis species are popularly known in traditional medicine as "carquejas", "vassouras", "ervas-santas" and "mio-mios", and are used as anti-inflammatories, digestives, and diuretics. This study aimed to investigate the chemical compositions and cytotoxic activities of essential oils (EOs) of six Baccharis species belonging to subgenus Coridifoliae, namely B. albilanosa, B. coridifolia, B. erigeroides, B. napaea, B. ochracea, and B. pluricapitulata. GC/MS analyses of the EOs showed that the oxygenated sesquiterpenes spathulenol (7.32-38.22 %) and caryophyllene oxide (10.83-16.75 %) were the major components for all the species. The EOs of almost all species were cytotoxic against cancer (BT-549, KB, SK-MEL and SK-OV-3) and normal kidney (VERO and LLC-PK1) cell lines, whereas B. erigeroides EO showed cytotoxicity only against LLC-PK1. This article augments the current knowledge about the chemical-biological properties of Baccharis subgenus Coridifoliae and discusses the therapeutic potentials of these economically unexploited plants.

RESUMO

The essential oils (EOs) of Guatteria schomburgkiana (Gsch) and Xylopia frutescens (Xfru) (Annonaceae) were obtained by hydrodistillation, and their chemical composition was evaluated by gas chromatography-mass spectrometry (GC/MS). Herbicide activity was measured by analyzing the seed germination percentage and root and hypocotyl elongation of two invasive species: Mimosa pudica and Senna obtusifolia. The highest yield was obtained for the EO of Xfru (1.06%). The chemical composition of Gsch was characterized by the presence of the oxygenated sesquiterpenes spathulenol (22.40%) and caryophyllene oxide (14.70%). Regarding the EO of Xfru, the hydrocarbon monoterpenes α-pinene (35.73%) and ß-pinene (18.90%) were the components identified with the highest concentrations. The germination of seeds of S. obtusifolia (13.33 ± 5.77%) showed higher resistance than that of seeds of M. pudica (86.67 ± 5.77%). S. obtusifolia was also more sensitive to the EO of Xfru in terms of radicle (55.22 ± 2.72%) and hypocotyl (71.12 ± 3.80%) elongation, while M. pudica showed greater sensitivity to the EO of Gsch. To screen the herbicidal activity, the molecular docking study of the major and potent compounds was performed against 4-hydroxyphenylpyruvate dioxygenase (HPPD) protein. Results showed good binding affinities and attributed the strongest inhibitory activity to δ-cadinene for the target protein. This work contributes to the study of the herbicidal properties of the EOs of species of Annonaceae from the Amazon region.

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RESUMO

Sesquiterpene compounds are applied as permeation promoters in topical formulations. However, studies exploring their impact on nanostructured systems, changes in permeation profile, and consequently, its biological activity are restricted. This study aimed to investigate the correlation between the skin permeation of the major sesquiterpenes, beta-caryophyllene, and caryophyllene oxide from the oleoresin of Copaifera multijuga, after delivery into topical nanoemulgels, and the in vivo antiedematogenic activity. First, ten nanoemulgels were prepared and characterized, and their in vitro permeation profile and in vivo anti-inflammatory activity were evaluated. In equivalent concentrations, ß-caryophyllene permeation was greater from oleoresin nanoemulgels, resulting in greater in vivo antiedematogenic activity. However, an inverse relationship was observed for caryophyllene oxide, which showed its favored permeation and better in vivo anti-inflammatory effect carried as an isolated compound in the nanoemulgels. These results suggest that the presence of similar compounds may interfere with the permeation profile when comparing the profiles of the compounds alone or when presented in oleoresin. Furthermore, the correlation results between the permeation profile and in vivo antiedematogenic activity corroborate the establishment of beta-caryophyllene as an essential compound for this pharmacological activity of C. multijuga oleoresin.

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RESUMO

Tradescantia pallida is a herbaceous plant with promising compounds in its composition that can be applied in several areas such as agronomic, pharmaceutical and chemical. However, further studies on this plant are needed in order to characterise it phytochemically, pharmacologically and toxicologically. In this sense, the present study aimed to verify the unprecedented identification of its essential oil (EO) components. The EO extraction of T. pallida aerial parts was performed by hydrodistillation in a Clevenger apparatus (5 h), and the chemical analysis by gas chromatography coupled to mass spectrometry. The oxygenated sesquiterpene was the dominant class in EO composition and spathulenol (19.56%) was the principal identified compound, followed by caryophyllene oxide (18.84%), ß-caryophyllene (13.65%) and α-copaene (6.08%). The chemical identification of sesquiterpene compounds (oxygenated and hydrocarbons) in EO contributes to the understanding of the biological activities evidenced by T. pallida reported by literature.

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RESUMO

In the late phase of Trypanosoma cruzi infection, parasite persistence and an exaggerated immune response accompanied by oxidative stress play a crucial role in the genesis of Chronic Chagasic Cardiomyopathy (CCC). Current treatments (Benznidazole (BNZ) and Nifurtimox) can effect only the elimination of the parasite, but are ineffective for late stage treatment and for preventing heart damage and disease progression. In vivo trypanocidal and cardioprotective activity has been reported for Lippia alba essential oils (EOs), ascribed to their two major terpenes, limonene and caryophyllene oxide. To investigate the role of antioxidant and immunomodulatory mechanisms behind these properties, chronic-T. cruzi-infected rats were treated with oral synergistic mixtures of the aforementioned EOs. For this purpose, the EOs were optimized through limonene-enrichment fractioning and by the addition of exogenous caryophyllene oxide (LIMOX) and used alone or in combined therapy with subtherapeutic doses of BNZ (LIMOXBNZ). Clinical, toxicity, inflammatory, oxidative, and parasitological (qPCR) parameters were assessed in cardiac tissue. These therapies demonstrated meaningful antioxidant and immunomodulatory activity on markers involved in CCC pathogenesis (IFN-γ, TNF-α, IL-4, IL-10, and iNOS), which could explain their significant trypanocidal properties and their noteworthy role in preventing, and even reversing, the progression of cardiac damage in chronic Chagas disease.

RESUMO

Cancer treatment frequently carries side effects, therefore, the search for new selective and effective molecules is indispensable. Hymenaea courbaril L. has been used in traditional medicine in South America to treat several diseases, including prostate cancer. Leaves' extracts from different polarities were evaluated using the 3-(4,5-methyl-thiazol-2-yl)-2,5-diphenyl-tetrazolium bromide (MTT) cell viability assay to determine the cytotoxicity in prostate p53-null cells, followed by bio-guided fractionations to obtain the most cytotoxic fraction considering the selectivity index. The most cytotoxic fraction was analyzed by GC/MS to identify the active compounds. The majority compound, caryophyllene oxide, induced early and late apoptosis, depolarized the mitochondrial membrane, leading to several morphological changes and shifts in apoptotic proteins, and caspases were evidenced. Depolarization of the mitochondrial membrane releases the pro-apoptotic protein Bax from Bcl-xL. The apoptosis process is caspase-7 activation-dependent. Caryophyllene oxide is a safe anti-proliferative agent against PC-3 cells, inducing apoptosis with low toxicity towards normal cells.

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RESUMO

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)

Assuntos

RESUMO

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)

Assuntos

RESUMO

ABSTRACT: 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.

RESUMO: 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.

RESUMO

In this research, the leaves of Lepechinia heteromorpha (Briq.) Epling, Lepechinia radula (Benth.) Epling and Lepechinia paniculata (Kunth) Epling have been collected in order to perform a phytochemical study. The first species was distilled to obtain a novel essential oil (EO), while the others were submitted to ethyl acetate extraction and secondary metabolite isolation. The chemical composition of the EO from L. heteromorpha has been investigated by Gas Chromatography-Mass Spectrometry (GC-MS) and Gas Chromatography with Retention Indices (GC(RI)), identifying 25 constituents. A major compound, (-)-ledol (21.2%), and a minor compound, (-)-caryophyllene oxide (1.0%), were isolated from the EO and their structures confirmed by Nuclear Magnetic Resonance (NMR) spectroscopy. Other major constituents of the EO were viridiflorene (27.3%), (E,E)-α-farnesene (1.4%), spirolepechinene and (E)-ß-caryophyllene (7.1% each), allo-aromadendrene (6.1%), camphor (1.7%), limonene (1.3%) and ß-phellandrene (4.6%). The enantiomeric composition of the EO monoterpene fraction was also studied, determining the enantiomeric excess and distribution of α-pinene, limonene, ß-phellandrene and camphor. The ethyl acetate extract of L. radula and L. paniculata were fractionated by column chromatography. Spathulenol, angustanoic acid E and 5-hydroxy-4',7-dimethoxy flavone were isolated from L. radula extract; ledol, guaiol and (-)-carnosol were found in L. paniculata.

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BACKGROUND: Chagas Disease caused by Trypanosoma cruzi infection, is one of the most important neglected tropical diseases (NTD), without an effective therapy for the successful parasite eradication or for the blocking of the disease's progression, in its advanced stages. Due to their low toxicity, wide pharmacologic spectrum, and potential synergies, medicinal plants as Lippia alba, offer a promising reserve of bioactive molecules. The principal goal of this work is to characterize the inhibitory properties and cellular effects of the Citral and Carvone L. alba chemotype essential oils (EOs) and their main bioactive terpenes (and the synergies among them) on T. cruzi forms. METHODS: Twelve L. alba EOs, produced under diverse environmental conditions, were extracted by microwave assisted hydrodistillation, and chemically characterized using gas chromatography coupled mass spectrometry. Trypanocidal activity and cytotoxicity were determined for each oil, and their major compounds, on epimastigotes (Epi), trypomastigotes (Tryp), amastigotes (Amas), and Vero cells. Pharmacologic interactions were defined by a matrix of combinations among the most trypanocidal terpenes (limonene, carvone; citral and caryophyllene oxide). The treated cell phenotype was assessed by fluorescent and optic microscopy, flow cytometry, and DNA electrophoresis assays. RESULTS: The L. alba EOs displayed significant differences in their chemical composition and trypanocidal performance (p = 0.0001). Citral chemotype oils were more trypanocidal than Carvone EOs, with Inhibitory Concentration 50 (IC50) of 14 ± 1.5 µg/mL, 22 ± 1.4 µg/mL and 74 ± 4.4 µg/mL, on Epi, Tryp and Amas, respectively. Limonene exhibited synergistic interaction with citral, caryophyllene oxide and Benznidazole (decreasing by 17 times its IC50) and was the most effective and selective treatment. The cellular analysis suggested that these oils or their bioactive terpenes (citral, caryophyllene oxide and limonene) could be inducing T. cruzi cell death by an apoptotic-like mechanism. CONCLUSIONS: EOs extracted from L. alba Citral chemotype demonstrated significant trypanocidal activity on the three forms of T. cruzi studied, and their composition and trypanocidal performance were influenced by production parameters. Citral, caryophyllene oxide, and limonene showed a possible induction of an apoptotic-like phenotype. The best selective anti-T. cruzi activity was achieved by limonene, the effects of which were also synergic with citral, caryophyllene oxide and benznidazole.

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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%.

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This work reports the chemical study, and anti-Candida spp. activity of leaf essential oil from Mangifera indicacultivars. The essential oils were obtained by hydro-distillation and analyzed by gas chromatography/mass spectroscopy. The anti-Candida spp. activity was evaluated against strains isolated from dogs by the agar-well diffusion method and the minimum inhibitory concentration (MIC) by the broth microdilution method. Tommy Atkins cultivar presented β–selinene (29.49%), caryophyllene oxide (12.40%) and humulene II epoxide (8.66%) as main constituents, while the main constituents of Rosa, Moscatel and Jasmim varieties were caryophyllene oxide (23.62, 48.42 and 30.77%, respectively) and humulene epoxide II (11.56, 23.45, and16.27%, respectively). The means of inhibition zones were 11 ± 0.71, 13.5 ± 3.54, 10.5 ± 0.71 and 13.5 ± 0.71mm to Tommy Atkins, Rosa, Moscatel and Jasmim varieties, respectively. For Tommy Atkins, the MIC ranged from 0.62 to 1.25 mg/mL; for Rosa, ranged from 0.31 to 1.25 mg/mL; for Jasmim ranged from 0.31 to 0.62 mg/mL; while for the Moscatel variety the MIC value was 1.25 mg/mL for all Candida strains. Essential oils of four M. indica cultivars were active in vitro against Candida spp., demonstrating good antifungal activity and can be a useful source of antifungal compounds for veterinary medicine.

Este trabalho descreve a composição química e a atividade anti-Candida spp. de óleos essenciais de folhas de diversos cultivares de Mangifera indica. Os óleos essenciais foram obtidos por meio de hidrodestilação e analisados por cromatografia de gás acoplada à espectrometria de massa. A atividade anti-Candida spp. foi avaliada contra cepas isoladas de cães pelo método de difusão em ágar e a concentração inibitória mínima (CIM) pelo método de microdiluição em caldo. O cultivar Tommy Atkins apresentou β-selineno (29.49%), óxido de cariofileno (12.40%) e humuleno II epoxido (8.66%) como seus constituintes principais, enquanto que os principais componentes das variedades Rosa, Moscatel e Jasmim foram óxido de cariofileno (23,62, 48,42 e 30,77%, respectivamente) e humuleno II epoxido (11,56, 23,45 e 16,27%, respectivamente). As médias de zona de inibição foram 11 ± 0,71, 13,5 ± 3,54, 10,5 ± 0,71 e 13,5 ± 0,71mm respectivamente para os cultivares Tommy Atkins, Rosa, Moscatel e Jasmim. Para a variedade Tommy Atkins, a CIM variou de 0,62 a 1,25 mg/mL; para Rosa, 0.31 a 1.25 mg/mL; para Jasmim os valores variaram de 0,31 a 0,62 mg/mL; ao passo que para a variedade Moscatel o valor de CIM foi 1,25 mg/mL para todas as cepas de Candida spp. Os óleos essenciais das quatro variedades de M. indica foram ativos in vitro contra Candida spp., demonstrando boa atividade antifúngica, podendo ser uma fonte útil de compostos antifúngicos para uso na medicina veterinária.

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This work reports the chemical study, and anti-Candida spp. activity of leaf essential oil from Mangifera indicacultivars. The essential oils were obtained by hydro-distillation and analyzed by gas chromatography/mass spectroscopy. The anti-Candida spp. activity was evaluated against strains isolated from dogs by the agar-well diffusion method and the minimum inhibitory concentration (MIC) by the broth microdilution method. Tommy Atkins cultivar presented β–selinene (29.49%), caryophyllene oxide (12.40%) and humulene II epoxide (8.66%) as main constituents, while the main constituents of Rosa, Moscatel and Jasmim varieties were caryophyllene oxide (23.62, 48.42 and 30.77%, respectively) and humulene epoxide II (11.56, 23.45, and16.27%, respectively). The means of inhibition zones were 11 ± 0.71, 13.5 ± 3.54, 10.5 ± 0.71 and 13.5 ± 0.71mm to Tommy Atkins, Rosa, Moscatel and Jasmim varieties, respectively. For Tommy Atkins, the MIC ranged from 0.62 to 1.25 mg/mL; for Rosa, ranged from 0.31 to 1.25 mg/mL; for Jasmim ranged from 0.31 to 0.62 mg/mL; while for the Moscatel variety the MIC value was 1.25 mg/mL for all Candida strains. Essential oils of four M. indica cultivars were active in vitro against Candida spp., demonstrating good antifungal activity and can be a useful source of antifungal compounds for veterinary medicine.(AU)

Este trabalho descreve a composição química e a atividade anti-Candida spp. de óleos essenciais de folhas de diversos cultivares de Mangifera indica. Os óleos essenciais foram obtidos por meio de hidrodestilação e analisados por cromatografia de gás acoplada à espectrometria de massa. A atividade anti-Candida spp. foi avaliada contra cepas isoladas de cães pelo método de difusão em ágar e a concentração inibitória mínima (CIM) pelo método de microdiluição em caldo. O cultivar Tommy Atkins apresentou β-selineno (29.49%), óxido de cariofileno (12.40%) e humuleno II epoxido (8.66%) como seus constituintes principais, enquanto que os principais componentes das variedades Rosa, Moscatel e Jasmim foram óxido de cariofileno (23,62, 48,42 e 30,77%, respectivamente) e humuleno II epoxido (11,56, 23,45 e 16,27%, respectivamente). As médias de zona de inibição foram 11 ± 0,71, 13,5 ± 3,54, 10,5 ± 0,71 e 13,5 ± 0,71mm respectivamente para os cultivares Tommy Atkins, Rosa, Moscatel e Jasmim. Para a variedade Tommy Atkins, a CIM variou de 0,62 a 1,25 mg/mL; para Rosa, 0.31 a 1.25 mg/mL; para Jasmim os valores variaram de 0,31 a 0,62 mg/mL; ao passo que para a variedade Moscatel o valor de CIM foi 1,25 mg/mL para todas as cepas de Candida spp. Os óleos essenciais das quatro variedades de M. indica foram ativos in vitro contra Candida spp., demonstrando boa atividade antifúngica, podendo ser uma fonte útil de compostos antifúngicos para uso na medicina veterinária.(AU)

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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.

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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)

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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.

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