Effect of thyme essential oil on rumen parameters, nutrient digestibility, and nitrogen balance in wethers fed high concentrate diets / Efeito do óleo essencial de tomilho sobre os parâmetros ruminais, a digestibilidade dos nutrientes e o balanço de nitrogênio em borregos alimentados com elevado teor de concentrado

This trial aimed to evaluate the effects of thyme essential oils (EO) on rumen parameters, nutrient digestibility and nitrogen balance in wethers fed with high-concentrate diet. Twenty rumen-cannulated wethers were blocked according to body weight (BW= 64.0±2.1kg), and received one of the following treatments: 25mg of monensin/kg of dry matter (DM; MON) or doses of thyme EO (1.25, 2.50 or 3.75g/kg of DM). The diet was composed of 90% concentrate. Thyme EO was composed mainly by thymol (46.6% of DM) and p-cymene (38.9% of DM). The nutrient intake and apparent digestibility were similar among treatments. The inclusion of 3.75g of thyme EO tended (P= 0.07) to increase butyrate compared to MON and 1.25OE and wethers fed with 1.25g of thyme EO tended (P= 0.07) to decrease ruminal pH on the 14th day compared to MON. The treatments did not affect acetate:propionate ratio, total short chain fatty acids (SCFA) and nitrogen retention. Results from this study suggest that adding thyme EO to high-concentrate diets may be used as an alternative to monensin as feed additive in feedlot lambs.(AU)

O objetivo do estudo foi avaliar os efeitos do óleo essencial (OE) de tomilho nos parâmetros ruminais, na digestibilidade e no balanço de nitrogênio em borregos alimentados com elevado teor de concentrado. Vinte borregos providos de cânulas ruminais foram blocados de acordo com o peso corporal (PC=64,0±2,1kg) e receberam um dos tratamentos: 25mg de monensina/kg de matéria seca (MS; MON) ou doses de OE de tomilho (1,25; 2,50 ou 3,75g/kg de MS). A dieta foi composta por 90% de concentrado. A composição do OE de tomilho foi principalmente timol (46,6% da MS) e p-cimeno (38,9% da MS). A ingestão e a digestibilidade dos nutrientes foram semelhantes entre os tratamentos. A inclusão de 3,75g de OE de tomilho tendeu (P=0,07) a aumentar o butirato em relação aos tratamentos MON e 1,25OE. Os borregos alimentados com 1,25g de OE tenderam (P=0,07) a apresentar menor pH ruminal no 14º dia comparado a MON. No entanto, os tratamentos não afetaram a relação acetato:propionato, concentração total de ácidos graxos de cadeia curta e retenção de nitrogênio. Os resultados sugerem que a adição de OE de tomilho em dietas com elevado teor de concentrado pode ser uma alternativa à monensina como aditivo alimentar para cordeiros em confinamento.(AU)

Síntese e estudos espectroscópicos de organometálicos de rutênio-areno contendo fármacos anti-inflamatórios e derivados como ligantes / Synthesis and spectroscopic studies of ruthenium-arene organometallics bearing anti-inflammatory drugs and derivatives as ligands

Compostos organometálicos do tipo rutênio-areno têm sido estudados no transcurso dos últimos anos em razão do potencial que apresentam para o tratamento de doenças dentre as quais se destaca o câncer. Neste contexto, o presente trabalho teve como principal objetivo o estudo de organometálicos de Ru(II)-p-cimeno contendo como ligantes fármacos anti-inflamatórios não esteroides (FAINEs) ou seus derivados piridinaamida (FAINE-amida). Foram realizadas as sínteses de duas classes de compostos de fórmulas gerais [RuCl(p-cimeno)L] e [RuCl2(p-cimeno)Lam] em que L = ibuprofeno, naproxeno ou indometacina e Lam = derivado amida desses FAINES, respectivamente. A composição e estrutura dos compostos foram elucidadas principalmente com base em análise elementar, espectrometria de massas (ESI-MS), espectroscopia de ressonância magnética nuclear (1H RMN, 13C RMN, HSQC, HMBC) e espectroscopia vibracional ATR/FT-IR. Os dados indicaram que todos os fármacos-ligantes utilizados estabilizam a unidade Ru(II)-areno, sendo que os carboxilatos coordenam-se ao Ru(II) de modo bidentado por ambos os átomos de oxigênio, enquanto que a coordenação dos derivados amida ocorre pelo nitrogênio do anel piridínico. No entanto, em contraste ao comportamento em solventes não-coordenantes como clorofórmio, estudos em solução indicaram que a presença de dimetilsulfóxido promove dissociação do fármaco ligante acompanhada pela coordenação do solvente (gradual, no caso de L, ou imediata total no caso de Lam). Resultados preliminares de estudos de espectroscopia de fluorescência sugerem interação dos compostos de Ru(II)-areno-indometacina com albumina de soro humano (HSA)

Ruthenium-arene organometallics have been investigated in recent years due to the potential for treatment of diseases among which cancer is highlighted. In this context, the main objective of the present work is the study of organometallics of Ru(II)-p-cymene bearing non steroidal anti-inflammatory drugs (NSAIDs) or their pyridine-amide (NSAIDamide) as ligands. Two classes of compounds of general formula [RuCl(p-cymene)L] and [RuCl2(p-cymene)Lam], in which L = ibuprofen, naproxen or indomethacin and Lam = amide derivative of these NSAIDs, respectively have been synthesized. The composition and the structure of these compounds have been elucidated mainly based on elemental analysis, mass spectrometry (ESI-MS), nuclear magnetic resonance spectroscopy (1H RMN, 13C RMN, HSQC, HMBC) and vibrational spectroscopy (ATR/FT-IR). The data indicate that all the used drug-ligands stabilize the Ru(II)-arene framework, being that the carboxylates coordinate Ru(II) in bidentate mode through both oxygen atoms while the coordination of the amide derivatives occurs via nitrogen atom of the pyridine ring. However, in contrast to the behavior in non-coordinating solvents such as chloroform, studies in solution indicate that the presence of dimethylsulfoxide promotes dissociation of the drug ligand accompanied by the coordination of the solvent (gradual, for L, or total immediate for Lam). Preliminary results from fluorescence spectroscopy suggest interaction of the Ru(II)-arene-indomethacin compounds with human serum albumin (HSA)

Antioxidant activity and total phenolic and flavonoid content of the extract and chemical composition of the essential oil of Eremostachys laciniata collected from Zagros

Objective To examine the chemical component of the essential oil of Eremostachys laciniata and evaluate antioxidant activity of the extract. Methods The hydrodistillated essential oil was analyzed by gas chromatography-flame ionization detector and gas chromatography–mass spectrometry. Also, antioxidant activity, total phenolic and flavonoid content were determined by 2,2-diphenyl-1-picrylhydrazyl, Folin-Ciocalteu and colorimetric method, respectively. Results The major components of the essential oil were p-cymene (21.64%), linalool (17.93%), and α-pinene (11.42%). Also, the extract obtained by methanol showed a good antioxidant activity. The same extract also exhibited high phenolic and flavonoid contents. Conclusions These results indicate that Eremostachys laciniata can be used in dietary applications with a potential to reduce oxidative stress.

Antioxidant activity and total phenolic and flavonoid content of the extract and chemical composition of the essential oil of Eremostachys laciniata collected from Zagros

Objective: To examine the chemical component of the essential oil of Eremostachys laciniata and evaluate antioxidant activity of the extract. Methods: The hydrodistillated essential oil was analyzed by gas chromatography-flame ionization detector and gas chromatography–mass spectrometry. Also, antioxidant ac-tivity, total phenolic and flavonoid content were determined by 2,2-diphenyl-1-picrylhydrazyl, Folin-Ciocalteu and colorimetric method, respectively. Results: The major components of the essential oil were p-cymene (21.64%), linalool (17.93%), and a-pinene (11.42%). Also, the extract obtained by methanol showed a good antioxidant activity. The same extract also exhibited high phenolic and flavonoid contents. Conclusions: These results indicate that Eremostachys laciniata can be used in dietary applications with a potential to reduce oxidative stress.

Effects of Lippia sidoides essential oil, thymol, p-cymene, myrcene and caryophyllene on rat sciatic nerve excitability

Lippia sidoides Cham is a typical herb species of Northeast Brazil with widespread use in folk medicine. The major constituents of the essential oil of L. sidoides (EOLs) are thymol, p-cymene, myrcene, and caryophyllene. Several studies have shown that the EOLs and its constituents have pharmacological effects, including antibacterial, anti-inflammatory, antioxidant and neuroprotective activity. Therefore, this work aimed to investigate the effects of the EOLs and their main constituents on rat sciatic nerve excitability. The sciatic nerves of adult Wistar rats were dissected and mounted in a moist chamber. Nerves were stimulated by square wave pulses, with an amplitude of 40 V, duration of 100 μs to 0.2 Hz. Both EOLs and thymol inhibited compound action potential (CAP) in a concentration-dependent manner. Half maximal inhibitory concentration for CAP peak-to-peak amplitude blockade were 67.85 and 40 µg/mL for EOLs and thymol, respectively. CAP peak-to-peak amplitude was significantly reduced by concentrations ≥60 µg/mL for EOLs and ≥30 µg/mL for thymol. EOLs and thymol in the concentration of 60 µg/mL significantly increased chronaxie and rheobase. The conduction velocities of 1st and 2nd CAP components were also concentration-dependently reduced by EOLs and thymol in the range of 30-100 µg/mL. Differently from EOLs and thymol, p-cymene, myrcene and caryophyllene did not reduce CAP in the higher concentrations of 10 mM. These data demonstrated that EOLs and thymol inhibited neuronal excitability and were promising agents for the development of new drugs for therapeutic use.

Characterization and evaluation of the cytotoxic potential of the essential oil of Chenopodium ambrosioides

Abstract The essential oil of Chenopodium ambrosioides L., Amaranthaceae, was obtained by steam distillation in a Clevenger apparatus and characterization was performed using chromatographic and spectroscopic assays (GC-FID, GC/MS, 1H NMR). Two major compounds were identified: p-cymene (42.32%) and ascaridole (49.77%). The ethanolic extract and hydrolate were fractionated by liquid–liquid partitioning and the compounds were characterized by GC/MS. The essential oil, ethanol extract and fractions by partitioning with dicloromethane, ethyl acetate and butanol were tested in tumor cell lines (K562, NALM6, B15, and RAJI). Significant cytotoxic activity was found for essential oil (IC50 = 1.0 µg/ml) for RAJI cells and fraction dicloromethane (IC50 = 34.0 µg/ml) and ethanol extract (IC50 = 47.0 µg/ml) for K562 cells. The activity of the essential oil of C. ambrosioides is probably related to the large amount of ascaridol, since the other major compound, p-cymene, is recognized as a potent anti-inflammatory and has low cytotoxic activity.

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

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

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

Um possível mecanismo de ação para o efeito anticonvulsivante do p-cimeno / A plausible mechanism of action for the anticonvulsant effect of p-cymene

O presente estudo teve como objetivo investigar o efeito anticonvulsivante do p-cimeno (CIM), bem como verificar a concentração das monoaminas (dopamina(DA), noradrenalina (NA), serotonina (5-HT), e seus metabólitos (ácido dihidroxifenilacético (DOPAC), ácidohomovanílico (HVA) e ácido 5-hidroxi-indol-acético (5-HIAA)) no hipocampo de camundongos tratados com cloridrato de pilocarpina 400 mg/kg (P400; i.p.) e nos grupos tratados com a associação de CIM (50, 100 ou150 mg/kg) e P400. Nesse estudo foi avaliada a latência para a primeira crise epiléptica e a taxa de mortalidade. Os resultados revelaram que o CIM produziu um aumento na latência para primeira crise epilética, bem como promoveu uma proteção significativa contra a mortalidade induzida pelo processo convulsivo. O monoterpeno nas doses testadas também foi capaz de produzir um aumento da latência para instalação do estado de mal epilético induzido por pilocarpina. Além disso, durante os estudos para identificar o mecanismo de ação nenhum dos efeitos do p-cimeno nesse modelo foram bloqueados pelo pré-tratamento com atropina. Complementando os estudos para identificar o provável mecanismo de ação do p-cimeno, foi verificado que os efeitos desse monorterpeno foram revertidos pelo flumazenil, um antagonista do sistema GABAérgico, sugerindo que esse monoterpeno pode atuar por meio desse sistema. Também, em nossos resultados também foi visto uma diminuição dos níveis de DA e um aumento do conteúdo de seus metabólitos (DOPAC e HVA) durante as crises epilépticas. Por outro lado foi detectado um aumento na concentração de NA e 5-HT, e uma diminuição no metabólito da 5-HT (5-HIAA) durante as crises epilépticas. Dessa forma, o CIM na presença do estímulo convulsivo, reverte os efeitos produzidos nos níveis das monoaminas e seus metabólitos observados durante as crises epilépticas, sugerindo que este monoterpeno produz efeito anticonvulsivante por meio da modulação direta do sistema GABAérgico e indiretamente por...

The aim of this study was to investigate the anticonvulsant effect of p-cymene (CYM) and to determine the concentrations of monoamines (dopamine (DA), noradrenaline (NA) and serotonin (5-HT)), and their metabolites (dihydroxyphenylacetic acid (DOPAC), homovanillic acid (HVA) and 5-hydroxyindoleacetic acid (5-HIAA)) in the hippocampus of mice treated with pilocarpine hydrochloride 400 mg/kg (P400; i.p.) and in groups treated with a combination of CYM (50,100 or 150 mg/kg) and P400. We assessed the latency to the first epileptic seizure and the mortality rate. Results showed that CYM produced an increase in latency to the first seizure, as well as providing significant protection against mortality induced by seizures. Higher doses of the monoterpene were also able to prolong the latency to the onset of status epilepticus induced by pilocarpine. Moreover, in an experiment to throw light on the mechanism of action of p-cymene, none of its effects was blocked by pretreatment with atropine. In further studies to identify the probable mechanism of CYM, it was observed that the effectsof this monoterpene were reversed by flumazenil, anantagonist of the GABAergic system, suggesting that it may act through this cerebral system. Furthermore, our results also showed a fall in DA levels and an increase in the contents of its metabolites (DOPAC and HVA) during seizures. On the other hand, increases in NA and 5-HT concentrations and a decrease in that of the 5-HTmetabolite (5-HIAA) were detected during seizures. Thus, CYM, in the presence of a convulsant stimulus, reverses the effects on levels of monoamines and their metabolites observed during seizure activity, suggesting that this monoterpene produces its anticonvulsant effect by modulating the GABAergic system directly and/or indirectly, through changes in monoamine (DA, NA and 5-HT) contents opposite to those observed during the convulsive process in the hippocampal region. However,further studies are necessary to...

Leishmanicidal activity of carvacrol-rich essential oil from Lippia sidoides Cham

Leishamaniasis is a disease that affects more than 2 million people worldwide, whose causative agent is Leishmania spp. The current therapy for leishmaniasis is far from satisfactory. All available drugs, including pentavalent antimony, require parenteral administration and are potentially toxic. Moreover, an increase in clinical resistance to these drugs has been reported. In this scenario, plant essential oils used traditionally in folk medicine are emerging as alternative sources for chemotherapeutic compounds. In this study, in vitro leishmanicidal effects of a thymol- and a carvacrol-rich essential oil from leaves of Lippia sidoides Cham. were investigated. The essential oils were extracted and their constituents were characterized by gas chromatography coupled to mass spectrometry (GC/MS). Both essential oils showed significant activity against promastigote forms of Leishmania chagasi. However, we found that carvacrol-rich essential oil was more effective, with IC50/72 h of 54.8 μg/mL compared to 74.1 μg/mL for thymol-rich oil. Carvacrol also showed lower IC50 than thymol. Our data suggest that L. sidoides essential oils are indeed promising sources of leishmanicidal compounds.

p-Cymene reduces orofacial nociceptive response in mice

This study investigated the possible antinociceptive effect of p-cymene in different tests of orofacial nociception. The animals (mice) were pretreated (i.p.) with p-cymene (25, 50, 100 mg/kg), morphine (5 mg/kg), or vehicle (0.2 percent Tween 80+saline), and were then subsequently administered, subcutaneously into their upper lip: formalin, capsaicin, and glutamate. The nociceptive behavior response was characterized by the time in s that the mice remained rubbing the orofacial region, for a period of 40 min in the formalin test (first phase, 0-6 min; and second phase, 21-40 min), and for 42 and 15 min in the capsaicin and glutamate tests, respectively. To verify the possible opioid involvement in the antinociceptive effects, naloxone (i.p.) was administered into the mice 15 min prior to the pretreatment with p-cymene (100 mg/kg). Finally, whether or not the p-cymene evoked any change in motor performance in the Rota-rod test was evaluated. The results showed that the treatment with p-cymene, at all doses, reduced (p<0.001) the nociceptive behavior in all nociception tests. The antinociceptive effect of p-cymene was antagonized by naloxone (1.5 mg/kg). Additionally, mice treated with p-cymene did not show any change in motor performance. In conclusion, p-cymene attenuated orofacial nociception, suggesting an involvement of the opioid system in this effect. Thus, p-cymene might represent an important biomolecule for management and/or treatment of orofacial pain.

O oleo essencial de Lippia gracilis Schauer, Verbenaceae, em ratos diabeticos / The essential oil from Lippia gracilis Schauer, Verbenaceae, in diabetic rats

O óleo essencial das folhas de Lippia gracilis Schauer, Verbenaceae, foi examinado por CG e CG-MS. Quinze constituintes foram identificados, onde o carvacrol, p-cimeno e o γ-terpineno foram as substâncias majoritárias. No estudo in vitro, a solução a 5 por cento do óleo de L. gracilis Schauer apresentou atividade antibacteriana para Staphylococcus aureus isolado de úlcera infectada de paciente diabético. O estudo avaliou a atividade antibacteriana da solução a 5 por cento do óleo de L. gracilis Schauer em modelo experimental em diabetes utilizando ratos albinos Wistar machos com membro pélvico infectado com cepa de Staphylococcus aureus. No experimento foram utilizados 28 ratos Wistar distribuídos em quatro grupos (G1-branco, G2-controle negativo, G3-controle positivo, G4-teste) de sete ratos. Quando comparado o grupo G4 com G3, observou-se que a solução a 5 por cento promoveu uma redução nas CFU/mL após 24h da administração do inóculo (S.aureus sem L. gracilis Schauer 10(8) ± 313 versus S.aureus com L. gracilis Schauer 13,28 ± 4,03). Os resultados foram expressos através do cálculo da média±EPM) e análise de variança (ANOVA). A diferença entre a concentração inibitória mínima no estudo in vitro foi determinada pelo teste Turkey (p<0.05). O teste Newman-Keuls com nível de significância (p<0.05) foi utilizado para o cálculo dos resultados obtidos no experimento in vivo. A solução a 5 por cento do óleo essencial de Lippia gracilis Schauer apresentou boa atividade antibacteriana tanto no estudo in vivo como no in vitro.

The essential oil from Lippia gracilis Schauer (Verbenaceae) leaves was examined by GC and GC-MS. Fifteen constituents were identified. Carvacrol, p-cymene and γ-terpinene were found to be the major components. In the in vitro study, 5 percent solution of the Lippia gracilis Schauer oil presented antibacterial activity against Staphylococcus aureus isolated from diabetic patients with infected ulcers. The study evaluated the antibacterial activity of the 5 percent solution of the Lippia gracilis Schauer oil on the experimental model of diabetic adult male albino Wistar rats with leaft pelvic limb infected by Staphylococcus aureus strain. In this experiment, 28 diabetic Wistar rats were used, randomly distributed in four different groups of seven rats, (G1-white; G2-negative control; G3-positive control and G4-test). When comparing group G4 with G3, it was observed that the 5 percent solution presented a reduced CFU/mL level showing the antibacterial effect of the oil 24 hours after the administration of the inoculum (S .aureus without Lippia gracilis Schauer 108 ±313 versus S.aureus with Lippia gracilis Schauer 13.28±4.03). The results were expressed as mean±S.E.M. One-way analysis of the variance (ANOVA) was used. The differences between the minimum inhibitory concentration in vitro test were determined by the Tukey test (p<0.05). The Newman-Keuls test with level of significance (p<0.05) was used to measure the results in vivo. The findings have shown that 5 percent solution of the Lippia gracilis Schauer oil presented antibacterial activity in vitro and in vivo.

Chemical composition of the essential oils from two subspecies of Protium heptaphyllum / Composição química do óleo essencial de duas subespécies do Protium heptaphyllum

Qualitative and quantitative analyses of the volatile constituents from resin of Protium heptaphyllum (Aubl.) Marchand subsp. ulei (Swat) Daly (PHU), and Protium heptaphyllum (Aubl.) Marchand subsp. heptaphyllum (PHH), Burseraceae were performed using GC-MS and GC-FID. The resins were collected around the city of Cruzeiro do Sul, state of Acre, Brazil. Essential oils from the two subspecies were extracted by hydrodistillation with a yield of 8.6 percent (PHU) and 11.3 percent (PHH); the main components were terpinolene (42.31 percent) and p-cymene (39.93 percent) for subspecies ulei (PHU) and heptaphyllum (PHH), respectively.

As análises qualitativa e quantitativa dos óleos essenciais obtidos das resinas das espécies Protium heptaphyllum (Aubl.) Marchand subespécie ulei (Swat) Daly (PHU) e Protium heptaphyllum (Aubl.) Marchand subespécie heptaphyllum (PHH), Burseraceae, foram realizadas utilizando cromatografia em fase gasosa acoplado a um espectrômetro de massa (CG-EM) e cromatografia a gás com detector de chama (CG-DIC). As resinas foram coletadas no Município de Cruzeiro do Sul, Acre, Brasil. O óleo essencial das oleoresinas foi extraído por hidrodestilação fornecendo rendimento 8,6 por cento para PHU e 11,3 por cento para PHH. Os monoterpenos terpinoleno (42.31 por cento) e p-cimeno (39.93 por cento) foram os constituintes principais para PHU e PHH, respectivamente.

Cutaneous Toxicity of Compound P-Cymene Cream on Rabbits / 中国药房

OBJECTIVE: To study the cutaneous toxicity of Compound p-cymene cream.METHODS: Different dosage of Compound p-cymene cream was applied on normal skin and the damaged skin of hairless area of rabbits,and the presence of acute toxicity.RESULTS: Compound p-cymene cream induced neither acute toxicity nor cutaneous irritant reaction.CONCLUSION: Compound p-cymene cream is a safe locally applied external preparation.