Chemical composition of essential oils from the apiaceae family, cytotoxicity, and their antifungal activity in vitro against candida species from oral cavity / Composição química de óleos essenciais da família apiaceae, citotoxicidade e sua atividade antifúngica in vitro contra espécies de candida da cavidade oral

Abstract The aims of this research were: evaluate the chemical composition and the cytotoxicity of the Cuminum cyminum (cumin), Anethum graveolens (dill), Pimpinella anisum (anise) and Foeniculum vulgare (fennel) essential oils, as well as their antifungal activity in vitro against ten Candida spp. isolates. The chemical composition of the oils was analyzed by means of gas chromatography coupled with mass spectrometry (GC/MS). The cytotoxicity assays were performed, using the cell proliferation reagent WST-1 in L929 mouse fibroblasts (20x103 well-1). The determinate the Minimum Inhibitory Concentration (MIC), was performed through the Broth Microdilution technique (CLSI). The chemical main components were the cuminaldehyde (32.66%) for cumin, carvone (34.89%) for the dill, trans-anethole (94.01%) for the anise and anethole (79.62%) for the fennel. Anise and fennel did not were cytotoxic in all the tested concentrations, however the cumin oil was cytotoxic in the concentration of 20 mg.mL-1 and the dill in the concentrations of 20 and 8 mg.mL-1. All yeasts were susceptible against the evaluated essential oils. Cumin presented the lowest MIC against yeasts. We concluded that all the essential oils presented inhibitory action against Candida spp., and C . cyminum, P. anisum and F. vulgare were not cytotoxic in the same minimum inhibitory concentrations for the fungi.

Resumo Os objetivos desta pesquisa foram: avaliar a composição química e a citotoxicidade dos óleos essenciais de Cuminum cyminum (cominho), Anethum graveolens (endro), Pimpinella anisum (erva-doce) e Foeniculum vulgare (funcho), bem como sua atividade antifúngica in vitro contra dez isolados de Candida spp.. A composição química dos óleos foi analisada por meio de cromatografia gasosa acoplada à espectrometria de massa (GC / MS). Os ensaios de citotoxicidade foram realizados, utilizando o reagente de proliferação celular WST-1 em fibroblastos de ratinho L929 (20x103 poço-1). A determinação da Concentração Inibitória Mínima (MIC) foi realizada através da técnica de microdiluição em caldo (CLSI). Os principais componentes químicos foram o cuminaldeído (32.66%) para cominho, carvona (34.89%) para o endro, trans-anetol (94.01%) para erva-doce e anetol (79.62%) para a funcho. O endro e a erva-doce não foram citotóxicos em todas as concentrações testadas, no entanto, o óleo de cominho foi citotóxico na concentração de 20 mg.mL-1 e o endro nas concentrações de 20 e 8 mg.mL-1. Todas as leveduras foram suscetíveis aos óleos essenciais avaliados. O cominho apresentou a menor CIM contra as leveduras. Concluímos que todos os óleos essenciais apresentaram ação inibidora contra Candida spp., e C. cyminum, P. anisum e F. vulgare não foram citotóxicos nas mesmas concentrações inibitórias mínimas para os fungos.

The anticonvulsant effects of Ducrosia anethifolia (Boiss) essential oil are produced by its main component alpha-pinene in rats / Os efeitos anticonvulsivantes do óleo essencial de Ducrosia anethifolia (Boiss) são realizados pelo seu principal componente alfa-pineno em ratos

ABSTRACT Ducrosia anethifolia has been recommended as a remedy for neurological disorders. However, the anticonvulsant effects of D. anethifolia essential oil (DAEO) and its major constituent α-pinene have not yet been clarified. Methods: A rat model of pentylenetetrazole (PTZ)-induced convulsions was used. Oxidant and antioxidant parameters were assayed in the temporal lobe. Results: The data showed that DAEO (50, 100 and 200 mg/kg, i.p.) and α-pinene (0.2 and 0.4 mg/kg i.p.) delayed the initiation time, and reduced the duration of myoclonic and tonic-clonic seizures following PTZ injection. The PTZ produced oxidative stress so that malondialdehyde and hydrogen peroxide levels were increased and catalase and peroxidase activity decreased. Pretreatment with DAEO and α-pinene significantly inhibited the above-mentioned enzymatic changes in PTZ-treated animals. Conclusion: The results suggest that α-pinene, at teast in part, was responsible for the induction of the anticonvulsant and antioxidant effects of DAEO in rats.

RESUMO A Ducrosia anethifolia tem sido recomendada como remédio para os distúrbios neurológicos. No entanto, os efeitos anticonvulsivantes do óleo essencial de Ducrosia anethifolia (DAEO) e do seu principal constituinte atfa-pineno (α-pineno) ainda não foram clarificados. Métodos: Foi utilizado um modelo de rato de convulsões induzidas por pentilenotetrazol (PTZ). Os parâmetros oxidante e antioxidante foram ensaiados no lobo temporal do cérebro. Resultados: Os dados mostraram que DAEO (50, 100 e 200 mg / kg, i.p.) e α-pineno (0,2 e 0,4 mg / kg i.p.) retardaram o tempo de iniciação e reduziram a duração das crises mioclônicas e tônico-clônicas após a injeção de PTZ. O PTZ produziu estresse oxidativo, de modo que os níveis de malondialdeído (MDA) e de peróxido de hidrogênio aumentaram e a atividade da catalase e da peroxidase diminuiu. O pré-tratamento com DAEO e α-pineno inibiu significativamente as alterações enzimáticas mencionadas em animais tratados com PTZ. Conclusão: O resultado sugere que α-pineno, peto menos em parte, é responsável peta indução dos efeitos anticonvulsivantes e antioxidantes da DAEO em ratos.

Morphological alterations and time-kill studies of the essential oil from the leaves of Coriandrum sativum L. on Candida albicans / Alteraciones morfológicas y estudios de letalidad del aceite esencial de las hojas de Coriandrum sativum L. en Candida albicans

The objective of this study was to evaluate the morphological alterations and time-kill of the essential oil of the leaves of C. sativum L. on strains of C. albicans. The essential oil was submitted to gas chromatography-mass spectrometry analysis. The predominant component identified was linalool (39.78 percent). Minimal inhibitory concentration and minimal fungicidal concentration of the essential oil were respectively 512 and 1024 ug.mL-1 for 90 percent of the strains tested. In the time-kill curves, the essential oil showed a concentration-dependent fungicidal effect. In the micromorphology assay it caused a significant reduction in pseudohyphae, an important pathogenic factor of C. albicans.

El objetivo de este estudio fue evaluar las alteraciones morfológicas y de letalidad del aceite esencial de las hojas de C. sativum L. en cepas de C. albicans. El aceite esencial se presentó a gas análisis de espectrometría de cromatografía-masa. El componente predominante identificado fue linalol (39,78 por ciento). Concentración inhibitoria mínima y concentración mínima fungicida del aceite esencial fueron, respectivamente, 512 y 1.024 ìg.mL-1 para 90 por ciento de las cepas probadas. En las curvas el tiempo-matar, el aceite esencial mostró un efecto fungicida dependiente de la concentración. En el ensayo de micromorfología causó una reducción significativa en pseudohifas, un importante factor patógeno de C. albicans.

Morphological characterization of pollens from three Apiaceae species and their ingestion by twelve-spotted lady beetle (Coleoptera: Coccinellidae) / Caracterização morfológica de três espécies de Apiaceae e sua ingestão pela joaninha de doze pintas (Coleoptera: Coccinellidae)

Abstract Larvae and adults of certain species of predator lady beetles feed on pollen, guaranteeing their survival, and at times, reproduction in the absence of preferred prey. Palynology, therefore, may contribute in the investigation of botanical families visited by these predators in order to obtain this floral resource. There are records of the visitation of Apiaceae flowers by Coleomegilla maculata DeGeer, 1775 (Coleoptera, Coccinellidae), but not the ingestion of their pollen grains by this lady beetle. The external morphology of pollen grains of three Apiaceae aromatic species (Anethum graveolens L., Coriandrum sativum L., Foeniculum vulgare Mill.) was characterized, and it was evaluated the ingestion of these pollens by fourth instar larvae and adults of C. maculata upon confinement along with flowers of these Apiaceae for 24 and 48 hours. The pollen grains of those species presented similar external morphology. In the two times of exposure, the larvae ingested the same amount of pollen from the three Apiaceae species, and the amount of C. sativum pollen ingested was the same between larvae and adults. The amount of A. graveolens pollen grains ingested by the adults was significantly greater than the pollens of C. sativum and F. vulgare, in 24 hours, with the opposite occurring in 48 hours. In the first 24 hours, the adults ingested more A. graveolens pollen than the larvae, with the opposite occurring with F. vulgare. There was no significant difference in the amount of Apiaceae pollen ingested between larvae and adults in 48 hours. The results suggest that the pollen-eating habits of certain aphidophagous lady beetles may be crucial in their preservation within agro-ecosystems.

Resumo Larvas e adultos de certas espécies de joaninhas predadoras podem se alimentar de pólen, garantindo a sua sobrevivência, e, às vezes, a reprodução na ausência da presa preferencial. Palinologia, portanto, pode contribuir na investigação de famílias botânicas visitadas por estes predadores a fim de obter esse recurso floral. Há registros da visitação de flores de Apiaceae por Coleomegilla maculata DeGeer, 1775 (Coleoptera, Coccinellidae), mas não da ingestão de seus grãos de pólen por essa joaninha. A morfologia externa de grãos de pólen de três espécies aromáticas de Apiaceae (Anethum graveolens L., Coriandrum sativum L., Foeniculum vulgare Mill.) foi caracterizada e avaliou-se a ingestão desses polens por larvas de quarto instar e adultos de C. maculata em confinamento com flores dessas Apiaceae por 24 e 48 horas. Os grãos de pólen dessas espécies apresentaram morfologia externa semelhante. Nos dois tempos de exposição, as larvas ingeriram a mesma quantidade de pólen das três espécies de Apiaceae, e a quantidade de pólen de C. sativum ingerida foi semelhante entre as larvas e adultos. A quantidade de grãos de pólen de A. graveolens ingerida pelos adultos foi significativamente maior do que a dos polens de C. sativum e F. vulgare, em 24 horas, com o oposto ocorrendo em 48 horas. Nas primeiras 24 horas, os adultos ingeriram mais pólen de A. graveolens do que as larvas, ocorrendo o oposto com F. vulgare. Não houve diferença significativa na quantidade de pólen de Apiaceae ingerida entre as larvas e adultos em 48 horas. Os resultados sugerem que o hábito de alimentar de pólen de certas joaninhas afidófagas pode ser crucial para a sua preservação dentro dos agroecossistemas.

Monoterpene isolated from the essential oil of Trachyspermum ammi is cytotoxic to multidrug-resistant Pseudomonas aeruginosa and Staphylococcus aureus strains

Abstract INTRODUCTION: The aim of this study was to determine whether an herbal extract containing monoterpene exhibited activity against multidrug-resistant Staphylococcus aureus and Pseudomonas aeruginosa isolated from clinical infection samples. METHODS: The essential oil of Trachyspermum ammi (L.) Sprague ex Turrill (Apiaceae) fruit was extracted by hydrodistillation. Fruit residues were treated with hydrochloric acid and re-hydrodistilled to obtain volatile compounds. Compounds in the distilled oil were identified using gas-chromatography (GC) and GC-mass spectrometry (MS). The antibiotic susceptibility of all bacterial isolates was analyzed using both the disc diffusion method and determination of the minimum inhibitory concentration (MIC). The sensitivity of antibiotic-resistant isolates to essential oil was also determined by using the disc diffusion method and MIC determination. RESULTS: Of 26 clinical isolates, 92% were multidrug-resistant (MDR). Aromatic monoterpenes (thymol, paracymene, and gamma-terpinene) were the major (90%) components of the oil. Growth of S. aureus strains was successfully inhibited by the oil, with an inhibitory zone diameter (IZD) between 30-60mm and MIC <0.02μL/mL. The oil had no antimicrobial activity against clinical isolates of P. aeruginosa; rather, it prevented pigment production in these isolates. CONCLUSIONS: This study revealed that the essential oil of Trachyspermum ammi, which contains monoterpene, has good antibacterial potency. Monoterpenes could thus be incorporated into antimicrobial ointment formulas in order to treat highly drug-resistant S. aureus infections. Our findings also underscore the utility of research on natural products in order to combat bacterial multidrug resistance.

Protective potential of trachyspermum ammi seeds in gentamicin-induced nephrotoxicity in rabbit model / Potencial de protección de las semillas trachyspermum ammi en la nefrotoxicidad inducida por la gentamicina en modelo de conejo

Nephrotoxicity is one of the most important side effects and therapeutic limitations of aminoglycoside antibiotics, especially gentamicin. Gentamicin-induced nephrotoxicity involves free radical generation, reduction in antioxidant defense mechanism and renal dysfunction. A number of crude herbal extracts have potential to ameliorate gentamicin-induced nephrotoxicity due to presence of various antioxidant compounds. Therefore the goal of current study was to evaluate the protective activity of T. ammi seeds aqueous extract against gentamicin-induced nephrotoxicity in albino rabbits. The results showed that gentamicin caused severe alterations in serum biochemical parameters and kidney markers along with severe alterations in kidney tissues. However, T. ammi extract, when given along with gentamicin, reversed the severity of gentamicin-induced nephrotoxicity by normalizing the indicators of kidney function e.g. serum urea, creatinine, blood urea nitrogen, albumin and serum electrolyte parameters indicating the nephroprotective potential of T. ammi. Similarly the extract has ability to augment the endogenous antioxidant enzymatic machinery by increasing the activity of antioxidant enzyme catalase and by reducing the total oxidant status. Nephroprotective potential was further confirmed by the histopathological examination. Nephroprotective potential might be due to the presence of antioxidative polyphenolic compounds in aqueous extract of T. ammi seeds.

La nefrotoxicidad es uno de los efectos secundarios más importantes limitaciones terapéuticas de los antibióticos aminoglucósidos, especialmente gentamicina. La nefrotoxicidad inducida por gentamicina implica generación de radicales libres, la reducción en el mecanismo de defensa antioxidante y la disfunción renal. Una serie de extractos de hierbas crudas tienen potencial para mejorar la nefrotoxicidad inducida por gentamicina debido a la presencia de varios compuestos antioxidantes. Por lo tanto, el objetivo del presente estudio fue evaluar la actividad protectora del extracto acuoso semillas de T. ammi contra la nefrotoxicidad inducida por gentamicina en conejos albinos. Los resultados mostraron que la gentamicina causó graves alteraciones en los parámetros bioquímicos séricos y los marcadores de riñón, junto con alteraciones severas en los tejidos renales. Sin embargo, el extracto de T. ammi, cuando se administra junto con la gentamicina, invierte la gravedad de la nefrotoxicidad inducida por gentamicina por la normalización de los indicadores de la función renal, por ejemplo, urea sérica, creatinina, nitrógeno ureico en sangre, albúmina y los parámetros de electrolitos séricos que indican el potencial nefroprotector de T. ammi. Del mismo modo, el extracto tiene la capacidad para aumentar la maquinaria enzimática antioxidante endógena mediante un aumento de la actividad de la enzima antioxidante catalasa y reduciendo el estado total de oxidante. El potencial nefroprotector fue confirmado por el examen histopatológico. El potencial nefroprotector podría ser debido a la presencia de compuestos polifenólicos antioxidantes en el extracto acuoso de semillas de T. Ammi.

Determination of antibacterial, antioxidant, antiplatelet and inhibition of cholinesterase activities from the methanolic extracts of Azorella species (Apiaceae) / Determinación de la actividad antibacteriana, antioxidante, antiagregante plaquetaria e inhibición de la colinesterasa a partir de los extractos metanólicos de especies Azorella (Apiaceae)

In this study, we investigated the potential antibacterial, antioxidant and anti-platelet activities and the inhibition of cholinesterase from the methanolic extracts obtained from aerial parts of the two species of Azorella: A. spinosa (Constitution, Chile) and A. monantha (Torres del Paine, Enladrillado and Paso Vergara). All extracts showed only moderate inhibitory activity on acetylcholinesterase (AChE), the most active extract with IC50 = 27ug/mL was A. spinosa. Inhibition of platelet aggregation induced by ADP presented maximal aggregation to 70 and 57 percent on extracts of A. spinosa and A. monantha (Paso Vergara), respectively. The most active extract with antioxidant effect was A. spinosa with IC50 of 28.72ug/mL. Antibacterial activity of the extract on Escherichia coli, Pseudomonas aeruginosa and Acinetobacter baumannii was not present. The extracts of A. spinosa and A. monantha (Paso Vergara) presented the best results on the activities that were evaluated.

En este estudio se investigó las potenciales actividades antibacteriana, antioxidante, antiplaquetaria e inhibición de la colinesterasa de extractos metanólicos a partir de las partes aéreas de dos especies de Azorella: A. spinosa (Constitución, Chile) y A. monantha (Torres del Paine, Enladrillado y Paso Vergara). Todos los extractos mostraron actividad inhibidora moderada solamente sobre acetilcolinesterasa (AChE), siendo el más activo el extracto de A. spinosa con IC50= 27ug/mL. La inhibición de la agregación plaquetaria inducida por ADP presentó máxima agregación al 70 y 57 por ciento sobre los extractos de A. spinosa y A. monantha (Paso Vergara) respectivamente. El extracto más activo con efecto antioxidante fue el de A. spinosa con un IC50 de 28,72ug/mL,). No se presentó actividad antibacteriana de ningún extracto sobre Escherichia coli, Pseudomonas aeuroginosa y Acinetobacter baumannii. Los extractos de A. spinosa y A. monantha (Paso Vergara) presentan los mejores resultados sobre las actividades evaluadas, lo que permite el estudio bioguiado de los metabolitos presentes en estos extractos.

GC/MS analysis of high-performance liquid chromatography fractions from Sophora flavescens and Torilis japonica extracts and their in vitro anti-neosporal effects on Neospora caninum

We analyzed alcoholic extracts of herbs possessing anti-neosporal activity against Neospora (N.) caninum. To identify the chemical components of Sophora (S.) flavescens and Torilis (T.) japonica associated with anti-neosporal activity, specific fractions were isolated by high-performance liquid chromatography (HPLC). In vitro activity of the fractions against N. caninum was then assessed. Gas chromatography/mass spectrometry (GC/MS) was used to identify and quantify specific anti-neosporal molecules in the herbal extracts. Almost all HPLC fractions of S. flavescens and T. japonica had higher levels of anti-neosporal activity compared to the not treated control. Active constituents of the extracts were sophoridane, furosardonin A, and tetraisopropylidene-cyclobutane in S. flavescens; 5,17-beta-dihydroxy-de-A-estra-5,7,9,14-tetraene, furanodiene, and 9,12-octadecadienoic acid (Z,Z)-(CAS,1) in T. japonica.

Chemical composition of the essential oil from kelussia odoratissima mozaff. and the evaluation of its sedative and anxiolytic effects in mice

OBJECTIVE: The present study aimed to evaluate the sedative and anxiolytic effects of the essential oils and hydroalcoholic extract of Kelussia odoratissima Mozaff. (K. odoratissima) in mice by utilizing an elevated plus maze. The chemical composition of its essential oil was also determined. METHODS: The hydroalcoholic extract or essential oil fraction from this plant were administered intraperitoneally to male mice at various doses 30 min before testing. The anxiolytic and sedative effects were determined by an elevated plus maze and locomotor activity tests, respectively. RESULTS: According to the results, none of the administered doses of hydroalcoholic extract or essential oil fraction of K. odoratissima changed the percentage of the time spent or number of entries into the open arms of the elevated plus maze. In contrast, the cumulative spontaneous locomotor activity of mice treated with the essential oil or hydroalcoholic extract was significantly decreased. Chemical analysis of the essential oil by Gas chromatography-mass spectromentry (GC-MS) showed that 3-butylidene-4,5-dihydrophthalide (85.9 percent) was the major component. CONCLUSION: These data confirm the sedative properties of K. odoratissima, yet there were no profound anxiolytic effects observed.

Bioactivity of major components from the seeds of bunium persicum [boiss.] fedtch

Zire Kermani [Bunium persicum] is an Iranian plant which is commonly used as antispasmodic, carminative, anti obesity and lactogage. The essential oil and different extracts of the seeds of this plant were evaluated for antioxidant activity by three complementary methods: DPPH assay, beta-carotene bleaching and ammonium thiocyanate methods. The oil and methanolic extract of B. persicum exhibited the highest antioxidant activity with IC50=23.4 +/- 1.6 and 45.7 +/- 3.6 micro gmL-1 in DPPH assay and the most inhibition of beta-carotene oxidation and lipid peroxidation. The GC/MS analysis of the essential oil of B. persicum indicated the gamma-Terpinene [46.1%] and cuminaldehyde [15.5%] as the major components of the oil. Furthermore the active methanol extract of the plant was fractioned by column chromatography to afford several fractions, of which in more purification, kaempferol, caffeic acid and p-coumaric acid were found to be the antioxidant components of this extract. These results confirm the in vitro antioxidant and radical scavenging activity of the essential oil and methanolic extract of B. persicum, which warranty the use of the plant in many traditional uses

Induction of programmed cell death by Prangos uloptera, a medicinal plant

Inhibition of the cell growth or induction of cell death is the most promising area in cancer therapy. The induction of apoptosis by dichloromethane extract of Prangos uloptera was evaluated on the McCoy cell line. This plant's roots, aerial parts and fruit have medicinal value. Cell growth inhibitory and cell cytotoxicity effects of the extract were assayed by MTT and Trypan-blue tests, respectively. Morphological changes and DNA fragmentation were also evaluated. The viability tests showed 0.49 and 0.3 mg/ml as 50 percent inhibition concentration and 50 percent cytotoxicity concentration after 24 hours of treatment, respectively. Fluorescent microscopy analysis revealed chromatin fragmentation and scanning electron microscopy showed cell shrinkage and cytoplasmic blebbing. These findings were confirmed by DNA fragmentation analysis. The results demonstrated efficient induction of apoptosis by the plant extract in moderate concentrations, but administration of higher concentrations showed that the primary manner of cell death was necrosis.

Coumarins from the aerial parts of Prangos uloptera (Apiaceae) / Cumarinas das partes aéreas de Prangos uloptera (Apiaceae)

Phytochemical studies on the aerial parts of Prangos uloptera, an endemic Iranian species of the genus Prangos, yielded five coumarins, xanthotoxin (1), prangenin (2), scopoletin (3), deltoin (4) and prangolarin (5). The structures of these coumarins were elucidated by spectroscopic means, and the antioxidant potential of 1-5 was evaluated by the DPPH assay. The chemotaxonomic significance of 1-5 is also discussed.

Os estudos fitoquímicos das partes aéreas de Prangos uloptera, uma espécie do gênero Prangos endêmica do Irã, forneceram cinco cumarinas, xantotoxina (1), prangenina (2), escopoletina (3), deltoína (4) e prangolarina (5). As estruturas destas cumarinas foram elucidas através de métodos espectroscópicos e o potencial antioxidante de 1-5 foi avaliado pelo ensaio de DPPH. O significado quimiotaxonômico de 1-5 também é discutido.

Antinociceptive and anti-inflammatory activity of the seed and root extracts of ferula gummosa boiss in mice and rats

Ferula gummosa Boiss [Apiaceae] has been used in Iranian traditional medicine for the relief of stomach pain. In this study, effects of aqueous, methanolic and acetone extracts of the seed and root of this plant in experimental models of acute pain [Tail-flick=TF], chronic pain [Formalin test=FT] and inflammation [Cotton pellet granuloma=CPG] was investigated. The results showed that the highest non-sedative dose of each of these three extracts had no effect in TF. Among the extracts, only the acetone extract of the root could reduce licking and biting time in the late phase of FT, although this effect might be to some extent due to the solvent [Tween 80]. None of the extracts had anti-inflammatory effect in CPG. Preliminary phytochemical analysis of methanol and acetone extracts showed presence of terpenoids and alkaloids and small amounts of cardenolids. The results of our study suggest further evaluation of antinociceptive and anti-inflammatory effects of other kinds of extracts in order to determine the best extract with highest efficacy and lowest side effects

pharmaacognostical study of the roots of cultivated ammi majus l

A phytochemical study of the successive extractives of the roots of Ammi majus L. [Apiaceae] was carried out in comparison with the fruits. Stigmasterol was found as a major constituent, in addition to a sugar alcohol [mannitol], beta-sitosterol and long chain hydrocarbons. The main furanocoumarins present in the fruits of Ammi majus L. [xanthotoxin, imperatorin and bergapten] could not be traced in the root extractives. A macro- and micromorphological study of the roots of Ammi majus L. grown in Egypt was presented. Also, the anti- microbial activity of the aqueous and alcoholic extracts of this plant organ was carried out