RESUMEN
Stachys lavandulifolia Vahl. subsp. lavandulifolia (Lamiaceae) is widely used in south Anatolia as a herbal tea. It is used for the treatment of gastrointestinal and respiratory disorders. Constituents of the essential oil obtained by hydrodistillation were analyzed both by GC-FID and GC/MS, simultaneously. Thirty-seven compounds representing 98.3% of the oil were characterized. Beta-Phellandrene (27%), alpha-pinene (18.5%) and germacrene-D (13%) were found as major components of the oil. Anticandidal, antibacterial and antioxidant properties of the oil and the prepared infusion were evaluated using several methods. The oil exhibited good inhibitory activity on Candida tropicalis (MIC 0.094 mg/mL). Staphylococcus aureus and Salmonella typhimurium growths were also inhibited by the oil at a concentration of 0.375 mg/mL. The prepared infusion of the flowering aerial parts showed weak antimicrobial effects against all the tested microorganisms, but demonstrated a remarkably radical scavenging activity (IC50: 3.9 microg/mL).
Asunto(s)
Antiinfecciosos/farmacología , Antioxidantes/farmacología , Aceites Volátiles/farmacología , Stachys/química , Cromatografía de Gases y Espectrometría de Masas , Pruebas de Sensibilidad MicrobianaRESUMEN
Terpene derivatives converted by microbial biotransformation constitute an important resource for natural pharmaceutical, fragrance, and aroma substances. In the present study, the monoterpene α-phellandrene was biotransformed by 16 different strains of microorganisms (bacteria, fungi, and yeasts). The transformation metabolites were initially screened by TLC and GC/MS, and then further characterized by NMR spectroscopic techniques. Among the six metabolites characterized, 6-hydroxypiperitone, α-phellandrene epoxide, cis-p-menth-2-en-1-ol, and carvotanacetone, which originated from (-)-(R)-α-phellandrene, are reported for the first time in this study. Additionally, the substrate and the metabolite 5-p-menthene-1,2-diol were subjected to in vitro antibacterial and anticandidal tests. The metabolite showed moderate-to-good inhibitory activities (MICs=0.125 to >4 mg/ml) against various bacteria and especially against Candida species in comparison with its substrate (-)-(R)-α-phellandrene and standard antimicrobial agents.
Asunto(s)
Antibacterianos/metabolismo , Antibacterianos/farmacología , Antifúngicos/metabolismo , Antifúngicos/farmacología , Monoterpenos/metabolismo , Monoterpenos/farmacología , Animales , Antibacterianos/química , Antifúngicos/química , Bacterias/efectos de los fármacos , Bacterias/metabolismo , Infecciones Bacterianas/tratamiento farmacológico , Biotransformación , Candida/efectos de los fármacos , Candidiasis/tratamiento farmacológico , Monoterpenos Ciclohexánicos , Hongos/efectos de los fármacos , Hongos/metabolismo , Humanos , Monoterpenos/química , Micosis/tratamiento farmacológicoRESUMEN
ETHNOPHARMACOLOGICAL RELEVANCE: Capparis ovata Desf. has wide natural distribution in Turkey and it is consumed in pickled form. Flower buds, root bark, and fruits of the plant are used traditionally due to their analgesic, anti-inflammatory, wound healing, anti-rheumatismal, tonic, and diuretic effects. AIM OF THE STUDY: The aim of this study was to investigate the possible anti-inflammatory and anti-thrombotic effects of methanol extracts prepared from flower buds (CBE) and fruits (CFE) of C. ovata. MATERIALS AND METHODS: Anti-inflammatory effects of CBE and CFE were assessed using carrageenan-induced and prostaglandin E2-induced mouse paw edema models. For the anti-thrombotic effect evaluation, carrageenan-induced tail thrombosis model was performed in mice. The extracts were administered intraperitonally (i.p.) at the doses of 100, 200, and 300 mg/kg. The anti-inflammatory effect of Capparis extracts were tested in comparison to 10 mg/kg diclofenac and anti-thrombotic activity to 10 and 100 IU heparin. RESULTS: CBE at the doses of 200, and 300 mg/kg and CFE at the doses of 100, 200, and 300 mg/kg showed significant anti-inflammatory activity and CFE reached therapeutic concentration early than CBE in carrageenan inflammation model. In prostaglandin E2 inflammation model, CBE and CFE exhibited significant inhibitory effects. The C. ovata extracts did not show remarkable anti-thrombotic effect. CONCLUSIONS: Based on the results obtained, it can be concluded that fruits of C. ovata have more potent anti-inflammatory effect than flower buds. It has been suggested that inhibition of cyclooxygenase pathway is one of the mechanisms of the activity. C. ovata may be potentially used as therapeutic agents for inflammatory diseases.
Asunto(s)
Antiinflamatorios/uso terapéutico , Capparis , Edema/tratamiento farmacológico , Fitoterapia , Extractos Vegetales/uso terapéutico , Animales , Carragenina , Dinoprostona , Edema/inducido químicamente , Fibrinolíticos/uso terapéutico , Flores , Frutas , Metanol/química , Ratones , Trombosis/inducido químicamente , Trombosis/tratamiento farmacológicoRESUMEN
Incubation of alpha-cedrol and caryophyllene oxide with Neurospora crassa afforded 12beta-hydroxy cedrol, 10alpha-hydroxy cedrol, and 3beta-hydroxy cedrol, and 12beta-hydroxy caryophyllene oxide as major metabolites, respectively. The antibacterial and radical scavenging activities of the metabolites were evaluated in vitro using broth microdilution and bioauthographic techniques. However, no significant antibacterial and antioxidant activities were observed when compared with those of standard substances.
Asunto(s)
Antibacterianos/metabolismo , Depuradores de Radicales Libres/metabolismo , Neurospora crassa/metabolismo , Sesquiterpenos/metabolismo , Terpenos/metabolismo , Antibacterianos/química , Antibacterianos/farmacología , Biotransformación , Compuestos de Bifenilo/química , Depuradores de Radicales Libres/química , Depuradores de Radicales Libres/farmacología , Pruebas de Sensibilidad Microbiana , Picratos/química , Sesquiterpenos Policíclicos , Sesquiterpenos/química , Sesquiterpenos/farmacología , Terpenos/química , Terpenos/farmacologíaRESUMEN
PURPOSE: Breast cancer is one of the most prevalent woman cancers. Genomic instability, accumulative mutations, and subsequent changes in intracellular signaling cascades play key roles in the development of human breast cancers. Activation of nuclear factor-kappaB (NF-kappaB) has been implicated in oncogenesis of breast cancers and is known to be associated with resistance to anticancer agents and apoptosis. Blocking NF-kappaB signaling may represent a therapeutic strategy in breast cancer therapy. The objective of this study is to investigate the in vitro effects of epoxypseudoisoeugenol-2-methyl butyrate (EPB), a phenylpropranoid isolated from Pimpinella corymbosa, on the activation of NF-kappaB, cell growth, cell cycle progression and apoptosis in MCF-7 (estrogen-dependent) and BT-549 (estrogen-independent) breast cancer cells. METHODS: Transcriptional activity of NF-kappaB was measured by cell based reporter gene assay. Cell proliferation was determined by MTT assay. Cell cycle analysis was carried out by flow cytometry and apoptosis was observed by DAPI staining assy. RESULTS: EPB inhibited the NF-kappaB-mediated transcription activity induced by tumor necrosis factor-alpha (TNF-alpha) and phorbol myristate acetate (PMA) in MCF-7 cells. EPB also inhibited constitutive NF-kappaB transcriptional activity in BT-549 cells. EPB inhibited the proliferation of both MCF-7 and BT-549 cells in a concentration- and time-dependent manner. EPB induced cell cycle arrest in G(1)/G(0) phase and apoptosis in both MCF-7 and BT 549 cells. CONCLUSIONS: These in vitro results indicated that EPB has a potential for use against both hormone-dependent and hormone-independent breast cancers and its effects seem to be mediated by inhibiting the NF-kappaB activity.
Asunto(s)
Apoptosis/efectos de los fármacos , Neoplasias de la Mama/patología , Butiratos/farmacología , FN-kappa B/genética , Transcripción Genética/efectos de los fármacos , Neoplasias de la Mama/tratamiento farmacológico , Neoplasias de la Mama/metabolismo , Ciclo Celular/efectos de los fármacos , Línea Celular Tumoral , Núcleo Celular/metabolismo , Proliferación Celular/efectos de los fármacos , Femenino , Humanos , FN-kappa B/metabolismo , Fenilpropionatos/química , Fenilpropionatos/farmacología , Pimpinella/química , Transducción de SeñalRESUMEN
Essential oils that were extracted by steam distillation from Origanum onites L. from northwest Turkey were analyzed using an Agilent GC-MSD system. Carvacrol was the major component (64.3%) of the oil. Both pure commercial carvacrol and essential oil at concentrations of 1.5%, 3.2%, 6.25%, 12.5%, 25%, 50%, and 100% (v/v) were tested for their effects against engorging Rhipicephalus turanicus, which were collected from cattle breeding in the region. Pure carvacrol killed all the ticks following 6 h of exposure, while 25% and higher concentrations of the oil were completely effective in killing the ticks by the 24th-hour post-treatment (p < 0.05). The concentrations of 6.25% and 12.5% killed all the ticks by day 2. Lethal concentrations for 50% (LC(50)) and 90% (LC(90)) of 2.34% and 7.12%, respectively, were detected 24 h post-treatment. These findings indicate that the essential oil of O. onites L. has potential to be utilized at reasonable concentrations to control tick infestations.
Asunto(s)
Insecticidas/farmacología , Aceites Volátiles/farmacología , Origanum/química , Aceites de Plantas/farmacología , Rhipicephalus/efectos de los fármacos , Animales , Femenino , Larva/efectos de los fármacos , Masculino , Aceites Volátiles/química , Aceites de Plantas/química , Rhipicephalus/crecimiento & desarrollo , TurquíaRESUMEN
Pimpinella essential oils and isolated compounds were screened for their inhibitory activity against NF-kappaB mediated transcription in SW1353 cells. Twelve oils were effective in inhibiting NF-kappaB mediated transcription. Especially the roots of P. corymbosa, P. tragium and P. rhodanta showed potent activities with IC(50) values of 2, 3 and 6 microg/mL, respectively. Five pure compounds, 7 (4-(2-propenyl)phenylangelate), 12 (4-(3-methyloxiranyl)phenyltiglate), 17 (4-methoxy-2-(3-methyloxiranyl)phenyl isobutyrate), 18 (4-methoxy-2-(3-methyloxiranyl)phenylangelate) and 21 (epoxy pseudoisoeugenol-2-methylbutyrate) inhibited NF-kappaB mediated transcription with IC(50) values of 5.5, 1.2, 0.01, 3.6 and 11 microg/mL, respectively. None of the compounds were cytotoxic to mammalian cells. These findings add significant information to the pharmacological activity of Pimpinella species and their beneficial effects and use in disease prevention especially those related to inflammation.
Asunto(s)
Antiinflamatorios no Esteroideos/farmacología , FN-kappa B/antagonistas & inhibidores , Aceites Volátiles/farmacología , Pimpinella/química , Aceites de Plantas/farmacología , Animales , Antiinflamatorios no Esteroideos/química , Línea Celular , Chlorocebus aethiops , Regulación de la Expresión Génica/efectos de los fármacos , Humanos , Estructura Molecular , Aceites Volátiles/química , Fitoterapia , Componentes Aéreos de las Plantas/química , Aceites de Plantas/química , Raíces de Plantas/química , Especificidad de la EspecieRESUMEN
Essential oils from 15 Pimpinella species were analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) techniques. One species, Pimpinella anisum, in which only fruits were evaluated, was also included in the study. A total of 140 different compounds were identified and significant qualitative and quantitative differences were observed among the samples. Pimpinella essential oils were characterized as having mono-, sesqui- and trinorsesquiterpenoids, propenylphenols, and pseudoisoeugenols. Trinorsesquiterpenoids and phenylpropanoids appear to be chemical markers of Pimpinella species analyzed thus far. Essential oils obtained from Pimpinella roots share the same principal compound, epoxypseudoisoeugenyl-2-methylbutyrate at concentrations from 20 to 82.6%.
Asunto(s)
Cromatografía de Gases y Espectrometría de Masas/métodos , Aceites Volátiles/análisis , Pimpinella/química , Especificidad de la Especie , TurquíaRESUMEN
The essential oils obtained by water distillation from aerial parts of Achillea schischkinii Sosn. and Achillea aleppica DC. subsp. aleppica were analyzed by gas chromatography and gas chromatography/mass spectrometry. 1,8-Cineole (32.5 and 26.1%, respectively) was the main component in both oils. The oil of A. aleppica subsp. aleppica was also found to be rich in bisabolol and its derivates. When tested for their antimicrobial, antiinflammatory, and antinociceptive activities, the oil of A. aleppica subsp. aleppica showed significant antiinflammatory, antinociceptive, and moderate antimicrobial activities.
Asunto(s)
Achillea/química , Aceites Volátiles/química , Aceites Volátiles/farmacología , Analgésicos/farmacología , Animales , Antiinfecciosos/farmacología , Antiinflamatorios/farmacología , Ciclohexanoles/análisis , Eucaliptol , Cromatografía de Gases y Espectrometría de Masas , Masculino , Ratones , Monoterpenos/análisisRESUMEN
Essential oils from fruits, stems and leaves and roots of Pimpinella aurea DC., P. corymbosa Boiss., P. peregrina L. were analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) techniques. Fruits and aerial parts of P. puberula (DC.) Boiss were also evaluated. A total of 140 different compounds were identified, and significant qualitative and quantitative differences were observed among the samples. In fact, the main constituents of each species were different and only the oils extracted from roots shared the same principal compound, epoxy pseudoisoeugenyl-2-methyl butyrate (26.8-42.8%). The other fractions were dominated by different sesquiterpene compounds although in three of them, P. aurea stem and leaves, P. puberula fruits and P. puberula stems and leaves, monoterpene constituents also appear as main ones.
Asunto(s)
Cromatografía de Gases y Espectrometría de Masas/métodos , Aceites Volátiles/análisis , Pimpinella/química , Frutas/química , Monoterpenos/análisis , Aceites Volátiles/aislamiento & purificación , Hojas de la Planta/química , Aceites de Plantas/análisis , Aceites de Plantas/aislamiento & purificación , Raíces de Plantas/química , Tallos de la Planta/química , Sesquiterpenos/análisis , Especificidad de la Especie , TurquíaRESUMEN
Essential oils from 23 species of plants comprising 14 genera and 4 plant families were obtained by Clevenger-type water distillation. The major compounds in these essential oils were identified with GC-MS and their insecticidal activity against adult turnip aphids, Lipaphis pseudobrassicae (Davis), tested with dosage-mortality bioassays. We examined mortality only for viviparous adults because sizeable aphid populations on crucifer (Brassicaceae) hosts are largely produced by these wingless, parthenogenic females. Twenty-two of the oils were directly applied to aphid females in randomized blocks at concentrations of 0.0, 1.0, 2.5, 5.0 and 10.0 mg ml(-1). Essential oils mixed with a non-toxic emulsifying agent, dimethyl sulfoxide (DMSO), more easily penetrated the waxy insect cuticle. Probit analysis and LC(50) at three different exposures showed aphids were quickly incapacitated and killed by aliphatic aldehydes, phenols and monocyclic terpenes contained in Bifora and Satureja oils and at applied concentrations as low as 0.3 to 1.0 mg ml(-1). Only enough Pimpinella isaurica oil and its three phenylpropanoid fractions were available for testing at a single concentration of 10 mg ml(-1). We could not spare any additional P. isaurica oil for testing at other concentrations. Phenylpropanoids isolated from P. isaurica oil when recombined or left naturally blended in the oil were highly bioactive against L. pseudobrassicae at 10 mg ml(-1).
Asunto(s)
Áfidos/efectos de los fármacos , Insecticidas/química , Aceites Volátiles/química , Aceites Volátiles/farmacología , Aceites de Plantas/química , Aceites de Plantas/farmacología , Envejecimiento/fisiología , Animales , Relación Dosis-Respuesta a Droga , Femenino , Estructura Molecular , Control Biológico de Vectores , Distribución AleatoriaRESUMEN
A new 'phenylpropanoid', 4-(3-methyloxiran-2-yl)phenyl 2-methylbutanoate (1), a new trinorsesquiterpene, 4-(6-methylbicyclo[4.1.0]hept-2-en-7-yl)butan-2-one (2), and eight known compounds (3-10) were isolated from the essential oils of several Pimpinella species growing in Turkey. The structures of the new compounds were determined by 1D- and 2D-NMR analyses. The absolute configuration of 1 was established via comparison of its optical rotation with that of 'epoxypseudoisoeugenyl 2-methylbutyrate' (11), the absolute configuration of which was determined by chemical degradation and an appropriate Mosher ester formation. Direct bioautography revealed antifungal activity of 1 and 11 against Colletotrichum acutatum, C. fragariae, and C. gloesporioides. Subsequent evaluation of antifungal compounds in a 96-well microtiter assay showed that compounds 1 and 11 produced the most-significant growth inhibition in Phomopsis spp., Colletotrichum spp., and Botrytis cinerea. Compounds 1 and 6 displayed antimicrobial activities against Mycobacterium intracellulare, with IC50 values of 2.78 and 1.29 microM, respectively.
Asunto(s)
Antibacterianos/química , Pimpinella/química , Aceites de Plantas/química , Antibacterianos/farmacología , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Mycobacterium/efectos de los fármacos , Aceites Volátiles/química , Aceites Volátiles/farmacología , Aceites de Plantas/farmacología , TurquíaRESUMEN
Several plants and plant-derived pure compounds, designated as phytoestrogens, have been reported to cause estrogenic effects. They have been used for alleviation of menopausal symptoms, prevention of osteoporosis, heart disease and cancer. There is an increased interest in studying phytoestrogens such as isoflavones and lignans for their use as replacements for synthetic estrogens. In this study, the estrogenic activity of essential oils of eleven Pimpinella species and the compounds isolated from these species were evaluated using the yeast estrogen screen (YES) assay. The essential oils containing (E)-anethole as major compound showed estrogenic activity in the YES assay, except for the aerial parts without fruits of P. anisetum and P. flabellifolia. The percent maximal response produced by most anethole-containing oils was 30-50%. Fruits of P. isaurica and P. peucedanifolia were estrogenic in spite of the absence or trace amount of anethole, respectively. This study indicates that the estrogenic activity of Pimpinella oils is not solely due to the presence of anethole. Components other than anethole may be responsible for contributing towards the estrogenic activity. The essential oils from different species varied in their estrogenic potencies (relative potency from 8.3 x 10(-8) to 1.2 x 10(-6) compared to 17 beta-estradiol) and among the different plant parts, the fruit oils of most species were estrogenic followed by the aerial parts without fruits and the root oils and their EC50 values varied from 45 micrograms/mL to 650 micrograms/mL.
Asunto(s)
Isoflavonas/farmacología , Fitoterapia , Pimpinella , Aceites de Plantas/farmacología , Preparaciones de Plantas/farmacología , Relación Dosis-Respuesta a Droga , Frutas , Humanos , Isoflavonas/administración & dosificación , Isoflavonas/química , Isoflavonas/uso terapéutico , Fitoestrógenos , Componentes Aéreos de las Plantas , Aceites de Plantas/administración & dosificación , Aceites de Plantas/química , Aceites de Plantas/uso terapéutico , Preparaciones de Plantas/administración & dosificación , Preparaciones de Plantas/química , Preparaciones de Plantas/uso terapéutico , Raíces de Plantas , Saccharomyces cerevisiae/efectos de los fármacos , Saccharomyces cerevisiae/metabolismoRESUMEN
The cyclic monoterpene ketone (-)-carvone was metabolized by the plant pathogenic fungus Absidia glauca. After 4 days of incubation, the diol 10-hydroxy-(+)-neodihydrocarveol was formed. The absolute configuration and structure of the crystalline substance was identified by means of X-ray diffraction and by spectroscopic techniques (MS, IR and NMR). The antimicrobial activity of the substrate and metabolite was assayed with human pathogenic microorganisms.
Asunto(s)
Absidia/metabolismo , Antineoplásicos Fitogénicos/metabolismo , Monoterpenos/metabolismo , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Bacterias/efectos de los fármacos , Biotransformación , Candida albicans/efectos de los fármacos , Monoterpenos Ciclohexánicos , Cromatografía de Gases y Espectrometría de Masas , Cetoconazol/farmacología , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Monoterpenos/química , Monoterpenos/farmacología , Espectrofotometría Infrarroja , Espectroscopía Infrarroja por Transformada de FourierRESUMEN
A new, 4-(2-propenyl)-phenyl angelate ( 1) and four known phenylpropanoids ( 2 - 5), were isolated from Pimpinella isaurica, a species endemic in Turkey. One new sesquiterpene, 1-methyl-4-(5-methyl-1-methylenehex-4-enyl)-7-oxabicyclo[4.1.0]heptane ( 6) was obtained from P. aurea and two known phenylpropanoids were isolated ( 7, 8), from P. corymbosa. The structure elucidation of the new compounds 1 and 6 was achieved by a combination of one- ( (1)H, and (13)C) and two-dimensional NMR techniques (G-DQF-COSY, G-HMQC, and G-HMBC) and LC-ESI-FTMS. Compounds 1, 2, 4, 6, 7, 8 have been evaluated for their antimalarial and antimicrobial activities. Compound 1, 2, 4, 6, 8 had antimicrobial activity against Mycobacterium intracellulare with IC (50) values of 7.0, 15.0, 2.5, 10.0 and 1.5 microg/mL, respectively.
Asunto(s)
Antiinfecciosos/farmacología , Antimaláricos/farmacología , Complejo Mycobacterium avium/efectos de los fármacos , Fitoterapia , Pimpinella , Extractos Vegetales/farmacología , Animales , Antiinfecciosos/administración & dosificación , Antiinfecciosos/uso terapéutico , Antimaláricos/administración & dosificación , Antimaláricos/uso terapéutico , Humanos , Pruebas de Sensibilidad Microbiana , Pruebas de Sensibilidad Parasitaria , Componentes Aéreos de las Plantas , Extractos Vegetales/administración & dosificación , Extractos Vegetales/uso terapéutico , Raíces de Plantas , Plasmodium falciparum/efectos de los fármacosRESUMEN
Essential oils of peppermint Mentha piperita L. (Lamiaceae), which are used in flavors, fragrances, and pharmaceuticals, were investigated for their antimicrobial properties against 21 human and plant pathogenic microorganisms. The bioactivity of the oils menthol and menthone was compared using the combination of in vitro techniques such as microdilution, agar diffusion, and bioautography. It was shown that all of the peppermint oils screened strongly inhibited plant pathogenic microorganisms, whereas human pathogens were only moderately inhibited. Chemical compositions of the oils were analyzed by GC and GC/MS. Using the bioautography assay, menthol was found to be responsible for the antimicrobial activity of these oils.