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1.
Plants (Basel) ; 12(9)2023 Apr 30.
Artículo en Inglés | MEDLINE | ID: mdl-37176915

RESUMEN

This study represents a comparative analysis of secondary metabolites content, antioxidant, and antimicrobial activity of 24 halophytes from coastal saline habitats of the Balkan Peninsula (Montenegro, Albania, and Greece). Total content of phenolics, flavonoids, tannins, anthocyanins, antioxidant, and antimicrobial activity was determined for dry methanolic (DME) and crude water extracts (CWE) and compared with well-known medicinal plants. The total phenolic content ranged from 13.23 to 376.08 mg of GA/g of DME, and from 33.68 to 511.10 mg/mL of CWE. The content of flavonoids ranged from 12.63 to 77.36 mg of RU/g of DME, and from 12.13 to 26.35 mg/mL of CWE. Total tannins and anthocyanins varied from 0.05 to 2.44 mg/mL, and from 1.31 to 39.81 µg/L, respectively. The antioxidant activity ranged from 1147.68 to 15.02 µg/mL for DME and from 1613.05 to 21.96 µg/mL for CWE. The best antioxidant properties, and the highest content of phenolic compounds, were determined for Polygonum maritimum and Limonium vulgare with values similar to or higher compared to the medicinal plants. Halophytes with significant antimicrobial potential were Limonium vulgare, L. angustifolium, and Artemisia maritima. Some of the analyzed coastal halophytes can be considered rich natural sources of phenolic compounds, with favorable antioxidative and antimicrobial properties.

2.
Plants (Basel) ; 11(23)2022 Dec 01.
Artículo en Inglés | MEDLINE | ID: mdl-36501379

RESUMEN

Motivated by the ethnopharmacological use of Pulicaria dysenterica, in the present study, the antimicrobial potential of the extracted essential oil was investigated against a panel of eighteen microorganism strains. Additionally, anti-acetylcholinesterase and antispasmodic (isolated rat distal colon) activities, general acute toxicity (Artemia salina model), and immunomodulatory properties (cytotoxicity on isolated mouse macrophages) were studied. Detailed analyses of the essential oil led to the identification of 3-methoxycuminyl 2-methylbutanoate (a new natural product) and 3-methoxycuminyl 3-methylbutanoate (a rare natural product). The obtained esters and intermediates in the synthesis of the starting alcohol (3-methoxycuminol) were subjected to a battery of 1D- and 2D-NMR experiments. The synthesized esters were additionally characterized by GC-MS, IR, and UV-Vis. The synthesized compounds (ten in total) were biologically tested in the same way as the extracted P. dysenterica essential oil. The obtained low acute toxicity and promising antimicrobial potential suggest that the P. dysenterica essential oil might partially explain the ethnopharmacological application of P. dysenterica plant material for the treatment of gastrointestinal infections.

3.
Food Chem Toxicol ; 158: 112666, 2021 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-34762977

RESUMEN

Immortelle (Helichrysum italicum, Asteraceae) essential oil has been widely used in alternative medicine to accelerate wound healing, as well as in cosmetic products to stimulate skin regeneration and to reduce the appearance of wrinkles. It is also considered a natural and safe culinary spice that could also be applied in the food industry as a preservative in the future. The therapeutic efficacy of this oil changes with the natural variability of the composition. Herein we tested and mutually compared the antimicrobial and anti-inflammatory activities of four commercial immortelle oils differing in the relative amounts of marker compounds, i.e. neryl esters, α-pinene, γ- and ar-curcumenes, and ß-diketones. The anti-inflammatory effect of selected chromatographic fractions, enriched in the aforementioned constituents, was evaluated by studying toxicity toward rat peritoneal macrophages, their nitric oxide production, myeloperoxidase, and arginase activities. Subsequently, the compositional and activity data were subjected to a multivariate statistical treatment to reveal the possible correlation(s) between the percentage of essential-oil constituents and the observed activities. The obtained results imply that immortelle oil efficiency as an antimicrobial and/or anti-inflammatory agent is most plausibly a result of a synergistic action between its constituents, and/or, rather unexpectedly, the presence of some minor constituents.


Asunto(s)
Antiinfecciosos/farmacología , Antiinflamatorios/farmacología , Helichrysum/química , Aceites Volátiles/farmacología , Aceites de Plantas/farmacología , Animales , Antiinfecciosos/análisis , Antiinflamatorios/análisis , Bacterias/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Células Cultivadas , Cromatografía de Gases y Espectrometría de Masas , Macrófagos Peritoneales/efectos de los fármacos , Masculino , Aceites Volátiles/análisis , Aceites de Plantas/análisis , Ratas , Ratas Wistar
4.
Chem Biodivers ; 18(9): e2100424, 2021 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-34216094

RESUMEN

The present article investigates the chemical composition of volatiles of essential oil (EO) and headspace (HS) fraction, as well as biological activities of EO obtained from needles with twigs of Pseudotsuga menziesii var. menziesii cultivated in Serbia. The major class of compounds was monoterpene hydrocarbons with α-terpinolene, sabinene and ß-pinene (EO), and sabinene, α-terpinolene and ß-pinene (HS) as the dominant volatiles. Tested EO exhibited mostly low antimicrobial potential against investigated strains (ATCC and respiratory isolates), where MICs ranged 1.25-20.00 mg/mL. Nevertheless, based on presented results, where antimicrobial testing was done for the first time on human respiratory system isolates, there is a potential of this EO to be used as an adjuvant in the treatment of human respiratory infections, especially those caused by Pseudomonas aeruginosa or Candida albicans strains. Regarding toxicological evaluation, EO showed moderate toxicity in Artemia salina toxicity bioassay (LC50 =347.41, after 24 h) as well as week toxicity against Drosophila melanogaster with the ability only to moderately delay larval and pupal development.


Asunto(s)
Antibacterianos/farmacología , Antifúngicos/farmacología , Aceites Volátiles/farmacología , Extractos Vegetales/farmacología , Pseudotsuga/química , Compuestos Orgánicos Volátiles/farmacología , Animales , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Artemia/efectos de los fármacos , Candida albicans/efectos de los fármacos , Drosophila melanogaster/efectos de los fármacos , Humanos , Pruebas de Sensibilidad Microbiana , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Brotes de la Planta/química , Pseudomonas aeruginosa/efectos de los fármacos , Compuestos Orgánicos Volátiles/química , Compuestos Orgánicos Volátiles/aislamiento & purificación
5.
Medicina (Kaunas) ; 56(9)2020 Aug 27.
Artículo en Inglés | MEDLINE | ID: mdl-32867260

RESUMEN

The positive impact of probiotic strains on human health has become more evident than ever before. Often delivered through food, dietary products, supplements, and drugs, different legislations for safety and efficacy issues have been prepared. Furthermore, regulatory agencies have addressed various approaches toward these products, whether they authorize claims mentioning a disease's diagnosis, prevention, or treatment. Due to the diversity of bacteria and yeast strains, strict approaches have been designed to assess for side effects and post-market surveillance. One of the most essential delivery systems of probiotics is within food, due to the great beneficial health effects of this system compared to pharmaceutical products and also due to the increasing importance of food and nutrition. Modern lifestyle or various diseases lead to an imbalance of the intestinal flora. Nonetheless, as the amount of probiotic use needs accurate calculations, different factors should also be taken into consideration. One of the novelties of this review is the presentation of the beneficial effects of the administration of probiotics as a potential adjuvant therapy in COVID-19. Thus, this paper provides an integrative overview of different aspects of probiotics, from human health care applications to safety, quality, and control.


Asunto(s)
Infecciones por Coronavirus/prevención & control , Suplementos Dietéticos/normas , Enfermedades Gastrointestinales/terapia , Hepatopatías/terapia , Pandemias/prevención & control , Neumonía Viral/prevención & control , Probióticos/uso terapéutico , Betacoronavirus , COVID-19 , Enfermedad Celíaca/terapia , Infecciones por Clostridium/terapia , Estreñimiento/terapia , Infecciones por Coronavirus/tratamiento farmacológico , Infecciones por Coronavirus/terapia , Trastorno Depresivo/terapia , Enfermedades Diverticulares/terapia , Disentería/terapia , Enterocolitis Necrotizante/terapia , Alimentos Fermentados , Hipersensibilidad a los Alimentos/terapia , Infecciones por Helicobacter/terapia , Encefalopatía Hepática/terapia , Humanos , Enfermedades Inflamatorias del Intestino/terapia , Enfermedad del Hígado Graso no Alcohólico/terapia , Neumonía Viral/terapia , Probióticos/efectos adversos , Probióticos/normas , Control de Calidad , SARS-CoV-2 , Tratamiento Farmacológico de COVID-19
6.
Biotechnol Adv ; 44: 107629, 2020 11 15.
Artículo en Inglés | MEDLINE | ID: mdl-32896577

RESUMEN

Tuberculosis is a highly infectious disease declared a global health emergency by the World Health Organization, with approximately one third of the world's population being latently infected with Mycobacterium tuberculosis. Tuberculosis treatment consists in an intensive phase and a continuation phase. Unfortunately, the appearance of multi drug-resistant tuberculosis, mainly due to low adherence to prescribed therapies or inefficient healthcare structures, requires at least 20 months of treatment with second-line, more toxic and less efficient drugs, i.e., capreomycin, kanamycin, amikacin and fluoroquinolones. Therefore, there exists an urgent need for discovery and development of new drugs to reduce the global burden of this disease, including the multi-drug-resistant tuberculosis. To this end, many plant species, as well as marine organisms and fungi have been and continue to be used in various traditional healing systems around the world to treat tuberculosis, thus representing a nearly unlimited source of active ingredients. Besides their antimycobacterial activity, natural products can be useful in adjuvant therapy to improve the efficacy of conventional antimycobacterial therapies, to decrease their adverse effects and to reverse mycobacterial multi-drug resistance due to the genetic plasticity and environmental adaptability of Mycobacterium. However, even if some natural products have still been investigated in preclinical and clinical studies, the validation of their efficacy and safety as antituberculosis agents is far from being reached, and, therefore, according to an evidence-based approach, more high-level randomized clinical trials are urgently needed.


Asunto(s)
Antiinfecciosos , Mycobacterium tuberculosis , Plantas Medicinales , Tuberculosis , Antituberculosos/uso terapéutico , Humanos , Tuberculosis/tratamiento farmacológico
7.
Cell Mol Biol (Noisy-le-grand) ; 66(4): 45-53, 2020 Jun 25.
Artículo en Inglés | MEDLINE | ID: mdl-32583789

RESUMEN

Pediatric infections still represent a leading cause of mortality in many developing countries. Since ancient times, traditional healing systems provided some herbal remedies to treat pediatric diseases, only in some cases validated by an evidence-based approach. Therefore, this review covers the herbal remedies in Iranian traditional medicine and aims to assess the potential of phytotherapeutics as safe and effective alternatives to conventional therapies for the treatment of pediatric infectious diseases. Notably, pediatric patients may also benefit from adjuvant therapy, i.e., combined treatment with herbal remedies and conventional therapies, to improve the efficacy of conventional drugs, decrease their adverse effects at the cell-tissue-organ-organism level and reduce the occurrence of microbial strains resistant to antibiotics. Therefore, traditional healing systems still represent an unlimited source of active ingredients to be tested in preclinical assays as well as in humans in terms of efficacy and safety.


Asunto(s)
Enfermedades Transmisibles/tratamiento farmacológico , Fitoterapia , Niño , Ensayos Clínicos como Asunto , Humanos , Medicina Tradicional , Fitoquímicos/química , Fitoquímicos/farmacología
8.
J Clin Med ; 9(3)2020 Mar 10.
Artículo en Inglés | MEDLINE | ID: mdl-32164244

RESUMEN

Cardiovascular diseases (CVD) compromises a group of heart and blood vessels disorders with high impact on human health and wellbeing. Curcumin (CUR) have demonstrated beneficial effects on these group of diseases that represent a global burden with a prevalence that continues increasing progressively. Pre- and clinical studies have demonstrated the CUR effects in CVD through its anti-hypercholesterolemic and anti-atherosclerotic effects and its protective properties against cardiac ischemia and reperfusion. However, the CUR therapeutic limitation is its bioavailability. New CUR nanomedicine formulations are developed to solve this problem. The present article aims to discuss different studies and approaches looking into the promising role of nanotechnology-based drug delivery systems to deliver CUR and its derivatives in CVD treatment, with an emphasis on their formulation properties, experimental evidence, bioactivity, as well as challenges and opportunities in developing these systems.

9.
Eur J Med Chem ; 163: 527-545, 2019 Feb 01.
Artículo en Inglés | MEDLINE | ID: mdl-30553144

RESUMEN

Curcuma longa L., its derived extracts and even its major compound curcumin has a long history of use and doubtless effectiveness, reported through increasingly detailed in vitro, ex vivo, in vivo and even clinical trials. Regarding its biological effects, multiple health-promoting, disease-preventing and even treatment attributes has been remarkably highlighted. Clinical trials, although have increased in a progressive manner, significant disproportionalities have been stated in terms of biological effects assessment. In this sense, the present report aims to provide an extensive overview to curcumin therapeutic effects in human subjects. For that, clinical trials assessing the curcumin effect on inflammation, skin, eye, central nervous system, respiratory, cardiovascular, gastrointestinal, urogenital and metabolic disorders are here presented and discussed. A special emphasis was also given to curcumin activity on intoxications and multiple malignant diseases.


Asunto(s)
Ensayos Clínicos como Asunto , Curcumina/uso terapéutico , Curcuma/química , Humanos , Inflamación/tratamiento farmacológico , Enfermedades Metabólicas/tratamiento farmacológico
10.
Plants (Basel) ; 7(3)2018 Sep 04.
Artículo en Inglés | MEDLINE | ID: mdl-30181483

RESUMEN

Genus Mentha, a member of Lamiaceae family, encompasses a series of species used on an industrial scale and with a well-described and developed culture process. Extracts of this genus are traditionally used as foods and are highly valued due to the presence of significant amounts of antioxidant phenolic compounds. Many essential oil chemotypes show distinct aromatic flavor conferred by different terpene proportions. Mint extracts and their derived essential oils exert notable effects against a broad spectrum of bacteria, fungi or yeasts, tested both in vitro or in various food matrices. Their chemical compositions are well-known, which suggest and even prompt their safe use. In this review, genus Mentha plant cultivation, phytochemical analysis and even antimicrobial activity are carefully described. Also, in consideration of its natural origin, antioxidant and antimicrobial properties, a special emphasis was given to mint-derived products as an interesting alternative to artificial preservatives towards establishing a wide range of applications for shelf-life extension of food ingredients and even foodstuffs. Mentha cultivation techniques markedly influence its phytochemical composition. Both extracts and essential oils display a broad spectrum of activity, closely related to its phytochemical composition. Therefore, industrial implementation of genus Mentha depends on its efficacy, safety and neutral taste.

11.
J Food Sci Technol ; 55(8): 2910-2925, 2018 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-30065400

RESUMEN

Many Eryngium species have been traditionally used as ornamental, edible or medicinal plants. The gas chromatography-flame ionization detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS) analyses have shown that the major compounds in the aerial parts were spathulenol (in E. campestre and E. palmatum oils) and germacrene D (in E. amethystinum oil). The main compounds in the root oil were nonanoic acid, 2,3,4-trimethylbenzaldehyde and octanoic acid for E. campestre, E. amethystinum and E. palmatum, respectively. All the oils expressed the highest potential against Gram-positive bacteria Staphylococcus aureus as well as Gram-negative Klebsiella pneumoniae and Proteus mirabilis. Molecular docking analysis was used for determining a potential antibacterial activity mechanism of compounds present in the essential oils. Molecular docking confirmed that the binding affinity of spathulenol to the active site of tyrosyl-tRNA synthetase was the highest among the tested dominant compounds. Regarding the total phenolic content (determined by the Folin-Ciocalteu assay) and flavonoid content (evaluated using aluminum nitrate nonahydrate), the highest amount was found in the ethyl acetate extract of E. palmatum. The results of DPPH and ABTS assay indicated that the highest antioxidant activity was present in the water extract of E. amethystinum. Extracts of the aerial parts presented as minimum inhibitory concentration (MIC) expressed the activity in the range 0.004-20.00 mg/mL, with the highest activity exhibited by the acetone and ethyl acetate extracts against Proteus mirabilis. The obtained results suggest that Eryngium species may be considered a beneficial native source of the compounds with antioxidant and antimicrobial properties.

12.
Biotechnol Adv ; 2017 07 08.
Artículo en Inglés | MEDLINE | ID: mdl-28694178

RESUMEN

Tuberculosis is a highly infectious disease declared a global health emergency by the World Health Organization, with approximately one third of the world's population being latently infected with Mycobacterium tuberculosis. Tuberculosis treatment consists in an intensive phase and a continuation phase. Unfortunately, the appearance of multi drug-resistant tuberculosis, mainly due to low adherence to prescribed therapies or inefficient healthcare structures, requires at least 20months of treatment with second-line, more toxic and less efficient drugs, i.e., capreomycin, kanamycin, amikacin and fluoroquinolones. Therefore, there exists an urgent need for discovery and development of new drugs to reduce the global burden of this disease, including the multi-drug-resistant tuberculosis. To this end, many plant species, as well as marine organisms and fungi have been and continue to be used in various traditional healing systems around the world to treat tuberculosis, thus representing a nearly unlimited source of active ingredients. Besides their antimycobacterial activity, natural products can be useful in adjuvant therapy to improve the efficacy of conventional antimycobacterial therapies, to decrease their adverse effects and to reverse mycobacterial multi-drug resistance due to the genetic plasticity and environmental adaptability of Mycobacterium. However, even if some natural products have still been investigated in preclinical and clinical studies, the validation of their efficacy and safety as antituberculosis agents is far from being reached, and, therefore, according to an evidence-based approach, more high-level randomized clinical trials are urgently needed.

13.
Food Chem Toxicol ; 105: 355-369, 2017 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-28472675

RESUMEN

Neurotoxic thujones (α- and ß-diastereoisomers) are common constituents of plant essential oils. In this study, we employed a statistical approach to determine the contribution of thujones to the overall observed behaviour-modulating and toxic effects of essential oils (Salvia officinalis L., Artemisia absinthium L., Thuja occidentalis L. and Tanacetum vulgare L.) containing these monoterpene ketones. The data from three in vivo neuropharmacological tests on rats (open field, light-dark, and diazepam-induced sleep), and toxicity assays (brine shrimp, and antimicrobial activity against a panel of microorganisms), together with the data from detailed chemical analyses, were subjected to a multivariate statistical treatment to reveal the possible correlation(s) between the content of essential-oil constituents and the observed effects. The results strongly imply that the toxic and behaviour-modulating activity of the oils (hundreds of constituents) should not be associated exclusively with thujones. The statistical analyses pinpointed to a number of essential-oil constituents other than thujones that demonstrated a clear correlation with either the toxicity, antimicrobial effect or the activity on CNS. Thus, in addition to the thujone content, the amount and toxicity of other constituents should be taken into consideration when making risk assessment and determining the regulatory status of plants in food and medicines.


Asunto(s)
Artemisia absinthium/química , Aceites Volátiles/toxicidad , Aceites de Plantas/toxicidad , Salvia officinalis/química , Tanacetum/química , Thuja/química , Animales , Artemisia absinthium/toxicidad , Cromatografía de Gases y Espectrometría de Masas , Masculino , Aceites Volátiles/análisis , Aceites de Plantas/análisis , Ratas , Ratas Wistar , Salvia officinalis/toxicidad , Tanacetum/toxicidad , Thuja/toxicidad
14.
Chem Biodivers ; 12(9): 1378-97, 2015 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-26363882

RESUMEN

Detailed GC and GC-MS analyses of the essential oils and Et2 O extracts of two Xeranthemum species - X. cylindraceum and X. annum - resulted in the identification of 254 components, in total. Terpenoids constituted the major part of both X. cylindraceum and X. annum essential oils and extracts (51.8-65.7%, and 50.7%, resp.). Among the sesquiterpenoids, the extracts of both investigated taxa contained the guaianolide xerantholide, its 11,13-dihydro derivatives, and two additional sesquiterpene lactones: an eudesmanolide, 11,13-dihydroisoalantolactone, and a pseudoguaianolide, confertin. The last two lactones and both isomers of 11,13-dihydroxerantholide have not been previously detected in Xeranthemum species. The isolated extracts of X. cylindraceum and X. annum were tested in a broth microdilution assay against a panel of microorganisms. The tested extracts demonstrated significant antimicrobial inhibitory activity, ranging from 30 to 260 µg/ml, being most active against Bacillus cereus and Staphylococcus aureus, an important human pathogen, with MIC close in value to those of chloramphenicol. Chemotaxonomic significance of the sesquiterpene lactones' distribution in the taxa investigated in this study and those detected earlier in phylogenetically close species (up to the level of the tribe Cardueae) was also discussed.


Asunto(s)
Antiinfecciosos/química , Asteraceae/química , Lactonas/química , Aceites Volátiles/química , Extractos Vegetales/química , Sesquiterpenos/química , Antiinfecciosos/aislamiento & purificación , Antiinfecciosos/farmacología , Asteraceae/clasificación , Bacterias/efectos de los fármacos , Infecciones Bacterianas/tratamiento farmacológico , Candida albicans/efectos de los fármacos , Candidiasis/tratamiento farmacológico , Cromatografía de Gases y Espectrometría de Masas , Humanos , Lactonas/aislamiento & purificación , Lactonas/farmacología , Aceites Volátiles/aislamiento & purificación , Aceites Volátiles/farmacología , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología
15.
Comput Biol Med ; 54: 72-8, 2014 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-25217763

RESUMEN

In the current work, in vitro antioxidant, antibacterial, and antifungal activites of the needle terpenes of three taxa of Pinus nigra from Serbia (ssp. nigra, ssp. pallasiana, and var. banatica) were analyzed. The black pine essential oils showed generally weak antioxidative properties tested by two methods (DPPH and ABTS scavenging assays), where the highest activity was identified in P. nigra var. banatica (IC50=25.08 mg/mL and VitC=0.67 mg (vitamin C)/g when tested with the DPPH and ABTS reagents, respectively). In the antimicrobial assays, one fungal (Aspergilus niger) and two bacterial strains (Staphylococcus aureus and Bacillus cereus) showed sensitivity against essential oils of all three P. nigra taxa. The tested oils have been shown to possess inhibitory action in the range from 20.00 to 0.62 mg/mL, where var. banatica exhibited the highest and ssp. nigra the lowest antimicrobial action. In order to determine potential compounds that are responsible for alternative mode of action, molecular docking simulations inside FtsZ (a prokaryotic homolog of tubulin) were performed. Tested compounds were the most abundant terpenoid (germacrene D-4-ol) and its structurally similar terpene (germacrene D), both present in all three essential oils. It was determined that the oxygenated form of the molecule creates stable bonds with investigated enzyme FtsZ, and that this compound, through this mechanism of action participates in the antimicrobial activity.


Asunto(s)
Antiinfecciosos/administración & dosificación , Fenómenos Fisiológicos Bacterianos/efectos de los fármacos , Proteínas Bacterianas/antagonistas & inhibidores , Proteínas del Citoesqueleto/antagonistas & inhibidores , Hongos/efectos de los fármacos , Aceites Volátiles/administración & dosificación , Pinus/química , Terpenos/administración & dosificación , Antiinfecciosos/química , Apoptosis/efectos de los fármacos , Apoptosis/fisiología , Supervivencia Celular/efectos de los fármacos , Supervivencia Celular/fisiología , Relación Dosis-Respuesta a Droga , Hongos/fisiología , Aceites Volátiles/química , Pinus/clasificación , Aceites de Plantas/administración & dosificación , Aceites de Plantas/química , Terpenos/química
16.
Chem Biodivers ; 11(4): 542-50, 2014 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-24706624

RESUMEN

4,5- and 1,10-Epoxygermacrones were isolated from the essential oil of aerial parts of Geranium macrorrhizum L. (Geraniaceae). The structures of the epoxy derivatives were deduced from their 1D- and 2D-NMR spectra, molecular modeling, and confirmed by synthesis starting from germacrone. The epoxy compounds were screened for their antimicrobial activities by a microdilution assay, which revealed high activities of both compounds against Bacillus subtilis (minimum inhibitory concentrations (M/Cs) determined were 4.3 and 43 nmol/ml for 1,10- and 4,5-epoxygermacrone, resp.) and Pseudomonas aeruginosa (0.043 and 0.855 µmol/ml for 1,10- and 4,5-epoxygermacrone, resp.). The discovery and observed activity of the two epoxides fills the gap in our knowledge of the active principles in this highly renowned ethnomedicinal plant species.


Asunto(s)
Antibacterianos/química , Antibacterianos/farmacología , Geranium/química , Sesquiterpenos de Germacrano/química , Bacillus subtilis/efectos de los fármacos , Técnicas de Química Sintética , Compuestos Epoxi/química , Compuestos Epoxi/farmacología , Geranium/metabolismo , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Aceites Volátiles/química , Plantas Medicinales/química , Pseudomonas aeruginosa/efectos de los fármacos , Sesquiterpenos de Germacrano/síntesis química , Sesquiterpenos de Germacrano/farmacología , Relación Estructura-Actividad
17.
Food Chem Toxicol ; 62: 554-65, 2013 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-24055768

RESUMEN

To determine the exact structure of previously tentatively identified minor essential-oil constituents of a Chamomile species (Antemis segetalis Ten. (Asteraceae)), we have synthesized a small combinatorial library of 54 regioisomeric allylmethoxyphenyl pentanoates and 2-pentenoates (49 completely new compounds). GC-MS in combination with 1D- and 2D-NMR analyses of the library compounds provided unambiguous data that led to a straightforward identification of the mentioned A. segetalis constituents as eugenyl angelate, 2-methylbutanoate and 3-methylbutanoate (0.21, 0.22, and 0.13 mg/100 g of fresh plant material, respectively). To assess the safety and potential beneficial pharmacological uses of these naturally occurring esters and several other library compounds (these were tested to provide relevant data for a SAR (structure-activity relationship) analysis), we have studied the effect of these compounds in several models of toxicity (acute toxicity against Artemia salina, cytotoxicity against two cell lines (fibroblast and melanoma)), as well as their acetylcholinesterase inhibitory and antibacterial activities. Anthemis segetalis constituents showed low to moderate activity in all tests. The obtained results suggest that the intake of these compounds in naturally available amounts, on their own, would probably not represent a risk to human health but the possible adverse interactions with the plant matrix should not be neglected.


Asunto(s)
Anthemis/química , Evaluación Preclínica de Medicamentos/métodos , Ésteres/toxicidad , Aceites Volátiles/química , Animales , Antibacterianos/química , Antibacterianos/farmacología , Artemia/efectos de los fármacos , Línea Celular Tumoral/efectos de los fármacos , Inhibidores de la Colinesterasa/química , Inhibidores de la Colinesterasa/farmacología , Técnicas Químicas Combinatorias/métodos , Ésteres/química , Ésteres/farmacocinética , Eugenol/análogos & derivados , Eugenol/química , Eugenol/toxicidad , Cromatografía de Gases y Espectrometría de Masas , Humanos , Espectroscopía de Resonancia Magnética , Melanoma/tratamiento farmacológico , Aceites Volátiles/análisis , Aceites Volátiles/toxicidad , Relación Estructura-Actividad , Pruebas de Toxicidad Aguda
18.
Pharm Biol ; 50(8): 933-40, 2012 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-22480199

RESUMEN

CONTEXT: Carlinae radix is an herbal drug, commonly used by the locals in southeastern Serbia for the treatment of respiratory and urogenital diseases and, externally, for various skin conditions. There still seems to be no detailed studies correlating the chemical composition of this drug and its ethnopharmacological uses. OBJECTIVE: Chemical composition, antimicrobial activity and mode of action of C. radix essential oil, isolated from commercial samples (confirmation of whose true biological identity was also the aim of this work) were analyzed. Antimicrobial potential of decoctions (extracts prepared by boiling plant material in a given solvent), used in ethnomedicine preferentially to the pure essential oil, was also investigated. MATERIALS AND METHODS: The essential oil obtained by hydrodistillation was screened for antimicrobial activity by disc diffusion and broth microdilution methods. Effects of the oil on the growth of Staphylococcus aureus cells were investigated using turbidimetric measurements and visualized using scanning electron microscopy. Analyses of the chemical composition of the oils were done using gas chromatography and gas chromatography/mass spectrometry. RESULTS AND DISCUSSION: Both the essential oil and the decocts exhibited a very high antimicrobial activity against all tested strains, with S. aureus as the most sensitive one [e.g., for the oil sample the values for minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) were 0.02, 0.04 µL/mL, respectively]. Growth curves of S. aureus demonstrated a significant decrease in turbidity (for the MIC concentration this amounted to ca. 70%) showing a concentration-dependent lysis of the cells, confirmed by scanning electron microscopy. Chemical composition, anatomical and morphological features of the sample pointed to Carlina acanthifolia L. (Asteraceae) instead of Carlina acaulis L. (Asteraceae). CONCLUSION: The results showed significant antimicrobial effect of the essential oil and the decoctions and support the use of this plant in ethnomedicine for the treatment of various human infections, especially those caused by S. aureus. Adulteration of the drug would not cause significant differences in its biological activity, since chemical composition of the sample showed high similarity with those containing C. acaulis roots.


Asunto(s)
Antibacterianos/química , Antibacterianos/farmacología , Asteraceae/química , Aceites Volátiles/química , Aceites Volátiles/farmacología , Raíces de Plantas/química , Staphylococcus aureus/efectos de los fármacos , Alquinos/análisis , Alquinos/farmacología , Antibacterianos/análisis , Antibacterianos/aislamiento & purificación , Antiinfecciosos/análisis , Antiinfecciosos/química , Antiinfecciosos/aislamiento & purificación , Antiinfecciosos/farmacología , Candida albicans/efectos de los fármacos , Candida albicans/crecimiento & desarrollo , Pared Celular/efectos de los fármacos , Pared Celular/ultraestructura , Etnofarmacología , Ionización de Llama , Furanos/análisis , Furanos/farmacología , Cromatografía de Gases y Espectrometría de Masas , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Gramnegativas/crecimiento & desarrollo , Pruebas de Sensibilidad Microbiana , Viabilidad Microbiana/efectos de los fármacos , Microscopía Electrónica de Rastreo , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Serbia , Solventes/química , Staphylococcus aureus/crecimiento & desarrollo , Staphylococcus aureus/ultraestructura
19.
Food Chem Toxicol ; 50(6): 2016-26, 2012 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-22449535

RESUMEN

Many plant species are used for medicinal purposes without the knowledge of their possible toxic effect. The ethnopharmacologically renowned genus Achillea L. (Asteraceae) is even more troublesome in this respect since different taxa are believed to have the same beneficial properties as A. millefolium. According to the median lethal i.p. dose (LD(50)=853 mg/kg, mice), the volatiles of Achillea umbellata Sibth. et Sm. are more toxic than the thujone-containing essential oils (LD(50)>960 mg/kg). A GC-MS analysis of A. umbellata oil revealed the presence of a series of fragranyl esters (six new natural products). The major constituents of this oil, the rare monoterpene alcohol fragranol and fragranyl acetate, and one more ester (benzoate), as well as the oil itself, showed antianxiety, analgesic and, in some instances, paralyzing properties at 50-150 mg/kg but these are very likely sign of intoxication and not of possible beneficial effects of the plant volatiles. Testing of antimicrobial activity demonstrated that the oil possesses moderate activity against pathogenic microorganisms, but the effect of the oil differs in pro- and eukaryotic cells. According to the results obtained, fragranol may be considered as the main active principle responsible for the observed activity/toxicity.


Asunto(s)
Achillea/química , Analgésicos , Ansiolíticos , Antibacterianos , Aceites Volátiles/farmacología , Achillea/toxicidad , Animales , Cromatografía Líquida de Alta Presión , Cromatografía en Capa Delgada , Cromatografía de Gases y Espectrometría de Masas , Hidrólisis , Dosificación Letal Mediana , Espectroscopía de Resonancia Magnética , Masculino , Espectrometría de Masas , Ratones , Ratones Endogámicos BALB C , Pruebas de Sensibilidad Microbiana , Aceites Volátiles/química , Aceites Volátiles/toxicidad , Dimensión del Dolor/efectos de los fármacos , Hojas de la Planta/química , Espectrofotometría Ultravioleta , Espectroscopía Infrarroja por Transformada de Fourier
20.
Nat Prod Commun ; 7(12): 1609-14, 2012 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-23413565

RESUMEN

In this study we evaluated in vitro (radical scavenging) and in vivo (hepatoprotective effect) antioxidant activities and antimicrobial properties of the extracts of the above- and underground parts of Geranium macrorrhizum L. (Geraniaceae), an ethnopharmacologically renowned plant species. The antioxidant activity and total phenol and flavonoid contents of four different solvent extracts were evaluated by seven different methods. The methanol extracts, administered i.p. to rats (120-480 mg/kg), were evaluated for hepatoprotective activity in a CCl4-induced hepatotoxicity model. The same extracts were tested for antimicrobial activity against seven bacterial and two fungal species. The administered methanol extracts with the highest antioxidant potential showed a significant dose-dependent hepatoprotective action against CCl4-induced liver damage in both decreasing the levels of liver transaminases and bilirubin and in reducing the extent of morphological malformations of the liver. The leaf methanol extract displayed a very strong antibacterial activity, especially against Staphylococcus aureus, with low minimal inhibitory and bactericidal concentrations. These results justify the frequent use of this plant species in folk medicine. Besides the known astringent effect, one can expect that the observed antimicrobial activity against several human pathogens contributes to the wound healing properties of this plant.


Asunto(s)
Antiinfecciosos/farmacología , Antioxidantes/farmacología , Enfermedad Hepática Inducida por Sustancias y Drogas/prevención & control , Geranium/química , Sustancias Protectoras/farmacología , Animales , Bilirrubina/metabolismo , Compuestos de Bifenilo/química , Intoxicación por Tetracloruro de Carbono/prevención & control , Relación Dosis-Respuesta a Droga , Compuestos Férricos , Flavonoides/química , Flavonoides/aislamiento & purificación , Depuradores de Radicales Libres/farmacología , Pruebas de Función Hepática , Masculino , Pruebas de Sensibilidad Microbiana , Fenoles/química , Fenoles/aislamiento & purificación , Picratos/química , Extractos Vegetales/química , Hojas de la Planta/química , Ratas , Ratas Wistar , Sustancias Reductoras/química , Sustancias Reductoras/farmacología , Rizoma/química , Staphylococcus aureus/efectos de los fármacos
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