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1.
J Agric Food Chem ; 68(10): 3220-3227, 2020 Mar 11.
Artigo em Inglês | MEDLINE | ID: mdl-32066240

RESUMO

Monoterpenes are aromatic compounds that are of great interest to wine as they are related to the quality of varietal wines. However, there is little information available about the impact of monoterpenes on wine odor perception at sub- or peri-threshold concentrations. The aim of this study was to investigate odor perception of monoterpene isomers in Pinot Gris wine and determine compositional matrix effects. Monoterpene isomers were quantitated in 46 Pinot Gris wines using headspace solid-phase microextraction-multidimensional gas chromatography-mass spectrometry, and sensory analysis was conducted using three different model wines. Results show that the nonvolatile composition of Pinot Gris wine strongly increased the volatility of monoterpene isomers. However, aromatic compounds suppressed odor perception, especially with the more complex monoterpene profiles. Monoterpenes were found to influence some fruity aromas in Pinot Gris. The knowledge of these interactions will further help in the development of wine styles and our understanding of wine quality.


Assuntos
Monoterpenos/química , Odorantes/análise , Percepção Olfatória , Vinho/análise , Adulto , Feminino , Aromatizantes/química , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Isomerismo , Masculino , Pessoa de Meia-Idade , Adulto Jovem
2.
Nat Commun ; 11(1): 508, 2020 01 24.
Artigo em Inglês | MEDLINE | ID: mdl-31980637

RESUMO

The bicyclo[3.3.1]nonane architecture is a privileged structural motif found in over 1000 natural products with relevance to neurodegenerative disease, bacterial and parasitic infection, and cancer among others. Despite disparate biosynthetic machinery, alkaloid, terpene, and polyketide-producing organisms have all evolved pathways to incorporate this carbocyclic ring system. Natural products of mixed polyketide/terpenoid origins (meroterpenes) are a particularly rich and important source of biologically active bicyclo[3.3.1]nonane-containing molecules. Herein we detail a fully synthetic strategy toward this broad family of targets based on an abiotic annulation/rearrangement strategy resulting in a 10-step total synthesis of garsubellin A, an enhancer of choline acetyltransferase and member of the large family of polycyclic polyprenylated acylphloroglucinols. This work solidifies a strategy for making multiple, diverse meroterpene chemotypes in a programmable assembly process involving a minimal number of chemical transformations.


Assuntos
Vias Biossintéticas , Monoterpenos/metabolismo , Monoterpenos/síntese química , Monoterpenos/química , Oxirredução , Estereoisomerismo , Terpenos/síntese química , Terpenos/química
3.
Chem Biodivers ; 17(2): e1900553, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31869516

RESUMO

The aroma emitted from the different organs of two Salvia verbenaca L. populations from Jordan were extracted by Solid Phase Micro-Extraction (SPME) and then analyzed by GC/MS. The emission profile of the stem, leaf and sepal samples from the Mediterranean zone (Al-Salt) was dominated by monoterpene hydrocarbons (68.0 %, 33.7 %, and 42.2 %, respectively). The emission profile of flowering parts including pre-flowering buds, fully expanded flowers and petals was dominated by oxygenated monoterpenes (58.6 %, 59.3 % and 87.1 %, respectively). The major constituent detected in these organs was trans-sabinene hydrate acetate (range 14.5 %-87.0 %). On the other hand, samples collected from Irano-Turanian zone showed different emission patterns. While the stems, leaves and petal emissions were dominated by sesquiterpene hydrocarbons (54.9 %, 76.8 % and 52.6 %, respectively), monoterpene hydrocarbons dominated the emission profiles of the pre-flowering buds (75.1 %) and fully expanded flowers (73.6 %). Petals emissions were characterized by high concentrations of oxygenated monoterpenes (58.8 %). Notably, trans-sabinene hydrate dominated most organs emissions except for leaves (range 20.0 %-58.8 %). Principle Component Analysis (PCA) and Cluster Analysis (CA) revealed two different clusters related to the two different geographical zones. The current investigation revealed two ecotypes of S. verbenaca that could result in two different chemotypes. Trans-sabinene hydrate acetate and trans-sabinene hydrate are suggested compounds for identifying these two chemotypes.


Assuntos
Salvia/química , Compostos Orgânicos Voláteis/química , Monoterpenos Bicíclicos/química , Monoterpenos Bicíclicos/isolamento & purificação , Análise por Conglomerados , Cromatografia Gasosa-Espectrometria de Massas , Jordânia , Monoterpenos/química , Monoterpenos/isolamento & purificação , Folhas de Planta/química , Folhas de Planta/metabolismo , Análise de Componente Principal , Salvia/metabolismo , Microextração em Fase Sólida , Compostos Orgânicos Voláteis/análise , Compostos Orgânicos Voláteis/isolamento & purificação
4.
Phytochemistry ; 170: 112216, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31841782

RESUMO

Hyperelodiones A-C, three undescribed monoterpenoid polyprenylated acylphloroglucinols possessing 6/6/6 fused tricyclic core, were isolated from Hypericum elodeoides Choisy. Their gross structures were elucidated by HRESIMS and NMR data. The absolute configurations of hyperelodiones A-C were assigned by their calculated and compared electronic circular dichroism (ECD) spectra combined with their common biosynthetic origin. A fluorescence quenching assay suggested that hyperelodiones A-C could bind to RXRα-LBD, whereas hyperelodione C showed the strongest interaction with a KD of 12.81 µΜ. In addition, hyperelodiones A-C dose-dependently inhibited RXRα transactivation and the growth of HeLa and MCF-7 cells. Among them, hyperelodione C showed the most potent inhibitory activities and dose-dependent PARP cleavage. Molecular docking results suggested that hyperelodione C showed a different interaction mode compared with hyperelodione A and hyperelodione B. Thus, hyperelodione C can be considered as a promising lead compound for cancer therapy, which can bind to RXRα-LBD and induce HeLa and MCF-7 cell apoptosis.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Apoptose/efeitos dos fármacos , Hypericum/química , Monoterpenos/farmacologia , Compostos Fitoquímicos/farmacologia , Receptor X Retinoide alfa/antagonistas & inibidores , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Células HeLa , Humanos , Células MCF-7 , Conformação Molecular , Simulação de Acoplamento Molecular , Monoterpenos/química , Monoterpenos/isolamento & purificação , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Receptor X Retinoide alfa/metabolismo , Relação Estrutura-Atividade , Células Tumorais Cultivadas
5.
Int J Mol Sci ; 21(1)2019 Dec 23.
Artigo em Inglês | MEDLINE | ID: mdl-31878088

RESUMO

Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is an important DNA repair enzyme in humans, and a current and promising inhibition target for the development of new chemosensitizing agents due to its ability to remove DNA damage caused by topoisomerase 1 (Top1) poisons such as topotecan and irinotecan. Herein, we report our work on the synthesis and characterization of new Tdp1 inhibitors that combine the arylcoumarin (neoflavonoid) and monoterpenoid moieties. Our results showed that they are potent Tdp1 inhibitors with IC50 values in the submicromolar range. In vivo experiments with mice revealed that compound 3ba (IC50 0.62 µM) induced a significant increase in the antitumor effect of topotecan on the Krebs-2 ascites tumor model. Our results further strengthen the argument that Tdp1 is a druggable target with the potential to be developed into a clinically-potent adjunct therapy in conjunction with Top1 poisons.


Assuntos
Carcinoma Krebs 2/tratamento farmacológico , Carcinoma Pulmonar de Lewis/tratamento farmacológico , Monoterpenos , Proteínas de Neoplasias , Inibidores de Fosfodiesterase , Diester Fosfórico Hidrolases/metabolismo , Animais , Carcinoma Krebs 2/enzimologia , Carcinoma Krebs 2/patologia , Carcinoma Pulmonar de Lewis/enzimologia , Carcinoma Pulmonar de Lewis/patologia , Feminino , Humanos , Células MCF-7 , Masculino , Camundongos , Monoterpenos/síntese química , Monoterpenos/química , Monoterpenos/farmacologia , Proteínas de Neoplasias/antagonistas & inibidores , Proteínas de Neoplasias/metabolismo , Inibidores de Fosfodiesterase/síntese química , Inibidores de Fosfodiesterase/química , Inibidores de Fosfodiesterase/farmacologia , Relação Estrutura-Atividade
6.
Chem Biodivers ; 16(12): e1900434, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31587473

RESUMO

Terpenes are a widespread group of secondary metabolites that can be found in various family plants such as the Lamiaceae. In view of their numerous valuable biological activities, the industrial production of concrete terpenes and essential oils rich in the substances is intensively studied. Monoterpenes constitute a significant part of the whole group of the aforementioned secondary metabolites. This is due to their numerous biological activities and their ability to permeate the skin. Despite the fact that these substances have gain popularity, they are not comprehensively characterized. The presented review is based on studies of the biological activities of the most important monoterpenes and the essential oils rich in these compounds. The authors focused attention on antioxidant activity, inhibition towards acetyl- and butyrylcholinesterase, and α-amylase and α-glucosidase, antifungal, hepatoprotective, sedative properties, and their skin permeation enhancement.


Assuntos
Monoterpenos/química , Doença de Alzheimer/tratamento farmacológico , Doença de Alzheimer/patologia , Animais , Antioxidantes/química , Colinesterases/química , Colinesterases/metabolismo , Lamiaceae/química , Lamiaceae/metabolismo , Monoterpenos/farmacologia , Monoterpenos/uso terapêutico , Fator 2 Relacionado a NF-E2/química , Fator 2 Relacionado a NF-E2/metabolismo , Óleos Voláteis/química , Estresse Oxidativo/efeitos dos fármacos
7.
Zhongguo Zhong Yao Za Zhi ; 44(17): 3684-3694, 2019 Sep.
Artigo em Chinês | MEDLINE | ID: mdl-31602940

RESUMO

Pistacia lentiscus,which belongs to foreign medicine resources,is widely distributed in the Mediterranean and Middle Eastern area. The essential oils are a mixture of several volatile compounds mainly monoterpenes and sesquiterpenes obtained from different parts of P. lentiscus by hydrodistillation. The variability of chemical composition,biological activities and content of essential oil is strongly affected by extraction technology,environmental and sex factors. It is indicated that essential oils of P. lentiscus have kinds of biological activities such as antibacterial,anticancer,anti-atherogenesis,antioxidant,anti-inflammatory and insecticidal activities.Many scholars hold the opinion that combination of different components with synergistic and/or additive actions should account for their biological activities. Due to its diverse efficacy and special taste,the essential oil of P. lentiscus has been extensively used in medicine,food and cosmetics industries. A mini review of chemical constituents and biological activities of essential oil of P. lentiscus in the past20 years is made here to provide valuable reference for the construction of " the Belt and Road".


Assuntos
Óleos Voláteis/química , Óleos Voláteis/farmacologia , Pistacia/química , Óleos Vegetais/química , Óleos Vegetais/farmacologia , Monoterpenos/química , Monoterpenos/farmacologia , Sesquiterpenos/química , Sesquiterpenos/farmacologia
8.
Mater Sci Eng C Mater Biol Appl ; 105: 110074, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31546393

RESUMO

Hydrogel membranes are often used as physical barriers in oral tissue reconstruction and facial surgery to isolate connective and epithelial tissues and form a closed space for undisturbed bone healing. In this study, gelatin and hyaluronic acid were crosslinked with genipin and loaded with a hinokitiol additive as a bacteriostatic agent for potential applications as regeneration membranes. This bifunctional membrane had biocompatibility and antibacterial activities on each membrane side for proper biodegradation. Different membrane groups of gelatin/hyaluronic acid were obtained via a solution casting technique and were genipin crosslinked. The membrane groups were further loaded with adequate hinokitiol at a loading concentration of up to 0.16 g/L (hinokitiol to phosphate buffered saline). Fourier transform infrared spectroscopy showed that gelatin and hyaluronic acid were crosslinked with genipin through cross-linking amide bond (CONH) formation with a cross-linking degree of over 84%. The groups with hinokitiol showed substantial antibacterial activity. Meanwhile, the addition of hinokitiol on hydrogel membranes did not significantly affect the tensile strength. However, it decreased the solubility of the membranes by slowing down the relaxation and degradation of their molecular junctions as hinokitiol is a hydrophobic compound with low permeability. Consequently, the degradation of hydrogel membranes with hinokitiol was delayed. In vitro cytocompatibility indicated that the cell viability of the groups with hinokitiol increased with incubation time, demonstrating that cell viability and proliferation were not affected by cell culture testing.


Assuntos
Antibacterianos , Hidrogéis , Teste de Materiais , Membranas Artificiais , Monoterpenos , Tropolona/análogos & derivados , Animais , Antibacterianos/química , Antibacterianos/farmacocinética , Antibacterianos/farmacologia , Reagentes para Ligações Cruzadas/química , Avaliação Pré-Clínica de Medicamentos , Gelatina/química , Ácido Hialurônico/química , Hidrogéis/química , Hidrogéis/farmacocinética , Hidrogéis/farmacologia , Iridoides/química , Camundongos , Monoterpenos/química , Monoterpenos/farmacocinética , Monoterpenos/farmacologia , Células NIH 3T3 , Tropolona/química , Tropolona/farmacocinética , Tropolona/farmacologia
9.
Molecules ; 24(17)2019 Aug 29.
Artigo em Inglês | MEDLINE | ID: mdl-31470602

RESUMO

The promising antimicrobial activity of essential oils (EOs) has led researchers to use them in combination with antimicrobial drugs in order to reduce drug toxicity, side effects, and resistance to single agents. Mentha x piperita, known worldwide as "Mentha of Pancalieri", is produced locally at Pancalieri (Turin, Italy). The EO from this Mentha species is considered as one of the best mint EOs in the world. In our research, we assessed the antifungal activity of "Mentha of Pancalieri" EO, either alone or in combination with azole drugs (fluconazole, itraconazole, ketoconazole) against a wide panel of yeast and dermatophyte clinical isolates. The EO was analyzed by GC-MS, and its antifungal properties were evaluated by minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) parameters, in accordance with the CLSI guidelines, with some modifications. The interaction of EO with azoles was evaluated through the chequerboard and isobologram methods. The results suggest that this EO exerts a fungicidal activity against yeasts and a fungistatic activity against dermatophytes. Interaction studies with azoles indicated mainly synergistic profiles between itraconazole and EO vs. Candida spp., Cryptococcus neoformans, and Trichophyton mentagrophytes. Thus, the "Mentha of Pancalieri" EO may act as a potential antifungal agent and could serve as a natural adjuvant for fungal infection treatment.


Assuntos
Antifúngicos/farmacologia , Azóis/farmacologia , Mentha piperita/química , Monoterpenos/farmacologia , Óleos Voláteis/química , Animais , Antifúngicos/química , Antifúngicos/isolamento & purificação , Arthrodermataceae/efeitos dos fármacos , Arthrodermataceae/crescimento & desenvolvimento , Arthrodermataceae/isolamento & purificação , Candida/efeitos dos fármacos , Candida/crescimento & desenvolvimento , Candida/isolamento & purificação , Cryptococcus/efeitos dos fármacos , Cryptococcus/crescimento & desenvolvimento , Cryptococcus/isolamento & purificação , Combinação de Medicamentos , Sinergismo Farmacológico , Fluconazol/farmacologia , Guias como Assunto , Humanos , Itraconazol/farmacologia , Cetoconazol/farmacologia , Testes de Sensibilidade Microbiana , Monoterpenos/química , Monoterpenos/isolamento & purificação , Óleos Voláteis/isolamento & purificação
10.
Molecules ; 24(18)2019 Sep 08.
Artigo em Inglês | MEDLINE | ID: mdl-31500359

RESUMO

Lavender oil is one of the most valuable aromatherapy oils, its anti-bacterial and anti-fungal activities can be explained by main components such as linalool, linalyl acetate, lavandulol, geraniol, or eucalyptol. The aim of the study was to assess the anti-microbial effects of two different lavender oils on a mixed microbiota from facial skin. The commercial lavender oil and essential lavender oil from the Crimean Peninsula, whose chemical composition and activity are yet to be published, were used. Both oils were analysed by gas chromatography coupled to mass spectrometry. The composition and properties of studied oils were significantly different. The commercial ETJA lavender oil contained 10% more linalool and linalyl acetate than the Crimean lavender oil. Both oils also had different effects on the mixed facial skin microbiota. The Gram-positive bacilli were more sensitive to ETJA lavender oil, and Gram-negative bacilli were more sensitive to Crimean lavender oil. However, neither of the tested oils inhibited the growth of Gram-positive cocci. The tested lavender oils decreased the cell number of the mixed microbiota from facial skin, but ETJA oil showed higher efficiency, probably because it contains higher concentrations of monoterpenoids and monoterpenes than Crimean lavender oil does.


Assuntos
Antibacterianos/farmacologia , Monoterpenos/farmacologia , Óleos Voláteis/farmacologia , Óleos Vegetais/farmacologia , Pele/microbiologia , /análise , Antibacterianos/química , Face , Cromatografia Gasosa-Espectrometria de Massas , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Humanos , Lavandula/química , Testes de Sensibilidade Microbiana , Monoterpenos/análise , Monoterpenos/química , Óleos Voláteis/química , Óleos Vegetais/química
11.
J Chem Ecol ; 45(9): 798-807, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31422515

RESUMO

The koala is a specialist feeder with a diet consisting almost exclusively of potentially toxic eucalypt leaves. Monoterpenes, an abundant class of plant secondary metabolites in eucalypts, are highly lipophilic. Chronic absorption and systemic exposure can be anticipated for the koala, causing health effects in various ways when consumed in high amounts, but particularly causing alterations in immune function in this species. Therefore, careful leaf selection, efficient detoxification pathways, and other specialist adaptations are required to protect animals from acute intoxication. This is the first paper providing insight into the systemic exposure of koalas to these compounds. Profiles of six selected major monoterpenes were investigated in the ingesta of deceased koalas from four different regions of NSW and South-East Queensland. Concentrations of the same compounds were measured in lymphoid tissues of deceased koalas and in the blood of live koalas from other regions of NSW. Analytical methods included liquid extraction and solid-phase micro-extraction, followed by gas-chromatography/ mass-spectrometry. Concentrations in the ingesta of individual animals vary remarkably, though the average proportions of individual monoterpenes in the ingesta of animals from the four different regions are highly comparable. Blood concentrations of the selected monoterpenes also varied considerably. The highest blood concentrations were found for 1,8-cineole, up to 971 ng/ml. There was similarity between circulating monoterpene profiles and ingesta profiles. Based on the observed lack of similarity between blood and lymph tissue concentrations, individual monoterpenes either exhibit different affinities for lymphatic tissue compared to blood or their accumulation in blood and lymph tissue differs temporally. In general, blood monoterpene concentrations found in koalas were low compared to those reported in other marsupial eucalypt feeders, but significant concentrations of monoterpenes were detected in all samples analysed. This data on blood and lymphatic tissue monoterpene concentrations builds the fundamental groundwork for future research into the effects of dietary monoterpenes on various biological processes of specialist herbivores and into the significance of these animals' metabolic and behavioural strategies for coping with these compounds. We have shown that the systemic exposure of koalas to potentially anti-inflammatory eucalypt monoterpenes is continuous, and we provide data on physiological concentrations which will allow realistic future studies of the effects of monoterpenes on immune cell function.


Assuntos
Eucalyptus/química , Monoterpenos/química , Phascolarctidae/metabolismo , Folhas de Planta/química , Animais , Austrália , Comportamento Alimentar , Monoterpenos/metabolismo , Phascolarctidae/fisiologia
12.
J Chem Ecol ; 45(8): 657-666, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31407199

RESUMO

The box tree moth, Cydalima perspectalis, is an invasive pest in Europe causing damage on Buxus species. In this study, we aimed to develop a "bisexual" lure to attract both female and male moths. Based on a previous screening bioassay we tested methyl salicylate, phenylacetaldehyde and eugenol as potential attractants in different combinations. The trapping results showed that both binary and ternary blends attracted male and female moths. Catches with these blends were comparable to catches with the synthetic pheromone. Subsequently we carried out single sensillum recordings, which proved the peripheral detection of the above-mentioned compounds on male and female antennae. To identify synergistic flower volatiles, which can be also attractive and can increase the trap capture, we collected flower headspace volatiles from 12 different flowering plant species. Several components of the floral scents evoked good responses from antennae of both females and males in gas chromatography-electroantennographic detection. The most active components were tentatively identified by gas chromatography coupled mass spectrometry as benzaldehyde, cis-ß-ocimene, (±)-linalool and phenethyl alcohol. These selected compounds in combination did not increase significantly the trap capture compared to the methyl salicylate- phenyacetaldehyde blend. Based on these results we discovered the first attractive blend, which was able to attract both adult male and female C. perspectalis in field conditions. These results will yield a good basis for the optimization and development of a practically usable bisexual lure against this invasive pest.


Assuntos
Comportamento Animal/efeitos dos fármacos , Mariposas/fisiologia , Feromônios/farmacologia , Animais , Eugenol/química , Eugenol/farmacologia , Feminino , Flores/química , Flores/metabolismo , Cromatografia Gasosa-Espectrometria de Massas , Controle de Insetos , Masculino , Monoterpenos/química , Monoterpenos/farmacologia , Feromônios/análise , Robinia/química , Robinia/metabolismo , Rosa/química , Rosa/metabolismo , Compostos Orgânicos Voláteis/química , Compostos Orgânicos Voláteis/farmacologia
13.
Pestic Biochem Physiol ; 158: 185-200, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31378356

RESUMO

The present work describes the antimicrobial action of 25 monoterpenes (six hydrocarbons, five ketones, two aldehydes, six alcohols and six acetate analogues) against Gram-negative Escherichia coli and Gram-positive Staphylococcus aureus and antifungal activity against Aspergillus flavus. The antibacterial activity was evaluated by broth microdilution technique as a minimum inhibitory concentration (MIC) and the antifungal activity was performed by mycelia radial growth technique as the effective concentration causing 50% inhibition of the mycelial growth (EC50). The results showed that thymol and α-terpineol were the most potent against E. coli (MIC = 45 and 55 mg/L, respectively) and S. aureus (MIC = 135 and 225 mg/L, respectively). The results also showed that thymol displayed the maximum antifungal action against A. flavus with EC50 20 mg/L. Furthermore, the antioxidant activity was determined using N,N-dimethyl-1,4-phenylenediamine (DMPD) and the results showed that geraniol were the most potent compound (IC50 = 19 mg/L). Molecular docking studies indicated that the compounds displayed different binding interactions with the amino acid residues at the catalytic sites of N5-carboxyaminoimidazole synthetase and oxysterol binding protein Osh4 enzymes. Non-covalent interactions including van der Waals, hydrogen bonding as well as hydrophobic were observed between the compounds and the enzymes. A significant relationship was found between the docking score and the biological activity of the tested monoterpenes compared to the ceftriaxone and carbendazim as standard bactericide and fungicide, respectively. In silico ADMET properties were also performed and displayed potential for the development of promising antimicrobial agents. For these reasons, these compounds may be considered as potential ecofriendly alternatives in food preservation to delay or prevent the microbial infection and prolong the shelf life of food products.


Assuntos
Anti-Infecciosos/farmacologia , Antioxidantes/farmacologia , Monoterpenos/metabolismo , Antibacterianos/química , Antibacterianos/farmacologia , Anti-Infecciosos/química , Cicloexenos/química , Cicloexenos/farmacologia , Escherichia coli/efeitos dos fármacos , Hidrocarbonetos/química , Hidrocarbonetos/farmacologia , Testes de Sensibilidade Microbiana , Monoterpenos/química , Monoterpenos/farmacologia , Staphylococcus aureus/efeitos dos fármacos
14.
J Appl Microbiol ; 127(4): 1048-1056, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31328837

RESUMO

AIM: The molecular typing and the susceptibility of Staphylococcus aureus strains of swine origin to antibiotics, oregano (Origanum vulgare L.) essential oil (EO) and Chilean blackberry maqui (Aristotelia chilensis (Molina) Stuntz) extract were determined. METHODS AND RESULTS: Twenty S. aureus strains of swine origin were subjected to molecular typing, of which six strains were selected for antimicrobial susceptibility testing. The epsilon test (Etest) was used to determine the antibiotic susceptibility. The susceptibility to natural antimicrobials (NAs): oregano EO, maqui extract, thymol (Thy) and carvacrol (Carv), was carried out using the disk diffusion method. The S. aureus strains were genetically diverse. All strains were resistant to at least one class of antibiotic, and two strains were multidrug-resistant. The minimum inhibitory concentration of oregano EO, Thy and Carv was 0·01-0·04%. Maqui extract did not show antistaphylococcal activity. CONCLUSIONS: Natural antimicrobials extracted from oregano have an inhibitory activity against S. aureus strains from swine origin, with no effect using maqui extract. SIGNIFICANCE AND IMPACT OF THE STUDY: This study provides information about the characteristics of S. aureus strains of swine origin, and about the potential use of NAs from oregano to enhance the control of antibiotic-resistant S. aureus strains in the pork supply chain.


Assuntos
Antibacterianos/farmacologia , Farmacorresistência Bacteriana/efeitos dos fármacos , Magnoliopsida/química , Óleos Voláteis/farmacologia , Extratos Vegetais/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Suínos/microbiologia , Animais , Testes de Sensibilidade Microbiana , Tipagem Molecular , Monoterpenos/química , Origanum/química , Staphylococcus aureus/classificação , Staphylococcus aureus/genética , Timol/química
15.
Chem Pharm Bull (Tokyo) ; 67(7): 675-689, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31257323

RESUMO

An Orobanchaceae plant Cistanche tubulosa (SCHENK) WIGHT (Kanka-nikujuyou in Japanese), which is one of the authorized plant resources as Cistanches Herba in both Japanese and Chinese Pharmacopoeias, is a perennial parasitic plant growing on roots of sand-fixing plants. The stems of C. tubulosa have traditionally been used for treatment of impotence, sterility, lumbago, and body weakness as well as a promoting agent of blood circulation. In recent years, Cistanches Herba has also been widely used as a health food supplement in Japan, China, and Southeast Asian countries. Here we review our recent studies on chemical constituents from the stems of C. tubulosa as well as their bioactivities such as vasorelaxtant, hepatoprotective, and glucose tolerance improving effects.


Assuntos
Produtos Biológicos/química , Cistanche/química , Animais , Aorta Torácica/efeitos dos fármacos , Aorta Torácica/metabolismo , Produtos Biológicos/isolamento & purificação , Produtos Biológicos/farmacologia , Cistanche/metabolismo , Glicosídeos/química , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Macrófagos/citologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Monoterpenos/química , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Caules de Planta/química , Caules de Planta/metabolismo , Substâncias Protetoras/química , Substâncias Protetoras/isolamento & purificação , Substâncias Protetoras/farmacologia , Vasodilatadores/química , Vasodilatadores/isolamento & purificação , Vasodilatadores/farmacologia
16.
Artigo em Inglês | MEDLINE | ID: mdl-31294650

RESUMO

The present study examines the influence of the natural preservatives carvacrol, eugenol, trans-cinnamaldehyde and the essential oil (EO) Origanum vulgare on ochratoxin A (OTA) production and the mycelial growth of two food-related moulds, Penicillium verrucosum and Aspergillus westerdijkiae, by broth macro-dilution assay for 21 days. With the addition of ½ minimum inhibitory concentration (MIC) carvacrol, eugenol and O. vulgare EO, the mycelial dry weight of both moulds decreased significantly over the whole incubation period of 7, 14 and 21 days. Trans-cinnamaldehyde slightly stimulated the growth of A. westerdijkiae and P. verrucosum at 14 and 21 days of incubation. Growth inhibition did not accompany inhibition of OTA production. Although the growth of both moulds was inhibited after the addition of ½ MIC carvacrol, eugenol and O. vulgare EO, the OTA production of the strong mycotoxin producer A. westerdijkiae was stimulated. Only trans-cinnamaldehyde inhibited the production of OTA with the addition of ½ MIC. P. verrucosum produced significantly less OTA than A. westerdijkiae, and its mycotoxin production was almost completely inhibited by the addition of ½ MIC of the natural preservatives.


Assuntos
Aspergillus/efeitos dos fármacos , Microbiologia de Alimentos , Conservantes de Alimentos/farmacologia , Micélio/efeitos dos fármacos , Ocratoxinas/biossíntese , Penicillium/efeitos dos fármacos , Acroleína/análogos & derivados , Acroleína/química , Acroleína/farmacologia , Aspergillus/química , Eugenol/química , Eugenol/farmacologia , Conservantes de Alimentos/química , Monoterpenos/química , Monoterpenos/farmacologia , Micélio/crescimento & desenvolvimento , Ocratoxinas/química , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Penicillium/química
17.
Artigo em Inglês | MEDLINE | ID: mdl-31269467

RESUMO

Xiaoxuming decoction (XXMD) is a key Chinese medicine prescription, which has been clinically used for stroke treatment for thousands of years in ancient China. The extracted active fraction of XXMD (AF-XXMD) contains almost pharmacological active components with anti-cerebral ischemic effects. However, the illumination of its complex ingredients remains challenging. In this study, ultra-performance liquid chromatography coupled with time-of-flight mass spectrometry (UPLC/Q-TOF MS) and rapid resolution liquid chromatography-triple quad linear ion trap mass spectrometry (RRLC-QTRAP MSn) methods were developed for the qualitative and quantitative analysis of AF-XXMD, respectively. Data showed that 48 compounds were identified in AF-XXMD by using UPLC-Q-TOF/MS, including 14 alkaloids, 14 flavonoids, 12 triterpenoids, 3 chromones, 3 monoterpenes, 1 cyanide glycoside, and 1 volatile oil. Among them, 38 components were unambiguously characterized by their reference standards. A total of 15 compounds in AF-XXMD were first reported. Additionally, 33 compounds were quantified by using RRLC-QTRAP MSn in AF-XXMD. This developed RRLC-QTRAP MSn method provides an adequate linearity (r2 > 0.99) and intrabatch and interbatch variations (RSD < 15%), with recovery (60.3%-107.5%) of 33 compounds concerned. The total content of 33 compounds in AF-XXMD reached 31.53%. The high total contents of compounds of Xing Ren, Shao Yao, and Huang Qin in AF-XXMD were 9.52%, 8.85%, and 7.62%, respectively. The data further showed that cyanophoric glycosides, monoterpenes, and flavonoids were the three most abundant components in AF-XXMD. Results provide advantageous information for the comprehensive study of the pharmacokinetic features and pharmacological mechanisms of AF-XXMD.


Assuntos
Isquemia Encefálica/tratamento farmacológico , Cromatografia Líquida de Alta Pressão/métodos , Medicamentos de Ervas Chinesas/química , Acidente Vascular Cerebral/tratamento farmacológico , Espectrometria de Massas em Tandem/métodos , Alcaloides/química , Alcaloides/farmacocinética , China , Medicamentos de Ervas Chinesas/farmacocinética , Flavonoides/química , Flavonoides/farmacocinética , Glicosídeos/química , Glicosídeos/farmacocinética , Humanos , Medicina Tradicional Chinesa , Monoterpenos/química , Monoterpenos/farmacocinética , Plantas Medicinais/química
18.
Food Chem ; 298: 125079, 2019 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-31260959

RESUMO

Citral-in-water emulsions were prepared with two different essential oil concentrations of 2.5 and 5.0% (w/w), then spray-dried in the presence of the same amount of maltodextrins (20%). The microcapsules were prepared with two different emulsifier compositions: monolayer microcapsules (ML) stabilized by sodium caseinate alone and layer-by-layer microcapsules (LBL) stabilized by sodium caseinate and pectin. The encapsulation efficiency was higher for LBL microcapsules (e.g. 99.6 ±â€¯0.4% for 2.5% citral) than that for ML ones (e.g. 78.6 ±â€¯0.6% for 2.5% citral) which confirm that the additional pectin layer was able to protect citral during the spray-drying process whatever citral concentration. Furthermore, our results showed that the antibacterial activity of the obtained microcapsules significantly depends on both citral concentration and interfacial membrane composition. The presence of two layers surrounding the citral droplets may result in a progressive and controlled release of the encapsulated citral.


Assuntos
Emulsões/química , Monoterpenos/química , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Cápsulas/química , Caseínas/química , Dessecação , Listeria/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Óleos Voláteis/química , Tamanho da Partícula , Pectinas/química , Polissacarídeos/química , Staphylococcus aureus/efeitos dos fármacos
19.
Phytochemistry ; 164: 236-242, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31185420

RESUMO

Mangiterpenes A-C and 2',3'-seco-manginoid C, four undescribed sesquiterpene/monoterpene-shikimate-conjugated meroterpenoids with spiro ring systems, were isolated from Guignardia mangiferae. The structures and absolute configurations of these compounds were established by comprehensive spectroscopic analyses and electronic circular dichroism (ECD) calculations. Mangiterpenes A-C represent the first examples of sesquiterpene-shikimate-conjugated spirocyclic meroterpenoids, and 2',3'-seco-manginoid C features an unexpected 2',3'-seco-manginoids skeleton. Mangiterpene C strongly inhibited the production of NO inducted by LPS, with an IC50 value of 5.97 µM. It showed an anti-inflammatory effect by means of blocking in the NF-κB signaling pathway and decreasing the expression of inflammatory mediators.


Assuntos
Anti-Inflamatórios não Esteroides/farmacologia , Monoterpenos/farmacologia , Ácido Chiquímico/farmacologia , Compostos de Espiro/farmacologia , Terpenos/farmacologia , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/isolamento & purificação , Relação Dose-Resposta a Droga , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Camundongos , Estrutura Molecular , Monoterpenos/química , Monoterpenos/isolamento & purificação , NF-kappa B/antagonistas & inibidores , NF-kappa B/metabolismo , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Células RAW 264.7 , Ácido Chiquímico/química , Ácido Chiquímico/isolamento & purificação , Transdução de Sinais/efeitos dos fármacos , Compostos de Espiro/química , Compostos de Espiro/isolamento & purificação , Relação Estrutura-Atividade , Terpenos/química , Terpenos/isolamento & purificação
20.
Eur J Med Chem ; 178: 515-529, 2019 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-31207463

RESUMO

Carvacrol (CAR), a natural monoterpene particularly abundant in plants belonging to the Lamiaceae family, has recently attracted much attention for its many biological properties (antioxidant, anti-inflammatory, neuroprotective, antitumour, antibacterial, and several others). However, CAR has poor chemical-physical properties (low water solubility and high volatility), which hamper its potential pharmacological uses. In this paper, the synthesis and antimicrobial evaluation of 23 carvacrol derivatives (WSCP1-23) against a panel of selected gram-positive and gram-negative bacteria are reported. Using the prodrug approach, CAR hydrophilic (WSCP1-17) and lipophilic prodrugs (WSCP18-23) were prepared. Notably, CAR water solubility was increased by using polar neutral groups (such as natural amino acids) with the aim of improving oral drug delivery. On the other hand, CAR lipophilic prodrugs, obtained by prenylation of CAR hydroxyl group, were designed to promote membrane permeation and oral absorption. Our results revealed that WSCP1-3, showing the highest water solubility (>1700-fold compared to that of CAR), possessed good antibacterial activity against gram-negative bacteria with MIC values comparable to those of CAR and antifungal properties against different species of Candida. WSCP18-19 were the most promising prodrugs, showing good antibacterial profiles against gram-positive bacteria by interfering with the biofilm formation of Staphylococcus aureus and Staphylococcus epidermidis. Moreover, WSCP18-19 resulted more stable in simulated fluids and human plasma than WSCP1-3. Toxicity studies performed on human erythrocytes and HaCaT cells revealed that all WSCPs were not toxic at the tested concentrations.


Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Monoterpenos/farmacologia , Pró-Fármacos/farmacologia , Antibacterianos/síntese química , Antibacterianos/química , Antifúngicos/síntese química , Antifúngicos/química , Candida/efeitos dos fármacos , Relação Dose-Resposta a Droga , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Monoterpenos/síntese química , Monoterpenos/química , Pró-Fármacos/síntese química , Pró-Fármacos/química , Solubilidade , Relação Estrutura-Atividade
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