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1.
Zhongguo Zhong Yao Za Zhi ; 45(18): 4411-4415, 2020 Sep.
Artigo em Chinês | MEDLINE | ID: mdl-33164370

RESUMO

Eight terpenoids(1-8) were isolated from the ethyl acetate soluble fraction of 80% ethanol extract of leaf of Toona sinensis through various column chromatographies on silica gel, Sephadex LH-20, MCI and ODS. Their structures were elucidated as 8ß-hydroxypimar-15-en-19-oic acid methyl ester(1), cedrodorol B(2), 11ß-acetoxyobacunol(3), toonayunnanin D(4), toonaciliatone D(5), toonaciliatone A(6), cedrelone(7), and 11ß-hydroxygedunin(8) based on their chemical and physicochemical methods and spectroscopic data. Compound 1 was a new pimaradienediterpenoid and terpenoid 2-7 were isolated and identified from this plant for the first time. Compound 1 was tested in vitro for cytotoxic potential by employing MTT method and radical scavenging potential using DPPH test. As a result, 1 exhibited weak cytotoxic activity against three tested tumor cell lines(SMMC-7721, A549 and MCF-7) with IC_(50) values less than 40 µmol·L~(-1) and moderate radical scavenging activities with IC_(50) values of 74.3 µmol·L~(-1).


Assuntos
Extratos Vegetais , Terpenos , Linhagem Celular Tumoral , Folhas de Planta , Terpenos/farmacologia
2.
Ecotoxicol Environ Saf ; 205: 111159, 2020 Dec 01.
Artigo em Inglês | MEDLINE | ID: mdl-32829212

RESUMO

Cyanobacteria blooms are crucial environmental issues by threatening both aquatic ecosystem and human health. A biomass by-product with antimicrobial activity, pyroligneous acid (PA) was tested for its suitability for removal of the cyanobacteria Microcystis aeruginosa (M. aeruginosa) in this work. Results show that the removal efficiency could reach up to 90% in the presence of 0.45% of PA and the inhibition to M. aeruginosa growth could extend to at least 40 days. The removal mechanism was studied. Both organic acids and phenols are functional content in M. aeruginosa removal and acetic acid is the most important one. Zeta potential analysis and morphology study show that the damage of cells dominates the flocculation and sedimentation of M. aeruginosa under low PA concentration (<0.7%), and increasing PA (≥0.7%) resulted in a trend of zeta potential to zero, thus removing any "shield" and triggering flocculation. Finally, study on the phenols residual after M. aeruginosa treatment shows that it could be close to 0 in 70 h. Therefore, this work proposes a possible method for world-wide treatment of cyanobacteria bloom and a new way for further utilization of PA.


Assuntos
Anti-Infecciosos/farmacologia , Eutrofização/efeitos dos fármacos , Microcystis/efeitos dos fármacos , Terpenos/farmacologia , Biomassa , Ecossistema , Floculação , Humanos , Microcystis/crescimento & desenvolvimento , Compostos Orgânicos
3.
Braz Oral Res ; 34: e050, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32578760

RESUMO

Candida infection is an important cause of morbidity and mortality in immunocompromised patients. The increase in its incidence has been associated with resistance to antimicrobial therapy and biofilm formation. The aim of this study was to evaluate the efficacy of tea tree oil (TTO) and its main component - terpinen-4-ol - against resistant Candida albicans strains (genotypes A and B) identified by molecular typing and against C. albicans ATCC 90028 and SC 5314 reference strains in planktonic and biofilm cultures. The minimum inhibitory concentration, minimum fungicidal concentration, and rate of biofilm development were used to evaluate antifungal activity. Results were obtained from analysis of the biofilm using the cell proliferation assay 2,3-Bis-(2-methoxy-4-nitro-5-sulfophenyl)-2H-tetrazolium-5-carboxanilide (XTT) and confocal laser scanning microscopy (CLSM). Terpinen-4-ol and TTO inhibited C. albicans growth. CLSM confirmed that 17.92 mg/mL of TTO and 8.86 mg/mL of terpinen-4-ol applied for 60 s (rinse simulation) interfered with biofilm formation. Hence, this in vitro study revealed that natural substances such as TTO and terpinen-4-ol present promising results for the treatment of oral candidiasis.


Assuntos
Biofilmes/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Óleo de Melaleuca/farmacologia , Terpenos/farmacologia , Resinas Acrílicas , Análise de Variância , Antifúngicos/farmacologia , Biofilmes/crescimento & desenvolvimento , Candida albicans/crescimento & desenvolvimento , Bases de Dentadura/microbiologia , Testes de Sensibilidade Microbiana , Microscopia Confocal , Valores de Referência , Reprodutibilidade dos Testes , Estatísticas não Paramétricas , Óleo de Melaleuca/química , Terpenos/química
4.
Environ Toxicol ; 35(10): 1058-1069, 2020 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-32485087

RESUMO

Glioblastoma is the most common primary brain tumor with poor survival rate and without effective treatment strategy. Notably, amplification and active mutation of epidermal growth factor receptor (EGFR) occur frequently in glioblastoma patient that may be a potential treatment target. Several studies indicated that various type of herbal compounds not only regulate anti-depressant effect but also shown capacity to suppress glioblastoma growth via inducing apoptosis and inhibiting oncogene signaling transduction. Hyperforin, an herb compound derived from St. John's wort was used to treat depressive disorder by inhibiting neuronal reuptake of several neurotransmitters. Although hyperforin can reduce matrix metallopeptidases-2 (MMPs) and -9-mediated metastasis of glioblastoma, the detail mechanism of hyperforin on glioblastoma is remaining unclear. Here, we suggested that hyperforin may induce extrinsic/intrinsic apoptosis and suppress anti-apoptotic related proteins expression of glioblastoma. We also indicated that hyperforin-mediated anti-apoptotic potential of glioblastoma was correlated to inactivation of EGFR/extracellular signal-regulated kinases (ERK)/nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) signaling.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Apoptose/efeitos dos fármacos , MAP Quinases Reguladas por Sinal Extracelular/metabolismo , Floroglucinol/análogos & derivados , Terpenos/farmacologia , Fator de Transcrição RelA/metabolismo , Antineoplásicos Fitogênicos/isolamento & purificação , Proteínas Reguladoras de Apoptose/metabolismo , Neoplasias Encefálicas/metabolismo , Neoplasias Encefálicas/patologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Receptores ErbB/metabolismo , Glioblastoma/metabolismo , Glioblastoma/patologia , Humanos , Hypericum/química , Floroglucinol/isolamento & purificação , Floroglucinol/farmacologia , Transdução de Sinais , Terpenos/isolamento & purificação , Fator de Transcrição RelA/genética
5.
J Insect Sci ; 20(3)2020 May 01.
Artigo em Inglês | MEDLINE | ID: mdl-32556318

RESUMO

The insect immune system includes several mechanisms responsible for defending against pathogens, parasites, and parasitoids. Some botanical insecticides, such as Azadirachta indica oil, cause changes in the immune system of various insect species. Spodoptera frugiperda is an important agricultural pest; thus, knowledge about the effect of neem oil on the immune system of this species can assist in its management. This study aimed to evaluate the effect of A. indica oil on the immune system of S. frugiperda. Caterpillars (2-3 mg) were placed individually in containers (50 ml) with approximately 10 g of diet, containing 125, 250, and 500 ppm of neem oil with propanone; the control group received only the propanone diet. In four experiments, the total number of hemocytes, the phagocytic activity, the activity of lysozyme-like enzymes, and phenoloxidase activity were measured in caterpillars at the end of the sixth instar. The total number of hemocytes in insects exposed to neem oil was 21% lower than in the control group. The percentage of cells that phagocyted the latex beads was similar among the caterpillars that ingested the different concentrations. The mean diameter of cell lysis halos was reduced only at concentrations of 125 and 250 ppm. Absorbance did not differ between treatments. Knowing that this oil reduces the number of circulation cells and the activity of lysozyme-like enzymes is of great importance to design control strategies, once the neem oil could be added to other biological agents for mortality reducing the chances of this insect surviving in the environment.


Assuntos
Azadirachta/química , Glicerídeos/farmacologia , Inseticidas/farmacologia , Larva/efeitos dos fármacos , Spodoptera/efeitos dos fármacos , Terpenos/farmacologia , Animais , Sistema Imunitário/efeitos dos fármacos , Larva/imunologia , Spodoptera/imunologia
6.
PLoS One ; 15(5): e0231948, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32369483

RESUMO

In our search for bioactive mushrooms native to British Columbia, we determined that the ethanol extracts from fruiting bodies of the terrestrial polypore Albatrellus flettii had potent anti-cell viability activity. Using bioassay-guided fractionation, mass spectrometry and nuclear magnetic resonance, we successfully isolated three known compounds (grifolin, neogrifolin and confluentin). These compounds represent the major anti-cell viability components from the ethanol extracts of A. flettii. We also identified a novel biological activity for these compounds, specifically in down-regulating KRAS expression in two human colon cancer cell lines. Relatively little is known about the anti-cell viability activity and mechanism of action of confluentin. For the first time, we show the ability of confluentin to induce apoptosis and arrest the cell cycle at the G2/M phase in SW480 human colon cancer cells. The oncogenic insulin-like growth factor 2 mRNA-binding protein 1 (IMP1) has been previously shown to regulate KRAS mRNA expression in colon cancer cells, possibly through its ability to bind to the KRAS transcript. Using a fluorescence polarization assay, we show that confluentin dose-dependently inhibits the physical interaction between KRAS RNA and full-length IMP1. The inhibition also occurs with truncated IMP1 containing the KH1 to KH4 domain (KH1to4 IMP1), but not with the di-domain KH3 and KH4 (KH3&4 IMP1). In addition, unlike the control antibiotic neomycin, grifolin, neogrifolin and confluentin do not bind to KRAS RNA. These results suggest that confluentin inhibits IMP1-KRAS RNA interaction by binding to the KH1&2 di-domains of IMP1. Since the molecular interaction between IMP1 and its target RNAs is a pre-requisite for the oncogenic function of IMP1, confluentin should be further explored as a potential inhibitor of IMP1 in vivo.


Assuntos
Basidiomycota/química , Neoplasias do Colo/genética , Fenóis/farmacologia , Proteínas Proto-Oncogênicas p21(ras)/genética , Resorcinóis/farmacologia , Ciclo Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Neoplasias do Colo/tratamento farmacológico , Neoplasias do Colo/metabolismo , Relação Dose-Resposta a Droga , Regulação para Baixo , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Células HT29 , Humanos , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Proteínas de Ligação a RNA/genética , Proteínas de Ligação a RNA/metabolismo , Terpenos/farmacologia
7.
Malar J ; 19(1): 127, 2020 Mar 30.
Artigo em Inglês | MEDLINE | ID: mdl-32228701

RESUMO

BACKGROUND: The species-specific mode of action for DEET and many other mosquito repellents is often unclear. Confusion may arise for many reasons. First, the response of a single mosquito species is often used to represent all mosquito species. Second, behavioural studies usually test the effect of repellents on mosquito attraction towards human odorants, rather than their direct repulsive effect on mosquitoes. Third, the mosquito sensory neuron responses towards repellents are often not directly examined. METHODS: A close proximity response assay was used to test the direct repulsive effect of six mosquito repellents on Anopheles coluzzii, Aedes aegypti and Culex quinquefasciatus mosquitoes. Additionally, the behavioural assay and calcium imaging recordings of antennae were used to test the response of An. coluzzii mosquitoes towards two human odorants (1-octen-3-ol and benzaldehyde) at different concentrations, and mixtures of the repellents lemongrass oil and p-menthane-3,8-diol (PMD) with DEET. RESULTS: Anopheles coluzzii mosquitoes were repelled by lemongrass oil and PMD, while Ae. aegypti and Cx. quinquefasciatus mosquitoes were repelled by lemongrass oil, PMD, eugenol, and DEET. In addition, high concentrations of 1-octen-3-ol and benzaldehyde were repellent, and activated more olfactory receptor neurons on the An. coluzzii antennae than lower concentrations. Finally, changes in olfactory responses to repellent mixtures reflected changes in repulsive behaviours. CONCLUSIONS: The findings described here suggest that different species of mosquitoes have different behavioural responses to repellents. The data further suggest that high-odour concentrations may recruit repellent-sensing neurons, or generally excite many olfactory neurons, yielding repellent behavioural responses. Finally, DEET can decrease the neuronal and behavioural response of An. coluzzii mosquitoes towards PMD but not towards lemongrass oil. Overall, these studies can help inform mosquito repellent choice by species, guide decisions on effective repellent blends, and could ultimately identify the olfactory neurons and receptors in mosquitoes that mediate repellency.


Assuntos
Aedes/efeitos dos fármacos , Anopheles/efeitos dos fármacos , Culex/efeitos dos fármacos , Repelentes de Insetos/farmacologia , Percepção Olfatória , Aedes/fisiologia , Animais , Anopheles/fisiologia , Aprendizagem da Esquiva , Benzaldeídos , Culex/fisiologia , DEET/farmacologia , Relação Dose-Resposta a Droga , Eugenol/farmacologia , Feminino , Octanóis , Odorantes , Óleos Vegetais/farmacologia , Especificidade da Espécie , Terpenos/farmacologia
8.
PLoS Negl Trop Dis ; 14(4): e0008225, 2020 04.
Artigo em Inglês | MEDLINE | ID: mdl-32251453

RESUMO

BACKGROUND: Essential oils may represent an alternative strategy for controlling scabies, a neglected tropical disease caused by the infestation of mite from the species Sarcoptes scabiei. Lemongrass (Cymbopogen citratus) oil is reported to possess pharmacological properties including antiparasitc, antioxidant, antimicrobial and anti-inflammatory. The aim of the present study was to assess the potential efficacy of lemongrass oil against the mites and eggs of Sarcoptes scabiei. METHODOLOGY/PRINCIPAL FINDINGS: Mass spectrometry analysis confirmed that the main component presented in lemongrass oil was citral. Lemongrass oil at concentrations of 10% and 5% killed all Sarcoptes mites within 10 and 25 min, respectively. The median lethal concentration value was 1.37%, 1.08%, 0.91%, 0.64%, and 0.48% at 1, 3, 6, 12, and 24 h, respectively. Lemongrass oil at all concentrations (10%, 5%, 1%, 0.5%, 0.1%) was able to significantly decrease the hatching rate of Sarcoptes eggs. CONCLUSIONS/SIGNIFICANCE: Lemongrass oil should be considered as a promising miticidal and ovicidal agent for scabies control.


Assuntos
Acaricidas/farmacologia , Cymbopogon/química , Óleos Vegetais/farmacologia , Sarcoptes scabiei/efeitos dos fármacos , Terpenos/farmacologia , Acaricidas/isolamento & purificação , Animais , Bioensaio , Espectrometria de Massas , Óleos Vegetais/isolamento & purificação , Sarcoptes scabiei/fisiologia , Análise de Sobrevida , Terpenos/isolamento & purificação
9.
Adv Exp Med Biol ; 1260: 283-296, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32304038

RESUMO

In our society, anxiety and depression are serious health issues that affect a large proportion of the population. Unfortunately, drug therapies are not always effective and can lead to drug abuse, delay of therapeutic effect, dependence, and tolerance. Traditionally, aromatherapy has also been used for anxiety relief and mood improvement. The use of essential oils, in relieving anxiety and depression, does not have the disadvantages associated with currently used drug therapies. In-vivo studies on animal models have verified the anxiolytic effects of these essential oils and the interactions of their major components with central nervous system receptors. Therefore, it seems reasonable to argue that the modulation of glutamate and GABA neurotransmitter systems are likely to be the critical mechanisms responsible for the sedative, anxiolytic, and anticonvulsant proprieties of linalool and essential oils containing linalool in significant proportions. Popular anxiolytic essential oils are generally rich in terpenoid alcohols like linalool, geraniol and citronellol, and the monoterpene limonene (or citral). Therefore, other essential oils or formulations that contain these terpenoids as major components may serve as important aromatherapeutics for relief of anxiety.


Assuntos
Ansiolíticos/uso terapêutico , Ansiedade/tratamento farmacológico , Aromaterapia , Depressão/tratamento farmacológico , Óleos Voláteis/uso terapêutico , Terpenos/uso terapêutico , Animais , Ansiolíticos/química , Ansiolíticos/farmacologia , Anticonvulsivantes/química , Anticonvulsivantes/farmacologia , Anticonvulsivantes/uso terapêutico , Humanos , Hipnóticos e Sedativos/química , Hipnóticos e Sedativos/farmacologia , Hipnóticos e Sedativos/uso terapêutico , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Terpenos/química , Terpenos/farmacologia
10.
Mar Drugs ; 18(4)2020 Apr 11.
Artigo em Inglês | MEDLINE | ID: mdl-32290492

RESUMO

The anti-inflammatory and anticancer properties of eight meroterpenoids isolated from the brown seaweed Cystoseira usneoides have been evaluated. The algal meroterpenoids (AMTs) 1-8 were tested for their inhibitory effects on the production of the pro-inflammatory cytokines tumor necrosis factor (TNF-α), interleukin-6 (IL-6), and interleukin-1ß (IL-1ß), and the expression of cyclooxygenase-2 (COX-2), and inducible nitric oxide synthase (iNOS) in LPS-stimulated THP-1 human macrophages. The anticancer effects were assessed by cytotoxicity assays against human lung adenocarcinoma A549 cells and normal lung fibroblastic MRC-5 cells, together with flow cytometry analysis of the effects of these AMTs on different phases of the cell cycle. The AMTs 1-8 significantly reduced the production of TNF-α, IL-6, and IL-1ß, and suppressed the COX-2 and iNOS expression, in LPS-stimulated cells (p < 0.05). The AMTs 1-8 displayed higher cytotoxic activities against A549 cancer cells than against MRC-5 normal lung cells. Cell cycle analyses indicated that most of the AMTs caused the arrest of A549 cells at the G2/M and S phases. The AMTs 2 and 5 stand out by combining significant anti-inflammatory and anticancer activities, while 3 and 4 showed interesting selective anticancer effects. These findings suggest that the AMTs produced by C. usneoides may have therapeutic potential in inflammatory diseases and lung cancer.


Assuntos
Anti-Inflamatórios/química , Antineoplásicos/química , Organismos Aquáticos , Feófitas , Terpenos/química , Células A549/efeitos dos fármacos , Animais , Anti-Inflamatórios/farmacologia , Antineoplásicos/farmacologia , Citocinas/efeitos dos fármacos , Humanos , Terpenos/farmacologia
11.
J Appl Microbiol ; 129(3): 541-553, 2020 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-32271977

RESUMO

AIM: This study investigated the in vitro mechanism of action of a commercial citrus EO, Brazilian orange terpenes (BOT), on an enterotoxigenic Escherichia coli (ETEC) isolated from pig gut and on Lactobacillus rhamnosus. METHODS AND RESULTS: Firstly, bacteria were exposed sequentially to BOT every 3 h (three times) at sub-minimal inhibitory concentrations and results showed that sequential exposure to BOT provoked a higher reduction of bacteria viability than a single exposure and the reduction of ETEC viability was higher compared to that of L. rhamnosus. Then, evaluation of the BOT effects on the cell membrane permeability and integrity, indicated that BOT increased the membrane permeability and caused disruptive effects on the integrity of bacterial cells as reflected by an increase of the relative electric conductivity and the release of essential cell constituents. Interestingly, BOT effects were more pronounced on the ETEC than on L. rhamnosus. This was ratified by scanning electron microscopy, which showed more noticeable morphological damages and disturbances on ETEC cells than on the L. rhamnosus cells. Limonene was detected as the major compound in BOT by polar/nonpolar GC-MS (78·65%/79·38%). CONCLUSIONS: Results revealed that the probable mechanism of the selective antibacterial action of the citrus EO, BOT, can be described as altering more remarkable the permeability and integrity of the cytoplasmic membrane as well as the external structure of ETEC cells than L. rhamnosus cells. SIGNIFICANCE AND IMPACT OF THE STUDY: This study provides information about the mechanism of antibacterial action displayed by a citrus EO, a by-product of the citrus processing industry, as a natural alternative to antibiotics used in pig production sector to combat pathogens such as ETECs.


Assuntos
Antibacterianos/farmacologia , Citrus/química , Escherichia coli Enterotoxigênica/efeitos dos fármacos , Lactobacillus rhamnosus/efeitos dos fármacos , Óleos Voláteis/farmacologia , Animais , Membrana Celular/efeitos dos fármacos , Membrana Celular/metabolismo , Escherichia coli Enterotoxigênica/isolamento & purificação , Testes de Sensibilidade Microbiana , Óleos Voláteis/química , Especificidade da Espécie , Suínos , Terpenos/farmacologia
12.
J Pharmacol Sci ; 143(3): 156-164, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-32278466

RESUMO

Safranal (SFR) is the major constituent of saffron. The purpose of this study was to observe the effect of SFR on myocardial ischemia induced by isoprenaline (ISO) and to explore its possible mechanism. The myocardial ischemia rat model was established by subcutaneous injection of ISO (85 mg/kg/d) on the 8th and 9th day of the experiment. Serum creatine kinase (CK), lactate dehydrogenase (LDH), malondialdehyde (MDA) and superoxide dismutase (SOD) were measured, as were changes in calcium concentration, reactive oxygen species (ROS) and cardiac morphology of the myocardial tissue. The effects of SFR on cell contraction, Ca2+ transient and L-type Ca2+ current (ICa-L) in isolated rat myocardial cells were measured using the Ion Optix detection system and the whole-cell patch-clamp technique. SFR can decrease the activity of serum CK, LDH and MDA, and increase the activity of serum SOD, reduce intracellular calcium concentration and the manufacture of ROS. In addition, SFR can improve changes in heart morphology. SFR can significantly inhibit contraction, Ca2+ transients and ICa-L in isolated ventricular myocytes. SFR has a cardioprotective role in ISO-induced MI rats, and the underling mechanism is related to the inhibition of oxidative stress, myocardial contractility, ICa-L and the regulation of Ca2+ homeostasis.


Assuntos
Cálcio/metabolismo , Crocus/química , Cicloexenos/farmacologia , Cicloexenos/uso terapêutico , Isquemia Miocárdica/tratamento farmacológico , Isquemia Miocárdica/metabolismo , Miocárdio/metabolismo , Estresse Oxidativo/efeitos dos fármacos , Fitoterapia , Terpenos/farmacologia , Terpenos/uso terapêutico , Animais , Cardiotônicos , Células Cultivadas , Cicloexenos/isolamento & purificação , Modelos Animais de Doenças , Isoproterenol/efeitos adversos , Masculino , Malondialdeído/metabolismo , Contração Miocárdica/efeitos dos fármacos , Isquemia Miocárdica/induzido quimicamente , Ratos Sprague-Dawley , Superóxido Dismutase/metabolismo , Terpenos/isolamento & purificação
13.
Langmuir ; 36(16): 4317-4323, 2020 04 28.
Artigo em Inglês | MEDLINE | ID: mdl-32271592

RESUMO

We present self-assembled Pickering emulsions containing biocidal phytochemical oils (carvacrol and terpinen-4-ol) and ß-cyclodextrin able to potentiate the antimicrobial and antibiofilm activity of miconazoctylium bromide. The carvacrol-containing emulsion is 2-fold more sensitive against C. albicans and S. aureus and highly active against E. coli, compared to the commercial cream containing miconazole nitrate. Moreover, this emulsion shows a synergistic effect against fungi, additive responses against bacteria, and remarkable staphylococcal biofilm eradication. These results are associated with membrane permeabilization, enzymes inhibition, and the accumulation of reactive oxygen species in microorganisms.


Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Biofilmes/efeitos dos fármacos , Ciclodextrinas/química , Emulsões/química , Candida albicans/efeitos dos fármacos , Cimenos/farmacologia , Escherichia coli/efeitos dos fármacos , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Staphylococcus aureus Resistente à Meticilina/fisiologia , Terpenos/farmacologia
14.
Molecules ; 25(3)2020 Feb 06.
Artigo em Inglês | MEDLINE | ID: mdl-32041149

RESUMO

Plant phytochemicals have potential decontaminating properties, however, their role in the amelioration of hydrophobic water filtration membranes have not been elucidated yet. In this work, phytochemicals (i.e., cannabinoids (C) and terpenes (T) from C. sativa) were revealed for their antibacterial activity against different Gram-positive and Gram-negative bacteria. As such, a synergistic relationship was observed between the two against all strains. These phytochemicals individually and in combination were used to prepare polyethersulfone (PES) hybrid membranes. Membrane characterizations were carried out using scanning electron microscopy, Fourier transform infrared spectroscopy, energy-dispersive X-ray spectroscopy. Moreover, contact angle, water retention, surface roughness, mechanical testing, and X-ray florescence analysis were also carried out. According to results, the CT-PES hybrid membrane exhibited the lowest contact angle (40°), the highest water retention (70%), and smallest average pore size (0.04 µm). The hybrid membrane also exhibited improved water flux with no surface leaching. Quantitative bacterial decline analysis of the CT-PES hybrid membranes confirmed an effective antibacterial performance against Gram-positive and Gram-negative bacteria. The results of this study established cannabinoids and terpenes as an inexpensive solution for PES membrane surface modification. These hybrid membranes can be easily deployed at an industrial scale for water filtration purposes.


Assuntos
Antibacterianos/farmacologia , Canabinoides/farmacologia , Terpenos/farmacologia , Antibacterianos/química , Canabinoides/química , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Membranas Artificiais , Microscopia Eletrônica de Varredura , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Polímeros , Sulfonas , Terpenos/química , Purificação da Água/instrumentação
15.
Biochem Biophys Res Commun ; 525(2): 303-307, 2020 04 30.
Artigo em Inglês | MEDLINE | ID: mdl-32089263

RESUMO

Microtubules are involved in celluar processes of movement, intracellular trafficking and mitosis, thus microtubule-targeting agents have been widely used in cancer therapy. Herein, we report isopenicin A, a novel meroterpenoid isolated from the plant endophytic fungus of Penicillium sp. sh18, as a novel microtubule binding molecule that efficiently depolymerizes microtubule polymerization to evoke G2/M cell cycle arrest and subsequent cell apoptosis, contributing to proliferation inhibition of human tumor cell lines. The discovery of isopenicin A provides a new chemotype for discovery and development of promising microtubule inhibitors.


Assuntos
Antineoplásicos/isolamento & purificação , Penicillium/química , Moduladores de Tubulina/isolamento & purificação , Antineoplásicos/farmacologia , Apoptose/efeitos dos fármacos , Linhagem Celular Tumoral , Pontos de Checagem da Fase G2 do Ciclo Celular/efeitos dos fármacos , Humanos , Microtúbulos/metabolismo , Polimerização/efeitos dos fármacos , Terpenos/isolamento & purificação , Terpenos/farmacologia , Tubulina (Proteína)/metabolismo , Moduladores de Tubulina/farmacologia
16.
Org Lett ; 22(4): 1336-1339, 2020 02 21.
Artigo em Inglês | MEDLINE | ID: mdl-32037840

RESUMO

Aspermeroterpene A (1) with an unprecedented and highly congested 5/3/6/6/6/5 hexacyclic skeleton, together with two precursors aspermeroterpenes B (2) and C (3), were isolated from the marine-derived fungus Aspergillus terreus GZU-31-1. Their structures were elucidated by quantum chemical calculations, X-ray diffraction, and spectroscopic methods. The biogenetic pathway for 1-3 is proposed. Aspermeroterpenes A-C (1-3) showed significant inhibitory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 cells compared to positive control.


Assuntos
Aspergillus/química , Terpenos/farmacologia , Animais , Cristalografia por Raios X , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Camundongos , Modelos Moleculares , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Células RAW 264.7 , Terpenos/química , Terpenos/isolamento & purificação
17.
Molecules ; 25(3)2020 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-32019210

RESUMO

Pharmaceutical products of essential oil from Zingiber cassumunar Roxb. are extensively being developed, while the research on their safety is seldom documented. The aim of the present study was to evaluate the phytochemical profile and the effect of cassumunar ginger oil on cell-based assay and the zebrafish model. The essential oil was isolated from fresh rhizomes of Z. cassumunar using simultaneous steam-distillation. Chemical composition was analyzed using gas chromatograph coupled to a mass spectrometer (GC-MS). Effect of cassumunar ginger oil on adult carp fish peripheral blood mononuclear cells (PBMCs) was investigated using MTT assay. The embryotoxic and teratogenic effects of cassumunar ginger oil were studied in zebrafish embryos. GC-MS results showed that the essential oil was composed of sabinene (43.54%) and terpinen-4-ol (29.52%) as the major phytoconstituents. No fish PBMC cytotoxic effect was observed with the concentration less than 50 µg/mL of cassumunar ginger oil. Our results showed for the first time the embryotoxic and teratogenic effects of cassumunar ginger oil in zebrafish embryos. The result indicated that the cassumunar ginger oil induced zebrafish embryotoxicity in a concentration-dependent manner. At 500 µg/mL of cassumunar ginger oil demonstrated significantly moderated embryotoxicity within 24 h (p < 0.05). The survival rate of 100 µg/mL of cassumunar ginger group was markedly declined to zero at 96-h post-fertilization (log-rank test, p = 0.001). However, survival rates of zebrafish embryo in the 1 and 10 µg/mL cassumunar ginger groups were more than 90% throughout the trial period. Moreover, very low teratogenicity to the zebrafish embryo was also observed in 1 and 10 µg/mL of cassumunar ginger groups. Our findings suggest that there is hardly any cytotoxicity, embryotoxicity and teratogenicity at concentrations less than 10 µg/mL of cassumunar ginger oil. However, the toxicity assessment of its pharmaceutical product should prove for further consumer protection.


Assuntos
Embrião não Mamífero/efeitos dos fármacos , Gengibre/química , Leucócitos Mononucleares/efeitos dos fármacos , Óleos Voláteis/farmacologia , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Terpenos/farmacologia , Animais , Carpas , Peixe-Zebra
18.
Toxicol Appl Pharmacol ; 389: 114882, 2020 01 15.
Artigo em Inglês | MEDLINE | ID: mdl-31953203

RESUMO

Pulmonary fibrosis is a prototypic chronic progressive lung disease with high morbidity and mortality worldwide. Novel effective therapeutic agents are urgently needed owing to the limited treatment options in clinic. Herein, nagilactone D (NLD), a natural dinorditerpenoid obtained from Podocarpus nagi, was found to suppress transforming growth factor-ß1 (TGF-ß1)-mediated fibrotic process in vitro and bleomycin (BLM)-induced pulmonary fibrosis in vivo. NLD attenuated TGF-ß1-induced expression of fibrotic markers including type I and III collagen, fibronectin, α-SMA, and CTGF in human pulmonary fibroblasts (WI-38 VA-13 and HLF-1 cells). Mechanism study indicated that NLD suppressed TGF-ß1-induced up-regulation of TßR I, and Smad2 phosphorylation, nuclear translocation, and transcriptional activation. Moreover, NLD ameliorated BLM-induced histopathological abnormalities in the lungs of experimental fibrotic mice, suppressed synthesis of relative fibrotic markers and fibroblast-to-myofibroblast transition, as well as BLM-induced up-regulation of TßR I expression and Smad signaling in mouse lungs. These data collectively support NLD to be a potential therapeutic agent for pulmonary fibrosis.


Assuntos
Diterpenos/farmacologia , Fibroblastos/efeitos dos fármacos , Fibrose Pulmonar/tratamento farmacológico , Proteína Smad2/metabolismo , Terpenos/farmacologia , Fator de Crescimento Transformador beta1/metabolismo , Animais , Biomarcadores/metabolismo , Bleomicina/farmacologia , Células Cultivadas , Feminino , Fibroblastos/metabolismo , Humanos , Pulmão/efeitos dos fármacos , Pulmão/metabolismo , Camundongos , Camundongos Endogâmicos C57BL , Miofibroblastos/efeitos dos fármacos , Miofibroblastos/metabolismo , Fibrose Pulmonar/metabolismo , Receptor do Fator de Crescimento Transformador beta Tipo I/metabolismo , Transdução de Sinais/efeitos dos fármacos
19.
Org Biomol Chem ; 18(6): 1135-1139, 2020 02 14.
Artigo em Inglês | MEDLINE | ID: mdl-31967630

RESUMO

Biomimetic total syntheses of baefrutones A-D (1-4), baeckenon B (5), and frutescones A, D-F (6-9), isolated from the leaves of Baeckea frutescens, were achieved in 9, 8, and 5 steps, respectively, in moderate to good yields (72-83%). The synthetic routes feature the Michael addition, oxidative [4 + 2] cycloaddition, and water-promoted Diels-Alder click reactions as the key steps. This study helped gain thorough mechanistic insights into the biosynthetic origins and provided a facile approach for the construction of a library of natural tasmanone-based meroterpenoid analogues. Moreover, compounds 1-9 show potent inhibitory effects against S. paratyphi and/or C. albicans with MIC values of 3.125-25 µg mL-1, and they could be promising lead molecules for the design of new antibiotic agents.


Assuntos
Materiais Biomiméticos/farmacologia , Monoterpenos/farmacologia , Terpenos/farmacologia , Materiais Biomiméticos/síntese química , Materiais Biomiméticos/química , Candida albicans/efeitos dos fármacos , Reação de Cicloadição , Teoria da Densidade Funcional , Relação Dose-Resposta a Droga , Testes de Sensibilidade Microbiana , Estrutura Molecular , Monoterpenos/síntese química , Monoterpenos/química , Oxirredução , Pseudomonas aeruginosa/efeitos dos fármacos , Salmonella/efeitos dos fármacos , Staphylococcus aureus/efeitos dos fármacos , Estereoisomerismo , Relação Estrutura-Atividade , Terpenos/síntese química , Terpenos/química
20.
Molecules ; 25(2)2020 Jan 08.
Artigo em Inglês | MEDLINE | ID: mdl-31936396

RESUMO

BACKGROUND: Natural meroterpenes derived from phloroglucinols and ß-caryophyllene have shown high inhibitory activity against α-glucosidase or cancer cells, however, the chemical diversity of this type of skeletons in Nature is limited. METHODS: To expand the chemical space and explore their inhibitory activities against α-glucosidase (EC 3.2.1.20), we employed ß-caryophyllene and some natural moieties (4-hydroxycoumarins, lawsone or syncarpic acid) to synthesize new types of meroterpene-like skeletons. All the products (including side products) were isolated and characterized by NMR, HR-MS, and ECD. RESULTS: In total, 17 products (representing seven scaffolds) were generated through a one-pot procedure. Most products (12 compounds) showed more potential activity (IC50 < 25 µM) than the positive controls (acarbose and genistein, IC50 58.19, and 54.74 µM, respectively). Compound 7 exhibited the most potent inhibition of α-glucosidase (IC50 3.56 µM) in a mixed-type manner. The CD analysis indicated that compound 7 could bind to α-glucosidase and influence the enzyme's secondary structure. CONCLUSIONS: Compound 7 could serve as a new type of template compound to develop α-glucosidase inhibitors. Full investigation of a biomimic reaction can be used as a concise strategy to explore diverse natural-like skeletons and search for novel lead compounds.


Assuntos
Materiais Biomiméticos/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Sesquiterpenos Policíclicos/farmacologia , Terpenos/farmacologia , Cinética , Espectroscopia de Ressonância Magnética , Terpenos/síntese química , Terpenos/química
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