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1.
An Acad Bras Cienc ; 93(suppl 4): e20210550, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34730626

RESUMO

The aim of this study was to investigate the combined effect of carvacrol, thymol and nisin against Staphylococcus aureus and the combined effect of carvacrol and thymol against Salmonella Enteritidis. Minimum inhibitory concentrations (MIC) of carvacrol, thymol, and nisin for S. aureus were 200, 150 and 30 µg/mL, respectively. MIC of carvacrol and thymol for Salmonella Enteritidis was 200 µg/mL. A factorial method of independent variables was then used to study the combined effect of antimicrobials. Results showed that combinations of carvacrol-thymol-nisin (reduction of 1.2 log CFU/mL for MIC and 4.98 log CFU/mL for 2MIC), carvacrol-thymol (reduction of 1.33 log CFU/mL for 2MIC), nisin-thymol (reduction of 3.52 log CFU/mL for 2MIC) and nisin-carvacrol (reduction of 3.41 log CFU/mL for 2MIC) attained a significant inhibition of S. aureus. Similarly, there was significant reduction of Salmonella Enteritidis due to combined effect of thymol-carvacrol (reduction of 4.5 log CFU/mL for MIC and inhibition below detection limit for 2MIC). Therefore, the combinations of natural antimicrobials described in this work showed potential to be used as an additional barrier for food safety.


Assuntos
Nisina , Timol , Antibacterianos/farmacologia , Cimenos , Testes de Sensibilidade Microbiana , Monoterpenos/farmacologia , Nisina/farmacologia , Salmonella enteritidis , Staphylococcus aureus , Timol/farmacologia
2.
Zhongguo Zhong Yao Za Zhi ; 46(19): 5015-5019, 2021 Oct.
Artigo em Chinês | MEDLINE | ID: mdl-34738396

RESUMO

Five monoterpenoid compounds(1-5) were isolated and purified from the acetone fraction of the aqueous extract of Zingiberis Rhizoma Recens by MCI, Sephadex LH-20, silica gel, semi-preparative HPLC, and TLC. Their structures were identified with multiple spectroscopical methods including 1 D-NMR, 2 D-NMR, and MS. The five compounds were identified as(2E,6Z)-8-hydroxy-2,6-dimethylocta-2,6-dien-1-yl-(E)-3-(4-hydroxy-3-methoxyphenyl) acrylate(1),(2E,6E)-8-hydroxy-3,7-dimethylocta-2,6-die-noic acid(2),(E)-1,8-dihydroxy-3,7-dimethyl-2-octenoic acid(3), linalyl-ß-D-glucopyranoside(4), and ß-D-glucopyranoside-(2E)-3,7-dimethyl-2,6-octadien-1-yl(5), respectively.Compound 1 was a new monoterpene ester, and compounds 4-5 were isolated from this plant for the first time.


Assuntos
Ésteres , Monoterpenos , Cromatografia Líquida de Alta Pressão , Rizoma
3.
Environ Sci Technol ; 55(21): 14595-14606, 2021 11 02.
Artigo em Inglês | MEDLINE | ID: mdl-34668375

RESUMO

The partition of gas-phase organic nitrates (ONs) to aerosols and subsequent hydrolysis are regarded as important loss mechanisms for ON species. However, the hydrolysis mechanisms and the major factors controlling the hydrolysis lifetime are not fully understood. In this work, we synthesized seven monoterpene-derived ONs and systematically investigated their hydrolysis in bulk solutions at different pH values. The hydrolysis lifetimes ranged from 12.9 min to 8.5 h for allylic primary ON and tertiary ONs, but secondary ONs were stable at neutral pH. The alkyl substitution numbers, functional groups, and carbon skeletons were three important factors controlling hydrolysis rates. Tertiary and secondary ONs were found to hydrolyze via the acid-catalyzed unimolecular (SN1) mechanism, while a competition of SN1 and bimolecular (SN2) mechanisms accounted for the hydrolysis of primary ONs. The consistency of experimental and theoretical hydrolysis rates calculated by density functional theory further supported the proposed mechanisms. Reversible reactions including hydrolysis and nitration were first reported to explain the hydrolysis of ONs, highlighting the possibility that particulate nitric acid can participate in nitration to generate new nitrogen-containing compounds. These findings demonstrate that ON hydrolysis is a complex reaction that proceeds via different mechanisms and is controlled by various parameters.


Assuntos
Monoterpenos , Nitratos , Ácidos , Aerossóis , Hidrólise
4.
Parasitol Res ; 120(11): 3837-3844, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34604934

RESUMO

Schistosomiasis is a major public health problem that afflicts more than 240 million individuals globally, particularly in poor communities. Treatment of schistosomiasis relies heavily on a single oral drug, praziquantel, and there is interest in the search for new antischistosomal drugs. This study reports the anthelmintic evaluation of carvacryl acetate, a derivative of the terpene carvacrol, against Schistosoma mansoni ex vivo and in a schistosomiasis animal model harboring either adult (patent infection) or juvenile (prepatent infection) parasites. For comparison, data obtained with gold standard antischistosomal drug praziquantel are also presented. Initially in vitro effective concentrations of 50% (EC50) and 90% (EC90) were determined against larval and adult stages of S. mansoni. In an animal with patent infection, a single oral dose of carvacryl acetate (100, 200, or 400 mg/kg) caused a significant reduction in worm burden (30-40%). S. mansoni egg production, a process responsible for both life cycle and pathogenesis, was also markedly reduced (70-80%). Similar to praziquantel, carvacryl acetate 400 mg/kg had low efficacy in pre-patent infection. In tandem, although carvacryl acetate had interesting in vitro schistosomicidal activity, the compound exhibited low efficacy in terms of reduction of worm load in S. mansoni-infected mice.


Assuntos
Esquistossomose mansoni , Esquistossomicidas , Administração Oral , Animais , Camundongos , Monoterpenos , Schistosoma mansoni , Esquistossomose mansoni/tratamento farmacológico , Esquistossomicidas/uso terapêutico
5.
Molecules ; 26(19)2021 Sep 23.
Artigo em Inglês | MEDLINE | ID: mdl-34641307

RESUMO

Over 15 years, with the support of a Canadian funding agency, the Universidad Mayor de San Simón, in Bolivia, undertook a large survey of aromatic plants of the South American country. More than a hundred species were studied under various aspects, including the production and characterization of essential oils. As part of this survey, the chemical composition of an essential oil sample obtained from Pentacalia herzogii (Asteraceae) growing wild in the High Valley region of the department of Cochabamba was determined by a combination of GC and GC-MS measurements. α-Pinene was the main constituent of this essential oil (34%), accompanied by limonene (22%) and germacrene D (7.5%) as well as an important fraction of methoxylated monoterpenoids. They were mainly isomers of thymol methyl ether, accounting for 13% of the chromatogram. A new quantitatively important compound (9%) was identified through NMR and chemical synthesis as 4-isopropyl-6-methylbenzo[d][1,3]dioxole, and designated herzogole, alongside the minor related compound 1-isopropyl-2,3-dimethoxy-5-methylbenzene. The monoterpene benzodioxole featured a distinctive green-phenolic aroma which could raise interest for fragrance use. Since these compounds were not known naturally, a biosynthetic mechanism of their formation was proposed and put in perspective to illustrate the metabolic originality of P. herzogii.


Assuntos
Asteraceae/química , Benzodioxóis/isolamento & purificação , Óleos Voláteis/análise , Monoterpenos Bicíclicos/isolamento & purificação , Cromatografia Gasosa-Espectrometria de Massas , Limoneno/isolamento & purificação , Monoterpenos/isolamento & purificação , Óleos Voláteis/química , Componentes Aéreos da Planta/química , Óleos Vegetais/análise , Óleos Vegetais/química , Sesquiterpenos de Germacrano/isolamento & purificação
6.
Molecules ; 26(19)2021 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-34641513

RESUMO

A study on the headspace volatile organic compounds (VOCs) profile of native populations of Sideritis romana L. and Sidertis montana L., Lamiaceae, from Croatia is reported herein, to elucidate the phytochemical composition of taxa from this plant genus, well-known for traditional use in countries of the Mediterranean and the Balkan region. Headspace solid-phase microextraction (HS-SPME), using divinylbenzene/carboxene/polydimethylsiloxane (DVB/CAR/PDMS) or polydimethylsiloxane/divinylbenzene (PDMS/DVB) fiber, coupled with gas chromatography-mass spectrometry (GC-MS) was applied to analyze the dried aerial parts of six native populations in total. Furthermore, principal component analysis (PCA) was conducted on the volatile constituents with an average relative percentage ≥1.0% in at least one of the samples. Clear separation between the two species was obtained using both fiber types. The VOCs profile for all investigated populations was characterized by sesquiterpene hydrocarbons, followed by monoterpene hydrocarbons, except for one population of S. romana, in which monoterpene hydrocarbons predominated. To our knowledge, this is the first report on the VOCs composition of natural populations of S. romana and S. montana from Croatia as well as the first reported HS-SPME/GC-MS analysis of S. romana and S. montana worldwide.


Assuntos
Sideritis/química , Compostos Orgânicos Voláteis/análise , Croácia , Dimetilpolisiloxanos/química , Cromatografia Gasosa-Espectrometria de Massas/métodos , Monoterpenos/análise , Compostos Fitoquímicos/análise , Polivinil/química , Análise de Componente Principal , Sesquiterpenos/análise , Microextração em Fase Sólida/instrumentação , Microextração em Fase Sólida/métodos
7.
Zhongguo Zhong Yao Za Zhi ; 46(15): 3943-3948, 2021 Aug.
Artigo em Chinês | MEDLINE | ID: mdl-34472271

RESUMO

The study aims to investigate the effect of the compatibility of paeonol and paeoniflorin(hereinafter referred to as the compatibility) on the expression of myocardial proteins in rats with myocardial ischemia injury and explore the underlying mechanism of the compatibility against myocardial ischemia injury. First, the acute myocardial infarction rat model was established by ligation of the anterior descending branch of the left coronary artery. The model rats were given(ig) paeonol and paeoniflorin. Then protein samples were collected from rat cardiac tissue and quantified by tandem mass tags(TMT) to explore the differential proteins after drug intervention. The experimental results showed that differential proteins mainly involved phagocytosis engulfment, extracellular space, and antigen binding, as well as Kyoto encyclopedia of genes and genomes(KEGG) pathways of complement and coagulation cascades, syste-mic lupus erythematosus, and ribosome. In this study, the target proteins and related signaling pathways identified by differential proteomics may be the biological basis of the compatibility against myocardial ischemia injury in rats.


Assuntos
Isquemia Miocárdica , Traumatismo por Reperfusão Miocárdica , Acetofenonas , Animais , Glucosídeos , Monoterpenos , Isquemia Miocárdica/tratamento farmacológico , Isquemia Miocárdica/genética , Proteômica , Ratos , Ratos Sprague-Dawley
8.
Molecules ; 26(17)2021 Aug 24.
Artigo em Inglês | MEDLINE | ID: mdl-34500567

RESUMO

Cinnamomum camphora L. is grown as an ornamental plant, used as raw material for furniture, as a source of camphor, and its essential oil can be used as an important source for perfume as well as alternative medicine. A comparative investigation of essential oil compositions and antimicrobial activities of different tissues of C. camphora was carried out. The essential oils were extracted by hydrodistillation with a Clevenger apparatus and their compositions were evaluated through gas chromatography-mass spectrometry (GC-MS), enantiomeric composition by chiral GC-MS, and antimicrobial properties were assayed by measuring minimum inhibitory concentrations (MICs). Different plant tissues had different extraction yields, with the leaf having the highest yield. GC-MS analysis revealed the presence of 18, 75, 87, 67, 67, and 74 compounds in leaf, branch, wood, root, leaf/branch, and leaf/branch/wood, respectively. The significance of combining tissues is to enable extraction of commercial quality essential oils without the need to separate them. The oxygenated monoterpene camphor was the major component in all tissues of C. camphora except for safrole in the root. With chiral GC-MS, the enantiomeric distributions of 12, 12, 13, 14, and 14 chiral compounds in branch, wood, root, leaf/branch, and leaf/branch/wood, respectively, were determined. The variation in composition and enantiomeric distribution in the different tissues of C. camphora may be attributed to the different defense requirements of these tissues. The wood essential oil showed effective antibacterial activity against Serratia marcescens with an MIC of 39.1 µg/mL. Similarly, the mixture of leaf/branch/wood essential oils displayed good antifungal activity against Aspergillus niger and Aspergillus fumigatus while the leaf essential oil was notably active against Trichophyton rubrum. C. camphora essential oils showed variable antimicrobial activities against dermal and pulmonary-borne microbes.


Assuntos
Antibacterianos/química , Antibacterianos/farmacologia , Cinnamomum camphora/química , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Antifúngicos/química , Antifúngicos/farmacologia , Arthrodermataceae/efeitos dos fármacos , Aspergillus niger/efeitos dos fármacos , Cromatografia Gasosa-Espectrometria de Massas/métodos , Testes de Sensibilidade Microbiana/métodos , Monoterpenos/química , Monoterpenos/farmacologia , Folhas de Planta/química , Óleos Vegetais/química , Óleos Vegetais/farmacologia , Raízes de Plantas/química
9.
Phytomedicine ; 92: 153724, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34509953

RESUMO

BACKGROUND: Influenza often leads to acute lung injury (ALI). Few therapeutics options such as vaccines and other antiviral drugs are available. Paeoniflorin is a monoterpene glucoside isolated from the roots of Paeonia lactiflora Pall. that has showed good anti-inflammatory and anti-fibrotic effects. However, it is not known whether paeoniflorin has an effect on influenza virus-induced ALI. PURPOSE: To investigative the protective effect and potential mechanism of paeoniflorin on ALI induced by influenza A virus (IAV). STUDY DESIGN AND METHODS: The anti-influenza activity of paeoniflorin in vitro was investigated. Influenza virus A/FM/1/47 was intranasally infected in mice to induce ALI, and paeoniflorin (50 and 100 mg/kg) was given orally to mice during 5 days, beginning 2 h after infection. On day 6 post-infection, body and lung weights, histology and survival were observed, and the lungs were examined for viral load, cytokine and cellular pathway protein expression. RESULTS: Results showed that paeoniflorin (50 and 100 mg/kg) reduced IAV-induced ALI. It reduces pulmonary oedema and improves histopathological changes in the lung, and also diminishes the accumulation of inflammatory cells in the lung. It was shown that paeoniflorin (50 and 100 mg/kg) alleviated IAV-induced ALI, as evidenced by improved survival in infected mice (40% and 50%, respectively), reduced viral titer in lung tissue, improved histological changes, and reduced lung inflammation. Paeoniflorin also improves pulmonary fibrosis by reducing the levels of pulmonary fibrotic markers (collagen type IV, alpha-smooth muscle actin, hyaluronic acid, laminin, and procollagen type III) and downregulating the expression levels of type I collagen (Col I) and type III collagen (Col III) in the lung tissues. Additionally, paeoniflorin inhibits the expression of αvß3, TGF-ß1, Smad2, NF-κB, and p38MAPK in the lung tissues. CONCLUSION: The results showed that paeoniflorin (50 and 100 mg/kg) protected against IAV-induced ALI, and the underlying mechanism may be related to the reduction of pro-inflammatory cytokine production and lung collagen deposition through down-regulation of activation of αvß3/TGF-ß1 pathway in lung tissue.


Assuntos
Lesão Pulmonar Aguda , Vírus da Influenza A , Lesão Pulmonar Aguda/tratamento farmacológico , Animais , Glucosídeos/farmacologia , Pulmão , Camundongos , Monoterpenos/farmacologia
10.
Molecules ; 26(18)2021 Sep 16.
Artigo em Inglês | MEDLINE | ID: mdl-34577081

RESUMO

The quality control of essential oils (EO) principally aims at revealing the presence of adulterations and at quantifying compounds that are limited by law by evaluating EO chemical compositions, usually in terms of the normalised relative abundance of selected markers, for comparison to reference values reported in pharmacopoeias and/or international norms. Common adulterations of EO consist of the addition of cheaper EO or synthetic materials. This adulteration can be detected by calculating the percent normalised areas of selected markers or the enantiomeric composition of chiral components. The dilution of the EO with vegetable oils is another type of adulteration. This adulteration is quite devious, as it modifies neither the qualitative composition of the resulting EO nor the marker's normalised percentage abundance, which is no longer diagnostic, and an absolute quantitative analysis is required. This study aims at verifying the application of the two above approaches (i.e., normalised relative abundance and absolute quantitation) to detect EO adulterations, with examples involving selected commercial EO (lavender, bergamot and tea tree) adulterated with synthetic components, EO of different origin and lower economical values and heavy vegetable oils. The results show that absolute quantitation is necessary to highlight adulteration with heavy vegetable oils, providing that a reference quantitative profile is available.


Assuntos
Citrus/química , Lavandula/química , Melaleuca/química , Óleos Voláteis/química , Controle de Qualidade , Monoterpenos Acíclicos/análise , Contaminação de Medicamentos , Cromatografia Gasosa-Espectrometria de Massas , Isomerismo , Monoterpenos/análise , Óleos Voláteis/análise , Óleos Vegetais/análise , Óleos Vegetais/química , Padrões de Referência , Óleo de Melaleuca/análise , Óleo de Melaleuca/química
11.
Molecules ; 26(17)2021 Sep 06.
Artigo em Inglês | MEDLINE | ID: mdl-34500858

RESUMO

Floral fragrance is one of the most important characteristics of ornamental plants and plays a pivotal role in plant lifespan such as pollinator attraction, pest repelling, and protection against abiotic and biotic stresses. However, the precise determination of floral fragrance is limited. In the present study, the floral volatile compounds of six Hedychium accessions exhibiting from faint to highly fragrant were comparatively analyzed via gas chromatography-mass spectrometry (GC-MS) and Electronic nose (E-nose). A total of 42 volatile compounds were identified through GC-MS analysis, including monoterpenoids (18 compounds), sesquiterpenoids (12), benzenoids/phenylpropanoids (8), fatty acid derivatives (2), and others (2). In Hedychium coronarium 'ZS', H. forrestii 'Gaoling', H. 'Jin', H. 'Caixia', and H. 'Zhaoxia', monoterpenoids were abundant, while sesquiterpenoids were found in large quantities in H. coccineum 'KMH'. Hierarchical clustering analysis (HCA) divided the 42 volatile compounds into four different groups (I, II, III, IV), and Spearman correlation analysis showed these compounds to have different degrees of correlation. The E-nose was able to group the different accessions in the principal component analysis (PCA) corresponding to scent intensity. Furthermore, the pattern-recognition findings confirmed that the E-nose data validated the GC-MS results. The partial least squares (PLS) analysis between floral volatile compounds and sensors suggested that specific sensors were highly sensitive to terpenoids. In short, the E-nose is proficient in discriminating Hedychium accessions of different volatile profiles in both quantitative and qualitative aspects, offering an accurate and rapid reference technique for future applications.


Assuntos
Flores/química , Odorantes/análise , Perfumes/química , Extratos Vegetais/análise , Compostos Orgânicos Voláteis/química , Zingiberaceae/química , Monoterpenos Cicloexânicos/análise , Nariz Eletrônico , Ácidos Graxos/análise , Cromatografia Gasosa-Espectrometria de Massas , Monoterpenos/análise , Análise de Componente Principal , Sesquiterpenos/análise , Microextração em Fase Sólida , Terpenos/análise
12.
Molecules ; 26(18)2021 Sep 20.
Artigo em Inglês | MEDLINE | ID: mdl-34577162

RESUMO

The present paper reports the GC-HS-SPME analysis of volatile emission and GC-MS analysis of chemical composition of essential oil of R. coriaria fruits of eight different samples of R. coriaria L. fruits ("sumac" folk name), collected from Jordanian agricultural field and the local market. The analyses show an important variability among the Sumac samples probably due to the origin, cultivation, harvesting period, drying, and conservation of the plant material. The main class of component present in all samples was monoterpenes (43.1 to 72.9%), except for one sample which evidenced a high percentage of sesquiterpene hydrocarbons (38.5%). The oxygenated monoterpenes provided a contribution to total class of monoterpenes ranging from 10.1 to 24.3%. A few samples were rich in monoterpene hydrocarbons. Regarding the single components present in all the volatile emissions, ß-caryophyllene was the main compound in most of the analyzed samples, varying from 34.6% to 7.9%. Only two samples were characterized by α-pinene as the main constituent (42.2 and 40.8% respectively). Essential oils were collected using hydro-distillation method. Furfural was the main constituent in almost all the analyzed EOs (4.9 to 48.1%), except in one of them, where ß-caryophyllene was the most abundant one. ß-caryophyllene ranged from 1.2 to 10.6%. Oxygenated monoterpenes like carvone and carvacrol ranged from 3.2-9.1% and 1.0-7.7% respectively. Cembrene was present in good amount in EO samples EO-2 to EO-8. The antioxidant capacities of the fruit essential oils from R. coriaria were assessed using spectrophotometry to measure free radical scavenger 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and inhibition of ß-carotene bleaching (BCB). The essential oils from the fruits of the different samples of R. coriaria exhibited the MIC value ranging from 32.8 to 131.25 µg/mL against S. aureus ATCC 6538 and 131.25 to 262.5 µg/mL against E. coli ATCC 8739. The MIC values of ciprofloxacin were 0.59 and 2.34 µg/mL against S. aureus ATCC 6538 and E. coli ATCC 8739, respectively.


Assuntos
Frutas/química , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Óleos Vegetais/química , Óleos Vegetais/farmacologia , Rhus/química , Antibacterianos/química , Antibacterianos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Monoterpenos Bicíclicos/análise , Destilação , Escherichia coli/efeitos dos fármacos , Cromatografia Gasosa-Espectrometria de Massas , Jordânia , Monoterpenos/análise , Óleos Voláteis/análise , Óleos Vegetais/análise , Sesquiterpenos Policíclicos/análise , Análise de Componente Principal , Staphylococcus aureus/efeitos dos fármacos
13.
Phytochemistry ; 190: 112857, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34365295

RESUMO

α-Pinene represents a member of the monoterpene class and is highly distributed in higher plants like conifers, Juniper ssp. and Cannabis ssp. α-Pinene has been used to treat respiratory tract infections for centuries. Furthermore, it plays a crucial role in the fragrance and flavor industry. In vitro assays have shown an enantioselective profile of (+)- and (-)-α-pinene for antibacterial and insecticidal activity, respectively. Recent research has used pre-validated biological structures to synthesize new chemical entities with pharmacological and herbicidal activities. In summary, this review focuses on recent literature covering synthetic pathways of flavor compounds and scaffold hopping based on the α-pinene core domaine, as well as the (enantioselective) activities of α-pinene. Recent approaches for authenticity control of essential oils based on their enantiomeric profile are also presented.


Assuntos
Juniperus , Óleos Voláteis , Monoterpenos Bicíclicos , Monoterpenos/farmacologia
14.
Phytomedicine ; 90: 153669, 2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34334273

RESUMO

BACKGROUND: Depression, as a prevalent and debilitating psychiatric disease, severely decreases the life quality of individuals and brings heavy burdens to the whole society. Currently, some antidepressants are applied in the treatment of severe depressive symptoms, while there are still some undesirable drawbacks. Paeoniflorin is a monoterpenoid glycoside that was firstly extracted from Paeonia lactiflora Pall, a traditional Chinese herb that is widely used in the Chinese herbal formulas for treating depression. PURPOSE: This review summarized the previous pre-clinical studies of paeoniflorin in treating depression and further discussed the potential anti-depressive mechanisms for that paeoniflorin to be further explored and utilized in the treatment of depression clinically. METHODS: Some electronic databases, e.g., PubMed and China National Knowledge Infrastructure, were searched from inception until April 2021. RESULTS: This review summarized the effective anti-depressive properties of paeoniflorin, which is related to its functions in the upregulation of the levels of monoaminergic neurotransmitters, inhibition of the hypothalamic-pituitary-adrenal axis hyperfunction, promotion of neuroprotection, promotion of hippocampus neurogenesis, and upregulation of brain-derived neurotrophic factor level, inhibition of inflammatory reaction, downregulation of nitric oxide level, etc. CONCLUSION: This review focused on the pre-clinical studies of paeoniflorin in depression and summarized the recent development of the anti-depressive mechanisms of paeoniflorin, which approves the role of paeoniflorin plays in anti-depression. However, more high-quality pre-clinical and clinical studies are expected to be conducted in the future.


Assuntos
Antidepressivos/farmacologia , Glucosídeos/farmacologia , Monoterpenos/farmacologia , Neuroproteção , Humanos , Sistema Hipotálamo-Hipofisário , Neurotransmissores , Paeonia/química , Sistema Hipófise-Suprarrenal
15.
Biomolecules ; 11(7)2021 07 01.
Artigo em Inglês | MEDLINE | ID: mdl-34356597

RESUMO

Usnic acid (UA) is a secondary metabolite of lichens that exhibits a wide range of biological activities. Previously, we found that UA derivatives are effective inhibitors of tyrosyl-DNA phosphodiesterase 1 (TDP1). It can remove covalent complex DNA-topoisomerase 1 (TOP1) stabilized by the TOP1 inhibitor topotecan, neutralizing the effect of the drugs. TDP1 removes damage at the 3' end of DNA caused by other anticancer agents. Thus, TDP1 is a promising therapeutic target for the development of drug combinations with topotecan, as well as other drugs for cancer treatment. Ten new UA enamino derivatives with variation in the terpene fragment and substituent of the UA backbone were synthesized and tested as TDP1 inhibitors. Four compounds, 11a-d, had IC50 values in the 0.23-0.40 µM range. Molecular modelling showed that 11a-d, with relatively short aliphatic chains, fit to the important binding domains. The intrinsic cytotoxicity of 11a-d was tested on two human cell lines. The compounds had low cytotoxicity with CC50 ≥ 60 µM for both cell lines. 11a and 11c had high inhibition efficacy and low cytotoxicity, and they enhanced topotecan's cytotoxicity in cancerous HeLa cells but reduced it in the non-cancerous HEK293A cells. This "protective" effect from topotecan on non-cancerous cells requires further investigation.


Assuntos
Benzofuranos/química , Monoterpenos/química , Inibidores de Fosfodiesterase , Diester Fosfórico Hidrolases/metabolismo , Benzofuranos/farmacologia , Células HEK293 , Humanos , Monoterpenos/farmacologia , Inibidores de Fosfodiesterase/síntese química , Inibidores de Fosfodiesterase/química , Inibidores de Fosfodiesterase/farmacologia
16.
Int J Mol Sci ; 22(15)2021 Jul 31.
Artigo em Inglês | MEDLINE | ID: mdl-34361036

RESUMO

Hinokitiol is a natural tropolone derivative that is present in the heartwood of cupressaceous plants, and has been extensively investigated for its anti-inflammatory, antioxidant, and antitumor properties in the context of various diseases. To date, the effects of hinokitiol on endometrial cancer (EC) has not been explored. The purpose of our study was to investigate the anti-proliferative effects of hinokitiol on EC cells. Cell viability was determined with an MTT (3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay, and the quantification of apoptosis and reactive oxygen species (ROSs) was performed by using flow cytometry, while protein expression was measured with the Western blotting technique. Hinokitiol significantly suppressed cell proliferation through the inhibition of the expression of cell-cycle mediators, such as cyclin D1 and cyclin-dependent kinase 4 (CDK4), as well as the induction of the tumor suppressor protein p53. In addition, hinokitiol increased the number of apoptotic cells and increased the protein expression of cleaved-poly-ADP-ribose polymerase (PARP) and active cleaved-caspase-3, as well as the ratio of Bcl-2-associated X protein (Bax) to B-cell lymphoma 2 (Bcl-2). Interestingly, except for KLE cells, hinokitiol induced autophagy by promoting the accumulation of the microtubule-associated protein light chain 3B (LC3B) and reducing the sequestosome-1 (p62/SQSTM1) protein level. Furthermore, hinokitiol triggered ROS production and upregulated the phosphorylation of extracellular-signal-regulated kinase (p-ERK1/2) in EC cells. These results demonstrate that hinokitiol has potential anti-proliferative and pro-apoptotic benefits in the treatment of endometrial cancer cell lines (Ishikawa, HEC-1A, and KLE).


Assuntos
Antineoplásicos Fitogênicos/toxicidade , Apoptose , Pontos de Checagem do Ciclo Celular , Neoplasias do Endométrio/metabolismo , Monoterpenos/toxicidade , Tropolona/análogos & derivados , Autofagia , Linhagem Celular Tumoral , Ciclina D1/metabolismo , Quinase 4 Dependente de Ciclina/metabolismo , Feminino , Humanos , Poli(ADP-Ribose) Polimerases/metabolismo , Espécies Reativas de Oxigênio/metabolismo , Tropolona/toxicidade , Proteína Supressora de Tumor p53/metabolismo
17.
Acta Trop ; 223: 106089, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34389324

RESUMO

The molluscicidal action of essential oils have been attributed to the most prevalent terpene compounds. However, molluscicidal properties, mode of action, and toxicity to non-target organisms remain unclear. In this study, the molluscicidal potential of four monoterpenes (camphor, thymol, α-pinene, and 1,8-cineole) against the snail Biomphalaria glabrata, an intermediate host of Schistosoma mansoni, was analyzed. The molluscicide activity of each monoterpene was assessed by the standardized test of the World Health Organization (WHO) and the monoterpenes considered active against B. glabrata were analyzed as inhibitors of the enzymatic activity of acetylcholinesterase (AChE) extracted from snails. In addition, acute toxicity to non-target organisms was assessed against Danio rerio fish. The results show that camphor and 1,8-cineole monoterpenes did not induce snail mortality. Thymol and α-pinene were active against B. glabrata, inducing mortality in concentration-dependent patterns and showing a lethal effect in concentrations compatible with that recommended by the WHO (LC90 of 7.11 and LC90 10.34 µg ∙ mL-1, respectively). The toxic action of thymol and α-pinene on snails indicates that these monoterpenes may account for or largely contribute to the molluscicidal activity of essential oils that contain them as major compounds. Thymol and α-pinene inhibit the AChE of B. glabrata at concentrations higher than those used in the molluscicide test. These monoterpenes show low toxicity to non-target organisms compared to the commercial molluscicide niclosamide. Knowledge about monoterpene toxicity against B. glabrata contributes to its potential use in molluscicidal formulations and in alternatives to the control of snails that host intermediate S. mansoni, a crucial action in the prevention and transmission of schistosomiasis, a neglected tropical disease.


Assuntos
Biomphalaria , Inibidores da Colinesterase/farmacologia , Moluscocidas , Monoterpenos , Acetilcolinesterase , Animais , Biomphalaria/efeitos dos fármacos , Biomphalaria/enzimologia , Moluscocidas/farmacologia , Monoterpenos/farmacologia , Schistosoma mansoni
18.
Environ Sci Technol ; 55(21): 14360-14369, 2021 11 02.
Artigo em Inglês | MEDLINE | ID: mdl-34404213

RESUMO

The influence of relative humidity (RH) on the condensational growth of organic aerosol particles remains incompletely understood. Herein, the RH dependence was investigated via a series of experiments for α-pinene ozonolysis in a continuously mixed flow chamber in which recurring cycles of particle growth occurred every 7 to 8 h at a given RH. In 5 h, the mean increase in the particle mode diameter was 15 nm at 0% RH and 110 nm at 75% RH. The corresponding particle growth coefficients, representing a combination of the thermodynamic driving force and the kinetic resistance to mass transfer, increased from 0.35 to 2.3 nm2 s-1. The chemical composition, characterized by O:C and H:C atomic ratios of 0.52 and 1.48, respectively, and determined by mass spectrometry, did not depend on RH. The Model for Simulating Aerosol Interactions and Chemistry (MOSAIC) was applied to reproduce the observed size- and RH-dependent particle growth by optimizing the diffusivities Db within the particles of the condensing molecules. The Db values increased from 5 α-1 × 10-16 at 0% RH to 2 α-1 × 10-12 cm-2 s-1 at 75% RH for mass accommodation coefficients α of 0.1 to 1.0, highlighting the importance of particle-phase properties in modeling the growth of atmospheric aerosol particles.


Assuntos
Ozônio , Aerossóis , Monoterpenos Bicíclicos , Umidade , Monoterpenos
19.
Molecules ; 26(11)2021 Jun 04.
Artigo em Inglês | MEDLINE | ID: mdl-34199969

RESUMO

Bee products are a well-known remedy against numerous diseases. However, from the consumers' perspective, it is essential to define factors that can affect their sensory acceptance. This investigation aimed to evaluate the volatile and sensory profiles, and sugar composition of beeswax, beebread, pollen, and honey. According to the HS-SPME/GC-MS results, 20 volatiles were identified in beeswax and honey, then 32 in beebread, and 33 in pollen. Alkanes were found to dominate in beeswax, beebread, and pollen, while aldehydes and monoterpenes in honey. In the case of sugars, a higher content of fructose was determined in beebread, bee pollen, and honey, whereas the highest content of glucose was assayed in beeswax. In the QDA, the highest aroma intensity characterized as honey-like and sweet was found in honey, while the acid aroma was typical of beebread. Other odor descriptors, including waxy, pungent, and plant-based aromas were noted only in beeswax, honey, and pollen, respectively.


Assuntos
Mel/análise , Própole/análise , Açúcares/isolamento & purificação , Compostos Orgânicos Voláteis/isolamento & purificação , Ceras/análise , Aldeídos/isolamento & purificação , Alcanos/isolamento & purificação , Animais , Abelhas , Cromatografia Gasosa-Espectrometria de Massas , Monoterpenos/isolamento & purificação
20.
Molecules ; 26(11)2021 Jun 07.
Artigo em Inglês | MEDLINE | ID: mdl-34200464

RESUMO

Due to lifespan extension and changes in global climate, the increase in mycoses caused by primary and opportunistic fungal pathogens is now a global concern. Despite increasing attention, limited options are available for the treatment of systematic and invasive mycoses, owing to the evolutionary similarity between humans and fungi. Although plants produce a diversity of chemicals to protect themselves from pathogens, the molecular targets and modes of action of these plant-derived chemicals have not been well characterized. Using a reverse genetics approach, the present study revealed that thymol, a monoterpene alcohol from Thymus vulgaris L., (Lamiaceae), exhibits antifungal activity against Cryptococcus neoformans by regulating multiple signaling pathways including calcineurin, unfolded protein response, and HOG (high-osmolarity glycerol) MAPK (mitogen-activated protein kinase) pathways. Thymol treatment reduced the intracellular concentration of Ca2+ by controlling the expression levels of calcium transporter genes in a calcineurin-dependent manner. We demonstrated that thymol decreased N-glycosylation by regulating the expression levels of genes involved in glycan-mediated post-translational modifications. Furthermore, thymol treatment reduced endogenous ergosterol content by decreasing the expression of ergosterol biosynthesis genes in a HOG MAPK pathway-dependent manner. Collectively, this study sheds light on the antifungal mechanisms of thymol against C. neoformans.


Assuntos
Antifúngicos/farmacologia , Criptococose/tratamento farmacológico , Cryptococcus neoformans/efeitos dos fármacos , Timol/farmacologia , Calcineurina/metabolismo , Criptococose/metabolismo , Cryptococcus neoformans/metabolismo , Ergosterol/farmacologia , Proteínas Fúngicas/metabolismo , Humanos , Proteínas Quinases Ativadas por Mitógeno/metabolismo , Monoterpenos/farmacologia , Transdução de Sinais/efeitos dos fármacos , Thymus (Planta)/química
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