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1.
J Chromatogr A ; 1627: 461397, 2020 Sep 13.
Artigo em Inglês | MEDLINE | ID: mdl-32823102

RESUMO

A new and sensitive analytical method for the simultaneous determination of secondary lipid peroxidation aldehydes has been successfully developed and validated. Malondialdehyde, acrolein, formaldehyde, acetaldehyde, propanal, and pentanal were extracted and derivatized using 2,4-dinitrophenylhydrazine (DNPH) by gas-diffusion microextraction (GDME) combined with dispersive liquid-liquid microextraction (DLLME) for gas chromatography-mass spectrometry (GC-MS) analysis. The experimental conditions have been optimized by experimental designs. The analytical method validation, in accordance to the Food and Drug Administration (FDA) guidance, provided good results in terms of linearity with r2≥0.9974, in the range from 0.15 or 0.3 µg·g-1 to 3 µg·g-1. Limits of detection and limits of quantification were 0.05 or 0.10 and 0.15 or 0.3 µg·g-1, respectively. Precision was tested as a relative standard deviation (RSD≤ 9.5%) and recoveries were between 95% and 110%. The method was applied in the characterization of aldehydes in forty-eight edible oil samples; with the highest concentration found in pomace olive oil for malondialdehyde at 6.64 µg·g-1.


Assuntos
Acetaldeído/análise , Acroleína/análise , Cromatografia Gasosa-Espectrometria de Massas/métodos , Microextração em Fase Líquida/métodos , Malondialdeído/análise , Óleos de Plantas/análise , Acetaldeído/isolamento & purificação , Acroleína/isolamento & purificação , Aldeídos/análise , Aldeídos/isolamento & purificação , Limite de Detecção , Peroxidação de Lipídeos , Malondialdeído/isolamento & purificação , Azeite de Oliva/análise , Reprodutibilidade dos Testes
2.
Toxicol Appl Pharmacol ; 371: 3-11, 2019 05 15.
Artigo em Inglês | MEDLINE | ID: mdl-30943385

RESUMO

Trans-4-methoxycinnamaldehyde (MCD) was isolated from the rhizomes of Etlingera pavieana (Pierre ex Gagnep.) R.M.Sm. MCD shows anti-inflammatory effects. However, the molecular mechanism underlying its anti-inflammatory action has not been described. In this study, we investigated this mechanism in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages and found MCD significantly inhibited nitric oxide (NO) and prostaglandin E2 (PGE2) production in a concentration-dependent manner. MCD could decrease LPS- and Pam3CSK4- induced the expressions of both iNOS and COX-2. The phosphorylation of inhibitory κB (IκB) and translocation of nuclear factor-κB (NF-κB) p65 subunit into the nucleus were also inhibited by MCD. Moreover, MCD suppressed LPS-induced phosphorylation of JNK except for ERK and p38 mitogen-activated protein kinases (MAPKs). Moreover, MCD significantly reduced ethyl phenylpropiolate-induced ear edema and carrageenan-induced paw edema in rat models. These findings indicated MCD has anti-inflammatory activity by inhibiting the production of NO and PGE2 by blocking NF-κB and JNK/c-Jun signaling pathways. Collectively, these data suggest that MCD could be developed as a novel therapeutic agent for inflammatory disorders.


Assuntos
Acroleína/análogos & derivados , Anti-Inflamatórios/farmacologia , Edema/prevenção & controle , Proteínas Quinases JNK Ativadas por Mitógeno/metabolismo , Ativação de Macrófagos/efeitos dos fármacos , Macrófagos/efeitos dos fármacos , NF-kappa B/metabolismo , Extratos Vegetais/farmacologia , Proteínas Proto-Oncogênicas c-jun/metabolismo , Zingiberaceae , Acroleína/isolamento & purificação , Acroleína/farmacologia , Alcinos , Animais , Anti-Inflamatórios/isolamento & purificação , Carragenina , Ciclo-Oxigenase 2/metabolismo , Modelos Animais de Doenças , Edema/induzido quimicamente , Edema/imunologia , Edema/metabolismo , Endotoxinas/farmacologia , Humanos , Macrófagos/enzimologia , Macrófagos/imunologia , Masculino , Camundongos , Óxido Nítrico Sintase Tipo II/metabolismo , Fosforilação , Extratos Vegetais/isolamento & purificação , Células RAW 264.7 , Ratos Sprague-Dawley , Rizoma , Transdução de Sinais , Zingiberaceae/química
3.
J Oleo Sci ; 67(5): 515-524, 2018.
Artigo em Inglês | MEDLINE | ID: mdl-29710039

RESUMO

Fish oil rich in docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) is known to have an unpleasant smell, even at low oxidation levels. Therefore, it is highly important to know the major volatiles formed during the early stages of fish oil oxidation. Comparative study with solid-phase microextraction (SPME) and static headspace (SHS) methods showed that 2-propenal (acrolein) was formed as the major volatile from the beginning of fish oil triacylglycerol (TAG) oxidation. The effectiveness of SPME extraction on each volatile was different from each fiber. Among the three different SPME fibers used in the present study, carboxen/polydimethylsiloxane (CAR/PDMS) was determined to be a better fiber for measuring the volatiles, including acrolein. The present study also showed that the non-selective SHS method is useful for determining the characteristic volatile formation in the early stages of fish oil TAG oxidation.


Assuntos
Acroleína/análise , Acroleína/isolamento & purificação , Óleos de Peixe/química , Compostos Orgânicos Voláteis/análise , Compostos Orgânicos Voláteis/isolamento & purificação , Dimetilpolisiloxanos , Oxirredução , Microextração em Fase Sólida/métodos , Triglicerídeos/química
4.
Molecules ; 23(5)2018 05 07.
Artigo em Inglês | MEDLINE | ID: mdl-29735955

RESUMO

The xanthine oxidase inhibitory activity and thermostability of Cinnamomum osmophloeum leaf oil microencapsulated with ß-cyclodextrin were evaluated in this study. The yield of leaf oil microcapsules was 86.3% using the optimal reaction conditions at the leaf oil to ß-cyclodextrin ratio of 15:85 and ethanol to water ratio ranging from 1:3 to 1:5. Based on the FTIR analysis, the characteristic absorption bands of major constituent, trans-cinnamaldehyde, were confirmed in the spectra of leaf oil microcapsules. According to the dry-heat aging test, ß-cyclodextrin was thermostable under the high temperature conditions, and it was beneficial to reduce the emission of C. osmophloeum leaf oil. Leaf oil microcapsules exhibited high xanthine oxidase inhibitory activity, with an IC50 value of 83.3 µg/mL. It is concluded that the lifetime of C. osmophloeum leaf oil can be effectively improved by microencapsulation, and leaf oil microcapsules possess superior xanthine oxidase inhibitory activity.


Assuntos
Acroleína/análogos & derivados , Cinnamomum/química , Supressores da Gota/química , Óleos de Plantas/química , Xantina Oxidase/antagonistas & inibidores , beta-Ciclodextrinas/química , Acroleína/química , Acroleína/isolamento & purificação , Cápsulas/síntese química , Composição de Medicamentos/métodos , Estabilidade de Medicamentos , Ensaios Enzimáticos , Supressores da Gota/isolamento & purificação , Temperatura Alta , Humanos , Folhas de Planta/química , Óleos de Plantas/isolamento & purificação , Xantina Oxidase/química
5.
Microb Pathog ; 116: 26-32, 2018 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-29325862

RESUMO

The objective of this study was to investigate the antibacterial effects of cinnamon (Cinnamomum zeylanicum) bark essential oil (CBEO) and its principal constituent cinnamaldehyde against Porphyromonas gingivalis and to elucidate the antibacterial mechanism. GC-MS analysis showed that cinnamaldehyde was the major constituent in CBEO (57.97%). The minimum inhibition concentrations (MICs) of CBEO and cinnamaldehyde were 6.25 µg/mL and 2.5 µM for P. gingivalis, respectively. Nucleic acid and protein leakage was observed with increasing concentrations of CBEO and cinnamaldehyde. Additionally, propidium iodide uptake assays revealed CBEO and cinnamaldehyde at 1 × MIC impaired P. gingivalis membrane integrity by enhancing cell permeability. Morphological changes in P. gingivalis cells were observed by scanning electron microscopy, which indicated cell membrane destruction. To further determine the anti-biofilm effect, relative biofilm formation and established biofilms were examined, which demonstrated that both CBEO and cinnamaldehyde at sub-MIC levels inhibited P. gingivalis biofilm formation by 74.5% and 67.3% separately, but only CBEO slightly decreased established biofilms by 33.5% at 4 × MIC. These results suggest the potential of CBEO as a natural antimicrobial agent against periodontal disease. Furthermore, cinnamaldehyde was confirmed to be the antibacterial substance of CBEO with inhibitory action against P. gingivalis.


Assuntos
Acroleína/análogos & derivados , Antibacterianos/farmacologia , Cinnamomum zeylanicum/química , Óleos Voláteis/farmacologia , Porphyromonas gingivalis/efeitos dos fármacos , Acroleína/isolamento & purificação , Acroleína/farmacologia , Antibacterianos/isolamento & purificação , Membrana Celular/efeitos dos fármacos , Membrana Celular/fisiologia , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Testes de Sensibilidade Microbiana , Microscopia Eletrônica de Varredura , Óleos Voláteis/isolamento & purificação , Permeabilidade/efeitos dos fármacos , Casca de Planta/química , Porphyromonas gingivalis/ultraestrutura
6.
Artigo em Inglês | MEDLINE | ID: mdl-29338637

RESUMO

Recent research has showed that Aspergillus flavus and Aspergillus parasiticus are aflatoxigenic species that can become very competitive in the framework of climate change. Aflatoxins show carcinogenic, mutagenic, immunotoxic and teratogenic effects on human and animals. Effective and sustainable measures to inhibit these species and aflatoxins in food are required. Origanum vulgare and Cinnamomum zeylanicum essential oils (EOs) and their major active constituents, carvacrol and cinnamaldehyde, respectively, were assayed for inhibiting these species and aflatoxin production in maize extract medium under different environmental conditions. Doses of 10-1000 mg l-1 were assayed and the effective doses for 50 (ED50) and 90% (ED90) growth inhibition were determined. The ED50 of cinnamaldehyde, carvacrol, oregano EO, and cinnamon EO against A. flavus were in the ranges 49-52.6, 98-145, 152-505, 295-560 mg l-1 and against A. parasiticus in the ranges 46-55.5, 101-175, 260-425 and 490-675 mg l-1, respectively, depending on environmental conditions. In A. flavus treatments ED90 were in the ranges 89.7-90.5, 770-860 and 820->1000 mg l-1 for cinnamaldehyde, carvacrol and cinnamon EO, and in A. parasiticus treatments in the ranges 89-91, 855->1000 and 900->1000 mg l-1, respectively. ED90 values for oregano EO against both species were >1000 mg l-1. Growth rates of both species were higher at 37 than at 25°C and at 0.99 than at 0.96 aw. Aflatoxin production was higher at 25 than at 37°C. Stimulation of aflatoxin production was observed at low doses except for cinnamaldehyde treatments. The effectiveness of EOs and their main constituents to inhibit fungal growth and aflatoxin production in contact assays was lower than in vapour phase assays using bioactive EVOH-EO films previously reported.


Assuntos
Aflatoxinas/biossíntese , Antifúngicos/farmacologia , Aspergillus/efeitos dos fármacos , Aspergillus/crescimento & desenvolvimento , Microbiologia de Alimentos , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Acroleína/análogos & derivados , Acroleína/química , Acroleína/isolamento & purificação , Acroleína/farmacologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Aspergillus/metabolismo , Cinnamomum zeylanicum/química , Cimenos , Testes de Sensibilidade Microbiana , Monoterpenos/química , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Origanum/química
7.
Zhongguo Zhong Yao Za Zhi ; 42(19): 3764-3769, 2017 Oct.
Artigo em Chinês | MEDLINE | ID: mdl-29235293

RESUMO

The present work is to study the chemical constituents from petroleum ether fraction of Tibetan medicine Swertia chirayita by column chromatography and recrystallization. The structures were identified by physical and chemical properties and spectral data as swerchirin (1), decussatin (2), 1,8-dihydroxy-3,5,7-trimethoxyxanthone (3), 1-hydroxy-3,5,7,8-tetramethoxyxanthone (4), bellidifolin (5), 1-hydroxy-3, 7-dimethoxyxanthone (6), methylswertianin (7), 1-hydroxy-3,5-dimethoxyxanthone (8), erythrodiol (9), oleanolic acid (10), gnetiolactone (11), scopoletin (12), sinapaldehyde (13), syringaldehyde (14), and ß-sitosterol (15). Compounds 3, 4, 9, 11-14 were isolated from S. chirayita for the first time. Compounds 9 and 12 were firstly isolated from the genus Swertia. The cytotoxic activities of compounds 1, 2, 5, 7 and 8 against human pancreatic cancer cell lines SW1990 and BxPC-3,and the protective effects of these compounds against hydrogen peroxide (H2O2)-induced oxidative stress in human endothelium-derived EA.hy926 were investigated in vitro. The results showed no obvious effect at the high concentration of 50 µmol•L⁻¹.


Assuntos
Medicamentos de Ervas Chinesas/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química , Swertia/química , Acroleína/análogos & derivados , Acroleína/isolamento & purificação , Alcanos , Benzaldeídos/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Peróxido de Hidrogênio , Ácido Oleanólico/isolamento & purificação , Estresse Oxidativo/efeitos dos fármacos , Escopoletina/isolamento & purificação , Sitosteroides/isolamento & purificação , Xantonas/isolamento & purificação
8.
Regul Toxicol Pharmacol ; 86: 117-127, 2017 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-28238852

RESUMO

Carbonyls are harmful and potentially harmful constituents (HPHCs) in mainstream cigarette smoke (MSS). Carbonyls, including formaldehyde and acrolein, are carcinogenic or mutagenic in a dose-dependent manner. Past studies demonstrate significant reduction of HPHCs by charcoal filtration. However, limits of charcoal filtration and cigarette design have not yet been investigated in a systematic manner. Objective data is needed concerning the feasibility of HPHC reduction in combustible filtered cigarettes. This systematic study evaluates the effect of charcoal filtration on carbonyl reduction in MSS. We modified filters of ten popular cigarette products with predetermined quantities (100-400 mg) of charcoal in a plug-space-plug configuration. MSS carbonyls, as well as total particulate matter, tar, nicotine, carbon monoxide (TNCO), and draw resistance were quantified. Significant carbonyl reductions were observed across all cigarette products as charcoal loading increased. At the highest charcoal loadings, carbonyls were reduced by nearly 99%. Tar and nicotine decreased modestly (<20%) compared to reductions in carbonyls. Increased draw resistance was significant at only the highest charcoal loadings. This work addresses information gaps in the science base that can inform the evaluation of charcoal filtration as an available technological adaptation to cigarette design which reduces levels of carbonyls in MSS.


Assuntos
Carcinógenos/isolamento & purificação , Carvão Vegetal , Filtração/instrumentação , Mutagênicos/isolamento & purificação , Nicotiana/química , Fumaça , Produtos do Tabaco , Acroleína/isolamento & purificação , Acroleína/toxicidade , Formaldeído/isolamento & purificação , Formaldeído/toxicidade , Nicotina/análise
9.
Environ Toxicol Pharmacol ; 48: 85-93, 2016 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-27770660

RESUMO

Coniferaldehyde (CA) exerts anti-inflammatory properties by inducing heme oxygenase-1 (HO-1). To define the regulation mechanism by which CA induces a cytoprotective function and HO-1 expression, the up-stream regulations involved in the activation of nuclear transcription factor-erythroid 2-related factor (Nrf)-2/HO-1 pathway were investigated. CA dramatically increased the Nrf-2 nuclear translocation and HO-1 expression. Lipopolysaccharide (LPS)-induced expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2, and cell death were down-regulated by CA, which were reversed by inhibition of HO-1 activity. Furthermore, CA specifically enhanced the phosphorylation of protein kinase C (PKC) α/ß II. Selective inhibition of PKC α/ß II using Go6976 or siRNA abolished the CA-induced Nrf-2/HO-1 signaling, and consequently suppressed the cytoprotective activity of CA on the LPS-induced cell death. Together, our results elucidate the regulatory mechanism of PKC α/ß II as the upstream molecule of Nrf-2 required for HO-1 expression during CA-induced anti-inflammatory cytoprotective function in LPS stimulated macrophages.


Assuntos
Acroleína/análogos & derivados , Anti-Inflamatórios/farmacologia , Apoptose/efeitos dos fármacos , Heme Oxigenase-1/metabolismo , Macrófagos/efeitos dos fármacos , Proteínas de Membrana/metabolismo , Fator 2 Relacionado a NF-E2/metabolismo , Proteína Quinase C/metabolismo , Acroleína/isolamento & purificação , Acroleína/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Técnicas de Cultura de Células , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Lipopolissacarídeos , Macrófagos/metabolismo , Macrófagos/patologia , Camundongos , Fosforilação , Proteína Quinase C beta/metabolismo , Proteína Quinase C-alfa/metabolismo , Transdução de Sinais/efeitos dos fármacos , Vitex/química
10.
Eur J Pharmacol ; 788: 65-74, 2016 Oct 05.
Artigo em Inglês | MEDLINE | ID: mdl-27316792

RESUMO

Dalbergia sissoo Roxb. is a well known medicinal plant of India, enriched with various flavonoids used for treating multiple diseases. Earlier, we have shown that extract of Dalbergia sissoo Roxb. leaves mitigate ovariectomy induced bone loss and pure compounds (neoflavonoids) isolated from it, promote osteoblastogenesis in primary calvarial osteoblasts cells in vitro. Here, we hypothesize that dalsissooal (DSL), a novel neoflavonoid isolated from the heartwood of Dalbergia sissoo Roxb. is an important constituent of the extract that imparts bone forming effects. Treatment with DSL enhanced trabecular bone micro-architecture parameters, biomechanical strength, increased bone formation rate and mineral apposition rate in OVx mice comparable to 17ß-estradiol. It increased bone formation by enhancing osteoblast gene expression and reduced bone turnover by decreasing osteoclastic gene expressions. Interestingly, we observed that DSL has no uterine estrogenic effects. At cellular levels, DSL promoted differentiation of bone marrow cells as well as calvaria osteoblast cells towards osteoblast lineage by enhancing differentiation and mineralizing ability to form mineralizing nodules via stimulating BMP-2 and RunX-2 expressions. Overall, our data suggest that oral supplementation of a novel neoflavonoid dalsissooal isolated from heartwood of Dalbergia sissoo Roxb. exhibited bone anabolic action by improving structural property of bone, promoting new bone formation and reducing bone turnover rate in post-menopausal model for osteoporosis with no uterine hyperplasia.


Assuntos
Acroleína/análogos & derivados , Dalbergia/química , Flavonoides/farmacologia , Osteogênese/efeitos dos fármacos , Osteoporose/fisiopatologia , Fenóis/farmacologia , Acroleína/isolamento & purificação , Acroleína/farmacologia , Animais , Calcificação Fisiológica/efeitos dos fármacos , Osso Esponjoso/efeitos dos fármacos , Osso Esponjoso/patologia , Osso Esponjoso/fisiopatologia , Diferenciação Celular/efeitos dos fármacos , Modelos Animais de Doenças , Relação Dose-Resposta a Droga , Estrogênios/deficiência , Feminino , Flavonoides/isolamento & purificação , Regulação da Expressão Gênica/efeitos dos fármacos , Camundongos , Osteoblastos/efeitos dos fármacos , Osteoblastos/patologia , Osteocalcina/sangue , Osteoporose/metabolismo , Osteoporose/patologia , Ovariectomia , Fenóis/isolamento & purificação , Folhas de Planta/química , Útero/efeitos dos fármacos , Útero/metabolismo
11.
Drug Des Devel Ther ; 10: 141-53, 2016.
Artigo em Inglês | MEDLINE | ID: mdl-26792981

RESUMO

Cinnamomum verum is used to make the spice cinnamon and has been used as a traditional Chinese herbal medicine for various applications. We evaluated the anticancer effect of 2-methoxycinnamaldehyde (2-MCA), a constituent of the bark of the plant, and its underlying molecular biomarkers associated with carcinogenesis in human hepatocellular carcinoma SK-Hep-1 cell line. The results show that 2-MCA suppressed proliferation and induced apoptosis as indicated by mitochondrial membrane potential loss, activation of caspase-3 and caspase-9, increase in the DNA content in sub-G1, and morphological characteristics of apoptosis, including blebbing of plasma membrane, nuclear condensation, fragmentation, apoptotic body formation, and long comet tail. In addition, 2-MCA also induced lysosomal vacuolation with increased volume of acidic compartments, suppressions of nuclear transcription factors NF-κB, cyclooxygenase-2, prostaglandin E2 (PGE2), and both topoisomerase I and II activities in a dose-dependent manner. Further study reveals the growth-inhibitory effect of 2-MCA was also evident in a nude mice model. Taken together, the data suggest that the growth-inhibitory effect of 2-MCA against SK-Hep-1 cells is accompanied by downregulations of NF-κB-binding activity, inflammatory responses involving cyclooxygenase-2 and PGE2, and proliferative control involving apoptosis, both topoisomerase I and II activities, together with an upregulation of lysosomal vacuolation and volume of acidic compartments. Similar effects (including all of the above-mentioned effects) were found in other tested cell lines, including human hepatocellular carcinoma Hep 3B, lung adenocarcinoma A549, squamous cell carcinoma NCI-H520, colorectal adenocarcinoma COLO 205, and T-lymphoblastic MOLT-3 (results not shown). Our data suggest that 2-MCA could be a potential agent for anticancer therapy.


Assuntos
Acroleína/análogos & derivados , Carcinoma Hepatocelular/tratamento farmacológico , Cinnamomum zeylanicum/química , Neoplasias Hepáticas/tratamento farmacológico , Acroleína/isolamento & purificação , Acroleína/farmacologia , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Apoptose/efeitos dos fármacos , Carcinoma Hepatocelular/patologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , DNA Topoisomerases Tipo I/efeitos dos fármacos , DNA Topoisomerases Tipo II/efeitos dos fármacos , Relação Dose-Resposta a Droga , Humanos , Neoplasias Hepáticas/patologia , Masculino , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Camundongos , Camundongos Endogâmicos BALB C , Camundongos Nus , Ensaios Antitumorais Modelo de Xenoenxerto
12.
J Drug Target ; 24(7): 624-34, 2016 08.
Artigo em Inglês | MEDLINE | ID: mdl-26707867

RESUMO

Cinnamomum verum has been used as a traditional Chinese herbal medicine. We evaluated the anticancer effect of 2-methoxycinnamaldehyde (2-MCA), a constituent of the bark of the plant, in hepatocellular carcinoma Hep 3B cells. The results show that 2-MCA suppressed proliferation and induced apoptosis as indicated by an up-regulation of pro-apoptotic bax and bak genes and down-regulation of anti-apoptotic bcl-2 and bcl-XL genes, mitochondrial membrane potential loss, cytochrome c release, activation of caspase 3 and 9, increase in the DNA content in sub G1, and morphological characteristics of apoptosis. 2-MCA also induced lysosomal vacuolation with increased volume of acidic compartments (VAC), suppressions of nuclear transcription factors NF-κB, cyclooxygenase-2 (COX-2), prostaglandin E2 (PGE2), and both topoisomerase I and II activities in a dose-dependent manner. Further study reveals the growth-inhibitory effect of 2-MCA was also evident in a nude mice model. Taken together, the data suggest that the growth-inhibitory effect of 2-MCA against Hep 3B cells is accompanied by downregulations of NF-κB binding activity, inflammatory responses involving COX-2 and PGE2, and proliferative control involving apoptosis, both topoisomerase I and II activities, together with an upregulation of lysosomal vacuolation and VAC. Our data suggest that 2-MCA could be a potential agent for anticancer therapy.


Assuntos
Acroleína/análogos & derivados , Antineoplásicos Fitogênicos/farmacologia , Cinnamomum zeylanicum/química , Inibidores da Topoisomerase I/farmacologia , Inibidores da Topoisomerase II/farmacologia , Acroleína/isolamento & purificação , Acroleína/farmacologia , Acroleína/uso terapêutico , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/uso terapêutico , Apoptose/efeitos dos fármacos , Carcinoma Hepatocelular/enzimologia , Carcinoma Hepatocelular/patologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Descoberta de Drogas , Humanos , Neoplasias Hepáticas/enzimologia , Neoplasias Hepáticas/patologia , Masculino , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Camundongos Nus , Casca de Planta/química , Inibidores da Topoisomerase I/isolamento & purificação , Inibidores da Topoisomerase I/uso terapêutico , Inibidores da Topoisomerase II/isolamento & purificação , Inibidores da Topoisomerase II/uso terapêutico , Ensaios Antitumorais Modelo de Xenoenxerto
13.
J Oleo Sci ; 64(8): 825-33, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-26179003

RESUMO

The chemical composition of essential oil extracted from Uncaria Hook ("Chotoko" in Japanese), the branch with curved hook of the herbal medicine Uncaria rhynchophylla has been investigated by GC and GC-MS analyses. Eighty-four compounds, representing 90.8% of the total content was identified in oil obtained from Uncaria Hook. The main components i were (E)-cinnamaldehyde (13.4%), α-copaene (8.0%), methyl eugenol (6.8%), δ-cadinene (5.3%), and curcumene (3.6%). The important key aroma-active compounds in the oil were detected by gas chromatography-olfactometry (GC-O) and aroma extract dilution analysis (AEDA), using the flavor dilution (FD) factor to express the odor potency of each compounds. Furthermore, the odor activity value (OAV) has been used as a measure of the relative contribution of each compound to the aroma of the Uncaria Hook oil. The GC-O and AEDA results showed that α-copaene (FD = 4, OAV = 4376), (E)-linalool oxide (FD = 64, OAV = 9.1), and methyl eugenol (FD = 64, OAV = 29) contributed to the woody and spicy odor of Uncaria Hook oil, whereas furfural (FD = 8, OAV = 4808) contributed to its sweet odor. These results warrant further investigations of the application of essential oil from Uncaria Hook in the phytochemical and medicinal fields.


Assuntos
Acroleína/análogos & derivados , Cromatografia Gasosa/métodos , Eugenol/análogos & derivados , Cromatografia Gasosa-Espectrometria de Massas/métodos , Óleos Voláteis/química , Olfatometria/métodos , Óleos de Plantas/química , Sesquiterpenos/isolamento & purificação , Uncaria/química , Acroleína/análise , Acroleína/isolamento & purificação , Monoterpenos Acíclicos , Cicloexanóis/análise , Cicloexanóis/isolamento & purificação , Eugenol/análise , Eugenol/isolamento & purificação , Furaldeído/análise , Furaldeído/isolamento & purificação , Monoterpenos/análise , Monoterpenos/isolamento & purificação , Sesquiterpenos/análise , Compostos de Tritil/análise , Compostos de Tritil/isolamento & purificação
14.
Food Funct ; 6(3): 910-9, 2015 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-25629927

RESUMO

Chronic inflammation is a contributing factor in many age-related diseases. In a previous study, we have shown that Sri Lankan cinnamon (C. zeylanicum) was one of the most potent anti-inflammatory foods out of 115 foods tested. However, knowledge about the exact nature of the anti-inflammatory compounds and their distribution in the two major cinnamon species used for human consumption is limited. The aim of this investigation was to determine the anti-inflammatory activity of C. zeylanicum and C. cassia and elucidate their main phytochemical compounds. When extracts were tested in LPS and IFN-γ activated RAW 264.7 macrophages, most of the anti-inflammatory activity, measured by down-regulation of nitric oxide and TNF-α production, was observed in the organic extracts. The most abundant compounds in these extracts were E-cinnamaldehyde and o-methoxycinnamaldehyde. The highest concentration of E-cinnamaldehyde was found in the DCM extract of C. zeylanicum or C. cassia (31 and 34 mg g(-1) of cinnamon, respectively). When these and other constituents were tested for their anti-inflammatory activity in RAW 264.7 and J774A.1 macrophages, the most potent compounds were E-cinnamaldehyde and o-methoxycinnamaldehyde, which exhibited IC50 values for NO with RAW 264.7 cells of 55 ± 9 µM (7.3 ± 1.2 µg mL(-1)) and 35 ± 9 µM (5.7 ± 1.5 µg mL(-1)), respectively; and IC50 values for TNF-α of 63 ± 9 µM (8.3 ± 1.2 µg mL(-1)) and 78 ± 16 µM (12.6 ± 2.6 µg mL(-1)), respectively. If therapeutic concentrations can be achieved in target tissues, cinnamon and its components may be useful in the treatment of age-related inflammatory conditions.


Assuntos
Acroleína/análogos & derivados , Anti-Inflamatórios não Esteroides/isolamento & purificação , Cinnamomum aromaticum/química , Cinnamomum zeylanicum/química , Suplementos Nutricionais , Macrófagos/metabolismo , Acroleína/análise , Acroleína/química , Acroleína/isolamento & purificação , Acroleína/metabolismo , Animais , Anti-Inflamatórios não Esteroides/análise , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/metabolismo , Linhagem Celular , Cinnamomum aromaticum/crescimento & desenvolvimento , Suplementos Nutricionais/análise , Etnofarmacologia , Ativação de Macrófagos , Macrófagos/imunologia , Medicina Tradicional , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/metabolismo , Casca de Planta/química , Casca de Planta/crescimento & desenvolvimento , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/metabolismo , Sri Lanka , Estereoisomerismo , Fator de Necrose Tumoral alfa/antagonistas & inibidores , Fator de Necrose Tumoral alfa/metabolismo
16.
J Agric Food Chem ; 60(51): 12491-500, 2012 Dec 26.
Artigo em Inglês | MEDLINE | ID: mdl-23199195

RESUMO

Whiskey includes many nonvolatile substances (whiskey congeners; Whc) that seep from the oak cask during the maturation process. To date, many functions of Whc have reported, such as antiallergy and antimelanogenesis. This study examined the effect of Whc on LPS/IFNγ-induced nitric oxide (NO) production in murine macrophage RAW 264 cells. Whc suppressed LPS/IFNγ-induced NO production in a concentration-dependent manner. To determine the active compounds in Whc, the effect of 10 major compounds isolated from Whc on LPS/IFNγ-induced NO production was examined. Coniferylaldehyde (CA) and sinapylaldehyde (SiA) strongly suppressed LPS/IFNγ-induced NO production. Pretreatment with Whc, CA, and SiA induced heme oxygenase-1 (HO-1) expression. The expression of HO-1 by Whc, CA, and SiA pretreatment was due to activation of Nrf2/ARE signaling via the elevation of intracellular reactive oxygen species. To investigate the in vivo effects of Whc, Whc was administered to mice with antitype II collagen antibody-induced arthritis, and we the arthritis score and hind paw volume were measured. Administration of Whc remarkably suppressed the arthritis score and hind paw volume. Taken together, these findings suggest that Whc is beneficial for the treatment of inflammatory disease.


Assuntos
Bebidas Alcoólicas/análise , Heme Oxigenase-1/genética , Interferon gama/farmacologia , Lipopolissacarídeos/farmacologia , Macrófagos/enzimologia , Óxido Nítrico/biossíntese , Acroleína/análogos & derivados , Acroleína/isolamento & purificação , Acroleína/farmacologia , Aldeídos/isolamento & purificação , Aldeídos/farmacologia , Animais , Anticorpos Monoclonais , Artrite Experimental/etiologia , Artrite Experimental/prevenção & controle , Linhagem Celular , Colágeno Tipo II/imunologia , Indução Enzimática/efeitos dos fármacos , Heme Oxigenase-1/biossíntese , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Óxido Nítrico/antagonistas & inibidores
17.
J Ethnopharmacol ; 139(2): 605-15, 2012 Jan 31.
Artigo em Inglês | MEDLINE | ID: mdl-22179023

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Cinnamomum cassia Blume has been used as a traditional Chinese herbal medicine for alleviation of fever, inflammation, chronic bronchitis, and to improve blood circulation. AIM OF THE STUDY: We addressed whether 2-methoxycinnamaldehyde (2-MCA), one of active ingredients of Cinnamomum cassia, reduces vascular cell adhesion molecule-1 (VCAM-1) expression in tumor necrosis factor-alpha (TNF-α)-activated endothelial cells and protects ischemia/reperfusion (I/R)-injury due to heme oxygenase (HO)-1 induction. MATERIALS AND METHODS: Adult male rats were subjected to 30 min of ischemia by occlusion of the left anterior descending coronary artery followed by 24h of reperfusion. Rats were randomized to receive vehicle or 2-MCA (i.v.) 10 min before reperfusion. RESULTS: Administration of 2-MCA significantly improved I/R-induced myocardial dysfunction by increasing the values of the first derivative (±dp/dt) of left ventricular pressure and decreased infarct size. In addition, 2-MCA reduced the expression of high mobility group box 1 (HMGB1), an activator of the inflammatory cascade when released into the extracellular space, and VCAM-1 in I/R myocardium along with increase of HO-1 induction. The reduced injury was accompanied by significantly reduction of neutrophils infiltration and increased SOD activity in ischemic tissues and reduced serum level of cardiac troponin I (cTnI). Furthermore, 2-MCA significantly increased HO-1 induction by translocation of Nrf-2 from cytosol to nucleus in endothelial cells. Inhibition of VCAM-1 expression by 2-MCA was reversed both by SnPPIX, a HO-1 inhibitor and siHO-1 RNA trasfection in TNF-α-activated cells. In addition, 2-MCA significantly inhibited NF-κB luciferase activity in TNF-α-activated endothelial cells. As expected, 2-MCA significantly inhibited monocyte (U937) adhesion to endothelial cells. CONCLUSION: We concluded that 2-MCA protects of myocardial I/R-injury due to antioxidant and anti-inflammatory action possibly by HO-1 induction which can be explained why Cinnamomum cassia has been used in inflammatory disorders.


Assuntos
Acroleína/análogos & derivados , Cardiotônicos/farmacologia , Cinnamomum aromaticum , Heme Oxigenase (Desciclizante)/biossíntese , Infarto do Miocárdio/prevenção & controle , Traumatismo por Reperfusão Miocárdica/prevenção & controle , Miocárdio/enzimologia , Extratos Vegetais/farmacologia , Acroleína/isolamento & purificação , Acroleína/farmacologia , Animais , Anti-Inflamatórios/farmacologia , Antioxidantes/farmacologia , Cardiotônicos/isolamento & purificação , Cinnamomum aromaticum/química , Técnicas de Cocultura , Modelos Animais de Doenças , Relação Dose-Resposta a Droga , Indução Enzimática , Inibidores Enzimáticos/farmacologia , Proteína HMGB1/metabolismo , Heme Oxigenase (Desciclizante)/antagonistas & inibidores , Heme Oxigenase (Desciclizante)/genética , Heme Oxigenase-1/biossíntese , Hemodinâmica/efeitos dos fármacos , Células Endoteliais da Veia Umbilical Humana/efeitos dos fármacos , Células Endoteliais da Veia Umbilical Humana/enzimologia , Células Endoteliais da Veia Umbilical Humana/imunologia , Humanos , Masculino , Infarto do Miocárdio/enzimologia , Infarto do Miocárdio/patologia , Infarto do Miocárdio/fisiopatologia , Traumatismo por Reperfusão Miocárdica/enzimologia , Traumatismo por Reperfusão Miocárdica/patologia , Traumatismo por Reperfusão Miocárdica/fisiopatologia , Miocárdio/patologia , NF-kappa B/genética , NF-kappa B/metabolismo , Infiltração de Neutrófilos/efeitos dos fármacos , Estresse Oxidativo/efeitos dos fármacos , Extratos Vegetais/isolamento & purificação , Plantas Medicinais , Interferência de RNA , Ratos , Ratos Sprague-Dawley , Superóxido Dismutase/metabolismo , Fatores de Tempo , Transfecção , Troponina I/metabolismo , Fator de Necrose Tumoral alfa/metabolismo , Células U937 , Molécula 1 de Adesão de Célula Vascular/metabolismo , Função Ventricular Esquerda/efeitos dos fármacos , Pressão Ventricular/efeitos dos fármacos
18.
Phytother Res ; 25(10): 1511-8, 2011 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-21394803

RESUMO

The purpose of this study was to analyse the major compound in the leaf essential oil of Cinnamomum osmophloeum Kaneh. and to examine its in vivo toxicity and cytokine-modulatory effects. The HS-GC/MS and quantitative HPLC analyses showed the concentrations of the major compounds, cinnamaldehyde, benzaldehyde and 3-phenylpropionaldehyde, in the leaf essential oil of Cinnamomum osmophloeum to be 16.88, 1.28 and 1.70 mg/mL, respectively. Acute and sub-acute toxicity tests identified no significant changes in body weight, liver and kidney function indices, and pathology for the mice treated with up to 1 mL/kg body weight of Cinnamomum osmophloeum leaf essential oil or up to 4 mg/kg body weight of cinnamaldehyde. A murine model was established using ovalbumin (OVA)-primed Balb/C mice treated with various concentrations of Cinnamomum osmophloeum leaf essential oil or cinnamaldehyde daily for 4 weeks. The results of tests with commercial ELISA kits indicated no significant cytokine-modulatory effects in mice treated with Cinnamomum osmophloeum leaf essential oil; however, the serum concentrations of IL-2, IL-4 and IL-10, but not IFN-γ, significantly increased in animals treated with 1 mg/kg body weight of cinnamaldehyde during the 4-week period. The possibility that the other constituents act as antagonists of cinnamaldehyde cannot be excluded.


Assuntos
Acroleína/análogos & derivados , Cinnamomum/química , Citocinas/sangue , Fatores Imunológicos/farmacologia , Óleos Voláteis/química , Extratos Vegetais/farmacologia , Acroleína/química , Acroleína/isolamento & purificação , Acroleína/farmacologia , Aldeídos/análise , Aldeídos/farmacologia , Animais , Benzaldeídos/análise , Benzaldeídos/farmacologia , Feminino , Fatores Imunológicos/química , Fatores Imunológicos/isolamento & purificação , Camundongos , Camundongos Endogâmicos BALB C , Modelos Animais , Óleos Voláteis/isolamento & purificação , Ovalbumina , Extratos Vegetais/química , Folhas de Planta/química
19.
Fitoterapia ; 81(4): 289-95, 2010 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-19825398

RESUMO

Here we investigated the anti-inflammatory properties of Ocotea quixos essential oil and of its main components, trans-cinnamaldehyde and methyl cinnamate, in in vitro and in vivo models. Ocotea essential oil and trans-cinnamaldehyde but not methyl cinnamate significantly reduced LPS-induced NO release from J774 macrophages at non-toxic concentrations, inhibited LPS-induced COX-2 expression and increased forskolin-induced cAMP production. The essential oil (30-100mg/kg os) and trans-cinnamaldehyde (10mg/kg os) in carrageenan-induced rat paw edema showed anti-inflammatory effect without damaging gastric mucosa. In conclusion we provide the first evidence of a significant anti-inflammatory gastro-sparing activity of O.quixos essential oil.


Assuntos
Acroleína/análogos & derivados , Anti-Inflamatórios/uso terapêutico , Edema/tratamento farmacológico , Mediadores da Inflamação/metabolismo , Ocotea/química , Óleos Voláteis/uso terapêutico , Extratos Vegetais/uso terapêutico , Acroleína/isolamento & purificação , Acroleína/farmacologia , Acroleína/uso terapêutico , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/uso terapêutico , Carragenina , Linhagem Celular Tumoral , Cinamatos , Edema/induzido quimicamente , Mucosa Gástrica/efeitos dos fármacos , Humanos , Lipopolissacarídeos , Macrófagos/efeitos dos fármacos , Masculino , Neuroblastoma/tratamento farmacológico , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Fitoterapia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Ratos , Ratos Wistar
20.
Nutr Cancer ; 61(5): 723-34, 2009.
Artigo em Inglês | MEDLINE | ID: mdl-19838947

RESUMO

Cinnamaldehydes have been reported to induce apoptosis in human carcinomas through the generation of reactive oxygen species (ROS). 2'-benzoyloxycinnamaldehyde (BCA) has been reported to inhibit tumor formation in H-ras12V transgenic mice. To see the antitumor effects of BCA, BCA was administrated intraperitoneally (50 mg/kg) to H-ras12V transgenic mice for 3 wk, and it was found that the hepatic tumor volume and the total number of tumors were decreased in BCA-treated mice as compared to control H-ras12V transgenic mice. To identify possible target genes responsible for BCA antitumor effects in H-ras12V transgenic mice, cDNA microarray analyses were performed comparing gene expression between BCA treated and control transgenic mice. We found that 42 genes were downregulated, and 40 genes were upregulated in the BCA-treated transgenic mice. The downregulated genes included several genes involved in ROS regulation and immune response (aconitase, metallothionein-1, metallothionein-2, and purine nucleoside phosphorylase). The expression of ROS-related genes, metallothionein 1 and metallothionein 2, was decreased more than twofold with BCA treatment (P < 0.001). It was confirmed by RT-PCR and immunohistochemical analyses. The inhibition of tumor formation and growth in H-ras12V transgenic mice by BCA was mediated through inhibition of the expression of the ROS scavengers metallothionein 1 and metallothionein 2.


Assuntos
Acroleína/análogos & derivados , Antineoplásicos/administração & dosagem , Benzoatos/administração & dosagem , Neoplasias Hepáticas Experimentais/prevenção & controle , Metalotioneína/genética , Acroleína/administração & dosagem , Acroleína/isolamento & purificação , Animais , Antineoplásicos/isolamento & purificação , Benzoatos/isolamento & purificação , Linhagem Celular Tumoral , Regulação para Baixo , Perfilação da Expressão Gênica , Regulação Neoplásica da Expressão Gênica , Células Hep G2 , Humanos , Neoplasias Hepáticas Experimentais/patologia , Masculino , Metalotioneína/metabolismo , Camundongos , Camundongos Transgênicos , Análise de Sequência com Séries de Oligonucleotídeos , Componentes Aéreos da Planta/química , Polygonaceae/química , Isoformas de Proteínas/genética , Isoformas de Proteínas/metabolismo , RNA Mensageiro/metabolismo , Carga Tumoral , Proteínas ras/genética
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