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1.
Prep Biochem Biotechnol ; 51(9): 833-841, 2021.
Artículo en Inglés | MEDLINE | ID: mdl-33427036

RESUMEN

Cinnamaldehyde (CA) is one of the major active pharmaceutical ingredient of cinnamon bark. Hydrodistillation (HD) is usually used in CA extraction, however, the extraction yield is lower. The cell wall is a key factor limiting the extraction of essential oils. In-situ reactive heat breaking cell wall (RHB) could destroy the cell wall, which was conducive to the diffusion of CA. The aim of this work was to examine the effect of RHB pretreatment to HD extraction. Response surface methodology (RSM) was used to optimize RHB pretreatment parameters, and Box-Behnken Design (BBD) method was performed to evaluate the effects of different operating parameters. The maximum yield was increased to 3.31 ± 0.11% (w/w) from 2.08 ± 0.042% (w/w) after RSM optimization. Scanning electron microscopic (SEM) analysis showed that RHB destroyed and disrupted the cell wall of cinnamon bark. The GC analysis demonstrated that the purity of cinnamaldehyde was improved and no new components were presented in the extraction product from the cinnamon via RHB pretreatment. In conclusion, RHB is an effective pretreatment method for the CA extraction, and also may be used in the other herbal medicine extraction.


Asunto(s)
Pared Celular/química , Cinnamomum zeylanicum/química , Calor , Óxidos de Azufre/química , Acroleína/análogos & derivados , Acroleína/química , Acroleína/aislamiento & purificación
2.
J Chromatogr A ; 1627: 461397, 2020 Sep 13.
Artículo en Inglés | MEDLINE | ID: mdl-32823102

RESUMEN

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.


Asunto(s)
Acetaldehído/análisis , Acroleína/análisis , Cromatografía de Gases y Espectrometría de Masas/métodos , Microextracción en Fase Líquida/métodos , Malondialdehído/análisis , Aceites de Plantas/análisis , Acetaldehído/aislamiento & purificación , Acroleína/aislamiento & purificación , Aldehídos/análisis , Aldehídos/aislamiento & purificación , Límite de Detección , Peroxidación de Lípido , Malondialdehído/aislamiento & purificación , Aceite de Oliva/análisis , Reproducibilidad de los Resultados
3.
Toxicol Appl Pharmacol ; 371: 3-11, 2019 05 15.
Artículo en Inglés | MEDLINE | ID: mdl-30943385

RESUMEN

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.


Asunto(s)
Acroleína/análogos & derivados , Antiinflamatorios/farmacología , Edema/prevención & control , Proteínas Quinasas JNK Activadas por Mitógenos/metabolismo , Activación de Macrófagos/efectos de los fármacos , Macrófagos/efectos de los fármacos , FN-kappa B/metabolismo , Extractos Vegetales/farmacología , Proteínas Proto-Oncogénicas c-jun/metabolismo , Zingiberaceae , Acroleína/aislamiento & purificación , Acroleína/farmacología , Alquinos , Animales , Antiinflamatorios/aislamiento & purificación , Carragenina , Ciclooxigenasa 2/metabolismo , Modelos Animales de Enfermedad , Edema/inducido químicamente , Edema/inmunología , Edema/metabolismo , Endotoxinas/farmacología , Humanos , Macrófagos/enzimología , Macrófagos/inmunología , Masculino , Ratones , Óxido Nítrico Sintasa de Tipo II/metabolismo , Fosforilación , Extractos Vegetales/aislamiento & purificación , Células RAW 264.7 , Ratas Sprague-Dawley , Rizoma , Transducción de Señal , Zingiberaceae/química
4.
Molecules ; 23(5)2018 05 07.
Artículo en Inglés | MEDLINE | ID: mdl-29735955

RESUMEN

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.


Asunto(s)
Acroleína/análogos & derivados , Cinnamomum/química , Supresores de la Gota/química , Aceites de Plantas/química , Xantina Oxidasa/antagonistas & inhibidores , beta-Ciclodextrinas/química , Acroleína/química , Acroleína/aislamiento & purificación , Cápsulas/síntesis química , Composición de Medicamentos/métodos , Estabilidad de Medicamentos , Pruebas de Enzimas , Supresores de la Gota/aislamiento & purificación , Calor , Humanos , Hojas de la Planta/química , Aceites de Plantas/aislamiento & purificación , Xantina Oxidasa/química
5.
Zhongguo Zhong Yao Za Zhi ; 42(19): 3764-3769, 2017 Oct.
Artículo en Chino | MEDLINE | ID: mdl-29235293

RESUMEN

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.


Asunto(s)
Medicamentos Herbarios Chinos/química , Fitoquímicos/aislamiento & purificación , Extractos Vegetales/química , Swertia/química , Acroleína/análogos & derivados , Acroleína/aislamiento & purificación , Alcanos , Benzaldehídos/aislamiento & purificación , Línea Celular Tumoral , Humanos , Peróxido de Hidrógeno , Ácido Oleanólico/aislamiento & purificación , Estrés Oxidativo/efectos de los fármacos , Escopoletina/aislamiento & purificación , Sitoesteroles/aislamiento & purificación , Xantonas/aislamiento & purificación
6.
Eur J Pharmacol ; 788: 65-74, 2016 Oct 05.
Artículo en Inglés | MEDLINE | ID: mdl-27316792

RESUMEN

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.


Asunto(s)
Acroleína/análogos & derivados , Dalbergia/química , Flavonoides/farmacología , Osteogénesis/efectos de los fármacos , Osteoporosis/fisiopatología , Fenoles/farmacología , Acroleína/aislamiento & purificación , Acroleína/farmacología , Animales , Calcificación Fisiológica/efectos de los fármacos , Hueso Esponjoso/efectos de los fármacos , Hueso Esponjoso/patología , Hueso Esponjoso/fisiopatología , Diferenciación Celular/efectos de los fármacos , Modelos Animales de Enfermedad , Relación Dosis-Respuesta a Droga , Estrógenos/deficiencia , Femenino , Flavonoides/aislamiento & purificación , Regulación de la Expresión Génica/efectos de los fármacos , Ratones , Osteoblastos/efectos de los fármacos , Osteoblastos/patología , Osteocalcina/sangre , Osteoporosis/metabolismo , Osteoporosis/patología , Ovariectomía , Fenoles/aislamiento & purificación , Hojas de la Planta/química , Útero/efectos de los fármacos , Útero/metabolismo
7.
Drug Des Devel Ther ; 10: 141-53, 2016.
Artículo en Inglés | MEDLINE | ID: mdl-26792981

RESUMEN

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.


Asunto(s)
Acroleína/análogos & derivados , Carcinoma Hepatocelular/tratamiento farmacológico , Cinnamomum zeylanicum/química , Neoplasias Hepáticas/tratamiento farmacológico , Acroleína/aislamiento & purificación , Acroleína/farmacología , Animales , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Apoptosis/efectos de los fármacos , Carcinoma Hepatocelular/patología , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , ADN-Topoisomerasas de Tipo I/efectos de los fármacos , ADN-Topoisomerasas de Tipo II/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Humanos , Neoplasias Hepáticas/patología , Masculino , Potencial de la Membrana Mitocondrial/efectos de los fármacos , Ratones , Ratones Endogámicos BALB C , Ratones Desnudos , Ensayos Antitumor por Modelo de Xenoinjerto
8.
J Drug Target ; 24(7): 624-34, 2016 08.
Artículo en Inglés | MEDLINE | ID: mdl-26707867

RESUMEN

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.


Asunto(s)
Acroleína/análogos & derivados , Antineoplásicos Fitogénicos/farmacología , Cinnamomum zeylanicum/química , Inhibidores de Topoisomerasa I/farmacología , Inhibidores de Topoisomerasa II/farmacología , Acroleína/aislamiento & purificación , Acroleína/farmacología , Acroleína/uso terapéutico , Animales , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/uso terapéutico , Apoptosis/efectos de los fármacos , Carcinoma Hepatocelular/enzimología , Carcinoma Hepatocelular/patología , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Descubrimiento de Drogas , Humanos , Neoplasias Hepáticas/enzimología , Neoplasias Hepáticas/patología , Masculino , Potencial de la Membrana Mitocondrial/efectos de los fármacos , Ratones Desnudos , Corteza de la Planta/química , Inhibidores de Topoisomerasa I/aislamiento & purificación , Inhibidores de Topoisomerasa I/uso terapéutico , Inhibidores de Topoisomerasa II/aislamiento & purificación , Inhibidores de Topoisomerasa II/uso terapéutico , Ensayos Antitumor por Modelo de Xenoinjerto
9.
Am J Chin Med ; 43(5): 879-92, 2015.
Artículo en Inglés | MEDLINE | ID: mdl-26227398

RESUMEN

Cinnamon is a traditional folk herb used in Asia and has been reported to have antidiabetic effects. Our previous study showed that cinnamaldehyde (CA), a major effective compound in cinnamon, exhibited hypoglycemic and hypolipidemic effects together in db/db mice. The aim of the present study was to elucidate the molecular mechanisms of the effects of CA on the transcriptional activities of three peroxisome proliferator-activated receptors, (PPAR) α, δ, and γ. We studied the effects of CA through a transient expression assay with TSA201 cells, derivatives of human embryonic kidney cell line (HEK293). Quantitative reverse transcription polymerase chain reaction (qRT-PCR) analysis was also performed to evaluate mRNA expression levels. We show here that CA induced PPARδ, PPARγ and retinoid X receptor (RXR) activation. CA may activate PPARγ in a different manner than pioglitazone, as CA selectively stimulated PPARγ S342A mutant while pioglitazone did not. In addition, CA and L-165041 had a synergistic effect on PPARδ activation. To gather the biological evidence that CA increases PPARs transcription, we further measured the expressions of PPARδ and PPARγ target genes in 3T3-L1 adipocytes. The data showed CA induced the expression of PPARδ and PPARγ target genes, namely aP2 and CD36, in differentiated adipocytes. As a result, PPARδ, PPARγ and their heterodimeric partner RXR appear to play a part in the CA action in the target tissues, thereby enhancing insulin sensitivity and fatty acid ß-oxidation and energy uncoupling in skeletal muscle and adipose tissue.


Asunto(s)
Acroleína/análogos & derivados , Cinnamomum zeylanicum/química , Expresión Génica/efectos de los fármacos , Resistencia a la Insulina/genética , PPAR delta/genética , PPAR gamma/genética , Receptores X Retinoide/genética , Transcripción Genética/efectos de los fármacos , Regulación hacia Arriba/efectos de los fármacos , Acroleína/aislamiento & purificación , Acroleína/farmacología , Adipocitos/metabolismo , Sinergismo Farmacológico , Metabolismo Energético/efectos de los fármacos , Ácidos Grasos/metabolismo , Células HEK293 , Humanos , Músculo Esquelético/metabolismo , Oxidación-Reducción/efectos de los fármacos , PPAR delta/metabolismo , PPAR gamma/metabolismo , Fenoxiacetatos/farmacología , Pioglitazona , ARN Mensajero/genética , Receptores X Retinoide/metabolismo , Reacción en Cadena de la Polimerasa de Transcriptasa Inversa , Estimulación Química , Tiazolidinedionas/farmacología
10.
J Oleo Sci ; 64(8): 825-33, 2015.
Artículo en Inglés | MEDLINE | ID: mdl-26179003

RESUMEN

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.


Asunto(s)
Acroleína/análogos & derivados , Cromatografía de Gases/métodos , Eugenol/análogos & derivados , Cromatografía de Gases y Espectrometría de Masas/métodos , Aceites Volátiles/química , Olfatometría/métodos , Aceites de Plantas/química , Sesquiterpenos/aislamiento & purificación , Uncaria/química , Acroleína/análisis , Acroleína/aislamiento & purificación , Monoterpenos Acíclicos , Ciclohexanoles/análisis , Ciclohexanoles/aislamiento & purificación , Eugenol/análisis , Eugenol/aislamiento & purificación , Furaldehído/análisis , Furaldehído/aislamiento & purificación , Monoterpenos/análisis , Monoterpenos/aislamiento & purificación , Sesquiterpenos/análisis , Compuestos de Tritilo/análisis , Compuestos de Tritilo/aislamiento & purificación
11.
Food Funct ; 6(3): 910-9, 2015 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-25629927

RESUMEN

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.


Asunto(s)
Acroleína/análogos & derivados , Antiinflamatorios no Esteroideos/aislamiento & purificación , Cinnamomum aromaticum/química , Cinnamomum zeylanicum/química , Suplementos Dietéticos , Macrófagos/metabolismo , Acroleína/análisis , Acroleína/química , Acroleína/aislamiento & purificación , Acroleína/metabolismo , Animales , Antiinflamatorios no Esteroideos/análisis , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/metabolismo , Línea Celular , Cinnamomum aromaticum/crecimiento & desarrollo , Suplementos Dietéticos/análisis , Etnofarmacología , Activación de Macrófagos , Macrófagos/inmunología , Medicina Tradicional , Ratones , Estructura Molecular , Óxido Nítrico/antagonistas & inhibidores , Óxido Nítrico/metabolismo , Corteza de la Planta/química , Corteza de la Planta/crecimiento & desarrollo , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/metabolismo , Sri Lanka , Estereoisomerismo , Factor de Necrosis Tumoral alfa/antagonistas & inhibidores , Factor de Necrosis Tumoral alfa/metabolismo
12.
Zhong Yao Cai ; 36(3): 414-5, 2013 Mar.
Artículo en Chino | MEDLINE | ID: mdl-24010325

RESUMEN

OBJECTIVE: To study the constituents of EtOAc extract from Aeschynanthus bracteatus. METHODS: The constituents were isolated and purified by chromatography on silica gel and the structures of the compounds were determined by MS and NMR spectral analysis. RESULTS: On the basis of spectroscopic analysis and comparison with the reported data, compounds were identified as koaburaside (1), coniferaldehyde (2), syringaldehyde (3), sinapinaldehyde (4), 2,4'-dihydroxyacetophenone (5), piceol (6), beta-daucosterol (7), beta-sitosterol (8). CONCLUSION: Compounds 1 and 2 are obtained from this genus for the first time.


Asunto(s)
Acroleína/análogos & derivados , Medicamentos Herbarios Chinos/química , Glicósidos/química , Magnoliopsida/química , Fenoles/química , Acetatos , Acroleína/química , Acroleína/aislamiento & purificación , Benzaldehídos/química , Benzaldehídos/aislamiento & purificación , Medicamentos Herbarios Chinos/aislamiento & purificación , Glicósidos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Estructura Molecular , Fenoles/aislamiento & purificación
13.
Appl Environ Microbiol ; 78(8): 2981-7, 2012 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-22327574

RESUMEN

The efficacies of trans-cinnamaldehyde (TC) and eugenol (EG) for reducing Salmonella enterica serovar Enteritidis colonization in broiler chickens were investigated. In three experiments for each compound, 1-day-old chicks (n = 75/experiment) were randomly assigned to five treatment groups (n = 15/treatment group): negative control (-ve S. Enteritidis, -ve TC, or EG), compound control (-ve S. Enteritidis, +ve 0.75% [vol/wt] TC or 1% [vol/wt] EG), positive control (+ve S. Enteritidis, -ve TC, or EG), low-dose treatment (+ve S. Enteritidis, +ve 0.5% TC, or 0.75% EG), and high-dose treatment (+ve S. Enteritidis, +ve 0.75% TC, or 1% EG). On day 0, birds were tested for the presence of any inherent Salmonella (n = 5/experiment). On day 8, birds were inoculated with ∼8.0 log(10) CFU S. Enteritidis, and cecal colonization by S. Enteritidis was ascertained (n = 10 chicks/experiment) after 24 h (day 9). Six birds from each treatment group were euthanized on days 7 and 10 after inoculation, and cecal S. Enteritidis numbers were determined. TC at 0.5 or 0.75% and EG at 0.75 or 1% consistently reduced (P < 0.05) S. Enteritidis in the cecum (≥3 log(10) CFU/g) after 10 days of infection in all experiments. Feed intake and body weight were not different for TC treatments (P > 0.05); however, EG supplementation led to significantly lower (P < 0.05) body weights. Follow-up in vitro experiments revealed that the subinhibitory concentrations (SICs, the concentrations that did not inhibit Salmonella growth) of TC and EG reduced the motility and invasive abilities of S. Enteritidis and downregulated expression of the motility genes flhC and motA and invasion genes hilA, hilD, and invF. The results suggest that supplementation with TC and EG through feed can reduce S. Enteritidis colonization in chickens.


Asunto(s)
Acroleína/análogos & derivados , Ciego/microbiología , Pollos/microbiología , Eugenol/administración & dosificación , Extractos Vegetales/administración & dosificación , Salmonelosis Animal/prevención & control , Salmonella enteritidis/efectos de los fármacos , Acroleína/administración & dosificación , Acroleína/aislamiento & purificación , Animales , Antibacterianos/administración & dosificación , Antibacterianos/aislamiento & purificación , Carga Bacteriana , Peso Corporal , Eugenol/aislamiento & purificación , Conducta Alimentaria , Extractos Vegetales/aislamiento & purificación , Salmonelosis Animal/patología , Salmonella enteritidis/aislamiento & purificación
14.
Fitoterapia ; 83(3): 523-6, 2012 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-22233864

RESUMEN

Four new pyrenocines, named pyrenocines J-M (1-4), were isolated from an endophytic fungus, Phomopsis sp, by a bioassay-guided method. The structures of the new compound have been assigned from ¹H and ¹³C NMR spectra, DEPT, and by 2D COSY, HMQC, and HMBC experiments. Preliminary studied showed that compounds 1, 2 and 4 showed good antifungal, antibacterial, and algicidal properties, while compound 3 had good antibacterial and algicidal properties.


Asunto(s)
Acroleína/farmacología , Antiinfecciosos/farmacología , Ascomicetos/química , Productos Biológicos/farmacología , Pironas/farmacología , Acroleína/análogos & derivados , Acroleína/química , Acroleína/aislamiento & purificación , Antiinfecciosos/química , Antiinfecciosos/aislamiento & purificación , Productos Biológicos/química , Endófitos/química , Estructura Molecular , Pironas/química , Pironas/aislamiento & purificación
15.
J Ethnopharmacol ; 139(2): 605-15, 2012 Jan 31.
Artículo en Inglés | MEDLINE | ID: mdl-22179023

RESUMEN

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.


Asunto(s)
Acroleína/análogos & derivados , Cardiotónicos/farmacología , Cinnamomum aromaticum , Hemo Oxigenasa (Desciclizante)/biosíntesis , Infarto del Miocardio/prevención & control , Daño por Reperfusión Miocárdica/prevención & control , Miocardio/enzimología , Extractos Vegetales/farmacología , Acroleína/aislamiento & purificación , Acroleína/farmacología , Animales , Antiinflamatorios/farmacología , Antioxidantes/farmacología , Cardiotónicos/aislamiento & purificación , Cinnamomum aromaticum/química , Técnicas de Cocultivo , Modelos Animales de Enfermedad , Relación Dosis-Respuesta a Droga , Inducción Enzimática , Inhibidores Enzimáticos/farmacología , Proteína HMGB1/metabolismo , Hemo Oxigenasa (Desciclizante)/antagonistas & inhibidores , Hemo Oxigenasa (Desciclizante)/genética , Hemo-Oxigenasa 1/biosíntesis , Hemodinámica/efectos de los fármacos , Células Endoteliales de la Vena Umbilical Humana/efectos de los fármacos , Células Endoteliales de la Vena Umbilical Humana/enzimología , Células Endoteliales de la Vena Umbilical Humana/inmunología , Humanos , Masculino , Infarto del Miocardio/enzimología , Infarto del Miocardio/patología , Infarto del Miocardio/fisiopatología , Daño por Reperfusión Miocárdica/enzimología , Daño por Reperfusión Miocárdica/patología , Daño por Reperfusión Miocárdica/fisiopatología , Miocardio/patología , FN-kappa B/genética , FN-kappa B/metabolismo , Infiltración Neutrófila/efectos de los fármacos , Estrés Oxidativo/efectos de los fármacos , Extractos Vegetales/aislamiento & purificación , Plantas Medicinales , Interferencia de ARN , Ratas , Ratas Sprague-Dawley , Superóxido Dismutasa/metabolismo , Factores de Tiempo , Transfección , Troponina I/metabolismo , Factor de Necrosis Tumoral alfa/metabolismo , Células U937 , Molécula 1 de Adhesión Celular Vascular/metabolismo , Función Ventricular Izquierda/efectos de los fármacos , Presión Ventricular/efectos de los fármacos
16.
Nat Prod Res ; 25(18): 1713-9, 2011 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-21936665

RESUMEN

The first phytochemical study of Simira eliezeriana Peixoto (Rubiaceae) allowed the isolation and structural determination of two new diterpenes named simirane A [(5R,6R,8R,9R,10S,11S,13S)-6ß,11ß-dihydroxy-2,4(18),15-erythroxylatrien-1-one] (1) and simirane B [(5S,8R,9R,10S,11S,13S)-11ß-hydroxy-2,4(18),15-erythroxylatrien-1-one] (2), together with seven known compounds: sitosterol (3), stigmasterol (4), campesterol (5), coniferaldehyde (6), vanillin (7), pinoresinol (8) and harman (9) from the bark of the plant. The structures of the compounds were established on the basis of spectroscopic methods, including 1-D and 2-D NMR, HRESI-MS and CD analysis and comparisons with available literature data of known compounds.


Asunto(s)
Diterpenos/aislamiento & purificación , Corteza de la Planta/química , Extractos Vegetales/aislamiento & purificación , Rubiaceae/química , Acroleína/análogos & derivados , Acroleína/aislamiento & purificación , Benzaldehídos/aislamiento & purificación , Colesterol/análogos & derivados , Colesterol/aislamiento & purificación , Diterpenos/análisis , Diterpenos/química , Etanol , Furanos/aislamiento & purificación , Harmina/análogos & derivados , Harmina/aislamiento & purificación , Lignanos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Estructura Molecular , Fitosteroles/aislamiento & purificación , Extractos Vegetales/análisis , Extractos Vegetales/química , Sitoesteroles/aislamiento & purificación
17.
Crit Rev Food Sci Nutr ; 51(6): 547-62, 2011 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-21929331

RESUMEN

The genus Cinnamomum comprises of several hundreds of species, which are distributed in Asia and Australia. Cinnamomum zeylanicum, the source of cinnamon bark and leaf oils, is an indigenous tree of Sri Lanka, although most oil now comes from cultivated areas. C. zeylanicum is an important spice and aromatic crop having wide applications in flavoring, perfumery, beverages, and medicines. Volatile oils from different parts of cinnamon such as leaves, bark, fruits, root bark, flowers, and buds have been isolated by hydro distillation/steam distillation and supercritical fluid extraction. The chemical compositions of the volatile oils have been identified by GC and GC-MS. More than 80 compounds were identified from different parts of cinnamon. The leaf oil has a major component called eugenol. Cinnamaldehyde and camphor have been reported to be the major components of volatile oils from stem bark and root bark, respectively. Trans-cinnamyl acetate was found to be the major compound in fruits, flowers, and fruit stalks. These volatile oils were found to exhibit antioxidant, antimicrobial, and antidiabetic activities. C. zeylanicum bark and fruits were found to contain proanthocyandins with doubly linked bis-flavan-3-ol units in the molecule. The present review provides a coherent presentation of scattered literature on the chemistry, biogenesis, and biological activities of cinnamon.


Asunto(s)
Cinnamomum zeylanicum/química , Extractos Vegetales/farmacología , Aceites de Plantas/farmacología , Acroleína/análogos & derivados , Acroleína/química , Acroleína/aislamiento & purificación , Animales , Antiinfecciosos/química , Antiinfecciosos/farmacología , Antioxidantes/análisis , Antioxidantes/química , Eugenol/química , Eugenol/aislamiento & purificación , Flavonoides/análisis , Flores/química , Frutas/química , Humanos , Hipoglucemiantes/química , Hipoglucemiantes/farmacología , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación , Corteza de la Planta/química , Extractos Vegetales/química , Hojas de la Planta/química , Aceites de Plantas/química
18.
Zhongguo Zhong Yao Za Zhi ; 36(8): 1019-23, 2011 Apr.
Artículo en Chino | MEDLINE | ID: mdl-21809576

RESUMEN

OBJECTIVE: To study the chemical constituents from the ethyl acetate extract of Myricaria bracteata. METHOD: The chemical constituents were isolated and purified by chromatographic techniques, and their structures were identified by physical characters and spectroscopic analysis. RESULT: Sixteen compounds were isolated from the ethyl acetate portion of the 95% ethanolic extract of Myricaria bracteata, and identified as myricarin (1), myricarin B (2), 3alpha-hydroxytaraxer-14-en-28-oic acid (3), myricadiol (4), trans-ferulic acid 22-hydroxydocosanoic acid ester (5), docosyl-3, 4-dihydroxy-trans-cinnamate (6), dillenetin (7), 3, 5, 4'-trihydroxy-7-methoxyflavone (8), 3, 5, 4'-trihydroxy-7, 3'-dimethoxyflavone (9), methyl 3, 5-dihydroxy-4-methoxybenzoate (10), 3-hydroxy-4-methoxy cinnamic acid (11), sinapaldehyde (12), vanillin (13), syringaldehyde (14), 3, 3', 4'-trimethoxyellagic acid (15), methyl p-hyroxybenzoate (16). CONCLUSION: Compounds 5, 6, 12-16 were isolated from the genus Myricaria for the fist time, all of the compounds were isolated from this plant for the fist time, except for 8 and 9.


Asunto(s)
Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Tamaricaceae/química , Acetatos/química , Acroleína/análogos & derivados , Acroleína/química , Acroleína/aislamiento & purificación , Benzaldehídos/química , Benzaldehídos/aislamiento & purificación , Cinamatos/química , Cinamatos/aislamiento & purificación , Flavonas/química , Flavonas/aislamiento & purificación , Glicósidos/química , Glicósidos/aislamiento & purificación , Triterpenos/química , Triterpenos/aislamiento & purificación
19.
Zhongguo Zhong Yao Za Zhi ; 36(8): 1046-9, 2011 Apr.
Artículo en Chino | MEDLINE | ID: mdl-21809583

RESUMEN

OBJECTIVE: To develop an HPLC method for determination of gallic acid, hydroxysafflor yellow A, cinnamic aldehyde and piperine in Tibetan medicine Dangzuo, and to compare the content of four active components in Dangzuo of different Tibetan regions. METHOD: The separation was carried out on a Waters XTerra RP-C18 column ( 4.6 mm x 250 mm, 5 microm). The mobile phases were methanol and water, all contained 0.1% glacial acetic acid, for gradient elution. The gradient program was as follows: 0-22.5 min, methanol was changed from 5% to 50%; 22.5-40 min, changed to 80% 80:20. The flow rate was 1.0 mL x min(-1). The detection wavelength was 270 nm. The reference wavelength was 500 nm. RESULT: The linear ranges of gallic acid, hydroxysafflor yellow A, cinnamic aldehyde and piperine were 0.040-0.640 microg (r = 0.999 8), 0.090-1.440 microg (r = 0.999 9), 0.031-0.500 microg (r = 0.999 9 ) and 0.092-41.477 microg (r = 0.998 9), respectively. The average recoveries (n = 6) were 97.42% (RSD 1.9%), 97.55% (RSD 2.9%), 98.69% (RSD 0.96%) and 96.72% (RSD 4.0%), respectively. The content ranges of gallic acid, hydroxysafflor yellow A, cinnamic aldehyde and piperine in Dangzuo samples of different Tibetan regions were 0.11341.69 mg x g(-1), 0.889-1.51 mg x g(-1), 0.000-40.606 mg x g(-1) and 1.96-2.73 mg x g(-1), respectively. CONCLUSION: The method is a simple and effective for quality control of Tibetan medicine Dangzuo.


Asunto(s)
Acroleína/análogos & derivados , Alcaloides/análisis , Benzodioxoles/análisis , Chalcona/análogos & derivados , Ácido Gálico/análisis , Medicina Tradicional Tibetana , Piperidinas/análisis , Extractos Vegetales/análisis , Extractos Vegetales/aislamiento & purificación , Alcamidas Poliinsaturadas/análisis , Quinonas/análisis , Acroleína/análisis , Acroleína/aislamiento & purificación , Alcaloides/aislamiento & purificación , Benzodioxoles/aislamiento & purificación , Chalcona/análisis , Chalcona/aislamiento & purificación , Cromatografía Líquida de Alta Presión/métodos , Medicamentos Herbarios Chinos/química , Ácido Gálico/aislamiento & purificación , Piperidinas/aislamiento & purificación , Componentes Aéreos de las Plantas/química , Alcamidas Poliinsaturadas/aislamiento & purificación , Control de Calidad , Quinonas/aislamiento & purificación , Estándares de Referencia , Espectrofotometría Ultravioleta/métodos
20.
Phytother Res ; 25(10): 1511-8, 2011 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-21394803

RESUMEN

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.


Asunto(s)
Acroleína/análogos & derivados , Cinnamomum/química , Citocinas/sangre , Factores Inmunológicos/farmacología , Aceites Volátiles/química , Extractos Vegetales/farmacología , Acroleína/química , Acroleína/aislamiento & purificación , Acroleína/farmacología , Aldehídos/análisis , Aldehídos/farmacología , Animales , Benzaldehídos/análisis , Benzaldehídos/farmacología , Femenino , Factores Inmunológicos/química , Factores Inmunológicos/aislamiento & purificación , Ratones , Ratones Endogámicos BALB C , Modelos Animales , Aceites Volátiles/aislamiento & purificación , Ovalbúmina , Extractos Vegetales/química , Hojas de la Planta/química
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