RESUMEN
This study aimed to investigate microwave-assisted extraction (MAE) of dried ginger and to develop a rice-based edible film incorporating ginger extract. The optimal MAE conditions of 400 W microwave power and an extraction time of 1 min were determined using a 32 full factorial design. The optimized extract showed total phenolic compounds (TPC, 198.2 ± 0.7 mg gallic acid equivalent/g), antioxidant activity measured by DPPH (91.4 ± 0.6% inhibition), ABTS (106.4 ± 3.1 mg Trolox/g), and FRAP (304.6 ± 5.5 mg Trolox/g), and bioactive compounds including 6-gingerol (71.5 ± 3.6 mg/g), 6-shogaol (12.5 ± 1.0 mg/g), paradol (23.1 ± 1.1 mg/g), and zingerone (5.0 ± 0.3 mg/g). Crude extract of dried ginger showed antimicrobial activity against Streptococcus mutans DMST 18777, with a minimum inhibitory concentration and minimum bactericidal concentration of 0.5 and 31.2 mg/mL, respectively. The rice-based edible film incorporating 3.2% (w/v) ginger extract tested against S. mutans DMST 18777 had a mean zone of inhibition of 12.7 ± 0.1 mm. Four main phenolic compounds, 6-gingerol, 6-shogaol, paradol, and zingerone, and six volatile compounds, α-curcumene, α-zingiberene, γ-muurolene, α-farnesene, ß-bisabolene, and ß-sesquiphellandrene, were found in rice film fortified with crude ginger extract.
Asunto(s)
Catecoles/farmacología , Películas Comestibles , Alcoholes Grasos/farmacología , Guayacol/análogos & derivados , Microondas , Oryza/química , Extractos Vegetales/farmacología , Extracción en Fase Sólida/métodos , Streptococcus mutans/efectos de los fármacos , Zingiber officinale/química , Catecoles/aislamiento & purificación , Farmacorresistencia Bacteriana , Alcoholes Grasos/aislamiento & purificación , Guayacol/aislamiento & purificación , Guayacol/farmacología , Extractos Vegetales/aislamiento & purificación , TailandiaRESUMEN
The genus Alicyclobacillus comprises a group of Gram-positive, thermo-acidophilic bacteria that are capable of producing highly resistant endospores during unfavorable environmental conditions. The members of this genus inhabit natural environments, including hot springs and soils. The main reason behind the spoilage of final commercial fruit products by Alicyclobacillus is the contamination of fruits with soil at the time of harvesting. Some of the Alicyclobacillus species, including Alicyclobacillus acidoterrestris, are categorized as spoilage bacteria due to their ability to produce off-flavor compounds (e.g., guaiacol and halophenols) that adversely affect the taste and aroma of beverages. In our study, Alicyclobacillus species were isolated from Polish orchard soils and fruits and were subjected to 16S rDNA sequencing. The results of the analysis showed that the isolated strains belonged to A. acidoterrestris and Alicyclobacillus fastidiosus species. All the three isolated strains of A. fastidiosus (f1, f2, f3) exhibited similar morphological and biochemical properties as the strain described in the literature. However, these isolated strains were able to produce guaiacol at temperatures of 20°C, 25°C, and 45°C. Thus, the strains of A. fastidiosus discovered in the present study can be included in the group of spoilage species as they possessed the gene responsible for the production of guaiacol.
Asunto(s)
Alicyclobacillus/genética , Alicyclobacillus/aislamiento & purificación , Frutas/microbiología , Guayacol/aislamiento & purificación , Microbiología del Suelo , Alicyclobacillus/clasificación , Bebidas/microbiología , ADN Bacteriano/genética , Microbiología de Alimentos/métodos , Frutas/química , Jugos de Frutas y Vegetales/microbiología , Guayacol/metabolismo , Polonia , ARN Ribosómico 16S/genética , Esporas Bacterianas/aislamiento & purificación , TemperaturaRESUMEN
Passiflora maliformis is an introduced plant in Australia but its flowers are known to attract the native Jarvis's fruit fly, Bactrocera jarvisi (Tryon). The present study identifies and quantifies likely attractant(s) of male B. jarvisi in P. maliformis flowers. The chemical compositions of the inner and outer coronal filaments, anther, stigma, ovary, sepal, and petal of P. maliformis were separately extracted with ethanol and analyzed using gas chromatography-mass spectrometry (GC-MS). Polyisoprenoid lipid precursors, fatty acids and their derivatives, and phenylpropanoids were detected in P. maliformis flowers. Phenylpropanoids included raspberry ketone, cuelure, zingerone, and zingerol, although compositions varied markedly amongst the flower parts. P. maliformis flowers were open for less than one day, and the amounts of some of the compounds decreased throughout the day. The attraction of male B. jarvisi to P. maliformis flowers is most readily explained by the presence of zingerone in these flowers.
Asunto(s)
Flores/química , Guayacol/análogos & derivados , Passiflora/química , Tephritidae/fisiología , Animales , Australia , Conducta Animal/efectos de los fármacos , Femenino , Cromatografía de Gases y Espectrometría de Masas , Guayacol/química , Guayacol/aislamiento & purificación , Masculino , Feromonas/químicaRESUMEN
Toll-like receptor 4 (TLR4) pathway is one of the major pathways that mediate the inflammation in human body. There are different anti-inflammatory drugs available in the market which specifically act on different signaling proteins of TLR4 pathway but they do have few side effects and other limitations for intended use in human body. In this study, Curcumin and its different analogs have been analyzed as the inhibitors of signaling proteins, i.e. Cycloxygenase-2 (COX-2), inhibitor of kappaß kinase (IKK) and TANK binding kinase-1 (TBK-1) of TLR4 pathway using different computational tools. Initially, three compounds were selected for respective target based on free binding energy among which different compounds were reported to have better binding affinity than commercially available drug (control). Upon continuous computational exploration with induced fit docking (IFD), 6-Gingerol, Yakuchinone A and Yakuchinone B were identified as the best inhibitors of COX-2, IKK, and TBK-1 respectively. Then their drug-like potentialities were analyzed in different experiments where they were also predicted to perform well. Hopefully, this study will uphold the efforts of researchers to identify anti-inflammatory drugs from natural sources.
Asunto(s)
Química Computacional , Curcumina/química , Inflamación/tratamiento farmacológico , Receptor Toll-Like 4/química , Catecoles/química , Catecoles/aislamiento & purificación , Catecoles/uso terapéutico , Curcumina/análogos & derivados , Curcumina/aislamiento & purificación , Curcumina/uso terapéutico , Ciclooxigenasa 2/genética , Diarilheptanoides/química , Diarilheptanoides/aislamiento & purificación , Diarilheptanoides/uso terapéutico , Alcoholes Grasos/química , Alcoholes Grasos/aislamiento & purificación , Alcoholes Grasos/uso terapéutico , Guayacol/análogos & derivados , Guayacol/química , Guayacol/aislamiento & purificación , Guayacol/uso terapéutico , Humanos , Quinasa I-kappa B/genética , Inflamación/genética , Lipopolisacáridos/química , FN-kappa B/antagonistas & inhibidores , FN-kappa B/genética , Preparaciones Farmacéuticas/química , Proteínas Serina-Treonina Quinasas/genética , Transducción de Señal/efectos de los fármacos , Receptor Toll-Like 4/antagonistas & inhibidores , Receptor Toll-Like 4/genéticaRESUMEN
Ginger (Zingiber officinale Roscoe) and its active compounds (gingerols, shogaols and paradols) have been reported as having beneficial functions for several diseases, including diabetes. In this study, we revealed that the steaming process could enhance the anti-diabetic potential of ginger. To confirm the anti-diabetic effect of steamed ginger extract (GG03), we assessed pancreatic islets impaired by alloxan in zebrafish and demonstrated anti-hyperglycemic efficacy in a mouse model. The EC50 values of ginger extract (GE) and GG03 showed that the efficacy of GG03 was greater than that of GE. In addition, LC50 values demonstrated that GG03 had lower toxicity than GE, and the comparison of the Therapeutic Index (TI) proved that GG03 is a safer functional food. Furthermore, our data showed that GG03 significantly lowered hyperglycemia in a diabetic mouse model. HPLC was performed to confirm the change in the composition of steamed ginger. Interestingly, GG03 showed a 375% increase in 1-dehydro-6-gingerdione (GD) compared with GE. GD has not yet been studied much pharmacologically. Thus, we identified the protective effects of GD in the damaged pancreatic islets of diabetic zebrafish. We further assessed whether the anti-diabetic mechanism of action of GG03 and GD involves insulin secretion. Our results suggest that GG03 and GD might stimulate insulin secretion by the closure of KATP channels in pancreatic ß-cells.
Asunto(s)
Diabetes Mellitus Experimental/tratamiento farmacológico , Alcoholes Grasos/farmacología , Guayacol/análogos & derivados , Hipoglucemiantes/farmacología , Células Secretoras de Insulina/efectos de los fármacos , Insulina/metabolismo , Canales KATP/antagonistas & inhibidores , Extractos Vegetales/farmacología , Zingiber officinale , Animales , Glucemia/efectos de los fármacos , Glucemia/metabolismo , Diabetes Mellitus Experimental/metabolismo , Diabetes Mellitus Experimental/patología , Alcoholes Grasos/aislamiento & purificación , Alcoholes Grasos/toxicidad , Zingiber officinale/química , Zingiber officinale/toxicidad , Guayacol/aislamiento & purificación , Guayacol/farmacología , Guayacol/toxicidad , Hipoglucemiantes/aislamiento & purificación , Hipoglucemiantes/toxicidad , Células Secretoras de Insulina/metabolismo , Células Secretoras de Insulina/patología , Canales KATP/metabolismo , Masculino , Ratones Endogámicos ICR , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/toxicidad , Raíces de Plantas , Bloqueadores de los Canales de Potasio/farmacología , Secretagogos/farmacología , Transducción de Señal , Vapor , Pez CebraRESUMEN
Hawthorn seed can be used to produce various bioactive compounds through destructive distillation. In this study, an accurate and feasible analytical method based on a gas chromatography mass spectrometer (GC-MS) was developed for simultaneous determination of six major compounds (contributing to more than 3% in total peak area) in destructive distillation extracts of hawthorn seed collected at different temperatures ranging from 150 to 270 °C. Then, a broth microdilution method coupled with grey correlation analysis was engaged in the evaluation of their antimicrobial activities and the screening of primarily active compounds. Results indicate that the extract collected from 211 to 230 °C had the highest content of six major compounds (furfural, 2-methoxyphenol, 2-methoxy-4-methylphenol, 4-ethyl-2-methoxyphenol, 2,6-dimethoxyphenol, and 5-tertbutylpyrogallol) and the strongest antibacterial activity. Besides, 2,6-dimethoxyphenol was found to be a potential compound in inhibiting the growth of vaginitis pathogens. This study provided an optimum temperature for the destructive distillation of hawthorn seed, reducing the waste of energy, and saving the cost of production in the hawthorn industry.
Asunto(s)
Antibacterianos/farmacología , Crataegus/química , Cromatografía de Gases y Espectrometría de Masas/métodos , Semillas/química , Antibacterianos/química , Cresoles/química , Cresoles/aislamiento & purificación , Cresoles/farmacología , Destilación/métodos , Furaldehído/química , Furaldehído/aislamiento & purificación , Furaldehído/farmacología , Guayacol/química , Guayacol/aislamiento & purificación , Guayacol/farmacología , Extractos Vegetales/química , Extractos Vegetales/farmacología , Pirogalol/análogos & derivados , Pirogalol/química , Pirogalol/aislamiento & purificación , Pirogalol/farmacologíaRESUMEN
Key odorants of red wine made from the hybrid grapes of Marselan (Vitis vinifera L.) were isolated by solid-phase extraction (SPE) and explored by gas chromatography-olfactometry (GC-O) analysis. Application of aroma extract dilution analysis (AEDA) revealed 43 odor-active compounds, and 31 odorants among them were detected with flavor dilution (FD) factors ranging from 9 to 2187. Comprehensive two-dimensional gas chromatography and time-of-flight mass spectrometry (GC × GC-TOF-MS) were exploited to quantitate the aroma-active compounds with FD ≥9. The identification indicated ß-damascenone as having the highest FD factors, followed by eugenol, 2,3-butanedione, citronellol, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, phenethyl acetate, guaiacol, and 2-methoxy-4-vinylphenol. A total of 21 compounds were found to have odor activity values (OAVs) >1.0. Aroma reconstitution validation experiments showed a good similarity of blackberry, green pepper, honey, raspberry, caramel, smoky, and cinnamon aroma attributes between the original Marselan wine and the reconstructed wine. In addition, omission tests were carried out to further determine the contribution of odorants to the overall aroma.
Asunto(s)
Odorantes/análisis , Olfato/fisiología , Vitis/química , Compuestos Orgánicos Volátiles/aislamiento & purificación , Vino/análisis , Monoterpenos Acíclicos/aislamiento & purificación , Diacetil/aislamiento & purificación , Eugenol/aislamiento & purificación , Femenino , Furanos/aislamiento & purificación , Cromatografía de Gases y Espectrometría de Masas , Guayacol/análogos & derivados , Guayacol/aislamiento & purificación , Humanos , Masculino , Norisoprenoides/aislamiento & purificación , Olfatometría/instrumentación , Olfatometría/métodos , Extracción en Fase Sólida/métodos , Espectrometría de Masa por Láser de Matriz Asistida de Ionización Desorción , Gusto/fisiología , Compuestos de Vinilo/aislamiento & purificación , Compuestos Orgánicos Volátiles/clasificaciónRESUMEN
Zingerone, 4-(4-hydroxy-3-methoxyphenyl)-2-butanone (Zg), a phenolic compound isolated from ginger is reported to have anti-inflammatory and antidiabetic properties. However, its role in the promotion of osteogenesis is not known. In this study, we investigated the therapeutic effect of Zg on osteogenesis at the cellular and molecular levels. Zg treatment was nontoxic to mouse mesenchymal stem cells (mMSCs). At the cellular level, it enhanced osteoblast differentiation as evidenced by more calcium deposits. At the molecular level, Zg stimulated the expression of Runx2 (a bone transcription factor) and other marker genes of osteoblast differentiation in mMSCs. Recent studies indicated that microRNAs (miRNAs) regulate bone metabolism, and we identified that Zg treatment in mMSCs upregulated mir-590, a positive regulator of Runx2 by targeting Smad7, an antagonist of TGF-ß1 signaling. Thus, the osteogenic potential of Zg would be beneficial for treating bone and bone-related diseases.
Asunto(s)
Conservadores de la Densidad Ósea/farmacología , Subunidad alfa 1 del Factor de Unión al Sitio Principal/genética , Guayacol/análogos & derivados , MicroARNs/genética , Osteogénesis/efectos de los fármacos , Animales , Conservadores de la Densidad Ósea/aislamiento & purificación , Calcio/metabolismo , Diferenciación Celular/efectos de los fármacos , Línea Celular , Subunidad alfa 1 del Factor de Unión al Sitio Principal/agonistas , Subunidad alfa 1 del Factor de Unión al Sitio Principal/metabolismo , Regulación de la Expresión Génica , Zingiber officinale/química , Guayacol/aislamiento & purificación , Guayacol/farmacología , Células Madre Mesenquimatosas/citología , Células Madre Mesenquimatosas/efectos de los fármacos , Células Madre Mesenquimatosas/metabolismo , Ratones , MicroARNs/agonistas , MicroARNs/metabolismo , Osteoblastos/citología , Osteoblastos/efectos de los fármacos , Osteoblastos/metabolismo , Osteogénesis/genética , Transducción de Señal , Proteína smad7/genética , Proteína smad7/metabolismo , Factor de Crecimiento Transformador beta1/genética , Factor de Crecimiento Transformador beta1/metabolismoRESUMEN
In this study, novel Cesium (Cs) doped TiO2 nanotubes photoelectrode (Cs/TiO2NTs) were synthesized by simple electrochemical anodization method and characterized by several physicochemical techniques. In particular, the photocatalytic (PC), electrocatalytic (EC) and photoelectrocatalytic (PEC) activity of newly synthesized Cs/TiO2NTs electrodes was investigated using 4-Chloroguaiacol (4-CG). The effect of operating parameters like Cs concentration, electrolyte concentration, external current and pH on degradation efficacy was examined. PEC oxidation using Cs/TiO2NTs lead to 92% degradation of 4-CG in 6â¯h of solar light irradiation under optimized conditions (2.5â¯mM Cs, 160â¯mgâ¯L-1 Na2SO4, 0.03 A current and pH 3). A comparative assessment between PEC, PC and EC process manifested that PEC process was most efficient than the other two processes and Cs/TiO2NTs exhibited higher PEC activity than bare-TiO2 electrodes in terms of degradation and mineralization of organic pollutant. The generation of OH radicals was found to be highest in PEC when compared to EC and PC process. Possible intermediates/byproducts were identified by GC-MS technique and a corresponding tentative degradation pathway has been proposed. Cytotoxicity study showed that PEC has potential to detoxify 4-CG. Hence, combination of TiO2 electrodes decorated with Cs metal can act as a highly efficient photoelectrode for the degradation of hazardous pollutants.
Asunto(s)
Cesio/química , Técnicas Electroquímicas/métodos , Guayacol/análogos & derivados , Nanotubos/química , Titanio/química , Catálisis , Electrodos , Contaminantes Ambientales/aislamiento & purificación , Guayacol/aislamiento & purificación , Oxidación-ReducciónRESUMEN
Background: Alpinia officinarum Hance (ginger family) is an important Chinese medicine, especially in Southern China. Objective: A simple and effective high-performance thin-layer chromatography coupled with 2, 2-diphenyl-1-picrylhydrazyl bioautography (HPTLC-DPPH) and electrospray ionization quadrupole time-of-flight tandem mass spectrometry (ESI-Q-TOF-MS/MS) method was developed for the bioactivity-based quality control of A. officinarum. Methods: The HPTLC-DPPH and ESI-Q-TOF-MS/MS were applied for the analysis of different parts of A. officinarum after using methanol extraction for 23 batches of taproot, four batches of aerial, and three batches of fibril parts. Results: The systematic evaluation showed that similar components in taproot and aerial parts make the major antioxidant activity. However, based on our evaluation, the antioxidant ability of the aerial parts is lower than the taproot parts. There is also a significant difference (P < 0.05) between taproot and fibril parts of the root. The chemical structures of compounds with the antioxidant capacity were tentatively identified as 5R-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-phenyl-3-heptanone (band 1), kaempferide (band 2), and galangin (band 3) based on ESI-Q-TOF-MS/MS analytical results and further confirmed by standards. Conclusions: This identification indicated that two flavonoid compounds and one diarylheptanoid compound possessed high potentials to be used as the antioxidant biomarkers for the quality control of A. officinarum. Highlights: The comparison of different parts could be considered as guidelines for the usage of A. officinarum.
Asunto(s)
Alpinia/química , Antioxidantes/aislamiento & purificación , Flavonoides/aislamiento & purificación , Guayacol/análogos & derivados , Quempferoles/aislamiento & purificación , Biomarcadores , Compuestos de Bifenilo/química , Cromatografía en Capa Delgada/métodos , Guayacol/aislamiento & purificación , Picratos/química , Componentes Aéreos de las Plantas/química , Raíces de Plantas/química , Extracción en Fase Sólida/métodosRESUMEN
Ginger oleoresin (GO) can be encapsulated within a protective lipid matrix in order to facilitate handling, provide protection against the external environment or promote the stability of GO compounds. The aim of this study was to verify the ability of solid lipid microparticles (SLMs) containing GO (10-20% w/w) to maintain or improve the stability of ginger compounds, by monitoring SLMs' characteristics during storage at different temperatures (25 and 40⯰C). The lipids matrix of SLMs were composed by stearic acid (90, 80, 75, 65% w/w) and oleic acid (15% w/w), The crystalline structure of the particles after 84â¯days of storage did not present any polymorphic alterations, while presenting spherical form upon scanning by electron microscopy. SLMs containing oleic acid showed degradation of 6-gingerol when stored at 40⯰C. Major volatile compounds had better stability in particles containing oleic acid. Kinetics of volatiles release resulted in a diffusion mechanism. SLMs showed better stability of GO compounds during storage at 25⯰C than un-encapsulated GO and could, therefore, improve its distribution in foods due to its conversion to powder.
Asunto(s)
Conservación de Alimentos/métodos , Almacenamiento de Alimentos/métodos , Odorantes , Ácido Oléico/química , Extractos Vegetales/aislamiento & purificación , Ácidos Esteáricos/química , Temperatura , Compuestos Orgánicos Volátiles/aislamiento & purificación , Zingiber officinale/química , Catecoles/aislamiento & purificación , Cristalización , Alcoholes Grasos/aislamiento & purificación , Guayacol/análogos & derivados , Guayacol/aislamiento & purificación , Cinética , Tamaño de la Partícula , Polvos , Propiedades de SuperficieRESUMEN
ETHNOPHARMACOLOGICAL RELEVANCE: Dendrobium. chrysotoxum Lindl is a commonly used species of medicinal Dendrobium which belongs to the family of Orchidaceae, locally known as "Shihu" or "Huangcao". D. chrysotoxum Lindl is widely known for medicinal values in traditional Chinese medicine as it possesses anti-inflammatory, anti-hyperglycemic induction, antitumor and antioxidant properties. STUDY AIM: To characterize the interaction between gigantol extracted from D. chrysotoxum Lindl and the AR gene, and determine gigantol's efficacy against cataractogenesis. MATERIALS AND METHODS: Human lens epithelial cells (HLECs) were induced by glucose as the model group. Reverse transcription polymerase chain reaction (RT-PCR) was used to assess AR gene expression. Then, the mode of interaction of gigantol with the AR gene was evaluated by UV-visible spectroscopy, atomic force microscope (AFM) and surface-enhanced Raman spectroscopy (SERS). The binding constant was determined by UV-visible. RESULTS: Gigantol depressed AR gene expression in HLECs. UV-visible spectra preliminarily indicated that interaction between the AR gene and gigantol may follow the groove mode, with a binding constant of 1.85×103L/mol. Atomic force microscope (AFM) data indicated that gigantol possibly bound to insert AR gene base pairs of the double helix. Surface-enhanced Raman spectroscopy (SERS) studies further supported these observations. CONCLUSION: Gigantol extracted from D. chrysotoxum Lindl not only has inhibitory effects on aldose reductase, but also inhibits AR gene expression. These findings provide a more comprehensive theoretical basis for the use of Dendrobium for the treatment of diabetic cataract.
Asunto(s)
Aldehído Reductasa/genética , Bibencilos/farmacología , Catarata/prevención & control , Dendrobium/química , Guayacol/análogos & derivados , Bibencilos/aislamiento & purificación , Catarata/etiología , Células Cultivadas , Complicaciones de la Diabetes/prevención & control , Células Epiteliales/efectos de los fármacos , Células Epiteliales/enzimología , Regulación Enzimológica de la Expresión Génica/efectos de los fármacos , Glucosa/metabolismo , Guayacol/aislamiento & purificación , Guayacol/farmacología , Humanos , Cristalino/citología , Cristalino/efectos de los fármacos , Cristalino/enzimología , Reacción en Cadena de la Polimerasa de Transcriptasa Inversa , Espectrometría RamanRESUMEN
Brettanomyces/Dekkera produces 4-ethylphenol (4-EP) and 4-ethylguaiacol (4-EG) from hydroxycinnamic acids that affect the wine aroma and overall quality. A simple, cheap, fast and reliable quantitation method is needed for routine quality control of wines. In this work a simple method based on one simple liquid-liquid extraction with pentane/diethyl ether (2:1) and analysis by GC-MS allow to obtain very good recoveries (98-102%) and low quantification limits (24 and 11µg/L for 4-EP and 4-EG, respectively), well below the sensory threshold for these volatile phenols and with an adequate measurement uncertainty: 70, 1.75 and 78, 1.95 and 1.35µg/L for levels of 1000, 25µg/L for 4-EP and 1000, 25 and 10µg/L for 4-EG, respectively. In addition a screening of eight fining agents (mineral, protein and polysaccharide based) for reducing the levels of these volatile phenols in red wines was performed, and the impact on the physicochemical characteristics of red wines was evaluated. At the levels used, activated carbon was the most efficient fining agent in removing 4-ethylphenol and 4-ethylguaiacol from red wines (57%) resulting in a 75% decrease of headspace concentration of these volatile phenols. Lower reductions were observed when using egg albumin (19%) resulting in a 30% decrease in the headspace concentration. Other fining agents although not reducing the total amount of the volatile phenols present in wine decreased their concentrations in the headspace like isinglass (27%), carboxymethylcellulose (15%) and chitosan (27%). All of these fining agents could be a possibility for treating wine contaminated with 4-ethylphenol and 4-ethylguaiacol.
Asunto(s)
Guayacol/análogos & derivados , Extracción Líquido-Líquido/métodos , Fenoles/análisis , Vino/análisis , Cromatografía de Gases y Espectrometría de Masas , Guayacol/análisis , Guayacol/química , Guayacol/aislamiento & purificación , Límite de Detección , Modelos Lineales , Fenoles/química , Fenoles/aislamiento & purificación , Reproducibilidad de los ResultadosRESUMEN
Hierochloë odorata (L.) P. Beauv. (Poaceae), commonly known as sweetgrass, has documented use as an insect repellent by the Flatheads of Montana and Blackfoot of Alberta. Both the Flatheads of Montana and Blackfoot of Alberta would use braided plant material in a sachet in clothing or burn them from one end as incense, air/clothing freshener, and insect repellent. This study evaluated the insect-repellent properties of this plant using an in vitro mosquito Aedes aegypti feeding bioassay-directed approach to identify the compound(s) responsible for the observed activities. Evaluation of crude extracts produced from H. odorata revealed that the hydrodistillate had the highest level of mosquito biting deterrence. Fractionation of this extract, followed by re-evaluation for mosquito biting deterrence, produced many active fractions, which were evaluated by spectroscopic techniques and determined to contain phytol, coumarin, and 2-methoxy-4-vinylphenol. Phytol and coumarin were both determined to be responsible for the Ae. aegypti biting deterrency. Scientific evidence reported here validates its traditional use as a biting-insect deterrent.
Asunto(s)
Aedes/efectos de los fármacos , Repelentes de Insectos/aislamiento & purificación , Repelentes de Insectos/farmacología , Poaceae/química , Animales , Cumarinas/aislamiento & purificación , Cumarinas/farmacología , Evaluación Preclínica de Medicamentos/métodos , Etnobotánica , Femenino , Guayacol/análogos & derivados , Guayacol/aislamiento & purificación , Guayacol/farmacología , Humanos , Indígenas Norteamericanos , Aceites Volátiles/análisis , Aceites Volátiles/química , Fitol/aislamiento & purificación , Fitol/farmacología , Extractos Vegetales/química , Extractos Vegetales/farmacología , Compuestos de Vinilo/aislamiento & purificación , Compuestos de Vinilo/farmacologíaRESUMEN
Background Antioxidant and antihistamine agents from Barleria noctiflora L.f. as natural source due to the existing modern medicine give various adverse effects to overcome these problems with natural products. MethodsB. noctiflora leaves extract was fractionated with column chromatography; the homogenized fractions were monitored with thin layer chromatography (TLC) and characterized by using UV-visible, FT-IR, 1H NMR, 13C NMR and mass spectrometry spectral studies. The volatile phytoconstituents of B. noctiflora extract were analysed by gas chromatography-mass spectrometry. Phytoconstituents from B. noctiflora leaves extract were screened for their antioxidant and antihistamine potential in vitro (2,2-diphenyl-1-picrylhydrazyl radical scavenging activity, 2,2'-azinobis-3-ethylbenzothiozoline-6-sulfonic acid radical decolouration assay, nitric oxide radical scavenging activity, superoxide radical scavenging activity and hydrogen peroxide radical scavenging activity) and in silico (molecular docking), respectively. Results Antioxidant and antihistamine barlerinoside has been isolated and characterized from the leaves of B. noctiflora L.f. Barlerinoside revealed their free-radical scavenging ability on OH-, OHâ¢, NO-, O2- and H2O2 radicals and found high percentage inhibition against OH- radical at the IC50 value of 50.45±2.52â µg. The methanol (MeOH) extract of B. noctiflora leaves contains cyclotene; N,N-dimethylglycine; tetrahydrocyclopenta [1,3] dioxin-4-one; phenol, 2-methoxy-; benzofuran, 2-methyl-; 1,4:3,6-dianhydro-α-d-glucopyranose; 2-methoxy-4-vinylphenol; 1,3;2,5-dimethylene-l-rhamnitol; levoglucosan and bicyclo[2.2.2]oct-7-ene-2,5-dione as being the major compounds. Among phytoconstituents present in the extract, the hexestrol; 1,2-benzenedicarboxylic acid, bis(2-methylpropyl) ester; 1-(3,6,6-trimethyl-1,6,7,7a-tetrahydrocyclopenta[c]pyran-1-yl) ethanone; megastigmatrienone; furan interacted with histamine H1 receptor and bind at GLU-177 and ASP-178 with high binding energy score -13.95, -13.41, -12.56, -12.03, and -11.72âkcal/mol, respectively, and the expected hydrolysed products of compound-1a and compound-1b from barlerinoside showed -8.91 and -8.68âkcal/mol binding energy against the histamine H1 receptor. This showed that the active ligands exactly bind with active binding site of the protein. ConclusionsWe can conclude that isolated barlerinoside from B. noctflora L.f. has potent antioxidant activity against synthetic free radicals and antihistamine activity against histamine H1 receptor.
Asunto(s)
Acanthaceae/química , Antioxidantes/farmacología , Ácidos Cafeicos/farmacología , Antagonistas de los Receptores Histamínicos/farmacología , Oligosacáridos/farmacología , Extractos Vegetales/farmacología , Antioxidantes/aislamiento & purificación , Compuestos de Bifenilo/metabolismo , Ácidos Cafeicos/aislamiento & purificación , Ácidos Cafeicos/metabolismo , Guayacol/análogos & derivados , Guayacol/aislamiento & purificación , Guayacol/farmacología , Antagonistas de los Receptores Histamínicos/aislamiento & purificación , Radical Hidroxilo/metabolismo , Oligosacáridos/aislamiento & purificación , Oligosacáridos/metabolismo , Picratos/metabolismo , Extractos Vegetales/química , Hojas de la Planta/química , Receptores Histamínicos H1/metabolismo , Compuestos de Vinilo/aislamiento & purificación , Compuestos de Vinilo/farmacologíaRESUMEN
A new (propylphenyl)bibenzyl, bambusifolol (1), along with six known compounds, batatasin III (2), tristin (3), 3-hydroxy-5-methoxy bibenzyl (4), gigantol (5), 3',5-dimethoxy-9,9'-diacetyl-4,7'-epoxy-3,8'-bilign-7-ene-4'-methol (6) and balanophonin (7) were isolated from the whole plants of Eria bambusifolia. Their structures were elucidated by the means of extensive spectroscopic analysis. 3-7 were isolated from the genus Eria for the first time and 2 obtained originally from E. bambusifolia. All the compounds isolated were evaluated for their cytotoxicity against human tumour HL-60, SMMC-7721, A-549, MCF-7 and SW-480 cell lines, but none showed significant activity.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Bibencilos/aislamiento & purificación , Dendrobium/química , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Bibencilos/química , Bibencilos/farmacología , Línea Celular Tumoral , Guayacol/análogos & derivados , Guayacol/química , Guayacol/aislamiento & purificación , Guayacol/farmacología , Humanos , Lignanos/química , Lignanos/aislamiento & purificación , Lignanos/farmacología , Estilbenos/química , Estilbenos/aislamiento & purificación , Estilbenos/farmacologíaRESUMEN
A new 9,10-dihydrophenanthrene,1,5-dihydroxy-3,4,7-trimethoxy-9,10-dihydrophenanthrene (1) was isolated and identified from the whole plants of Dendrobium moniliforme, as well as 24 known compounds including hircinol (2), (2R*,3S*)-3-hydroxymethyl-9-methoxy-2-(4'-hydroxy-3',5'-dimethoxyphenyl)-2,3,6,7-tetrahydro-phenanthro[4,3-b]furan-5,11-diol (3), diospyrosin (4), aloifol I (5), moscatilin (6), 3,4'-dihydroxy-3',4,5-trimethoxybibenzyl (7), gigantol (8), 3,3'-dihydroxy-4,5-dimethoxybibenzyl (9), longicornuol A (10), N-trans-cinnamoyltyramine (11), paprazine (12), N-trans-feruloyl 3'-O-methyldopamine (13), moupinamide (14), dihydroconiferyl dihydro-p-coumarate (15), dihydrosinapyl dihydro-p-coumarate (16), 3-isopropyl-5-acetoxycyclohexene-2-one-1 (17), p-hydroxybenzaldehyde (18), vanillin (19), p-hydroxyphenylpropionic acid (20), vanillic acid (21), protocatechuic acid (22), (+)-syringaresinol (23), ß-sitosterol (24) and daucosterol (25). Compounds 3, 4, 13, 16, 17 and 20 were isolated from the Dendrobium genus for the first time, and compounds 2, 5, 7, 9-12, 14, 15, 18, 21 and 22 were originally obtained from D. moniliforme.
Asunto(s)
Dendrobium/química , Fenantrenos/química , Benzaldehídos/química , Benzaldehídos/aislamiento & purificación , Bibencilos/química , Bibencilos/aislamiento & purificación , Cinamatos/química , Cinamatos/aislamiento & purificación , Ácidos Cumáricos/química , Ácidos Cumáricos/aislamiento & purificación , Furanos/química , Furanos/aislamiento & purificación , Guayacol/análogos & derivados , Guayacol/química , Guayacol/aislamiento & purificación , Lignanos/química , Lignanos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Estructura Molecular , Fenantrenos/aislamiento & purificación , Fenilpropionatos/química , Fenilpropionatos/aislamiento & purificación , Plantas Medicinales/química , Sitoesteroles/química , Sitoesteroles/aislamiento & purificación , Espectrometría de Masa por Ionización de Electrospray , Tiramina/análogos & derivados , Tiramina/química , Tiramina/aislamiento & purificaciónRESUMEN
The chemical composition and antioxidant activities of the essential oil from Nandina domestica fruits were studied for the first time. Twenty-two compounds, representing 82.79% of the oil, were identified from the oil. The major compounds were 3-hexen-1-ol (12.9%), linalool (12.3%), 2-methoxy-4-vinylphenol (9.9%), oleic acid (8.0%), furfural (5.8%) and 2,6-di-tert-butyl-4-methylphenol (5.7%). The antioxidant activities of the oil were evaluated using reducing power, metal chelating ability and scavenging capacity against 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2'-azinobis-3-ethylbenzthiazoline-6-sulfonate (ABTS) and superoxide anion free radical. The oil exhibited significant antioxidant activities.
Asunto(s)
Antioxidantes/química , Antioxidantes/farmacología , Berberidaceae/química , Aceites Volátiles/química , Aceites Volátiles/farmacología , Monoterpenos Acíclicos , Compuestos de Bifenilo/química , Evaluación Preclínica de Medicamentos/métodos , Frutas/química , Guayacol/análogos & derivados , Guayacol/aislamiento & purificación , Hexanoles/aislamiento & purificación , Concentración 50 Inhibidora , Monoterpenos/aislamiento & purificación , Picratos/química , Superóxidos/química , Compuestos de Vinilo/aislamiento & purificaciónRESUMEN
Two sample preparation methods, namely hydrodistillation (HD) and solvent-assisted flavor evaporation (SAFE), have been used to investigate the essential oils of the aerial parts (leaves and stems) of Symplocarpus foetidus, a plant with a characteristic odor, by gas chromatography mass spectrometry (GC-MS). Characteristic aroma-active compounds in the oils were detected by GC-Olfactometry (GC-O) and aroma extract dilution analysis (AEDA). From the HD method, the main compounds in the oil were found to be p-vinyl-guaiacol (15.5%), 2-pentyl-furan (13.4%), and (Z)-ligustilide (9.5%). From the SAFE method, the main compounds were 2-butoxy-ethanol (49.6%), ethyl-pentanoate (4.5%), and mesitylene (4.0%). In HD oil, the most intense aroma-active compounds were 2-pentyl-furan (flavor dilution factor (FD) = 32, odor activity value (OAV) = 57), p-vinyl-guaiacol (FD = 16, OAV = 41), and dimethyl disulfide (FD = 16, OAV = 41). In SAFE oil, the main aroma-active compounds were 2-butoxy ethanol (FD = 32, OAV = 16), and 2-methoxy thiazole (FD = 32, OAV = 25).
Asunto(s)
Araceae/química , Odorantes/análisis , Aceites Volátiles/química , Aceites de Plantas/química , 4-Butirolactona/análogos & derivados , 4-Butirolactona/análisis , 4-Butirolactona/aislamiento & purificación , Derivados del Benceno/análisis , Derivados del Benceno/aislamiento & purificación , Destilación/métodos , Disulfuros/análisis , Disulfuros/aislamiento & purificación , Glicoles de Etileno/análisis , Glicoles de Etileno/aislamiento & purificación , Furanos/análisis , Furanos/aislamiento & purificación , Cromatografía de Gases y Espectrometría de Masas , Guayacol/análisis , Guayacol/aislamiento & purificación , Técnicas de Dilución del Indicador , Aceites Volátiles/aislamiento & purificación , Olfatometría/métodos , Hojas de la Planta/química , Aceites de Plantas/aislamiento & purificación , Tallos de la Planta/química , Valeratos/análisis , Valeratos/aislamiento & purificación , VolatilizaciónRESUMEN
We introduce a real-time method to monitor the evolution of oak aromas during the oak toasting process. French and American oak wood boards were toasted in an oven at three different temperatures, while the process-gas was continuously transferred to the inlet of a proton-transfer-reaction time-of-flight mass spectrometer for online monitoring. Oak wood aroma compounds important for their sensory contribution to oak-aged wine were tentatively identified based on soft ionization and molecular mass. The time-intensity profiles revealed toasting process dynamics illustrating in real-time how different compounds evolve from the oak wood during toasting. Sufficient sensitivity was achieved to observe spikes in volatile concentrations related to cracking phenomena on the oak wood surface. The polysaccharide-derived compounds exhibited similar profiles; whilst for lignin-derived compounds eugenol formation differed from that of vanillin and guaiacol at lower toasting temperatures. Significant generation of oak lactone from precursors was evident at 225 (o)C. Statistical processing of the real-time aroma data showed similarities and differences between individual oak boards and oak wood sourced from the different origins. This study enriches our understanding of the oak toasting process and demonstrates a new analytical approach for research on wood volatiles.