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1.
J Agric Food Chem ; 71(41): 15319-15330, 2023 Oct 18.
Artículo en Inglés | MEDLINE | ID: mdl-37812808

RESUMEN

Thearubigins (TRs) are chemically ill-defined black tea pigments composed of numerous catechin oxidation products. TRs contain oligomeric components; however, the oligomerization mechanisms are poorly understood. The comparison of the 13C nuclear magnetic resonance (NMR) spectra of TRs with different molecular sizes suggested the participation of A-ring methine carbons in the oligomerization. Crushing fresh tea leaves with phloroglucinol, a mimic of the catechin A-rings, yielded the phloroglucinol adducts of the B-ring quinones of pyrogallol-type catechins and dehydrotheasinensins, indicating that intermolecular oxidative couplings between pyrogallol-type B-rings and A-rings are involved in the oligomerization. This is supported by the comparison of the 13C NMR spectra of the oligomers generated from the dehydrotheasinensins and epicatechin. Furthermore, the presence of the quinones or related structures in the catechin oligomers is shown by condensation with 1,2-phenylenediamine. The pyrogallol-type catechins account for approximately 70% of tea catechins; therefore, the B-A ring couplings of the pyrogallol-type catechins are important in the catechin oligomerization involved in TR production.


Asunto(s)
Camellia sinensis , Catequina , Té/química , Catequina/química , Pirogalol/química , Camellia sinensis/química , Floroglucinol , Quinonas
2.
Molecules ; 26(24)2021 Dec 08.
Artículo en Inglés | MEDLINE | ID: mdl-34946525

RESUMEN

Biomass valorization to building block chemicals in food and pharmaceutical industries has tremendously gained attention. To produce monophenolic compounds from palm empty fruit bunch (EFB), EFB was subjected to alkaline hydrothermal extraction using NaOH or K2CO3 as a promotor. Subsequently, EFB-derived lignin was subjected to an oxidative depolymerization using Cu(II) and Fe(III) mixed metal oxides catalyst supported on γ-Al2O3 or SiO2 as the catalyst in the presence of hydrogen peroxide. The highest percentage of total phenolic compounds of 63.87 wt% was obtained from microwave-induced oxidative degradation of K2CO3 extracted lignin catalyzed by Cu-Fe/SiO2 catalyst. Main products from the aforementioned condition included 27.29 wt% of 2,4-di-tert-butylphenol, 19.21 wt% of syringol, 9.36 wt% of acetosyringone, 3.69 wt% of acetovanillone, 2.16 wt% of syringaldehyde, and 2.16 wt% of vanillin. Although the total phenolic compound from Cu-Fe/Al2O3 catalyst was lower (49.52 wt%) compared with that from Cu-Fe/SiO2 catalyst (63.87 wt%), Cu-Fe/Al2O3 catalyst provided the greater selectivity of main two value-added products, syringol and acetosyrigone, at 54.64% and 23.65%, respectively (78.29% total selectivity of two products) from the NaOH extracted lignin. The findings suggested a promising method for syringol and acetosyringone production from the oxidative heterogeneous lignin depolymerization under low power intensity microwave heating within a short reaction time of 30 min.


Asunto(s)
Acetofenonas , Cobre/química , Hierro/química , Lignina/química , Microondas , Poaceae/química , Pirogalol/análogos & derivados , Acetofenonas/química , Acetofenonas/aislamiento & purificación , Óxido de Aluminio/química , Catálisis , Oxidación-Reducción , Pirogalol/química , Pirogalol/aislamiento & purificación
3.
Molecules ; 25(22)2020 Nov 20.
Artículo en Inglés | MEDLINE | ID: mdl-33233754

RESUMEN

Today, an alarming rise of bacterial gastroenteritis in humans resulting from consuming Campylobacter-tainted foods is being observed. One of the solutions for mitigating this issue may be the antibacterial activity of essential oils. In the present research, we propose to study the antibacterial activity against Campylobacter and other Gram-negative bacteria of Daucus carota essential oil and its active molecules. In addition, a few chemically synthesized molecules such as (E)-methylisoeugenol, Elemicin, and eugenol were also studied. The results showed that the essential oil itself and its most active component, (E)-methylisoeugenol, exhibited bactericidal effects. Similar effects were detected using purified and chemically synthesized molecules. Also, it was observed that the Daucus carota essential oil and its active molecules affected intracellular potassium and intracellular ATP contents in Campylobacter cells. Inhibition of the membrane bound FOF1-ATPase was also observed. Eventually, for the first time, the efflux mechanism of active molecules of Daucus carota essential oil was also identified in gamma proteobacteria and its specific antibacterial activity against Campylobacter jejuni was associated with the lack of this efflux mechanism in this species.


Asunto(s)
Antibacterianos/química , Antibacterianos/farmacología , Daucus carota/química , Aceites Volátiles/química , Aceites Volátiles/farmacología , Aceites de Plantas/química , Aceites de Plantas/farmacología , Adenosina Trifosfato , Campylobacter jejuni/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Farmacorresistencia Bacteriana/efectos de los fármacos , Bacterias Gramnegativas/efectos de los fármacos , Humanos , Pruebas de Sensibilidad Microbiana , Pirogalol/análogos & derivados , Pirogalol/síntesis química , Pirogalol/química
4.
Biosci Biotechnol Biochem ; 84(1): 31-36, 2020 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-31794330

RESUMEN

4-(2-Hydroxyphenethyl)-2,6-dimethoxyphenol, a bibenzyl, was isolated from the leaves of Empetrum nigrum var. japonicum, collected from Mount Tateyama. Japanese rock ptarmigans frequently eat the leaves and fruits of this plant. The structure of the bibenzyl was confirmed by NMR spectroscopic analysis and fully characterized. A synthesis of this compound was accomplished by coupling 2-hydroxyphenylacetic acid with syringaldehyde, decarboxylation of the resultant isoaurones, and hydrogenation of the double bond in the corresponding stilbene. This compound displayed cytotoxic activity against human cancer cells (HCT116 and Hela cells) and leukemia cells (HL-60 cells). The present study suggests that this plant serves as a source of biologically active natural products. Also, our findings provide information on the secondary metabolites in the diet of Japanese rock ptarmigans.


Asunto(s)
Bibencilos/síntesis química , Bibencilos/farmacología , Ericaceae/química , Extractos Vegetales/síntesis química , Extractos Vegetales/farmacología , Bacillus subtilis/efectos de los fármacos , Bibencilos/química , Bibencilos/aislamiento & purificación , Supervivencia Celular/efectos de los fármacos , Escherichia coli/efectos de los fármacos , Células HCT116 , Células HL-60 , Células HeLa , Humanos , Japón , Espectroscopía de Resonancia Magnética , Conformación Molecular , Neoplasias/metabolismo , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Hojas de la Planta/química , Pirogalol/análogos & derivados , Pirogalol/química
5.
Molecules ; 24(23)2019 Nov 27.
Artículo en Inglés | MEDLINE | ID: mdl-31783502

RESUMEN

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/farmacología
6.
J Agric Food Chem ; 67(29): 8243-8252, 2019 Jul 24.
Artículo en Inglés | MEDLINE | ID: mdl-31271289

RESUMEN

Elemicin, an alkenylbenzene constituent of natural oils of several plant species, is widely distributed in food, dietary supplements, and medicinal plants. 1'-Hydroxylation is known to cause metabolic activation of alkenylbenzenes leading to their potential toxicity. The aim of this study was to explore the relationship between elemicin metabolism and its toxicity through comparing the metabolic maps between elemicin and 1'-hydroxyelemicin. Elemicin was transformed into a reactive metabolite of 1'-hydroxyelemicin, which was subsequently conjugated with cysteine (Cys) and N-acetylcysteine (NAC). Administration of NAC could significantly ameliorate the elemicin- and 1'-hydroxyelemicin-induced cytotoxicity of HepG2 cells, while depletion of Cys with diethyl maleate (DEM) increased cytotoxicity. Recombinant human CYP screening and CYP inhibition experiments revealed that multiple CYPs, notably CYP1A1, CYP1A2, and CYP3A4, were responsible for the metabolic activation of elemicin. This study revealed that metabolic activation plays a critical role in elemicin cytotoxicity.


Asunto(s)
Pirogalol/análogos & derivados , Activación Metabólica , Biotransformación , Supervivencia Celular/efectos de los fármacos , Sistema Enzimático del Citocromo P-450/metabolismo , Células Hep G2 , Humanos , Hidroxilación , Estructura Molecular , Pirogalol/química , Pirogalol/metabolismo , Pirogalol/toxicidad
7.
J Agric Food Chem ; 67(15): 4328-4336, 2019 Apr 17.
Artículo en Inglés | MEDLINE | ID: mdl-30912427

RESUMEN

Myristicin is widely distributed in spices and medicinal plants. The aim of this study was to explore the role of metabolic activation of myristicin in its potential toxicity through a metabolomic approach. The myristicin- N-acetylcysteine adduct was identified by comparing the metabolic maps of myristicin and 1'-hydroxymyristicin. The supplement of N-acetylcysteine could protect against the cytotoxicity of myristicin and 1'-hydroxymyristicin in primary mouse hepatocytes. When the depletion of intracellular N-acetylcysteine was pretreated with diethyl maleate in hepatocytes, the cytotoxicity induced by myristicin and 1'-hydroxymyristicin was deteriorated. It suggested that the N-acetylcysteine adduct resulting from myristicin bioactivation was closely associated with myristicin toxicity. Screening of human recombinant cytochrome P450s (CYPs) and treatment with CYP inhibitors revealed that CYP1A1 was mainly involved in the formation of 1'-hydroxymyristicin. Collectively, this study provided a global view of myristicin metabolism and identified the N-acetylcysteine adduct resulting from myristicin bioactivation, which could be used for understanding the mechanism of myristicin toxicity.


Asunto(s)
Compuestos de Bencilo/metabolismo , Compuestos de Bencilo/toxicidad , Dioxolanos/metabolismo , Dioxolanos/toxicidad , Hepatocitos/efectos de los fármacos , Pirogalol/análogos & derivados , Acetilcisteína/química , Acetilcisteína/metabolismo , Activación Metabólica , Derivados de Alilbenceno , Animales , Compuestos de Bencilo/química , Supervivencia Celular/efectos de los fármacos , Células Cultivadas , Citocromo P-450 CYP1A1/metabolismo , Dioxolanos/química , Hepatocitos/citología , Humanos , Masculino , Ratones , Ratones Endogámicos C57BL , Pirogalol/química , Pirogalol/metabolismo , Pirogalol/toxicidad
8.
Food Chem ; 278: 119-126, 2019 Apr 25.
Artículo en Inglés | MEDLINE | ID: mdl-30583352

RESUMEN

In the western diet there is an oversupply of n-6 fatty acids. This adverse trend can be balanced by the consumption of rapeseed and flaxseed oils rich in α-linolenic acid (n-3). However, the high share of this fatty acid contributes to low oxidative stability of oil. Oxidation decreases n-3 fatty acid and other bioactive compounds contents, which adversely affects oil nutritional value. In this study, the impact of ferulic and sinapic acids vinyl derivatives on the fatty acids and oil terpenoids (sterols, tocols, carotenoids, squalene) retention at the end of induction period during accelerated oxidation of rapeseed and flaxseed cold-pressed oils was investigated. It was found that the use of 4-vinylsyringol (4-VS) or 4-vinylquaiacol (4-VQ) increased the retention of intact sterols and carotenoids (at least 2-fold) and squalene (at least 4-fold). The 4-VQ addition also inhibited the α-linolenic acid loss. Unfortunately, both phenolic derivatives favoured α-tocopherol decay in rapeseed oil.


Asunto(s)
Ácidos Grasos/química , Aceite de Linaza/química , Pirogalol/análogos & derivados , Aceite de Brassica napus/química , Terpenos/química , Carotenoides/análisis , Carotenoides/química , Ácidos Cumáricos/química , Ácidos Grasos/análisis , Manipulación de Alimentos/métodos , Aceite de Linaza/análisis , Oxidación-Reducción , Pirogalol/química , Aceite de Brassica napus/análisis , Terpenos/análisis , Ácido alfa-Linolénico/química
9.
Mar Drugs ; 16(11)2018 Nov 09.
Artículo en Inglés | MEDLINE | ID: mdl-30423960

RESUMEN

Ecklonia cava (E. cava) can alleviate vascular dysfunction in diseases associated with poor circulation. E. cava contains various polyphenols with different functions, but few studies have compared the effects of these polyphenols. Here, we comparatively investigated four major compounds present in an ethanoic extract of E. cava. These four major compounds were isolated and their effects were examined on monocyte-associated vascular inflammation and dysfunctions. Pyrogallol-phloroglucinol-6,6-bieckol (PPB) significantly inhibited monocyte migration in vitro by reducing levels of inflammatory macrophage differentiation and of its related molecular factors. In addition, PPB protected against monocyte-associated endothelial cell death by increasing the phosphorylations of PI3K-AKT and AMPK, decreasing caspase levels, and reducing monocyte-associated vascular smooth muscle cell proliferation and migration by decreasing the phosphorylations of ERK and AKT. The results of this study show that four compounds were effective for reduction of monocyte-associated vascular inflammation and dysfunctions, but PPB might be more useful for the treatment of vascular dysfunction in diseases associated with poor circulation.


Asunto(s)
Antiinflamatorios/farmacología , Dioxinas/farmacología , Monocitos/efectos de los fármacos , Phaeophyceae/química , Floroglucinol/farmacología , Extractos Vegetales/farmacología , Pirogalol/farmacología , Animales , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/uso terapéutico , Diferenciación Celular/efectos de los fármacos , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Dioxinas/química , Dioxinas/aislamiento & purificación , Dioxinas/uso terapéutico , Evaluación Preclínica de Medicamentos , Células Endoteliales/efectos de los fármacos , Células Endoteliales/fisiología , Macrófagos/efectos de los fármacos , Macrófagos/fisiología , Ratones , Monocitos/metabolismo , Monocitos/fisiología , Miocitos del Músculo Liso/efectos de los fármacos , Miocitos del Músculo Liso/fisiología , Floroglucinol/química , Floroglucinol/aislamiento & purificación , Floroglucinol/uso terapéutico , Extractos Vegetales/química , Pirogalol/química , Pirogalol/aislamiento & purificación , Pirogalol/uso terapéutico , Enfermedades Vasculares/tratamiento farmacológico
10.
Biochem Pharmacol ; 154: 148-160, 2018 08.
Artículo en Inglés | MEDLINE | ID: mdl-29684378

RESUMEN

Toll-like receptor 2 (TLR2) induces early inflammatory responses to pathogen and damage-associated molecular patterns trough heterodimerization with either TLR1 or TLR6. Since overstimulation of TLR2 signaling is linked to several inflammatory and metabolic diseases, TLR2 antagonists may provide therapeutic benefits for the control of inflammatory conditions. We present virtual screening for the identification of novel TLR2 modulators, which combines analyses of known ligand sets with structure-based approaches. The 13 identified compounds were pharmacologically characterized in HEK293-hTLR2 cells, THP-1 macrophages and peripheral blood mononuclear cells for their ability to inhibit TLR2-mediated responses. Four out of 13 selected compounds show concentration-dependent activity, representing a hit rate of 31%. The most active compound is the pyrogallol derivative MMG-11 that inhibits both TLR2/1 and TLR2/6 signaling and shows a higher potency than the previously discovered CU-CPT22. Concentration ratio analysis identified both compounds as competitive antagonists of Pam3CSK4- and Pam2CSK4-induced responses. Schild plot analysis yielded apparent pA2 values of 5.73 and 6.15 (TLR2/1), and 5.80 and 6.65 (TLR2/6) for CU-CPT22 and MMG-11, respectively. MMG-11 neither shows cellular toxicity nor interference with signaling induced by other TLR agonists, IL-1ß or TNF. Taken together, we demonstrate that MMG-11 is a potent and selective TLR2 antagonist with low cytotoxicity rendering it a promising pharmacological tool for the investigation of TLR signaling and a suitable lead structure for further chemical optimization.


Asunto(s)
Antioxidantes/química , Antioxidantes/farmacología , Simulación del Acoplamiento Molecular/métodos , Pirogalol/química , Pirogalol/farmacología , Receptor Toll-Like 2/antagonistas & inhibidores , Antioxidantes/metabolismo , Supervivencia Celular/efectos de los fármacos , Supervivencia Celular/fisiología , Cristalización , Relación Dosis-Respuesta a Droga , Evaluación Preclínica de Medicamentos/métodos , Células HEK293 , Humanos , Estructura Secundaria de Proteína , Estructura Terciaria de Proteína , Pirogalol/metabolismo , Relación Estructura-Actividad , Receptor Toll-Like 2/metabolismo
11.
Sci Rep ; 7(1): 12576, 2017 10 03.
Artículo en Inglés | MEDLINE | ID: mdl-28974710

RESUMEN

Hexane, dichloromethane and methanol extracts of the roots of Piper sarmentosum Roxb. were screened for toxicity towards Sitophilus oryzae (L.), Rhyzopertha dominica (F.), and Plodia interpunctella (Hübner) and the hexane extract exhibited the highest mortality percentage. Bioassay-guided fractionation of the hexane extract resulted in the isolation of asaricin 1, isoasarone 2, and trans-asarone 3. Asaricin 1 and isoasarone 2 were the most toxic compounds to Sitophilus oryzae, Rhyzopertha dominica, and Plodia interpunctella. Sitophilus oryzae and Rhyzopertha dominica exposed to asaricin 1 and isoasarone 2 required the lowest median lethal time. Insecticidal activity of trans-asarone 3 showed consistent toxicity throughout the 60 days towards all three insects as compared to asaricin 1 and isoasarone 2. Asaricin 1 and isoasarone 2 at different doses significantly reduced oviposition and adult emergence of the three insects in treated rice. Trans-asarone 3 had lowest toxicity with highest LC and LT values in all tested insects relative to its mild oviposition inhibition and progeny activity. Moreover, asaricin 1 and isoasarone 2 significantly inhibited acetylcholinesterase in comparison with trans-asarone 3 and the control. Acetylcholinesterase inhibition of Rhyzopertha dominica and Plodia interpunctella by asaricin 1 and isoasarone 2 were lower than that of Sitophilus oryzae, which correlated with their higher resistance.


Asunto(s)
Anisoles/farmacología , Compuestos de Bencilo/farmacología , Inhibidores de la Colinesterasa/farmacología , Dioxolanos/farmacología , Piper/química , Pirogalol/análogos & derivados , Acetilcolinesterasa/química , Derivados de Alilbenceno , Animales , Anisoles/química , Compuestos de Bencilo/química , Inhibidores de la Colinesterasa/química , Escarabajos/efectos de los fármacos , Dioxolanos/química , Insecticidas/química , Insecticidas/farmacología , Extractos Vegetales/química , Extractos Vegetales/farmacología , Raíces de Plantas/química , Pirogalol/química , Pirogalol/farmacología
12.
Free Radic Biol Med ; 106: 228-235, 2017 05.
Artículo en Inglés | MEDLINE | ID: mdl-28223196

RESUMEN

In this study, the mechanism of the xanthine oxidase (XO) inhibitory activity of pyrogallol, the main inhibitor found in roasted coffee, was investigated. Pyrogallol was unstable and readily converted to purpurogallin in a pH 7.4 solution, a physiological model of human body fluids. The XO inhibitory activity of the produced purpurogallin was higher than that of pyrogallol, as evidenced by comparing their IC50 values (0.2µmolL-1 for purpurogallin, 1.6µmolL-1 for pyrogallol). The XO activity of pyrogallol was enhanced by pre-incubation in pH 7.4 solution. Although the initial XO inhibitory activity of 4-methylpyrogallol was weak (IC50 33.3µmolL-1), its XO inhibitory activity was also enhanced by pre-incubation in the pH 7.4 solution. In contrast, 5-methylpyrogallol, which could not be transformed into corresponding purpurogallin derivatives, did not show XO inhibitory activity before or after incubation in pH 7.4 solution. Molecular docking simulations clarified that purpurogallins have stronger affinities for XO than corresponding pyrogallols. These results revealed that the potent XO inhibitory activity seemingly observed in pyrogallol is actually derived from its chemical conversion, under alkaline conditions, into purpurogallin.


Asunto(s)
Benzocicloheptenos/química , Pirogalol/metabolismo , Xantina Oxidasa/química , Alopurinol , Benzocicloheptenos/metabolismo , Café/química , Humanos , Simulación del Acoplamiento Molecular , Oxidación-Reducción , Pirogalol/química , Xantina Oxidasa/antagonistas & inhibidores
13.
Int J Biol Macromol ; 94(Pt A): 585-593, 2017 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-27769934

RESUMEN

Radioprotective effects of the water-soluble polyphenolic glycoconjugates, isolated from flowers of Sanguisorba officinalis L.(SO) and Erigeron canadensis L.(EC), and from leaves of Fragaria vesca L. (FV) and Rubus plicatus Whe. Et N. E. (RP), against γ-radiation-induced toxicity in human peripheral blood lymphocytes were investigated. Cell treatment with glycoconjugates (1, 5 and 25µg/mL) prior exposure to 10/15Gy radiation resulted in concentration-dependent reduction of DNA damage including oxidative DNA lesions (comet assay), substantial inhibition of lipid peroxidation (TBARS) and restoration of superoxide dismutase and S-glutathione transferase activities. Glycoconjugates isolated from SO and EC ensured better protection versus these from RP and FV, with the SO product potential comparable to that of the reference quercetin. Strong antioxidant/radioprotective activity of the SO and EC glycoconjugates could be attributed to high abundance of syringol-type and ferulic acid units in their matrices, respectively. Moreover, polyphenolic glycoconjugates (25µg/mL), including RP and FV products, significantly decreased DNA damage when applied post-radiation suggesting their modulating effects on DNA repair pathways. Preliminary data on the glycoconjugate phenolic structural units, based on GLC/MS of the products of pyrolysis and in situ methylation, in relation to application of plant products as potential radioprotectors is promising and deserves further investigation.


Asunto(s)
Antioxidantes/farmacología , Asteraceae/química , Glicoconjugados/farmacología , Leucocitos Mononucleares/efectos de los fármacos , Protectores contra Radiación/farmacología , Rosaceae/química , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Ensayo Cometa , Ácidos Cumáricos/análisis , Ácidos Cumáricos/química , Fragmentación del ADN/efectos de los fármacos , Fragmentación del ADN/efectos de la radiación , Reparación del ADN/efectos de los fármacos , Reparación del ADN/efectos de la radiación , Rayos gamma , Glutatión Transferasa/metabolismo , Glicoconjugados/química , Glicoconjugados/aislamiento & purificación , Humanos , Leucocitos Mononucleares/citología , Leucocitos Mononucleares/metabolismo , Leucocitos Mononucleares/efectos de la radiación , Extractos Vegetales/química , Cultivo Primario de Células , Pirogalol/análogos & derivados , Pirogalol/análisis , Pirogalol/química , Quercetina/farmacología , Protectores contra Radiación/química , Protectores contra Radiación/aislamiento & purificación , Superóxido Dismutasa/metabolismo , Sustancias Reactivas al Ácido Tiobarbitúrico/metabolismo
14.
Food Chem ; 196: 347-54, 2016 Apr 01.
Artículo en Inglés | MEDLINE | ID: mdl-26593500

RESUMEN

Tea catechins as a member of flavan-3-ols subclass with the same skeleton may behave differentially. This study investigated the chemical conversions of 8 catechins under heat treatment with the involvement of epimerization, hydrolysis and oxidation/condensation reactions. Three reactions were enhanced as temperature increased from 30 °C to 90 °C. The epimerization of non-gallated catechins was favored by epi-configuration but hindered by pyrogallol moiety, and the hydrolysis reaction of gallated catechins was facilitated by pyrogallol moiety. Epicatechin and epigallocatechin had the lowest thermostabilities due to epimerization and oxidation/condensation reactions respectively. Sufficient O2 was not a precondition for the occurrence of chemical conversions of catechins under heat treatment. Non-enzymatic oligomerization occurred to epi type catechins and catechin under heat treatment, and dehydrodicatechins A were mainly responsible for the browning of epicatechin and catechin solutions. The evidence of generation of catechin oligomers provides a novel way to explain sensory change of tea and relevant products during thermal processing.


Asunto(s)
Catequina/análogos & derivados , Catequina/química , Calor , Té/química , Estabilidad de Medicamentos , Hidrólisis , Oxidación-Reducción , Pirogalol/química
15.
Planta Med ; 81(10): 798-803, 2015 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-26125546

RESUMEN

Duguetia gardneriana, popularly known in the Brazilian northeast as "jaquinha", is a species belonging to the family Annonaceae. The aim of this work was to assess the chemical composition and antitumor properties of the essential oil from the leaves of D. gardneriana in experimental models. The chemical composition of the essential oil was analyzed via gas chromatography-flame ionization detector and gas chromatography-mass spectrometry. In vitro cytotoxic activity was determined in cultured tumor cells, and in vivo antitumor activity was assessed in B16-F10-bearing mice. The identified compounds were ß-bisabolene (80.99%), elemicin (8.04%), germacrene D (4.15%), and cyperene (2.82%). The essential oil exhibited a cytotoxic effect, with IC50 values of 16.89, 19.16, 13.08, and 19.33 µg/mL being obtained for B16-F10, HepG2, HL-60, and K562 cell lines, respectively. On the other hand, ß-bisabolene was inactive in all of the tested tumor cell lines (showing IC50 values greater than 25 µg/mL). The in vivo analysis revealed tumor growth inhibition rates of 5.37-37.52% at doses of 40 and 80 mg/kg/day, respectively. Herein, the essential oil from the leaves of D. gardneriana presented ß-bisabolene as the major constituent and showed cytotoxic and antitumor potential.


Asunto(s)
Annonaceae/química , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Aceites Volátiles/farmacología , Adulto , Animales , Línea Celular Tumoral/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales/métodos , Humanos , Masculino , Ratones Endogámicos C57BL , Sesquiterpenos Monocíclicos , Aceites Volátiles/química , Hojas de la Planta/química , Aceites de Plantas/química , Aceites de Plantas/farmacología , Pirogalol/análogos & derivados , Pirogalol/química , Pirogalol/farmacología , Sesquiterpenos/química , Sesquiterpenos/farmacología , Sesquiterpenos de Germacrano/farmacología , Ensayos Antitumor por Modelo de Xenoinjerto
16.
J Food Prot ; 78(4): 772-7, 2015 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-25836404

RESUMEN

Water-distilled essential oil from Illicium henryi (Illiciaceae) root bark was analyzed by gas chromatography-mass spectrometry. Thirty-four compounds, accounting for 97.86% of the total oil, were identified. The main components of the essential oil of I. henryi root bark were safrole (46.12%), myristicin (20.39%), and 1,8-cineole (6.17%), followed by α-cadinol (3.784%) and linalool (3.22%). The essential oil had higher levels of phenylpropanoids (66.89%) than of monoterpenoids (14.83%) and sesquiternoids (16.14%). Three constituents were isolated from the oil based on bioactivity fractionation. The essential oil possessed fumigant toxicity against booklice (Liposcelis bostrychophila), with a 50% lethal concentration (LC50) of 380.39 µg/liter of air, while the two isolated constituents myristicin and safrole had LC50s of 121.95 and 322.54 µg/liter, respectively. Another constituent, 1,8-cineole, showed weaker toxicity, with an LC50 of 1,120.43 µg/liter. The essential oil also exhibited contact toxicity against L. bostrychophila, with an LC50 of 96.83 µg/cm(2). Myristicin (LC50, 18.74 µg/cm(2)) and safrole (LC50, 69.28 µg/cm(2)) exhibited stronger acute toxicity than 1,8-cineole (LC50, 1,049.41 µg/cm(2)) against the booklice. The results indicated that the essential oil and its constituent compounds have potential for development into natural insecticides for control of psocids in stored grains.


Asunto(s)
Illicium/química , Insectos , Insecticidas/química , Aceites Volátiles/química , Aceites de Plantas/química , Raíces de Plantas/química , Monoterpenos Acíclicos , Derivados de Alilbenceno , Animales , Compuestos de Bencilo/química , Ciclohexanoles/química , Dioxolanos/química , Eucaliptol , Cromatografía de Gases y Espectrometría de Masas , Dosificación Letal Mediana , Monoterpenos/química , Pirogalol/análogos & derivados , Pirogalol/química , Safrol/química , Terpenos/química
17.
Appl Microbiol Biotechnol ; 99(2): 611-22, 2015 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-25467926

RESUMEN

Pyroligneous acid (PA) is a complex highly oxygenated aqueous liquid fraction obtained by the condensation of pyrolysis vapors, which result from the thermochemical breakdown or pyrolysis of plant biomass components such as cellulose, hemicellulose, and lignin. PA produced by the slow pyrolysis of plant biomass is a yellowish brown or dark brown liquid with acidic pH and usually comprises a complex mixture of guaiacols, catechols, syringols, phenols, vanillins, furans, pyrans, carboxaldehydes, hydroxyketones, sugars, alkyl aryl ethers, nitrogenated derivatives, alcohols, acetic acid, and other carboxylic acids. The phenolic components, namely guaiacol, alkyl guaiacols, syringol, and alkyl syringols, contribute to the smoky odor of PA. PA finds application in diverse areas, as antioxidant, antimicrobial, antiinflammatory, plant growth stimulator, coagulant for natural rubber, and termiticidal and pesticidal agent; is a source for valuable chemicals; and imparts a smoky flavor for food.


Asunto(s)
Biomasa , Preparaciones de Plantas/química , Terpenos/análisis , Catecoles/química , Celulosa/química , Fenómenos Químicos , Aromatizantes/química , Guayacol/química , Calor , Lignina/química , Fenoles/química , Polisacáridos/química , Pirogalol/análogos & derivados , Pirogalol/química , Madera/química
18.
Gene ; 555(2): 438-47, 2015 Jan 25.
Artículo en Inglés | MEDLINE | ID: mdl-25447898

RESUMEN

Fruit ripening associated full length cDNA of a peroxidase from papaya was cloned and heterologously expressed. The expressed peroxidase was activated by in-vitro re-folding in the presence of hemin and calcium. The purified recombinant peroxidase exhibited broad substrate affinity in the order of o-dianisidine>pyrogallol>guaiacol and was found to be a homotetramer of 155kDa with each subunit having a size of 38kDa. The basis of the distinctive preferences for various substrates was investigated through in-silico molecular modeling approaches. Thus, when the modeled papaya peroxidase-heme complex was docked with these substrates, the in-silico binding efficiency was found to be in agreement with those of wet lab results with the involvement of Arg37, Phe40, His41, Pro137, Asn138, His139, His167, and Phe239 as the common interacting residues in all the cases. However, the binding of the different substrates were found to be associated with conformational changes in the peroxidase. Thus, in the case of o-dianisidine (the most efficient substrate), the protein was folded in the most compact fashion when compared to guaiacol (the least efficient substrate). Protein function annotation analyses revealed that the papaya peroxidase may have biological roles in oxidation-reduction processes, stresses, defense responses etc. In order to further validate its role in lignifications, the papaya peroxidase was compared with a lignin biosynthetic peroxidase from Leucaena leucocephala, a tree legume. Thus, based on 3D structure superimposition and docking, both peroxidases exhibited a great extent of similarity suggesting the papaya peroxidase having a role in lignification (defense response) too. The predicted functions of papaya peroxidase in defense response and lignification were further validated experimentally using qRT-PCR analyses and measurement of oxidation of coniferyl alcohol.


Asunto(s)
Carica/enzimología , Peroxidasas/fisiología , Proteínas de Plantas/fisiología , Secuencia de Aminoácidos , Carica/fisiología , Cromatografía de Afinidad , Clonación Molecular , ADN Complementario/metabolismo , Dianisidina/química , Escherichia coli/metabolismo , Guayacol/química , Hemo/química , Concentración de Iones de Hidrógeno , Simulación del Acoplamiento Molecular , Datos de Secuencia Molecular , Pliegue de Proteína , Estructura Secundaria de Proteína , Estructura Terciaria de Proteína , Pirogalol/química , Reacción en Cadena en Tiempo Real de la Polimerasa , Proteínas Recombinantes/metabolismo , Especificidad por Sustrato , Temperatura
19.
Nat Prod Commun ; 9(10): 1531-4, 2014 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-25522554

RESUMEN

The chemical composition of Vietnamese oil samples of the aerial parts of Clausena indica (Dalz.) Oliver and C. anisum-olens (Blanco) Merryll have been investigated using a combination of chromatographic and spectroscopic techniques. C. indica essential oil contained mainly terpinolene (53.9 and 56.1%), and myristicin (17.9 and 7.3%), whereas the major components of C. anisun-olens essential were citronellal (22.8%), geranial (21.4%) and neral (16.8%). The compositions of the investigated samples have been compared with those of essential oils from various origins.


Asunto(s)
Clausena/química , Aceites Volátiles/química , Derivados de Alilbenceno , Compuestos de Bencilo/química , Monoterpenos Ciclohexánicos , Dioxolanos/química , Pirogalol/análogos & derivados , Pirogalol/química , Terpenos/química
20.
Artículo en Inglés | MEDLINE | ID: mdl-24759779

RESUMEN

The present study reports the use of Mimusops elengi (M. elengi) fruit extract for the synthesis of silver nanoparticles (Ag NPs). The synthesized Ag NPs was initially noticed through visual color change from yellow to reddish brown and further confirmed by surface plasmonic resonance (SPR) band at 429 nm using UV-Visible spectroscopy. Morphology and size of Ag NPs was determined by Transmission Electron Microscopy (TEM) analysis. X-ray Diffraction (XRD) study revealed crystalline nature of Ag NPs. The prolonged stability of Ag NPs was due to capping of oxidized polyphenols which was established by Fourier Transform Infrared Spectroscopy (FTIR) study. The polyphenols present in M. elengi fruit extract was analyzed by High Pressure Liquid Chromatography (HPLC) and the results revealed the presence of ascorbic acid, gallic acid, pyrogallol and resorcinol. In order to study the role of these polyphenols in reducing Ag+ ions to Ag NPs, analyses of extracts before reduction and after reduction were carried out. In addition, the synthesized Ag NPs were tested for antibacterial and antioxidant activities against Staphylococcus aureus (S. Aureus) and Escherichia coli (E. coli). Ag NPs showed good antimicrobial activity against both gram positive (S. aureus) and gram negative (E. coli) bacteria. It also showed good antioxidant activity as compared to ascorbic acid as standard antioxidant.


Asunto(s)
Antiinfecciosos/química , Antioxidantes/química , Mimusops/química , Extractos Vegetales/química , Semillas/química , Plata/química , Ácido Ascórbico/química , Cromatografía Líquida de Alta Presión , Escherichia coli/efectos de los fármacos , Ácido Gálico/química , Iones/química , Nanopartículas del Metal/química , Pruebas de Sensibilidad Microbiana , Microscopía Electrónica de Transmisión , Pirogalol/química , Resorcinoles/química , Espectroscopía Infrarroja por Transformada de Fourier , Staphylococcus aureus/efectos de los fármacos , Difracción de Rayos X
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