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1.
Food Funct ; 15(8): 4122-4139, 2024 Apr 22.
Artigo em Inglês | MEDLINE | ID: mdl-38573168

RESUMO

The health-promoting effects of berries have attracted attention due to the possible application of their extracts as functional ingredients in food products. Natural deep eutectic solvents (NADESs) are a new generation of environmentally friendly solvents for the extraction of natural products, and they are green alternatives to organic solvents, and they can improve the solubility, stability, and bioavailability of isolated biocompounds. In this study, an efficient eco-friendly method was used for the extraction of phenolic compounds from different berries: chokeberries, blueberries, and black goji berries with a range of eutectic solvents consisting of hydrogen bond acceptors (HBAs) such as choline chloride, L-proline, L-glycine, and L-lysine and hydrogen bond donors (HBDs) such as malic, citric, tartaric, lactic and succinic acids, glucose and glycerol. The obtained results indicated the ability of NADESs towards selective extraction of phenolics; the eutectic system choline chloride : malic acid showed selective extraction of anthocyanins, while choline chloride : glycerol and choline chloride : urea showed selectivity towards flavonoids and phenolic acids. The methodology for screening of the NADES extraction performance, which included chromatographic profiling via high-performance thin layer chromatography combined with chemometrics and spectrophotometric essays, allowed effective assessment of optimal eutectic solvents for isolation of different groups of phenolics. Great antioxidant and antimicrobial activities of extracts, along with the green nature of eutectic solvents, enable NADES berry extracts to be used as "green-labelled" functional foods or ingredients.


Assuntos
Solventes Eutéticos Profundos , Frutas , Alimento Funcional , Fenóis , Extratos Vegetais , Frutas/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Fenóis/química , Fenóis/farmacologia , Fenóis/isolamento & purificação , Solventes Eutéticos Profundos/química , Antioxidantes/farmacologia , Antioxidantes/química , Mirtilos Azuis (Planta)/química , Flavonoides/farmacologia , Flavonoides/química , Flavonoides/isolamento & purificação , Coriandrum/química
2.
Sci Rep ; 14(1): 9182, 2024 Apr 22.
Artigo em Inglês | MEDLINE | ID: mdl-38649422

RESUMO

In order to obtain high yield pomelo peel pectin with better physicochemical properties, four pectin extraction methods, including hot acid extraction (HAE), microwave-assisted extraction (MAE), ultrasound-assisted extraction, and enzymatic assisted extraction (EAE) were compared. MAE led to the highest pectin yield (20.43%), and the lowest pectin recovery was found for EAE (11.94%). The physicochemical properties of pomelo peel pectin obtained by different methods were also significantly different. Pectin samples obtained by MAE had the highest methoxyl content (8.35%), galacturonic acid content (71.36%), and showed a higher apparent viscosity, thermal and emulsion stability. The pectin extracted by EAE showed the highest total phenolic content (12.86%) and lowest particle size (843.69 nm), showing higher DPPH and ABTS scavenging activities than other extract methods. The pectin extracted by HAE had the highest particle size (966.12 nm) and degree of esterification (55.67%). However, Fourier-transform infrared spectroscopy showed that no significant difference occurred among the different methods in the chemical structure of the extracted pectin. This study provides a theoretical basis for the industrial production of pomelo peel pectin.


Assuntos
Citrus , Ácidos Hexurônicos , Pectinas , Pectinas/química , Pectinas/isolamento & purificação , Citrus/química , Viscosidade , Tamanho da Partícula , Micro-Ondas , Espectroscopia de Infravermelho com Transformada de Fourier , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Fracionamento Químico/métodos , Fenômenos Químicos , Frutas/química , Antioxidantes/química , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Fenóis/análise , Fenóis/química , Fenóis/isolamento & purificação , Esterificação
3.
Ultrason Sonochem ; 105: 106852, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38518410

RESUMO

The "ultrasonic-assisted extraction (UAE)" method was utilized in this work to assess how different process parameters affected the yield and recovery of phenolic compounds from the leaf of Commiphora gileadensis, which is one of the medicinal plants with a variety of biological functions. Its leaf is used for a various of therapeutic applications, such as the treatment of bacterial infections, inflammation, and wound healing. The "One-Factor-At-a-Time (OFAT)" approach was employed to examine the impacts of various UAE process parameters on the process of extraction, which include time of extraction, sample/solvent ratio, ultrasonic frequency, and solvent (ethanol) concentration. The extracts were then investigated for the presence of several phytochemicals using analytical techniques such as "Gas Chromatography-Mass Spectroscopy (GC-MS)" and "Fourier Transform Infrared Spectroscopy (FTIR)" studies. The findings showed that the maximum extraction yield, the total phenolic content (TPC), and the total flavonoids content (TFC) of the ethanolic extract of the leaves of C. gileadensis using the UAE method were at 31.80 ± 0.41 %, 96.55 ± 2.81 mg GAE/g d.w. and 31.66 ± 2.01 mg QE/g d.w. accordingly under a procedure duration of 15 min, ultrasonic frequency of 20 kHz, solvent/sample ratio of 1:20 g/mL, and solvent concentration of 40 % v/v. The leaves extract of C. gileadensis included 25 phenolic compounds that were previously unreported, and GC-MS analysis confirmed their presence. Hence, it follows that the UAE technique can successfully extract the phytochemicals from C. gileadensis for a variety of therapeutic uses.


Assuntos
Fracionamento Químico , Commiphora , Fenóis , Folhas de Planta , Ondas Ultrassônicas , Commiphora/química , Folhas de Planta/química , Fenóis/isolamento & purificação , Fracionamento Químico/métodos , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Solventes/química
4.
Food Chem ; 448: 139104, 2024 Aug 01.
Artigo em Inglês | MEDLINE | ID: mdl-38547711

RESUMO

Legume proteins can be induced to form amyloid-like fibrils upon heating at low pH, with the exact conditions greatly impacting the fibril characteristics. The protein extraction method may also impact the resulting fibrils, although this effect has not been carefully examined. Here, the fibrillization of lentil protein prepared using various extraction methods and the corresponding fibril morphology were characterized. It was found that an acidic, rather than alkaline, protein extraction method was better suited for producing homogeneous, long, and straight fibrils from lentil proteins. During alkaline extraction, co-extracted phenolic compounds bound proteins through covalent and non-covalent interactions, contributing to the formation of heterogeneous, curly, and tangled fibrils. Recombination of isolated phenolics and proteins (from acidic extracts) at alkaline pH resulted in a distinct morphology, implicating a role for polyphenol oxidase also in modifying proteins during alkaline extraction. These results help disentangle the complex factors affecting legume protein fibrillization.


Assuntos
Lens (Planta) , Fenóis , Proteínas de Plantas , Lens (Planta)/química , Fenóis/química , Fenóis/isolamento & purificação , Proteínas de Plantas/química , Proteínas de Plantas/isolamento & purificação , Concentração de Íons de Hidrogênio , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Amiloide/química , Fracionamento Químico/métodos
5.
Molecules ; 28(17)2023 Aug 25.
Artigo em Inglês | MEDLINE | ID: mdl-37687080

RESUMO

Skin cancer is a condition characterized by the abnormal growth of skin cells, primarily caused by exposure to ultraviolet (UV) radiation from the sun or artificial sources like tanning beds. Different types of skin cancer include melanoma, basal cell carcinoma, and squamous cell carcinoma. Despite the advancements in targeted therapies, there is still a need for a safer, highly efficient approach to preventing and treating cutaneous malignancies. Spices have a rich history dating back thousands of years and are renowned for their ability to enhance the flavor, taste, and color of food. Derived from various plant parts like seeds, fruits, bark, roots, or flowers, spices are important culinary ingredients. However, their value extends beyond the culinary realm. Some spices contain bioactive compounds, including phenolic compounds, which are known for their significant biological effects. These compounds have attracted attention in scientific research due to their potential health benefits, including their possible role in disease prevention and treatment, such as cancer. This review focuses on examining the potential of spice-derived phenolic compounds as preventive or therapeutic agents for managing skin cancers. By compiling and analyzing the available knowledge, this review aims to provide insights that can guide future research in identifying new anticancer phytochemicals and uncovering additional mechanisms for combating skin cancer.


Assuntos
Fenóis , Compostos Fitoquímicos , Neoplasias Cutâneas , Especiarias , Neoplasias Cutâneas/tratamento farmacológico , Neoplasias Cutâneas/prevenção & controle , Fenóis/isolamento & purificação , Fenóis/farmacologia , Fenóis/uso terapêutico , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/uso terapêutico , Humanos
6.
Molecules ; 28(17)2023 Aug 29.
Artigo em Inglês | MEDLINE | ID: mdl-37687138

RESUMO

This research aimed to study the dynamic changes in phenolic antioxidants between the germ and the rest of the germinated seed of wheat and spelt and to evaluate the whole grain flour from germinated seeds as a functional supplement. Longer germination resulted in higher TPC, DPPH, and ABTS values when considering the entire germinated seed, while the optimal germination time was not consistent when considering the germ and the remaining germinated seed separately. While in the germinated seed (without germ) the majority of TPC was determined to be bound phenolics (up to 92%), the extractable form dominated in the germ (up to 69%). The most abundant phenolic antioxidants in germinated wheat and spelt seeds, trans-ferulic acid, cis-ferulic acid, and p-coumaric acid, increased significantly with germination. Only breads with 5% germinated spelt or wheat flour were suitable for the production of a food product, showing higher extractable TPC, antioxidant activity, individual phenolic acids, and improved specific volume, and were preferred because of their appearance, aroma, and color. The PCA biplot showed that the addition of 15% and 30% germinated flours had the greatest positive impact on phenolic properties, while breads with the addition of 5% germinated flour had the greatest positive impact on specific volume and color.


Assuntos
Antioxidantes , Pão , Valor Nutritivo , Fenóis , Sementes , Triticum , Triticum/química , Antioxidantes/química , Antioxidantes/isolamento & purificação , Germinação , Sementes/química , Pão/análise , Solubilidade , Fenóis/química , Fenóis/isolamento & purificação
7.
J Ethnopharmacol ; 310: 116378, 2023 Jun 28.
Artigo em Inglês | MEDLINE | ID: mdl-36924865

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: The traditional use of Prunus species against skin diseases and especially for skin lightning cosmeceutical purposes is widespread in many cultures. Prunus mahaleb L. is a well known food plant and used in the baking industry for flavoring. The fruit kernels (endocarp) are used in India for hyperpigmentation. AIM OF THE STUDY: To investigate the chemical composition with the antimelanogenesis effect of P. mahaleb seed and kernel extracts and isolated compounds. MATERIALS AND METHODS: Isolation studies performed from the methanol extracts obtained from kernels and structures were determined using NMR and MS analysis. Antimelanogenesis effect was determined by mushroom tyrosinase assay, cellular tyrosinase assay and melanin content assay using B16F10 murine melanoma cells. RESULTS: Five cinnamic acid derivatives were isolated and their structures (2-O-ß-glucopyranosyloxy-4-methoxy-hydrocinnamic acid (1), cis-melilotoside (2), dihydromelilotoside (3), trans-melilotoside (4), 2-O-ß-glucosyloxy-4-methoxy trans-cinnamic acid (5)) were elucidated using advanced spectroscopic methods. Mushroom tyrosinase enzyme inhibition of extracts, fractions and pure compounds obtained from P. mahaleb kernels were investigated and structure-activity relationship revealed. According to a detailed, comprehensive and validated LC-MS/MS technique analysis, vanilic acid (41.407 mg/g), protocatechuic acid (8.992 mg/g) and ferulic acid (4.962 mg/g) in the kernel ethylacetate fraction; quinic acid (14.183 mg/g), fumaric acid (8.349 mg/g) and aconitic acid (5.574 mg/g) were found as major phenolic compounds in the water fraction. The correlation of trace element copper content in extracts and fractions with mushroom enzyme activity was determined. By examining the enzyme kinetics of the compounds with effective cinnamic acid derivatives, inhibition types and enzyme binding constants Ki were calculated. Compounds 1,3 and 5 exhibited high noncompetitive tyrosinase inhibitory activity against L-tyrosine substrates, with IC50 values of 0.22, 0.31 and 0.37 mM respectively. In addition compounds 1, 3 and 5 showed dose-dependent inhibitory effects on intracellular tyrosinase and melanin levels in α-melanocyte-stimulating hormone (α-MSH)-induced B16F10 melanoma cells. CONCLUSIONS: Potent tyrosinase inhibitory compounds and extracts of P. mahaleb kernels suggest that it could be a new, non-toxic and inexpensive resource for the cosmeceutical industry and in skin diseases associated with hyperpigmentation.


Assuntos
Cinamatos , Melanoma , Monofenol Mono-Oxigenase , Fenóis , Animais , Camundongos , Cosmecêuticos , Inibidores Enzimáticos/farmacologia , Inibidores Enzimáticos/química , Melaninas/metabolismo , Melanoma/tratamento farmacológico , Melanoma/metabolismo , Monofenol Mono-Oxigenase/efeitos dos fármacos , Fenóis/química , Fenóis/isolamento & purificação , Fenóis/farmacologia , Prunus , Cinamatos/química , Cinamatos/isolamento & purificação , Cinamatos/farmacologia , Antineoplásicos/farmacologia
8.
Phytochemistry ; 205: 113514, 2023 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-36379319

RESUMO

Nine undescribed geranylgeranylated derivatives (chinensens A-G), including malic acid derivative (A) and phenolic derivatives (B-E), as well as two pairs of enantiomers, [(R), (S)]-chinensens F and [(R), (S)]-chinensens G, were isolated from the roots of Rhus chinensis Mill. Their structures were elucidated by UV, IR, HRESIMS, 1D and 2D NMR spectra, as well as optical rotations. The 95% EtOH extract (95% EXT, 500 mg/kg, p. o.) of the roots of Rhus chinensis and the 95% EtOH fraction (95% FRA, 500 mg/kg, p. o.) from the microporous resin column significantly alleviated indomethacin-induced or water immersion-restraint stress-induced damage in rat gastric mucosa with inhibitory rates from 53% to 89%. The racemic mixture (chinensen G) and its enantiomers [(R), (S)]-chinensens G showed weak activities against H+,K+-ATPase (20%-24%) at a concentration of 0.1 mM, respectively.


Assuntos
Compostos Fitoquímicos , Rhus , Animais , Ratos , Rhus/química , Raízes de Plantas/química , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Mucosa Gástrica/efeitos dos fármacos , Fenóis/química , Fenóis/isolamento & purificação
9.
Food Chem ; 397: 133718, 2022 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-35940099

RESUMO

The untargeted metabolomics approach was used to compare the chemical profiles of acerola (Malpighia emarginata DC.) pomace extracts. The effect of drying the raw material before subcritical water extraction (SWE) at different temperatures on the yield, phenolic content, and in vitro antioxidant activity was evaluated. The results were compared with those obtained via Soxhlet and the findings suggest that SWE saves time (15 min) and solvent for extracting valuable components as compared to Soxhlet (6 h). An increase in temperature significantly improved the extraction yield (23.9 to 33.4 %), phenolic content (119.1 to 362 mgGAEg-1), and antioxidant activity, and higher values were obtained with SWE as compared to Soxhlet. The most abundant compounds detected by UPLC-ESI-QTOF-MS were ascorbic acid, kaempferol, quercetin, and isorhamnetin. The investigation of different moisture contents in the SWE showed promising results for eliminating the drying operation, saving time and energy, and obtaining highly concentrated phenolic-rich by-products.


Assuntos
Antioxidantes , Malpighiaceae , Extratos Vegetais , Água , Antioxidantes/química , Antioxidantes/isolamento & purificação , Ácido Ascórbico , Malpighiaceae/química , Metabolômica , Fenóis/análise , Fenóis/isolamento & purificação , Extratos Vegetais/química , Rutina , Água/química
10.
J Food Sci ; 87(7): 2831-2846, 2022 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-35661363

RESUMO

Buckwheat hulls are discarded as waste, although they have more phenolic compounds than buckwheat groats. The antioxidant activities of buckwheat hull extracts prepared with water, 50% ethanol, and 100% ethanol were investigated in bulk oil, oil-in-water (O/W), and water-in-oil (W/O) emulsions. The relationship between the phenolic compositions of the extracts and their antioxidant activities in the three different lipid systems was also evaluated. Fifty percent ethanol extract had the highest total phenolic content (327 mg gallic acid equivalent [GAE]/g extract) followed by water and 100% ethanol extracts (211 and 163 mg GAE/g extract, respectively). The total oxidation rate (k) was not significantly different among the bulk oils added with the buckwheat hull extracts. However, in the O/W emulsion, the k was more reduced by the 50% and 100% ethanol extracts than by the water extract at the concentration of 100 µg GAE/g (2.9, 2.8, and 3.7 Totox/day, respectively). The k of the W/O emulsion was more reduced by the 100% ethanol extract than by the water and 50% ethanol extract at the concentration of 100 µg GAE/g (3.8, 4.7, and 4.5 Totox/day, respectively). Multivariate statistical analysis revealed that the contents of phenolic acids and their derivatives were the highest in the water extract among the extracts, while the contents of flavonoid glycosides and methylated polyphenols were the highest in the 50% and 100% ethanol extracts, respectively. The results suggest that flavonoid glycosides and methylated polyphenols could be potential candidates for retarding the oxidation of the emulsion system. PRACTICAL APPLICATION: Buckwheat hull extracts could retard lipid oxidation. Flavonoid glycosides and methylated polyphenols in buckwheat hull extracts may have an antioxidative effect on lipids. Thus, buckwheat hulls could be used as an antioxidant in lipid systems, as flavonoid glycosides and methylated polyphenols are properly extracted from buckwheat hulls.


Assuntos
Antioxidantes , Fagopyrum , Óleos , Fenóis , Antioxidantes/análise , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Emulsões/química , Etanol/química , Fagopyrum/química , Flavonoides/análise , Ácido Gálico/análise , Glicosídeos/análise , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Óleos/química , Fenóis/análise , Fenóis/isolamento & purificação , Fenóis/farmacologia , Extratos Vegetais/análise , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Polifenóis/análise , Polifenóis/isolamento & purificação , Polifenóis/farmacologia , Sementes/química
11.
Anal Methods ; 14(26): 2623-2630, 2022 07 07.
Artigo em Inglês | MEDLINE | ID: mdl-35735028

RESUMO

In this study, a three-dimensional adsorbent was developed based on graphene oxide/AgO nanoparticles over interconnected nickel foam (GO/AgO@Ni foam) for rapid and efficient vortex assisted floating solid phase extraction of bisphenol A in canned food products prior to high performance liquid chromatography with a fluorescence detector. The analytical techniques scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and Fourier transform infrared (FT-IR) were used for characterization of the synthetized GO/AgO@Ni foam. The effect of proficiency factors including pH, foam size, vortexing time, salt addition, sample volume, desorption type and volume, and desorption time on the extraction efficiency of bisphenol A were explored through the matrix match method. Under the above experimental conditions, the figures of merit of the method were acquired as LODs (S/N = 3) of 0.18-0.84 µg kg-1, LOQs of 0.61-2.81 µg kg-1 (S/N = 10), linear ranges of 0.5-500 µg kg-1, and enrichment factors of 235.5-244.9. The inter-day precision values (RSD%, n = 7) of 2.5-3.6 and the intra-day precision (%) of (5 days and seven replicates for each day) 2.8-3.8 were achieved for bisphenol A at a concentration of 50 µg kg-1. The relative recoveries of 94.0% to 99.6% were obtained for the canned food samples.


Assuntos
Compostos Benzidrílicos , Alimentos em Conserva , Grafite , Nanopartículas Metálicas , Fenóis , Extração em Fase Sólida , Adsorção , Compostos Benzidrílicos/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Fluorescência , Concentração de Íons de Hidrogênio , Microscopia Eletrônica de Varredura , Fenóis/isolamento & purificação , Extração em Fase Sólida/métodos , Espectroscopia de Infravermelho com Transformada de Fourier , Fatores de Tempo
12.
Food Res Int ; 157: 111381, 2022 07.
Artigo em Inglês | MEDLINE | ID: mdl-35761637

RESUMO

This work evaluated two emerging techniques in extracting phenolic compounds from Tahiti lime pomace - pressurized liquid extraction (PLE) and ultrasound-assisted extraction (UAE). PLE was performed at different temperatures (60 - 110 °C) and times (5 - 40 min), and UAE was carried out varying ultrasound power (160 - 792 W), time (2 - 10 min), and solvent to feed mass ratio (20 - 40 kg solvent/kg dried pomace). Both used ethanol and water (3:1, wt.) as the solvent. The effects of these variables were evaluated on global extraction yield, polyphenols, hesperidin, narirutin yields, and antioxidant capacity. PLE was strongly affected by temperature and extraction time, and the highest temperature (110 °C) provided the best results for global yield, total phenolic, and ORAC, except for hesperidin and narirutin, which were not significative affected by temperature. UAE revealed a weak dependency on power, S/F, and time; however, the lowest power level significantly increased the yields compared to no power application. Thus, P = 480 W, t = 6 min, and S/F = 30 was chosen as the best condition in the UAE in terms of overall extraction yield, total phenolics, specific phenolics, antioxidant capacities, and solvent and energy expenditures. UAE mechanisms were investigated by comparing with heated and stirred maceration, and scanning electron microscopy suggested that total phenolic yield was influenced by mechanisms that only ultrasound can provide. Micrographics confirmed the cavitation effect on Tahiti lime pomace particles' surface. To sum up, PLE resulted in the highest yields and antioxidant capacity, followed by UAE.


Assuntos
Antioxidantes/química , Citrus , Hesperidina , Compostos de Cálcio/química , Hesperidina/química , Hesperidina/isolamento & purificação , Óxidos/química , Fenóis/química , Fenóis/isolamento & purificação , Solventes
13.
Molecules ; 27(4)2022 Feb 21.
Artigo em Inglês | MEDLINE | ID: mdl-35209235

RESUMO

Since the middle of the last century, marine organisms have been identified as producers of chemically and biologically diverse secondary metabolites which have exerted various biological activities including anticancer, anti-inflammatory, antioxidant, antimicrobial, antifouling and others. This review primarily focuses on the marine phenolic compounds and their derivatives with potent anticancer activity, isolated and/or modified in the last decade. Reports on the elucidation of their structures as well as biosynthetic studies and total synthesis are also covered. Presented phenolic compounds inhibited cancer cells proliferation or migration, at sub-micromolar or nanomolar concentrations (lamellarins D (37), M (38), K (39), aspergiolide B (41), fradimycin B (62), makulavamine J (66), mayamycin (69), N-acetyl-N-demethylmayamycin (70) or norhierridin B (75)). In addition, they exhibited anticancer properties by a diverse biological mechanism including induction of apoptosis or inhibition of cell migration and invasive potential. Finally, phlorotannins 1-7 and bromophenols 12-29 represent the most researched phenolic compounds, of which the former are recognized as protective agents against UVB or gamma radiation-induced skin damages. Finally, phenolic metabolites were assorted into six main classes: phlorotannins, bromophenols, flavonoids, coumarins, terpenophenolics, quinones and hydroquinones. The derivatives that could not be attributed to any of the above-mentioned classes were grouped in a separate class named miscellaneous compounds.


Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Organismos Aquáticos/química , Fenóis/química , Fenóis/farmacologia , Antineoplásicos/isolamento & purificação , Organismos Aquáticos/metabolismo , Produtos Biológicos/química , Produtos Biológicos/isolamento & purificação , Produtos Biológicos/farmacologia , Humanos , Redes e Vias Metabólicas , Fenóis/isolamento & purificação , Fenóis/metabolismo , Relação Estrutura-Atividade
14.
Bioorg Med Chem Lett ; 59: 128528, 2022 03 01.
Artigo em Inglês | MEDLINE | ID: mdl-34999211

RESUMO

The aqueous extract of the leaves of Odontonema strictum, a plant from tropical regions, is used by traditional physicians in Burkina Faso for its antihypertensive properties. Verbascoside and isoverbascoside, known phenylpropanoid glycosides with high solubility in water, have been isolated from the leaves. We evaluated their antioxidant properties in vitro by radical scavenging using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and hydrogen peroxide (H2O2). Verbascoside and isoverbascoside demonstrated high levels of DPPH radical scavenging activity, with IC50 values of 0.09 ± 0.03 µg/mL and 0.16 ± 0.07 µg/mL, respectively, compared to 0.05 ± 0.0 µg/mL for ascorbic acid as a control. These two phenylpropanoid glycosides were also more potent (2.6 ± 0.36 µg/mL and 3.0 ± 0.01 µg/mL) in scavenging H2O2 than the ascorbic acid control (4.1 ± 0.97 µg/mL). This is the first time that the antioxidant properties of verbascoside and isoverbascoside from O. strictum have been evaluated. These results can explain the use of this plant for hypertension in folk medicine.


Assuntos
Acanthaceae/química , Sequestradores de Radicais Livres/farmacologia , Glucosídeos/farmacologia , Fenóis/farmacologia , Folhas de Planta/química , Compostos de Bifenilo/antagonistas & inibidores , Relação Dose-Resposta a Droga , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/isolamento & purificação , Glucosídeos/química , Glucosídeos/isolamento & purificação , Peróxido de Hidrogênio/antagonistas & inibidores , Estrutura Molecular , Fenóis/química , Fenóis/isolamento & purificação , Picratos/antagonistas & inibidores , Relação Estrutura-Atividade
15.
Molecules ; 27(2)2022 Jan 14.
Artigo em Inglês | MEDLINE | ID: mdl-35056847

RESUMO

Olive leaf is a rich source of phenolic compounds with numerous activities related to skin health and appearance. In this study, a green extraction method was developed using eco-friendly solvents: polypropylene glycol (PPG), lactic acid (LA), and water. The optimal extraction conditions were established, including solvent, extraction time, technique (magnetic stirrer vs. ultrasound-assisted extraction), and herbal material/solvent ratio. The composition of the solvent mixture was optimized using a mixture design. The content of phenolic compounds, including oleuropein and verbascoside, was determined using high-performance liquid chromatography (HPLC) and spectrophotometric methods. Using different extraction conditions, three extracts were prepared and their phytochemical compositions and antioxidant and skin-related bioactivities were investigated. The extracts were excellent inhibitors of elastase, collagenase, tyrosinase, and lipoxygenase. The best activity was shown by the extract richest in phenolics and prepared using magnetic-stirrer-assisted extraction for 20 min, with 0.8 g of herbal material extracted in 10 mL of PPG/LA/water mixture (28.6/63.6/7.8, w/w/w), closely followed by the extract prepared using the same extraction conditions but with 0.42 g of herbal material. The investigated PPG/LA/water mixtures contributed to the overall enzyme-inhibitory activity of the extracts. The prepared extracts were appropriate for direct use in cosmetic products, thus saving the time and energy consumption necessary for the evaporation of conventional solvents.


Assuntos
Cosmecêuticos/farmacologia , Inibidores Enzimáticos/farmacologia , Olea/química , Fenóis/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Folhas de Planta/química , Cosmecêuticos/isolamento & purificação , Ácido Láctico/química , Extratos Vegetais/isolamento & purificação , Polímeros/química , Propilenoglicóis/química
16.
Biomed Pharmacother ; 145: 112415, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34775236

RESUMO

Oxidative stress is considered the main cause of cellular damage in a number of neurodegenerative disorders. One suitable ways to prevent cell damage is the use of the exogenous antioxidant capacity of natural products, such as microalgae. In the present study, four microalgae extracts, isolated from the Persian Gulf, were screened to analyze their potential antioxidant activity and free radical scavenging using ABTS, DPPH, and FRAP methods. The methanolic extracts (D1M) of green microalgae derived from Chlorella sp. exhibited potent free radical scavenging activity. In order to characterize microalgae species, microscopic observations and analysis of the expression of 18S rRNA were performed. The antioxidant and neuroprotective effects of D1M on H2O2-induced toxicity in PC12 cells were investigated. The results demonstrated that D1M significantly decreased the release of nitric oxide (NO), formation of intracellular reactive oxygen species (ROS), and the level of malondialdehyde (MDA), whereas it enhanced the content of glutathione (GSH), and activity of heme oxygenase 1 (HO-1), NAD(P)H: quinone oxidoreductase 1 (NQO1), and catalase (CAT) in PC12 cells exposed to H2O2. The pretreatment of D1M improved cell viability as measured by the MTT assay and invert microscopy, reduced cell apoptosis as examined by flow cytometry analysis, increased mitochondrial membrane potential (MMP), and diminished caspase-3 activity. The GC/MS analysis revealed that D1M ingredients have powerful antioxidant and anti-inflammatory compounds, such as butylated hydroxytoluene (BHT), 2,4-di-tert-butyl-phenol (2,4-DTBP), and phytol. These results suggested that Chlorella sp. extracts have strong potential to be applied as neuroprotective agents, for the treatment of neurodegenerative disorders.


Assuntos
Antioxidantes/farmacologia , Chlorella/química , Doenças Neurodegenerativas/prevenção & controle , Fármacos Neuroprotetores/farmacologia , Animais , Antioxidantes/isolamento & purificação , Apoptose/efeitos dos fármacos , Hidroxitolueno Butilado/isolamento & purificação , Hidroxitolueno Butilado/farmacologia , Sobrevivência Celular/efeitos dos fármacos , Sequestradores de Radicais Livres/isolamento & purificação , Sequestradores de Radicais Livres/farmacologia , Peróxido de Hidrogênio/toxicidade , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Doenças Neurodegenerativas/fisiopatologia , Fármacos Neuroprotetores/isolamento & purificação , Estresse Oxidativo/efeitos dos fármacos , Células PC12 , Fenóis/isolamento & purificação , Fenóis/farmacologia , Fitol/isolamento & purificação , Fitol/farmacologia , Ratos , Espécies Reativas de Oxigênio/metabolismo
17.
Fitoterapia ; 156: 105089, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34800595

RESUMO

Eight previously undescribed compounds, two quinones (1-2), one sesquiterpene (3), and five phenol compounds (4-8), including three enantiomers (6a, 7a, and 8a), along with three corresponding known enantiomers (6b-8b) were isolated from the aerial parts of Morinda umbellata L. Their structures were elucidated by 1D and 2D NMR spectroscopy, X-ray diffraction, and experimental and calculated ECD spectra, respectively. Compound 5 was found to have weak cytotoxity, which inhibited the growth of seven human cancer cell lines (A2780, HeLa, MCF-7, BGC-823, H7420, Ketr3 and SW 1990) with IC50 values from 13.3 to 15.1 µM.


Assuntos
Citotoxinas/toxicidade , Morinda/química , Fenóis/toxicidade , Quinonas/toxicidade , Sesquiterpenos/toxicidade , Linhagem Celular Tumoral , Cromatografia Líquida de Alta Pressão , Cristalografia por Raios X , Citotoxinas/isolamento & purificação , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Fenóis/isolamento & purificação , Componentes Aéreos da Planta/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/toxicidade , Quinonas/isolamento & purificação , Sesquiterpenos/isolamento & purificação
18.
Artigo em Inglês | MEDLINE | ID: mdl-34864606

RESUMO

A rapid and simple fabric phase sorptive extraction (FPSE) procedure is developed for the simultaneous extraction of four monomers (Bisphenol A, BPA; Triethylene glycol dimethacrylate, TEGDMA; Urethane dimethacrylate, UDMA; Bisphenol A-glycidyl methacrylate, BisGMA) in human saliva, prior to the determination by high pressure liquid chromatography with an ultraviolet-visible detector. FPSE is a green sample preparation technique, harmonized with the principles of Green Analytical Chemistry (GAC), which utilizes a flexible surface, such as cellulose, chemically coated with a polymeric material using sol-gel technology. FPSE membranes are characterized by superior chemical stability and any solvent or solvent mixture can be used for elution. Among twelve different sol-gel coated membranes, an FPSE membrane coated with sol-gel polytetrahydrofuran (sol-gel PTHF) was found optimum to extract four target compounds from saliva samples, which were first centrifuged. Parameters with most significant impact on the extraction efficiency of FPSE including elution solvent, utilization of magnetic stirring, extraction time have been comprehensively studied and optimized. The studied compounds' separation was carried out by a Perfect Sil 120 ODS-2 chromatographic column (250 mm × 4.0 mm, 5 µm), using a mobile phase constituting of acetonitrile-water 70:30 % v/v (isocratic elution). The total analysis time was 10 min. Detection was achieved by an ultraviolet-visible detector at 220 nm. The method was validated in terms of sensitivity, linearity, trueness, precision, selectivity and stability of samples. For all four compounds, the limit of detection and the limit of quantification were 0.075 ng/µL and 0.25 ng/µL, respectively. Relative recovery rates were between 90.0 and 106.7%, while RSD values were <8.1 and 12% for interday and intraday repeatability, respectively. Youden & Steiner approach was applied to study method's ruggedness and reusability of the media was tested, which enhanced the green nature of technique.


Assuntos
Compostos Benzidrílicos/análise , Cromatografia Líquida/métodos , Materiais Dentários/química , Fenóis/análise , Saliva/química , Compostos Benzidrílicos/química , Compostos Benzidrílicos/isolamento & purificação , Química Verde , Humanos , Modelos Lineares , Fenóis/química , Fenóis/isolamento & purificação , Reprodutibilidade dos Testes , Sensibilidade e Especificidade , Espectrofotometria Ultravioleta , Têxteis
19.
Chem Biodivers ; 19(1): e202100804, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34799976

RESUMO

Chemical investigation on the deep-sea-derived fungus Chaetomium globosum led to the isolation of nine compounds. By extensive analyses of the 1D and 2D NMR as well as HR-ESI-MS spectra, their structures were elucidated as xylariol A (1), 1,3-dihydro-4,5,6-trihydroxy-7-methylisobenzofuran (2), epicoccone B (3), epicoccolide B (4), chaetoglobosin G (5), chaetoglobosin Fex (6), cochliodone A (7), cochliodone B (8), and chaetoviridin A (9), assorting as four phenolics (1-4), two cytochalosans (5-6), and three azaplilones (7-9). Compounds 1-3 were firstly reported from C. globosum. Under the concentrations of 20 µg/mL, 1, 2, and 3 exhibited potent in vitro anti-HIV activity with the inhibition rates of 70 %, 75 %, and 88 %, respectively.


Assuntos
Fármacos Anti-HIV/química , Chaetomium/química , Água do Mar/microbiologia , Fármacos Anti-HIV/isolamento & purificação , Fármacos Anti-HIV/farmacologia , Linhagem Celular , Chaetomium/metabolismo , Genes Reporter/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Fenóis/química , Fenóis/isolamento & purificação , Fenóis/farmacologia , Espectrometria de Massas por Ionização por Electrospray
20.
Food Chem ; 371: 131116, 2022 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-34583181

RESUMO

Porophyllum ruderale subsp. ruderale is a food product used for seasoning in Central and Southern America. The present research aimed to investigate the chemical composition of an extract prepared from aerial parts of P. ruderale using UHPLC-DAD-MS/MS, to isolate and identify major natural products present in the extract, and to furtherly investigate their anti-inflammatory activity in vitro. Twenty-five compounds were detected and characterized using UV-Vis and MS data. All characterized compounds were quantified. Ten major phenolics were isolated and identified by NMR. One previously undescribed natural product was isolated and established as 1-O-(4-hydroxy-3,5-dimethoxy)benzoyl-6-O-galloyl-ß-d-glucose (12). Anti-inflammatory activity was evaluated based on the influence of the extract and isolated compounds on the TLR4-dependent secretion of IL-8 and TNF-α by human primary neutrophils in vitro. Phenolic acids, and caffeic acid derivatives in particular, contributed to the extract's bioactivity.


Assuntos
Coriandrum , Fenóis , Anti-Inflamatórios/farmacologia , Bolívia , Humanos , Fenóis/isolamento & purificação , Fenóis/farmacologia , Extratos Vegetais/farmacologia , Espectrometria de Massas em Tandem
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