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1.
Microb Pathog ; 190: 106635, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38579934

RESUMEN

The plant Erythrina indica comes under Fabaceae family, mainly used for used in traditional medicine as nervine sedative, antiepileptic, antiasthmatic, collyrium in opthalmia, antiseptic. Current study focused synthesize of silver nanoparticles (AgNPs) by E. indica leaf ethanol extract. The green-synthesized AgNPs underwent characterization using multiple analytical techniques, including UV-visible, FTIR, DLS, SEM, TEM, XRD, and EDX, and estimation of their antioxidant activity and antimicrobial activity. Phytochemical analysis identified alkaloids, tannins, saponins, flavonoids, and phenols as secondary metabolites. The Total Phenol Content (TPC) was determined to be 237.35 ± 2.02 mg GAE-1, indicating a substantial presence of phenolic compounds. The presence of AgNPs was verified through UV-Visible analysis at 420 nm, and FT-IR revealed characteristic phenolic functional groups. DLS analysis indicated a narrow size distribution (polydispersity index - PDI: 3.47%), with SEM revealing spherical AgNPs of approximately 20 nm. TEM showed homogeneous, highly polycrystalline AgNPs with lattice spacing at 0.297. XRD analysis demonstrated crystallinity and purity, with distinct reflection peaks corresponding to miller indices of JCPDS card no. 01 087 1473. In vitro, AgNPs exhibited robust antioxidant activity like; DPPH, ABTS, and H2O2, surpassing E. indica-assisted synthesis. ABTS assay indicated higher antioxidant activity (81.94 ± 0.05%) for AgNPs at 734 nm, while E. indica extraction showed 39.67 ± 0.07%. At 532 nm, both E. indica extraction (57.71 ± 0.11%) and AgNPs (37.41 ± 0.17%) exhibited H2O2 scavenging. Furthermore, AgNPs displayed significant antimicrobial properties, inhibiting Staphylococcus aureus (15.7 ± 0.12 mm) and Candida albicans (10.7 ± 0.17 mm) byfor the concentration of 80 µg/mL. Through the characterizations underscore of the potential of Erythrina indica-synthesized AgNPs, rich in polyphenolic compounds, for pharmacological, medical, biological applications and antipyretic properties.


Asunto(s)
Antiinfecciosos , Antioxidantes , Erythrina , Nanopartículas del Metal , Pruebas de Sensibilidad Microbiana , Fitoquímicos , Extractos Vegetales , Hojas de la Planta , Plata , Plata/química , Plata/farmacología , Antioxidantes/farmacología , Antioxidantes/química , Nanopartículas del Metal/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Erythrina/química , Antiinfecciosos/farmacología , Antiinfecciosos/química , Hojas de la Planta/química , Fitoquímicos/farmacología , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Espectroscopía Infrarroja por Transformada de Fourier , Fenoles/química , Fenoles/farmacología , Difracción de Rayos X , Flavonoides/química , Flavonoides/farmacología , Flavonoides/análisis , Tecnología Química Verde , Candida albicans/efectos de los fármacos , Taninos/farmacología , Taninos/química
2.
Food Chem ; 448: 139117, 2024 Aug 01.
Artículo en Inglés | MEDLINE | ID: mdl-38608398

RESUMEN

This study aimed to determine the impact of supplementation with probiotically fermented chickpea (Cicer arietinum L) seeds on the quality parameters and functional characteristics of wheat bread. The addition of chickpea seeds caused significant changes in the chemical composition of the control wheat bread. The legume-supplemented products exhibited higher values of a* and b* color parameters and higher hardness after 24 h of storage than the control. The application of fermented or unfermented chickpeas contributed to an increase in total polyphenol and flavonoid contents, iron chelating capacity, and antioxidant properties of the final product. The variant containing unfermented seeds had the highest riboflavin content (29.53 ± 1.11 µg/100 g d.w.), Trolox equivalent antioxidant capacity (227.02 ± 7.29 µmol·L-1 TX/100 g d.w.), and free radical scavenging activity (71.37 ± 1.30 % DPPH inhibition). The results of this preliminary research have practical importance in the production of innovative bakery products with potential properties of functional food.


Asunto(s)
Antioxidantes , Pan , Cicer , Fermentación , Probióticos , Cicer/química , Pan/análisis , Antioxidantes/química , Antioxidantes/análisis , Probióticos/análisis , Probióticos/química , Semillas/química , Flavonoides/análisis , Flavonoides/química , Polifenoles/química , Polifenoles/análisis , Alimentos Funcionales/análisis , Triticum/química , Triticum/metabolismo
3.
PLoS One ; 19(4): e0298194, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-38625916

RESUMEN

INTRODUCTION: Paeonia lactiflora contains diverse active constituents and exhibits various pharmacological activities. However, only partial identification of biologically active substances from P. lactiflora has been achieved using low-throughput techniques. Here, the roots of P. lactiflora, namely, Fenyunu (CK), Dafugui (DFG), and Red Charm (HSML), were studied. The primary and secondary metabolites were investigated using ultrahigh-performance liquid chromatography-electrospray ionization-tandem mass spectrometry (UPLC-ESIMS/MS). METHODS: The chemical compounds and categories were detected using broadly targeted UPLC-MS/MS. Principal component analysis (PCA), orthogonal partial least-squares discriminant analysis (OPLS-DA), and hierarchical clustering analysis (HCA) were carried out for metabolites of different varieties of P. lactiflora. RESULTS: A total of 1237 compounds were detected and classified into 11 categories. HCA, PCA, and OPLS-DA of these metabolites indicated that each variety of P. lactiflora was clearly separated from the other groups. Differential accumulated metabolite analysis revealed that the three P. lactiflora varieties contained 116 differentially activated metabolites (DAMs) involved in flavonoid, flavone, and flavonol metabolism. KEGG pathway analysis revealed that, in 65 pathways, 336 differentially abundant metabolites (DMs) were enriched in the CK and DFG groups; moreover, the type and content of terpenoids were greater in the CK group than in the DFG group. The CK and HSML groups contained 457 DMs enriched in 61 pathways; the type and amount of flavonoids, terpenoids, and tannins were greater in the CK group than in the HSML group. The DFG and HSML groups contained 497 DMs enriched in 65 pathways; terpenoids and alkaloids were more abundant in the HSML variety than in the DFG variety. CONCLUSIONS: A total of 1237 compounds were detected, and the results revealed significant differences among the three P. lactiflora varieties. Among the three P. lactiflora varieties, phenolic acids and flavonoids composed the largest and most diverse category of metabolites, and their contents varied greatly. Therefore, CK is suitable for medicinal plant varieties, and DFG and HSML are suitable for ornamental plant varieties. Twelve proanthocyanidin metabolites likely determined the differences in color among the three varieties.


Asunto(s)
Paeonia , Cromatografía Liquida , Espectrometría de Masas en Tándem/métodos , Metabolómica/métodos , Flavonoides/química , Cromatografía Líquida de Alta Presión/métodos , Terpenos/metabolismo
4.
Food Funct ; 15(8): 4122-4139, 2024 Apr 22.
Artículo en Inglés | MEDLINE | ID: mdl-38573168

RESUMEN

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.


Asunto(s)
Disolventes Eutécticos Profundos , Frutas , Alimentos Funcionales , Fenoles , Extractos Vegetales , Frutas/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Fenoles/química , Fenoles/farmacología , Fenoles/aislamiento & purificación , Disolventes Eutécticos Profundos/química , Antioxidantes/farmacología , Antioxidantes/química , Arándanos Azules (Planta)/química , Flavonoides/farmacología , Flavonoides/química , Flavonoides/aislamiento & purificación , Coriandrum/química
5.
J Ethnopharmacol ; 330: 118195, 2024 Aug 10.
Artículo en Inglés | MEDLINE | ID: mdl-38641080

RESUMEN

ETHNOPHARMACOLOGICAL RELEVANCE: Licorice is a frequently used herbal medicine worldwide, and is used to treat cough, hepatitis, cancer and influenza in clinical practice of traditional Chinese medicine. Modern pharmacological studies indicate that prenylated flavonoids play an important role in the anti-tumor activity of licorice, especially the tumors in stomach, lung, colon and liver. Wighteone is one of the main prenylated flavonoids in licorice, and its possible effect and target against colorectal cancer have not been investigated. AIM OF THE STUDY: This study aimed to investigate the anti-colorectal cancer effect and underlying mechanism of wighteone. MATERIALS AND METHODS: SW480 human colorectal cancer cells were used to evaluate the in vitro anti-colorectal cancer activity and Akt regulation effect of wighteone by flow cytometry, phosphoproteomic and Western blot analysis. Surface plasmon resonance (SPR) assay, molecular docking and dynamics simulation, and kinase activity assay were used to investigate the direct interaction between wighteone and Akt. A nude mouse xenograft model with SW480 cells was used to verify the in vivo anti-colorectal cancer activity of wighteone. RESULTS: Wighteone inhibited phosphorylation of Akt and its downstream kinases in SW480 cells, which led to a reduction in cell viability. Wighteone had direct interaction with both PH and kinase domains of Akt, which locked Akt in a "closed" conformation with allosteric inhibition, and Gln79, Tyr272, Arg273 and Lys297 played the most critical role due to their hydrogen bond and hydrophobic interactions with wighteone. Based on Akt overexpression or activation in SW480 cells, further mechanistic studies suggested that wighteone-induced Akt inhibition led to cycle arrest, apoptosis and autophagic death of SW480 cells. Moreover, wighteone exerted in vivo anti-colorectal cancer effect and Akt inhibition activity in the nude mouse xenograft model. CONCLUSION: Wighteone could inhibit growth of SW480 cells through allosteric inhibition of Akt, which led to cell cycle arrest, apoptosis and autophagic death. The results contributed to understanding of the anti-tumor mechanism of licorice, and also provided a rationale to design novel Akt allosteric inhibitors for the treatment of colorectal cancer.


Asunto(s)
Antineoplásicos Fitogénicos , Neoplasias Colorrectales , Flavonoides , Glycyrrhiza , Ratones Desnudos , Proteínas Proto-Oncogénicas c-akt , Humanos , Proteínas Proto-Oncogénicas c-akt/metabolismo , Animales , Glycyrrhiza/química , Neoplasias Colorrectales/tratamiento farmacológico , Neoplasias Colorrectales/patología , Línea Celular Tumoral , Flavonoides/farmacología , Flavonoides/aislamiento & purificación , Flavonoides/uso terapéutico , Flavonoides/química , Antineoplásicos Fitogénicos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/uso terapéutico , Antineoplásicos Fitogénicos/aislamiento & purificación , Simulación del Acoplamiento Molecular , Proliferación Celular/efectos de los fármacos , Ensayos Antitumor por Modelo de Xenoinjerto , Regulación Alostérica/efectos de los fármacos , Ratones , Ratones Endogámicos BALB C , Apoptosis/efectos de los fármacos , Masculino
6.
Food Chem ; 448: 139125, 2024 Aug 01.
Artículo en Inglés | MEDLINE | ID: mdl-38537547

RESUMEN

In this study, the ultrasonic-microwave pretreatment was defined as a processing technology in the production of tribute citrus powder, and it could increase the flavonoid compounds in the processing fruit powder. A total of 183 upregulated metabolites and 280 downregulated metabolites were obtained by non-targeted metabolomics, and the differential metabolites was mainly involved in the pathways of flavonoid biosynthesis, flavone and flavonol biosynthesis. A total of 8 flavonoid differential metabolites were obtained including 5 upregulated metabolites (6"-O-acetylglycitin, scutellarin, isosakuranin, rutin, and robinin), and 3 downregulated metabolites (astragalin, luteolin, and (-)-catechin gallate) by flavonoids-targeted metabolomics. The 8 flavonoid differential metabolites participated in the flavonoid biosynthesis pathways, flavone and flavonol biosynthesis pathways, and isoflavonoid biosynthesis pathways. The results provide a reference for further understanding the relationship between food processing and food components, and also lay a basis for the development of food targeted-processing technologies.


Asunto(s)
Citrus , Flavonoides , Frutas , Metabolómica , Citrus/metabolismo , Citrus/química , Flavonoides/metabolismo , Flavonoides/química , Frutas/química , Frutas/metabolismo , Polvos/química , Polvos/metabolismo , Extractos Vegetales/química , Extractos Vegetales/metabolismo , Manipulación de Alimentos
7.
Acta Parasitol ; 69(1): 839-853, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38436864

RESUMEN

PURPOSE: During cystic echinococcosis surgery, the use of scolicidal agents such as hypertonic saline (20%) aims to reduce the risk of infection recurrence, but most of the used agents are associated with undesirable side effects. Therefore, the use of natural scolicidal agents such as medicinal plant extracts could reduce these medical issues. The present study aimed to compare in vitro the scolicidal activity between two extracts of the medicinal plant Myrtus communis from Algeria against Echinococcus granulosus sensu lato protoscoleces. METHODS: The ethanolic and aqueous extraction of plant leaves was performed. Phytochemical analysis by gas chromatography-tandem mass spectrometry (GC-MS/MS), determination of total phenolic and flavonoid contents, and in vitro antioxidant activity by DPPH were evaluated for both extracts. Finally, the in vitro scolicidal activity was tested by different concentrations. The viability was evaluated by the eosin exclusion test. RESULTS: The phytochemical analysis revealed 28 components for the ethanolic extract and 44 components for the aqueous extract. The major components were 2'-hydroxy-5'-methoxyacetophenone and 4-amino-2-methylphenol, respectively. The total phenolic and flavonoid contents were 45.9 ± 0.085 mg of gallic acid equivalent per g of extract (GAE/g E) and 16.5 ± 0.004 mg of quercetin equivalent per g (QE/g E) for the ethanolic extract, and 36.5 ± 0.016 mg GAE/g E and 18.2 ± 0.023 mg QE/g E for the aqueous extract, respectively. Furthermore, ethanolic and aqueous extracts of M. communis gave a value of IC50 = 0.009 ± 0.0004 mg/ml and IC50 = 0.012 ± 0.0003 mg/ml for the antioxidant activity, respectively. The in vitro scolicidal activity with concentrations of 50, 75, 100, and 150 mg/ml was tested for 5, 10, 15, and 30 min, and 5, 10, 15, 30, 60, 90, and 120 min for ethanolic and aqueous extracts, respectively. The mortality rate of protoscoleces at concentrations of 100 and 150 mg/ml was 98.8 and 100%, respectively, after 5 min of exposure to the ethanolic extract, while this rate was 100% at the same concentrations only after 60 min of exposure to the aqueous extract. CONCLUSIONS: The ethanolic extract showed a stronger scolicidal activity against E. granulosus s.l protoscoleces than the aqueous extract. In the future, other investigations are necessary to elucidate the mechanism of action and the possible toxicity on human cells. Moreover, experimental animal studies are required to investigate the efficacy of different extracts of this plant and its components as natural anti-parasitic alternatives for the treatment of human cystic echinococcosis.


Asunto(s)
Echinococcus granulosus , Myrtus , Extractos Vegetales , Hojas de la Planta , Extractos Vegetales/farmacología , Extractos Vegetales/química , Hojas de la Planta/química , Animales , Echinococcus granulosus/efectos de los fármacos , Myrtus/química , Argelia , Antioxidantes/farmacología , Antioxidantes/química , Fenoles/farmacología , Fenoles/análisis , Flavonoides/farmacología , Flavonoides/análisis , Flavonoides/química , Cromatografía de Gases y Espectrometría de Masas , Fitoquímicos/farmacología , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Equinococosis/tratamiento farmacológico , Equinococosis/parasitología
8.
Molecules ; 29(5)2024 Feb 20.
Artículo en Inglés | MEDLINE | ID: mdl-38474439

RESUMEN

The leaves of Chrysanthemum indicum L. are known to have various bioactive compounds; however, industrial use is extremely limited. To overcome this situation by producing high-quality leaves with high bioactive content, this study examined the environmental factors affecting the phytochemical content and antioxidant activity using C. indicum leaves collected from 22 sites in Kochi Prefecture, Japan. Total phenolic and flavonoid content in the dry leaves ranged between 15.0 and 64.1 (mg gallic acid g-1) and 2.3 and 11.4 (mg quercetin g-1), while the antioxidant activity (EC50) of the 50% ethanol extracts ranged between 28.0 and 123.2 (µg mL-1) in 1,1-Diphenyl-2-picrylhydrazyl radical scavenging assay. Among the identified compounds, chlorogenic acid and 1,5-dicaffeoylquinic acid were the main constituents in C. indicum leaves. The antioxidant activity demonstrated a positive correlation with 1,5-dicaffeoylquinic acid (R2 = 0.62) and 3,5-dicaffeoylquinic acid (R2 = 0.77). The content of chlorogenic acid and dicaffeoylquinic acid isomers varied significantly according to the effects of exchangeable magnesium, cation exchange capacity, annual temperature, and precipitation, based on analysis of variance. The habitat suitability map using the geographical information system and the MaxEnt model predicted very high and high regions, comprising 3.2% and 10.1% of the total area, respectively. These findings could be used in future cultivation to produce high-quality leaves of C. indicum.


Asunto(s)
Chrysanthemum , Cinamatos , Flavonoides , Flavonoides/química , Antioxidantes/química , Polifenoles/análisis , Ácido Clorogénico/análisis , Chrysanthemum/química , Hojas de la Planta/química , Extractos Vegetales/química
9.
Molecules ; 29(5)2024 Feb 28.
Artículo en Inglés | MEDLINE | ID: mdl-38474558

RESUMEN

The Hibiscus manihot L. (HML) Medic, an edible hibiscus of the Malvaceae family, is abundant with flavonoids. The study investigated how Rhizopus-arrhizus-31-assisted pretreatment affects the extraction and bioactivity of flavonoids from HML. The fiber structure of the fermented flavonoid sample (RFF) appears looser, more porous, and more disordered than the unfermented flavonoid sample (RUF). RFF demonstrates milder conditions and yields higher extraction rates. According to the Box-Behnken response surface optimization experiment, the optimal conditions for RFF include a material-liquid ratio of 1:41 g/mL, a 2 h extraction time, a 57% ethanol concentration, and an extraction temperature of 800 °C, resulting in a 3.69% extraction yield, which is 39.25% higher than that of RUF. Additionally, RFF exhibits greater activity than RUF in the radical-scavenging system. The IC50 values for DPPH, OH, and ABTS radicals are 83.43 µg/mL and 82.62 µg/mL, 208.38 µg/mL and 175.99 µg/mL, and 108.59 µg/mL and 75.39 µg/mL for RUF and RFF, respectively. UPLC-QTOF-MS analysis of the active components in the HML flavonoid sample revealed significant differences in the chromatograms of RUF and RFF, indicating that biofermentation led to substantial changes in composition and content from HML.


Asunto(s)
Hibiscus , Manihot , Flavonoides/química , Antioxidantes/química , Hibiscus/química , Extractos Vegetales/química , Rhizopus
10.
Molecules ; 29(5)2024 Feb 29.
Artículo en Inglés | MEDLINE | ID: mdl-38474601

RESUMEN

Three new phenols (1-3), one new cyclohexanol (4), two known phenols (5-6), and six known flavonoids (7-12) were isolated from the n-butanol of the 75% ethanol extract of all plants of Chimaphila japonica Miq. Among them, compound 5 was named and described in its entirety for the first time, and compounds 9 and 10 were reported in C. japonica for the first time. The structures of all compounds were confirmed using a comprehensive analysis of 1D and 2D NMR and HRESIMS data. Biological results show that compounds 4, 7, and 11 exhibited potent diuretic activity. The modes of interaction between the selected compounds and the target diuretic-related WNK1 kinase were investigated in a preliminary molecular docking study. These results provided insight into the chemodiversity and potential diuretic activities of metabolites in C. japonica.


Asunto(s)
Antioxidantes , Flavonoides , Simulación del Acoplamiento Molecular , Flavonoides/química , Antioxidantes/química , Fenoles/química , Extractos Vegetales/química
11.
Molecules ; 29(5)2024 Mar 03.
Artículo en Inglés | MEDLINE | ID: mdl-38474649

RESUMEN

The leaves of Agave angustifolia Haw. are the main agro-waste generated by the mezcal industry and are becoming an important source of bioactive compounds, such as phenolic compounds, that could be used in the food and pharmaceutical industries. Therefore, the extraction and identification of these phytochemicals would revalorize these leaf by-products. Herein, maceration and supercritical carbon dioxide (scCO2) extractions were optimized to maximize the phenolic and flavonoid contents and the antioxidant capacity of vegetal extracts of A. angustifolia Haw. In the maceration process, the optimal extraction condition was a water-ethanol mixture (63:37% v/v), which yielded a total phenolic and flavonoid content of 27.92 ± 0.90 mg EAG/g DL and 12.85 ± 0.53 µg QE/g DL, respectively, and an antioxidant capacity of 32.67 ± 0.91 (ABTS assay), 17.30 ± 0.36 (DPPH assay), and 13.92 ± 0.78 (FRAP assay) µM TE/g DL. Using supercritical extraction, the optimal conditions for polyphenol recovery were 60 °C, 320 bar, and 10% v/v. It was also observed that lower proportions of cosolvent decreased the polyphenol extraction more than pressure and temperature. In both optimized extracts, a total of 29 glycosylated flavonoid derivatives were identified using LC-ESI-QTof/MS. In addition, another eight novel compounds were identified in the supercritical extracts, showing the efficiency of the cosolvent for recovering new flavonoid derivatives.


Asunto(s)
Agave , Antioxidantes/química , Polifenoles/química , Fenoles/química , Flavonoides/química , Extractos Vegetales/química
12.
Chem Biodivers ; 21(5): e202400300, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38430215

RESUMEN

Sea buckthorn, a traditional medicinal plant, has been used for several years in China for the prevention and treatment of various diseases, a practice closely associated with its significant antioxidant activity. The aim of this study was to investigate the protective effects of sea buckthorn flavonoids on vascular endothelial cells in an oxidative stress environment. We isolated and extracted active compounds from sea buckthorn and investigated their impact on endothelial nitric oxide synthase (eNOS) activity through the PI3K/AKT-eNOS signaling pathway through a combination of network pharmacology and cellular experiments, elucidating the regulatory effects of these compounds on endothelial cell functions. Three flavonoids, named Fr.4-2-1, Fr.4-2-2 and Fr.4-2-3, were obtained from sea buckthorn. The results of network pharmacology indicated that they might exert their effects by regulating the PI3K-AKT signaling pathway. In vitro results showed that all three flavonoids were effective in alleviating the degree of oxidative stress in cells, among which Fr.4-2-1 exerted its antioxidant effects by modulating the PI3K/AKT-eNOS pathway. Flavonoids in sea buckthorn can effectively inhibit oxidative stress-induced cellular damage, preserving the integrity and functionality of endothelial cells, which is crucial for maintaining vascular health and function.


Asunto(s)
Flavonoides , Hippophae , Óxido Nítrico Sintasa de Tipo III , Estrés Oxidativo , Fosfatidilinositol 3-Quinasas , Proteínas Proto-Oncogénicas c-akt , Transducción de Señal , Hippophae/química , Óxido Nítrico Sintasa de Tipo III/metabolismo , Flavonoides/farmacología , Flavonoides/aislamiento & purificación , Flavonoides/química , Proteínas Proto-Oncogénicas c-akt/metabolismo , Estrés Oxidativo/efectos de los fármacos , Fosfatidilinositol 3-Quinasas/metabolismo , Transducción de Señal/efectos de los fármacos , Humanos , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Células Endoteliales/efectos de los fármacos , Células Endoteliales/metabolismo , Células Endoteliales de la Vena Umbilical Humana/efectos de los fármacos , Células Endoteliales de la Vena Umbilical Humana/metabolismo , Supervivencia Celular/efectos de los fármacos , Sustancias Protectoras/farmacología , Sustancias Protectoras/química , Sustancias Protectoras/aislamiento & purificación
13.
Phytochemistry ; 220: 114005, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38309451

RESUMEN

Chemical investigation of ethyl acetate bark extracts of Indigofera ammoxylum red and white phenotypes led to the bio-guided isolation of four previously undescribed flavonoids, named (2S,3R)-3',7-dihydroxy-4',6-dimethoxyflavanol (1), (2S,3R)-6-methoxy-7-hydroxyflavanol (2), 2',3',7-trihydroxy-4',6-dimethoxyisoflavone (7) and 2',5' -dimethoxy-4',5,7-trihydroxyisoflavanone (8), along with 14 known compounds (3-6 and 9-18). The previously undescribed structures were characterized based on NMR, HRESIMS, UV and IR data. Published spectroscopic data were used to deduce the structure of the known compounds. Eleven of the 18 isolated metabolites were evaluated for anti-inflammatory activity and cytotoxic activity against human liver carcinoma cells and human colon and colorectal adenocarcinoma cells. All tested compounds showed an anti-inflammatory activity (IC50 NO < 25 µg/mL), and compounds 2 and 3 were more selective than the positive control dexamethasone. Afromorsin (6) showed promising cytotoxic properties against both cancer cell lines (IC50 18.9 and 11.4 µg/mL). Feature-based molecular networking approach applied to bark and leaves extracts of the two phenotypes allowed to detect bioactive analogues, belonging to the families of flavones, isoflavones, flavanones, flavanols and flavonols, and to explore the chemodiversity of the species. The red and white phenotypes have a similar composition, whereas bark and leaves contain specific chemical entities. Finally, this approach highlighted a cluster of potentially bioactive and undescribed metabolites.


Asunto(s)
Flavanonas , Indigofera , Humanos , Flavonoides/química , Flavonoles , Extractos Vegetales/farmacología , Extractos Vegetales/química , Antiinflamatorios/farmacología , Estructura Molecular
14.
Chem Biodivers ; 21(4): e202400026, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38372467

RESUMEN

Ruta chalepensis L. is a versatile herb used in culinary arts and traditional medicine. The study aimed to determine the chemical composition of an ethanolic extract from R. chalepensis and the total phenolic and flavonoid content. Additionally, the extracts' antimicrobial and antioxidant activities were tested. The disc diffusion method and minimum inhibitory concentration (MIC) were used to test the antibacterial properties on four types of bacteria: Escherichia coli, Proteus penneri, Bacillus cereus, and Staphylococcus aureus. A colorimetric assay was used to evaluate the total phenolic and flavonoid content, and the DPPH method was used to assess the antioxidant activity. The phytochemical constituents were determined using LC-MS/MS. The results indicated that R. chalepensis ethanolic extract had 34 compounds, and the predominant compounds were quercetin (9.2 %), myricetin (8.8 %), and camphene (8.0 %). Moreover, the extract had a good level of polyphenols and flavonoids, as demonstrated by inhibiting free radicals (DPPH) (IC50 was 41.2±0.1). Also, the extract exhibited robust antimicrobial activity against P. penneri and S. aureus with an MIC of 12.5 and 25.0 µg/mL, respectively. In conclusion, the results suggest that the R. chalepensis ethanolic extract has good antioxidant and antibacterial properties that could be utilized to develop new antibacterial agents.


Asunto(s)
Antiinfecciosos , Ruta , Antibacterianos/farmacología , Antibacterianos/química , Antiinfecciosos/química , Antiinfecciosos/aislamiento & purificación , Antiinfecciosos/farmacología , Antioxidantes/farmacología , Antioxidantes/química , Cromatografía Liquida , Etanol , Flavonoides/química , Flavonoides/farmacología , Fenoles/farmacología , Fenoles/análisis , Extractos Vegetales/farmacología , Extractos Vegetales/química , Ruta/química , Staphylococcus aureus , Espectrometría de Masas en Tándem , Polifenoles/química , Polifenoles/farmacología , Quercetina/química , Quercetina/aislamiento & purificación , Quercetina/farmacología
15.
Molecules ; 29(4)2024 Feb 10.
Artículo en Inglés | MEDLINE | ID: mdl-38398569

RESUMEN

In this study, Asparagus stipularis was characterized concerning its phytochemical composition, antioxidant potential, cytotoxicity, and pancreatic lipase inhibitory activities. Twenty-seven compounds were identified and quantified by HPLC-DAD-MS in the leaf, stem, pericarp, and rhizome of ethanolic extracts. Seven steroidal saponins were detected, and the highest content was quantified in rhizome and pericap. A. stipularis also contained significant amounts of flavonoids in the aerial part. Isorhamnetin tetra-glycoside, quercetin-3-glucosyl-rutinoside, and rutin were the main flavonoid derivatives in leaf, stem, and pericarp extracts, respectively. In addition, eleven phenolic acids were also detected; among them, caffeic acid, protocatechuic acid, p-hydroxybenzoic acid, and ferulic acid were the predominant phenolics, with these having the highest amounts quantified in the rhizome extracts. All the tested extracts possessed antioxidant capacities, with pericarp and rhizome extracts exhibiting the highest activity in DPPH, ABTS, and FRAP assays. The extracts from pericarp and rhizome were revealed to also be the strongest inhibitors of pancreatic lipase. The rhizome extracts exhibited potent cytotoxic activity against HCT-116 and HepG2 with IC50 values of 30 and 54 µg/mL after 48 h of treatment. The present study demonstrated that A. stipularis can be used as a new source of natural antioxidants and potential anticancer and antiobesity compounds.


Asunto(s)
Antioxidantes , Extractos Vegetales , Antioxidantes/farmacología , Antioxidantes/química , Extractos Vegetales/farmacología , Extractos Vegetales/química , Flavonoides/química , Rutina , Fitoquímicos/farmacología , Lipasa
16.
Phytother Res ; 38(4): 1951-1970, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38358770

RESUMEN

The herb Sophora flavescens displays anti-inflammatory activity and can provide a source of antipsoriatic medications. We aimed to evaluate whether S. flavescens extracts and compounds can relieve psoriasiform inflammation. The ability of flavonoids (maackiain, sophoraflavanone G, leachianone A) and alkaloids (matrine, oxymatrine) isolated from S. flavescens to inhibit production of cytokine/chemokines was examined in keratinocytes and macrophages. Physicochemical properties and skin absorption were determined by in silico molecular modeling and the in vitro permeation test (IVPT) to establish the structure-permeation relationship (SPR). The ethyl acetate extract exhibited higher inhibition of interleukin (IL)-6, IL-8, and CXCL1 production in tumor necrosis factor-α-stimulated keratinocytes compared to the ethanol and water extracts. The flavonoids demonstrated higher cytokine/chemokine inhibition than alkaloids, with the prenylated flavanones (sophoraflavanone G, leachianone A) led to the highest suppression. Flavonoids exerted anti-inflammatory effects via the extracellular signal-regulated kinase, p38, activator protein-1, and nuclear factor-κB signaling pathways. In the IVPT, prenylation of the flavanone skeleton significantly promoted skin absorption from 0.01 to 0.22 nmol/mg (sophoraflavanone G vs. eriodictyol). Further methoxylation of a prenylated flavanone (leachianone A) elevated skin absorption to 2.65 nmol/mg. Topical leachianone A reduced the epidermal thickness in IMQ-treated mice by 47%, and inhibited cutaneous scaling and cytokine/chemokine overexpression at comparable levels to a commercial betamethasone product. Thus, prenylation and methoxylation of S. flavescens flavanones may enable the design of novel antipsoriatic agents.


Asunto(s)
Alcaloides , Flavanonas , Sophora , Ratones , Animales , Flavonoides/química , Sophora flavescens , Sophora/química , Flavanonas/farmacología , Flavanonas/química , Prenilación , Antiinflamatorios/farmacología , Antiinflamatorios/uso terapéutico , Citocinas , Quimiocinas
17.
J Pharm Biomed Anal ; 241: 115983, 2024 Apr 15.
Artículo en Inglés | MEDLINE | ID: mdl-38301575

RESUMEN

Synotis solidaginea Hand.-Mazz. (SSD) is a commonly used Tibetan medicinal herb with a long history of therapeutic use and has good medicinal value and development and utilization prospects. This study aimed to establish and validate a comprehensive strategy integrating UHPLC-Q Exactive Orbitrap HRMS chemical profiling and UHPLC-DAD multi-components quantification for the holistic quality evaluation of SSD. Using UHPLC-Q Exactive Orbitrap HRMS, a total of 58 components in SSD including flavonoids, organic acids, terpenoids, coumarin, and alkaloids were identified or tentatively characterized by authentic reference standards and accurate masses and characteristic fragment ions. The proportion of flavonoids and organic acids were the most in SSD. Subsequently, 7 characteristic components in SSD were quantified by a newly established UHPLC-DAD method that was validated in terms of linearity and ranges, LOD and LOQ, precision, repeatability, stability, and accuracy. Finally, the method was successfully used for the quality evaluation of 8 batches of SSD collected from 5 production areas in China. ANOVA and post hoc Tukey test are used to evaluate the differences in component content in SSD from different production areas. There are significant differences in the content of SSD from different regions (P < 0.05), which may be related to the climate, altitude, and other natural environments of the regions. This work laid a valuable foundation for further development and comprehensive quality control of SSD.


Asunto(s)
Medicamentos Herbarios Chinos , Cromatografía Líquida de Alta Presión/métodos , Medicamentos Herbarios Chinos/química , Medicina Tradicional Tibetana , Control de Calidad , Flavonoides/química
18.
Chem Biodivers ; 21(2): e202301847, 2024 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-38299486

RESUMEN

In this study, I determined the essential oil (EO) chemical composition and crude methanol extract (ME) phytochemical profile of the leaves of Acacia gerrardii (ACGL), a plant growing in Saudi Arabia. Additionally, I assessed their in vitro antioxidant activity. The gas chromatography-mass spectrometry analysis of the EO revealed a high content of oxygenated monoterpenes (79.86 %), primarily dominated by pulegone (35.11 %), carvacrol (27.36 %), and neo-dihydrocarveol (4.67 %). The ME was analyzed by liquid chromatography-mass spectrometry to determine its qualitative chemical profile. Four organic acids, eleven phenolic compounds, sixteen flavonoids, nine terpenoids (eight triterpenoids and one diterpenoid), and one coumarin were found in the ME of ACGL. This extract was found to be dominated by 5,6,4-trihydroxy-7,3-dimethoxyflavone (39.30 %), acteoside (30.27 %), nevadensin (7.55 %), isoacteoside (3.08 %) and apiin (3.23 %), and hesperidin (2.73 %). The phenolic (TPC=127.70±1.47 mg gallic acid equivalents/g of extract) and flavonoid (TFC=85.48±0.12 mg quercetin equivalents/g of extract) contents of the ME were also assessed. The in vitro antioxidant activities of both the EO and ME were evaluated using DPPH, ABTS, and ferrous ion chelating effect assays. Compared to the positive control (vit. E and Vit. C), and both extracts exhibited excellent activity.


Asunto(s)
Acacia , Aceites Volátiles , Antioxidantes/química , Aceites Volátiles/farmacología , Aceites Volátiles/química , Cromatografía de Gases y Espectrometría de Masas , Metanol , Extractos Vegetales/farmacología , Extractos Vegetales/química , Arabia Saudita , Cromatografía Liquida , Cromatografía Líquida con Espectrometría de Masas , Espectrometría de Masas en Tándem , Flavonoides/química
19.
Molecules ; 29(3)2024 Feb 05.
Artículo en Inglés | MEDLINE | ID: mdl-38338480

RESUMEN

To increase the effectiveness of using typical biomass waste as a resource, iridoids, chlorogenic acid, and flavonoids from the waste biomass of Eucommia ulmoides leaves (EULs) were extracted by deep eutectic solvents (DESs) in conjunction with macroporous resin. To optimize the extract conditions, the experiment of response surface was employed with the single-factor of DES composition molar ratio, liquid-solid ratio, water percentage, extraction temperature, and extraction time. The findings demonstrated that the theoretical simulated extraction yield of chlorogenic acid (CGA), geniposidic acid (GPA), aucubin (AU), geniposide (GP), rutin (RU), and isoquercetin (IQU) were 42.8, 137.2, 156.7, 5.4, 13.5, and 12.8 mg/g, respectively, under optimal conditions (hydrogen bond donor-hydrogen bond acceptor molar ratio of 1.96, liquid-solid ratio of 28.89 mL/g, water percentage of 38.44%, temperature of 317.36 K, and time of 55.59 min). Then, 12 resins were evaluated for their adsorption and desorption capabilities for the target components, and the HPD950 resin was found to operate at its optimum. Additionally, the HPD950 resin demonstrated significant sustainability and considerable potential in the recyclability test. Finally, the hypoglycemic in vitro, hypolipidemic in vitro, immunomodulatory, and anti-inflammatory effects of EUL extract were evaluated, and the correlation analysis of six active components with biological activity and physicochemical characteristics of DESs by heatmap were discussed. The findings of this study can offer a theoretical foundation for the extraction of valuable components by DESs from waste biomass, as well as specific utility benefits for the creation and development of natural products.


Asunto(s)
Eucommiaceae , Flavonoides , Flavonoides/química , Solventes/química , Ácido Clorogénico/química , Eucommiaceae/química , Disolventes Eutécticos Profundos , Extractos Vegetales/química , Agua , Iridoides
20.
Chem Biodivers ; 21(3): e202301760, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38217459

RESUMEN

Byrsonima sericea is a species native to Brazil that is widely used in traditional medicine. The seed ethanol extract (SEE) had the highest content of total phenols (179.35 mg GAE g-1 extract) and flavonoids (10.42 mg QE g-1 extract) and was the most active in relation to antioxidant activity (DPPH: IC50 =4.25 µg mL-1 and ABTS: IC50 =4.82 µg mL-1 ). The peel/pulp ethanol extract (PEE) had the best anticholinesterase activity (IC50 =6.02 µg mL-1 ). Chromatographic investigation identified gallic acid, isoquercitrin, quercetin and amentoflavone in SEE, and gallic acid, isoquercitrin, quercetin and rutin in PEE. Six fatty acid methyl esters and seven triterpenes were identified, highlighting oleic acid in the seed hexane extract (61.85 %) and in the peel/pulp hexane extract (52.61 %), and betulin in the peel/pulp hexane extract (5.25 %). The substances and biological activities identified in B. sericea characterize this fruit as a functional food for future studies.


Asunto(s)
Antioxidantes , Quercetina , Antioxidantes/química , Frutas/química , Hexanos , Fenoles/química , Flavonoides/química , Etanol , Ácido Gálico , Extractos Vegetales/química
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