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2.
Planta Med ; 89(11): 1097-1105, 2023 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-37084791

RESUMO

Oral preparations of Casearia sylvestris (guacatonga) are used as antacid, analgesic, anti-inflammatory, and antiulcerogenic medicines. The clerodane diterpenes casearin B and caseargrewiin F are major active compounds in vitro and in vivo. The oral bioavailability and metabolism of casearin B and caseargrewiin F were not previously investigated. We aimed to assess the stability of casearin B and caseargrewiin F in physiological conditions and their metabolism in human liver microsomes. The compounds were identified by UHPLC-QTOF-MS/MS and quantified by validated LC-MS methods. The stability of casearin B and caseargrewiin F in physiological conditions was assessed in vitro. Both diterpenes showed a fast degradation (p < 0.05) in simulated gastric fluid. Their metabolism was not mediated by cytochrome P-450 enzymes, but the depletion was inhibited by the esterase inhibitor NaF. Both diterpenes and their dialdehydes showed a octanol/water partition coefficient in the range of 3.6 to 4.0, suggesting high permeability. Metabolism kinetic data were fitted to the Michaelis-Menten profile with KM values of 61.4 and 66.4 µM and Vmax values of 327 and 648 nmol/min/mg of protein for casearin B and caseargrewiin F, respectively. Metabolism parameters in human liver microsomes were extrapolated to predict human hepatic clearance, and suggest that caseargrewiin F and casearin B have a high hepatic extraction ratio. In conclusion, our data suggest that caseargrewiin F and casearin B present low oral bioavailability due to extensive gastric degradation and high hepatic extraction.


Assuntos
Diterpenos Clerodânicos , Humanos , Diterpenos Clerodânicos/química , Espectrometria de Massas em Tandem , Fígado , Microssomos Hepáticos
3.
Plants (Basel) ; 12(2)2023 Jan 16.
Artigo em Inglês | MEDLINE | ID: mdl-36679128

RESUMO

Fungi of the Candida genus are responsible for invasive candidiasis, which affects people all over the world and has high mortality rates. This is due to their virulence factors, which give them great resistance and pathogenicity. In addition, the emergence of multidrug-resistant strains makes it difficult to treat these infections. In this way, natural products have emerged as an alternative to standard drugs, where plants known for their medicinal properties such as Turnera subulata become attractive to research. The present work aimed to analyze the ethanol extract of Turnera subulata leaves against standard strains of Candida albicans, Candida krusei and Candida tropicalis using broth microdilution techniques. The identification of the compounds in T. subulata leaves by LC-MS revealed the presence of a wide variety of substances such as carboxylic acids and terpenes, with flavonoids and fatty acids being more evident. The antifungal assays showed that the extract was not able to inhibit the growth of the tested strains at concentrations with a clinical relevance. However, at higher concentrations, it was able to inhibit the fungal dimorphism of C. albicans and C. tropicalis. It is possible that the T. subulata extract has potential as an inhibitor of fungal virulence factors without affecting the cell viability. Further research should be carried out in order to assess its inhibitory potential for other fungal virulence factors.

4.
Appl Biochem Biotechnol ; 195(7): 4011-4035, 2023 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-36652091

RESUMO

Endophytic fungi are important sources of anticancer compounds. An endophytic fungus was isolated from the medicinal plant Achyrocline satureioides, and molecularly identified as Biscogniauxia sp. (family Xylariaceae) based on partial nucleotide sequences of the internal transcribed spacer genomic region (GenBank Accession No. ON257911). The chemical characterization and cytotoxic properties of secondary metabolites produced by Biscogniauxia sp. were evaluated in a human melanoma cell line (A375). The fungus was grown in potato-dextrose liquid medium for 25 days, and the extracted compounds were subjected to solid-phase fractionation to obtain the purified FDCM fraction, for which the metabolites were elucidated via ultra-performance chromatography coupled to a mass spectrometer. In the present study, 17 secondary metabolites of Biscogniauxia sp., including nine polyketide derivatives, five terpenoids, and three isocoumarins, were putatively identified. This is the first study to report of the ability of Biscogniauxia sp. in the production of isocoumarin orthosporin; the terpenoids nigriterpene A and 10-xylariterpenoid; the polyketide derivatives daldinin C, 7'dechloro-5'-hydroxygriseofulvin, daldinone D, Sch-642305, curtachalasin A, cytochalasin E, epoxycytochalasins Z8, Z8 isomer, and Z17. Furthermore, this study has reported the biosynthesis of Sch-642305 by a Xylariaceae fungus for the first time. FDCM significantly reduced the viability and proliferation of human melanoma cells at half-maximal inhibitory concentrations ​​of 10.34 and 6.89 µg/mL, respectively, and induced late apoptosis/necrosis and cell cycle arrest in G2/M phase after 72 h of treatment. Given its ability to produce unique metabolites with promising cytotoxic effects, Biscogniauxia sp. of A. satureioides may be a reservoir of compounds with important therapeutic applications.


Assuntos
Achyrocline , Antineoplásicos , Melanoma , Humanos , Achyrocline/química , Extratos Vegetais/química , Antineoplásicos/farmacologia , Linhagem Celular , Melanoma/tratamento farmacológico , Fungos
5.
J Biomol Struct Dyn ; 41(19): 9282-9296, 2023 11.
Artigo em Inglês | MEDLINE | ID: mdl-36326114

RESUMO

Lantana camara L. (Verbenaceae), commonly called lead cambará, has often been used in folk medicine as antiseptic, antispasmodic, against hemorrhages, flu, colds, and diarrheic. This plant is considered a weed and an ornamental and medicinal plant and is an essential source of natural organic compounds, mainly flavonoids. This work aims to investigate the chemical composition and evaluate the biological properties such as antioxidant and acetylcholinesterase of the constituents from L. camara flowers. In addition, the computational simulation was carried out with the constituents identified. The results showed that methanolic extract of the flowers of L. camara presents toxicity, antioxidant activity with 97.8% inhibition percentage in the concentration of 0.25 mg mL-1 against the DPPH radical, and acetylcholinesterase activity. The phytochemical study of extract from L. camara flowers resulted in LC-MS identification of 18 polyphenolic compounds, such as phenolic acid derivatives, phenylethanoid glycosides, and flavonoids. In the in silico study, flavonoid isoverbascoside showed affinity energy of -9.9 kcal.mol-1 with the AChE enzyme. Their phytochemical content, mainly the presence of flavonoids and phenolic compounds in L. camara extracts, may be related to the antioxidant and anticholinesterase potential observed.


Assuntos
Antioxidantes , Lantana , Antioxidantes/farmacologia , Acetilcolinesterase , Lantana/química , Simulação de Acoplamento Molecular , Extratos Vegetais/farmacologia , Flores , Compostos Fitoquímicos/farmacologia , Flavonoides/farmacologia
6.
Braz. J. Pharm. Sci. (Online) ; 59: e21224, 2023. tab, graf
Artigo em Inglês | LILACS | ID: biblio-1429973

RESUMO

Abstract In this research, aqueous and ethanolic extracts from Justicia pectoralis Jacq and Croton Jacobinensis Baill were characterized. The UPLC-QTOF-MSE analysis was performed on the extracts identified, predominantly, flavonoids, tannins and acids. The extracts did not indicate toxicity in human epithelial cells. C. jacobinensis presented a concentration of phenolics 60.5% higher than J. pectoralis in all scenarios evaluated and, for both samples, the hydroalcoholic extract at 70% exhibited the best efficiency in the extraction (14501.3 and 32521.5 mg GAE 100 g-1 for J. pectoralis and C. jacobinensis, respectively). The antioxidant activity presented a positive correlation with the concentration of phenolics, being 1.186,1 and 1.507,9 µM of Trolox for J. pectoralis and C. jacobinensis at 70% of ethanol; however, it was not verified statistical difference between the ethanolic solutions (p < 0.05). The antimicrobial activity of J. pectoralis extracts was highlighted once was the most effective against gram-positive bacteria. The results suggest that both J. pectoralis and C. jacobinensis extracts present the potential to be applied as natural additives due to their antioxidant and antimicrobial activity and safety. Thus, it is suggesting the development of studies that could investigate the interaction of these plant extracts with food matrices is required


Assuntos
Extratos Vegetais/análise , Euphorbiaceae/classificação , Justiça Social/classificação , Croton/classificação , Toxicidade , Antioxidantes/análise , Flavonoides/análise , Compostos Fitoquímicos/efeitos adversos , Bactérias Gram-Positivas/metabolismo
7.
Ciênc. rural (Online) ; 53(9): e20220342, 2023. tab, graf, ilus
Artigo em Inglês | VETINDEX | ID: biblio-1418782

RESUMO

This study evaluated the changes caused by cooking presoaked aged carioca beans in the autoclave steam, focusing on its bioactive components, antioxidant activity, and nutritional compounds. Additionally, to identify which carioca bean cultivar could preserve the most quantity of bioactive compounds in cooked flour. The cooked flours from Imperador had the highest antioxidant activity (DDPH: 10.58 µmolTrolox·g-1, ABTS: 18.71 µmolTrolox·g-1), anthocyanins (8.08 µg·g-1), and total phenolic content (TPC) (36.69 mg·g-1). The cultivar Gol also retained part of these compounds after cooking. The phenolic and saponin profiles of cooked flours revealed a reduction in phenolic compounds such as catechin, epicatechin, and kaempferol and an increase in soyasaponin-Ba and Bb. The samples Notavel, Dama, and Madreperola, presented the highest amount of soyasaponin-A0. Thus, the cooked flours from Imperador and Gol stood out due to their retention of part of their bioactive compounds, such as polyphenols and group B saponins.


Este estudo avalia as alterações causadas pelo cozimento do feijão carioca, envelhecido e pré-embebido, no vapor da autoclave, com foco em seus componentes bioativos, atividade antioxidante e compostos nutricionais. Além disso, identifica qual cultivar de feijão carioca preserva a maior quantidade de compostos bioativos na farinha de feijão cozida. As farinhas cozidas do Imperador apresentaram a maior atividade antioxidante (DDPH: 10.58 µmolTrolox·g-1, ABTS: 18.71 µmolTrolox·g-1), antocianinas (8.08 µg·g-1) e fenólicos totais (TPC) (36.69 mg·g-1). A cultivar Gol também reteve parte desses compostos após o cozimento. Os perfis fenólicos e saponínicos das farinhas cozidas revelaram redução de compostos fenólicos, como a catequina, epi-catequina e kaempferol e aumento de soyasaponin-Ba e Bb. As amostras Notável, Dama e Madrepérola, apresentaram a maior quantidade de sojasaponina-A0. Assim, as farinhas cozidas do Imperador e Gol se destacaram pela retenção de parte de seus compostos bioativos, como polifenóis e saponinas do grupo B.


Assuntos
Saponinas , Taninos , Polifenóis , Fabaceae/química , Antioxidantes
8.
Food Chem (Oxf) ; 5: 100149, 2022 Dec 30.
Artigo em Inglês | MEDLINE | ID: mdl-36573106

RESUMO

The aim of this study was to produce powders from the phenolic extract of the cashew by-product using maltodextrin and gum arabic as encapsulating agents to preserve these bioactive compounds and their antioxidative activity. Extraction was assisted by an ultrasound bath to increase the release of the bioactive compounds, resulting in the hydroalcoholic extract from cashew bagasse. The powders were physically and morphologically characterized, and their total phenolics, antioxidant activity and bioaccessibility were evaluated. All parameters were analyzed by chemometrics. In addition, UPLC-HRMS analysis was used to evaluate the phenolic profile of the extracts, revealing that the powders were able to protect some of the original compounds of the extract, such as catechin, the myricetin fraction and quercetin. The powders showed high total phenolic retention capacity, especially maltodextrin (2893.34 ± 20.18 mg GAE/100 g (DW)), which was the encapsulant that preserved the highest content of polyphenols and antioxidant activity after bioaccessibility in comparison to the unencapsulated extract. The powders showed low water activity (<0.2), low moisture (<8%), high solubility (>60 %) and low hygroscopicity (<4%). The SEM analysis showed that lyophilized extract samples resembled broken glass, which is characteristic of the lyophilization process, and in addition to a predominantly amorphous structure as demonstrated by the X-ray diffraction. The extraction and encapsulation of phenolic compounds from the cashew by-product through lyophilization and using maltodextrin and gum arabic as encapsulants enabled their preservation and potential use of these compounds by the nutraceutical or food industry, and can be used as food additive in order to enrich the content of compounds and the antioxidant activity of numerous products.

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.
Pharmaceutics ; 14(4)2022 Mar 24.
Artigo em Inglês | MEDLINE | ID: mdl-35456532

RESUMO

(1) Background: Candida is a genus of yeasts with notable pathogenicity and significant ability to develop antimicrobial resistance. Gossypium hirsutum L., a medicinal plant that is traditionally used due to its antimicrobial properties, has demonstrated significant antifungal activity. Therefore, this study investigated the chemical composition and anti-Candida effects of aqueous (AELG) and hydroethanolic (HELG) extracts obtained from the leaves of this plant. (2) Methods: The extracts were chemically characterized by UPLC-QTOF-MS/MS, and their anti-Candida activities were investigated by analyzing cell viability, biofilm production, morphological transition, and enhancement of antifungal resistance. (3) Results: The UPLC-QTOF-MS/MS analysis revealed the presence of twenty-one compounds in both AELG and HELG, highlighting the predominance of flavonoids. The combination of the extracts with fluconazole significantly reduced its IC50 values against Candida albicans INCQS 40006, Candida tropicalis INCQS 40042, and C. tropicalis URM 4262 strains, indicating enhanced antifungal activity. About biofilm production, significant inhibition was observed only for the AELG-treated C. tropicalis URM 4262 strain in comparison with the untreated control. Accordingly, this extract showed more significant inhibitory effects on the morphological transition of the INCQS 40006 and URM 4387 strains of C. albicans (4) Conclusions: Gossypium hirsutum L. presents promising antifungal effects, that may be potentially linked to the combined activity of chemical constituents identified in its extracts.

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