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1.
Molecules ; 29(10)2024 May 11.
Artigo em Inglês | MEDLINE | ID: mdl-38792127

RESUMO

Red rice has been proposed as a super-food. Accordingly, the nutritional properties (AOAC), as well as its chemical composition, including sugars (HPLC-RI), organic acids (UFLC-PDA), tocopherols (HPLD-FD), and phenolic compounds (LC-DAD-ESI/MSn), together with the main bioactive properties (antioxidant, cytotoxic, antiproliferative, and antibacterial activities), were evaluated to access its nutritional benefits and health improvement potential. The most abundant macronutrients found were carbohydrates (87.2 g/100 g dw), proceeded by proteins (9.1 g/100 g dw), fat (2.6 g/100 g dw), and ash (1.1 g/100 g dw). Sucrose and raffinose were the only detected sugars, with sucrose presenting the maximum concentration (0.74 g/100 g dw). MUFAs and PUFAs were the predominant fatty acids (40.7% and 31%, respectively). Among the two detected tocopherol isoforms, γ-tocopherol (0.67 mg/100 g dw) predominated over α-tocopherol. The phenolic compounds profile, majorly composed of flavan-3-ols, should be associated with the detected bioactivities, which may provide biological benefits to human health beyond the primary nutritional effect. Overall, the bioactive potential of red rice was comprehensively accessed.


Assuntos
Antioxidantes , Oryza , Oryza/química , Antioxidantes/química , Antioxidantes/farmacologia , Antioxidantes/análise , Humanos , Tocoferóis/análise , Tocoferóis/química , Fenóis/análise , Fenóis/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/análise , Antibacterianos/química , Antibacterianos/farmacologia , Antibacterianos/análise
2.
Molecules ; 29(12)2024 Jun 13.
Artigo em Inglês | MEDLINE | ID: mdl-38930892

RESUMO

The Lamiaceae family, which includes several well-known aromatic plants, is scientifically relevant due to its essential oils (EOs). In this work, four EOs from Mediterranean species, namely Origanum vulgare L., Rosmarinus officinalis L., Salvia officinalis L., and Thymus vulgaris L., were evaluated for their volatile profiles and the biological activity in vitro to assess their potential use in the food and cosmetic sector. GC/MS analysis revealed dominant compounds, such as carvacrol, thymol, and eucalyptol. Regarding biological action, the samples exhibited antioxidant, cytotoxic, anti-inflammatory, antimicrobial, and antifungal activities, with O. vulgare and T. officinalis standing out. T. vulgaris showed the lowest EC50 in the reducing power assay, and O. vulgare had the lowest EC50 in the DPPH assay. Most EOs also displayed excellent anti-inflammatory responses and antifungal properties, with O. vulgare and T. vulgaris also demonstrating antibacterial activity. All EOs from Mediterranean species showed cytotoxicity against tumoral cell lines. Overall, the selected EOs stood out for their interesting bioactivities, with the obtained results underscoring their potential as natural preservatives and bioactive agents in various industrial applications, including food, pharmaceuticals, and cosmetics.


Assuntos
Antioxidantes , Lamiaceae , Óleos Voláteis , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Lamiaceae/química , Antioxidantes/farmacologia , Antioxidantes/química , Humanos , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Cromatografia Gasosa-Espectrometria de Massas , Origanum/química , Salvia officinalis/química , Linhagem Celular Tumoral , Thymus (Planta)/química , Anti-Infecciosos/farmacologia , Anti-Infecciosos/química , Plantas Comestíveis/química , Óleos de Plantas/química , Óleos de Plantas/farmacologia , Timol/farmacologia , Timol/química , Testes de Sensibilidade Microbiana , Cimenos
3.
Molecules ; 29(15)2024 Jul 25.
Artigo em Inglês | MEDLINE | ID: mdl-39124890

RESUMO

Coriander, caraway, and mystical cumin are famous for their aromatic properties and widely used in Moroccan cuisine. The nutritional/phytochemical composition of their seeds (used for food flavoring and preservation) were compared. Their antioxidant, anti-inflammatory, cytotoxic and hepatotoxic effects were also explored. The fat content was similar among the samples (13%), with monounsaturated fatty acids being predominant. The coriander and mystical cumin seeds were extremely rich in C18:1n9c (81 and 85%, respectively) while, in the caraway, C18:1n12 (25%) was found together with C18:1n9c (32%). The caraway seeds also presented a higher proportion of C18:2n6c (34%) than the other seeds (13 and 8%, correspondingly). γ-Tocotrienol was the major vitamin E form in all the samples. The caraway seeds contained double the amount of protein (~18%) compared to the other seeds (~8%) but, qualitatively, the amino acid profiles among all seeds were similar. The seeds were also rich in dietary fiber (40-53%); however, differences were found in their fiber profiles. Caraway showed the highest antioxidant profile and anti-inflammatory activity and an LC-DAD-ESI/MSn analysis revealed great differences in the phenolic profiles of the samples. Cytotoxicity (NCI-H460, AGS, MCF-7, and CaCo2) and hepatotoxicity (RAW 264.7) were not observed. In sum, besides their flavoring/preservation properties, these seeds are also relevant source of bioactive compounds with health-promoting activities.


Assuntos
Anti-Inflamatórios , Antioxidantes , Coriandrum , Compostos Fitoquímicos , Especiarias , Antioxidantes/química , Antioxidantes/farmacologia , Humanos , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Coriandrum/química , Especiarias/análise , Marrocos , Cuminum/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Sementes/química
4.
Molecules ; 28(22)2023 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-38005324

RESUMO

Nowadays, bee products are commended by consumers for their medicinal and dietary properties. This study aimed to differentiate between monofloral bee pollens originating from Portugal using phenolic and volatile profiles and investigate their antioxidant and cytotoxic activity. Total phenolic and flavonoid compounds were recorded between 2.9-35.8 mg GAE/g and 0.7-4.8 mg QE/g, respectively. The LC/DAD/ESI-MSn analytical results allowed us to identify and quantify a total of 72 compounds, including phenolic and phenylamide compounds, whereas GC-MS results revealed the presence of 49 different compounds, mostly ketones, aldehydes, esters, hydrocarbons, and terpenes. The highest DPPH• radical scavenging activity, EC50: 0.07 mg/mL, was recorded in the sample dominated by Castanae sp. pollen, whereas the Rubus sp. (1.59 mM Trolox/mg) and Cistaceae sp. (0.09 mg GAE/g) pollen species exhibited the highest antioxidant activity in ABTS•+ and reducing power assays, respectively. Regarding the anti-carcinogenic activity, only Carduus sp. showed remarkable cytotoxic potential against MCF-7.


Assuntos
Antioxidantes , Fenóis , Abelhas , Animais , Portugal , Fenóis/análise , Antioxidantes/farmacologia , Flavonoides , Pólen/química
5.
Molecules ; 28(11)2023 May 30.
Artigo em Inglês | MEDLINE | ID: mdl-37298924

RESUMO

Essential oils (EOs) obtained from Juniperus communis L. are frequently used in the production of bioproducts. However, there are no studies regarding industrial crops' production, allowing for better control of the quality and production of juniper EOs. To select the plant material for developing future crops of this species in northern Spain, four locations where this shrub species grows in the wild were selected and samples of both genera were collected. The EOs were obtained by steam distillation, and their chemical composition and bioactivity were evaluated. The results showed that the yield of EOs from male and female samples were within the usual reported ranges, varying between 0.24 and 0.58% (dry basis, d.b.). However, limonene content in three locations varied between 15 and 25%, which is between 100% and 200% higher than the values usually reported for other European countries. The antibacterial activity was determined by broth microdilution and showed that gram-positive bacteria were more susceptible to the tested EOs since, in general, lower MIC values were obtained compared to gram-negatives. The EOs from location 1 (L1F) and 2 (L2M) inhibited the growth of six out of the eight clinical strains tested. Samples from location 1 were particularly effective, exhibiting MBC against two gram-negative (E. coli and P. mirabilis) and one gram-positive bacteria (E. faecalis). Moreover, the majority of the EOs tested showed anti-inflammatory activity. Cytotoxic effect has been demonstrated in tumor cell lines, with the best results observed against gastric carcinoma (AGS) cells (GI50 between 7 to 77 µg/mL). Although generally presenting higher GI50, most samples also inhibited the growth of non-tumoral cells, particularly hepatocytes (PLP2 cells). Therefore, its use for their anti-proliferative activity should consider specific conditions to avoid damaging normal cells. Finally, the results and conclusions obtained led to the selection of the female shrubs from location 1 (L1F) as the plant material to be propagated in order to produce plants for a future juniper crop.


Assuntos
Juniperus , Óleos Voláteis , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Juniperus/química , Escherichia coli , Antibacterianos/farmacologia , Antibacterianos/química , Bactérias Gram-Positivas
6.
Molecules ; 28(11)2023 Jun 02.
Artigo em Inglês | MEDLINE | ID: mdl-37299006

RESUMO

Aromatic plants are a remarkable source of natural products. Aloysia citrodora Paláu (Verbenaceae), commonly known as lemon verbena, is a relevant source of essential oils with potential applications due to its lemony scent and bioactive properties. Studies carried out on this species have focused on the volatile composition of the essential oil obtained by Clevenger hydrodistillation (CHD), with little information available on alternative extraction methodologies or the biological properties of the oil. Therefore, this work aimed to compare the volatile composition, antioxidant activity, cytotoxicity, anti-inflammatory and antibacterial activities of the essential oil extracted by conventional hydrodistillation by Clevenger (CHD) and Microwave-Assisted Hydrodistillation (MAHD). Significant differences (p < 0.05) were observed for some compounds, including the two major ones, geranial (18.7-21.1%) and neral (15.3-16.2%). Better antioxidant activity was exhibited by the MAHD essential oil in DPPH radical scavenging and reducing power assays, while no differences were observed in the cellular antioxidant assay. The MADH essential oil also presented higher inhibition against four tumoral cell lines and exhibited lower cytotoxicity in non-tumoral cells as compared with Clevenger-extracted essential oil. In contrast, the latter showed higher anti-inflammatory activity. Both essential oils were able to inhibit the growth of eleven out of the fifteen bacterial strains tested.


Assuntos
Óleos Voláteis , Verbenaceae , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Antioxidantes/farmacologia , Micro-Ondas , Palau , Verbenaceae/química , Anti-Inflamatórios/farmacologia
7.
Molecules ; 28(21)2023 Oct 31.
Artigo em Inglês | MEDLINE | ID: mdl-37959787

RESUMO

BACKGROUND: Grape agri-food wastes, such as skin, seeds, and other discarded by-products, contain phytochemical compounds that offer potential health benefits. METHODS: This study aimed to investigate the polyphenol composition and bioactivities of different extracts obtained from grape marc and seeds, with the goal of exploring their potential for application as natural food additives. RESULTS: Regardless of the extraction method used (dynamic maceration, ultrasound-assisted extraction (UAE), and microwave-assisted extraction (MAE)), all extracts exhibited relatively high concentrations of phenolic compounds. The chemical characterization of the extracts revealed the presence of specific compounds and chemical groups associated with each extraction methodology. Moreover, the extracts displayed satisfactory antioxidant activities, especially in inhibiting lipoperoxidation as assessed by the TBARS assay. Additionally, the extracts demonstrated effective inhibition against different strains of bacteria and fungi known as food contaminants. Taken together, these findings indicate that those extracts have the potential to be tested as natural antioxidants and preservatives with sustainable origins in food and beverage systems. Among the extraction methods evaluated, traditional maceration and UAE provided extracts with the highest antioxidant and antimicrobial activities. CONCLUSIONS: Our results suggest the opportunity to explore grape marc and seeds discarded by the winery industry in Portugal as natural sources of bioactive compounds, which could be employed as functional food ingredients or technological additives. The valorization of grape biowastes offers a promising strategy to reduce waste and harness their potential health benefits.


Assuntos
Eliminação de Resíduos , Vitis , Polifenóis/química , Vitis/química , Antioxidantes/química , Cromatografia Líquida de Alta Pressão , Espectrometria de Massas em Tandem , Extratos Vegetais/química , Sementes/química
8.
Molecules ; 28(2)2023 Jan 13.
Artigo em Inglês | MEDLINE | ID: mdl-36677892

RESUMO

Bee pollen is frequently characterized as a natural source of bioactive components, such as phenolic compounds, which are responsible for its pharmaceutical potential and nutritional properties. In this study, we evaluated the bioactive compound contents of mono- and polyfloral bee pollen samples using spectroscopic and chromatographic methods and established links with their antioxidant and antitumor activity. The findings demonstrated that the botanical origin of bee pollen has a remarkable impact on its phenolic (3-17 mg GAE/g) and flavonoid (0.5-3.2 mg QE/g) contents. Liquid chromatography-mass spectrometry analysis revealed the presence of 35 phenolic and 13 phenylamide compounds in bee pollen, while gas chromatography-mass spectrometry showed its richness in volatiles, such as hydrocarbons, fatty acids, alcohols, ketones, etc. The concentration of bioactive compounds in each sample resulted in a substantial distinction in their antioxidant activity, DPPH (EC50: 0.3-0.7 mg/mL), ABTS (0.8-1.3 mM Trolox/mg), and reducing power (0.03-0.05 mg GAE/g), with the most bioactive pollens being the monofloral samples from Olea europaea and Ononis spinosa. Complementarily, some samples revealed a moderate effect on cervical carcinoma (GI50: 495 µg/mL) and breast adenocarcinoma (GI50: 734 µg/mL) cell lines. This may be associated with compounds such as quercetin-O-diglucoside and kaempferol-3-O-rhamnoside, which are present in pollens from Olea europaea and Coriandrum, respectively. Overall, the results highlighted the potentiality of bee pollen to serve health-promoting formulations in the future.


Assuntos
Antioxidantes , Flavonoides , Animais , Abelhas , Antioxidantes/química , Flavonoides/química , Cromatografia Gasosa-Espectrometria de Massas , Espectrometria de Massas , Fenóis/química , Pólen/química
9.
Molecules ; 28(20)2023 Oct 17.
Artigo em Inglês | MEDLINE | ID: mdl-37894606

RESUMO

The demand for organic and functional food continues to increase yearly. Among the available functional foods, propolis is a bee product that has various beneficial properties, including antimicrobial, antioxidant, and anti-inflammatory activities. However, it generally is only available in ethanol solution, which has poor bioavailability, as it is relatively insoluble in water. The use of such ethanol extracts is often objectionable because of the alcohol content and because they have a strong and striking taste. Development of alternatives that can efficiently and safely increase solubility in water, and that meet organic production specifications, has been a challenge. To address these concerns, microcapsules were developed using spray-dryer technology from an emulsion based on EPP-AF® propolis and gum arabic (i-CAPS). These propolis-loaded microcapsules were characterized using FT-IR, SEM, TGA, HPLC, and spectrophotometric techniques, along with determination of antimicrobial, antioxidant, antitumor, anti-inflammatory, and antihypercholesterolemic activities, as well as permeability in in vitro models. The production system resulted in microcapsules with a spherical shape and an encapsulation efficiency of 93.7 ± 0.7%. They had IC50s of 2.654 ± 0.062 and 7.342 ± 0.058 µg/mL by FRAP and DPPH antioxidant methods, respectively. The EPP-AF® i-CAPS also had superior antimicrobial activity against Gram-positive bacteria. Antitumor activity was calculated based on the concentration that inhibited 50% of growth of AGS, Caco-2, and MCF-7 cell strains, giving results of 154.0 ± 1.0, 117 ± 1.0, and 271.0 ± 25 µg/mL, respectively. The microcapsule presentation reduced the permeation of cholesterol by 53.7%, demonstrating antihypercholesterolemic activity, and it improved the permeability of p-coumaric acid and artepillin C. The IC50 for NO production in RAW 264.7 cells was 59.0 ± 0.1 µg/mL. These findings demonstrate the potential of this new propolis product as a food and pharmaceutical ingredient, though additional studies are recommended to validate the safety of proposed dosages.


Assuntos
Anti-Infecciosos , Própole , Humanos , Própole/farmacologia , Antioxidantes/farmacologia , Antioxidantes/análise , Cápsulas , Espectroscopia de Infravermelho com Transformada de Fourier , Células CACO-2 , Anti-Infecciosos/farmacologia , Etanol , Água , Anti-Inflamatórios/farmacologia
10.
Molecules ; 28(7)2023 Apr 02.
Artigo em Inglês | MEDLINE | ID: mdl-37049931

RESUMO

The peels from three pumpkin genotypes cultivated in Greece were assessed for their phenolic content and bioactive properties to obtain extracts with a high preservative capacity. The optimization of the extraction was performed through response surface methodology (RSM) based on a Box-Behnken experimental design after applying two extraction techniques: heat-assisted (HAE) and ultrasound-assisted (UAE) extraction. The implemented independent variables were time, solvent concentration, and temperature/power (for HAE/UAE), while as dependent variables the dry residue (DR), reducing power (RP), and total phenolic content (TP) were considered. In general, HAE was the most effective technique for 'TL' (75 min; 30 °C; 24% ethanol) and 'Voutirato' (15 min; 30 °C; 10% ethanol), while UAE was more effective for 'Leuka Melitis' (5 min; 400 W; 0% ethanol). The extracts obtained in the global optimum conditions for each genotype peel were then assessed for their phenolic profile, by HPLC-DAD-ESI/MS, and bioactive potential. Seven phenolic compounds were detected, including four flavonoids, two phenolic acids, and one flavan-3-ol. The extracts presented high antioxidant, antibacterial, and antifungal potential, with no cytotoxicity for non-tumor cells. The optimized conditions for the extraction of preservative compounds from bioresidues were defined, allowing the acquisition of antioxidant and antimicrobial extracts and proving their potential for food application.


Assuntos
Antioxidantes , Cucurbita , Antioxidantes/farmacologia , Temperatura Alta , Fenóis/química , Etanol/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química
11.
Molecules ; 28(10)2023 May 10.
Artigo em Inglês | MEDLINE | ID: mdl-37241749

RESUMO

Juniperus communis L. is a species commonly grown in regions of the Northern Hemisphere, and is a good candidate to be cultivated in marginal lands. Plants coming from a pruning performed in a natural population located in Spain were used to assess the yield and quality of different products obtained following the cascade principle. A total of 1050 kg of foliage biomass were crushed, steam-distilled, and separated into fractions to produce biochar and absorbents for the pet industry using pilot plants. The obtained products were analysed. The essential oil, with a yield of 0.45% dry basis and a qualitative chemical composition similar to that described for the berries in international standards or monographs, showed antioxidant activity with promising CAA results (inhibition of 89% of the cell's oxidation). However, regarding antibacterial and antifungal activities, it only inhibited the growth of microorganisms at the maximum concentration tested, 2.5%. Concerning the hydrolate, it did not show bioactivity. Regarding the biochar, whose yield was 28.79% dry basis, interesting results were obtained for its characterisation as a possible soil improver for agronomic purposes (PFC 3(A)). Finally, promising results were obtained regarding the use of common juniper as absorbent, taking into account the physical characterisation and odour control capacity.


Assuntos
Juniperus , Óleos Voláteis , Juniperus/química , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Antioxidantes/farmacologia , Antifúngicos/farmacologia
12.
Molecules ; 27(19)2022 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-36235035

RESUMO

Several scientific studies have been proving the bioactive effects of many aromatic and medicinal plants associated with the presence of a high number of bioactive compounds, namely phenolic compounds. The antioxidant, anti-inflammatory, and antimicrobial capacities of these molecules have aroused high interest in some industrial sectors, including food, pharmaceuticals, and cosmetics. This work aimed to determine the phenolic profiles of the infusions and hydroethanolic extracts of five plants (Carpobrotus edulis, Genista tridentata, Verbascum sinuatum, Cytisus multiflorus, and Calluna vulgaris) that have been employed in many traditional preparations. In addition, the antioxidant, antimicrobial, anti-inflammatory, and anti-tumoral activity of each different preparation was evaluated using in vitro assays. The HPLC-DAD-ESI/MS profile revealed the presence of eighty phenolic compounds, belonging to seven different families of compounds. Regarding antioxidant properties, the hydroethanolic extract of C. edulis showed a potent effect in the TBARS assay (IC50 = 1.20 µg/mL), while G. tridentata hydroethanolic extract achieved better results in the OxHLIA test (IC50 = 76 µg/mL). For cytotoxic and anti-inflammatory results, V. sinuatum infusions stood out significantly, with GI50 = 59.1-92.1 µg/mL and IC50 = 121.1 µg/mL, respectively. Finally, C. edulis hydroethanolic extract displayed the most relevant antibacterial activity, showing MBC values of 0.25-1 mg/mL, while G. tridentata hydroethanolic extract exerted the greatest antifungal effects (MFC of 0.5-1 mg/mL). The results of this study deepen the knowledge of the phenolic profiles and also provide evidence on the bioactive properties of the species selected, which could be considered highly valuable options for research and application in several sectors, namely food, cosmetics, and pharmaceuticals.


Assuntos
Antioxidantes , Extratos Vegetais , Antibacterianos/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Antifúngicos , Antioxidantes/química , Antioxidantes/farmacologia , Fenóis/química , Fenóis/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Substâncias Reativas com Ácido Tiobarbitúrico
13.
Molecules ; 27(23)2022 Nov 30.
Artigo em Inglês | MEDLINE | ID: mdl-36500462

RESUMO

Pumpkin fruits are widely appreciated and consumed worldwide. In addition to their balanced nutritional profile, pumpkin species also present valuable bioactive compounds that confer biological and pharmacological properties to them. However, the seeds, peels, and fibrous strands resulting from pumpkin processing are still poorly explored by the food industry. The current study used those fruit components from the genotypes of pumpkin that are economically significant in Portugal and Algeria to produce bioactive extracts. In order to support their usage as preservatives, their phenolic content (HPLC-DAD-ESI/MS) and antioxidant (OxHLIA and TBARS) and antimicrobial properties (against eight bacterial and two fungal strains) were assessed. In terms of phenolic profile, the peel of the Portuguese 'Common Pumpkin' showed the most diversified profile and also the highest concentration of total phenolic compounds, with considerable concentrations of (-)-epicatechin. Regarding the antioxidant capacity, the seeds of 'Butternut Squash' from both countries stood out, while the fibrous strands of Portuguese 'Butternut Squash' and the seeds of Algerian 'Gold Nugget Pumpkin' revealed the strongest antimicrobial activity. The bioactive compounds identified in the pumpkin byproducts may validate their enormous potential as a source of bio-based preservatives that may enhance consumers' health and promote a circular economy.


Assuntos
Anti-Infecciosos , Cucurbita , Antioxidantes/farmacologia , Extratos Vegetais/farmacologia , Fenóis/farmacologia , Anti-Infecciosos/farmacologia
14.
Int J Mol Sci ; 22(2)2021 Jan 06.
Artigo em Inglês | MEDLINE | ID: mdl-33418931

RESUMO

Candidaalbicans represents one of the most common fungal pathogens. Due to its increasing incidence and the poor efficacy of available antifungals, finding novel antifungal molecules is of great importance. Camphor and eucalyptol are bioactive terpenoid plant constituents and their antifungal properties have been explored previously. In this study, we examined their ability to inhibit the growth of different Candida species in suspension and biofilm, to block hyphal transition along with their impact on genes encoding for efflux pumps (CDR1 and CDR2), ergosterol biosynthesis (ERG11), and cytotoxicity to primary liver cells. Camphor showed excellent antifungal activity with a minimal inhibitory concentration of 0.125-0.35 mg/mL while eucalyptol was active in the range of 2-23 mg/mL. The results showed camphor's potential to reduce fungal virulence traits, that is, biofilm establishment and hyphae formation. On the other hand, camphor and eucalyptol treatments upregulated CDR1;CDR2 was positively regulated after eucalyptol application while camphor downregulated it. Neither had an impact on ERG11 expression. The beneficial antifungal activities of camphor were achieved with an amount that was non-toxic to porcine liver cells, making it a promising antifungal compound for future development. The antifungal concentration of eucalyptol caused cytotoxic effects and increased expression of efflux pump genes, which suggests that it is an unsuitable antifungal candidate.


Assuntos
Antifúngicos/farmacologia , Cânfora/farmacologia , Candida albicans/patogenicidade , Eucaliptol/farmacologia , Virulência/efeitos dos fármacos , Animais , Biofilmes/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Candida albicans/fisiologia , Sobrevivência Celular/efeitos dos fármacos , Células Cultivadas , Proteínas Fúngicas/metabolismo , Fígado/citologia , Fígado/efeitos dos fármacos , Fígado/metabolismo , Proteínas de Membrana Transportadoras/metabolismo , Testes de Sensibilidade Microbiana , Espécies Reativas de Oxigênio/metabolismo , Suínos
15.
Molecules ; 26(16)2021 Aug 10.
Artigo em Inglês | MEDLINE | ID: mdl-34443411

RESUMO

Several novel methyl 7-[(hetero)arylamino]thieno[2,3-b]pyrazine-6-carboxylates were synthesized by Pd-catalyzed C-N Buchwald-Hartwig cross-coupling of either methyl 7-aminothieno[3,2-b]pyrazine-6-carboxylate with (hetero)arylhalides or 7-bromothieno[2,3-b]pyrazine-6-carboxylate with (hetero)arylamines in good-to-excellent yields (50% quantitative yield), using different reaction conditions, namely ligands and solvents, due to the different electronic character of the substrates. The antitumoral potential of these compounds was evaluated in four human tumor cell lines: gastric adenocarcinoma (AGS), colorectal adenocarcinoma (CaCo-2), breast carcinoma (MCF7), and non-small-cell lung carcinoma (NCI-H460) using the SRB assay, and it was possible to establish some structure-activity relationships. Furthermore, they did not show relevant toxicity against a non-tumor cell line culture from the African green monkey kidney (Vero). The most promising compounds (GI50 ≤ 11 µM), showed some selectivity either against AGS or CaCo-2 cell lines without toxicity at their GI50 values. The effects of the methoxylated compounds 2b (2-OMeC6H4), 2f and 2g (3,4- or 3,5-diOMeC6H3, respectively) on the cell cycle profile and induction of apoptosis were further studied in the AGS cell line. Nevertheless, even for the most active (GI50 = 7.8 µM) and selective compound (2g) against this cell line, it was observed that a huge number of dead cells gave rise to an atypical distribution on the cell cycle profile and that these cells were not apoptotic, which points to a different mechanism of action for the AGS cell growth inhibition.


Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Apoptose , Pontos de Checagem do Ciclo Celular , Pirazinas/síntese química , Pirazinas/farmacologia , Antineoplásicos/química , Apoptose/efeitos dos fármacos , Ciclo Celular/efeitos dos fármacos , Pontos de Checagem do Ciclo Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Humanos , Pirazinas/química
16.
Molecules ; 26(7)2021 Mar 26.
Artigo em Inglês | MEDLINE | ID: mdl-33810432

RESUMO

Ruscus aculeatus L. is a subshrub used in traditional medicine in different parts of the world, namely in Europe and the Iberian Peninsula. According to reported folk knowledge, the aerial parts are mainly used as diuretics and the underground organs are used for the treatment of disorders of the urinary system and as a laxative. In this work, the aerial part and the roots and rhizomes of R. aculeatus were chemically characterized with regard to the content of phenolic compounds and bioactive properties. Aqueous (infusions and decoctions) preparations and hydroethanolic extracts from the two mentioned parts of the plant were prepared. Nine phenolic compounds were detected in all the extracts. Apigenin-C-hexoside-C-pentoside isomer II was the major compound in aqueous extracts and, in the hydroethanolic extract was quercetin-O-deoxyhexoside-hexoside followed by apigenin-C-hexoside-C-pentoside isomer II. All extracts revealed antioxidant activity and potential to inhibit some of the assayed bacteria; aqueous extracts of the aerial part and infusions of roots and rhizomes did not show cytotoxic effects on a non-tumor primary cell culture. This preliminary study provides suggestions of the biological potential associated with the empirical uses and knowledge of this species, in particular its bioactivities.


Assuntos
Fenóis , Componentes Aéreos da Planta , Extratos Vegetais , Raízes de Plantas , Ruscus/química , Animais , Antibacterianos/química , Antibacterianos/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Bactérias/efeitos dos fármacos , Linhagem Celular Tumoral , Hepatócitos , Humanos , Camundongos , Fenóis/química , Fenóis/farmacologia , Componentes Aéreos da Planta/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Raízes de Plantas/química , Cultura Primária de Células , Células RAW 264.7 , Ovinos , Suínos
17.
Molecules ; 26(5)2021 Mar 03.
Artigo em Inglês | MEDLINE | ID: mdl-33802535

RESUMO

The attractive colour characteristics of the flowers of the species Impatiens walleriana have been arousing great interest in the food industry, which is looking for potential natural sources of colouring ingredients. In this sense, the present work focused on the chemical and bioactive characterization of pink and orange flowers of I. walleriana. The phenolic compounds were determined by HPLC-DAD-ESI/MS; in addition, different bioactivities (antioxidant, antimicrobial, anti-inflammatory and cytotoxicity) were also analysed. Both samples studied showed significant amounts of phenolic compounds, especially phenolic acids, flavonoids, and anthocyanins, which justifies the excellent performance in the different bioactivities studied. The orange variety, despite having a greater variety of phenolic compounds, showed a total amount of compounds lower than the pink variety. Overall, the flowers of I. walleriana emerge as a promising resource to be explored by the food industry.


Assuntos
Antocianinas/análise , Flavonoides/análise , Flores/química , Hidroxibenzoatos/análise , Impatiens/química , Extratos Vegetais/farmacologia , Anti-Infecciosos/farmacologia , Anti-Inflamatórios/farmacologia , Antineoplásicos/farmacologia , Antioxidantes/farmacologia , Proliferação de Células , Flores/metabolismo , Impatiens/metabolismo , Células Tumorais Cultivadas
18.
Molecules ; 26(6)2021 Mar 13.
Artigo em Inglês | MEDLINE | ID: mdl-33805649

RESUMO

Medicinal and aromatic plants (MAPs), worldwide appreciated and used as condiments, dyes, and preservatives, possess several biological properties that justify their continuous application in the food industry. In the present study, the nutritional and chemical profiles, as well as the bioactive properties of four combinations of condiments, sold for seasoning poultry, meat, fish, and salads, were evaluated. Twenty-five phenolic compounds (HPLC-DAD-ESI/MS) were identified, with apigenin-O-malonyl-pentoside-hexoside as the major compound detected in all extracts. Oxalic and citric acids were identified in all mixtures (UFLC-PDA), as well as all the four tocopherol isoforms (HPLC-fluorescence). Regarding bioactivities, the mixtures for meat and salads (TBARS) and meat and poultry (OxHLIA) stood out for their antioxidant potential, whereas for the anti-inflammatory and antitumor properties, the mixtures revealing the greatest results were those for poultry and salad, respectively. In terms of antimicrobial activity, all the mixtures revealed the capacity to inhibit the growth of some bacterial strains. In brief, condiment mixtures showed to be a good source of bioactive compounds, as they confer health benefits, validating the importance of their inclusion in the human diet as a good dietary practice.


Assuntos
Condimentos/análise , Plantas Comestíveis/química , Plantas Medicinais/química , Animais , Anti-Infecciosos/química , Anti-Inflamatórios não Esteroides/química , Antineoplásicos Fitogênicos/química , Antioxidantes/química , Linhagem Celular Tumoral , Avaliação Pré-Clínica de Medicamentos , Humanos , Valor Nutritivo , Fenóis/química , Extratos Vegetais/análise
19.
Molecules ; 26(24)2021 Dec 10.
Artigo em Inglês | MEDLINE | ID: mdl-34946554

RESUMO

Cupressus sempervirens L., Juniperus communis L. and Cistus ladanifer L. are Mediterranean arboreal and shrub species that possess essential oils (EO) in their leaves and branches. This study aimed at characterizing the EOs obtained by steam distillation from the three species collected in different locations from Spain (Almazán, Andévalo, Barriomartín, Cerezal, Ermitas and Huéscar). For this purpose, volatiles composition was determined by GC-MS, and different bioactivities were evaluated. The highest content in terpenes was observed in C. sempervirens (Huéscar origin) followed by J. communis (Almazán origin), corresponding to 92% and 91.9% of total compounds, respectively. With exception of C. ladanifer from Cerezal that presented viridiflorol as the most abundant compound, all the three species presented in common the α-pinene as the major compound. The EOs from C. ladanifer showed high antibacterial potential, presenting MIC values from 0.3 to 1.25 mg/mL. Concerning other bioactivities, C. ladanifer EO revealed an oxidation inhibition of 83%, while J. communis showed cytotoxicity in the MCF-7 cell line, and C. sempervirens and C. ladanifer EOs exhibited the highest potential on NCI-H460 cell lines. Nevertheless, some EOs revealed toxicity against non-tumoral cells but generally presented a GI50 value higher than that of the tumor cell lines.


Assuntos
Antibacterianos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Cistus/química , Cupressus/química , Juniperus/química , Óleos Voláteis/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Compostos de Bifenilo/antagonistas & inibidores , Linhagem Celular , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Bactérias Gram-Negativas/efeitos dos fármacos , Humanos , Testes de Sensibilidade Microbiana , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Picratos/antagonistas & inibidores
20.
Molecules ; 25(11)2020 May 27.
Artigo em Inglês | MEDLINE | ID: mdl-32471297

RESUMO

Glycerol and alkanediols are being studied as alternative solvents to extract phytochemicals from plant material, often as hydrogen bond donors in deep eutectic solvents (DESs). Many of those alcohols are liquid at room temperature, yet studies of their use as extraction solvents are scarce. In this work, glycerol and a series of alkanediols (1,2-ethanediol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,2-pentanediol, 1,5-pentanediol, and 1,2-hexanediol) were studied for the extraction of phenolic compounds from Juglans regia L. leaves, a rich source of this class of bioactive compounds. The extraction yield was quantified, and the bioactivity of both extracts and pure solvents was evaluated by measuring the anti-inflammatory and cytotoxic activities. The solvents showing the best combined results were 1,2 and 1,3-propanediol, as their extracts presented a high amount of phenolic compounds, close to the results of ethanol, and similar cytotoxicity against cervical carcinoma cells, with no impact on non-tumor porcine liver cells in the studied concentration range. On the other hand, none of the extracts (and solvents) presented anti-inflammatory activity. Overall, the results obtained in this work contribute to the study of alternative solvents that could potentially be used also as formulation media, highlighting the importance of walnut leaves as a source of bioactive compounds.


Assuntos
Glicerol/química , Juglans/química , Compostos Fitoquímicos/química , Extratos Vegetais/química , Folhas de Planta/química , Óxido Nítrico/química , Fenóis/química , Solventes/química
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