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1.
Mar Drugs ; 22(6)2024 Jun 18.
Artículo en Inglés | MEDLINE | ID: mdl-38921595

RESUMEN

Porphyra sensu lato is one of the most economically significant and widely cultured and consumed algae in the world. Porphyra species present excellent nutraceutic properties due to their bioactive compounds (BACs). This research aimed to find the most efficient aqueous extraction method for BACs by examining alkaline and enzymatic hydrolysis. Alkaline hydrolysis with 2.5% sodium carbonate (SC) and at 80 °C proved optimal for extracting all BACs (phycobiliproteins, soluble proteins, polyphenols, and carbohydrates) except mycosporine-like amino acids (MAAs), which were best extracted with water only, and at 80 °C. Enzymatic hydrolysis, particularly with the 'Miura' enzymatic cocktail (cellulase, xylanase, glycoside hydrolase, and ß-glucanase), showed superior results in extracting phycoerythrin (PE), phycocyanin (PC), soluble proteins, and carbohydrates, with increases of approximately 195%, 510%, 890%, and 65%, respectively, compared to the best alkaline hydrolysis extraction (2.5% SC and 80 °C). Phenolic content analysis showed no significant difference between the 'Miura' cocktail and 2.5% SC treatments. Antioxidant activity was higher in samples from alkaline hydrolysis, while extraction of MAAs showed no significant difference between water-only and 'Miura' treatments. The study concludes that enzymatic hydrolysis improves the efficiency of BACs extraction in P. linearis, highlighting its potential for the nutraceutical industry, and especially with respect to MAAs for topical and oral UV-photoprotectors.


Asunto(s)
Antioxidantes , Suplementos Dietéticos , Porphyra , Porphyra/química , Hidrólisis , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Carbonatos/química , Fenoles/aislamiento & purificación , Fenoles/química , Carbohidratos/química
2.
Int J Mol Sci ; 25(12)2024 Jun 13.
Artículo en Inglés | MEDLINE | ID: mdl-38928246

RESUMEN

Bioactive compounds that can be recovered by the solid wastes of the olive oil sector, such as polyphenols, are known for their significant antioxidant and antimicrobial activities with potential application in nutraceutical, cosmetic, and food industries. Given that industrial demands are growing, and the polyphenol market value is ever increasing, a systematic study on the recovery of natural antioxidant compounds from olive pomace using ultrasound-assisted extraction (UAE) was conducted. Single-factor parameters, i.e., the extraction solvent, time, and solid-to-liquid ratio, were investigated evaluating the total phenolic content (TPC) recovery and the antioxidant activity of the final extract. The acetone-water system (50% v/v, 20 min, 1:20 g mL-1) exhibited the highest total phenolic content recovery (168.8 ± 5.5 mg GAE per g of dry extract). The olive pomace extract (OPE) was further assessed for its antioxidant and antibacterial activities. In DPPH, ABTS, and CUPRAC, OPE exhibited an antioxidant capacity of 413.6 ± 1.9, 162.72 ± 3.36 and 384.9 ± 7.86 mg TE per g of dry extract, respectively. The antibacterial study showed that OPE attained a minimum inhibitory activity (MIC) of 2.5 mg mL-1 against E. coli and 10 mg mL-1 against B. subtilis. Hydroxytyrosol and tyrosol were identified as the major phenolic compounds of OPE. Furthermore, active chitosan-polyvinyl alcohol (CHT/PVA) films were prepared using different OPE loadings (0.01-0.1%, w/v). OPE-enriched films showed a dose-dependent antiradical scavenging activity reaching 85.7 ± 4.6% (ABTS) and inhibition growth up to 81% against B. subtilis compared to the control film. Increased UV light barrier ability was also observed for the films containing OPE. These results indicate that OPE is a valuable source of phenolic compounds with promising biological activities that can be exploited for developing multifunctional food packaging materials.


Asunto(s)
Antibacterianos , Antioxidantes , Olea , Fenoles , Extractos Vegetales , Olea/química , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/farmacología , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Fenoles/química , Fenoles/aislamiento & purificación , Fenoles/farmacología , Fenoles/análisis , Embalaje de Alimentos , Polifenoles/química , Polifenoles/farmacología , Polifenoles/aislamiento & purificación , Ondas Ultrasónicas , Pruebas de Sensibilidad Microbiana
3.
Molecules ; 29(12)2024 Jun 17.
Artículo en Inglés | MEDLINE | ID: mdl-38930937

RESUMEN

Polyphenols from agro-food waste represent a valuable source of bioactive molecules that can be recovered to be used for their functional properties. Another option is to use them as starting material to generate molecules with new and better properties through semi-synthesis. A proanthocyanidin-rich (PACs) extract from avocado peels was used to prepare several semi-synthetic derivatives of epicatechin by acid cleavage in the presence of phenol and thiol nucleophiles. The adducts formed by this reaction were successfully purified using one-step centrifugal partition chromatography (CPC) and identified by chromatographic and spectroscopic methods. The nine derivatives showed a concentration-dependent free radical scavenging activity in the DPPH assay. All compounds were also tested against a panel of pathogenic bacterial strains formed by Listeria monocytogenes (ATCC 7644 and 19115), Staphylococcus aureus (ATCC 9144), Escherichia coli (ATCC 11775 and 25922), and Salmonella enterica (ATCC 13076). In addition, adducts were tested against two no-pathogenic strains, Limosilactobacillus fermentum UCO-979C and Lacticaseibacillus rhamnosus UCO-25A. Overall, thiol-derived adducts displayed antimicrobial properties and, in some specific cases, inhibited biofilm formation, particularly in Listeria monocytogenes (ATCC 7644). Interestingly, phenolic adducts were inactive against all the strains and could not inhibit its biofilm formation. Moreover, depending on the structure, in specific cases, biofilm formation was strongly promoted. These findings contribute to demonstrating that CPC is a powerful tool to isolate new semi-synthetic molecules using avocado peels as starting material for PACc extraction. These compounds represent new lead molecules with antioxidant and antimicrobial activity.


Asunto(s)
Antioxidantes , Catequina , Persea , Proantocianidinas , Persea/química , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/síntesis química , Proantocianidinas/química , Proantocianidinas/farmacología , Proantocianidinas/síntesis química , Proantocianidinas/aislamiento & purificación , Catequina/química , Catequina/farmacología , Extractos Vegetales/química , Extractos Vegetales/farmacología , Pruebas de Sensibilidad Microbiana , Antiinfecciosos/farmacología , Antiinfecciosos/química , Antiinfecciosos/síntesis química , Compuestos de Sulfhidrilo/química , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/síntesis química , Antibacterianos/aislamiento & purificación , Fenoles/química , Fenoles/farmacología , Fenoles/aislamiento & purificación , Fenoles/síntesis química
4.
Fitoterapia ; 176: 105986, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38703914

RESUMEN

In the present study, we have attempted a comprehensive assessment of the possible radioprotective efficacy of Pterocarpus santalinus aqueous extract (PSAE). All the studied models were gamma-irradiated with prior treatment with PSAE. First, the content of total phenols (4.061 µg/mg gallic acid equivalents), flavonoids (6.616 µg/mg quercetin equivalents), and tannins (0.008 mg/L of PSAE) were determined spectrophotometrically. Second, UHPLC-HRMS analysis was performed to identify the possible radioprotectors. Of those, santalins A & B are known for their usage as natural color in foods and alcoholic beverages identified in PSAE. Treatment was well tolerated with no side effects from PSAE. Later, it was shown that radiation-induced lethality significantly amended in PSAE-treated spleen lymphocytes as evidenced by reduced elevated levels of ROS and lipid peroxidation, restored total thiols and GSH: GSSG, inhibited DNA DSBs and cell death. Furthermore, an immunomodulation study was carried out because radiation exposure induces an inflammatory response. Our study shows that PSAE suppressed concanavalin A-induced T-cell proliferation as evidenced by CFSE dye dilution and CD69 antibody staining methods. Taken together, the current study explored the protective efficacy of PSAE from gamma radiation-inflicted injuries and hence we recommend PSAE as a potent radioprotective formulation.


Asunto(s)
Extractos Vegetales , Pterocarpus , Protectores contra Radiación , Animales , Extractos Vegetales/farmacología , Extractos Vegetales/química , Protectores contra Radiación/farmacología , Ratones , Pterocarpus/química , Rayos gamma , Masculino , Bazo/efectos de los fármacos , Peroxidación de Lípido/efectos de los fármacos , Fitoquímicos/farmacología , Fitoquímicos/aislamiento & purificación , Especies Reactivas de Oxígeno/metabolismo , Fenoles/farmacología , Fenoles/aislamiento & purificación , Flavonoides/farmacología , Linfocitos/efectos de los fármacos , Linfocitos/efectos de la radiación , Linfocitos T/efectos de los fármacos , Linfocitos T/efectos de la radiación
5.
Comput Biol Chem ; 110: 108087, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38718496

RESUMEN

INTRODUCTION: Diabetes Mellitus is the metabolic disorder most prevalent globally, accounting for a substantial morbidity rate. The conventional drugs available for the management of diabetes are either expensive or lack the required efficacy. The purpose of this research is to isolate and characterize an active phytoconstituent from Coccinia grandis and assess its anti-diabetic properties. METHODS AND MATERIALS: Stems of Coccinia grandis are subjected to successive extraction and isolation. The isolated compound by column chromatography was characterized by FTIR (fourier-transform infrared), 1 H NMR (proton nuclear magnetic resonance), and Mass spectroscopy. The antidiabetic potential of the isolated compound was evaluated by in-vitro alpha-amylase inhibitory activity. Further, the compound was subjected to molecular docking studies to study its interaction with the human pancreatic alpha-amylase (Molegro Virtual Docker) as well to determine the pharmacokinetic and toxicity profile using computational techniques (OSIRIS property explorer, Swiss ADME, pkCSM, and PreADMET). RESULTS: The characterization of the compound suggests the structure to be 2,4-ditertiary butyl phenol. The in-vitro alpha-amylase inhibitory study indicated a concentration-dependent inhibition and the IC50 (median lethal dose) value of the isolated compound was found to be 64.36 µg/ml. The docking study with the A chain of receptor 5EMY yielded a favorable docking score of -81.48 Kcal mol-1, suggesting that the compound binds to the receptor with high affinity through electrostatic, hydrophobic, and hydrogen bonds. Furthermore, the silico ADME analysis of the compound revealed improved metabolism, a skin permeability of -3.87 cm/s, gastrointestinal absorption of 95.48 %, and a total clearance of 0.984 log ml min-1 kg-1. In silico toxicity analysis also predicted cutaneous irritations but no carcinogenicity, mutagenicity, or hepatotoxicity. CONCLUSION: The data suggested that the isolated compound (2, 4-tertiary butyl phenol) has the potential to inhibit the alpha-amylase activity and possess optimal ADME properties as well as tolerable side effects.


Asunto(s)
Simulación del Acoplamiento Molecular , Fenoles , alfa-Amilasas , Humanos , alfa-Amilasas/antagonistas & inhibidores , alfa-Amilasas/metabolismo , Fenoles/química , Fenoles/farmacología , Fenoles/aislamiento & purificación , Cucurbitaceae/química , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/farmacología , Inhibidores Enzimáticos/aislamiento & purificación , Estructura Molecular , Hipoglucemiantes/química , Hipoglucemiantes/farmacología , Hipoglucemiantes/aislamiento & purificación
6.
Phytochemistry ; 223: 114122, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38710376

RESUMEN

Quantitative analysis of Rumex nepalensis var. remotiflorus revealed that its roots contain rich anthraquinones, which has emodin, chrysophanol, and physcion contents of up to 0.30, 0.67, and 0.98 mg/g, respectively. Further phytochemical study led to the isolation and purification of seven undescribed phenolic constituents, including one flavan derivative with a 13-membered ring, polygorumin A (1), two dianthrone glucosides, polygonumnolides F and G (2, 3), two diphenylmethanones, rumepalens A and B (4, 5), and a pair of epimeric oxanthrone C-glucosides, rumejaposides K and L (6a, 6b) from the roots of R. nepalensis var. remotiflorus. Furthermore, 1 undescribed natural product, 1-ß-D-glucoside-6'-[(2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate]-3-hydroxy-5-methylphenyl (19), and 21 known phenolic compounds were obtained from the aforementioned plant for the first time. Their structures were elucidated through extensive spectroscopic data analysis. Notably, compounds 1, 4-5, and 7-9 exhibited inhibitory activity on α-glucosidase with IC50 values ranging from 1.61 ± 0.17 to 32.41 ± 0.87 µM. In addition, the isolated dianthrone, chrysophanol bianthrone (14), showed obvious cytotoxicity against four human cancer cell lines (HL-60, SMMC-7721, A-549, and MDA-MB-231) with IC50 values ranging from 3.81 ± 0.17 to 35.15 ± 2.24 µM. In silico target prediction and molecular docking studies demonstrated that the mechanism of the anticancer activity of 14 may be related to the interaction with protein kinase CK2.


Asunto(s)
Antineoplásicos Fitogénicos , Inhibidores de Glicósido Hidrolasas , Fenoles , Rumex , alfa-Glucosidasas , Humanos , Fenoles/farmacología , Fenoles/química , Fenoles/aislamiento & purificación , Inhibidores de Glicósido Hidrolasas/farmacología , Inhibidores de Glicósido Hidrolasas/química , Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Rumex/química , alfa-Glucosidasas/metabolismo , alfa-Glucosidasas/efectos de los fármacos , Antineoplásicos Fitogénicos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Estructura Molecular , Ensayos de Selección de Medicamentos Antitumorales , Simulación del Acoplamiento Molecular , Relación Estructura-Actividad , Línea Celular Tumoral , Raíces de Plantas/química , Relación Dosis-Respuesta a Droga , Proliferación Celular/efectos de los fármacos
7.
Food Chem ; 451: 139500, 2024 Sep 01.
Artículo en Inglés | MEDLINE | ID: mdl-38696941

RESUMEN

Deep eutectic solvent (DES) combined with ultrasonic-assisted extraction was employed as an environmentally friendly technique for extracting antioxidant phenolic compounds from Neem leaves in place of organic solvents. Choline chloride-Ethylene glycol (1:2) with 40% V/V water content (DES-1) was investigated as a potential total phenolic content extractant (38.2 ± 1.2 mg GAE/g DW, where GAE: gallic acid equivalent, DW: dry weight). The optimal operational parameters assessed using single-factor experiments to maximize the total phenolic compounds content were as follows: extraction time of 30 min, 40% V/V water content, liquid-solid ratio of 15:1, and room temperature. Additionally, the in-vitro antioxidant experiments (2,2-diphenyl-1- picrylhydrazyl radical scavenging assay and ferric reducing antioxidant power assay) demonstrated the DES-1-based extract of Neem leaves as a potent antioxidant agent, compared to traditional solvents. Moreover, microscopic morphological analysis supported the effectiveness of DES-1 for the noticeable alteration in the fiber surface structure of Neem leaves after extraction which benefited in the release of polyphenols from these leaves. Eventually, the mass analysis of the extract disclosed the presence of eleven polyphenols in the extract. The Green Analytical Procedure Index revealed the greenness of the extraction method.


Asunto(s)
Antioxidantes , Disolventes Eutécticos Profundos , Tecnología Química Verde , Fenoles , Extractos Vegetales , Hojas de la Planta , Hojas de la Planta/química , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Fenoles/química , Fenoles/aislamiento & purificación , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Disolventes Eutécticos Profundos/química , Azadirachta/química , Fraccionamiento Químico/métodos , Ultrasonido , Solventes/química
8.
Fitoterapia ; 175: 105923, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38554886

RESUMEN

Cervical cancer is a type of cancer which affects the cervix cells. The conventional treatments for cervical cancer including surgery, chemotherapy, and radiotherapy are only effective in premature stages and less effective in late stages of this tumor. Therefore, the therapeutic strategies based on biologically active substances from plants are needed to develop for the treatment of cervical cancer. The aim of the present study was to assess in vivo toxicity, hematological and biochemical blood parameters in Wistar rats fed Retama sphaerocarpa aqueous leaf extract (RS-AE), as well as to perform in silico molecular docking studies and dynamic simulation of phenolic compounds against HPV16 oncoprotein E6 in order to identify potential inhibitors. RS-AE was found not to induce acute or sub-acute oral toxicity or significant alterations in hematological and biochemical blood parameters in Wistar rats. A total of 11 phenolic compounds were identified in RS-AE, including dihydrodaidzein glucuronide, chrysoperiol pentoside, genistin and vitexin, which turned out to have the highest binding affinity to HPV16 oncoprotein E6. Based on these results, these RS-AE phenolic compounds could be used as natural drugs against the HPV16 E6 oncoprotein.


Asunto(s)
Simulación del Acoplamiento Molecular , Proteínas Oncogénicas Virales , Fenoles , Extractos Vegetales , Hojas de la Planta , Ratas Wistar , Proteínas Represoras , Animales , Extractos Vegetales/farmacología , Extractos Vegetales/química , Ratas , Fenoles/farmacología , Fenoles/aislamiento & purificación , Fenoles/química , Proteínas Oncogénicas Virales/antagonistas & inhibidores , Hojas de la Planta/química , Proteínas Represoras/antagonistas & inhibidores , Femenino , Fitoquímicos/farmacología , Fitoquímicos/aislamiento & purificación , Estructura Molecular , Masculino
9.
Chem Biodivers ; 21(5): e202400272, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38489001

RESUMEN

Within a study focused on Sinapis pubescens subsp. pubescens wild from Sicily (Italy), an edible species still unexplored, our earlier published work has demonstrated good in vitro antioxidant properties for the flower and leaf hydroalcoholic extracts, exhibiting quite different qualitative-quantitative phenolic profiles. Herein, further research was designed to elucidate the role played by phenolic compounds in the different antioxidant mechanisms highlighted for the extracts. To achieve this goal, the crude extracts were subjected to liquid-liquid partitioning with solvents of increasing polarity; then, the fractions were investigated for their antioxidant properties using different in vitro assays. For both flowers and leaves, the ethyl acetate fractions exhibited the best activity in DPPH and reducing power assays, followed by n-butanol. The total phenolic content determination indicated these fractions as the phenolic-rich ones, which were characterized by HPLC-PDA/ESI-MS analysis. Conversely, the phenolic-rich fractions did not show any chelating activity, which was highlighted for the more hydrophobic ones.


Asunto(s)
Antioxidantes , Compuestos de Bifenilo , Flores , Fenoles , Extractos Vegetales , Hojas de la Planta , Hojas de la Planta/química , Fenoles/química , Fenoles/aislamiento & purificación , Fenoles/farmacología , Flores/química , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/farmacología , Extractos Vegetales/aislamiento & purificación , Compuestos de Bifenilo/antagonistas & inhibidores , Brassicaceae/química , Picratos/antagonistas & inhibidores , Cromatografía Líquida de Alta Presión
10.
Int J Biol Macromol ; 266(Pt 1): 131147, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38537857

RESUMEN

Seaweed, a diverse group of marine macroalgae, has emerged as a rich source of bioactive compounds with numerous health-promoting properties. Among these, phenolic compounds have garnered significant attention for their diverse therapeutic applications. This review examines the methodologies employed in the extraction and purification of phenolic compounds from seaweed, emphasizing their importance in unlocking the full potential of these oceanic treasures. The article provides a comprehensive overview of the structural diversity and biological activities of seaweed-derived phenolics, elucidating their antioxidant, anti-inflammatory, and anticancer properties. Furthermore, it explores the impact of extraction techniques, including conventional methods and modern green technologies, on the yield and quality of phenolic extracts. The purification strategies for isolating specific phenolic compounds are also discussed, shedding light on the challenges and advancements in this field. Additionally, the review highlights the potential applications of seaweed-derived phenolics in various industries, such as pharmaceuticals, cosmetics, and functional foods, underscoring the economic value of these compounds. Finally, future perspectives and research directions are proposed to encourage continued exploration of seaweed phenolics, fostering a deeper understanding of their therapeutic potential and promoting sustainable practices in the extraction and purification processes. This comprehensive review serves as a valuable resource for researchers, industry professionals, and policymakers interested in harnessing the untapped potential of phenolic compounds from seaweed for the betterment of human health and environmental sustainability.


Asunto(s)
Antioxidantes , Fenoles , Algas Marinas , Algas Marinas/química , Fenoles/aislamiento & purificación , Fenoles/química , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Humanos , Antiinflamatorios/química , Antiinflamatorios/farmacología , Antiinflamatorios/aislamiento & purificación , Fraccionamiento Químico/métodos , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Antineoplásicos/farmacología , Extractos Vegetales/química , Extractos Vegetales/farmacología , Extractos Vegetales/aislamiento & purificación , Animales
11.
Food Chem ; 448: 139104, 2024 Aug 01.
Artículo en Inglés | MEDLINE | ID: mdl-38547711

RESUMEN

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


Asunto(s)
Lens (Planta) , Fenoles , Proteínas de Plantas , Lens (Planta)/química , Fenoles/química , Fenoles/aislamiento & purificación , Proteínas de Plantas/química , Proteínas de Plantas/aislamiento & purificación , Concentración de Iones de Hidrógeno , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Amiloide/química , Fraccionamiento Químico/métodos
12.
Phytochem Anal ; 35(4): 889-902, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38369344

RESUMEN

INTRODUCTION: The species Lantana camara is used in folk medicine. The biological activities of this medicinal plant are attributable to the presence of various derivatives of triterpenoids and phenolic compounds present in its preparations, indicating excellent economic potential. OBJECTIVE: In this study, the operational conditions of ultrasound-assisted extraction (UAE) and microwave-assisted extraction (MAE) were optimized using Box-Behnken design to improve the total phenolic content (TPC) recovered in hydroethanolic extracts of L. camara leaves. MATERIAL AND METHODS: The TPC, total flavonoid content (TFC), and antioxidant activities of the hydroalcoholic extracts of L. camara, prepared by UAE and MAE under the optimized extraction conditions, were compared with those of the extracts obtained by conventional extraction methods. RESULTS: Under the optimal conditions, the extracts obtained by UAE (35% ethanol, 25 min, and a solvent-to-solid ratio of 60:1 mL/g) and by MAE (53% ethanol, 15 min, and 300 W) provided high yields of 32.50% and 38.61% and TPC values of 102.89 and 109.83 mg GAE/g DW, respectively. The MAE extract showed the best results with respect to TPC, TFC, and antioxidant activities, followed by extracts obtained by UAE, Soxhlet extraction, decoction, maceration, and infusion, in that order. CONCLUSION: The results obtained indicate that L. camara may be used as an important source of antioxidant phenolic compounds to obtain products with high biological and economic potential, especially when the extraction process is performed under appropriate conditions using MAE and/or UAE, employing environmentally friendly solvents such as water and ethanol.


Asunto(s)
Antioxidantes , Lantana , Microondas , Fenoles , Extractos Vegetales , Hojas de la Planta , Hojas de la Planta/química , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Antioxidantes/análisis , Lantana/química , Fenoles/análisis , Fenoles/aislamiento & purificación , Fenoles/química , Extractos Vegetales/química , Extractos Vegetales/farmacología , Espectrometría de Masas/métodos , Flavonoides/análisis , Flavonoides/aislamiento & purificación , Ondas Ultrasónicas , Ultrasonido/métodos
13.
Molecules ; 28(17)2023 Aug 25.
Artículo en Inglés | MEDLINE | ID: mdl-37687080

RESUMEN

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


Asunto(s)
Fenoles , Fitoquímicos , Neoplasias Cutáneas , Especias , Neoplasias Cutáneas/tratamiento farmacológico , Neoplasias Cutáneas/prevención & control , Fenoles/aislamiento & purificación , Fenoles/farmacología , Fenoles/uso terapéutico , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Fitoquímicos/uso terapéutico , Humanos
14.
Molecules ; 28(17)2023 Aug 29.
Artículo en Inglés | MEDLINE | ID: mdl-37687138

RESUMEN

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


Asunto(s)
Antioxidantes , Pan , Valor Nutritivo , Fenoles , Semillas , Triticum , Triticum/química , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Germinación , Semillas/química , Pan/análisis , Solubilidad , Fenoles/química , Fenoles/aislamiento & purificación
15.
J Ethnopharmacol ; 310: 116378, 2023 Jun 28.
Artículo en Inglés | MEDLINE | ID: mdl-36924865

RESUMEN

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


Asunto(s)
Cinamatos , Melanoma , Monofenol Monooxigenasa , Fenoles , Animales , Ratones , Cosmecéuticos , Inhibidores Enzimáticos/farmacología , Inhibidores Enzimáticos/química , Melaninas/metabolismo , Melanoma/tratamiento farmacológico , Melanoma/metabolismo , Monofenol Monooxigenasa/efectos de los fármacos , Fenoles/química , Fenoles/aislamiento & purificación , Fenoles/farmacología , Prunus , Cinamatos/química , Cinamatos/aislamiento & purificación , Cinamatos/farmacología , Antineoplásicos/farmacología
16.
J Food Sci ; 87(7): 2831-2846, 2022 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-35661363

RESUMEN

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


Asunto(s)
Antioxidantes , Fagopyrum , Aceites , Fenoles , Antioxidantes/análisis , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Emulsiones/química , Etanol/química , Fagopyrum/química , Flavonoides/análisis , Ácido Gálico/análisis , Glicósidos/análisis , Glicósidos/aislamiento & purificación , Glicósidos/farmacología , Aceites/química , Fenoles/análisis , Fenoles/aislamiento & purificación , Fenoles/farmacología , Extractos Vegetales/análisis , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Polifenoles/análisis , Polifenoles/aislamiento & purificación , Polifenoles/farmacología , Semillas/química
17.
Food Res Int ; 157: 111381, 2022 07.
Artículo en Inglés | MEDLINE | ID: mdl-35761637

RESUMEN

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


Asunto(s)
Antioxidantes/química , Citrus , Hesperidina , Compuestos de Calcio/química , Hesperidina/química , Hesperidina/aislamiento & purificación , Óxidos/química , Fenoles/química , Fenoles/aislamiento & purificación , Solventes
18.
Molecules ; 27(4)2022 Feb 21.
Artículo en Inglés | MEDLINE | ID: mdl-35209235

RESUMEN

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


Asunto(s)
Antineoplásicos/química , Antineoplásicos/farmacología , Organismos Acuáticos/química , Fenoles/química , Fenoles/farmacología , Antineoplásicos/aislamiento & purificación , Organismos Acuáticos/metabolismo , Productos Biológicos/química , Productos Biológicos/aislamiento & purificación , Productos Biológicos/farmacología , Humanos , Redes y Vías Metabólicas , Fenoles/aislamiento & purificación , Fenoles/metabolismo , Relación Estructura-Actividad
19.
Molecules ; 27(2)2022 Jan 14.
Artículo en Inglés | MEDLINE | ID: mdl-35056847

RESUMEN

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


Asunto(s)
Cosmecéuticos/farmacología , Inhibidores Enzimáticos/farmacología , Olea/química , Fenoles/aislamiento & purificación , Fitoquímicos/farmacología , Extractos Vegetales/farmacología , Hojas de la Planta/química , Cosmecéuticos/aislamiento & purificación , Ácido Láctico/química , Extractos Vegetales/aislamiento & purificación , Polímeros/química , Glicoles de Propileno/química
20.
Biomed Pharmacother ; 145: 112415, 2022 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-34775236

RESUMEN

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


Asunto(s)
Antioxidantes/farmacología , Chlorella/química , Enfermedades Neurodegenerativas/prevención & control , Fármacos Neuroprotectores/farmacología , Animales , Antioxidantes/aislamiento & purificación , Apoptosis/efectos de los fármacos , Hidroxitolueno Butilado/aislamiento & purificación , Hidroxitolueno Butilado/farmacología , Supervivencia Celular/efectos de los fármacos , Depuradores de Radicales Libres/aislamiento & purificación , Depuradores de Radicales Libres/farmacología , Peróxido de Hidrógeno/toxicidad , Potencial de la Membrana Mitocondrial/efectos de los fármacos , Enfermedades Neurodegenerativas/fisiopatología , Fármacos Neuroprotectores/aislamiento & purificación , Estrés Oxidativo/efectos de los fármacos , Células PC12 , Fenoles/aislamiento & purificación , Fenoles/farmacología , Fitol/aislamiento & purificación , Fitol/farmacología , Ratas , Especies Reactivas de Oxígeno/metabolismo
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