RESUMO
Bacillus megaterium is particularly known for its abundance in soils and its plant growth promotion. To characterize the metabolites excreted by this specie, we performed successive liquid/liquid extractions from bacteria culture medium with different polarity solvents (cyclohexane, dichloromethane, ethyl acetate and butanol) to separate the metabolites in different polarity groups. The extracts were characterized regarding their total phenolic content, the amount of reducing sugar, the concentration of primary amines and proteins, their chromatographic profile by HPLC-DAD-ELSD and their chemical identification by GC-MS. Among the 75 compounds which are produced by the bacteria, 19 identifications were for the first time found as metabolites of B. megaterium and 23 were described for the first time as metabolites in Bacillus genus. The different extracts containing B. megaterium metabolites showed interesting agronomic activity, with a global inhibition of seed germination rates of soya, sunflower, corn and ray grass, but not of corn, compared to culture medium alone. Our results suggest that B. megaterium can produce various metabolites, like butanediol, cyclic dipeptides, fatty acids, and hydrocarbons, with diverse effects and sometimes with opposite effects in order to modulate its response to plant growth and adapt to various environmental effects. These findings provide new insight into bioactive properties of this species for therapeutic uses on plants.
Assuntos
Bacillus megaterium , Antioxidantes/metabolismo , Cromatografia Gasosa-Espectrometria de MassasRESUMO
Oleanolic acid (OA) is a vegetable chemical that is present naturally in a number of edible and medicinal botanicals. It has been extensively studied by medicinal chemists and scientific researchers due to its biological activity against a wide range of diseases. A significant number of researchers have synthesized a variety of analogues of OA by modifying its structure with the intention of creating more potent biological agents and improving its pharmaceutical properties. In recent years, chemical and enzymatic techniques have been employed extensively to investigate and modify the chemical structure of OA. This review presents recent advancements in medical chemistry for the structural modification of OA, with a special focus on the biotransformation, semi-synthesis and relationship between the modified structures and their biopharmaceutical properties.
Assuntos
Ácido Oleanólico , Ácido Oleanólico/química , Ácido Oleanólico/análogos & derivados , Ácido Oleanólico/síntese química , Ácido Oleanólico/metabolismo , Humanos , Biotransformação , Relação Estrutura-Atividade , Estrutura Molecular , AnimaisRESUMO
Kombucha is a traditional healthy beverage usually made by the fermentation of sweetened tea with a symbiotic culture of bacteria and yeast. The consumption of kombucha is associated with numerous health benefits and therefore the beverage has attracted the attention of consumers worldwide. Non-typical substrates (fruits, vegetables, plants, herbs, dairy, and by-products) are being inoculated with the kombucha consortium in an attempt to develop new products. This review paper reviews the fermentation parameters for different non-tea substrates used to make kombucha, in addition to the findings obtained in terms of physico-chemical analysis, biological activities and sensory evaluation.
Assuntos
Bebidas , Leveduras , Bebidas/microbiologia , Bactérias , FermentaçãoRESUMO
Limonium. Mill is a genus of flowering plants belonging to the Plumbaginaceae family. The present study aimed to compare two Limonium species (L.â pruinosum Kuntze and L.â tunetanum (Barratte & Bonnet) Maire) in terms of their chemical composition and bioactivity. Chemical profiling showed that the methanolic (MeOH) extracts of both species were the most enriched with total phenolic (TP) and total flavonoid (TF) contents. The TFC were higher in L.â tunetanum compared to L.â pruinosum. HPLC-DAD analysis showed that distinctly the gallic acid and L-tyrosine 7-amido-4-methylcoumarin were the main compounds for L.â pruinosum and L.â tunetanum, respectively. For both Limonium. Mil species, the MeOH extracts displayed the highest antioxidant with IC50 of 7.7 and 8.4â µg/mL for L.â pruinosum and L.â tunetanum, respectively. The highest anti-15-lipoxygnase activity was recorded in the ethyl acetate (IC50 =14.2â µg/mL) and Methanol (IC50 =15.6â µg/mL) extracts for L.â pruinosum. However, for L.â tunetanum the best activity was recorded for dichloromethane extract (IC50 =10.4â µg/mL). L.â pruinosum extracts displayed the highest cytotoxic activity against MCF-7 and HCT-116â cell lines compared to L.â tunetanum ones. The obtained bioactivity discrepancy between Limonium. Mill species was discussed in relation to the organic extract chemical richness.
Assuntos
Antineoplásicos , Plumbaginaceae , Antioxidantes/farmacologia , Antioxidantes/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Plumbaginaceae/química , Áreas Alagadas , Flavonoides/química , Flavonoides/farmacologiaRESUMO
Rutabaga, also known as swede and scientifically classified as Brassica napus napobrassica, is a biennial edible root vegetable that belongs to the Brassica genus and is widely cultivated in North Europe and North America. The present study highlights both the phytochemical profile and the in vitro biological properties of rutabaga seed extracts obtained through maceration using solvents of increasing polarity, namely, cyclohexane (CYHA), dichloromethane (DCM), ethyl acetate (EtOAc), methanol (MeOH), and water (H2O). HPLC-DAD was used to identify and quantify phenolic compounds, while volatile compounds were detected using GC-MS. The in vitro antioxidant capacity of the rutabaga seed extracts was evaluated through DPPH free radical scavenging activity. The in vitro anti-inflammatory activity (15-lipoxygenase (15-LOX) enzyme) was determined spectrophotometrically at the same concentration. Additionally, the cytotoxicity of the seed extracts was evaluated against human colon adenocarcinoma cells (Caco-2) and human embryonic kidney cells (HEK-293) using the MTT assay. The rutabaga seed extracts obtained from EtOAc, MeOH, and H2O were particularly rich in reducing sugars, ranging from 189.87 to 473.75 mg/g DW. The MeOH extract displayed the highest concentration of both sugars and polyphenols. Phytochemically, the HPLC-DAD analysis revealed the presence of four phenolic compounds in the tested extracts, including (±) synephrine, gallic acid, p-coumaric acid, and trans-ferulic acid, newly discovered in rutabaga organs. Moreover, a total of ten volatile compounds were identified through GC-MS analysis, both before and after derivatization. At a concentration of 50 µg/mL, the methanol extract exhibited high antioxidant activity with 52.95% inhibition, while CYHA, DCM, and EtOAc exhibited moderate anti-15-LOX activity with less than 30% inhibition. Except for DCM and aqueous extracts, rutabaga seeds did not exhibit any anti-proliferative potential against Caco-2 cell lines. Interestingly, no cytotoxicity was registered for any of the seed extracts against the normal cell line HEK-293. Overall, the obtained data highlight the potential utilization of rutabaga seeds as a source of bioactive compounds in various fields, including pharmaceuticals, nutraceuticals, and functional foods.
Assuntos
Adenocarcinoma , Brassica napus , Brassica , Neoplasias do Colo , Humanos , Células CACO-2 , Células HEK293 , Metanol , Antioxidantes/farmacologia , Extratos Vegetais/farmacologiaRESUMO
Among the family of sugarcane spirits, those made from juice are diverse and often produced in a traditional way. They must be distinguished from other sugarcane spirits, which are more widely produced and made from other sugarcane derivatives, such as molasses. These alcoholic beverages contribute significantly to the socio-economic development of many countries. However, despite ancestral know-how, there is a lack of contemporary data required to characterize some sugarcane juice spirits (SCJSs) and to overcome the current and future threats that producers will have to face. While preserving their authenticity and specificity, SCJS producers expect to improve and ensure sufficient yield and a superior quality product. Even if the scientific knowledge on these spirits is not comparable, the available data could help identify the critical points to be improved in the making process. This review aims to present the main SCJSs encountered worldwide, defining their specific features through some important aspects with, notably, references to the complex notion of terroir. To continue, we discuss the main steps of the SCJS process from harvesting to aging. Finally, we expose an inventory of SCJS's chemical compositions and of their sensory description that define the specific organoleptic properties of these spirits.
Assuntos
Saccharum , Saccharum/química , Bebidas Alcoólicas/análise , MelaçoRESUMO
This work aimed to evaluate the biological activities of 20 flavones (M1 to M20) and discuss their structure-activity relationships. In vitro assays were established to assess their numerous biological activities (anti-α-amylase, anti-acetylcholinesterase, anti-xanthine oxidase, anti-superoxide dismutase, and anticancer cell lines (HCT-116, MCF7, OVCAR-3, IGROV-1, and SKOV-3 cells lines)). An in silico docking study was also established in order to find the relationship between the chemical structure and the biological activities. In vitro tests revealed that M5 and M13 were the most active in terms of anti-α-amylase activity (IC50 = 1.2 and 1.4 µM, respectively). M17 was an inhibitor of xanthine oxidase (XOD) and performed better than the reference (allopurinol), at IC50 = 0.9 µM. M7 presented interesting anti-inflammatory (IC50 = 38.5 µM), anti-supriode dismutase (anti-SOD) (IC50 = 31.5 µM), and anti-acetylcholinesterase (IC50 = 10.2 µM) activities. Those abilities were in concordance with its high scavenging activity in antioxidant ABTS and DPPH assays, at IC50 = 6.3 and 5.2 µM, respectively. Selectivity was detected regarding cytotoxic activity for those flavones. M1 (IC50 = 35.9 µM) was a specific inhibitor to the MCF7 cancer cell lines. M3 (IC50 = 44.7 µM) and M15 (IC50 = 45.6 µM) were particularly potent for the OVCAR-3 cell line. M14 (IC50 = 4.6 µM) contributed more clearly to inhibiting the colon cancer cell line (HCT116). M7 (IC50 = 15.6 µM) was especially active against the ovarian SKOV human cancer cell line. The results of the biological activities were supported by means of in silico molecular docking calculations. This investigation analyzed the contribution of the structure-activity of natural flavones in terms of their biological properties, which is important for their future application against diseases.
Assuntos
Antineoplásicos , Flavonas , Neoplasias Ovarianas , Humanos , Feminino , Flavonas/farmacologia , Simulação de Acoplamento Molecular , Apoptose , Linhagem Celular Tumoral , Antineoplásicos/farmacologia , Antineoplásicos/química , Relação Estrutura-Atividade , Superóxido Dismutase/metabolismo , Xantina Oxidase , Amilases/metabolismo , Estrutura Molecular , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Proliferação de CélulasRESUMO
The Salvia fruticosa (Mill.) is the most medicinal plant used in Lebanon. The aim of this study is to investigate the phytochemical composition and the biological activities (in vitro) of its extracts. The plant was extracted by cold maceration with four solvents presenting an increasing polarity: cyclohexane (CHX), dichloromethane (DCM), ethyl acetate (EtOAc) and methanol (MeOH). The extracts were screened for their chemical composition by a HPLC-DAD detector for phenolic compounds identification and quantification and by GC-MS for volatile compounds detection. The antioxidant capacity (DPPH inhibition) was tested. Biological activities, mainly anti-Alzheimer activity (acetylcholinesterase inhibition), the antiproliferation of two human colon cancer cell lines (HCT-116 and Caco-2 cells) and antibacterial activity, were evaluated. Ten aromatic compounds were quantified by HPLC-DAD analysis. A total of 123 compounds were detected by GC-MS analysis. The MeOH extract showed a very interesting antioxidant activity with an inhibition percentage (IP) of 76.1% and an IC50 of 19.4 µg/mL. The EtOAc extract exhibited the strongest inhibition against the acetylcholinesterase activity (IP = 60.6%) at 50 µg/mL. It also strongly inhibited the proliferation of the HCT-116 cells (IP = 87.5%), whereas the DCM extract gave the best result with the Caco-2 cells (IP = 72.3%). The best antibacterial activity was obtained with the MeOH extract against Staphylococcus aureus (MIC = 1.2 µg/mL) and with the EtOAc extract against Escherichia coli (MIC = 2.4 µg/mL). This study highlights the chemical composition and therapeutic potential of S. fruticosa. It is important to mention that the following chemical compounds were identified for the first time in plant extracts: 2,6,11,15-tetramethyl-hexadeca-2,6,8,10,14-pentaene; 4,5,6,7-tetrahydroxy-1,8,8,9-tetramethyl-8,9-dihydrophenaleno [1,2-b]furan-3-one; podocarpa-1,8,11,13-tetraen-3-one,14-isopropyl-1,13-dimethoxy; podocarpa-8,11,13-trien-3-one,12-hydroxy-13-isopropyl-,acetate; 3',8,8'-trimethoxy-3-piperidin-1-yl-2,2'-binaphthyl-1,1',4,4'-tetrone; and 2,3-dehydroferruginol, thus underlining the originality of this study.
Assuntos
Antioxidantes , Salvia , Humanos , Antioxidantes/farmacologia , Antioxidantes/química , Acetilcolinesterase , Células CACO-2 , Antibacterianos/farmacologia , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Compostos Fitoquímicos/farmacologiaRESUMO
A highly α-regioselective N-nucleophilic allylic substitution of cyclic MBH alcohols and acetates with imidazole or benzimidazole, in toluene at reflux with an azeotropic distillation, was successfully carried out with no catalysts or additives, affording the corresponding N-substituted imidazole derivatives in good yields. On the other hand, in refluxing toluene or methanol, the aza-Michael addition of imidazole onto acyclic MBH alcohols was performed using DABCO as an additive, leading to the corresponding 1,4-adducts in 70-84% yields.
RESUMO
This study aimed to evaluate the effect of various heating temperatures on the antioxidant activities of camel milk caseins. The samples were processed with three different heat treatments: Pasteurization at low and high temperatures and boiling. Fresh camel milk (unheated) was used as a control. Camel milk caseins were separated by fast ion exchange liquid chromatography (FPLC) and identified by the sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS page). The antioxidant activities of caseins were measu- red by three different in vitro methods: 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, 2, 2'-azino-bis (3-ethylbenzthiazoline-6-sulfonate) (ABTS) radical scavenging activity and ferric reducing power assay (FRAP). The antioxidant activity evaluated by the DPPH assay decreased significantly (p<0.05) with the increase in heat treatment of caseins. However, there was no significant difference in ABTS radical scavenging activity and Ferric Reducing Antioxidant Power assay (FRAP) of heat-treated camel caseins compared to unheated onesStill, a decrease was observed in those activities by the increase of temperature in the different casein concentrations. Besides, whatever the concentration tested and the methods applied, the antioxidant activity of beta-casein (ß-CN) was more pronounced than the alpha-casein (α-CN). Therefore, camel milk casein could be used as a natural source of antioxidants which may have a potential application in the food and nutraceutical industries. Throughout the different heat treatments applied, pasteurization at low temperature could be the most suitable alternative to preserve the antioxidant properties of camel milk.
Assuntos
Caseínas , Leite , Animais , Antioxidantes/química , Camelus , Temperatura AltaRESUMO
This work was undertaken to determine the structural characteristics of polysaccharides extracted from CO2-enriched Arthrospiraplatensis (Spirulina Water Soluble Polysaccharide: SWSP), as well as its antioxidant activities, cytotoxic effects and laser burn wound healing in rats. This SWSP was structurally characterized by Scanning Electron Microscopy (SEM), Fourier-transformed infrared (FT-IR), X-ray diffraction (XRD), high-performance liquid chromatography (HPLC), and thin layer chromatography (TLC). This novel polysaccharide was found to have an average molecular weight of 6.21 kDa. It is a hetero-polysaccharide composed of rhamnose, xylose, glucose and mannose. According to XRD and FT-IR spectra, the SWSP showed a semi-crystalline structure. It is composed of 100 to 500 µm geometric shaped units with flat surfaces and it was found to inhibit the proliferation of human colon (HCT-116) and breast (MCF-7) cancers. This polysaccharide display potential antioxidant activities determined through three different assays: scavenging activity against 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulphonic acid (ABTS), 2,2-Diphenyl-1-Picrylhydrazyl (DPPH) scavenging assay and ferric reducing antioxidant power assay (FRAP). Results strongly support the beneficial effects of the SWSP to accelerate wound healing in rats. Indeed, its application significantly increased tissue re-epithelization and remodeling phases, after 8 days of the experiment. Findings herein demonstrated that SWSP could be a novel auspicious source of natural wound healing closure and/or cytotoxic remedy.
Assuntos
Antioxidantes , Spirulina , Ratos , Humanos , Animais , Antioxidantes/química , Dióxido de Carbono , Espectroscopia de Infravermelho com Transformada de Fourier , Polissacarídeos/química , Cicatrização , LasersRESUMO
Traditionally, Brassica species are widely used in traditional medicine, human food, and animal feed. Recently, special attention has been dedicated to Brassica seeds as source of health-promoting phytochemicals. This review provides a summary of recent research on the Brassica seed phytochemistry, bioactivity, dietary importance, and toxicity by screening the major online scientific database sources and papers published in recent decades by Elsevier, Springer, and John Wiley. The search was conducted covering the period from January 1964 to July 2022. Phytochemically, polyphenols, glucosinolates, and their degradation products were the predominant secondary metabolites in seeds. Different extracts and their purified constituents from seeds of Brassica species have been found to possess a wide range of biological properties including antioxidant, anticancer, antimicrobial, anti-inflammatory, antidiabetic, and neuroprotective activities. These valuable functional properties of Brassica seeds are related to their richness in active compounds responsible for the prevention and treatment of various chronic diseases such as obesity, diabetes, cancer, and COVID-19. Currently, the potential properties of Brassica seeds and their components are the main focus of research, but their toxicity and health risks must also be accounted for.
Assuntos
Anti-Infecciosos , Brassica , COVID-19 , Animais , Anti-Inflamatórios/farmacologia , Antioxidantes/farmacologia , Brassica/química , Etnofarmacologia , Glucosinolatos , Humanos , Hipoglicemiantes/farmacologia , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Fitoterapia , Extratos Vegetais/química , SementesRESUMO
Vitis vinifera (V. vinifera) is a herbaceous plant, cultivated worldwide and known for its biological benefits. The aim of this study is the investigation of the chemical composition as well as the determination of the biological potential of different grape stem extracts obtained by maceration and accelerated solvent extraction (ASE). The HPLC analysis of the tested extracts led to the identification of 28 compounds of which 17 were identified for the first time in grape plants, in addition to seven revealed in the stem part for the first time. Twenty-nine volatile molecules have been detected by GC-MS in the grape stem part; among them seven were identified for the first time in the grape plant. For the biological analysis, the ethyl acetate extract (EtOAc) obtained by maceration showed a significant potential regarding antioxidant activity (IC50 = 42.5 µg/mL), anti-Alzheimer (IC50 = 14.1 µg/mL), antidiabetic (IC50 = 13.4 µg/mL), cytotoxic with HCT-116 (IC50 = 12.5 µg/mL), and anti-inflammatory (IC50 = 26.6 µg/mL) activities, as well as showing the highest polyphenol content (207.9 mg GAE/g DW).
Assuntos
Vitis , Anti-Inflamatórios/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Polifenóis/análise , Polifenóis/farmacologia , Vitis/químicaRESUMO
Pure compounds belonging to phenolic family were studied for their biological potential such as 5,8-dihydroxy-1,4-naphthoquinone (M1), rutin hydrate (M2), 2,3-dichloro-5,8-dihydroxy-1,4-naphthoquinone (M3), taxifolin (M4), myricetin (M5), plumbagin (M6), silibinin (M7), dihydromyricetin (M8), shikonin (M9), quercetin 3-ß-D-glucoside (M10), (±)-taxifolin hydrate (M11), cardamonin (M12),(-)-epicatechin (M13), 9-chloro-10-hydroxy-anthracene-1,4-dione (M14), 9-chloro-10-hydroxy-2,3-dimethyl-anthracene-1,4-dione (M15), 2-chloro-3-(2-hydroxy-5-methylanilino)-1,4-naphthoquinone (M16), 2-chloro-3-(4-hydroxy-phenylamino)-(1,4) naphthoquinone (M17), 2-chloro-3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-(1,4)-naphtoquinone (M18), and myricitrin dihydrate (M19). These molecules were chosen based on two reasons; the limited or total absence of their exploitation in several studied activities and the use of other tests for the same activity. The evaluation of the in vitro anti-acetyl-cholinesterase (AChE), anti-5-lipoxygenase (5-LOX), anti-xanthine oxidase (XOD), anti-alpha glucosidase, anti-superoxide dismutase (SOD), anti-oxidant (DPPH (1, 1-diphenyl-2-picrylhydrazyl) and ABTS (2, 2- azinobis-3-ethylbenzothiazoline-6-sulphonate)), and anticancer activities of mentioned 19 molecules was explored during this work. M3, M14, M15, M16, M17, M18, M19 were exploited for the first time for such purposes. Tested compounds were shown to have interesting radical scavenging abilities against DPPH radicals, and the highest molecules among them were M19 and M5 (IC50 = 12.0 and 15.5 µM, respectively), and M4, M19 and M2 against ABTS (IC50= 1.9, 4.3 and 4.3 µM, respectively). Moreover, the majority of products showed very important cytotoxic activity since IC50 values were ranging between (IC50= 0.2 µM (M1) and 79 µM (M8)) against HCT116 cell line, and values of IC50= 0.2 µM for M1 against MCF7 cell line. All new molecules (non studied before) were shown to have great cytotoxic effect against both cancer cell lines.Furthermore, molecule M5 was shown to have anti-inflammatory potential via the inhibition of 5-LOX enzyme (65% at 100 µM). In addition, M19 showed important anti XOD activity with 47% of inhibition at 100 µM. Also, it has been found that compound M3 had the best anti alpha glucosidase activity with 43.8 % of inhibition at 100 µM, the highest anti-AChE effect (IC50= 14.5 µM), and the best effect towards SOD (IC50= 10.0 µM). A structure-activity relationship study was also performed.
Assuntos
Anti-Inflamatórios/farmacologia , Antioxidantes/farmacologia , Inibidores da Colinesterase/farmacologia , Flavonoides/farmacologia , Inibidores de Glicosídeo Hidrolases/farmacologia , Superóxido Dismutase/antagonistas & inibidores , Xantina Oxidase/antagonistas & inibidores , Anti-Inflamatórios/química , Antineoplásicos/farmacologia , Antioxidantes/química , Morte Celular/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Flavonoides/química , Células HCT116 , Humanos , Células MCF-7 , Superóxido Dismutase/metabolismo , Xantina Oxidase/metabolismo , alfa-Glucosidases/metabolismoRESUMO
Alzheimer's disease is characterized by amyloid ß aggregation and cholinergic neurodegeneration. In the present study, pure DDN (2,3-dichloro-5,8-dihydroxy-1,4-naphthoquinone) was examined, for the first time, for its dual potential as inhibitor of acetylcholinesterase (AChE) and Aß42 aggregation. Such investigation was encouraged by the in vitro high antioxidant potential of DDN. Indeed, it revealed interesting antioxidant activity with IC50 values of 9.8 and 4.3 µM for ABTS and reducing power, respectively. The ability of DDN to counteract Aß42 aggregation was evaluated by thioflavine-T assay. Strong inhibition of Aß42 aggregation of more than 90% at 25 µM was measured. Moreover, results showed that DDN inhibited AChE (IC50 = 14.5 µM). To better understand the interactions between DDN and AChE, molecular docking was performed. Obtained data predicted a high interaction characterized by hydrogen bonding at TYR337 as for galanthamine (positive control). Several residues involved in AChE hydrophobic interactions were similarly implicated in binding of this domain to DDN (ASP74, THR83, and TYR124). All these data would be useless if DDN could not pass the blood-brain barrier. So, DDN was loaded into alginate microspheres to enhance its stability and bioavailability. Thereafter, drug release profiles were assessed using immersion cell apparatus.
Assuntos
Acetilcolinesterase/química , Doença de Alzheimer/tratamento farmacológico , Peptídeos beta-Amiloides/química , Inibidores da Colinesterase/química , Naftoquinonas/química , Fragmentos de Peptídeos/química , Agregados Proteicos/efeitos dos fármacos , Inibidores da Colinesterase/uso terapêutico , Proteínas Ligadas por GPI/química , Humanos , Naftoquinonas/uso terapêuticoRESUMO
A new series of 3-hydroxyflavones (1-46) were synthesized according to the Claisen-Schmidt followed by Algar-Flynn-Oyamada reactions (AFO) in one step. The synthesized flavonoids were characterized by 1H NMR, 13C NMR and DCI-HRMS. All the synthesized compounds were tested in vitro for their 15-lipoxygenase inhibitory and cytotoxic activity against the human cell lines HCT-116 (Human colon carcinoma), IGROV-1 and OVCAR-3 (human ovarian carcinoma). It has been found that the derivatives 25, 37 and 45 were the most actives against HCT-116 (IC50â¯=â¯8.0, 9.0 and 9.0⯵M, respectively) and against IGROV-1 (IC50â¯=â¯2.4, 5.0 and 6.0⯵M, respectively). The derivatives 14 and 21 exhibited the higher anti-inflammatory activity at 100⯵M with PI values of 76.50 and 72.70%, respectively. Molecule description was performed with DFT calculations, the drug likeness and bioactivity scores. The results exhibted that some compounds are in linear correlation with Lipinski's rule of five showing good drug likeness and bioactivity score for drug targets.
Assuntos
Anti-Inflamatórios não Esteroides/farmacologia , Antineoplásicos/farmacologia , Araquidonato 15-Lipoxigenase/metabolismo , Flavonoides/farmacologia , Inibidores de Lipoxigenase/farmacologia , Anti-Inflamatórios não Esteroides/síntese química , Anti-Inflamatórios não Esteroides/química , Antineoplásicos/síntese química , Antineoplásicos/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Teoria da Densidade Funcional , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Flavonoides/síntese química , Flavonoides/química , Células HCT116 , Humanos , Inibidores de Lipoxigenase/síntese química , Inibidores de Lipoxigenase/química , Estrutura Molecular , Relação Estrutura-AtividadeRESUMO
BACKGROUND: The growing demand for natural food preservatives in the last decade has promoted investigations on their application for preserving perishable foods. In this context, the present review is focused on discussing the prospective application of plant extracts containing phenolics or isolated plant phenolics as natural antimicrobials in foods. Plant essential oils are outside the scope of this review since utilization of their antimicrobial activity for food preservation has been extensively reviewed. RESULTS: Although the exact antimicrobial mechanisms of action of phenolic compounds are not yet fully understood, it is commonly acknowledged that they have diverse sites of action at the cellular level. Antimicrobial phenolics can be added directly to the formulation of perishable food products or incorporated into food-contact materials to release them in the immediate zone of perishable foods. Edible coatings or active food packaging materials can thus be used as carriers of plant bioactive compounds. CONCLUSION: These materials could be an interesting delivery system to improve the stability of phenolics in foods and to improve the shelf life of perishable foods. This review will thus provide an overview of current knowledge of the antimicrobial activity of phenolic-rich plant extracts and of the promises and limits of their exploitation for the preservation of perishable foods. © 2018 Society of Chemical Industry.
Assuntos
Anti-Infecciosos/farmacologia , Conservantes de Alimentos/química , Extratos Vegetais/química , Plantas/química , Polifenóis/química , Anti-Infecciosos/química , Microbiologia de Alimentos , Embalagem de Alimentos/instrumentação , Conservantes de Alimentos/farmacologia , Extratos Vegetais/farmacologia , Polifenóis/farmacologiaRESUMO
The phytochemical study of Achillea cretica growing in Tunisia led to the isolation of two novel sesquiterpene lactones, which have been designated achicretin 1 and achicretin 2. Their chemical structures were further confirmed by mass spectroscopy (ESI-MS) and by extensive application of one- and two-dimensional NMR spectroscopy. The isolated compounds were tested for their cytotoxic activity against four human cancer cell lines, IGROV-1, OVCAR-3, MCF-7, and HCT-116 using the MTT assay. It has been found that achicretin 2 exhibited more potent inhibitory activity with IC50 = values of 14.0 ± 1.0 and 16.0 ± 2.0 µM against OVCAR-3 and HCT-116 cells, respectively.
Assuntos
Achillea/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Lactonas/isolamento & purificação , Lactonas/farmacologia , Sesquiterpenos de Guaiano/isolamento & purificação , Sesquiterpenos de Guaiano/farmacologia , Antineoplásicos Fitogênicos/química , Ensaios de Seleção de Medicamentos Antitumorais , Células HCT116 , Humanos , Lactonas/química , Estrutura Molecular , Sesquiterpenos de Guaiano/química , TunísiaRESUMO
Four flavones were isolated from dried leaves of Artemisia campestris L. 2',4',5,7-tetrahydroxy-5',6-dimethoxyflavone, eupatilin and dimethoxycentaureidin were reported for the first time in this species whereas cirsiliol was previously identified but it was isolated for the first time. Their structures were elucidated by spectroscopic methods, including 1D and 2D NMR experiments and mass spectrometry analysis. In addition, all isolated flavones were evaluated for their antioxidant, anti-inflammatory, anti-superoxide dismutase, anti-xanthine oxidase and cytotoxic activities. The results showed that all isolated compounds exhibited potent anti-xanthine oxidase activity with IC50 ranging from 3.3 to 6.8 µM, which was higher than that of the control compound allopurinol (8.2 ± 0.6 µM). In addition, cirsiliol was found to be the most cytotoxic against OVCAR-3, IGROV-1and HCT-116 cell lines at 15µM, with inhibition percentage values of 53.7, 48.8 and 40.9%, respectively. All compounds also showed weak to moderate anti-inflammatory and anti-superoxide dismutase activities.
Assuntos
Artemisia/química , Flavonas/química , Flavonas/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Folhas de Planta/química , Ativação Enzimática , Espectroscopia de Ressonância Magnética , Superóxido Dismutase/metabolismo , Xantina Oxidase/metabolismoRESUMO
Essential oil of the seeds from the endemic Tunisian plant Ferula tunetana Pomel ex Batt. was analyzed for its chemical composition and screened for its antimicrobial, antioxidant and antigerminative properties. The chemical composition of the isolated oil is reported for the first time. According to the GC/FID, GC/MS and 13 C-NMR analysis results; 18 compounds were identified accounting for 84.6% of the total oil. The chemical composition of this essential oil was characterized by the presence of a high proportion of monoterpene hydrocarbons (77.3%) followed by oxygenated sesquiterpenes (4.1%) and sesquiterpene hydrocarbons (3.2%). α-Pinene (39.8%), ß-pinene (11.5%) and (Z)-ß-ocimene (7.5%) were the predominant compounds. Moreover, the isolated oil was tested for its antimicrobial activity using the disc-diffusion and the microdilution assays against six Gram-positive and five Gram-negative bacteria as well as towards two Candida species. The isolated oil was tested also for its antioxidant activity against DPPH, ABTS, O2â and hydrogen peroxide (H2 O2 ), and for its antigerminative potential. It was found that it exhibited interesting antimicrobial activity against Salmonella typhimurium LT2 DT104 (inhibition zone (IZ) 16.2 ± 1.0 mm) and Bacillus cereus ATCC 14579 (IZ 15.8 ± 1.0 mm). However, it exerted a moderate antioxidant activity against H2 O2 (IC50 78.2 ± 2.98 µg/ml) and towards O2â (IC50 89.2 ± 3.82 µg/ml). The antigerminative effect of this oil was also evaluated in this work. Results showed a toxic effect.