scholarly journals Synthesis, antioxidant and cytoprotective activity evaluation of C-3 substituted indole derivatives

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Beata Jasiewicz ◽  
Weronika Kozanecka-Okupnik ◽  
Michał Przygodzki ◽  
Beata Warżajtis ◽  
Urszula Rychlewska ◽  
...  

AbstractA series of fifteen indole derivatives substituted at the C-3 position were synthesized and characterized. The antioxidant activity of all derivatives was investigated by three in vitro antioxidant assays, and the derivative with pyrrolidinedithiocarbamate moiety was the most active as a radical scavenger and Fe3+-Fe2+ reducer. It can be stated that possible hydrogen and electron transfer mechanism is suggested for the quenching of the free radical. Moreover, the indolyl radical stabilization and the presence of unsubstituted indole nitrogen atom are mandatory for the observed antioxidant activity, which strongly depends on the type of the substituent directly connected to the methylene group at the C-3 position. Human red blood cells (RBC) have been used as a cell model to study derivatives interaction with the cell membrane. Haemolytic activity and RBC shape transformation were observed for certain derivatives in a concentration-dependent manner. However, most of the derivatives at sublytic concentration showed high cytoprotective activity against oxidative haemolysis induced by 2,2′-azobis(2-methylpropionamidine) dihydrochloride (AAPH). The cytoprotective properties of derivatives can be explained mostly due to their interactions with the RBC membrane components. Taking together, theoretical estimations and experimental data confirm the beneficial interactions between the selected C-3 substituted indole derivatives and the RBC membrane under oxidative stress conditions. These results encourage us to further structural optimization of C-3 substituted indole derivatives as potent antioxidant compounds.

2008 ◽  
Vol 5 (s2) ◽  
pp. 1123-1132 ◽  
Author(s):  
H. Vijay Kumar ◽  
C. R. Gnanendra ◽  
Nagaraja Naik ◽  
D. Channe Gowda

Dibenz[b,f]azepine and its five derivatives bearing different functional groups were synthesized by known methods. The compounds thus synthesized were evaluated for antioxidant potential through different in vitro models such as (DPPH) free radical scavenging activity,ß-carotene-linoleic acid model system, reducing power assay and phosphomolybdenum method. Under our experimental condition among the synthesized compounds dibenz[b,f]azepine (a) and 10-methoxy-5H-dibenz[b,f]azepine (d) exhibited potent antioxidant activity in concentration dependent manner in all the above four methods. Butylated hydroxyl anisole (BHA) and ascorbic acid (AA) were used as the reference antioxidant compounds. The most active compounds like dibenz[b,f]azepine and its methoxy group substituent have shown more promising antioxidant and radical scavengers compared to the standards like BHA and ascorbic acid. It is conceivable from the studies that the tricyclic amines,i.e. dibenz[b, f]azepine and some of its derivatives are effective in their antioxidant activity properties.


Author(s):  
Bajaree Jantrapanukorn ◽  
Pannapa Powthong ◽  
Chitradee Luprasong

Objectives: The objectives of this study were to investigate the in vitro biological effect of the methanolic crude extract received from edible mushrooms; Flammulina velutipes on anti-inflammatory, antioxidant activity, anti-lipid peroxidation (LPO), antimicrobial activity, and anticancer activity. The scientific result obtained here was possibility of developing this variety as an ingredient in health/medical food purposes as well as a functional food.Methods: In this study, the methanol crude extract of F. velutipes has been performed and in vitro pharmacological properties such as anti-inflammatory, antioxidant activity, anti-LPO, antimicrobial activity, and anticancer activity were evaluated.Results: The results revealed that anti-inflammatory activity of crude extract was very significant with 79.81±0.87% of the dose-dependent manner. Antioxidant and anti-low-density lipoprotein (LDL) peroxidation activity of the extract showed its capacity of free radical scavenging with high-level antioxidant compounds and lipid preventive effects (2, 2-diphenyl-1-picrylhydrazyl: 79.81±0.01%, total phenol: 991.10±0.01 μg gallic acid equivalents/0.1 g dry matter, H2O2: 93.27±0.05%, LPO: 33.33±0.00%, and LDL: 57±0.03%, respectively). Analysis has also demonstrated that the methanolic extract of F. velutipes provided an antimicrobial activity to ESBL-producing Klebsiella pneumoniae. Moreover, F. velutipes extract showed a growth inhibitory effect in HepG2 cells with the 50% inhibitory concentration (IC50) value IC50=8.25±7.59 μg/ml.Conclusion: This indicated that crude extract from F. velutipes was scientifically proved as a potential source of therapeutic agent and be able to utilize as a functional ingredient for healthy or supplement food.


1996 ◽  
Vol 317 (3) ◽  
pp. 747-754 ◽  
Author(s):  
S. V. RUDENKO ◽  
E. E. NIPOT

The ability of the peptides melittin, [Ala-14]melittin (P14A) and whole bee venom to lyse red blood cells (RBC) and to cause shape transformation, binding, partitioning and changes in volume of the cells during haemolysis, as well as the action of the bivalent cations Zn2+ and Ca2+, chlorpromazine, albumin and plasma on the peptide-induced haemolysis of RBC in high ionic-strength solution, have been investigated. The protective effect of all inhibitors depends on whether they have been added to the media before or after the cells. When added before the cells they reduced significantly the rate of peptide-induced haemolysis and shape transformation. The effect was maximal when agents acted simultaneously after introduction of the cells into the media containing both inhibitors and peptides. Incubation of the cells in isotonic solution before the addition of peptides enhanced 2–3-fold the RBC susceptibility (i.e. rate of haemolysis) to lytic action of the same amount of peptides, and increased the order of the haemolytic reaction, although the power law coefficient did not exceed a value of 2 for all peptides, suggesting that haemolysis is attributable to the monomeric or dimeric forms of the peptides. Partition coefficients were of the order of ∼106 M-1, and P14A possessed a value 3-fold larger compared with melittin and bee venom, which correlated with its enhanced haemolytic activity. The protective action of inhibitors against peptide-induced haemolysis has been explained on the basis of their ability to compete with peptide binding at an early stage of peptide–membrane interaction, and not as a result of inhibition of a pre-existing peptide-induced pore. Whereas melittin increased the volume of RBC during haemolysis, P14A, melittin in the presence of phospholipase A2 or bee venom, reduced the volume in a concentration-dependent manner. The present data reveal the significant role of the initial stage of peptide–membrane interaction and peptide structure in the mechanism of haemolysis. These data are not consistent with a lipid-based mechanism of peptide-induced haemolysis, indicating that the mode of peptide–protein interaction is an important and decisive step in the haemolytic mechanism. It should be noted that data (in the form of three additional Tables) on the ability of inhibitors to protect cells from haemolysis when inhibitor and peptide act simultaneously are available. They are reported in Supplementary Publication SUP 50178, which has been deposited at the British Library Document Supply Centre, Boston Spa, Wetherby, West Yorkshire LS23 7BQ, U.K., from whom copies can be obtained on the terms indicated in Biochem. J. (1996) 313, 9.


Author(s):  
Hadi Shariati ◽  
Mohammad Hassanpour ◽  
Gholamreza Sharifzadeh ◽  
Asghar Zarban ◽  
Saeed Samarghandian ◽  
...  

Objective: The present study has been carried out to evaluate the diuretic and antioxidant properties of pine herb in an animal model. Materials and Methods: 45 adult male rats were randomly divided into nine groups including: groups I (the negative control), groups II (positive control, furosemide 10 mg/kg), groups III to VIII (treatment groups received 100, 200, 400 mg/kg of the aqueous extracts of bark and fruit) and group IX received the combination of aqueous extract of bark (100 mg/kg) and the fruit (100 mg/kg). The urine output, glomerular filtration rate (GFR), electrolytes, urea, and creatinine levels were evaluated . Furthermore, the phenolic content and antioxidant activity of both extracts were also assessed using 2, 2-diphenyl-1-picrylhydrazyl (DPPH), ferric reducing antioxidant power (FRAP) and Folin–Ciocalteu methods. Results: The aqueous extracts of the pine bark and fruit increased the urinary output in a dose-dependent manner. The combination of the two extracts compared to the other extracts alone significantly increased the serum potassium level. This study also showed each extract increase creatinine clearance in a dose-dependent manner (p<0.01 and p<0.05). The increase of GFR in the combination group was not significant. The current data showed a significant increase in the total phenolic content in pine bark extract in compared with the fruit extract. Conclusion: The pine bark and fruit can be useful in the prevention and treatment of kidney stones due to the high antioxidant activity.


Agronomy ◽  
2021 ◽  
Vol 11 (3) ◽  
pp. 417
Author(s):  
Ioana Otilia Ghinea ◽  
Maria Daniela Ionica Mihaila ◽  
Giorgiana-Valentina Blaga (Costea) ◽  
Sorin Marius Avramescu ◽  
Mihaela Cudalbeanu ◽  
...  

The purpose of this study was to assess the suitability of the Romanian Albanus hybrid of Sorghum bicolor as a potential functional food ingredient. Ultrasound-assisted extraction in different solvents, together with spectrophotometric and chromatographic methods, was used to monitor the variation in total phenolic and flavonoid content and the antioxidant activity of raw sorghum grains before and during short germination periods (24, 36 and 48 h). The High-Performance Liquid Chromatography with Diode-Array Detection (HPLC-DAD) investigation of the extracts revealed that the ungerminated sorghum grains extracted with methanol had the highest diversity of phenolic compounds, while the total phenolic content (TPC) was the highest after 36 h of germination in both extract types: 1853 mg GAE/100 g for the methanolic extract and 1726 mg GAE/100 g for the ethanolic extract. The findings of this study showed that the TPC of sorghum extracts is strongly correlated with their antioxidant activity and, overall, that the studied extracts presented a good radical scavenger activity, which supports the benefits of alimentary uses of Sorghum bicolor grains.


Author(s):  
Tomasz Piechowiak ◽  
Bartosz Skóra ◽  
Katarzyna Grzelak-Błaszczyk ◽  
Michał Sójka

AbstractThe purpose of this study was to investigate the biological properties of an extract obtained from the waste of blueberry fruit. The study covered the optimization of extraction of antioxidants from blueberry pomace and the determination of antioxidant properties of the extract using HaCaT as the model organism. Research showed that the yield of antioxidants extraction from blueberry waste was dependent on the applied extraction conditions. Based on the mathematical models, the optimal conditions of extraction process in which the maximum quantity of antioxidant compounds is achieved from the waste mass unit, i.e., the relation of the waste mass to the volume of ethanol equal to 1:17.36, and process time equal to 1000 s. The obtained extract was characterized by high antioxidant activity, which was shaped by high content of polyphenols, mainly anthocyanins. Moreover, the extract showed a high ability to protect HaCaT cells from the occurrence of oxidative stress induced by H2O2. Cells treated with the extract and H2O2 generated a lower amount of ROS than cells treated with H2O2 only. The obtained results will be base of further studies on applying the extract in production of diet supplements and functional foods with increased antioxidant activity. Moreover, the main research material is blueberry pomace which is a troublesome waste material for juice producers. Consequently, according to a sustainable development idea, the study results will provide an opportunity to increase interest in the problem of rational use of the waste material to a certain extent.


Antioxidants ◽  
2021 ◽  
Vol 10 (2) ◽  
pp. 165
Author(s):  
Elisabetta Bravi ◽  
Giovanni De Francesco ◽  
Valeria Sileoni ◽  
Giuseppe Perretti ◽  
Fernanda Galgano ◽  
...  

The brewing industry produces high quantities of solid and liquid waste, causing disposal issues. Brewing spent grains (BSGs) and brewing spent hop (BSH) are important by-products of the brewing industry and possess a high-value chemical composition. In this study, BSG and BSH, obtained from the production process of two different types of ale beer (Imperial red and Belgian strong beer) were characterized in terms of valuable components, including proteins, carbohydrates, fat, dietary fiber, β-glucans, arabinoxylans, polyphenols, and phenolic acids, and antioxidant activity (Ferric Reducing Antioxidant Power Assay (FRAP), 2,2-Diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-Azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS)). Significant concentrations of total polyphenols were observed in both BSH and BSG samples (average of about 10 mg GAE/g of dry mass); however, about 1.5-fold higher levels were detected in by-products of Belgian strong ale beer compared with Imperial red. Free and bound phenolic acids were quantified using a validated chromatographic method. A much higher level of total phenolic acids (TPA) (about 16-fold higher) was found in BSG samples compared with BSHs. Finally, their antioxidant potential was verified. By-products of Belgian strong ale beer, both BSG and BSH, showed significantly higher antioxidative capacity (about 1.5-fold lower inhibitory concentration (IC50) values) compared with spent grains and hop from the brewing of Imperial red ale. In summary, BSG and BSH may be considered rich sources of protein, carbohydrates, fiber, and antioxidant compounds (polyphenols), and have the potential to be upcycled by transformation into value-added products.


Plants ◽  
2021 ◽  
Vol 10 (2) ◽  
pp. 212
Author(s):  
Yeimi Cecilia Vega-Ruiz ◽  
Corina Hayano-Kanashiro ◽  
Nohemí Gámez-Meza ◽  
Luis Angel Medina-Juárez

Jatropha species have been shown to be an important source of secondary metabolites with different biological effects. Jatropha cinerea (Ortega) Müll. Arg and Jatropha cordata (Ortega) Müll. Arg are distributed in the Northwestern region of Mexico, are adapted to extreme weather conditions and are widely used (stems, leaves, and sap) in traditional medicine. The aim of the present study was to carry out the phytochemical characterization and the evaluation of the antioxidant activity in methanolic extracts of stems and leaves from J. cinerea and J. cordata. The compounds present in the extracts of both species were characterized by ESI-IT-MS/MS and quantified by HPLC-DAD. The results showed that the stem extracts of both species are rich in phenolic acids, while the leaf extracts are rich in flavonoids. Some of the main compounds found were gallic acid, gentisic acid, 3,4-Dihydroxybenzoic acid, vitexin, isovitexin, and catechol. Both species showed high concentrations of phenols and total flavonoids and antioxidant activity. J. cordata showed the highest antioxidant capacity and the highest concentration of phenolic compounds. Overall, both Jatropha species are a natural source of antioxidant compounds with potential biotechnological uses.


2013 ◽  
Vol 41 (1) ◽  
pp. 136 ◽  
Author(s):  
Violeta NOUR ◽  
Ion TRANDAFIR ◽  
Mira E. IONICA

Ten indeterminate tomato cultivars differing in fruit shape and typology, grown simultaneously in a greenhouse from Oltenia (Southwestern Romania) and harvested at red ripe stage, were investigated for the contents in ascorbic acid, lycopene, β-carotene, total phenolics, minerals (K, Na, Ca and Mg) and trace elements (Fe, Cu, Mn, Cr, Zn and B). In addition, their antioxidant activities were determined. Significant differences were found among tomato cultivars in all studied antioxidant compounds, as well as in the antioxidant activity. Ascorbic acid ranged from 91.9 to 329.7 mg kg-1 fw, lycopene ranged from 19.7 to 49.0 mg kg-1 fw, while total phenolic compounds varied between 300.2 and 557.8 mg kg-1 fw. Antioxidant activity ranged from 0.81 mmol Trolox kg-1 fw to 1.74 mmol Trolox kg-1 fw and it was significantly correlated to total phenolics content (r = 0.91; p< 0.05). The cocktail type cultivar ‘Tiger’ and the cherry type cultivar ‘Belle’ proved to be the most powerful in antioxidant activity and phenolic compounds while the rectangular plum shaped cultivar ‘Porto’ recorded the highest average lycopene content. A valuable cultivar proved to be the brownish red ‘Sacher’ which registered among the highest contents of phenolics, lycopene and ascorbic acid. Mineral and trace elements contents were also significantly affected by cultivars. Values recorded for K, Ca and Mg ranged from 2139.6 to 3056.9 mg kg-1, 137.7 to 325.8 mg kg-1 and 27.3 to 168.7 mg kg-1 respectively.


Marine Drugs ◽  
2021 ◽  
Vol 19 (10) ◽  
pp. 549
Author(s):  
Noémie Coulombier ◽  
Thierry Jauffrais ◽  
Nicolas Lebouvier

The demand for natural products isolated from microalgae has increased over the last decade and has drawn the attention from the food, cosmetic and nutraceutical industries. Among these natural products, the demand for natural antioxidants as an alternative to synthetic antioxidants has increased. In addition, microalgae combine several advantages for the development of biotechnological applications: high biodiversity, photosynthetic yield, growth, productivity and a metabolic plasticity that can be orientated using culture conditions. Regarding the wide diversity of antioxidant compounds and mode of action combined with the diversity of reactive oxygen species (ROS), this review covers a brief presentation of antioxidant molecules with their role and mode of action, to summarize and evaluate common and recent assays used to assess antioxidant activity of microalgae. The aim is to improve our ability to choose the right assay to assess microalgae antioxidant activity regarding the antioxidant molecules studied.


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