scholarly journals Benzimidazolium Salts Bearing 2-methyl-1,4-benzodioxane Group: Synthesis, Characterization, Computational Studies, In vitro Antioxidant and Antimicrobial Activity

2021 ◽  
Vol 11 (5) ◽  
pp. 13333-13346

This study contains the synthesis of the 1-(2-methyl-1,4-benzodioxane)benzimidazole and 2-methyl-1,4-benzodioxane substituted benzimidazolium salts. The benzimidazolium salts were synthesized from the reaction of the 1-(2-methyl-1,4-benzodioxane)benzimidazole and various aryl chlorides. All compounds were characterized using 1H NMR, 13C NMR, FTIR spectroscopy, and elemental analysis techniques. The antioxidant properties of benzimidazolium salts were examined by 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging and hydrogen peroxide scavenging ability assays. The compounds showed a moderate inhibitory effect on DPPH radical (The percent inhibition = 29.53-39.75). Also, the compounds exhibited significant H2O2 radical scavenging activity. Antimicrobial activities of the compounds were examined against nine bacterial strains and Candida albicans. All compounds displayed marked antimicrobial activity against tested microorganisms, particularly against Pseudomonas aeruginosa, Listeria monocytogenes, and C. albicans. From the computational perspective, benzimidazolium salts were also optimized at B3LYP / DMol3// DFT level using the Discovery Studio 2020 program. HOMO–LUMO analysis and molecular electrostatic potential surface (MESP) were exerted to examine the effects of benzimidazolium salts' electronic and structural properties.

2017 ◽  
Vol 23 (4) ◽  
pp. 349-357 ◽  
Author(s):  
Szabolcs Molnár ◽  
Kata Mikuska ◽  
Katalin Patonay ◽  
Krisztina Sisa ◽  
Hussein G Daood ◽  
...  

The present paper reports about a comparative survey on the chemical composition, antioxidant activity and in vitro antimicrobial activity of selected propolis samples collected in Hungary. The total levels of polyphenolic compounds including flavonoids in ethanolic extracts of propolis were assessed. The major constituents of ethanolic extracts of propolis were analysed by gas chromatography/mass spectrometry analysis. Total phenolic content was determined spectrophotometrically using a Folin–Ciocalteu reagent. Free radical scavenging activities were evaluated by means of 2,2-diphenyl-1-picrylhydrazyl assay. In vitro inhibitory activity was investigated against eight different bacterial strains by agar well diffusion assay. An extensive comparison was carried out regarding general parameters and specific polyphenolic components. The experimental data led to the observation that there is considerable variability in terms of the quality and the biological value of the distinctive propolis samples. These findings confirm the hypothesis of the study; versatile experimental results are required for proper, well-reasoned, balanced and standardised industrial applications. The major flavonoid components were found to be chrysin and pinocembrin; however, versatile minor components were also detected. The total polyphenol content of ethanolic extracts of propolis ranged between 104.6 mg/g and 286.9 mg/g (gallic acid equivalent). The radical scavenging activity of ethanolic extracts of propolis varied between 101.7 mg/g and 286.9 mg/g (ascorbic acid equivalent). As the quality of propolis depends on the season, vegetation and the area of collection, marked differences were found among the different products examined in terms of both composition and general characteristics. The studied samples exhibited significant differences in term of antimicrobial activities.


2015 ◽  
Vol 2015 ◽  
pp. 1-11 ◽  
Author(s):  
Naif Abdullah Al-Dhabi ◽  
Mariadhas Valan Arasu ◽  
Thankappan Sarasam Rejiniemon

This study aimed to investigate thein vitroantibacterial, antifungal, antibiofilm, antioxidant, and anticancer properties of isosteviol isolated from endangered medicinal plantPittosporum tetraspermum. Pure compound was obtained and characterized by column chromatography followed by1H NMR,13C NMR, IR, and mass spectral analysis. The antimicrobial activities of the compound were assessed by the broth microdilution method and the antioxidant properties were determined using reducing ability assay, DPPH scavenging assay, hydroxyl radical scavenging activity, and superoxide radical scavenging assay. Anticancer study was evaluated by following MTT assay. Column purification and spectrocopical analysis lead to identifying isosteviol from the crude ethyl acetate extract. The compound exhibited significant activity against bacteria such asStaphylococcus epidermidis(125 µg/mL),Staphylococcus aureus(125 µg/mL), andKlebsiella pneumoniae(62.5 µg/mL). The MIC of the compound againstCandida albicans,Aspergillus niger, andTrichophyton mentagrophyteswas 62.5, 125, and 500 µg/mL, respectively. The compound showed comparatively better antibiofilm activity againstE. coli,S. typhi, andP. aeruginosa. Furthermore, it exhibited good antioxidant properties. Anticancer properties of the compound against Vero and MCF7 cell lines were its advantage. Novel isosteviol would be useful to reduce the infectious diseases caused by pathogenic microorganisms or slow the progress of various oxidative stress-related diseases.


2020 ◽  
Vol 16 ◽  
Author(s):  
Sajjad Esmaeili ◽  
Nazanin Ghobadi ◽  
Donya Nazari ◽  
Alireza Pourhossein ◽  
Hassan Rasouli ◽  
...  

Background: Curcumin, as the substantial constituent of the turmeric plant (Curcuma longa), plays a significant role in the prevention of various diseases, including diabetes. It possesses ideal structure features as enzyme inhibitor, including a flexible backbone, hydrophobic nature, and several available hydrogen bond (H-bond) donors and acceptors. Objective: The present study aimed at synthesizing several novel curcumin derivatives and further evaluation of these compounds for possible antioxidant and anti-diabetic properties along with inhibitory effect against two carbohydrate-hydrolyzing enzymes, α-amylase and α-glucosidase, as these enzymes are therapeutic targets for attenuation of postprandial hyperglycemia. Methods: Therefore, curcumin-based pyrido[2,3-d]pyrimidine derivatives were synthesized and identified using an instrumental technique like NMR spectroscopy and then screened for antioxidant and enzyme inhibitory potential. Total antioxidant activity, reducing power assay and 1,1-diphenyl-2-picrylhydrazyl (DPPH• ) radical scavenging activity were done to appraisal the antioxidant potential of these compounds in vitro. Results: Compounds L6-L9 showed higher antioxidant activity while L4, L9, L12 and especially L8 exhibited the best selectivity index (lowest α-amylase/α-glucosidase inhibition ratio). Conclusion: These antioxidant inhibitors may be potential anti-diabetic drugs, not only to reduce glycemic index but also to limit the activity of the major reactive oxygen species (ROS) producing pathways.


Antioxidants ◽  
2021 ◽  
Vol 10 (7) ◽  
pp. 1081
Author(s):  
Matilda Rădulescu ◽  
Călin Jianu ◽  
Alexandra Teodora Lukinich-Gruia ◽  
Marius Mioc ◽  
Alexandra Mioc ◽  
...  

The investigation aimed to study the in vitro and in silico antioxidant properties of Melissa officinalis subsp. officinalis essential oil (MOEO). The chemical composition of MOEO was determined using GC–MS analysis. Among 36 compounds identified in MOEO, the main were beta-cubebene (27.66%), beta-caryophyllene (27.41%), alpha-cadinene (4.72%), caryophyllene oxide (4.09%), and alpha-cadinol (4.07%), respectively. In vitro antioxidant properties of MOEO have been studied in 2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenging, and inhibition of β-carotene bleaching assays. The half-maximal inhibitory concentration (IC50) for the radical scavenging abilities of ABTS and DPPH were 1.225 ± 0.011 μg/mL and 14.015 ± 0.027 μg/mL, respectively, demonstrating good antioxidant activity. Moreover, MOEO exhibited a strong inhibitory effect (94.031 ± 0.082%) in the β-carotene bleaching assay by neutralizing hydroperoxides, responsible for the oxidation of highly unsaturated β-carotene. Furthermore, molecular docking showed that the MOEO components could exert an in vitro antioxidant activity through xanthine oxidoreductase inhibition. The most active structures are minor MOEO components (approximately 6%), among which the highest affinity for the target protein belongs to carvacrol.


2020 ◽  
Vol 21 (3) ◽  
Author(s):  
Magdalena Woźniak ◽  
Lucyna Mrówczyńska ◽  
Anna Sip ◽  
Marta Babicka ◽  
Tomasz Rogoziński ◽  
...  

Introduction. Honey, propolis and pollen belong to bee products that have beneficial biological properties. These products exhibit e.g. antibacterial, antifungal and antioxidant properties. Due to biological activity and natural origin, bee products are used, e.g. in the food industry, cosmetology and pharmacy. Aim. The aim of the study was to compare the antioxidant and antibacterial activity of honey, propolis and pollen from an apiary located in Wielkopolska Province. Material and methods. Honey, propolis and pollen used in this study came from the same apiary located in Wielkopolska Province. The antioxidant potential of bee products was evaluated applying DPPH· free radical scavenging activity assay. The antimicrobial activity of the tested bee products was determined by the point-diffusion method against 13 strains of pathogenic and potentially pathogenic bacteria. In addition, the total content of phenolic compounds in honey, propolis and pollen was determined by the colorimetric method. Results. Propolis exhibited higher antioxidant activity, in comparison to honey and pollen. The antiradical activity of propolis was equal to 80% approx. activity of Trolox, the standard antioxidant. Among tested bee products, propolis was characterized by the highest total phenols content. In addition, honey, propolis and pollen showed antagonistic activity against tested bacterial strains. Conclusions. The obtained results indicate that among the tested bee products of native origin, i.e. honey, propolis and pollen, propolis characterized by the highest antioxidant activity and the total content of phenolic compounds. In addition, all bee products showed bactericidal activity against the tested bacterial strains.


2021 ◽  
Vol 17 ◽  
Author(s):  
Brahim Asseli ◽  
Reguia Mahfoudi ◽  
Amar Djeridane ◽  
Mohamed Yousfi

Background: Research on medicinal plant antioxidants has emerged as a potential therapeutic to prevent free radical generated damage in the human body. Hammada elegans Botsch (popularly known as “Ajram”) is a xerophytic plant widely found in Laghouat region, but there are only a few reports about the biological or chemical properties of these species. Hence, the aim of this study is to investigate the antioxidant and the antihemolytic activities of hexanic, acetonic, methanolic and aqueous extracts of aerial parts of Algerian Hammada elegans Botsch by employing different in vitro assay systems. Methods: The total phenolic content, the flavonoid content and the condensed tannin amount were analyzed using Folin-Ciocalteu, aluminum chloride and vanillin assays, respectively. The in vitro antioxidant capacity of extracts was assessed by CUPRAC, iron chelating, ABTS•+and antihemolytic assays, and was expressed as EC50 values. Results: Among the analyzed extracts, the aqueous extract had the highest phenolic, flavonoid and tannin contents. Also, this extract displayed the highest antioxidant capacities compared to the other extracts and standards. Its EC50 value for ABTS radical-scavenging activity was 0.265 ± 0.003 mg/L. Moreover, this extract showed high iron (II) chelating ability (EC50 = 0.958 ± 0.001 mg/L), and good antioxidant activity in the cupric ion reducing activity (CUPRAC) in a concentration dependent manner (EC50 were 0.709 ± 0.002 mg/L). Additionally, this extract had the best antihemolytic activity against AAPH-induced hemolysis (EC50=0.090 ± 0.004 mg/L). Conclusion: Our study revealed that the aqueous extract of Hammada elegans Botsch, is a potential source of antioxidants which possess a high protective effect of membrane against free radical.


Author(s):  
Iserhienrhien Lucky Osafanme ◽  
Okolie Paulinus Ngozi

Aim: This study investigated the phytochemical constituents and in vitro antioxidant properties of methanol and aqueous leaf extracts of Geophila obvallata using standard methods. Materials and Methods: The in vitro antioxidant assays carried out were 1, 1‐diphenyl‐2‐picrylhydrazyl (DPPH) radical scavenging ability, Nitric oxide (NO•) radical scavenging activity assay, 2, 2'-azino-bis (3-ethylbenzthiazoline-6-sulphonic acid) (ABTS•+) radical cation scavenging assay, ferric reducing properties and hydroxyl radical scavenging assays. Results: Phytochemical analysis revealed the presence of alkaloids, flavonoids, phenolic compounds, steroids, saponins, terpernoids and cardiac glycosides in both extracts. Relative to the aqueous extract, the methanol extract contained a higher amount of the secondary metabolites. However, both extracts exhibited appreciable and dose-dependent capacities for quenching DPPH, ABTS•+ and NO• free radicals, and potent ferric reducing ability to levels comparable to those of ascorbic acid. The crude methanol extract showed significantly increased (P<0.05) antioxidant activity than the aqueous extract. Conclusion: It was concluded that the extract possesses strong antioxidant properties due to its content of phytochemicals, and provides scientific basis for its ethno medicinal applications.


2020 ◽  
Vol 11 (4) ◽  
pp. 6262-6267
Author(s):  
Krishnamoorthy Meenakumari ◽  
Giridharan Bupesh ◽  
Mayur Mausoom Phukan

The foods from plants were known to ensure against degenerative diseases and maturing because of their antioxidant activitycredited to their high content. Information on antioxidant activity of Indian medicinal plant is abundant. To the best of our knowledge, biological properties have not been accounted in the literature for this species of . As a point, this is the first results to assess the anti-oxidant activity of the plant which belongs to the family . The antioxidant activity of Methanol, , Ethyl acetate and Aqueous extracts of E. was determined using the DPPH free radical scavenging activity, ABTS radical scavenging activity and reducing power assay. The DPPH scavenging activity showed higher activity observed in extract (63%) of E. than (54%), (44%) and aqueous (30%). the ABTS assay inhibition in extract (58%) than (43%), (38%) and aqueous (32%) extracts. The reducing power assay of different extracts was increased in extract (54%) than (40%), (34%) and aqueous (28%) extracts. Overall, the and ethyl acetate extract had higher antioxidant properties than other extract. However, in this study, extracts exhibit great potential for antioxidant activity and may be useful for their nutritional and medicinal functions.


2021 ◽  
Vol 17 (1) ◽  
pp. 147-156
Author(s):  
Mohammed Saleh Al Aboody ◽  

Celery (Apium graveolens Linn, Family: Apiaceae) is a common edible herb used as a spice in the traditional medicine of several nations since time immemorial. The whole plant is extensively used in cooking as soups and salads. A. graveolens has various pharmacological properties such as anticancer, anti-obesity, anti-hepatotoxic, and antihypertensive agents. Hence, it is of interest to document the in vitro cytotoxic, antioxidant, and antimicrobial activity of A. graveolens. The plants were collected in the local market, shade dried, and different parts of the plants were extracted with 70% ethanol using a cold maceration process. Antioxidant tests were performed based on the various radical scavenging methods. Antimicrobial activity and MIC were completed using the respective cup-plate and two-fold serial dilution method. In vitro cytotoxic studies were achieved by the MTT; Sulphorhodamine B assayed total cell protein content. DLA and ESC cells determined the short-term toxicity. The leaf extract exhibited significant antioxidant properties against NO, DPPH, ABTS, LPO, and HPO methods. Thus, potential inhibition against Gram-positive, Gram-negative, and fungal strains within the MIC ranges of 250-500 μg/ml was observed. All the extracts of the plant presented in the study revealed greater cytotoxicity effects against five respective cancer cell lines, L6, Vero, BRL 3A, A-549, L929, and L-929 with the ranging of 443-168.5 μg/ml. Thus, we show that A. graveolens possess a potential cytotoxic, antioxidant, and antimicrobial activity.


2021 ◽  
Vol 25 (1) ◽  
pp. 75-79
Author(s):  
S.O. Olubodun ◽  
G.E. Eriyamremu ◽  
M.E. Ayevbuomwan ◽  
C.I. Nzoputa

The presence of various bioactive components makes it necessary to analyse plants for their potential to act as a source of useful treatments and cures for many inflammatory, infectious and pathogenic diseases. This study was carried out to determine phytochemicals and in-vitro antioxidant activities of the leaf extracts of Acalypha godseffiana. The leaves of A. godseffiana were collected, dried, pulverized and extracted separately with methanol and water using maceration method. The extract was concentrated in vacuo with rotary evaporator at 40oC. The extracts were subjected to quantitative phytochemical analysis and different anti-oxidant analytical procedures like FRAP, DPPH etc to determine the radical scavenging capabilities. The results of phytochemical analysis estimated the quantities and revealed the presence of alkaloids, flavonoids, tannins, saponins and terpenoids which varied in both extracts. The methanol and aqueous extracts exhibited antioxidant activities with relatively high IC50 (IC50 = 3.67 ìg/ml and 4.42ìg/ml respectively) which accounted for a low free radical-scavenging activity when compared with the reference antioxidant, vitamin C (IC50 = 1.51ìg/ml). The results of the study indicates that A. godseffiana leaf extracts contain secondary metabolites and possesses antioxidant properties.


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