Investigation of biological activities and antioxidant effects of newly synthesized α-β substituted unsaturated ketone benzofuran derivatives

Abstract Effects of benzofuran-derived α - β unsaturated ketone-derived compounds, which are newly synthesized and not previously subjected to biological activity testing have been evaluated. The pour test compounds were determined for in vitro antioxidant activity using models namely 1,1-Dihenyl-2-picrylhydrazyl radical (DPPH*) and Lipid Peroxidation (LPO) scavenging methods. Lipophilic vitamins and phytosterols analysis was carried out on an HPLC instrument. The fatty acids in the lipid extract were converted to methyl esters and then analyzed by gas chromatography (GC). Our results show that 1a, 2a, 2c coded substances used at 20 µL and 30 µL concentrations have more DPPH free radical scavenging activity than quercetin used as standard. Whereas the amount of LPO was significantly decreased in Quercetin and Resveratrol groups and 1a coded substance compared to the control and FR groups (p < 0.0001). 1c coded substance partially increased the amount of GSH (p < 0.01). When effects of 1b, 2c coded substances on lipophilic vitamins and phytosterol profile in S. Cerevisiae yeast cell were examined; the amounts of α-tocopherol, δ- tocopherol, vitamin K1, and Stigmasterol increased in all groups compared to the control. When effects of 1c, 2a coded substances on lipophilic vitamins and phytosterol profile in S. Cerevisiae Yeast Cell were examined; the amounts of α- tocopherol, vitamin K1, and Stigmasterol increased compared to the control group.

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α-Glucosidase Inhibition, Antioxidant and Docking Studies of Hydroxycoumarins and their Mono and Bis O-alkylated/acetylated Analogs

Letters in Drug Design & Discovery ◽

10.2174/1570180814666170602081941 ◽

2018 ◽

Vol 15 (2) ◽

pp. 127-135 ◽

Cited By ~ 3

Author(s):

Parvesh Singh ◽

Nomandla Ngcoya ◽

Ramgopal Mopuri ◽

Nagaraju Kerru ◽

Neha Manhas ◽

...

Keyword(s):

In Silico ◽

Biological Activities ◽

Wide Spectrum ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Catalytic Site ◽

Docking Simulations ◽

In Silico Docking ◽

Anti Oxidant

Background: Diabetes Mellitus (DM) is a complex metabolic disease illustrated by abnormally high levels of plasma glucose or hyperglycaemia. Accordingly, several α-glucosidase inhibitors have been developed for the treatment of diabetes and other degenerative disorders. While, a coumarin ring has the privilege to represent numerous natural and synthetic compounds with a wide spectrum of biological activities e.g. anti-cancer, anti-HIV, anti-viral, anti-malarial, anti-microbial, anti-convulsant, anti-hypertensive properties. Besides this, coumarins have also shown potential to inhibit α-glucosidase leading to a generation of new promising antidiabetic agents. However, the testing of O-substituted coumarins for α-glucosidase inhibition has evaded the attention of medicinal chemists. Methods: For O-alkylation/acetylation reactions, the hydroxyl coumarins (A-B) initially activated by K2CO3 in dry DMF were reacted with variedly substituted haloalkanes at room temperature under nitrogen. The synthesized compounds were tested for their α-glucosidase (from Saccharomyces cerevisiae) inhibitory activity and anti-oxidant activity using DPPH radical scavenging activity. In silico docking simulations were conducted using CDocker module in DS (Accelrys) to explore the binding modes of the representative compounds in the catalytic site of α-glucosidase. Results: All the coumarin analogues (A1, B1, A2-A10, B2-B8) including their precursors (A-B) were evaluated for their in vitro α-glucosidase inhibition using acarbose as a standard inhibitor. All the mono O-alkylated coumarins (except A1) showed significant (p <0.05) α-glucosidase inhibition relative to the hydroxyl coumarin (A) with IC50 values ranging between 11.084±0.117 to 145.24± 29.22 µg/mL. Compound 7-(benzyloxy)-4, 5-dimethyl-2H-chromen-2-one (A9) bearing a benzyl group (Ph-CH2-) at position 7 showed a remarkable (p <0.05) increase in the activity (IC50 = 11.084±0.117 µg/mL), almost four-fold more than acarbose (IC50 = 40.578±5.999 µg/mL). The introduction of –NO2 group dramatically improved the anti-oxidant activity of coumarin, while the O-alkylation/acetylation decreased the activity. Conclusion: The present study describes the synthesis of functionalized coumarins and their evaluation for α-glucosidase inhibition and antioxidant activity under in vitro conditions. Based on IC50 data, the mono O-alkylated coumarins were observed to be stronger inhibitors of α-glucosidase with respect to their bis O-alkylated analogues. Coumarin (A9) bearing O-benzyloxy group displayed the strongest α-glucosidase inhibition, even higher than the standard inhibitor acarbose. The coumarin (A10) bearing –NO2 group showed the highest anti-oxidant activity amongst the synthesized compounds, almost comparable to the ascorbic acid. Finally, in silico docking simulations revealed the role of hydrogen bonding and hydrophobic forces in locking the compounds in catalytic site of α-glucosidase.

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Investigation of the Anti-cataract and Antioxidant Activities of Cnidoscolus aconitifolius Leaves Extract In vitro

Iraqi Journal of Science ◽

10.24996/ijs.2021.62.1.3 ◽

2021 ◽

pp. 28-38

Author(s):

Henry Bulama ◽

Daniel Dahiru ◽

Joshua Madu

Keyword(s):

Total Protein ◽

Antioxidant Activities ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Reducing Power ◽

Control Group ◽

Scavenging Activity ◽

Aqueous Fraction ◽

Cnidoscolus Aconitifolius

Background: Cataract is a major cause of visual impairment and blindness around the world. This study evaluated the in vitro antioxidant and anti-cataract activities of Cnidoscolus aconitifolius leaves extract and fractions. Antioxidant activities were evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2-azinobis (3-ethylbenzothiozoline-6-sulfonic acid) (ABTS), total reducing power, and hydrogen peroxide scavenging assays. Anti-cataract potential was evaluated in vitro using goat lenses divided into eight groups of different treatments and incubated in artificial aqueous humor at 37 °C for 72 hours. Glucose-induced opacity in the lenses was observed and biochemical indices quantified (catalase, Malondialdehyde (MDA) and total protein in the lens homogenate). Results: The crude extract and its fractions possess substantial antioxidant activities. The aqueous fraction exhibited the best DPPH radical scavenging activity (IC50 value 78.599 µg/ml); while the dichloromethane fraction exhibited the highest ABTS radical scavenging activity with IC50 66.68 µg/ml. The anti-cataract evaluation of crude and fractions at 250 μg/ml showed a significant increase (p<0.05) in the total protein and catalase activity compared to the cataract control group. The malonaldehyde level decreased significantly (p<0.05) in all the treated groups.

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Phytochemical, in-vitro biological and chemo-preventive profiling of Arisaema jacquemontii Blume tuber extracts

BMC Complementary and Alternative Medicine ◽

10.1186/s12906-019-2668-4 ◽

2019 ◽

Vol 19 (1) ◽

Cited By ~ 1

Author(s):

Saira Tabassum ◽

Muhammad Zia ◽

Esperanza J. Carcahe de Blanco ◽

Riffat Batool ◽

Roohi Aslam ◽

...

Keyword(s):

Cell Lines ◽

Biological Activities ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Reducing Power ◽

Scavenging Activity ◽

Zone Of Inhibition ◽

Meoh Extract ◽

Etoac Extract

Abstract Background Arisaema jacquemontii is traditionally used in treatment of different diseases. In this study, phytochemical, in vitro biological and chemo-preventive screening of A. jacquemontii was carried out to explore its pharmacological potential. Methods The dried tuber of A. jacquemontii was extracted in 11 organic solvent mixture of different polarity. The extracts were screened for phytochemical assays (phenolics and flavonoids), antioxidants potential (free radical scavenging activity, total antioxidant activity, reducing power), biological activities (antibacterial, antifungal, cytotoxic, antileishmanial, protein kinase inhibition), and chemopreventive activities using different cell lines through standard protocols. Results Significant amount phenolic contents were determined in EtOH and MeOH extracts (210.3 ± 3.05 and 193.2 ± 3.15 μg GAE/mg, respectively). Maximum flavonoid content was determined in MeOH extract (22.4 ± 4.04 μg QE/mg). Noteworthy, DPPH scavenging activity was also recorded for MeOH extract (87.66%) followed by MeOH+EtOAc extract (85.11%). Considerable antioxidant capacity (7.8 ± 0.12 μg AAE/mg) and reducing power (3.1 ± 0.15 μg AAE/mg) was observed in extract of MeOH. The LC50 against brine shrimp and leishmanial parasite was found 9.01 and 12.87 μg/mL for n-Hex and CHCl3 extracts, respectively. The highest zone of inhibition against Streptomyces hyphae formation (12.5 ± 1.77 mm) by n-Hex extract. Growth zone of inhibition 13.8 ± 1.08 mm was recorded for EtOAc and MeOH extracts, respectively against Micrococcus luteus while 10.0 ± 0.11 mm for MeOH extract against Aspergillus flavus. In-vitro cytotoxic assay showed that n-Hex extract had higher cytotoxicity against DU-145 prostate cancer and HL-60 cancer cell lines. NF-kB and MTP potential showed 34.01 and 44.87 μg/mL for n-Hex and CHCl3 extracts, respectively in chemo-preventive potential. Conclusion The study concludes that Arisaema jacquemontii bears significant phytochemical activity and pharmacological activities, this plant can be further explored for isolation of active component against a number of aliments.

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Antioxidant, Antidiabetic, and Anticholinesterase Activities and Phytochemical Profile of Azorella glabra Wedd

Plants ◽

10.3390/plants8080265 ◽

2019 ◽

Vol 8 (8) ◽

pp. 265 ◽

Cited By ~ 6

Author(s):

Immacolata Faraone ◽

Dilip K. Rai ◽

Daniela Russo ◽

Lucia Chiummiento ◽

Eloy Fernandez ◽

...

Keyword(s):

Biological Activities ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Reducing Power ◽

Ethanol Extract ◽

Flowering Plant ◽

Acetylcholinesterase Inhibition ◽

Neutral Radical ◽

Phytochemical Profile

Oxidative stress is involved in different diseases, such as diabetes and neurodegenerative diseases. The genus Azorella includes about 70 species of flowering plant species; most of them are commonly used as food and in particular as a tea infusion in the Andean region of South America in folk medicine to treat various chronic diseases. Azorella glabra Wedd. aerial parts were firstly analyzed for their in vitro antioxidant activity using different complementary assays. In particular, radical scavenging activity was tested against biological neutral radical DPPH; ferric reducing power and lipid peroxidation inhibitory capacity (FRAP and Beta-Carotene Bleaching tests) were also determined. The Relative Antioxidant Capacity Index (RACI) was used to compare data obtained by different assays. Then, the inhibitory ability of samples was investigated against α-amylase and α-glucosidase enzymes involved in diabetes and against acetylcholinesterase and butyrylcholinesterase enzymes considered as strategy for the treatment of Parkinson’s or Alzheimer’s diseases. Moreover, the phytochemical profile of the sample showing the highest RACI (1.35) and interesting enzymatic activities (IC50 of 163.54 ± 9.72 and 215.29 ± 17.10 μg/mL in α-glucosidase and acetylcholinesterase inhibition, respectively) was subjected to characterization and quantification of its phenolic composition using LC-MS/MS analysis. In fact, the ethyl acetate fraction derived from ethanol extract by liquid/liquid extraction showed 29 compounds, most of them are cinnamic acid derivatives, flavonoid derivatives, and a terpene. To the best of our knowledge, this is the first report about the evaluation of significant biological activities and phytochemical profile of A. glabra, an important source of health-promoting phytochemicals.

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Protective effects of ethanolic extract of Lemon Beebrush (Aloysia citrodora) leaf against hypoxia-induced lethality in mice

Tabari Biomedical Student Research Journal ◽

10.18502/tbsrj.v1i4.2242 ◽

2020 ◽

Author(s):

Mohammad Hossein Hosseinzadeh ◽

Mohammad Ali Ebrahimzadeh

Keyword(s):

Biological Activities ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Positive Control ◽

Experimental Models ◽

Total Phenolic ◽

Control Group ◽

Antihypoxic Activity ◽

Significant Activity ◽

Protective Effects

Lemon Beebrush, known as Lippia citroiodora and Aloysia citrodora is a known medicinal plant in Iran. Many biological activities have been reported from this plant. In spite of many works, nothing is known about protective effect of A. citrodora against hypoxia conditions. In this study, protective effects of A. citrodora leaf extract against hypoxia-induced lethality in mice were evaluated by three experimental models of hypoxia, asphyctic, haemic and circulatory. Its phenol and flavonoid contents and antioxidant activity were also evaluated. Statistically significant protective activities were established in some doses of extract in three models. Antihypoxic activity was especially pronounced in circulatory hypoxia where extract at 62.5 mg kg-1 prolonged the latency for death with respect to control group (p<0.01). The effect was dose dependent. At 250 mg kg-1, it prolonged the latency for death with the same activity of propranolol (20 mg kg-1), that used as positive control (p>0.05). Extract showed weak activity in haemic model. Only at the highest tested dose, 250 mg kg-1, it significantly prolonged latency for death with respect to control group (p<0.05). Extract at this dose showed the same activity of propranolol which used as positive control (p>0.05). In asphytic model, extract at the highest tested dose showed statistically significant activity respect to the control. At 250 mg kg-1, it significantly prolonged the latency for death (26.84 ± 4.11 vs. 19.45 ± 1.13 min, p = 0.0006). At 125 mg kg-1, it also prolonged survival time but this increase was not significantly different. Phenytoin that used as positive control kept mice alive for 29.60 ± 2.51 min (p<0.0001). Extract at 250 mg kg-1 showed the same activity of phenytoin (p>0.05). The total phenolic content was 342.9 ± 11.5 mg gallic acid equivalent/g of extract powder and flavonoid content was 90.2 ± 7.8 mg quercetin equivalent/g of extract powder. IC50 for DPPH radical-scavenging activity was 21.97 ± 2.4 mg/ml. The presence of polyphenols in this plant may be a proposal mechanism for reported antihypoxic activities.

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Muscari comosum L. Bulb Extracts Modulate Oxidative Stress and Redox Signaling in HepG2 Cells

Molecules ◽

10.3390/molecules26020416 ◽

2021 ◽

Vol 26 (2) ◽

pp. 416

Author(s):

Fabiana Giglio ◽

Maria Antonietta Castiglione Morelli ◽

Ilenia Matera ◽

Chiara Sinisgalli ◽

Rocco Rossano ◽

...

Keyword(s):

Antioxidant Activity ◽

Hepg2 Cells ◽

Biological Activities ◽

Radical Scavenging Activity ◽

Redox Homeostasis ◽

Folk Medicine ◽

Radical Scavenging ◽

In Vitro Assays ◽

South Italy

Muscari comosum L. bulbs are commonly used as food in South Italy and also in folk medicine. By evaluating in vitro antioxidant activity and biological activities of their aqueous and methanol extracts, we shed light on the potential role, including both the nutraceutical and health benefits, of this plant. Total polyphenol content (TPC) and total flavonoid content (TFC) were evaluated by the Folin–Ciocalteu method and by the aluminum chloride method, respectively. Antioxidant activity was investigated by three in vitro assays and relative antioxidant capacity index (RACI) was calculated to compare results obtained by different tests. The extracts were tested to evaluate their possible involvement in redox homeostasis, using the human hepatoma (HepG2) cell line used as model. The extracts exhibited concentration/solvent dependent radical scavenging activity, as well as dysregulation of some genes involved in redox pathways by promoting Nrf2, SOD-2, GPX1, ABCC6 and ABCG2 expression. NMR metabolomics analysis suggests that HepG2 cells treated with Muscari comosum extracts experience changes in some metabolites involved in various metabolic pathways.

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Green Ultrasound Assisted Extraction of trans Rosmarinic Acid from Plectranthus scutellarioides (L.) R.Br. Leaves

Plants ◽

10.3390/plants8030050 ◽

2019 ◽

Vol 8 (3) ◽

pp. 50 ◽

Cited By ~ 8

Author(s):

Duangjai Tungmunnithum ◽

Laurine Garros ◽

Samantha Drouet ◽

Sullivan Renouard ◽

Eric Lainé ◽

...

Keyword(s):

Rosmarinic Acid ◽

Biological Activities ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Ultrasound Assisted Extraction ◽

Pure Ethanol ◽

Ultrasound Frequency ◽

Assisted Extraction ◽

Ultrasound Assisted

Painted nettle (Plectranthus scutellarioides (L.) R.Br.) is an ornamental plant belonging to Lamiaceae family, native of Asia. Its leaves constitute one of the richest sources of trans-rosmarinic acid, a well-known antioxidant and antimicrobial phenolic compound. These biological activities attract interest from the cosmetic industry and the demand for the development of green sustainable extraction processes. Here, we report on the optimization and validation of an ultrasound-assisted extraction (USAE) method using ethanol as solvent. Following preliminary single factor experiments, the identified limiting extraction parameters (i.e., ultrasound frequency, extraction duration, and ethanol concentration) were further optimized using a full factorial design approach. The method was then validated following the recommendations of the association of analytical communities (AOAC) to ensure the precision and accuracy of the method used to quantify trans-rosmarinic acid. Highest trans-rosmarinic acid content was obtained using pure ethanol as extraction solvent following a 45-minute extraction in an ultrasound bath operating at an ultrasound frequency of 30 kHz. The antioxidant (in vitro radical scavenging activity) and antimicrobial (directed toward Staphylococcus aureus ACTT6538) activities were significantly correlated with the trans-rosmarinic acid concentration of the extract evidencing that these key biological activities were retained following the extraction using this validated method. Under these conditions, 110.8 mg/g DW of trans-rosmarinic acid were extracted from lyophilized P. scutellarioides leaves as starting material evidencing the great potential of this renewable material for cosmetic applications. Comparison to other classical extraction methods evidenced a clear benefit of the present USAE method both in terms of yield and extraction duration.

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Comparative Effects of Vitamin K2 and Vitamin E on Experimental Arteriosclerosis

International Journal for Vitamin and Nutrition Research ◽

10.1024/0300-9831.69.1.23 ◽

1999 ◽

Vol 69 (1) ◽

pp. 23-26 ◽

Cited By ~ 6

Author(s):

Seyama ◽

Hayashi ◽

Takegami ◽

Usami

Keyword(s):

Vitamin E ◽

Vitamin K ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Male Rats ◽

Side Chain ◽

Scavenging Activity ◽

Experimental Conditions ◽

Experimental Arteriosclerosis

The comparative effects of vitamin K2 and vitamin E on aortic calcium (Ca) and inorganic phosphorus (P) levels in the aorta and the elastin fraction (fr.) were investigated in male rats after experimental arteriosclerosis was induced by vitamin D2 with atherogenic diet. Both vitamin K2 (100 mg/kg b.w.) and vitamin E (40 mg/kg b.w.) inhibited the increase of Ca and P in the aorta and the elastin fr. from the arteriosclerotic rats. Vitamin K2 (50 mg/kg b.w.) also suppressed the deposition of Ca and P in the aorta, but there was no change due to vitamin K3 or geranylgeraniol (side chain of vitamin K2) administration. Both vitamin K2 and vitamin E showed lipid radical scavenging activity in the in vitro experiment. However, neither vitamin K3 nor geranylgeraniol exhibited anti-arteriosclerotic or radical scavenging activity under the above experimental conditions. It is suggested that vitamin K2 and vitamin E promoted an antiarteriosclerotic effect by radical scavenging activity. These actions of vitamin K2 are required in the structure of 2-methylnaphthoquinone and its side chain (geranylgeraniol).

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In vivo and in vitro antioxidant effects of three Veronica species

Open Life Sciences ◽

10.2478/s11535-012-0041-4 ◽

2012 ◽

Vol 7 (3) ◽

pp. 559-568 ◽

Cited By ~ 4

Author(s):

Jelena Živković ◽

Tatjana Ćebović ◽

Zoran Maksimović

Keyword(s):

Antioxidant Activity ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Thiobarbituric Acid ◽

Butylated Hydroxytoluene ◽

Antioxidant Systems ◽

Antioxidant Power ◽

Antioxidant Effects

AbstractThe aim of the present study was to examine the antioxidant activity of three Veronica species (Plantaginaceae). The antioxidant potential of various extracts obtained from aerial flowering parts was evaluated by DPPH-free (1,1-diphenyl-2-picrylhydrazyl-free) radical scavenging activity and ferric-reducing antioxidant power assays. Considerable antioxidant activity was observed in the plant samples (FRAP values ranged from 0.97 to 4.85 mmol Fe2+/g, and DPPH IC50 values from 12.58 to 66.34 µg/ml); however, these levels were lower than the activity of the control compound butylated hydroxytoluene (BHT) (FRAP: 10.58 mmol Fe2+/g; DPPH IC50: 9.57 µg/ml). Also, the in vivo antioxidant effects were evaluated in several hepatic antioxidant systems in rats (activities of glutathione peroxidase, glutathione reductase, peroxidase, catalase, xanthine oxidase, glutathione content and level of thiobarbituric acid reactive substances) after treatment with different Veronica extracts, or in combination with carbon tetrachloride (CCl4). Pretreatment with 100 mg/kg b.w. of Veronica extracts inhibited CCl4-induced liver injury by decreasing TBA-RS level, increasing GSH content, and bringing the activities of CAT and Px to control levels. The present study suggests that the extracts analyzed could protect the liver cells from CCl4-induced liver damage by their antioxidative effect on hepatocytes.

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Quinoline Functionalized Schiff Base Silver (I) Complexes: Interactions with Biomolecules and In Vitro Cytotoxicity, Antioxidant and Antimicrobial Activities

Molecules ◽

10.3390/molecules26051205 ◽

2021 ◽

Vol 26 (5) ◽

pp. 1205

Author(s):

Adesola A. Adeleke ◽

Sizwe J. Zamisa ◽

Md. Shahidul Islam ◽

Kolawole Olofinsan ◽

Veronica F. Salau ◽

...

Keyword(s):

Schiff Base ◽

Antioxidant Activities ◽

Biological Activities ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Antimicrobial Activities ◽

In Vitro Cytotoxicity ◽

Spectroscopic Techniques ◽

Antioxidant Power

A series of fifteen silver (I) quinoline complexes Q1–Q15 have been synthesized and studied for their biological activities. Q1–Q15 were synthesized from the reactions of quinolinyl Schiff base derivatives L1–L5 (obtained by condensing 2-quinolinecarboxaldehyde with various aniline derivatives) with AgNO3, AgClO4 and AgCF3SO3. Q1–Q15 were characterized by various spectroscopic techniques and the structures of [Ag(L1)2]NO3Q1, [Ag(L1)2]ClO4Q6, [Ag(L2)2]ClO4Q7, [Ag(L2)2]CF3SO3Q12 and [Ag(L4)2]CF3SO3Q14 were unequivocally determined by single crystal X-ray diffraction analysis. In vitro antimicrobial tests against Gram-positive and Gram-negative bacteria revealed the influence of structure and anion on the complexes′ moderate to excellent antibacterial activity. In vitro antioxidant activities of the complexes showed their good radical scavenging activity in ferric reducing antioxidant power (FRAP). Complexes with the fluorine substituent or the thiophene or benzothiazole moieties are more potent with IC50 between 0.95 and 2.22 mg/mL than the standard used, ascorbic acid (2.68 mg/mL). The compounds showed a strong binding affinity with calf thymus-DNA via an intercalation mode and protein through a static quenching mechanism. Cytotoxicity activity was examined against three carcinoma cell lines (HELA, MDA-MB231, and SHSY5Y). [Ag(L2)2]ClO4Q7 with a benzothiazole moiety and [Ag(L4)2]ClO4Q9 with a methyl substituent had excellent cytotoxicity against HELA cells.

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