Design and Synthesis of π-Extended Resveratrol Analogues and In Vitro Antioxidant and Anti-Inflammatory Activity Evaluation

The research on resveratrol (1) has been conducted intensively over a long time due to its proven antioxidant activity and disease-fighting capabilities. Many efforts have also been made to increase these biological effects. In the present study, six new extended aromatic resveratrol analogues containing naphthalene (2) and its bioisosteres quinoline (3 and 4), isoquinoline (5) quinoxaline (6) and quinazoline (7) scaffolds were designed and synthesized using an annulation strategy. The antioxidant and anti-inflammatory activities of these compounds were investigated. All compounds showed better antioxidant activity than resveratrol in ABTS assay. As for the anti-inflammatory test, 5 and 7 exhibited better activity than resveratrol. It is worth noting that nitrogen substitution on the extended aromatic resveratrol analogues has a significant impact on cell viability. Taking the antioxidant activities and NO inhibition activities into consideration, we conclude that isoquinoline analogue 5 may qualify for the further investigation of antioxidant and anti-inflammatory therapy. Furthermore, our study results suggest that in order to improve the biological activity of polyphenolic compounds, extended aromaticity and nitrogen substitution strategy could be a viable method for the design of future drug candidates.

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Semipurified Ethyl Acetate Partition of Methanolic Extract ofMelastoma malabathricumLeaves Exerts Gastroprotective Activity Partly via Its Antioxidant-Antisecretory-Anti-Inflammatory Action and Synergistic Action of Several Flavonoid-Based Compounds

Oxidative Medicine and Cellular Longevity ◽

10.1155/2017/6542631 ◽

2017 ◽

Vol 2017 ◽

pp. 1-14 ◽

Cited By ~ 5

Author(s):

Noor Wahida Ismail Suhaimy ◽

Ahmad Khusairi Noor Azmi ◽

Norhafizah Mohtarrudin ◽

Maizatul Hasyima Omar ◽

Siti Farah Md. Tohid ◽

...

Keyword(s):

Antioxidant Activity ◽

Ethyl Acetate ◽

Methanolic Extract ◽

Antioxidant Activities ◽

Gastric Wall ◽

Synergistic Action ◽

Gastroprotective Activity ◽

Gastric Mucus ◽

Anti Inflammatory

Recent study has demonstrated the gastroprotective activity of crude methanolic extract ofM. malabathricumleaves. The present study evaluated the gastroprotective potential of semipurified extracts (partitions): petroleum ether, ethyl acetate (EAMM), and aqueous obtained from the methanolic extract followed by the elucidation of the gastroprotective mechanisms of the most effective partition. Using the ethanol-induced gastric ulcer assay, all partitions exerted significant gastroprotection, with EAMM being the most effective partition. EAMM significantly (i) reduced the volume and acidity (free and total) while increasing the pH of gastric juice and enhanced the gastric wall mucus secretion when assessed using the pylorus ligation assay, (ii) increased the enzymatic and nonenzymatic antioxidant activity of the stomach tissue, (iii) lost its gastroprotective activity following pretreatment with N-omega-nitro-L-arginine methyl ester (L-NAME; NO blocker) or carbenoxolone (CBXN; NP-SH blocker), (iv) exerted antioxidant activity against various in vitro oxidation assays, and (v) showed moderate in vitro anti-inflammatory activity via the LOX-modulated pathway. In conclusion, EAMM exerts a remarkable NO/NP-SH-dependent gastroprotective effect that is attributed to its antisecretory and antioxidant activities, ability to stimulate the gastric mucus production and endogenous antioxidant system, and synergistic action of several gastroprotective-induced flavonoids.

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Design, Synthesis, Characterization, Anti-Inflammatory and Antioxidant Evaluation of Certain Novel Pyrazoline Derivatives Containing Imidazo[2,1-b]thiazole Moiety

Asian Journal of Organic & Medicinal Chemistry ◽

10.14233/ajomc.2020.ajomc-p233 ◽

2020 ◽

Vol 5 (1) ◽

pp. 45-50

Author(s):

V.D. Sonawane ◽

B.D. Sonawane ◽

M.J. Dhanavade ◽

K.D. Sonawane ◽

R.B. Bhosale

Keyword(s):

Antioxidant Activity ◽

Antioxidant Activities ◽

Design Synthesis ◽

Standard Drug ◽

Drug Designing ◽

Antioxidant Evaluation ◽

Future Drug ◽

Anti Inflammatory

In present study, a novel series of substituted imidazo[2,1-b]thiazole pyrazoline derivatives (2a-e) and (3a-e) from the reference compound imidazo[2,1-b]thiazole chalcones (1a-e) in PEG-400 by using hydrazine hydrate and phenyl hydrazine was synthesized. Characterization of newly synthesized compounds was done using IR and 1H NMR. Further, imidazo[2,1-b]thiazole pyrazoline derivatives were subjected to check their in vitro antioxidant activities at a concentration of 0.5 mmol/L in methanol. Compounds 2c, 2d, 3c, 3d and 3e showed comparatively good activity than standard drug diclofenac. The anti-inflammatory activity of compounds 2c, 2d, 2e, 3c, 3d and 3e were comparable with standard drug. Similarly, all these compounds possess good antioxidant activity as compared to ascorbic acid (vitamin C); compared to the value of DPPH and SOD antioxidant activity 44.18 % and 74.07 %, respectively. These synthesized compounds exhibited a good anti-inflammatory and antioxidant activities hence might be useful in future drug designing studies.

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Design and Synthesis of Benzopyranopyrimidinyl Phosphonates as Cytotoxic and Antioxidant Agents

Letters in Drug Design & Discovery ◽

10.2174/1570180815666180606083418 ◽

2019 ◽

Vol 16 (7) ◽

pp. 721-733

Author(s):

Sarva Santhisudha ◽

Gundluru Mohan ◽

Tenkayala Sobha Rani ◽

Peddaiahgari Vasu Govardhana Reddy ◽

Cirandur Suresh Reddy

Keyword(s):

Antioxidant Activity ◽

Cytotoxic Activity ◽

Carbon Nitride ◽

Antioxidant Activities ◽

Design And Synthesis ◽

Antioxidant Agents ◽

Green Conditions ◽

Mcf 7 ◽

In Vitro Antioxidant Activity

Background: A concatenation of bioactive diethyl(2-hydroxyphenylsubstituted) benzopyrano pyrimidinyl phosphonates were synthesized under eco-friendly green conditions in the presence of palladium doped graphitic carbon nitride (Pd@g-C3N4) as catalyst. Methods: he title compounds were evaluated for cytotoxic activity against MCF-7, SW-480, HeLa and HL-7702 cell lines and in-vitro antioxidant activity by DPPH, NO and H2O2 methods. Results: he synthesized compounds manifested robust cytotoxic and antioxidant activities. Conclusion: Some of them showed much higher bioactivity than the standards.

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EVALUATION OF ANTIOXIDANT AND ANTI-INFLAMMTORY ACTIVITY OF METHANOLIC EXTRACT OF SOLANUM NIGRUM FRUITS

INTERNATIONAL JOURNAL OF PHARMACEUTICAL EDUCATION AND RESEARCH (IJPER) ◽

10.37021/ijper.v1i1.10 ◽

2019 ◽

Vol 1 (1) ◽

pp. 1-5

Author(s):

Reema Sinha

Keyword(s):

Antioxidant Activity ◽

Methanolic Extract ◽

Antioxidant Activities ◽

Solanum Nigrum ◽

Inflammatory Activity ◽

Control Group ◽

Root Bark ◽

Dpph Method ◽

Anti Inflammatory

Introduction: Solanum nigrum (Linn) is known as Makoy and Black night shade. It is found in India and in cultivated ground. This plant has been reported for hepatoprotective, antibacterial, antimicrobial, antiseptic, narcotic, antispasmodic, anti-inflammatory, CNS depressant, molluscidal, antiulcer, cardiac depressant, immunomodulatory and antioxidant activities. It is widely used as expectorant, anodyne, vulnerary, digestive, laxative, diuretic, cardiotonic, depurative, diaphoretic, febrifuge, swelling, wounds, ulcer, dyspepsia, ophthalmic disorder, vomiting, cardiac disorder, leprosy, skin disease, fever, splenomegaly, hemorrhoids, hoarseness, nephropathy, dropsy, gonorrhea.Leaves are use as poultice for rheumatic an gouty joints, decoction of berries and flower useful in cough, erysipelas, rat bite, bronchitis, pulmonary tuberculosis, fever, diarrhea, ophthalmopathy and hydrophobia. Root bark is useful in diseases of ear, eye, nose and hepatitis. Material and methods: For anti-inflammatory activity adult wister rats of both sexes weighing between 200-250g was used for experiment. Group-1 received 0.5% CMC suspension (control) group 2, 3 and 4 received methanolic extracts (125, 250 and 375 mg/kg) of S. nigrum respectively. Group 5 received diclofenac (reference standard 1mg/kg). The antioxidant activity of the fruit of S. nigrum was determined by using a method based on the reduction of methanolic solution of colored free radical 1, 1 di phenyl-1-2 picryl hydrazyl (DPPH). Result and discussion: Methanolic extract of Solanum nigrum Linn. fruit has shown antioxidant activity in vitro DPPH Method. The methanolic extract of S. nigrum (375 mg/kg) prevented the formation of edema induced by carrageenan and thus showed significant anti-inflammatory activity (p<0.05). Conclusion: The data collectively indicates that methanolic extract of Solanum nigrum fruits have potential anti-inflammatory and antioxidant activity.

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Multiple Biological Activities of Rhododendron przewalskii Maxim. Extracts and UPLC-ESI-Q-TOF/MS Characterization of Their Phytochemical Composition

Frontiers in Pharmacology ◽

10.3389/fphar.2021.599778 ◽

2021 ◽

Vol 12 ◽

Author(s):

Lixia Dai ◽

Jian He ◽

Xiaolou Miao ◽

Xiao Guo ◽

Xiaofei Shang ◽

...

Keyword(s):

Antioxidant Activity ◽

Antioxidant Activities ◽

Underlying Mechanism ◽

Raw 264.7 Cells ◽

Raw 264.7 ◽

Active Compounds ◽

Anti Inflammatory ◽

Ethanol Extracts ◽

Tof Ms

Backgroud:Rhododendron przewalskii Maxim. is an evergreen shrub that is used as a traditional medicine in China. However, the modern pharmacology and the chemical components of this plant has not been studied. In this paper, we aimed to investigate the antifungal, anti-inflammatory and antioxidant activities and underlying mechanism of its aqueous and ethanol extracts, and analyze their chemical composition and active compounds of R. przewalskii.Methods: The antifungal activity was determined in vitro, and anti-inflammatory and antioxidant activities and underlying mechanism of its aqueous and ethanol extracts were evaluated in vitro and in RAW 264.7 cells. The chemical composition were analyzed using UPLC-ESI-Q-TOF/MS, and the contents of six compounds were determined via HPLC.Results: Both extracts of R. przewalskii showed promising anti-inflammatory activity in vitro; decreased the production of four inflammatory cytokines, namely, nitric oxide, IL-1β, IL-6 and TNF-ɑ, in RAW 264.7 cells induced by lipopolysaccharide; and exhibited weak cytotoxicity. The extracts significantly scavenged DPPH radicals, superoxide radicals and hydroxyl radicals to exert antioxidant effects in vitro. The two extracts also exhibited cellular antioxidant activity by increasing superoxide dismutase and CAT activities and decreasing malondialdehyde content in RAW 264.7 cells induced by LPS. However, the antifungal activity of the two extracts was weak. Nine flavonoids were identified by UPLC-ESI-Q-TOF/MS. Of these, six compounds were analyzed quantitatively, including avicularin, quercetin, azaleatin, astragalin and kaempferol, and five compounds (myricetin 3-O-galactoside, paeoniflorin, astragalin, azaleatin and kaempferol) were found in this species for the first time. These compounds demonstrated antioxidant activities that were similar to those of the R. przewalskii extracts and were thought to be the active compounds in the extracts.Conclusion:R. przewalskii extracts presented promising anti-inflammatory and antioxidant activities. The extracts contained amounts of valuable flavonoids (8.98 mg/g fresh material) that were likely the active compounds in the extract contributing to the potential antioxidant activity. These results highlight the potential of R. przewalskii as a source of natural antioxidant and anti-inflammatory agents for the pharmaceutical industry.

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In vitro ANTI-INFLAMMATORY AND ANTIOXIDANT EVALUATION OF AN INDIGENOUS MEDICINAL PLANT – Pterospermum rubiginosum

Journal of Experimental Biology and Agricultural Sciences ◽

10.18006/2021.9(5).687.696 ◽

2021 ◽

Vol 9 (5) ◽

pp. 687-696

Author(s):

Rajamohanan J Anish ◽

◽

Arun A Rauf ◽

Keyword(s):

Nitric Oxide ◽

Antioxidant Activity ◽

Antioxidant Activities ◽

Radical Scavenging Activity ◽

Colorimetric Method ◽

Radical Scavenging ◽

Scavenging Activity ◽

Cellular Viability ◽

Anti Inflammatory

The current study was carried out to determine the antioxidant potential, anti-inflammatory activity, and cellular viability of Pterospermum rubiginosum (PR), a tropical tree endemic to the Western Ghats. The antioxidant activities of the PR bark methanolic (PRME) and aqueous extract (PRAQ) were tested using ABTS as well as superoxide, nitric oxide, and hydroxyl radical assays. Total antioxidant activity was evaluated by adopting the colorimetric method and correlation with their antioxidant activities was derived by Pearson co-efficient analysis. The PRME showed the highest ABTS radical scavenging activity, EC50 (46.09µg/ml) followed by PRAQ (52.08µg/ml). Furthermore, the PRME exhibited the highest scavenging activity against superoxide, nitric oxide, and hydroxyl radicals. The MTT assay results revealed good cellular viability up to a concentration of 100µg/ml with an EC50 (106.869µg/ml). The inflammatory mediators such as Cox-2, IL-1β, IL-6, and NF-kB were reduced during the treatment of PRME in LPS stimulated RAW cells. The stress marker in rat liver cells such as glutathione reductase (GR), glutathione peroxidase (GPx), and reduced glutathione (GSH) levels was found in normal levels when compared to the untreated group of rats. The antioxidant enzyme superoxide dismutase and catalase also exhibited notable bioactivity in PRME treated groups up to a concentration of 1000µg/ml. The present study showed excellent In vitro and In vivo antioxidant activity; the potent anti-inflammatory ability of PRME in reducing the LPS induced inflammation in cell culture conditions.

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Antioxidant Activity, Phenolic Content and Hematoprotective Effects of Cleome arabica Polyphenolic Leaf Extract

Phytothérapie ◽

10.3166/phyto-2019-0206 ◽

2019 ◽

Author(s):

C. Tigrine ◽

A. Kameli

Keyword(s):

Antioxidant Activity ◽

Biological Effects ◽

Reducing Power ◽

Hematological Toxicity ◽

Protective Effects ◽

Ferrous Ions ◽

Polyphenolic Extract ◽

Cleome Arabica

In this study a polyphenolic extract from Cleome arabica leaves (CALE) was investigated for its antioxidant activity in vitro using DPPH•, metal chelating and reducing power methods and for its protective effects against AraC-induced hematological toxicity in vivo using Balb C mice. Results indicated that CALE exhibited a strong and dose-dependent scavenging activity against the DPPH• free radical (IC50 = 4.88 μg/ml) and a high reducing power activity (EC50 = 4.85 μg/ml). Furthermore, it showed a good chelating effects against ferrous ions (IC50 = 377.75 μg/ml). The analysis of blood showed that subcutaneous injection of AraC (50 mg/kg) to mice during three consecutive days caused a significant myelosupression (P < 0.05). The combination of CALE and AraC protected blood cells from a veritable toxicity. Where, the number of the red cells, the amount of hemoglobin and the percentage of the hematocrite were significantly high. On the other hand, AraC cause an elevation of body temperature (39 °C) in mice. However, the temperature of the group treated with CALE and AraC remained normal and did not exceed 37.5 °C. The observed biological effects of CALE, in vitro as well as in vivo, could be due to the high polyphenol and flavonoid contents. In addition, the antioxidant activity of CALE suggested to be responsible for its hematoprotective effect.

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Study of Antihyperglycemic, Antihyperlipidemic and Antioxidant Activities of Tannins Extracted from Warionia saharae Benth. & Coss

Endocrine Metabolic & Immune Disorders - Drug Targets ◽

10.2174/1871530318666181029160539 ◽

2019 ◽

Vol 19 (2) ◽

pp. 189-198 ◽

Cited By ~ 3

Author(s):

Mohammed Ajebli ◽

Fadwa El Ouady ◽

Mohamed Eddouks

Keyword(s):

Antioxidant Activity ◽

Antioxidant Activities ◽

Histopathological Examination ◽

Density Lipoprotein ◽

Hdl Cholesterol ◽

Diabetic Rats ◽

Lipid Lowering ◽

Glucose Levels ◽

Soxhlet Apparatus

Background and Objective: Warionia saharae Benth & Coss, a plant belonging to Asteraceae family, is used for its anti-diabetic properties in Morocco. The objective of this study was to evaluate the effect of tannins extracted from Warionia saharae (W. saharae) on blood glucose levels and lipid profile in normal and streptozotocin(STZ)-induced diabetic rats. Methods: Tannins (TE) were extracted from W. saharae using Soxhlet apparatus and different organic solvents. Single and once daily repeated oral administration of TE (10 mg/kg) for 15 days were used to evaluate the glucose and lipid-lowering activity in normal and diabetic rats. Furthermore, glucose test tolerance, liver histopathological examination and in vitro antioxidant activity of TE were carried out in this study. Results: The results showed that TE was able to exert antihyperglycemic and lowering total cholesterol effects as well as improvement of the high-density lipoprotein (HDL)-cholesterol serum level after 15 days of treatment. Furthermore, TE improved glucose tolerance, histopathological status of liver in diabetic rats and demonstrated interesting antioxidant activity. Conclusion: In conclusion, the present investigation revealed that TE possesses potent antidiabetic and antihyperlipidemic activities as claimed in different ethnopharmacological practices.

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Insights into the Antioxidant Mechanism of Newly Synthesized Benzoxazinic Nitrones: In Vitro and In Silico Studies with DPPH Model Radical

Antioxidants ◽

10.3390/antiox10081224 ◽

2021 ◽

Vol 10 (8) ◽

pp. 1224

Author(s):

Stefania Marano ◽

Cristina Minnelli ◽

Lorenzo Ripani ◽

Massimo Marcaccio ◽

Emiliano Laudadio ◽

...

Keyword(s):

Antioxidant Activity ◽

Epr Spectroscopy ◽

Point Of View ◽

Uv Spectrophotometry ◽

Design And Synthesis ◽

Antioxidant Mechanism ◽

Primary Mechanism ◽

In Silico Studies ◽

Wide Range

Synthetic nitrone spin-traps are being explored as therapeutic agents for the treatment of a wide range of oxidative stress-related pathologies, including but not limited to stroke, cancer, cardiovascular, and neurodegenerative diseases. In this context, increasing efforts are currently being made to the design and synthesis of new nitrone-based compounds with enhanced efficacy. The most researched nitrones are surely the ones related to α-phenyl-tert-butylnitrone (PBN) and 5,5-dimethyl-1-pyrroline N-oxide (DMPO) derivatives, which have shown to possess potent biological activity in many experimental animal models. However, more recently, nitrones with a benzoxazinic structure (3-aryl-2H-benzo[1,4]oxazin-N-oxides) have been demonstrated to have superior antioxidant activity compared to PBN. In this study, two new benzoxazinic nitrones bearing an electron-withdrawing methoxycarbonyl group on the benzo moiety (in para and meta positions respect to the nitronyl function) were synthesized. Their in vitro antioxidant activity was evaluated by two cellular-based assays (inhibition of AAPH-induced human erythrocyte hemolysis and cell death in human retinal pigmented epithelium (ARPE-19) cells) and a chemical approach by means of the α,α-diphenyl-β-picrylhydrazyl (DPPH) scavenging assay, using both electron paramagnetic resonance (EPR) spectroscopy and UV spectrophotometry. A computational approach was also used to investigate their potential primary mechanism of antioxidant action, as well as to rationalize the effect of functionalization on the nitrones reactivity toward DPPH, chosen as model radical in this study. Further insights were also gathered by exploring the nitrone electrochemical properties via cyclic voltammetry and by studying their kinetic behavior by means of EPR spectroscopy. Results showed that the introduction of an electron-withdrawing group in the phenyl moiety in the para position significantly increased the antioxidant capacity of benzoxazinic nitrones both in cell and cell-free systems. From the mechanistic point of view, the calculated results closely matched the experimental findings, strongly suggesting that the H-atom transfer (HAT) is likely to be the primary mechanism in the DPPH quenching.

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Phytochemical Fingerprinting and In Vitro Antimicrobial and Antioxidant Activity of the Aerial Parts of Thymus marschallianus Willd. and Thymus seravschanicus Klokov Growing Widely in Southern Kazakhstan

Molecules ◽

10.3390/molecules26113193 ◽

2021 ◽

Vol 26 (11) ◽

pp. 3193

Author(s):

Bagda Sagynaikyzy Zhumakanova ◽

Izabela Korona-Głowniak ◽

Krystyna Skalicka-Woźniak ◽

Agnieszka Ludwiczuk ◽

Tomasz Baj ◽

...

Keyword(s):

Antioxidant Activity ◽

Protocatechuic Acid ◽

Antioxidant Activities ◽

Methyl Esters ◽

Bactericidal Effect ◽

Ethyl Esters ◽

Volatile Fraction ◽

Aerial Parts ◽

Antimicrobial And Antioxidant Activity

The chemical composition of the hydroethanolic extracts (60% v/v) from the aerial parts of Thymus marschallianus Willd (TM) and Thymus seravschanicus Klokov (TS) from Southern Kazakhstan flora was analyzed together with their hexane fractions. Determination of antibacterial, antifungal and antioxidant activities of both extracts was also performed. RP-HPLC/PDA and HPLC/ESI-QTOF-MS showed that there were some differences between the composition of both extracts. The most characteristic components of TM were rosmarinic acid, protocatechuic acid, luteolin 7-O-glucoside, and apigenin 7-O-glucuronide, while protocatechuic acid, luteolin 7-O-glucoside, luteolin 7-O-glucuronide, and eriodictyol predominated in TS. The content of polyplenols was higher in TS than in TM. The GC-MS analysis of the volatile fraction of both examined extracts revealed the presence of thymol and carvacrol. Additionally, sesquiterpenoids, fatty acids, and their ethyl esters were found in TM, and fatty acid methyl esters in TS. The antioxidant activity of both extracts was similar. The antibacterial activity of TS extract was somewhat higher than TM, while antifungal activity was the same. TS extract was the most active against Helicobacter pylori ATCC 43504 with MIC (minimal inhibitory concentration) = 0.625 mg/mL, exerting a bactericidal effect. The obtained data provide novel information about the phytochemistry of both thyme species and suggest new potential application of TS as a source of bioactive compounds, especially with anti-H. pylori activity.

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