scholarly journals Synthesis and Antioxidative Activity of Piperine Derivatives Containing Phenolic Hydroxyl

2020 ◽  
Vol 2020 ◽  
pp. 1-9
Author(s):  
Bei Qin ◽  
Kuan Yang ◽  
Ruijun Cao
Keyword(s):  
Free Radical ◽  
Antioxidant Enzyme ◽  
Antioxidant Activities ◽  
Parent Compound ◽  
Radical Scavenging ◽  
Phenolic Hydroxyl ◽  
Hydroxyl Group ◽  
Hydroxyl Groups ◽  
Antioxidant Enzyme System ◽  
Hemoglobin Oxidation

Piperine was used in this study in its raw form, and different steps, such as amide hydrolysis and amidation, were used to synthesize piperine derivatives containing a phenolic hydroxyl group. DPPH and ABTS free radical scavenging assays were used to assess piperine derivative antioxidant activities. We constructed an AAPH oxidative stress erythrocyte model to study the effect of piperine derivatives on the hemolysis rate of oxidatively damaged erythrocytes as well as the hemoglobin oxidation rate. This AAPH model was also used to determine piperine derivative effects on antioxidant enzyme activity and malondialdehyde (MDA) content. Results showed that spectroscopic methods could synthesize and identify piperine derivatives containing phenolic hydroxyl groups (H-1∼H-3). Moreover, DPPH and ABTS assay results showed that piperine derivative free radical clearance rates were higher compared with the parent compound. Additionally, piperine derivatives (H-1∼H-3) were found to provide protection to AAPH oxidatively damaged erythrocytes in their ability to inhibit AAPH-induced erythrocyte lysis, while hemoglobin oxidation was higher compared with the parent compound. Piperine derivatives may protect intracellular glutathione peroxidase (GSH-Px) antioxidant enzyme system activities, safeguarding against oxidative damage. This study synthesized novel piperine derivatives for use as potential antioxidant agent candidates.

Structure-activity relationships of anti-tyrosinase and antioxidant activities of cinnamic acid and its derivatives

2021 ◽  
Author(s):  
Jianmin Chen ◽  
Mengnan Ran ◽  
Meixia Wang ◽  
Xinying Liu ◽  
Siwan Liu ◽  
...  
Keyword(s):  
Cinnamic Acid ◽  
Phenyl Ring ◽  
Antioxidant Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Hydroxyl Group ◽  
Hydroxyl Groups ◽  
Structure Activity Relationships ◽  
Structure Activity ◽  
Ic50 Value

Abstract The related structure-activity relationships (SARs) of cinnamic acid and its derivates have not been studied in details yet. Herein, anti-tyrosinase and antioxidant activities of 18 compounds were evaluated. The results demonstrated that the substituents on the phenyl ring of cinnamic acid led to the enhancement of the inhibition on monophenolase and the weakening of the inhibition on diphenolase. Among these tested compounds, 9 was firstly discovered as a tyrosinase inhibitor in a reversible competitive manner with IC50 value of 68.6 ± 4.2 μM. Docking results demonstrated 9 located into the catalytic center of tyrosinase. Antioxidant assay indicated that only one hydroxyl group on the phenyl ring was not enough to possess the radical scavenging activity, and the number of hydroxyl groups may be more important. This study will be helpful for development of new cinnamic acid derivates as tyrosinase inhibitors and antioxidants with higher efficacy.

Acetylcholinesterase Inhibitory Potential and Antioxidant Activities of Five Cultivars of Rosa Damascena Mill. From Isparta, Turkey

2020 ◽  
Vol 18 (4) ◽  
pp. 354-359
Author(s):  
Shirin Tarbiat ◽  
Azize Simay Türütoğlu ◽  
Merve Ekingen
Keyword(s):  
Alzheimer’S Disease ◽  
Alzheimer's Disease ◽  
Free Radical ◽  
Neurodegenerative Disorder ◽  
Antioxidant Activities ◽  
Radical Scavenging ◽  
Acetylcholinesterase Activity ◽  
Rosa Damascena ◽  
Free Radical Damage

Alzheimer's disease is a neurodegenerative disorder characterized by memory loss and impairment of language. Alzheimer's disease is strongly associated with oxidative stress and impairment in the cholinergic pathway, which results in decreased levels of acetylcholine in certain areas of the brain. Hence, inhibition of acetylcholinesterase activity has been recognized as an acceptable treatment against Alzheimer's disease. Nature provides an array of bioactive compounds, which may protect against free radical damage and inhibit acetylcholinesterase activity. This study compares the in vitro antioxidant and anticholinesterase activities of hydroalcoholic extracts of five cultivars of Rosa Damascena Mill. petals (R. damascena 'Bulgarica', R. damascena 'Faik', R. damascena 'Iranica', R. damascena 'Complex-635' and R. damascena 'Complex-637') from Isparta, Turkey. The antioxidant activities of the hydroalcoholic extracts were tested for ferric ion reduction and DPPH radical scavenging activities. The anti-acetylcholinesterase activity was also evaluated. All rose cultivars showed a high potency for scavenging free radical and inhibiting acetylcholinesterase activity. There was a significant correlation between antioxidant and acetylcholinesterase inhibitory activity. Among cultivars, Complex-635 showed the highest inhibitory effect with an IC50 value of 3.92 µg/mL. Our results suggest that all these extracts may have the potential to treat Alzheimer's disease with Complex-635 showing more promise.

Study of antioxidant potential in leaves, stems, nuts of Juglans regia L.

2012 ◽  
Vol 1 (10) ◽  
pp. 79 ◽  
Author(s):  
G. Raja* ◽  
Ivvala Anand Shaker ◽  
Inampudi Sailaja ◽  
R. Swaminathan ◽  
S. Saleem Basha ◽  
...  
Keyword(s):  
Free Radicals ◽  
Free Radical ◽  
Antioxidant Activities ◽  
Radical Scavenging Activity ◽  
Juglans Regia ◽  
Radical Scavenging ◽  
Antioxidant Compounds ◽  
Free Radical Damage ◽  
Radical Damage

Natural antioxidants can protect the human body from free radicals and retard the progress of many chronic diseases as well as lipid oxidative rancidity in foods. The role of antioxidants has protected effect against free radical damage that may cause many diseases including cancer. Primary sources of naturally occurring antioxidants are known as whole grains, fruits, and vegetables. Several studies suggest that regular consumption of nuts, mostly walnuts, may have beneficial effects against oxidative stress mediated diseases such as cardiovascular disease and cancer. The role of antioxidants has attracted much interest with respect to their protective effect against free radical damage that may cause many diseases including cancer. Juglans regia L. (walnut) contains antioxidant compounds, which are thought to contribute to their biological properties. Polyphenols, flavonoids and flavonols concentrations and antioxidant activity of Leaves, Stems and Nuts extract of Juglans regia L. as evaluated using DPPH, ABTS, Nitric acid, hydroxyl and superoxide radical scavenging activity, lipid peroxidation and total oxidation activity were determined. The antioxidant activities of Leaves, Stems and Nuts extract of Juglans regia L. were concentration dependent in different experimental models and it was observed that free radicals were scavenged by the test compounds in all the models.

scholarly journals Enhancement of Antioxidant and Hydrophobic Properties of Alginate via Aromatic Derivatization: Preparation, Characterization, and Evaluation

Polymers ◽  
2021 ◽  
Vol 13 (15) ◽  
pp. 2575
Author(s):  
Smaher M. Elbayomi ◽  
Haili Wang ◽  
Tamer M. Tamer ◽  
Yezi You
Keyword(s):  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Hydroxyl Group ◽  
Hydroxyl Groups ◽  
Gravimetric Analysis ◽  
Scanning Calorimetry ◽  
Benzoyl Group ◽  
Antioxidant Evaluation ◽  
Thermo Stability

The preparation of bioactive polymeric molecules requires the attention of scientists as it has a potential function in biomedical applications. In the current study, functional substitution of alginate with a benzoyl group was prepared via coupling its hydroxyl group with benzoyl chloride. Fourier transform infrared spectroscopy indicated the characteristic peaks of aromatic C=C in alginate derivative at 1431 cm−1. HNMR analysis demonstrated the aromatic protons at 7.5 ppm assigned to benzoyl groups attached to alginate hydroxyl groups. Wetting analysis showed a decrease in hydrophilicity in the new alginate derivative. Differential scanning calorimetry and thermal gravimetric analysis showed that the designed aromatic alginate derivative demonstrated higher thermo-stability than alginates. The aromatic alginate derivative displayed high anti-inflammatory properties compared to alginate. Finally, the in vitro antioxidant evaluation of the aromatic alginate derivative showed a significant increase in free radical scavenging activity compared to neat alginate against DPPH (2,2-diphenyll-picrylhydrazyl) and ABTS free radicals. The obtained results proposed that the new alginate derivative could be employed for gene and drug delivery applications.

scholarly journals Characterization of Phytoconstituents from Alcoholic Extracts of Four Woody Species and Their Potential Uses for Management of Six Fusarium oxysporum Isolates Identified from Some Plant Hosts

Plants ◽  
2021 ◽  
Vol 10 (7) ◽  
pp. 1325
Author(s):  
Mohamed Z. M. Salem ◽  
Abeer A. Mohamed ◽  
Hayssam M. Ali ◽  
Dunia A. Al Al Farraj
Keyword(s):  
Antioxidant Activity ◽  
Free Radical ◽  
Benzoic Acid ◽  
Fusarium Oxysporum ◽  
Leaf Extract ◽  
Antioxidant Activities ◽  
Radical Scavenging ◽  
Bark Extract ◽  
Leaf Extracts ◽  
Conium Maculatum

Background: Trees are good sources of bioactive compounds as antifungal and antioxidant activities. Methods: Management of six molecularly identified Fusarium oxysporum isolates (F. oxy 1, F. oxy 2, F. oxy 3, F. oxy 4, F. oxy 5 and F. oxy 6, under the accession numbers MW854648, MW854649, MW854650, MW854651, and MW854652, respectively) was assayed using four extracts from Conium maculatum leaves, Acacia saligna bark, Schinus terebinthifolius wood and Ficus eriobotryoides leaves. All the extracts were analyzed using HPLC-VWD for phenolic and flavonoid compounds and the antioxidant activity was evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging and β-carotene-linoleic acid (BCB) bleaching assays. Results: In mg/kg extract, the highest amounts of polyphenolic compounds p-hydroxy benzoic, benzoic, gallic, and rosmarinic acids, with 444.37, 342.16, 311.32 and 117.87, respectively, were observed in C. maculatum leaf extract; gallic and benzoic acids with 2551.02, 1580.32, respectively, in A. saligna bark extract; quinol, naringenin, rutin, catechol, and benzoic acid with 2530.22, 1224.904, 798.29, 732.28, and 697.73, respectively, in S. terebinthifolius wood extract; and rutin, o-coumaric acid, p-hydroxy benzoic acid, resveratrol, and rosmarinic acid with 9168.03, 2016.93, 1009.20, 1156.99, and 574.907, respectively, in F. eriobotryoides leaf extract. At the extract concentration of 1250 mg/L, the antifungal activity against the growth of F. oxysporum strains showed that A. saligna bark followed by C. maculatum leaf extracts had the highest inhibition percentage of fungal growth (IPFG%) against F. oxy 1 with 80% and 79.5%, F. oxy 2 with 86.44% and 78.9%, F. oxy 3 with 86.4% and 84.2%, F. oxy 4 with 84.2, and 82.1%, F. oxy 5 with 88.4% and 86.9%, and F. oxy 6 with 88.9, and 87.1%, respectively. For the antioxidant activity, ethanolic extract from C. maculatum leaves showed the lowest concentration that inhibited 50% of DPPH free radical (3.4 μg/mL). Additionally, the same extract observed the lowest concentration (4.5 μg/mL) that inhibited BCB bleaching. Conclusions: Extracts from A. saligna bark and C. maculatum leaves are considered potential candidates against the growth of F. oxysporum isolates—a wilt pathogen—and C. maculatum leaf as a potent antioxidant agent.

Synthesis and Biological Activities of Hydroxytyrosol Ester Derivatives

2020 ◽  
Vol 42 (1) ◽  
pp. 109-109
Author(s):  
Hao Zang Hao Zang ◽  
Qian Xu Qian Xu ◽  
Luyun Zhang Luyun Zhang ◽  
Guangqing Xia Guangqing Xia ◽  
Jiaming Sun and Junyi Zhu Jiaming Sun and Junyi Zhu
Keyword(s):  
Ascorbic Acid ◽  
Antioxidant Activities ◽  
Biological Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Acetylcholinesterase Inhibition ◽  
Hydroxyl Group ◽  
Scavenging Activity ◽  
Antioxidant Power ◽  
Better Than

A series of hydroxytyrosol (HT) derivatives were synthesized by modification of alcohol hydroxyl group of HT, twenty-five target compounds were obtained and characterized by NMR and HRMS. The antioxidant activities of those compounds were evaluated in three different assays. Except 3e and 3y, all other compounds demonstrated significant 2,2and#39;-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) free radical cation scavenging activity ranging from IC50 3.4 to 24.4 μM, which were more potent than L-ascorbic acid (IC50=24.8 μM). Compounds 3b-3d, 3f-3k, 3m-3x were better than Trolox (18.3 M). Moreover, the ferric reducing antioxidant power (FRAP) of all compounds were discovered to be more potent than L-ascorbic acid (40.7 mmol/g), except 3e, all other compounds (141.5-202.1 mmol/g) were better than Trolox (94.7 mmol/g). Compounds 3a-3d, 3f-3j, 3l-3m, 3o, 3q, 3t, 3v-3y exhibited more potent hydroxyl radical scavenging activity (IC50=245.1-475.1 M) than L-ascorbic acid (554.4 M) and Trolox (500.4 M). Compounds 3q, 3t and 3y exhibited more potent -Glucosidase inhibition activity (39.1-52.4 M) than Acarbose (60.9 M). Compounds 3a, 3d, 3f-3m, 3s-3t, 3v-3y showed some acetylcholinesterase inhibition activities, compounds 3a, 3d, 3f-3j, 3l-3m, 3o-3p, 3s-3t, 3w showed some butyrylcholinesterase inhibition activities.

scholarly journals Cytotoxicity and Antioxidant Effects of Celastrus hindsii Benth. Leaf Extract

2020 ◽  
Vol 36 (1) ◽  
Author(s):  
Bui Thi Thanh Duyen ◽  
Vu Manh Hung ◽  
Bui Thanh Tung
Keyword(s):  
Free Radical ◽  
Cancer Cells ◽  
Leaf Extract ◽  
Antioxidant Activities ◽  
Publishing House ◽  
Radical Scavenging ◽  
Antioxidant Effect ◽  
Ic50 Value ◽  
Etoac Fraction ◽  
Antioxidant Effects

Celastrus hindsii Benth et Hook. is known as a herbal medicine for the treatment of cancer. In this study we evaluated the cytotoxic and antioxidant effects of Celastrus hindsii Benth et Hook. leaf extract. Samples of Celastrus hindsii were extracted with 90 % ethanol and subsequently fractionated with n-hexane, ethyl acetate (EtOAc) and n-butanol (n-BuOH) solvents. To evaluate the cytotoxic effect, we performed MTT (3- (4,5 dimethylthiazol-2 - yl) - 2,5 - diphenyltetrazolium) assay on the three cell lines human liver Hep G2 (HB - 8065TM), lung LU-1 (HTB - 57TM), breast MCF-7 (HTB - 22TM).  The antioxidant effect was evaluated by screening DPPH (2,2-diphenyl-1-picryhydrazyl) free radical assay. The results showed that the EtOAc fraction had the strongest cytoxicity effects on liver cancer cells and lung cancer cells with an IC50 value of 33,7 ± 1,5 mg/mL and 13,0 ± 0,5 mg/mL. The BuOH fraction showed a weaker effect on lung cancer cells with IC50 value of 64,0 ± 2,2 mg/mL. The antioxidant results indicated that the EtOAc fraction had the best antioxidant effect with IC50  value of 46,9 ± 2,5 µg/mL. The EtOH total extract also has strong antioxidant activity with IC50 value of 48,5 ± 2,3 µg/mL. Our study showed that Celastrus hindsii leaf extract has the strong cytotoxicity and antioxidant activities. Keywords Celastrus hindsii Benth et Hook., cytotoxicity, MTT, antioxidant, DPPH. References [1] Ministry of health, General oncology. 2009: Vietnam Education Publishing House Limited Company, 9-10.[2] N.V. Tuyen, Pharmaceutical chemistry curriculum, 2014, Science and Technics Publishing House. 222-223.[3] V.V. Chi. Dictionary of Vietnamese medicinal plants. Medical Publishing House 1 (2012).[4] V. Gan, G. Chen, W. Zhang, J. Zhou . Oleanen induces apoptosis of cervical cancer cells by up-regulation of Bim. International Journal of Gynecologic Cancer 22(1) (2012) 38.[5] Y.H. Kuo, L.M.Y. Kuo. Antitumour and anti-AIDS triterpenes from Celastrus hindsii. Phytochemistry 44(7) (1997) 1275.[6] T. Mosmann, Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays 65(1-2) (1983) 55.[7] P. Mahakunakorn, M. Tohda, Y. Murakami, K. Matsumoto, H.J.B. Watanabe, P. Bulletin, Antioxidant and free radical-scavenging activity of Choto-san and its related constituents 27(1) (2004) 38.[8] P.T. Thuong, M.K. Na, N.H. Dang, T.M. Hung, P.T. Ky, T.V. Thanh, et al. Antioxidant activities of Vietnamese medicinal plants 12(1) (2006) 29.[9] X.Q. Hu, W. Han, Z.Z. Han, Q.X. Li, X.K. Xu, P. Fu, et al. A new macrocyclic lactone and a new quinoflavan from Celastrus hindsii. Phytochemistry letters 7 (2014) 169.[10] A.C. Spivey, M. Weston, Woodhead SJCSR. Celastraceae sesquiterpenoids: biological activity and synthesis 31(1) (2002) 43.[11] T.L. Ngoc, Technology. Separation process of rosmarinic acid and their derivatives from Celastrus hindsii benth leaves. Vietnam Journal of Science 54(2C) (2016) 380.[12] F.R. Mowsumi, A. Rahaman, N.C. Sarker, B.K. Choudhury, Hossain SJWJPPS. In vitro relative free radical scavenging effects of Calocybe indica (milky oyster) and Pleurotus djamor (pink oyster). 4(07) (2015).[13] T.D. Viet, T.D. Xuan, T.M. Van, Y. Andriana, R. Rayee, H.D. Tran. Comprehensive Fractionation of Antioxidants and GC-MS and ESI-MS Fingerprints of Celastrus hindsii Leaves. Medicines 6(2) (2019) 64.[14] T.N. Ly, M. Shimoyamada, Yamauchi RJJoa, chemistry f. Isolation and characterization of rosmarinic acid oligomers in Celastrus hindsii Benth leaves and their antioxidative activity 54(11) (2006) 3786.    

scholarly journals Design, Synthesis, Antimicrobial, and Antioxidant Activities of Novel-{4, 5-(substituted diphenyl)-4H-1, 2, 4-triazol-3-ylthio} Acetyl Chloride

2017 ◽  
Vol 15 (2) ◽  
pp. 157-167
Author(s):  
Prabhakar Kumar VERMA ◽  
Mukesh KUMAR ◽  
Nelam MALIK ◽  
Priyanka DHIMAN ◽  
Anurag KHATAHAR
Keyword(s):  
Free Radical ◽  
Acetyl Chloride ◽  
Antioxidant Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Free Radical Scavenging ◽  
Biologically Active ◽  
Free Radical Scavenging Activity ◽  
Scavenging Activity ◽  
Standard Drug

A series of 20 new biologically active derivatives of 2-{4, 5-(substituted diphenyl)-4H-1,2,4-triazol-3-ylthio}acetyl chloride has been synthesized, with the aim to investigate antimicrobial, free radical scavenging activity. All the synthesized compounds were characterized by spectroscopic data and elemental analysis. The final compounds were tested for antibacterial activity against Gram-positive bacteria: Staphylococcus aureus MTCC 3160, Bacillus subtilis MTCC 441; Gram-negative bacteria: Escherichia coli MTCC 443, and, for antifungal activity, against Candida albicans MTCC 227 and Aspergillus niger MTCC 281, taking ciprofloxacin as antibacterial and fluconazole as antifungal standard drugs. Compound 7a6 was found to be the most effective antibacterial (MIC = 3.12 µg/ml), and compounds 7a2 and 7d1 (MIC = 3.12 and 6.25 µg/ml) had the most effective antifungal effects on the selected strains, as compared to the standard drugs. The results of antioxidant studies revealed that compound 7b1 was found to be most active antioxidant, with 40.4±0.687 µg/ml, and compounds 7b3, 7d7, and 7d4 also showed promising free radical scavenging activity, as compared with the standard drug ascorbic acid.

Methylation of Phenolic Hydroxyl Group and Demethylation of Anisoles

2009 ◽  
Vol 2009 (4) ◽  
pp. 229-230 ◽  
Author(s):  
Nobuhiro Sato ◽  
Hiroyuki Endo
Keyword(s):  
Microwave Heating ◽  
Room Temperature ◽  
Reverse Reaction ◽  
Phenolic Hydroxyl ◽  
Hydroxyl Group ◽  
Hydroxyl Groups ◽  
Phenolic Hydroxyl Groups ◽  
Phenyl Ethers ◽  
Methyl Phenyl

A mild methylation of phenolic hydroxyl groups with iodomethane was enabled in the presence of sodium bis(trimethylsilyl)amide at room temperature. The reverse reaction, namely demethylation of methyl phenyl ethers, was easily achieved by microwave heating with neat iodotrimethylsilane.

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