Synthesis of dimeric phenol derivatives and determination of in vitro antioxidant and radical scavenging activities

In this study, di(2,6-dimethylphenol) (Di-DMP), di(2,6-diisopropylphenol) (Di-DIP, dipropofol) and di(2,6-di-t-butylphenol) (Di-DTP) were synthesized by the reaction of monomeric phenol derivatives with catalytic CuCl(OH). TMEDA and Na₂S₂O₄. Their antioxidant capacity and radical scavenging activity were examined using different in vitro methodologies such as 1,1-diphenyl-2-picryl-hydrazyl (DPPH·) free radical scavenging, 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical scavenging activity, total antioxidant activity by ferric thiocyanate, total reducing power by potassium ferricyanide reduction method, superoxide anion radical scavenging, hydrogen peroxide scavenging and ferrous ions chelating activities.     

Synthesis, antioxidant and toxicological study of novel pyrimido quinoline derivatives from 4-hydroxy-3-acyl quinolin-2-one

A series of novel pyrimido and other fused quinoline derivatives like 4-methyl pyrimido [5,4-c]quinoline-2,5(1H,6H)-dione (4a), 4-methyl-2-thioxo-1,2-dihydropyrimido [5,4-c]quinoline-5(6H)-one (4b), 2-amino-4-methyl-1,2-dihydropyrimido [5,4-c]quinolin-5(6H)-one (4c), 3-methylisoxazolo [4,5-c]quinolin-4(5H)-one (4d), 3-methyl-1H-pyrazolo [4,3-c]quinoline-4(5H)-one (5e), 5-methyl-1H-[1,2,4] triazepino [6,5-c]quinoline-2,6(3H,7H)-dione (5f), 5-methyl-2-thioxo-2,3-dihydro-1H-[1,2,4]triazepino [6,5-c]quinolin-6(7H)-one (5 g) were synthesized regioselectively from 4-hydroxy-3-acyl quinolin-2-one 3. They were screened for their in vitro antioxidant activities against radical scavenging capacity using DPPH(), Trolox equivalent antioxidant capacity (TEAC), total antioxidant activity by FRAP, superoxide radical (O(2)(°-)) scavenging activity, metal chelating activity and nitric oxide scavenging activity. Among the compounds screened, 4c and 5 g exhibited significant antioxidant activities.     

Antioxidant and radical scavenging properties of curcumin

Curcumin (diferuoyl methane) is a phenolic compound and a major component of Curcuma longa L. In the present paper, we determined the antioxidant activity of curcumin by employing various in vitro antioxidant assays such as 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH*) scavenging, 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical scavenging activity, N,N-dimethyl-p-phenylenediamine dihydrochloride (DMPD) radical scavenging activity, total antioxidant activity determination by ferric thiocyanate, total reducing ability determination by the Fe(3+)-Fe(2+) transformation method, superoxide anion radical scavenging by the riboflavin/methionine/illuminate system, hydrogen peroxide scavenging and ferrous ions (Fe(2+)) chelating activities. Curcumin inhibited 97.3% lipid peroxidation of linoleic acid emulsion at 15 microg/mL concentration (20 mM). On the other hand, butylated hydroxyanisole (BHA, 123 mM), butylated hydroxytoluene (BHT, 102 mM), alpha-tocopherol (51 mM) and trolox (90 mM) as standard antioxidants indicated inhibition of 95.4, 99.7, 84.6 and 95.6% on peroxidation of linoleic acid emulsion at 45 microg/mL concentration, respectively. In addition, curcumin had an effective DPPH* scavenging, ABTS*(+) scavenging, DMPD*(+) scavenging, superoxide anion radical scavenging, hydrogen peroxide scavenging, ferric ions (Fe(3+)) reducing power and ferrous ions (Fe(2+)) chelating activities. Also, BHA, BHT, alpha-tocopherol and trolox, were used as the reference antioxidant and radical scavenger compounds. According to the present study, curcumin can be used in the pharmacological and food industry because of these properties.     

Comparison of in vitro antioxidant and antiradical activities of L-tyrosine and L-Dopa

Summary. Phenolic compounds are interesting because of their antioxidant properties. In the present study, the antioxidant properties of L-tyrosine as a monophenolic and L-Dopa as a diphenolic amino acid were investigated by using different antioxidant assays: (i) 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH^•) scavenging; (ii) 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation decolorization assay; (iii) total antioxidant activity by ferric thiocyanate method; (iv) ferric ions (Fe³⁺) reducing power; (v) superoxide anion radical (O₂ ^•−) scavenging; (vi) hydrogen peroxide (H₂O₂) scavenging, and (vii) ferrous ions (Fe²⁺) chelating activities. Butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), α-tocopherol and trolox, a water-soluble analogue of tocopherol, were used as the reference antioxidant compounds. At the same concentration (20 μg/mL), L-tyrosine and L-Dopa showed 30.6 and 67.9% inhibition of lipid peroxidation of linoleic acid emulsion, respectively. On the other hand, BHA, BHT, α-tocopherol and trolox indicated inhibitions of 74.4, 71.2, 54.7 and 20.1% on the peroxidation of linoleic acid emulsion, respectively, at the above-mentioned concentration. In addition, L-tyrosine and L-Dopa had an effect on DPPH radical scavenging, ABTS radical scavenging, superoxide anion radical scavenging, H₂O₂ scavenging, total ferric ions reducing power and metal chelating on ferrous ions activities.     

In vitro antioxidant activity of silymarin

Silymarin, a known standardized extract obtained from seeds of Silybum marianum is widely used in treatment of several diseases of varying origin. In the present paper, we clarified the antioxidant activity of silymarin by employing various in vitro antioxidant assay such as 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH(.)) scavenging, 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical scavenging activity, total antioxidant activity determination by ferric thiocyanate, total reducing ability determination by Fe3+ - Fe2+ transformation method and Cuprac assay, superoxide anion radical scavenging by riboflavin/methionine/illuminate system, hydrogen peroxide scavenging and ferrous ions (Fe2+) chelating activities. Silymarin inhibited 82.7% lipid peroxidation of linoleic acid emulsion at 30 microg/mL concentration; butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), alpha-tocopherol and trolox indicated inhibition of 83.3, 82.1, 68.1 and 81.3% on peroxidation of linoleic acid emulsion at the same concentration, respectively. In addition, silymarin had an effective DPPH(.) scavenging, ABTS(.)+ scavenging, superoxide anion radical scavenging, hydrogen peroxide scavenging, ferric ions (Fe3+) reducing power by Fe3+-Fe2+ transformation, cupric ions (Cu2+) reducing ability by Cuprac method, and ferrous ions (Fe2+) chelating activities. Also, BHA, BHT, alpha-tocopherol and trolox, were used as the reference antioxidant and radical scavenger compounds. Moreover, this study, which clarifies antioxidant mechanism of silymarin, brings new information on the antioxidant properties of silymarin. According to the present study, silymarin had effective in vitro antioxidant and radical scavenging activity. It could be used in the pharmacological and food industry because of its antioxidant properties.     

Synthesis,antielastase, antioxidant and radical scavenging activities of 4-(aza substituted) methylene substituted dihydroxy coumarines

A series of some 4-(aza substituted) methylene substituted dihydroxy coumarines were evaluated for their antioxidant and antielastase activities. Different in vitro methodologies such as total reducing power, 1,1-diphenyl-2-picryl-hydrazil (DPPH·) free radical scavenging, ABTS radical scavenging activity were used as antioxidant activity. All the tested compounds exhibited potent free radical scavenging ability and antielastase activites.     

In vitro antioxidant activity of silymarin

Silymarin, a known standardized extract obtained from seeds of Silybum marianum is widely used in treatment of several diseases of varying origin. In the present paper, we clarified the antioxidant activity of silymarin by employing various in vitro antioxidant assay such as 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH·) scavenging, 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical scavenging activity, total antioxidant activity determination by ferric thiocyanate, total reducing ability determination by Fe³⁺ ? Fe²⁺ transformation method and Cuprac assay, superoxide anion radical scavenging by riboflavin/methionine/illuminate system, hydrogen peroxide scavenging and ferrous ions (Fe²⁺) chelating activities. Silymarin inhibited 82.7% lipid peroxidation of linoleic acid emulsion at 30 μg/mL concentration; butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), α-tocopherol and trolox indicated inhibition of 83.3, 82.1, 68.1 and 81.3% on peroxidation of linoleic acid emulsion at the same concentration, respectively. In addition, silymarin had an effective DPPH· scavenging, ABTS^√+ scavenging, superoxide anion radical scavenging, hydrogen peroxide scavenging, ferric ions (Fe³⁺) reducing power by Fe³⁺ ? Fe²⁺ transformation, cupric ions (Cu²⁺) reducing ability by Cuprac method, and ferrous ions (Fe²⁺) chelating activities. Also, BHA, BHT, α-tocopherol and trolox, were used as the reference antioxidant and radical scavenger compounds. Moreover, this study, which clarifies antioxidant mechanism of silymarin, brings new information on the antioxidant properties of silymarin. According to the present study, silymarin had effective in vitro antioxidant and radical scavenging activity. It could be used in the pharmacological and food industry because of its antioxidant properties.     

Free radical and reactive oxygen species scavenging activities of the extracts from seahorse, Hippocampus kuda Bleeler

Seahorse, Hippocampus kuda (SH) a marine teleost fish, is well known not only for its special medicinal composition and used as one of the most famous and expensive materials of traditional Chinese medicine. It was extracted with water (SHW), methanol (SHM), and ethanol (SHE), respectively and evaluated by various antioxidant assays. The including reducing power, total antioxidant, DPPH radical scavenging, hydroxyl radical scavenging, superoxide anion radical scavenging, alkyl radical scavenging, and protective effect on DNA damage caused by hydroxyl radicals generated. Further, the ROS level was detected using a fluorescence probe, 2′,7′-dichlorofluorescin diacetate (DCFH-DA), which could be converted to highly fluorescent dichlorofluorescein (DCF) with the presence of intracellular ROS on mouse macrophages, RAW264.7 cell and inhibited myeloperoxidase (MPO) activity in human myeloid, HL60 cells, respectively. Those various antioxidant activities were compared to standard antioxidants such as α-tocopherol. Among SHM exhibited the highest antioxidant activity in linoleic acid system, effective reducing power, DPPH radical scavenging, hydroxyl radical scavenging, superoxide radical scavenging, alkyl radical scavenging, inhibitory intracellular ROS, and inhibited MPO activity. Furthermore, MTT assay showed no cytotoxicity on mouse macrophages cell (RAW264.7) and human cell lines (MRC-5, HL60, U937). This antioxidant property depends on concentration and increasing with increased amount of extracts. The results obtained in the present study indicated that the see horse (Hippocampus kuda Bleeker) is a potential source of natural antioxidant.     

Antioxidant and antiradical activities of L-carnitine

L-carnitine plays an important regulatory role in the mitochondrial transport of long-chain free fatty acids. In this study, the antioxidant activity of L-carnitine was investigated as in vitro. The antioxidant properties of the L-carnitine were evaluated by using different antioxidant assays such as 1, 1-diphenyl-2-picryl-hydrazyl free radical (DPPH.) scavenging, total antioxidant activity, reducing power, superoxide anion radical scavenging, hydrogen peroxide scavenging and metal chelating activities. Total antioxidant activity was measured according to ferric thiocyanate method. alpha-tocopherol and trolox, a water-soluble analogue of tocopherol, were used as the reference antioxidant compounds. At the concentrations of 15, 30 and 45 microg/mL, l-carnitine showed 94.6%, 95.4% and 97.1% inhibition on lipid peroxidation of linoleic acid emulsion, respectively. On the other hand, 45 microg/mL of standard antioxidant such as alpha-tocopherol and trolox indicated an inhibition of 88.8% and 86.2% on peroxidation of linoleic acid emulsion, respectively. In addition, L-carnitine had an effective DPPH. scavenging, superoxide anion radical scavenging, hydrogen peroxide scavenging, total reducing power and metal chelating on ferrous ions activities. Also, those various antioxidant activities were compared to alpha-tocopherol and trolox as references antioxidants.     

The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids

Phloretin is a dihydrochalcone flavonoid that displays a potent antioxidant activity in peroxynitrite scavenging and the inhibition of lipid peroxidation. Comparison with structurally related compounds revealed that the antioxidant pharmacophore of phloretin is 2,6-dihydroxyacetophenone. The potent activity of 2,6-dihydroxyacetophenone is due to stabilisation of its radical via tautomerisation. The antioxidant pharmacophore in the dihydrochalcone phloretin, i.e., the 2,6-dihydroxyacetophenone group, is different from the antioxidant pharmacophores previously reported in flavonoids.     

印度块菌提取物抗氧化活性的研究

对印度块菌Tuber indicum子实体的提取物,包括55%乙醇粗提物(ECE)、石油醚提取物(PEF)和乙酸乙酯提取物(EAF)的清除DPPH自由基和羟基自由基能力、铁离子鳌合能力以及各提取物的总酚含量等进行了研究和测定,结果显示,3种提取物的清除自由基能力和铁离子鳌合能力具有显著差异(P0.05);ECE对DPPH自由基的清除活性最高,其EC50值为1.61g/L;EAF对羟基自由基及铁离子表现出较强的清除或螯合的能力,其EC50值分别为3.31g/L和0.70g/L;EAF的总酚含量(2.964mg GAE/g提取物)最高,其次是ECE,总酚含量为(2.618mg GAE/g提取物);PEF的清除自由基和铁离子鳌合能力较差,其总酚含量也最低(1.124mg GAE/g提取物);总酚含量与印度块菌提取物清除自由基以及鳌合铁离子的能力密切相关。     

有柄石韦醇提物抗氧化活性研究

通过DPPH自由基清除测定、还原能力、总抗氧化能力、羟自由基清除测定,评价有柄石韦Pyrrosia petiolosa醇提物的抗氧化活性。结果显示,有柄石韦醇提物清除DPPH·的IC50为75.82 μg·mL-1,清除·OH的IC50为46.30 μg·mL-1。有柄石韦醇提物清除DPPH· 的能力强于抗坏血酸,清除·OH的能力弱于抗坏血酸;同时,其还原能力和总抗氧化能力均强于抗坏血酸。该结果说明有柄石韦醇提物具有较强的抗氧化活性。     

Antioxidant activity of bisbenzylisoquinoline alkaloids from Stephania rotunda: cepharanthine and fangchinoline

In the present study, we determined the antioxidant activity of cepharanthine and fangchinoline from Stephania rotunda by performing different in vitro antioxidant assays, including 1,1-diphenyl-2-picryl-hydrazyl (DPPH) free radical scavenging, 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical scavenging, N,N- dimethyl-p-phenylenediamine dihydrochloride (DMPD) radical scavenging, superoxide anion (O₂^?–) radical scavenging, hydrogen peroxide scavenging, total antioxidant activity, reducing power, and ferrous ion (Fe²⁺) chelating activities. Cepharanthine and fangchinoline showed 94.6 and 93.3% inhibition on lipid peroxidation of linoleic acid emulsion at 30 μg/mL concentration, respectively. On the other hand, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), α-tocopherol, and trolox indicated inhibitions of 83.3, 92.2, 72.4, and 81.3% on peroxidation of linoleic acid emulsion at the same concentration (30 μg/mL), respectively. According to the results, cepharanthine and fangchinoline have effective antioxidant and radical scavenging activity.     

Screening and evaluation of antioxidant activity of some amido-carbonyl oxime derivatives and their radical scavenging activities

The antioxidant activity of some amido-carbonyl oximes containing a C=O and –NH–R adjacent to the oxime group, [Phenyl-C(=O)-C(=N-OH)-N(-H)-Phenyl(-R)] where R= H, 4-chloro, 4-methyl, 4-methoxy, 3,4-dichloro, 3,4-dimethyl, 3-chloro-4-dimethyl, 3-chloro-4-methoxy, naphthyl and an amido-carbonyl dioxime were investigated in vitro by ferric thiocyanate, total reducing power by potassium ferricyanide reduction, 1,1-diphenyl-2- picryl-hydrazyl (DPPH^·) free radical scavenging, ferrous ions chelating, superoxide anion radical scavenging and hydrogen peroxide scavenging activity assays. The results indicated that the amido-carbonyl oximes have powerful antioxidant capacity.     

荸荠皮提取物对DPPH自由基清除活性

采用70%丙酮溶液对荸荠皮中抗氧化物质进行提取,得到红棕色浸膏。通过定性及定量方法分析了荸荠皮提取物中可能存在的具有抗氧化活性的物质;采用DPPH自由基法测定了荸荠皮提取物对DPPH自由基的清除能力。结果显示,荸荠皮提取物中含有多酚类和黄酮类等化合物,其多酚含量为3.31%(w/w,以干物质计)。DPPH自由基法显示,荸荠皮提取物具有一定的清除DPPH自由基能力,其清除能力与提取物浓度之间显示出良好的剂量-效应关系。该提取物(IC50值为130.37 ppm)对DPPH自由基清除能力略低于BHT(IC50值为94.16 ppm)。     

Free radical scavenging activity,total phenolic content,total antioxidant status,and total oxidant status of endemic Thermopsis turcica

Thermopsis turcica, endemic to Turkey, is in danger of extinction. Studies on this species are very few due to the fact that it was only discovered in 1983 and grows in a small circumscribed area in Turkey. In this study, free radical scavenging activity, total phenolic content, total oxidant status (TOS), and total antioxidant status (TAS) of methanol (TTM) and acetone (TTA) extracts of T. turcica were measured spectroscopically. Free radical scavenging activity was determined according to the elimination of DPPH radicals and total phenol content was determined by the Folin–Ciocalteu reaction. Total oxidant status (TOS) and total antioxidant status (TAS) were measured with commercially available kits. Methanol and acetone extracts of T. turcica were found to have a specific radical scavenging effect. This effect was found to be related to the total phenolic content of the extracts. Since the TTA had a higher phenolic content than the methanol extract, it had a stronger radical scavenging effect. In addition, the total antioxidant capacity of the methanol extract was observed to be higher than that of its acetone counterpart. As a result, due to its antioxidative properties, T. turcica is thought to be a natural source of antioxidants.     

Egyptian propolis: 3. Antioxidant,antimicrobial activities and chemical composition of propolis from reclaimed lands

The free radical scavenging effect of two propolis samples collected from reclaimed land, Egypt as well as of vitamin C and caffeic acid in 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical system was determined. The antimicrobial (Staphylococcus aureus; Escherichia coli and Candida albicans) activity was also investigated. The results of the free radical scavenging effect of El-Saff and Ismailia propolis showed a concentration-dependent activity. The antioxidant activity was varied according to the examined material. It was obvious that caffeic acid and vitamin C showed the highest activity if compared with the propolis samples. El- Saff propolis had a higher antioxidant activity than Ismailia propolis, it showed a higher antibacterial activity against Staphylococcus aureus and a higher anti-fungal activity against Candida albicans. While the Ismailia propolis had a higher antibacterial activity against Escherichia coli, than El-Saff propolis. The chemical composition of propolis samples was investigated by GC/MS, where 75 compounds were identified, 22 being new for propolis. The Ismailia propolis was characterized by the presence of a highly significant amount of aromatic acid esters (47.3%) and triterpenoids (17.3%), while El-Saff propolis contained 3% and 1.9% respectively. The new esters belonged to 4-methoxyhydrocinnamic acid, hydroferulic acid and ferulic acid. El-Saff propolis had a very high significant amount (27%) of 2,6-bis-(pentanyloxy)-4-pentanylphenethanol, which is also a new compound for propolis.     

Radical scavenging activities of Heracleum aquilegifolium Wight (Apiaceae) fruit oils in vitro

The fruits of Heracleum aquilegifolium Wight (Apiaceae) were collected from Western Ghats of the Indian Peninsula. The essential oils were extracted by hydrodistillation. The chemical composition of the essential oils was analysed by gas chromatography and gas chromatography-mass spectrometry (GC-MS). Beta-Pinene (22.3%), 1,8-cineole (20.3%), and beta-phellandrene (12.4%) were the main components of H. aquilegifolium fruit oils. The antioxidant properties of essential oils of H. aquilegifolium were examined by different procedures namely reducing power ability, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity, nitric oxide radical scavenging activity, hydrogen peroxide scavenging activity, hydroxyl radical scavenging activity, superoxide anion scavenging activity, and metal chelating activity. The antioxidant activities were compared with those of synthetic antioxidants and standard drugs such as butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), ascorbic acid, alpha-tocopherol, curcumin, and quercetin. The study confirmed the possible antioxidant potential of essential oils tested with various in vitro antioxidant methods. The presence of monoterpenes in combination with other components in the oils could be responsible for the activity.     

Preparation and in vitro antioxidant activities of 6‐amino‐6‐deoxychitosan and its sulfonated derivatives

The 6‐amino‐6‐deoxychitosan (NC) and their 2, 6‐di‐N‐sulfonated derivatives were prepared via N‐phthaloylation, tosylation, azidation, hydrazinolysis, reduction of azide groups and N‐sulfonation, and their structures were systematically characterized by FT‐IR, 2D HSQC NMR, XRD, gel permeation chromatography (GPC), and elemental analysis. The 6‐amino‐6‐deoxychitosan showed effect in three selected antioxidant essays, including reducing power, superoxide anion radical scavenging ability, and hydroxyl radical scavenging effect. But the factors affecting each activity were different. The reducing power and the superoxide anion radical scavenging ability of NC were strong and closely related to the amino groups in the molecular chains. Both introducing N‐sulfonated groups into NC and the concentration reduction of NC and its sulfonated derivatives decreased these activities. For the superoxide anion radical, the molecular charge property was also a significant influence factor. For the hydroxyl radical, NC only showed weak scavenging activity in a special inverse concentration‐dependent manner. However, the incorporation of N‐sulfonated groups significantly improved the scavenging activity, and the more N‐sulfonated groups, the higher the concentrations, the stronger the activity was. The results could be due to the different conformations of NC and its sulfonated derivatives in aqueous solution. © 2015 Wiley Periodicals, Inc. Biopolymers 103: 539–549, 2015.     

乌鳖黑色素理化性质及其抗氧化活性研究

本试验以乌鳖肌肉为原料,采用“脱脂-酶解-酸解”三步法制备乌鳖黑色素,研究其结构特性、理化性质和抗氧化活性。采用紫外分光光度计、傅里叶红外光谱仪和元素分析仪对乌鳖肌肉黑色素结构特性进行分析,并进行了颜色检测、溶解性试验、稳定性试验、总抗氧化能力试验、羟基自由基清除能力试验、DPPH自由基清除能力试验、超氧阴离子自由基清除能力试验等理化性质和抗氧化活性检测分析。结果表明:乌鳖黑色素粉末呈黑色(L=45.04),略带红色和黄色(a=1.92,b=5.27);具有与其他黑色素相似的溶解性,溶于碱性溶液,不溶于水、有机溶剂和酸性溶液等;乌鳖黑色素在1 h内具有较强光稳定性和热稳定性;乌鳖黑色素具有较强的抗氧化能力,其中2.0 mg/mL浓度的黑色素溶液羟自由基清除率、超氧阴离子自由基清除率和DPPH自由基清除率均在40%以上。