Increase in the free radical scavenging activity of ginseng by heat-processing

To investigate whether or not the radical scavenging activity of ginseng is enhanced by heat processing, we evaluated the scavenging effects of white ginseng (WG), red ginseng (RG, steamed ginseng at 98-100 degrees C) and sun ginseng (SG, steamed ginseng at 120 degrees C) on nitric oxide, superoxide (O2-), hydroxyl (*OH) radicals and peroxynitrite (ONOO-). Heat-treated ginseng (RG and SG) showed better O2-, ONOO- and *OH-scavenging activities than WG. In particular, the radical scavenging activities of SG were stronger than those of RG. Furthermore, we evaluated the radical scavenging activities of maltol, salicylic acid, vanillic acid and p-coumaric acid, known as principal antioxidant components of ginseng, in WG, RG and SG, and also investigated their contents. Of the tested compounds, maltol, vanillic acid and p-coumaric acid exhibited ONOO(-)-scavenging activity. In addition, maltol and p-coumaric acid showed strong *OH-scavenging activity. Moreover, the content of maltol was remarkably increased in a temperature-dependent manner by heat processing, implying that maltol was closely related to the radical scavenging activity of heat-processed ginseng. These findings indicate that SG may act as a free radical scavenger and protect against damage caused by oxidative stress related with these radicals.     

Free radical scavenging activity of red ginseng aqueous extracts

This study was performed to investigate the free radical scavenging activity of Panax red ginseng C.A. Meyer aqueous extract on 1,1-dipheny-2-picrylhydrazyl (DPPH), carbon-centered radical, hydroxyl and superoxide radicals using Electron Spin Resonance (ESR) spectrometer and spin-trapping techniques. Two different Red ginseng aqueous extracts prepared by boiling water or room temperature extraction exhibited no significant difference in free radical scavenging activity. Ginseng extracts completely eliminated DPPH radical at 2 mg/ml. About 0.5 mg/ml ginseng extracts quenched 80% carbon-centered free radicals generated from 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH). Hydroxyl radical and superoxide radical were generated by UV irradiation and trapped by 5,5-dimethyl-l-pyrroline-N oxide (DMPO). Ginseng extracts scavenged 40% of hydroxyl radical at 0.1 mg/ml. Two mg/ml ginseng extracts completely scavenged superoxide radical. Ginseng extracts did not scavenge nitric oxide. The ESR data demonstrate that red ginseng aqueous extract is not a strong free radical scavenger.     

Investigations concerning the correlation of COX-1 inhibitory and hydroxyl radical scavenging activity

The aim was to study the COX-1 inhibiting efficacy in context with hydroxyl radical scavenging properties of compounds bearing a carboxylic acid and ester function, respectively. In general, the acids are more potent radical scavengers than the corresponding esters but there is no clear correlation with their COX-1 inhibiting potencies. A feasible scavenging mechanism of carboxylic acids is discussed.     

肉桂酸衍生物清除羟基自由基活性研究

目的:比较研究咖啡酸、氯原酸、连翘酯苷、阿魏酸、对-羟基香豆酸、邻-羟基香豆酸、间-羟基香豆酸、肉桂酸等中草药有效成分对HO·的清除能力.方法:利用邻菲罗啉化学发光体系.结果:咖啡酸、氯原酸、连翘酯苷、阿魏酸对HO·具有较强的清除能力,对-羟基香豆酸、邻-羟基香豆酸、间-羟基香豆酸对HO·的清除能力较弱,而肉桂酸对HO·的清除作用很小.结论:肉桂酸衍生物的酚羟基邻位有含孤对电子的杂原子取代基(-OH,-OCH3)时,清除HO·的能力可被提高;在-CHCHCOOH的对位含有酚羟基的化合物比在邻位或间位含有酚羟基化合物的活性强.     

Antioxidant activity of Hypericum androsaemum infusion: scavenging activity against superoxide radical,hydroxyl radical and hypochlorous acid

Hypericum androsaemum is a medicinal plant species containing many polyphenolic compounds, namely flavonoids and phenolic acids. Since polyphenolic compounds have high antioxidant potential, the ability of H. androsaemum infusion to act as a scavenger of reactive oxygen species (superoxide radical, hydroxyl radical and hypochlorous acid) was investigated. Superoxide radical was generated by the xanthine/xanthine oxidase and phenazine methosulphate/NADH systems. The infusion-mediated prevention of nitroblue tetrazolium reduction by the superoxide radical was used as the measured endpoint. Hydroxyl radical was generated by the Fe3+-EDTA/ascorbate Fenton system, and assayed by evaluating deoxyribose degradation using the thiobarbituric acid method. Hypochlorous acid scavenging activity was tested by measuring the inhibition of hypochlorous acid-induced 5-thio-2-nitrobenzoic acid oxidation to 5,5'-dithiobis(2-nitrobenzoic acid). The tested infusion mainly exhibited a potent scavenging effect on superoxide radicals (although a noncompetitive inhibitory effect on xanthine oxidase was also observed). The infusion also acted as a moderate scavenger of hydroxyl radicals and hypochlorous acid. A phytochemical study of the infusion was also undertaken, and nine phenolic compounds were identified.     

珠芽蓼清除羟自由基作用研究

目的为了解珠芽蓼根茎作为蝙蝠蛾幼虫食物的生理作用,研究它的提取物对羟自由基的清除能力。方法采用邻二氮菲—Fe2+氧化法检测珠芽蓼根茎的提取物对H2O2/Fe2+体系产生的羟自由基的清除作用。结果珠芽蓼根茎蒸馏水提取物和丙酮提取物均对羟自由基有清除作用,其中丙酮提取物的作用最强。结论珠芽蓼根茎具有明显的清除羟自由基作用,其活性主要来自丙酮提取物部分。     

Studies on the antioxidant activity of Lippia citriodora infusion: scavenging effect on superoxide radical,hydroxyl radical and hypochlorous acid

Lippia citriodora is an herbal species which contains several flavonoids and phenolic acids. In view of the pharmacological interest in natural phenolic compounds as antioxidants, this study examined the superoxide radical, hydroxyl radical and hypochlorous acid scavenging activities of L. citriodora infusion. Superoxide radical was generated either in an enzymatic or in a chemical system, and scavenging ability was assessed by the inhibition of nitroblue tetrazolium reduction. Hydroxyl radical was generated by the reaction of an iron-EDTA complex with H2O2 in the presence of ascorbic acid, and was assayed by evaluating deoxyribose degradation. Hypochlorous acid scavenging activity was tested by measuring the inhibition of 5-thio-2-nitrobenzoic acid oxidation. The results demonstrate that this infusion has a potent superoxide radical scavenging activity and a moderate scavenging activity of hydroxyl radical and hypochlorous acid. The chemical composition of the lyophilized infusion was also determined in an attempt to establish its relationship with the antioxidant activity found in the present study.     

The iron-binding and hydroxyl radical scavenging action of anti-inflammatory drugs

1. Hydroxyl radicals (.OH) are thought to be generated at sites of inflammation and to contribute to tissue damage. All anti-inflammatory drugs tested were able to scavenge .OH generated in free solution at almost diffusion-controlled rates (rate constants about 10(10)M-1s-1). 2. Much .OH generation in vivo occurs at specific sites, where bound metal ions (such as Fe2+) react with H2O2 to produce .OH that immediately attacks the site. Only .OH scavengers that have sufficient metal-binding ability to withdraw metal ions from this site can protect against site-specific damage. 3. All anti-inflammatory drugs tested were able to protect against site-specific damage by .OH in a simple model system in vitro. Penicillamine, diclofenac sodium, piroxicam, azathioprine, primaquine, chloroquine and hydroxychloroquine were especially effective. 4. The ability of an anti-inflammatory drug to protect against .OH formation in vivo depends not only on its rate constant for reaction with .OH, but also on its metal-binding ability and on the geometry and redox potential of any metal complex formed.     

Alaternin and emodin with hydroxyl radical inhibitory and/or scavenging activities and hepatoprotective activity on tacrine-induced cytotoxicity in HepG2 cells

The antioxidative and hepatoprotective potentials of two anthraquinones, alaternin (2-hydroxyemodin) and emodin, to scavenge and/or inhibit hydroxyl radicals generated by the Fenton reaction and to protect tacrine-induced cytotoxicity in human liver derived HepG2 cells were evaluated, respectively. The inhibitory activity on hydroxyl radical generated in a cell-free chemical system (FeSO4/H2O2) was investigated by a fluorescence spectrophotometer using a highly fluorescent probe, 2',7'-dichlorofluorescein. The hydroxyl radical scavenging activity was determined by electron spin resonance spectroscopy using 5,5-dimethy-1-pyrroline-N-oxide as hydroxyl radicals trapping agents. Tacrine-induced HepG2 cell toxicity was determined by a 3-[4,5-dimethylthiazole-2yl]-2,5-diphenyltertrazolium bromide assay. Although the scavenging activity of alaternin on hydroxyl radical was similar to that of emodin in dose-dependent patterns, the inhibitory activity exhibited by the former on hydroxyl radical generation was stronger than that of the latter, with IC50 values of 3.05 +/- 0.26 microM and 13.29 +/- 3.20 microM, respectively. In addition, the two anthraquinones, alaternin and emodin showed their hepatoprotective activities on tacrine-induced cytotoxicity, and the EC50 values were 4.02 microM and 2.37 microM, respectively. Silymarin, an antihepatotoxic agent used as a positive control exhibited the EC50 value of 2.00 microM. These results demonstrated that both alaternin and emodin had the simultaneous antioxidant and hepatoprotective activities.     

Photoproducts of indomethacin exhibit decreased hydroxyl radical scavenging and xanthine oxidase inhibition activities

Indomethacin (IN) is a widely used nonsteroidal anti-inflammatory drug. In this study, four photoproducts of IN (IN1–IN4) were produced and isolated from photoirradiated IN. This study investigated the abilities of IN and its photoproducts to scavenge hydroxyl radicals and inhibit xanthine oxidase (XO). The hydroxyl radical-scavenging activity was measured in vitro by electron spin resonance spectrometry using 5,5-dimethyl-1-pyrroline-N-oxide as a spin trapping agent. Enzyme activity was measured by continuous monitoring of uric acid formation, using xanthine as a substrate. The results showed that, among all the related products, IN has the strongest hydroxyl radical-scavenging (IC₅₀ = 65 μM) and XO inhibitory (IC₅₀ = 86 μM) effects. To further understand the stereochemistry of the reactions between these IN derivatives and XO, we performed computer-aided molecular modeling. IN was the most potent inhibitor with the most favorable interaction in the reactive site. Various photoproducts exhibited affinity toward XO as a result of the absence of hydrogen bonding with molybdopterin domain.     

Effects of hydroxyl radical scavenging on cisplatin-induced p53 activation, tubular cell apoptosis and nephrotoxicity

Nephrotoxicity is a major side effect of cisplatin, a widely used cancer therapy drug. Recent work has suggested a role of p53 in renal cell injury by cisplatin. However, the mechanism of p53 activation by cisplatin is unclear. This study determined the possible involvement of oxidative stress in p53 activation under the pathological condition using in vitro and in vivo models. In cultured renal proximal tubular cells, cisplatin at 20 microM induced an early p53 phosphorylation followed by protein accumulation. Cisplatin also induced reactive oxygen species (ROS), among which hydroxyl radicals showed a rapid and drastic accumulation. Dimethylthiourea (DMTU) and N-acetyl-cysteine (NAC) attenuated hydroxyl radical accumulation, and importantly, diminished p53 activation during cisplatin treatment. This was accompanied by the suppression of PUMA-alpha, a p53-regulated apoptotic gene. Concomitantly, mitochondrial cytochrome c release and apoptosis were ameliorated. Notably, DMTU and NAC, when added post-cisplatin treatment, were also inhibitory to p53 activation and apoptosis. In C57BL/6 mice, cisplatin at 30 mg/kg induced p53 phosphorylation and protein accumulation, which was also abrogated by DMTU. DMTU also ameliorated tissue damage, tubular cell apoptosis and cisplatin-induced renal failure. Collectively, this study has suggested a role of oxidative stress, particularly hydroxyl radicals, in cisplatin-induced p53 activation, tubular cell apoptosis and nephrotoxicity.     

Antioxidant and free radical scavenging activity of isoflavone metabolites

1. Soy isoflavones have been extensively studied because of their possible health-promoting effects. Genistein and daidzein, the major isoflavone aglycones, have received most attention; however, they undergo extensive metabolism in the gut and liver, which might affect their biological properties. 2. The antioxidant activity, free radical-scavenging properties and selected cellular effects of the isoflavone metabolites equol, 8-hydroxydaidzein, O-desmethylangiolensin, and 1,3,5 trihydroxybenzene were investigated in comparison with their parent aglycones, genistein and daidzein. 3. Electron spin resonance spectroscopy indicated that 8-hydroxydaidzein was the most potent scavenger of hydroxyl and superoxide anion radicals. Isoflavone metabolites also exhibited higher antioxidant activity than parent compounds in standard antioxidant (FRAP and TEAC) assays. However, for the suppression of nitric oxide production by activated macrophages, genistein showed the highest potency, followed by equol and daidzein. 4. The metabolism of isoflavones affects their free radical scavenging and antioxidant properties, and their cellular activity, but the effects are complex.     

Cytotoxic and radical scavenging activity of blended herbal extracts

Chinese medicines have been applied to a variety of diseases producing various favorable effects, possibly due to the interactions between individual components. Establishment of an evaluation method for such interactions may facilitate the production of new natural medicines. We investigated here the interaction of the hot water extract of Aconiti Tuber (one of the most prominent Chinese medicines) and that of Scutellariae Radix, Coptidis Rhizoma, Glycyrrhizae Radix, Atractylodesi, Lanceae Rhizoma or Poria, by measuring the superoxide anion (O2-), hydroxyl radical (OH) and nitric oxide (NO) scavenging activity, using ESR spectroscopy. We found that a 1:1 mixture of the hot water extract of one herb and that of another herb (referred to as a combined formula) showed a higher radical scavenging activity and cytotoxic activity than the hot water extract of a 1:1 mixture of two herbs (referred to as a blended formula). Both formulae showed higher cytotoxic activity against human oral tumor cell lines than against normal cells. These data further confirm the medicinal usefulness of combinations of empirical Chinese medicines.     

Free radical scavenging and antioxidative activity of melatonin derivatives

This article describes the synthesis and antioxidative properties of melatonin derivatives. Tryptamines and cysteinyl or mercaptopropionyl derivatives were deliberately condensed with coupling reagents to give melatonin derivatives 4a-d and 5a, b. The preliminary evaluation indicated that compound 4c showed improved scavenging activity compared with vitamin C (IC50 43 microM vs 65 microM, where IC50 is the concentration of the test compound that induced a change of 50% in absorbance during the 30 min observation) on diphenyl-p-picrylhydrazyl (DPPH) tests. Derivative 5b, which possesses the thiolactyl moiety, showed moderate potency compared with melatonin (IC50 235 microM vs 690 microM) in the H(2)O(2) scavenging test. Intriguingly, 4c displayed 2-fold more potency than melatonin (IC50 51 microM vs 125 microM) in scavenging NO in the macrophage model. These results suggested that the cysteinyl-conjugated derivative 4c may be a suitable lead to further optimize potent antioxidants for certain oxidative stress conditions.     

Antioxidant and free radical scavenging activity of isoflavone metabolites

1. Soy isoflavones have been extensively studied because of their possible health-promoting effects. Genistein and daidzein, the major isoflavone aglycones, have received most attention; however, they undergo extensive metabolism in the gut and liver, which might affect their biological properties. 2. The antioxidant activity, free radical-scavenging properties and selected cellular effects of the isoflavone metabolites equol, 8-hydroxydaidzein, O-desmethylangiolensin, and 1,3,5 trihydroxybenzene were investigated in comparison with their parent aglycones, genistein and daidzein. 3. Electron spin resonance spectroscopy indicated that 8-hydroxydaidzein was the most potent scavenger of hydroxyl and superoxide anion radicals. Isoflavone metabolites also exhibited higher antioxidant activity than parent compounds in standard antioxidant (FRAP and TEAC) assays. However, for the suppression of nitric oxide production by activated macrophages, genistein showed the highest potency, followed by equol and daidzein. 4. The metabolism of isoflavones affects their free radical scavenging and antioxidant properties, and their cellular activity, but the effects are complex.     

Detection of free radical scavenging activity of schisanhenol by electron spin resonance

It was reported that Schisanhenol (Sal) isolated from Schisandrae Rubriflora inhibited lipid peroxidation induced by ferrous-cysteine and NADPH-ascorbic acid. In this studies the oxygen radical scavenging activity of Sal was detected by electron spin resonance (ESR) and spin trapping. Sal was shown to scavenge oxygen radicals produced by human neutrophils (Neu) stimulated by tetradecanoylphorbol acetate (TDPA). But no effect of Sal was seen on oxygen consumption measured by spin label oximetry in Neu during respiratory burst. In Fenton reaction system, the inhibitory rate of hydroxyl radical by Sal was 34.4%. In xanthine-xanthine oxidase and uv-irradiation of riboflavin systems, Sal scavenged superoxide anion radical by 26.1% and 21.9%, respectively. In all these systems the action of Sal was more potent than that of vitamin E. It may be concluded that Sal possesses a free radical-scavenging activity.     

溪黄草提取物成分预试及对羟自由基的清除作用

目的初步测定溪黄草提取物的化学成分类型及其对羟自由基的清除作用。方法用水、乙醇和石油醚对溪黄草进行提取,根据颜色反应及沉淀反应初步判断所含化学成分的类型,利用结晶紫作显色剂的分光光度法研究各提取物对羟自由基的清除作用。结果溪黄草水提取物对Fenton反应产生的羟自由基具有清除作用,而乙醇和石油醚提取物对羟自由基的清除作用不明显。结论溪黄草中的水溶性成分对羟自由基具有清除作用。     

Synthesis and free radical scavenging activity of coumarin derivatives containing a 2-methylbenzothiazoline motif

Coumarin and benzothiazole scaffolds can be found in a number of natural or synthetic antioxidants. In an effort to develop a novel radical scavenger and potential antioxidant, a series of coumarin derivatives containing 2‐methylbenzothiazoline motif and related compounds was synthesized and evaluated for their DPPH (1,1‐diphenyl‐2‐picrylhydrazyl) and ABTS^?+ (2,2′‐azinobis(3‐ethylbenzothiazoline‐6‐sulfonic acid) radicals scavenging activities. Among them, 7‐hydroxy‐3‐(2‐methyl‐2,3‐dihydrobenzo[d]thiazol‐2‐yl)‐2H‐chromen‐2‐one ( 3e ) has shown a significant free radical scavenging activity. From the structure–activity point of view, it was found that phenolic coumarin ring and benzothiazoline moiety in target compounds may contribute to the scavenging activity against free radicals.     

Oxygen radical scavenging activity of phenylbutenones and their correlation with antiinflammatory activity

A number of ring substituted(E)-4-phenyl-3-buten-2-ones including dehydrozingerone were studied for their oxygen radical scavenging properties. They scavenged superoxide and hydroxyl radicals to an appreciable extent. Good correlation (r = 0.87) was obtained between superoxide scavenging and antiinflammatory activity. The correlation was not significant with the hydroxyl scavenging activity.     

Effect of Luffa echinata on lipid peroxidation and free radical scavenging activity

The dried alcoholic (50%) extract of the plant Luffa echinata was investigated for inhibition of lipid peroxidation, for hydroxyl radical scavenging activity and interaction with 1,1-diphenyl-2-picrylhydrazyl stable free radical (DPPH). It was found that the test extract exhibited a considerable inhibition of lipid peroxidation and possessed hydroxyl radical scavenging activity. Evaluation of antiradical scavenging activity showed significant interaction with DPPH. These properties could be considered as a useful and exploitable combination for justifying the reported activity.