Antiodidant activity of thiosulfinates derived from garlic

Abstract

Garlic extract significantly inhibited the oxidation of methyl linoleate in homogeneous acetonitrile solution, whereas the antioxidant effect of allicin-free garlic extract, prepared by removing allicin by prepared by removing allicin by preparative HPLC, was much lower than that of the garlic extract. These results suggest that the antioxidant properties are mostly attributed to the presence of allicin in the garlic extract. Allicin a major component of the thiosulfinates in garlic extract, was found to be effective for inhibiting methyl linoleate oxidation, but its efficiency was less than that of α-tocopherol. Next, the reactivity of allicin toward the peroxyl radical, which is a chain-propagating species, was investigated by direct ESR detection. The addition allicin to 2,2′-azobis(2,4-dimethylvaleronitrile)-peroxyl radical solution caused the signal intensity of the peroxyl radical to dose-dependently decrease, indicating that allicin is capable of scavenging the the peroxyl radical and acting as an antioxidant. Finally, we studied the structure–anioxidant activity relationship for thiosulfinates and suggested that the combination of the allyl group (–CH₂CH=CH₂) and the –S(O)S– group is necessary for the antioxidant action of thiosulfinates in the garlic extract. In addition, one of the two possible combinations, –S(O)S–CH₂CH=CH₂, was found to make a much larger contribution to the antioxidant activity of the thiosulfinates than the other, CH₂=CH–CH₂–S(O)S–.     

Antimicrobial activity of the thiosulfinates isolated from oil-macerated garlic extract

Three thiosulfinates were isolated from oil-macerated garlic extract, and their structures were identified as 2-propene-1-sulfinothioic acid S-(Z,E)-1-propenyl ester [AllS(O)SPn-(Z,E)], 2-propenesulfinothioic acid S-methyl ester [AllS(O)SMe], and methanesulfinothioic acid S-(Z,E)-1-propenyl ester [MeS(O)SPn-(Z,E)]. This is the first report of isolating these thiosulfinates from oil-macerated garlic extract. Antimicrobial activities of AllS(O)SPn-(Z,E) and AllS(O)SMe against Gram-positive and negative bacteria and yeasts were compared with 2-propene-1-sulfinothioic acid S-2-propenyl ester [AllS(O)SAll, allicin] which is well-known as the major thiosulfinate in garlic. Antimicrobial activity of AllS(O)SMe and AllS(O)SPn-(Z,E) were comparable and inferior to that of allicin, respectively. This result suggested that the antimicrobial activity of 2-propene sulfinothioic acid S-alk(en)yl esters were affected by alk(en)yl groups. The order for antimicrobial activity was: allyl > or = methyl > propenyl.     

Antifungal activity of ajoene derived from garlic

The antifungal activity of six fractions derived from garlic was investigated in an in vitro system. Ajoene had the strongest activity in these fractions. The growth of both Aspergillus niger and Candida albicans was inhibited by ajoene at less than 20 micrograms/ml.     

Antifungal activity of ajoene derived from garlic.

The antifungal activity of six fractions derived from garlic was investigated in an in vitro system. Ajoene had the strongest activity in these fractions. The growth of both Aspergillus niger and Candida albicans was inhibited by ajoene at less than 20 micrograms/ml.     

Antioxidant activity of allicin,an active principle in garlic

Garlic has been claimed to be effective against diseases, in the pathophysiology of which oxygen free radicals (OFRs) have been implicated. Effectiveness of garlic could be due to its ability to scavenge OFRs. However, its antioxidant activity is not known. We investigated the ability of allicin (active ingredient of garlic) contained in the commercial preparation Garlicin to scavenge hydroxyl radicals (·OH) using high pressure liquid chromatographic (HPLC) method. ·OH was generated by photolysis of H₂O₂ (1.25–10 moles/ml) with ultraviolet light and was trapped with salicylic acid which is hydroxylated to produce ·OH adduct products 2,3- and 2,5-dihydroxybenzoic acid (DHBA). H₂O₂ produced a concentration-dependent ·OH as estimated by ·OH adduct products 2,3-DHBA and 2,5-DHBA. Allicin equivalent in Garlicin (1.8, 3.6, 7.2, 14.4, 21.6, 28.8 and 36 g) produced concentration-dependent decreases in the formation of 2,3-DHBA and 2,5-DHBA. The inhibition of formation of 2,3-DHBA and 2,5-DHBA with 1.8 g/ml was 32.36% and 43.2% respectively while with 36.0 g/ml the inhibition was approximately 94.0% and 90.0% respectively. The decrease in ·OH adduct products was due to scavenging of ·OH and not by scavenging of formed ·OH adduct products. Allicin prevented the lipid peroxidation of liver homogenate in a concentration-dependent manner. These results suggest that allicin scavenges ·OH and Garlicin has antioxidant activity.     

Antioxidant activity of dihydrofurocoumarins from Corydalis heterocarpa

The aim of this paper is to report the results of investigations into the antioxidant effect of dihydrofurocoumarins (1–6), isolated from the salt marsh plant Corydalis heterocarpa. The scavenging activities of the isolated compounds against DPPH radicals, hydroxyl radicals, and superoxide radicals were evaluated by electron spin resonance. The protective activities of these compounds against hydroxyl radical-mediated genomic DNA damage and peroxynitrite-mediated dihydrorhodamine oxidation were also investigated. The experimental results show that most compounds had antioxidant activity but their capabilities differed a little for the different indicators. Among them, compound 6 exerted the strongest antioxidant activity at a concentration of 100 μM/mL for all tested bioassay systems, compared with other compounds.     

Antioxidant activity of extract from Polygonum cuspidatum

Numerous diseases are induced by free radicals via lipid peroxidation, protein peroxidation and DNA damage. It has been known that a variety of plant extracts have antioxidant activities to scavenge free radicals. Whether Polygonum cuspidatum Sieb. et Zuce has antioxidant activity is unknown. In this study, dried roots of Polygonum cuspidatum were extracted by ethanol and the extract was lyophilized. Free radical scavenging assays, superoxide radical scavenging assays, lipid peroxidation assays and hydroxyl radical-induced DNA strand scission assays were employed to study antioxidant activities. The results indicate that the IC50 value oí Polygonum cuspidatum extract is 110 microg/ml in free radical scavenging assays, 3.2 microg/ml in superoxide radical scavenging assays, and 8 microg/ml in lipid peroxidation assays, respectively. Furthermore, Polygonum cuspidatum extract has DNA protective effect in hydroxyl radical-induced DNA strand scission assays. The total phenolics and flavonoid content of extract is 641.1 +/- 42.6 mg/g and 62.3 +/- 6.0 mg/g. The results indicate that Polygonum cuspidatum extract clearly has antioxidant effects.     

水母胶原蛋白抗氧化活性研究

提取水母胶原蛋白,观察其体内外抗氧化作用。体外采用邻苯三酚自氧化法观察水母胶原蛋白对超氧阴离子(·O2-)的清除作用,采用Fenton反应体系观察对羟自由基(·OH)的清除作用;体内观察水母胶原蛋白对小鼠血清、肝脏、大脑中超氧化物歧比酶(SOD)、过氧化氢酶(CAT),丙二醛(MDA)含量的影响。结果表明:水母胶原蛋白对·O2-、·OH具有良好的清除作用,呈一定的剂量依赖关系,能明显提高小鼠血清、肝脏、大脑中的SOD、CAT含量,能在一定程度上降低血清、肝脏、大脑中的MDA水平。因此,水母胶原蛋白具有显著的抗氧化生物活性。     

Inhibition of microbial growth by ajoene, a sulfur-containing compound derived from garlic.

Ajoene, a garlic-derived sulfur-containing compound that prevents platelet aggregation, exhibited broad-spectrum antimicrobial activity. Growth of gram-positive bacteria, such as Bacillus cereus, Bacillus subtilis, Mycobacterium smegmatis, and Streptomyces griseus, was inhibited at 5 micrograms of ajoene per ml. Staphylococcus aureus and Lactobacillus plantarum also were inhibited below 20 micrograms of ajoene per ml. For gram-negative bacteria, such as Escherichia coli, Klebsiella pneumoniae, and Xanthomonas maltophilia, MICs were between 100 and 160 micrograms/ml. Ajoene also inhibited yeast growth at concentrations below 20 micrograms/ml. The microbicidal effect of ajoene on growing cells was observed at slightly higher concentrations than the corresponding MICs. B. cereus and Saccharomyces cerevisiae were killed at 30 micrograms of ajoene per ml after 24 h of cultivation when cultivation was started at 10(5) cells per ml. However, the minimal microbicidal concentrations for resting cells were at 10 to 100 times higher concentrations than the corresponding MICs. The disulfide bond in ajoene appears to be necessary for the antimicrobial activity of ajoene, since reduction by cysteine, which reacts with disulfide bonds, abolished its antimicrobial activity.     

Antioxidant effects of tetrahydro-beta-carboline derivatives identified in aged garlic extract

1,2,3,4-Tetrahydro-beta-carboline derivatives (THbetaCs) are formed through Pictet-Spengler chemical condensation between tryptophan and aldehydes during food production, storage and processing. In the present study, in order to identify the antioxidants in aged garlic extract (AGE), we fractionated it and identified four THbetaCs; 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acids (MTCC) and 1-methyl-1,2,3,4-tetrahydro-beta-carboline-1,3-dicarboxylic acid (MTCdiC) in both diastereoisomers using liquid chromatography mass spectrometry (LC-MS). Interestingly, these compounds were not detected in raw garlic, but the contents increased during the natural aging process of garlic. In in vitro assay systems, all of these compounds have shown strong hydrogen peroxide scavenging activities. (1S, 3S)-MTCdiC was found to be stronger than the common antioxidant, ascorbic acid. MTCC and MTCdiC inhibited AAPH-induced lipid peroxidation. Both MTCdiCs also inhibited LPS-induced nitrite production from murine macrophages at 10-100 microM. Our data suggest that these compounds are potent antioxidants in AGE, and thus may be useful for prevention of disorders associated with oxidative stress.     

Antioxidant activity of leaf extracts from Bauhinia monandra

Bauhinia monandra Kurz. is used in Brazil for the treatment of diabetes. Since this activity may be correlated with the presence of antioxidant compounds, leaf extracts of B. monandra were evaluated for their radical scavenging capacity (RSC). An ethanolic extract was taken up in aqueous methanol and partitioned with hexane, chloroform, ethyl acetate to yield three organic extracts together with remaining aqueous extract. The RSC was determined spectrophotometrically using 1,1-diphenylpicrylhydrazyl free radical (DPPH). The chloroform and ethyl acetate extracts were the most appropriate as sources of antioxidant compounds as shown by their inhibition concentration (IC50) and inhibition percentage (IP) values. The antioxidant activity of such extracts was attributed to the presence of three compounds of different polarities (flavonoids and steroids). The chloroform and ethyl acetate extracts exhibited an IC50 of approximately 2 mg/g DPPH and IP values in the range of 60-65%. The results indicate that the extracts of B. monandra have a very potent antioxidant activity, compared with the pure catechins used as positive controls and with other plant extracts.     

Antioxidant activity of extract from Polygonum aviculare L

Free radicals induce numerous diseases by lipid peroxidation, protein peroxidation, and DNA damage. It has been reported that numerous plant extracts have antioxidant activities to scavenge free radicals. Whether Polygonum aviculare L. (Polygonaceae) has antioxidant activity is unknown. In this study, dried Polygonum aviculare L. was extracted by ethanol, and the extract was lyophilized. The antioxidant activities of extract powder were examined by free radical scavenging assays, superoxide radical scavenging assays, lipid peroxidation assays and hydroxyl radical-induced DNA strand scission assays. The results show that the IC50 value of Polygonum aviculare L. extract is 50 microg/ml in free radical scavenging assays, 0.8 microg/ml in superoxide radical scavenging assays, and 15 microg/ml in lipid peroxidation assays, respectively. Furthermore, Polygonum aviculare L. extract has DNA protective effect in hydroxyl radical-induced DNA strand scission assays. The total phenolics and flavonoid content of extract is 677.4 +/- 62.7 microg/g and 112.7 +/- 13 microg/g. The results indicate that Polygonum aviculare L. extract clearly has antioxidant effects.     

Antioxidant activity of flavonoids from Sideritis javalambrensis.

Five flavonoid glycosides, 4'-O-methylisoscutellarein 7-O-[6"'-acetylallopyranosyl(1----2)glucopyranoside], 4'-O-methylisoscutellarein 7-O-allopyranosyl(1----2)glucopyranoside, 3'-hydroxy-4'-O-methylisoscutellarein 7-O-[6"'-acetylallopyranosyl(1----2) glucopyranoside], and hypolaetin-8-glucoside have been isolated from Sideritis javalambrensis aerial parts and identified by standard methods. These glycosides have been tested for their antioxidant properties alongside other 7,8-substituted flavonoids using FeSO4/cysteine-induced microsomal lipid peroxidation. Superoxide scavenging activity was assessed in the nitroblue tetrazolium test. Among this series of flavonoids, hypolaetin-8-glucoside is the most potent inhibitor of nonenzymic lipid peroxidation. The antiperoxidative activity of these flavonoids may be related to their superoxide scavenging ability.     

南瓜多糖衍生物的制备及其抗氧化研究

对超声辅助法提取的南瓜粗多糖,进行化学改性得到了硫酸化南瓜多糖和羧甲基南瓜多糖。用邻苯三酚自氧化法检测对超氧阴离子自由基的清除作用,用邻二氮菲-金属铁离子-H2O2体系检测对羟自由基的清除作用。结果表明,南瓜多糖对超氧阴离子自由基无抑制作用,经化学改性后的羧甲基南瓜多糖和硫酸化南瓜多糖对超氧阴离子自由基有明显抑制作用,最大清除率达44％和41．67％。以上3种多糖均能有效清除·OH,随着浓度的增加清除作用加强,最大清除率可达46．49％,22．61％和42．35％0。结果显示,经化学改性后的南瓜多糖有较强的抗氧化作用。     

Antioxidant activity of twenty five plants from Colombian biodiversity

The antioxidant activity of the crude n-hexane, dichloromethane, and methanol extracts from 25 species belonging to the Asteraceae, Euphorbiaceae, Rubiaceae, and Solanaceae families collected at natural reserves from the Eje Cafetero Ecorregión Colombia, were evaluated by using the spectrophotometric 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical-scavenging method. The strongest antioxidant activities were showed by the methanol and dichloromethane extracts from the Euphorbiaceae, Alchornea coelophylla (IC50 41.14 mg/l) and Acalypha platyphilla (IC50 111.99 mg/l), respectively. These two species had stronger DPPH radical scavenging activities than hydroquinone (IC50 151.19 mg/l), the positive control. The potential use of Colombian flora for their antioxidant activities is discussed.     

Antioxidant activity of oligomeric acylphloroglucinols from Myrtus communis L

The use of myrtle (Myrtus communis L.) as a culinary spice and as a flavoring agent for alcoholic beverages is widespread in the Mediterranean area, and especially in Sardinia. Myrtle contains unique oligomeric non-prenylated acylphloroglucinols, whose antioxidant activity was investigated in various systems. Both semimyrtucommulone (1) and myrtucommulone A (2) showed powerful antioxidant properties, protecting linoleic acid against free radical attack in simple in vitro systems, inhibiting its autoxidation and its FeCl3- and EDTA-mediated oxidation. While both compounds lacked pro-oxidant activity, semimyrtucommulone was more powerful than myrtucommulone A, and was further evaluated in rat liver homogenates for activity against lipid peroxidation induced by ferric-nitrilotriacetate, and in cell cultures for cytotoxicity and the inhibition of TBH- or FeCl3-induced oxidation. The results of these studies established semimyrtucommulone as a novel dietary antioxidant lead.     

加拿大一枝黄花提取物的抗氧化活性研究

为进一步开发和利用加拿大一枝黄花(Solidago canadensis),该研究采用氯化铝显色法和福林酚法测定加拿大一枝黄花乙醇提取物及其不同极性萃取物中的总黄酮和总酚的含量;以抗坏血酸(Vitamin C,Vc)和二丁基羟基甲苯(BHT)为阳性对照,应用2,2-联氮-二(3-乙基-苯并噻唑-6-磺酸)二铵盐(ABTS)、1,1-二苯基苦基苯肼(DPPH)自由基清除体系、铁离子还原能力(FRAP)法和抗氧化能力指数(ORAC)法研究其体外抗氧化活性。结果表明:乙酸乙酯萃取物中的总黄酮(202.45 mg·g~(-1))和总酚(485.94 mg·g~(-1))含量最高,且其抗氧化活性最强,并强于阳性对照Vc(P0.05)。因而,加拿大一枝黄花乙酸乙酯萃取物将有可能成为一种潜在的天然高效抗氧化剂,具有广泛的应用前景。     

杜仲内生球毛壳菌的抗氧化活性研究

本文研究了分离自杜仲叶片的内生真菌球毛壳菌菌株No.173发酵液提取物的抗氧化活性,采用铁氰化钾还原力测定法、β-胡萝卜素/亚油酸模型和光照核黄素体系评价了发酵液提取物的抗氧化作用,并采用Folin-Ciocalteu法测定杜仲内生球毛壳菌发酵液提取物总多酚含量。结果表明,其抗氧化能力与Vc基本相当;清除超氧阴离子的能力优于芦丁;多酚含量为255.53±1.38mg/g,是其主要的抗氧化活性成分。