Isolation of antioxidant compounds from the methanolic extract of the roots of Decalepis hamiltonii (Wight and Arn.)

The tuberous roots of Decalepis hamiltonii are consumed as pickles and beverages and are believed to possess health-promoting properties. We have investigated the antioxidant potential of the roots. The methanolic extract of the root showed a high antioxidant activity. The methanolic extract was fractionated on a silica gel column, which showed three major fractions with good antioxidant activity. The active fractions were further subjected to preparative thin layer and silica gel column chromatography, which yielded six pure compounds. The purified compounds were characterized by MS, 1H NMR, 13C NMR, and two-dimensional NMR spectroscopic techniques and identified as 2-hydroxy-4-methoxybenzaldehyde, p-anisaldehyde, vanillin, borneol, salicylaldehyde, and bis-2,3,4,6-galloyl-alpha/beta-D-glucopyranoside. The latter compound, named decalepin, is a new antioxidant molecule from the plant kingdom. The purified compounds showed antioxidant activities in in vitro assays such as inhibition of lipid peroxidation, hydroxyl radical, superoxide anion, and 1,1-diphenyl-2picrylhydrazyl radical scavenging. This is the first report of the antioxidant constituents of the roots of Decalepis hamiltonii.     

Studies on the antioxidant activity of pomegranate (Punica granatum) peel and seed extracts using in vitro models.

Antioxidant-rich fractions were extracted from pomegranate (Punica granatum) peels and seeds using ethyl acetate, methanol, and water. The extracts were screened for their potential as antioxidants using various in vitro models, such as beta-carotene-linoleate and 1,1-diphenyl-2-picryl hydrazyl (DPPH) model systems. The methanol extract of peels showed 83 and 81% antioxidant activity at 50 ppm using the beta-carotene-linoleate and DPPH model systems, respectively. Similarly, the methanol extract of seeds showed 22.6 and 23.2% antioxidant activity at 100 ppm using the beta-carotene-linoleate and DPPH model systems, respectively. As the methanol extract of pomegranate peel showed the highest antioxidant activity among all of the extracts, it was selected for testing of its effect on lipid peroxidation, hydroxyl radical scavenging activity, and human low-density lipoprotein (LDL) oxidation. The methanol extract showed 56, 58, and 93.7% inhibition using the thiobarbituric acid method, hydroxyl radical scavenging activity, and LDL oxidation, respectively, at 100 ppm. This is the first report on the antioxidant properties of the extracts from pomegranate peel and seeds. Owing to this property, the studies can be further extended to exploit them for their possible application for the preservation of food products as well as their use as health supplements and neutraceuticals.     

菜籽蛋白加工废液中多酚和多糖同步提取工艺优化

为开发利用菜籽蛋白加工废液中的生理活性物质,该研究在单因素试验基础上,采用Box-Behnken响应面试验设计法,对菜籽蛋白加工废液中多酚和多糖提取工艺条件进行优化,同时探究两种物质的体外抗氧化活性。结果表明,影响菜籽蛋白加工废液中多酚和多糖得率的因素大小顺序为:乙醇体积分数浸提温度浸提时间,最佳提取工艺为:浸提温度60℃、乙醇体积分数65%、浸提时间31 min,在此条件下多酚得率为2.19%,多糖得率为8.14%;多酚提取物对DPPH·具有较强清除能力,其半抑制质量浓度为0.20 mg/mL,多糖提取物对DPPH·和·OH均具有较强的清除能力,其半抑制质量浓度分别为1.45、2.38 mg/mL;高效液相色谱法初步检测表明,菜籽蛋白加工废液中含有香豆酸、丁香酸、对香豆酸、芥子酸和苯甲酸。研究结果为菜籽蛋白加工废液的再利用提供参考。     

Chemical composition and antimicrobial and antioxidant activities of the essential oil and methanol extract of Hippomarathrum microcarpum (Bieb.) from Turkey

Hippomarathrum microcarpum grows wild in eastern Anatolia, Turkey, and is a plant utilized as food by people. In this study, the in vitro antimicrobial and antioxidant activities of the essential oil and methanol extract from H. microcarpum and its essential oil composition were investigated. The essential oil, which has bornyl acetate, caryophyllene oxide, and beta-caryophyllene as its main components, exhibited activity against eight bacteria, nine fungi, and a yeast, Candida albicans, with minimum inhibitory concentration values ranging from 62.50 to 125 muL/mL; the methanol extract showed weak activity. The antioxidant activity of these extracts was assessed by the beta-carotene bleaching test and the 1,1'-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging test. The inhibition of linoleic acid oxidation was very weak for both extracts tested. The inhibition percentages were found to be 22.9 and 33.5% for methanol and essential oil, respectively, at the concentration of 2 g/L. The oil scavenged DPPH at higher concentrations (IC50 = 10.69 +/- 0.05 mg/mL), but the methanol extract exhibited no activity. The total phenolic content of the methanol extract was found to be 4.7 +/- 0.1%.     

Chemical composition and antioxidant activity of phenolic compounds from wild and cultivated Sclerocarya birrea(Anacardiaceae) leaves

A quantitative study of the phenolic constituents of wild and cultivated leaves of Sclerocarya birrea(Anacardiaceae) was carried out by HPLC-UV/PDA and LC-MS. Phytochemical analysis of the methanol extract of wild plants led to the isolation of one new flavonol glycoside, quercetin 3-O-alpha-l-(5' '-galloyl)-arabinofuranoside (1), and eight known phenolic compounds; two epicatechin derivatives were also isolated from the same extract of the cultivated species. The antioxidant activity of all isolated compounds was determined by measuring free radical scavenging effects using the Trolox equivalent antioxidant capacity assay and the coupled oxidation of beta-carotene and linoleic acid (autoxidation assay).     

Phenolic constituents and antioxidant properties of Xanthosoma violaceum leaves

An extract of Xanthosoma violaceum leaves was subjected to a polyphenol profile determination, including total polyphenols, and antioxidant activity evaluation. Analysis of the extract resulted in the isolation of a new flavone C-glycoside, apigenin 6-C-beta-D-glucopyranosyl-8-C-beta-D-apiofuranoside (1), as well as known flavone C-glycosides, including vitexin (2), isovitexin (3), isovitexin 4'-O-rhamnopyranoside (4), apigenin 6-C-[beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside] (5), and apigenin 6,8-diC-beta-D-glucopyranoside (6). The antioxidant activity of the extract was assessed by means of two different in vitro tests: bleaching of the stable 1,1-diphenyl-2-picrylhydrazyl radical (DPPH test) and peroxidation induced by the water-soluble radical initiator 2,2'-azobis(2-amidinopropane) hydrochloride, on mixed dipalmitoylphosphatidylcholine/linoleic acid unilamellar vesicles (LP-LUV test). In both tests used, the extract and a fraction II showed a significant antioxidant/free-radical scavenging effect (fraction II, EC(50) = 11.6 microg/mL) in comparison to alpha-tocopherol (EC(50) = 10.1 microg/mL).     

Novel antioxidant compounds from the aqueous extract of the roots of Decalepis hamiltonii (Wight and Arn.) and their inhibitory effect on low-density lipoprotein oxidation

Roots of Decalepis hamiltonii are consumed as pickles and as a health drink in southern India for their health benefits. The antioxidant properties of the root extracts have been shown previously; this paper reports the isolation of antioxidant compounds from the aqueous extract of the roots of D. hamiltonii. Five novel antioxidant compounds were isolated and characterized by NMR and MS. The compounds exhibited free radical scavenging activity in vitro and inhibited low-density lipoprotein oxidation. This study demonstrates that the root extract of D. hamiltonii is a cocktail of several antioxidant compounds with health implications.     

Antioxidant constituents of radish sprout (Kaiware-daikon), Raphanus sativus L

Methanol extracts of 11 kinds of commonly available vegetables were examined for hydroxyl radical scavenging potency using the bleomycin-Fe method. In this method, the iron ion and bleomycin in water form hydroxyl radicals, and the scavenging activity is monitored by the modified thiobarbituric acid method. All extracts showed scavenging capacity, even though the activity of some of them was lower than that of l-ascorbic acid. Those vegetables were classified into three groups according to their activity, groups showing strong activity, moderate activity, and weak activity, as compared to the activity of l-ascorbic acid at the same concentration. Among them, the methanol extract of radish sprout (Japanese name "kaiware-daikon") exhibited the highest potency (1.8 times as l-ascorbic acid). Then, we investigated the constituents of the methanol extract of radish sprout and the contribution to the overall activity of each compound by examining their activity. As the result, several kinds of sinapinic acid esters and flavonoids were isolated with high radical scavenging potency, which must contribute substantially to the activity.     

Antioxidant activities of grape (Vitis vinifera) pomace extracts

Antioxidant-rich fractions were extracted from grape (Vitis vinifera) pomace using ethyl acetate, methanol, and water. The extracts were screened for their potential as antioxidants in different models. The ethyl acetate, methanol, and water extracts showed 76, 87.1, and 21.7% antioxidant activities at 100 ppm, respectively, using the 1,1-diphenyl-2-picrylhydrazyl model system. As the methanol extract of grape pomace showed maximum antioxidant activity among all of the extracts, it was selected to determine its effect on lipid peroxidation, hydroxyl radical scavenging activity, and human low-density lipoprotein (LDL) oxidation. The methanol extract showed 71.7, 73.6, and 91.2% inhibition using the thiobarbituric acid method, hydroxyl radical scavenging activity, and LDL oxidation, respectively, at 200 ppm. Treatment of albino rats of the Wistar strain with a single dose of CCl(4) at 1.25 mL/kg of body weight decreases the activities of catalase, superoxide dismutase (SOD), and peroxidase by 81, 49, and 89%, respectively, whereas the lipid peroxidation value increased nearly 3-fold. Pretreatment of the rats with the methanolic extract of grape pomace at 50 mg/kg (in terms of catechin equivalents) followed by CCl(4) treatment causes restoration of catalase, SOD, and peroxidase by 43.6, 73.2, and 54%, respectively, as compared with control, whereas lipid peroxidation was restored to values comparable with the control. Histopathological studies of the liver of different groups also support the protective effects exhibited by the methanol extract of grape pomace by restoring the normal hepatic architecture. Owing to this property, the studies on grape pomace can be further extended to exploit its possible application for the preservation of food products as well as a health supplement and neutraceutical.     

Antioxidant activity of Centaurium erythraea infusion evidenced by its superoxide radical scavenging and xanthine oxidase inhibitory activity.

Centaurium erythraea Rafin. (Gentianaceae) has long been used in traditional medicine. This plant contains considerable amounts of polyphenolic compounds, namely, xanthones and phenolic acids as the main constituents. Because phenolic groups exhibit activity as radical scavengers and/or metal chelators, this study evaluated the superoxide radical scavenging properties of a lyophilized infusion obtained from C. erythraea flowering tops. Superoxide radical scavenging activity was assayed using enzymatic (xanthine/xanthine oxidase) and nonenzymatic (NADH/phenazine methosulfate) superoxide generating systems. This study provided evidence that C. erythraea exhibits interesting antioxidant properties, expressed either by the capacity to scavenge superoxide radical or to noncompetitively inhibit xanthine oxidase. The main phenolic compounds present in this extract were several esters of hydroxycinnamic acids, namely, p-coumaric, ferulic, and sinapic acids.     

Evaluation of extracts from Gevuina avellana hulls as antioxidants

The antioxidant activity of the extracts from Gevuina avellana hulls was evaluated and compared with that of BHT (butylated hydroxytoluene) and BHA (butylated hydroxyanisole), using the beta-carotene bleaching assay, the accelerated oxidation of crude soybean oil, and the 2,2-diphenyl-beta-picrylhydrazyl (DPPH) radical scavenging method. Solvents of different polarity were used to obtain the extracts. Both the extraction yield and the antioxidant activity were strongly dependent on the solvent. The ethanol and diethyl ether soluble fractions were the most active with the beta-carotene assay. Ethanol and methanol extracts were the most active in hydrogen radical scavenging activity. Water and methanol inhibited more efficiently the oxidation of soybean oil at 70 and 80 degrees C, respectively. As a general trend, increased antioxidant activity was observed for increased extract concentration. Except the acetone extracts, all were stable after 6 months storage at 4 degrees C. The ethanol solubles from G. avellana hulls present antioxidant activity similar to that of synthetic antioxidants and to other reported residual agroindustrial materials.     

Antimicrobial and antioxidant activity of the essential oil and methanol extracts of Thymus pectinatus Fisch. et Mey. Var. pectinatus (Lamiaceae)

The essential oil, obtained by using a Clevenger distillation apparatus, and water-soluble (polar) and water-insoluble (nonpolar) subfractions of the methanol extract of Thymus pectinatus Fisch. et Mey. var. pectinatus were assayed for their antimicrobial and antioxidant properties. No (or slight) antimicrobial activity was observed when the subfractions were tested, whereas the essential oil showed strong antimicrobial activity against all microorganisms tested. Antioxidant activities of the polar subfraction and the essential oil were evaluated using 2,2-diphenyl-1-picrylhydrazyl, hydroxyl radical, superoxide radical scavenging, and lipid peroxidation assays. The essential oil, in particular, and the polar subfraction of the methanol extract showed antioxidant activity. The essential oil was analyzed by GC/MS, and 24 compounds, representing 99.6% of the essential oil, were identified: thymol, gamma-terpinene, p-cymene, carvacrol, and borneol were the main components. An antimicrobial activity test carried out with fractions of the essential oil showed that the activity was mainly observed in those fractions containing thymol, in particular, and carvacrol. The activity was, therefore, attributed to the presence of these compounds. Other constituents of the essential oil, such as borneol, gamma-terpinene, and p-cymene, could be also taken into account for their possible synergistic or antagonistic effects. On the other hand, thymol and carvacrol were individually found to possess weaker antioxidant activity than the crude oil itself, indicating that other constituents of the essential oil may contribute to the antioxidant activity observed. In conclusion, the results presented here show that T. pectinatus essential oil could be considered as a natural antimicrobial and antioxidant source.     

Comparison between the radical scavenging activity and antioxidant activity of six distilled and nondistilled mediterranean herbs and aromatic plants

Thirty-six different extracts of six herbs and aromatic plants (fennel, common melilot, milfoil, lavandin cv. Super, spike lavender, and tarragon) were evaluated for their radical scavenging activity by the DPPH*, NBT/hypoxanthine superoxide, and *OH/luminol chemiluminescence methods, and for their antioxidant activity by the beta-carotene blenching test. The total phenolic content was also determined by the Folin-Ciocalteu method. The plant material included cultivated plants and their wastes after being distilled for essential oils. Both remarkably high phenolic content and radical scavenging activities were found for the ethyl acetate and dichloromethane fractions among the different plant extracts. In general, the distilled plant material was found to exhibit a higher phenolic content as well as antioxidant and radical scavenging activities than the nondistilled material. Ethyl acetate and dichloromethane extracts, and even some crude extract, of both distilled and nondistilled plants exhibited activities comparable to those of commercial extracts/compounds, thus making it possible to consider some of them as a potential source of antioxidants of natural origin.     

Antioxidant activity of polyphenols in carob pods.

We extracted polyphenols from carob (Ceratonia siliqua L.) pods, and evaluated the in vitro antioxidant activity of the crude polyphenol fraction (CPP). The total polyphenol content in CPP determined by the Folin-Ciocalteu method was 19.2%. The condensed tannin content determined by the vanillin and proanthocyanidin assay systems was 4.37% and 1.36%, respectively. beta-Carotene bleaching, 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging, inhibition of lipid peroxidation by the erythrocyte ghost, and microsomal assay systems were used to evaluate the antioxidant activity. CPP showed a stronger inhibitory effect against the discoloration of beta-carotene than other polyphenol compounds such as catechins and procyanidins. CPP had weaker antioxidant activity in the DPPH free radical scavenging, the erythrocyte ghost, and microsomal systems than authentic polyphenol compounds at the same concentrations. The activity adjusted by the polyphenol concentration was, however, comparable to that of authentic polyphenol compounds. Considering most carob pods are discarded and not effectively utilized at present, these results suggested that carob pods could be utilized as a functional food or food ingredient.     

Phenylpropanoid glycosides from Tynanthus panurensis: characterization and LC-MS quantitative analysis

A phytochemical analysis of the methanol extract of Tynanthus panurensis bark led to the isolation of one new phenylpropanoid glycoside, eugenol-O-[beta-D-xylopyranosyl-(1-->5)-O-beta-D-apiofuranosyl-(1-->6)-O-beta-D-glucopyranoside], the known verbascoside, isoverbascoside, and leucosceptoside, along with the known flavonoid apigenin 8-C-[beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside], namely, katchimoside. Their structures were established by NMR and ESIMS experiments. Additionally, a quantitative study of the phenylpropanoid glycosides fraction of T. panurensis bark and of the hydroalcoholic extract prepared according to the traditional recipe was performed by combining high-performance liquid chromatography diode array detection with positive electrospray ionization tandem mass spectrometry. The new eugenol derivate was found to be the most abundant phenylpropanoid glycoside in both dried bark (19.5 mg/g) and hydroalcoholic extract (0.24 mg/mL). The antioxidant activity of all the isolated compounds and of the methanol and hydroalcoholic extract of the bark was determined by measuring the free radical scavenging effects using the Trolox equivalent antioxidant capacity method. The traditional hydroalcoholic extract showed a moderate activity.     

Antioxidant properties of Antrodia camphorata in submerged culture

The biologically active compounds, antioxidant activities, and free radical scavenging effects of dry matter of cultural medium (DMCM), filtrate (DMF), and different solvent extracts of mycelia from Antrodia camphorata in submerged culture (ACSC) were investigated. DMF showed the strongest inhibition of lipid peroxidation as a function of its concentration, and was comparable to the antioxidant activity of BHA at the same concentration of 0.2 mg/mL. The hexane extract of mycelia had the weakest antioxidant ability, whereas other mycelial extracts exhibited a modest inhibition of lipid peroxidation. DMF and water extract of mycelia (WEM) showed marked activity in free radical scavenging. The antioxidant activities of filtrate and mycelial extracts were correlated with the presence of total polyphenols, the crude triterpenoids, and the protein/polysaccharide ratio of the crude polysaccharides. It was found that DMCM had lower antioxidant ability than DMF in different model systems, indicating that the major antioxidant components in DMF must be derived from the secondary metabolites of mycelia. The results presented herein indicate that DMF could possibly act as a chemopreventing agent with respect to free radical-related diseases.     

Free radical scavenging activities measured by electron spin resonance spectroscopy and B16 cell antiproliferative behaviors of seven plants.

In an effort to discover new antioxidant natural compounds, seven plants that grow in France (most of them in the Limousin countryside) were screened. Among these plants, was the extensively studied Vitis vinifera as reference. For each plant, sequential percolation was realized with five solvents of increasing polarities (hexane, chloroform, ethyl acetate, methanol, and water). Free radical scavenging activities were examined in different systems using electron spin resonance (ESR) spectroscopy. These assays were based on the stable free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH), the hydroxyl radicals generated by a Fenton reaction, and the superoxide radicals generated by the X/XO system. Antiproliferative behavior was studied on B16 melanoma cells. ESR results showed that three plants (Castanea sativa, Filipendula ulmaria, and Betula pendula) possessed, for the most polar fractions (presence of phenolic compounds), high antioxidant activities in comparison with the Vitis vinifera reference. Gentiana lutea was the only one that presented a hydroxyl scavenging activity for the ethyl acetate and chloroform fractions. The antiproliferative test results showed that the same three plants are the most effective, but for the apolar fractions (chloroform and hexane).     

Antioxidant activity of Myristica malabarica extracts and their constituents

The 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay of the ether, methanol, and aqueous extracts of the spice Myristica malabarica (rampatri) revealed the methanol extract to possess the best antioxidant activity. Column chromatography of the methanol extract led to the isolation of a new 2-acylresorcinol and four known diarylnonanoids of which the diarylnonanoid, malabaricone C, showed the maximum DPPH scavenging activity. Malabaricone C could prevent both Fe(II)- and 2,2'-azobis(2-amidinopropane)dihydrochloride-induced lipid peroxidation (LPO) of rat liver mitochondria more efficiently than curcumin. The anti-LPO activity of malabaricone C was attributed to its better radical scavenging and Fe(II) chelation capacities. The superior activity of malabaricone C was rationalized by a systematic structure-activity correlation of the results obtained with the structurally related diarylnonanoids and curcumin. Malabaricone C also prevented the gamma-ray-induced damage of pBR322 plasmid DNA in a concentration-dependent manner. The radioprotective activity was found to correlate with its (*)OH radical scavenging property, which matched well with that of d-mannitol.     

Chemical composition, iron bioavailability, and antioxidant activity of Kappaphycus alvarezzi (Doty)

Kappaphycus alvarezzi, an edible seaweed from the west coast of India, was analyzed for its chemical composition. It was found that K. alvarezzi is rich in protein (16.24% w/w) and contains a high amount of fiber (29.40% w/w) and carbohydrates (27.4% w/w). K. alvarezzi showed vitamin A activity of 865 mug retinal equivalents/100 g of sample. It contained a higher quantity of unsaturated fatty acids (44.50% of the total), in which relative percentage of oleic acid was 11%, cis-heptadecanoic acid 13.50%, and linoleic acid 2.3% and 37.0% of saturated fatty acids (mainly heptadecanoic acid). K. alvarezziwas also found to be good source of minerals, viz 0.16% of calcium, 0.033% of iron, and 0.016% of zinc, which are essential for various vital biological activities. Bioavailability of iron by in vitro methods showed a higher efficiency in intestinal conditions than in stomach conditions. Ascorbic acid influenced higher bioavailability of iron. Successive extracts of n-hexane, acetone, ethyl acetate, ethanol, and direct extractables of chloroform/methanol (1:1 and 2:1) were screened for antioxidant activity using a beta-carotene linoleic acid model system (B-CLAMS), DPPH (alpha,alpha-diphenyl-beta-picrylhydrazyl) model system and hydroxyl radical scavenging activity. The chloroform/methanol (2:1) extract has shown 82.5% scavenging activity at 1000 ppm. Acetone fraction extracts at the 1000 ppm level showed 63.31% antioxidant activity in beta-carotene linoleic acid system. The acetone extract showed 46.04% scavenging activity at 1000 ppm concentration. In the case of hydroxyl radical scavenging activity, all the extracts showed better activity at the concentrations of 25 and 50 ppm, where at the 50 ppm level ethyl acetate extract showed 76.0%, acetone 75.12%, and hexane 71.15% activity, respectively. Results of this study suggest the utility of K. alvarezzi (Eucheuma) for various nutritional products, including antioxidant for use as health food or nutraceutical supplement.     

Effect of principal polyphenolic components in relation to antioxidant characteristics of aged red wines.

Aged red wines possess significantly different polyphenolic composition compared with young ones, mainly due not only to formation of polymeric compounds but also because of oxidation, hydrolysis, and other transformations that may occur in native grape phenolics during aging. Representative Greek, single-variety, aged red wines were examined for total phenol, total flavanol, and total anthocyanin content using spectrophotometry, and attempts were made to establish correlations with the antiradical, reducing, and hydroxyl free radical scavenging activity. In addition, HPLC analyses were carried out, to ascertain whether individual polyphenols are actually responsible for the antioxidant effects of aged red wines. It was found that total flavanols are the class of polyphenols that account for hydroxyl free radical scavenging efficacy and to a lesser extent for antiradical and reducing ability, whereas there was a less significant link between the antioxidant properties and the total phenolics and only a weak relationship to total anthocyanin content. The correlation of the antioxidant properties with the principal polyphenols showed that individual compounds are weakly associated with all the antioxidant parameters, suggesting that the expression of antioxidant activity in aged red wines is rather a consequence of synergism between various phenolics, and it is not simply attributed to specific constituents.