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1.
In recently, there has been a great interest in natural antioxidants as bioactive components of food, nutraceuticals or potential drugs against several diseases. In our study, 88 extracts from various parts of plants from European Asteraceae and Cichoriaceae were assayed for radical scavenging activity by means of DPPH (1,1-diphenyl-2-picryl hydrazyl radical) test using the SIA (Sequential injection analysis) method developed for this purpose in our laboratory. DPPH radical scavenging activity of all tested plant extracts was evaluated according to the IC(50) parameter. 29 extracts exhibited IC(50) value lower than 0.1 mg/mL. The leaves of Leuzea carthamoides (IC(50) = 0.046 mg/mL) were chosen as the most promising sample for a subsequent phytochemical study, which resulted in isolation of seven natural compounds, namely, 4',5,7-trihydroxy-6-methoxyflavone (hispidulin) (1), 5, 7, 3', 4'- tetrahydroxyflavanone (eriodictyol) (2), 3',4',5,7-pentahydroxy-6-methoxyflavonol (patuletin) (3), eriodictyol-7-beta-glucopyranoside (4), 6-hydroxykaempferol-7-O-(6'-O-acetyl-beta-D-glucopyranoside) (5), 4-hydroxybenzoic acid (6) and 3,4-dihydroxybenzoic acid (protocatechuic acid) (7). Antioxidant activity of the isolated compounds was evaluated by DPPH test and ferric reducing antioxidant power (FRAP) test and compared with trolox and quercetin. Both tests evaluated the flavonoid (5) as the most active antioxidant. This result was confirmed by comparison with known data concerning the structure/activity relationships of flavonoids.  相似文献   

2.
Phenylpropanoid glycosides, 1'-O-benzyl-alpha-L-rhamnopyranosyl-(1'-->6')-beta-D-glucopyranoside (1) and alpha-L-xylopyranosyl-(4'-->2')-(3-O-beta-D-glucopyranosyl)-1'-O-E-caffeoyl-beta-D-glucopyranoside (2), together with the known derivatives, 1,6-di-O-caffeoyl-beta-D-glucopyranoside (3), 1-O-(E)-caffeoyl-beta-D-glucopyranoside (4) and 1-O-(E)-feruloyl-beta-D-glucopyranoside (5), were isolated from leaves of Coussarea hydrangeifolia. Their structures were determined by IR, HRESIMS, and 1D and 2D NMR experiments, and their antioxidant activities, evaluated by assaying the free radical scavenging capacity using the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical as substrate. The antioxidant activities of 3 and 4 (IC50 values of 15.0 and 19.2 microM, respectively) were comparable to that of the standard positive control caffeic acid, whilst 2 and 5 were only weakly active and 1 was inactive.  相似文献   

3.
The methanol extract of the dried ripe fruits of Alpinia rafflesiana was investigated for its DPPH free radical scavenger constituents. 2',3',4',6'-Tetrahydroxychalcone (7), which has never been isolated from natural sources was found to be most active as a DPPH free radical scavenger with the IC50 value of 55 microM. Other known compounds isolated from this species include 5,6-dehydrokawain (1), flavokawin B (2). 1,7-diphenyl-5-hydroxy-6-hepten-3-one (3), (-)-pinocembrin (4), cardamonin (5) and (-)-pinostrobin (6). The DPPH free radical scavenger compounds were detected using TLC autographic analysis. The percentage inhibition of DPPH free radical scavenging activity was measured on isolates (5-7) using colorimetric analysis.  相似文献   

4.
DPPH radical scavenging reactions of protocatechuic acid and its methyl ester were investigated in various solvents. In alcoholic solvents, methyl protocatechuate rapidly scavenged more than four equivalents of the radical, whereas approximately two equivalents were consumed in aprotic solvents. Methyl, ethyl, butyl, isopropyl, and tert-butyl protocatechuates were examined for their DPPH radical scavenging abilities in methanol or ethanol. As a result, the radical scavenging equivalence of sterically bulky esters tended to decrease compared to that of methyl or ethyl ester. The ABTS radical scavenging ability of those esters in water also showed the same tendency. Since 2-methoxy derivatives were detected in the reaction mixture of methyl protocatechuate and DPPH radical in methanol, a nucleophilic attack of an alcoholic molecule on the o-quinone intermediate, which is sensitive to steric hindrance from alkyl groups of both esters and alcoholic solvents, must be crucial for total radical scavenging abilities.  相似文献   

5.
Rosmarinus officinalis extracts were investigated by a combination of bioassays and biochemical analysis to identify bioactive compounds. The 2,2-diphenyl-2-picrylhydracyl hydrate (DPPH) radical scavenging method, Folin-Ciocaulteau method and HPLC chromatography were used to study the distribution and levels of antioxidants (AOXs). Antimicrobial activity analysis was carried out using the disk diffusion and broth dilution techniques. A good correlation between the AOX activities and total phenol content in the extracts was found. Although all rosemary extracts showed a high radical scavenging activity, a different efficacy as antimicrobial agent was observed. Methanol extract containing 30% of carnosic acid, 16% of carnosol and 5% of rosmarinic acid was the most effective antimicrobial against Gram positive bacteria (minimal inhibition concentration, MIC, between 2 and 15 μg/ml), Gram negative bacteria (MIC between 2 and 60 μg/ml) and yeast (MIC of 4 μg/ml). By contrast, water extract containing only 15% of rosmarinic acid showed a narrow activity. MIC value of the methanol and water extracts is in a good correlation with the values obtained with pure carnosic acid and rosmarinic acid, respectively. Therefore, our results suggested that the antimicrobial rosemary extracts efficacy was associated with their specific phenolic composition. Carnosic acid and rosmarinic acid may be the main bioactive antimicrobial compounds present in rosemary extracts. From a practical point of view, rosemary extract may be a good candidate for functional foods as well as for pharmaceutical plant-based products.  相似文献   

6.
The rapid evaluation of antioxidant activity of crude borage (Borago officinalis L.) extract was determined by using DPPH free radical method. This borage extract resulted in a rapid decrease of the absorbance and showed very high hydrogen-donating capacity towards the 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical. A new HPLC-DPPH on-line method was applied for a screening of several radical scavenging components in this borage extract as well as for quantitative analysis. This on-line HPLC-DPPH method was developed using a methanolic solution of DPPH-stable radical. The HPLC-separated analytes reacted post-column with the DPPH solution in methanol. The induced bleaching was detected as a negative peak photometrically at 515 nm. The separation of antioxidative components was carried out by gradient HPLC with mobile-phase composition ranging from 2% to 80% acetonitrile with 2% acetic acid in water, UV detection was carried out at 280 nm. The HPLC analysis of borage extract revealed the presence of several radical scavenging components in the borage extract. The results obtained from the chromatograms suggest that some compounds present in the extract possess high radical quenching ability. The dominant antioxidative compound in the crude extract of borage leaves was identified as rosmarinic acid.  相似文献   

7.
Mutagenicity induced by tert-butyl hydroperoxide (BHP) or cumene hydroperoxide (CHP) in Salmonella typhimurium TA102 was effectively reduced by flavonols with 3',4'-hydroxyl groups such as fisetin, quercetin, rutin, isoquercitrin, hyperoxide, myricetin, myricitrin, robinetin, and to a lesser extent also by morin and kaempferol (ID50=0.25-1.05 micromol per plate). With the exception of isorhamnetin, rhamnetin, morin, and kaempferol, closely similar results were obtained with both peroxides. Hydrogenation of the double bond between carbons 2 and 3 (dihydroquercetin, dihydrorobinetin) as well as the additional elimination of the carbonyl function at carbon 4 (catechins) resulted in a loss of antimutagenicity with the notable exception of catechin itself. Again, all flavones and flavanones tested were inactive except luteolin, luteolin-7-glucoside, diosmetin, and naringenin. The typical radical scavenger butylated hydroxytoluene also showed strong antimutagenicity against CHP (ID50=5.4 micromol per plate) and BHP (ID50=11.4 micromol per plate). Other lipophilic scavengers such as alpha-tocopherol and N,N'-diphenyl-1,4-phenylenediamine exerted only moderate effects, the hydrophilic scavenger trolox was inactive. The metal chelating agent 1,10-phenanthroline strongly reduced mutagenicities induced by CHP and BHP (ID50=2.75 and 2.5 micromol per plate) at low concentrations but induced mutagenic activities at higher concentrations. The iron chelator deferoxamine mesylate, however, was less effective in both respects. The copper chelator neocuproine effectively inhibited mutagenicity induced by BHP (ID50=39.7 micromol per plate) and CHP (ID50=25.9 micrommol per plate), the iron chelator 2,2'-dipyridyl was less potent (ID50=6.25 mmol per plate against BHP, 0.42 mmol per plate against CHP). In the absence of BHP and CHP, yet not in the presence of these hydroperoxides, quercetin, rutin, catechin, epicatechin, and naringenin induced strong mutagenic activities in S. typhimurium TA102. Radical scavenging activities of flavonoids against peroxyl radicals generated from 2,2'-azo-bis(2-amidinopropane)dihydrochloride (AAPH) as measured in the haemolysis test, confirmed that in general flavonoids with di- or trihydroxy hydroxyl functions especially in positions 3', 4', 5' are effective radical scavengers. In this test system, however, luteolin was the most potent compound, followed by epicatechin and eriodictyol. Again, isorhamnetin was a potent inhibitor of lysis of red blood cells despite the presence of a 3'-OCH3 function. Radical scavenging activities of flavonoids against the stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) in principle obeyed the rules outlined above. Flavanones, tamarixetin, and rhamnetin, however, were only weakly active against DPPH, while isorhamnetin was again a potent compound. From these results we conclude that in the Salmonella/reversion assay with strain TA102 antimutagenic activities of flavonoids against the peroxide mutagens CHP and BHP are mainly caused by radical scavenging effects.  相似文献   

8.
Antioxidant activity (AOA) assay-guided chemical analysis, using a rat pancreas homogenate model, of aerial parts from Eysenhardtia subcoriacea, led to isolation of the new compound subcoriacin (3-(2'-hydroxy-4',5'-methylendioxyphenyl)-6-(3'-hydroxymethyl-4'-hydroxybut-2'-enyl)-7-hydroxycoumarin) together with the known substances: (+)-catechin, (-)-epicatechin, (+)-afzelechin, eriodictyol, (+)-catechin 3-O-beta-D-galactopyranoside and quercetin 3-O-beta-D-galactopyranoside as bioactive constituents. The structure of the compound was determined from 1D and 2D NMR spectroscopic analyses. Additional known constituents were characterized. The bioactive compounds showed also moderate to strong radical scavenging properties against diphenylpicrylhydrazyl radical (DPPH). In addition, subcoriacin, (+)-catechin, (-)-epicatechin and (+)-afzelechin improved the reduced glutathione levels in rat pancreatic homogenate.  相似文献   

9.
Rosmarinus officinalis extracts were investigated by a combination of bioassays and biochemical analysis to identify bioactive compounds. The 2,2-diphenyl-2-picrylhydracyl hydrate (DPPH) radical scavenging method, Folin–Ciocaulteau method and HPLC chromatography were used to study the distribution and levels of antioxidants (AOXs). Antimicrobial activity analysis was carried out using the disk diffusion and broth dilution techniques. A good correlation between the AOX activities and total phenol content in the extracts was found. Although all rosemary extracts showed a high radical scavenging activity, a different efficacy as antimicrobial agent was observed. Methanol extract containing 30% of carnosic acid, 16% of carnosol and 5% of rosmarinic acid was the most effective antimicrobial against Gram positive bacteria (minimal inhibition concentration, MIC, between 2 and 15 μg/ml), Gram negative bacteria (MIC between 2 and 60 μg/ml) and yeast (MIC of 4 μg/ml). By contrast, water extract containing only 15% of rosmarinic acid showed a narrow activity. MIC value of the methanol and water extracts is in a good correlation with the values obtained with pure carnosic acid and rosmarinic acid, respectively. Therefore, our results suggested that the antimicrobial rosemary extracts efficacy was associated with their specific phenolic composition. Carnosic acid and rosmarinic acid may be the main bioactive antimicrobial compounds present in rosemary extracts. From a practical point of view, rosemary extract may be a good candidate for functional foods as well as for pharmaceutical plant-based products.  相似文献   

10.
Stable free radical scavenging and antiperoxidative activities of resveratrol, a component of grapes and red wine, were evaluated and compared with some other known bioflavonoids (quercetin, catechin, kaempferol, myricetin, fisetin, ellagic acid and naringenin) widely present in the plant kingdom. Free radical scavenging activity was measured in an in vitro chemical system (DPPH assay), while for antiperoxidative activity, biological system comprising of hepatic and pulmonary homogenates was employed. Antiradical activity assay showed quercetin and myricetin to be stronger antiradical agents than resveratrol. Structure-activity study revealed that O-dihydroxy group on ring B of flavonoid plays a crucial role. A double bond at 2-3 position conjugated with a 4-oxo function and hydroxy groups at positions 3 and 5 also contribute towards antiradical activity of flavonoids. Resveratrol exhibited stronger antiradical activity than kaempferol and naringenin and was also more efficient than alpha-tocopherol, a known strong endogenous non-flavonoid antioxidant, used for comparison. In vitro antiperoxidative assay showed fisetin as the strongest and kaempferol as the weakest antioxidant. Resveratrol was found to be stronger antioxidant than catechin, myricetin, kaempferol and naringenin, but was weaker than quercetin, fisetin and alpha-tocopherol. Antiradical and antiperoxidative activities of resveratrol may explain its beneficial effects in disease states. Assays exhibited no direct correlation between antiradical and antiperoxidative activities of the phenolics.  相似文献   

11.
Three quercetin glucosides were isolated from flower buds of Japanese butterbur (Petasites japonicus subsp. gigantea Kitam.) together with caffeic acid as the ingredients that had DPPH radical scavenging activity, using the DPPH-HPLC method for measuring the radical scavenging activity. These quercetin glucosides were identified as quercetin 3-O-beta-D-glucoside, quercetin 3-O-beta-D-6'-O-acetylglucoside, and rutin, and the amounts of the glucosides in flower buds were also examined by HPLC. The flower buds were harvested from four different sites, the total amount of quercetin glucosides in each site was 100-170 mg/100 g fr. wt., and there were no great differences of the amounts between growing fields.  相似文献   

12.
In recently, there has been a great interest in natural antioxidants as bioactive components of food, nutraceuticals or potential drugs against several diseases. In our study, 88 extracts from various parts of plants from European Asteraceae and Cichoriaceae were assayed for radical scavenging activity by means of DPPH (1,1-diphenyl-2-picryl hydrazyl radical) test using the SIA (Sequential injection analysis) method developed for this purpose in our laboratory. DPPH radical scavenging activity of all tested plant extracts was evaluated according to the IC50 parameter. 29 extracts exhibited IC50 value lower than 0.1 mg/mL. The leaves of Leuzea carthamoides (IC50 = 0.046 mg/mL) were chosen as the most promising sample for a subsequent phytochemical study, which resulted in isolation of seven natural compounds, namely, 4′,5,7-trihydroxy-6-methoxyflavone (hispidulin) (1), 5, 7, 3′, 4′- tetrahydroxyflavanone (eriodictyol) (2), 3′,4′,5,7-pentahydroxy-6-methoxyflavonol (patuletin) (3), eriodictyol-7-β-glucopyranoside (4), 6-hydroxykaempferol-7-O-(6″-O-acetyl-β-D-glucopyranoside) (5), 4-hydroxybenzoic acid (6) and 3,4-dihydroxybenzoic acid (protocatechuic acid) (7). Antioxidant activity of the isolated compounds was evaluated by DPPH test and ferric reducing antioxidant power (FRAP) test and compared with trolox and quercetin. Both tests evaluated the flavonoid (5) as the most active antioxidant. This result was confirmed by comparison with known data concerning the structure/activity relationships of flavonoids.  相似文献   

13.
Two xanthones, bangangxanthone A (1) [1,5,8-trihydroxy-6'-methyl-6'-(4-methylpent-3-enyl)- pyrano[2',3':3,4]xanthone] and B (2) [1,4,8-trihydroxy-2-prenylxanthone], along with two known xanthones, 1,5-dihydroxyxanthone, 2-hydroxy-1,7-dimethoxyxanthone and the pentacyclic triterpenoids, friedelin, oleanolic acid and lupeol were isolated from the chloroform extract of the stem bark of Garcinia polyantha. The structures of these compounds were assigned by spectroscopic analysis. Compounds 1-4 showed antioxidant DPPH radical scavenging activities.  相似文献   

14.
A new natural flavonoid patuletin 3′-β-xylofuranoside was isolated from Leuzea carthamoides leaves. The antioxidant activity of this compound was evaluated by the DPPH radical assay and ferric reducing antioxidant power (FRAP) assay, and the results were compared with those for trolox and quercetin. DPPH radical scavenging activity of the tested compounds was expressed by the parameter EC50: patuletin 3′-β-xylofuranoside (56.0 μM), trolox (27.8 μM), and quercetin (25.3 μM). The ferric reducing activity of the compounds was demonstrated as FRAP values at 4 and 60?min: patuletin 3′-β-xylofuranoside (28.4 μM, 35.8 μM), trolox (19.3 μM, 20.2 μM), and quercetin (54.3 μM, 79.9 μM). The structure/activity relationship of the flavonoid is also discussed. The results indicate significant antioxidant potency of patuletin 3′-β-xylofuranoside.  相似文献   

15.
Solvent-dependency of the antiradical reaction of protocatechuic acid (3,4-dihydroxybenzoic acid, PA) and its esters has been investigated. In aprotic solvents, methyl protocatechuate (PAMe) was readily oxidized by two molar equivalents of DPPH radical and converted to protocatechuquinone methyl ester (PQMe). On the other hand, in alcoholic solvents such as methanol, PAMe rapidly consumed five radicals in 30 min and changed to complex oxidized mixtures. A 1H-NMR analysis of the reaction mixture of PAMe and DPPH radical in methanol showed that PAMe was rapidly converted to PQMe and its 3-hemiacetal. In addition, a signal of 2-methoxy-PQMe 3-hemiacetal was also detected in the reaction mixture. The results suggested that PQMe undergoes a nucleophilic attack by the solvent alcohol molecule at the C-2 of the ring in methanol, leading to a regeneration of catechol structure, which accounts well for the higher DPPH radical scavenging activity of PAMe in alcohols than in aprotic solvents.  相似文献   

16.
The present study has been performed to evaluate the antimutagenic activity of quercetin, ascorbic acid and their combination against an oxidative mutagen. An effort was also made to correlate this activity to the in vitro antioxidant activity of these agents. Antimutagenicity testing was done in Ames Salmonella Assay system using Salmonella typhimurium TA102 against t-butylhydroperoxide as an oxidative mutagen. In vitro antioxidant scavenging activity was tested for DPPH free radical, superoxide anion, hydrogen peroxide and hydroxyl radical in their specific test systems. Quercetin (0.5-8 nmole/plate) and ascorbic acid (0.1-100 micromole/plate) showed significant effect. Quercetin (4 and 8 nmole/plate) when combined with ascorbic acid (500 nmole/plate) showed an increase in the antimutagenic activity. In vitro antioxidant activity of quercetin was better than ascorbic acid in all the test systems used. The study indicated that the antimutagenic activity of quercetin was not solely accountable by its antioxidant nature. However, in vitro free radical scavenging activity of quercetin correlated well with the antimutagenic activity.  相似文献   

17.
Tepe B 《Bioresource technology》2008,99(6):1584-1588
This study was designed to examine the in vitro antioxidant activities and rosmarinic acid levels of the methanol extracts of Salvia virgata, Salvia staminea and Salvia verbenaca. The extracts were screened for their possible antioxidant activity by two complementary test systems, namely DPPH free radical scavenging and beta-carotene/linoleic acid systems. In the first case, the most active plant was S. verbenaca (14.30+/-1.42 microg mg(-1)), followed by S. virgata (65.70+/-2.12 microg mg(-1)). S. staminae exhibited the weakest antioxidant activity in this test system of which IC(50) value is 75.40+/-0.57 microg mg(-1). In beta-carotene/linoleic acid test system, S. verbenaca extract was superior to the other extracts studied (inhibition value is 77.03%+/-0.42). Antioxidant activities of BHT, ascorbic acid, curcumin and alpha-tocopherol were determined in parallel experiments. Activity of rosmarinic acid was also screened for better establishing the relationship between rosmarinic acid level and antioxidant activity for the plant extracts. According to the results obtained by spectrophotometric analysis and further supported by HPLC, S. verbenaca has the highest rosmarinic acid level with a value of 29.30+/-0.24 microg mg(-1). Our results showed that the rosmarinic acid and its derivatives are more likely to be responsible for most of the observed antioxidant activities of Salvia species.  相似文献   

18.
A novel flavonol glycoside named camellianoside and three known flavonol glycosides were isolated from the leaves of Camellia japonica. The structure of camellianoside was established as quercetin-3-O-beta-D-xylopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->6)-O-beta-D-glucopyranoside by spectroscopic and chemical methods. The antioxidant activities of these glycosides evaluated by the diphenylpicrylhydrazyl (DPPH) radical scavenging reaction was higher than those of L-cysteine and L-ascorbic acid used as the reference antioxidants.  相似文献   

19.
While screening for bioactive compounds from edible mushrooms, a new potent antioxidant, vialinin A (1), together with a known compound, ganbajunin B (2), and a mixture of ganbajunins D (3) and E (4), were isolated from the dry fruiting bodies of Thelephora vialis. The structure of 1, 5',6'-bis(phenylacetoxy)-1,1':4',1'-terphenyl-2',3',4,4'-tetraol, was elucidated by spectroscopic and chemical methods. This compound had strong 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical-scavenging activity with an EC(50) value of 14.0 microM, nearly equal to that of butylated hydroxytoluene (BHT; EC(50) = 10.0 microM). A radical scavenging experiment using 1 and DPPH radicals indicated that 1 donated two hydrogen atoms to two molecules of the DPPH radical under hydrophobic conditions.  相似文献   

20.
In this study, an aqueous extract of leaves from Melothria maderaspatana was tested for in vitro antioxidant activity. Free radical scavenging assays, such as hydroxyl radical, hydrogen peroxide, superoxide anion radical and 2,2-diphenyl-1-picryl hydrazyl (DPPH), 2,2’-azinobis-(3-ethyl-enzothiazoline-6-sulfonic acid) (ABTS) radical scavenging, and reducing power assay, were studied. The extract effectively scavenged hydroxyl radical, hydrogen peroxide and superoxide anion radicals. It also scavenged DPPH and ABTS radicals. Furthermore, it was found to have reducing power. All concentrations of leaf extract exhibited free radical scavenging and antioxidant power, and the preventive effects were in a dose-dependent manner. The antioxidant activities of the above were compared to standard antioxidants such as butylated hydroxytoluene (BHT), ascorbic acid, and α-tocopherol. The results obtained in the present study indicate that the M. maderaspatana extract could be considered a potential source of natural antioxidant.  相似文献   

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