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1.
Lipase-catalyzed synthesis of lipophilic phenolic antioxidants was carried out with a concentrate of n-3 polyunsaturated fatty acids (PUFAs), recovered from oil extracted from salmon ( Salmon salar ) byproduct. Vanillyl alcohol and rutin were selected for the esterification reaction, and obtained esters yields were 60 and 30%, respectively. The antioxidant activities of the esters were compared with those of commercial butylated hydroxytoluene (BHT) and α-tocopherol using DPPH radical scavenging and thiobarbituric acid assays. In the DPPH assay, rutin esters showed better activity than vanillyl esters, and on the contrary in lipophilic medium, vanillyl esters were found to be superior to rutin esters. In bulk oil system, the antioxidant activities of rutin and vanillyl derivatives were lower than that of BHT and α-tocopherol, but in emulsion, they showed better activity than α-tocopherol. By attaching to natural phenolics, the PUFAs are protected against oxidation, and PUFA improves the hydrophobicity of the phenolic, which could enhance its function in lipid systems.  相似文献   

2.
Tyrosinase inhibitory and antioxidant activity of gallic acid and its series of alkyl chain esters were investigated. All inhibited the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) catalyzed by mushroom tyrosinase. However, gallic acid and its short alkyl chain esters were oxidized as substrates yielding the colored oxidation products. In contrast, the long alkyl chain esters inhibited the enzyme activity without being oxidized. This indicates that the carbon chain length is associated with their tyrosinase inhibitory activity, presumably by interacting with the hydrophobic protein pocket in the enzyme. On the other hand, the esters, regardless their carbon chain length, showed potent scavenging activity on the autoxidation of linoleic acid and 1,1-diphenyl-2-p-picryhydrazyl (DPPH) radical, suggesting that the alkyl chain length is not related to the activity. The effects of side-chain length of gallates in relation to their antibrowning activity are studied.  相似文献   

3.
This study investigated the effect of synthetic capsiate, a simplified analogue of capsiate, and vanillyl alcohol on the oxidative stress induced by tert-butyl hydroperoxide (TBH) in a line of fibroblasts derived from monkey kidney (Vero cells). In response to the TBH-mediated oxidative stress, a reduction of the levels of total unsaturated fatty acids and cholesterol was observed, and a rise in the concentrations of conjugated dienes fatty acids hydroperoxides and 7-ketocholesterol. Pretreatment with both synthetic capsiate and vanillyl alcohol preserved Vero cells from oxidative damage and showed a remarkable protective effect on the reduction of the levels of total unsaturated fatty acids and cholesterol, inhibiting the increase of MDA, conjugated dienes fatty acids hydroperoxides, and 7-ketocholesterol. Both compounds were effective against peroxidation of cell membrane lipids induced by TBH, with synthetic capsiate essentially acting as a pro-drug of vanillyl alcohol, its hydrophilic hydrolytic derivative.  相似文献   

4.
Antioxidant activity of capsinoids   总被引:3,自引:0,他引:3  
Hot peppers are a good source of dietary antioxidants, encompassing, apart from widespread compounds (flavonoids, phenolic acids, carotenoids, vitamin A, ascorbic acid, tocopherols), also specific constituents such as the pungent capsaicinoids (capsaicin, dihydrocapsaicin, and related analogues). We have shown that capsinoids also show remarkable antioxidant activity. These benign analogues of capsaicin could protect linoleic acid against free radical attack in simple in vitro systems, inhibiting both its autoxidation and its iron- or EDTA-mediated oxidation. These properties were retained in some simple synthetic analogues (vanillyl nonanoate and its dimerization products). Capsiate, dihydrocapsiate, and their analogues were devoid of pro-oxidant activity and showed a highly significant antioxidant activity in all systems investigated. Vanillyl nonanoate, a simple capsinoid mimic, was also tested on cell cultures for cytotoxic activity and the capacity to inhibit FeCl(3)-induced oxidation.  相似文献   

5.
Some N-(hydroxycinnamoyl)-L-tyrosine and L-DOPA alkyl esters were synthesized and evaluated as a variation of the clovamide (N-caffeoyl-L-3,4-dihydroxyphenylalanine) structure, a known antioxidant found in red clover. The amides were prepared in good yields starting from methyl and dodecylesters of L-tyrosine and L-DOPA by reacting with the N-hydroxysuccinimidyl esters of ferulic, sinapic, and acetyl-protected caffeic acid, respectively. In the DPPH* (2,2-diphenyl-1-picrylhydrazyl) and superoxide radical quencher assays they showed radical scavenging activity equal to or higher than those of the standard antioxidants ascorbic acid and tocopherol. The antioxidative potentials of the clovamide derivatives against bulk lipid oxidation, as determined by the accelerated autoxidation of oils, were equal to or higher than those of the standard antioxidants; some of the compounds were able to protect an emulsion of linoleic acid/beta-carotene against oxidation. N-Caffeoyl L-tyrosine methyl ester and the N-cinnamoyl L-DOPA alkyl esters especially were potent antioxidants in bulk lipids and moderate protectants in emulsions.  相似文献   

6.
Antioxidant properties of ferulic acid and its related compounds   总被引:13,自引:0,他引:13  
Antioxidant activity of 24 ferulic acid related compounds together with 6 gallic acid related compounds was evaluated using several different physical systems as well as their radical scavenging activity. The radical scavenging activity on 1,1-diphenyl-2-picrylhydrazyl (DPPH) decreased in the order caffeic acid > sinapic acid > ferulic acid > ferulic acid esters > p-coumaric acid. In bulk methyl linoleate, test hydroxycinnamic acids and ferulic acid esters showed antioxidant activity in parallel with their radical scavenging activity. In an ethanol-buffer solution of linoleic acid, the activity of test compounds was not always associated with their radical scavenging activity. Ferulic acid was most effective among the tested phenolic acids. Esterification of ferulic acid resulted in increasing activity. The activity of alkyl ferulates was somewhat influenced by the chain length of alcohol moiety. When the inhibitory effects of alkyl ferulates against oxidation of liposome induced by AAPH were tested, hexyl, octyl, and 2-ethyl-1-hexyl ferulates were more active than the other alkyl ferulates. Furthermore, lauryl gallate is most effective among the tested alkyl gallates. These results indicated that not only the radical scavenging activity of antioxidants, but also their affinity with lipid substrates, might be important factors in their activity.  相似文献   

7.
Conjugated linoleic acids (CLA) have shown diverse biological activities, including anti-carcinogenic, anti-atherosclerotic, anti-adipogenic, and anti-diabetogenic effects. Recent reports also showed that CLA has free radical scavenging capacity, which may give health benefits to human beings. However, the application of CLA as a bioactive ingredient has been limited due to its insolubility in water. To overcome this problem, we investigated antioxidant activities of arginine (Arg)-CLA, a water-soluble CLA salt, using both 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assays. CLA, Arg, and Arg-CLA all exerted radical scavenging activities in a dose-dependent manner in both assays. Arg-CLA at 20 mM scavenged 89 and 55% of ABTS and DPPH radicals in 3 h, respectively, whereas CLA alone quenched only 48 and 26% of them under the same conditions. The antioxidant activity of the Arg-CLA complex was found to be synergistic in ABTS assay and comparable to that of vitamin E in DPPH assay.  相似文献   

8.
Eight avenanthramides, amides of anthranilic acid (1) and 5-hydroxyanthranilic acid (2), respectively, and the four cinnamic acids p-coumaric (p), caffeic (c), ferulic (f), and sinapic (s) acid, were synthesized for identification in oat extracts and for structure-antioxidant activity studies. Three compounds (2p, 2c, and 2f) were found in oat extracts. As assessed by the reactivity toward 1,1-diphenyl-2-picrylhydrazyl (DPPH), all avenanthramides except 1p showed activity. Initially, the antioxidant activity of the avenanthramides decreased in a similar order as for the corresponding cinnamic acids, that is: sinapic > caffeic > ferulic > p-coumaric acid. The avenanthramides derived from 2 were usually slightly more active than those derived from 1. All avenanthramides inhibited azo-initiated peroxidation of linoleic acid. 1c and 1s were initially the most effective compounds. The relative order of antioxidant activities was slightly different for the DPPH and the linoleic acid assays run in methanol and chlorobenzene, respectively.  相似文献   

9.
The protein from the seeds of melinjo ( Gnetum gnemon ) was purified using a precipitation method and ion exchange chromatographic techniques to identify the potent antioxidant and free radical scavenging activities. Two antioxidant protein fractions were isolated from G. gnemon seed with molecular weights of approximately 30 kDa (Gg-AOPI) and 12 kDa (Gg-AOPII) by SDS-PAGE. The N-terminal amino acid sequence of Gg-AOPII is Gly-Asn-Gly-Lys-Ala-Thr-Val-Ala-Ile-Leu-Val-Lys-Glu-Lys-Val-Glu-Tyr-Gly-Glu-Glu, and the result of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) analysis showed that they were distinct from each other; no protein in database matching was found to both Gg-AOPI and Gg-AOPII. The antioxidant or free radical scavenging activities of Gg-AOPs were investigated by employing in vitro assay systems including the inhibition of linoleic acid autoxidation, scavenging effect on α,α-diphenyl-β-picrylhydrazyl free radical (DPPH), 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), reducing power, chelating abilities of metal ions Cu(2+) and Fe(2+), and protections against hydroxyl radical-mediated DNA damages. The result showed that two protein fractions exhibited significant (p < 0.05) antioxidant activities against free radicals such as DPPH, ABTS, and superoxide anion and showed activities similar to those of glutathione (G-SH) and BHT in a linoleic acid emulsion assay system. Moreover, Gg-AOPI and Gg-AOPII also exhibited notable reducing power and strong chelating effect on Fe(2+) and protected hydroxyl radical induced oxidative DNA damage. The data obtained by the in vitro systems obviously established the antioxidant potency of Gg-AOPs.  相似文献   

10.
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.  相似文献   

11.
The chemistry behind antioxidant capacity assays   总被引:3,自引:0,他引:3  
This review summarizes the multifaceted aspects of antioxidants and the basic kinetic models of inhibited autoxidation and analyzes the chemical principles of antioxidant capacity assays. Depending upon the reactions involved, these assays can roughly be classified into two types: assays based on hydrogen atom transfer (HAT) reactions and assays based on electron transfer (ET). The majority of HAT-based assays apply a competitive reaction scheme, in which antioxidant and substrate compete for thermally generated peroxyl radicals through the decomposition of azo compounds. These assays include inhibition of induced low-density lipoprotein autoxidation, oxygen radical absorbance capacity (ORAC), total radical trapping antioxidant parameter (TRAP), and crocin bleaching assays. ET-based assays measure the capacity of an antioxidant in the reduction of an oxidant, which changes color when reduced. The degree of color change is correlated with the sample's antioxidant concentrations. ET-based assays include the total phenols assay by Folin-Ciocalteu reagent (FCR), Trolox equivalence antioxidant capacity (TEAC), ferric ion reducing antioxidant power (FRAP), "total antioxidant potential" assay using a Cu(II) complex as an oxidant, and DPPH. In addition, other assays intended to measure a sample's scavenging capacity of biologically relevant oxidants such as singlet oxygen, superoxide anion, peroxynitrite, and hydroxyl radical are also summarized. On the basis of this analysis, it is suggested that the total phenols assay by FCR be used to quantify an antioxidant's reducing capacity and the ORAC assay to quantify peroxyl radical scavenging capacity. To comprehensively study different aspects of antioxidants, validated and specific assays are needed in addition to these two commonly accepted assays.  相似文献   

12.
In this study was analyzed the effect of crop year and harvesting time on the fatty acid composition of cv. Picual virgin olive oil. The study was carried out during the fruit ripening period for three crop seasons. The mean fatty acid composition of Picual oils was determined. The oils contained palmitic acid (11.9%), oleic acid (79.3%), and linoleic acid (2.95%). The content of palmitic acid and saturated fatty acids decreased during fruit ripening while oleic and linoleic acids increased. The amount of stearic and linolenic acids decreased. The amount of saturated acids, palmitic and stearic, and the polyunsaturated acids linoleic and linolenic was dependent on the time of harvest, whereas the amount of oleic acid varied with the crop year. The differences observed between crop years for both palmitic and linoleic acid may be explained by the differences in the temperature during oil biosynthesis and by the amount of summer rainfall for oleic acid content. A significant relationship was observed between the MUFA/PUFA ratio and the oxidative stability measured by the Rancimat method.  相似文献   

13.
This article investigated the mycochemical profiles and the antioxidant activities of the lipophilic extracts of the white and brown button mushrooms. We found that only free ergosterols were present in both mushrooms at 2.04-4.82 mg/g dry matter (DM). Ergosterol concentration was higher in early growth stages but decreased as the mushrooms grew, and it distributed evenly between the caps and stems during early developmental stages but accumulated more in the caps after maturation. The photochemiluminescence (PCL) values of the two mushrooms were 5.49-10.48 nmol trolox equivalent/mg DM, and the EC50 values of 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay ranged 20.19-41.49 mg DM/μg DPPH. The ergosterol content positively correlated with the antioxidant activities (r2>0.89). The total fatty acid content was 8.7 mg/g DM in the white and 5.1 mg/g DM in the brown button mushroom and contained mainly linoleic, palmitic, and stearic acids. Our data provide guidance for optimized harvesting time of mushrooms and maximized health benefits.  相似文献   

14.
The antioxidant activity of essences of teas prepared from mulberry ( Morus alba L.), Camellia sinensis L., and Cudrania tricuspidata (Carr.) Burea plant was examined using two antioxidant assays. Selected volatile chemicals identified in these plants were also tested for antioxidant activity. All extracts exhibited antioxidant activity with a clear dose response in the aldehyde/carboxylic acid and the malonaldehyde/gas chromatography (MA/GC) assays. Antioxidant activity of extracts at the level of 500 μg/mL ranged from 77.02 ± 0.51% (stems of Burea plant) to 52.57 ± 0.92% (fermented tea of Camellia and stems of Mulberry tea) in the aldehydes/carboxylic acid assay. Their antioxidant activity at the level of 160 μg/mL ranged from 76.17 ± 0.27% (roots of Burea plant) to 59.32 ± 0.27% (stems of Mulberry tea) in the MA/GC assay. Among the positively identified compounds (11 terpenes and terpenoids, 15 alkyl compounds, 26 nitrogen containing heterocyclic compounds, 9 oxygen containing heterocyclic compounds, 18 aromatic compounds, 7 lactones, 6 acids, and 4 miscellaneous compounds), eugenol, 2,5-dihydroxyl acetophenone, and isoeugenol exhibited antioxidant activity comparable to that of BHT in both assays. Vanillin and 2-acetylpyrrole showed potent antioxidant activity in the aldehydes/carboxylic acid assay but only moderate activity in the MA/GC assay. These results suggest that consumption of antioxidant-rich beverages prepared from these plants may be beneficial to human health.  相似文献   

15.
Three tests of increasing complexity were used to assess the antioxidant activity of five synthetic gallic esters of sucrose bearing 3, 6, 7, or 8 galloyl units. In addition, two of these compounds had 1 or 2 hydrocarbon (C10-C12) acyl chains. Reaction with the DPPH radical led to the evaluation of the number of radicals trapped per galloyl unit n (3-4), as well as the apparent second-order rate constant for H atom donation k (1200-1500/M/s). These results indicated similar contribution and reactivity of all the galloyl units. Inhibition of the AAPH-initiated peroxidation of linoleic acid in a micellar medium confirmed the additive contribution of the galloyl units, whereas the presence of the hydrocarbon acyl chains had no influence. These results suggest an inhibition of initiation at high antioxidant levels and an underlying prooxidant effect of the galloyl radicals at low concentrations. Finally, LDL peroxidation was inhibited in proportion to the number of galloyl units, in agreement with the preceding tests.  相似文献   

16.
The antioxidant and antitumor activities (in vitro) of superfine regular and Se-enriched green tea particles with different sizes (3.52 microm and 220 nm) were investigated in this paper. The vitamin C and tea polyphenol contents of green tea in different sizes were significantly different, and amino acid and chlorophyll just changed a little. The antioxidant activity of green tea particles was evaluated by DPPH radical scavenging and linoleic acid peroxidation inhibition methods, and the antitumor activity was evaluated by antiproliferation assay on HepG2, A549, and MGC803 cells. The results indicated that enrichment of selenium endowed green tea with higher antioxidant activity and antitumor activity on HepG2 and A549 cells but not on MGC803 cells. The DPPH radical scavenging rates of regular and Se-enriched green tea of 220 nm (67.87% and 69.49%, respectively) were significantly greater than that of 3.52 microm, but the inhibition of linoleic acid peroxidation for green tea of 220 nm was lower. The inhibitory rates of green tea of 220 nm on HepG2, A549, and MGC803 cells achieved 77.35%, 80.76%, and 87.54% for regular green tea, and 82.51%, 88.09%, and 74.48% for Se-enriched green tea at the dose of 100 microg mL (-1), values that were all significantly higher compared to that of 3.52 microm.  相似文献   

17.
Antimutagenic and antioxidant properties of milk-kefir and soymilk-kefir   总被引:1,自引:0,他引:1  
This study was aimed at evaluating the antimutagenic and antioxidant properties of milk-kefir and soymilk-kefir. Such antimutagenic activity was determined by means of the Salmonella mutagenicity assay, whereas the antioxidant properties of kefir were evaluated by assessing the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity, lipid peroxidation inhibition activity, ferrous ion chelating ability, reducing power, and antioxidative enzyme activity. Both milk-kefir and soymilk-kefir demonstrated significantly greater antimutagenic activity than milk and soymilk. Milk-kefir and soymilk-kefir also displayed significantly greater scavenging activity upon DPPH radicals, an inhibition effect upon linoleic acid peroxidation, and more substantial reducing power but displayed a reduced glutathione peroxidase activity than was the case for milk and soymilk. Milk and soymilk fermented by kefir grains did not alter the ferrous ion chelating ability and superoxide dismutase activity of the original materials. These findings have demonstrated that milk-kefir and soymilk-kefir possess significant antimutagenic and antioxidant activity and suggest that milk-kefir and soymilk-kefir may be considered among the more promising food components in terms of preventing mutagenic and oxidative damage.  相似文献   

18.
The antioxidant activity of the methanolic extracts of the leaves of 39 plant species was examined. These leaves were collected from the plants growing on subtropical seashores. The activity was evaluated by three kinds of assay methods, which included the DPPH radical scavenging assay, linoleic acid oxidation assay, and oxidative cell death assay. Two extracts from Excoecaria agallocha and Terminalia catappa showed remarkably potent activity in all assay systems. The HPLC analysis of the extracts indicated the presence of the same antioxidant and isolation work for the compound identified ellagic acid. The isolated ellagic acid showed strong antioxidant activity in the assay systems used.  相似文献   

19.
New lipophilic esters of tyrosol, a naturally occurring phenol with interesting biological properties, have been synthesized in good yields by a chemoselective procedure, using lipase from Candida antarctica or p-toluenesulfonic acid as catalysts. Their antioxidant activities have been evaluated by the Rancimat test in lipophilic food matrices, as well as by FRAP and ABTS assays in methanolic solutions, and compared with those of previously synthesized hydroxytyrosyl esters. Free tyrosol, hydroxytyrosol, butylhydroxytoluene, and alpha-tocopherol were used as standards. All methods used for the antioxidant activity evaluation emphasized the high influence of the ortho-diphenolic structure on the antioxidant capacity, tyrosol and its derivatives being less active than hydroxytyrosol and its analogues and even less than BHT and alpha-tocopherol. In addition, the Rancimat test revealed a lower activity for ester derivatives than for their respective reference compounds (HTy or Ty), in agreement with the polar paradox. On the other hand, FRAP and ABTS methods reported an opposite behavior between the synthetic esters and their respective references. Thus, hydroxytyrosyl esters were more active than HTy, whereas tyrosyl esters were less active than Ty. The length and nature of the acyl side chain did not seem to play an important role in the antioxidant activity of either the hydroxytyrosyl or tyrosyl ester series, since no significant differences were observed among them.  相似文献   

20.
Both the pro- and antiradical water soluble activity, toward DPPH(*), ROO(*), OH(*) radicals found in seven diet vegetables belonging to the Cichorium genus, and the effects of boiling, freezing, and freeze-drying on such activities were investigated. The vegetables were three red cultivars of Cichorium intybus var. silvestre from three different areas of production, that is, chicory from Chioggia, Treviso, and Verona, C. intybus var. foliosum (Belgian chicory), C. endivia var. latifolium (escarole), C. endiviavar. crispum ("crispa"), and a hybrid vegetable obtained by the cross between C. intybus var. silvestre and C. endivia var. latifolium (chicory from Castelfranco). The juices obtained by simple centrifugation of vegetables operating at 2 or 25 degrees C and submitted to the thermal technological treatments were assessed for antiradical activity using the DPPH(*) assay, the linoleic acid-beta-carotene system, and the deoxyribose assay. In all three assays used, each vegetable juice was shown to possess antiradical activity; there was a significant level in the C. endivia and the Belgian chicories and higher levels in the red C. intybus vegetables and the hybrid vegetable. All juice behaviors in the linoleic acid-beta-carotene system indicate that they also contain a thermally unstable component, which in a cold medium promptly promoted and accelerated linoleic acid peroxidation, therefore masking the presence of any thermally stable antiperoxyl radical components. The presence of these components, which efficiently protect linoleic acid from peroxidation, can be singled out only after inactivation by heating, or separation by dialysis, of the pro-oxidant components. Dialysis fractions showed that the pro-oxidant component has MW > 50000 Da and that the juices contain a number of antioxidant components which contribute to their antiradical activity.  相似文献   

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