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1.
Magnaporthe grisea is a fungal pathogen of rice that forms appressoria that penetrate the outer cuticle of the rice plant. Data from recent studies indicate that M. grisea isocitrate lyase (ICL), a key enzyme in the glyoxylate cycle, is highly expressed during appressorium-mediated plant infection. Bromophenols isolated from the red alga Odonthalia corymbifera exhibited potent ICL inhibitory activity and blocked appressoria formation by M. grisea in a concentration-dependent manner. In addition, these compounds protected the rice plants from infection by M. grisea. Rice plants infected with wild-type M. grisea Guy 11 exhibited significantly lower disease severity with bromophenol treatment than without, and the treatment effect was comparable to the behavior of the Deltaicl knockout mutant I-10. The protective effect of bromophenols and their strong inhibition of appressorium formation on rice plants suggest that ICL inhibitors may be promising candidates for crop protection, particularly to protect rice plants against M. grisea.  相似文献   

2.
A total of 12 fatty acid esters of Z- and E-p-coumaryl alcohol were isolated from cv. Annurca apple fruit and characterized. This apple variety is widely cultivated in the south of Italy, and the fruits typically undergoe a reddening treatment after harvest. Structures of the p-coumaryl esters were elucidated by GC-MS and (1)H and (13)C NMR after purification of individual compounds by HPLC. It was found that the esters are localized in the fruit peel. During reddening of the fruit, there was a substantial increase in the amount of esters and particularly in molecular species with unsaturated fatty acids. The individual compounds were tested for antioxidant activity, and over half were shown to be at least as effective as alpha-tocopherol.  相似文献   

3.
A German Riesling wine has been fractionated with the aid of countercurrent chromatography. After purification by HPLC, the structures of 101 compounds were established by mass spectrometry and NMR spectroscopy. Seventy-three of the isolated compounds exhibited a phenolic or benzylic structure. Fifty-four compounds were reported for the first time as Riesling wine constituents. New compounds identified in this work included twelve benzoic and cinnamic acid derivatives. In addition to two isomeric (E)-caffeoyl ethyl tartrates, the glucose esters of (E)-cinnamic, (E)-p-coumaric, and (E)-ferulic acid, as well as the 4-O-glucosides of (E)- and (Z)-ferulic acid, have been identified for the first time in Riesling wine. The structures of two additional phenylpropanoids were elucidated as 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-propan-1-one and 2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)-propan-1-one. Moreover, two ethyl esters, i.e., ethyl protocatechuate and ethyl gallate, as well as the glucose ester of vanillic acid, were newly detected in Riesling wine. Novel representatives in the flavonoid group were dihydrokaempferol, dihydroquercetin, and four dihydroflavonol glycoconjugates, i.e., the 3-O-glucosides of dihydrokaempferol and dihydroquercetin, as well as the 3-O-xyloside and the 3'-O-glucoside of dihydroquercetin. Additionally, six novel lignans, i.e., lariciresinol 4-O-glucoside, three isolariciresinol derivatives, and two secoisolariciresinols, as well as three neolignans were isolated. Structural elucidation of the newly isolated wine constituents is reported together with the determination of their antioxidant activity.  相似文献   

4.
The relationship among antioxidant activity, based on the electron-spin resonance determination of the reduction of Fremy's radical, vasodilation activity, and phenolic content was investigated in 16 red wines. The wines were selected to provide a range of origins, grape varieties, and vinification methods. Sensitive and selective HPLC methods were used for the analysis of the major phenolics in red wine: free and conjugated myricetin, quercetin, kaempferol, and isorhamnetin; (+)-catechin, (-)-epicatechin, gallic acid, p-coumaric acid, caffeic acid, caftaric acid, trans-resveratrol, cis-resveratrol, and trans-resveratrol glucoside. Total anthocyanins were measured using a colorimetric assay. The total phenolic content of the wines was determined according to the Folin-Ciocalteu colorimetric assay and also by the cumulative measurements obtained by HPLC. The 16 wines exhibited a wide range in the values of all parameters investigated. However, the total phenol contents, measured both by HPLC and colorimetrically, correlated very strongly with the antioxidant activity and vasodilation activity. In addition, the antioxidant activity was associated with gallic acid, total resveratrol, and total catechin. In contrast, only the total anthocyanins were correlated with vasodilation activity. The results demonstrate that the different phenolic profiles of wines can produce varying antioxidant and vasodilatant activities, which opens up the possibility that some red wines may provide enhanced health benefits for the consumer.  相似文献   

5.
A sulfoglycolipidic fraction (SF) isolated from the red microalga Porphyridium cruentum was analyzed for fatty acid composition and assayed for ability to inhibit, in vitro, the generation of superoxide anion in primed leucocytes and the proliferation of a panel of human cancer cell-lines. Results demonstrated that SF contained large amounts of palmitic acid (26.1%), arachidonic acid (C20: 4 omega-6, 36.8%), and eicopentaenoic (C20:5 omega-3, 16.6%) acids, and noticeable amounts of 16:1n-9 fatty acid (10.5%). It strongly inhibited both the production of superoxide anion generated by peritoneal leukocytes primed with phorbol myristate acetate (IC(50): 29.5 microg/mL), and the growth of human colon adenocarcinoma DLD-1 and to a lesser extent of human breast adenocarcinoma MCF-7, human prostate adenocarcinoma PC-3, and human malignant melanoma M4 Beu cell-lines, and therefore might have a chemopreventive or chemotherapeutic potential, or both. It was found markedly more cytotoxic than sulfoquinovosyldiacylglycerols from plant used as a standard (STD), due to a stronger ability to inhibit DNA alpha-polymerase (IC(50): 378 microg/mL, vs 1784 microg/mL for STD). After a 48-h continuous treatment, IC(50) values for growth inhibition were in the range of 20-46 microg/mL instead of 94 to >250 microg/mL for STD, and those for inhibition of metabolic activity were in the range of 34-87 microg/mL instead of >250 microg/mL for STD. The higher anti-proliferative effect was observed on colon adenocarcinoma DLD-1 cells, and the weaker effect was observed on breast adenocarcinoma MCF-7.  相似文献   

6.
Seventeen Ohio soybeans were screened for isoflavone content and antioxidant activity. Isoflavone content was determined by C(18) reversed phase high-performance liquid chromatography coupled with a photodiode array detector. Antioxidant activities of soybean extracts were measured using 2,2-diphenyl-1-picryl-hydrazyl (DPPH) free radical and photochemiluminescence (PCL) methods. The highest and lowest total isoflavone contents were 11.75 and 4.20 micromol/g soy, respectively, while the average was 7.12 micromol/g soy. Antioxidant activities of soybean extracts ranged from 7.51 to 12.18 micromol butylated hydroxytoluene (BHT) equivalent/g soy using the DPPH method. Lipid and water soluble antioxidant activities of soybean extracts ranged from 2.40 to 4.44 micromol Trolox equivalent/g soy and from 174.24 to 430.86 micromol ascorbic acid equivalent/g soy, respectively, using the PCL method.  相似文献   

7.
为了研究大蒜烯丙基硫化物的抗氧化活性,该文利用离子交换层析与制备液相技术从大蒜中分离得到S-烯丙基-L-半胱氨酸(S-allyl-L-cysteine,SAC)、S-烯丙基-L-半胱氨酸亚砜(S-allyl-L-cysteine sulfoxide,ACSO)和γ-谷氨酰-S-烯丙基-L-半胱氨酸(γ-L-glutamyl-S-allyl-L-cysteine,GSAC)3种水溶性烯丙基硫化物。分离产物利用高效液相色谱-电喷雾离子化串联质谱联用(high performance liquid chromatography-electrospray ionization-mass/mass spectrometry,HPLC-ESI-MS/MS)、核磁共振氢谱(proton nuclear magnetic resonance,1H NMR)和核磁共振碳谱(carbon-13 nuclear magnetic resonance,13C NMR)技术及比旋光度检测方法鉴定,并与合成标准品比对分析确定。同时,该文以具有半胱氨酸结构的还原型谷胱甘肽(glutathione,GSH)为参照测定了SAC、ACSO、GSAC的1,1-二苯基-2-三硝基苯肼(1,1-diphenyl-2-picrylhydrazyl,DPPH)自由基清除能力及铁离子螯合能力。结果表明,SAC和GSAC对DPPH自由基的清除率较高(73.55%,72.68%)且与GSH(71.14%)无显著性差异(P0.05);SAC和ACSO对铁离子的螯合率较高(81.21%,79.18%)且与GSH(78.13%)无显著性差异(P0.05),尤其是GSAC对铁离子螯合率(92.76%)显著性高于GSH(P0.05),证实了3种硫化物均具有很好的抗氧化性能。研究结果进一步解释和阐述大蒜硫化物的螯合能力,进而为大蒜硫化物以抗氧化为基础的其他功能活性研究提供参考。  相似文献   

8.
The objectives of this study were to isolate the antioxidative components in the broth filtrate of Aspergillus candidus (CCRC 31543), to characterize their antioxidative properties, and to evaluate their safety. Three major compounds were isolated and identified as 3,3' '-dihydroxyterphenyllin, 3-hydroxyterphenyllin, and candidusin B. In the linoleic acid peroxidation system, the inhibition of peroxidation in these three compounds was greater than 95% and was significantly higher than that of alpha-tocopherol but equal to that of BHA at 12.5-200 microg/mL. As measured using the Rancimat method in lard, 3,3' '-di-OH-terphenyllin exhibited a protection factor value of 7.82, which was substantially higher than those of BHA (5.58) and alpha-tocopherol (4.29) at 200 microg/mL. 3,3' '-di-OH-terphenyllin and 3-OH-terphenyllin also exhibited marked scavenging effects on the alpha,alpha-diphenyl-beta-picrylhydrazyl radicals (94.7 and 96.0%, respectively), which were similar to those of BHA and alpha-tocopherol. Safety studies showed that these three compounds were neither cyto- nor geno-toxic toward human intestine 407 (INT 407) cells, nor mutagenic toward Salmonella typhimurium TA98 and TA100.  相似文献   

9.
Two compounds recognized as responsible for the insecticidal activity of extracts of Calceolaria andina L. (Scrophulariaceae) have been isolated and characterized as 2-(1, 1-dimethylprop-2-enyl)-3-hydroxy-1,4-naphthoquinone and the corresponding acetate, 2-acetoxy-3-(1,1-dimethylprop-2-enyl)-1, 4-naphthoquinone. Their activities against 29 pest species and 9 beneficial species of arthropod from a total of 11 orders have been determined. Activities against homopteran and acarine species are of the same order as those of established pesticides, and, significantly, no cross-resistance is observed for strains resistant to established classes of insecticide. Mammalian toxicities are low.  相似文献   

10.
Defatted peanut meal hydrolysate (DPMH) was purified using ultrafiltration, gel filtration chromatography, and high-performance liquid chromatography. A tripeptide with strong oxygen radical absorbance capacity (ORAC) was isolated and identified as Tyr-Gly-Ser by ESI-MS/MS. It was then synthesized to measure its antioxidant properties in different systems. The ORAC value of Tyr-Gly-Ser was 3-fold higher than that of glutathione (GSH), and it displayed a stronger protective effect on linoleic acid peroxidation and H(2)O(2)-induced oxidative injury in rat pheochromocytoma line PC12 cells than GSH (p < 0.05). However, Tyr-Gly-Ser showed negligible DPPH radical scavenging activity, reducing power, and no metal chelating ability. The results suggested that Tyr-Gly-Ser displayed antioxidant activity via the hydrogen atom transfer mechanism, and the Tyr at the N-terminal was the hydrogen donor. The ORAC assay was recommended as a reliable and effective method to measure the antioxidant activity in the course of antioxidant peptide isolation.  相似文献   

11.
Daylily (Hemerocallis spp.) flowers are utilized as an important ingredient in traditional Asian cuisine and are also valued for their reputed medicinal effects. In studies of the bioactive methanol and aqueous methanol extracts of lyophilized Hemerocallis cv. Stella de Oro flowers, kaempferol, quercetin, and isorhamnetin 3-O-glycosides (1-9), phenethyl beta-D-glucopyranoside (10), orcinol beta-D-glucopyranoside (11), phloretin 2'-O-beta-D-glucopyranoside (12), phloretin 2'-O-beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside (13), a new naphthalene glycoside, stelladerol (14), and an amino acid (longitubanine A) (15) have been isolated. All of these compounds were tested for their antioxidant and cyclooxygenase inhibitory activities. Stelladerol was found to possess strong antioxidant properties, inhibiting lipid oxidation by 94.6% +/- 1.4 at 10 microM in an in vitro assay. Several of the flavonol 3-O-glycoside isolates also demonstrated modest antioxidant activities at 10 microM. None of the isolates inhibited cyclooxygenase activity at 100 microM.  相似文献   

12.
Using an oxygen radical absorbance capacity (ORAC) assay, antioxidant activity was detected in the ethanol extract of the Pacific oyster, which was purified by sequential extraction with organic solvents. The ethyl acetate fraction showed the strongest antioxidant activity and was further purified, yielding a single compound [as assessed by thin-layer chromatography (TLC) and reverse-phase high-performance liquid chromatography (HPLC)]. This compound was identified as 3,5-dihydroxy-4-methoxybenzyl alcohol on the basis of (1)H and (13)C nuclear magnetic resonance (NMR), heteronuclear multiple-bond correlation (HMBC), and electrospray ionization-mass spectrometry (ESI-MS) spectral analyses, a conclusion that was confirmed by chemical synthesis. The concentration of the compound was 6.7 mg/100 g of whole oyster meat wet weight. This amphiphilic antioxidant retarded the copper-mediated oxidation of low-density lipoproteins (LDLs) and the generation of thiobarbituric acid reactive substances. Furthermore, the compound showed substantial antioxidant activity using the ORAC and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assays compared to natural antioxidants. Although the same compound was previously found in brown algae, its presence in other organisms and antioxidant activity are reported here for the first time.  相似文献   

13.
Peroxynitrite (ONOO(-)), formed from the reaction of superoxide (O(2)*(-)) and nitric oxide (*NO), is a cytotoxic species that can oxidize several cellular components such as proteins, lipids, and DNA. It has been implicated in diseases such as Alzheimer's disease, rheumatoid arthritis, cancer, and atherosclerosis. Due to the lack of endogenous enzymes responsible for ONOO(-) inactivation, developing a specific ONOO(-) scavenger is of considerable importance. The aim of this study was to evaluate the ability of marine natural products to scavenge ONOO(-) and to protect cells against ONOO(-). Methanolic extracts of 17 marine alga were tested for their ONOO(-) scavenging activity. Among them, Symphyocladia latiuscula showed the potent scavenging activity. CH(2)CH(2) fraction was partitioned with CH(2)CH(2) following n-hexanal extraction from the methanol extract of S. latiuscula. It was highly effective for ONOO(-) scavenging activity. Further analysis of the active fractionated extract identified 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether (TDB) as a potent ONOO(-) scavenger. The data demonstrated that TDB led to decreased ONOO(-)-mediated nitration of tyrosine through electron donation. TDB showed significant inhibition on nitration of bovine serum albumin and low-density lipoprotein by ONOO(-) in a dose-dependent manner. It also provided cytoprotection from cell damage induced by ONOO(-). TDB can be developed as an effective peroxynitrite scavenger for the prevention of the involved diseases.  相似文献   

14.
Antifungal activity of hexane, ethyl acetate and methanol extracts of Parmelia reticulata was evaluated against soilborne pathogenic fungi, namely, Sclerotium rolfsii, Rhizoctonia solani, R. bataticola, Fusarium udum, Pythium aphanidermatum and P. debaryanum by poisoned food technique. Maximum antifungal activity was exhibited by hexane and ethyl acetate extracts against most of the test pathogens. Secondary metabolites, namely, (±)-isousnic acid, (±)-protolichesterinic acid, atranorin, evernyl, ethyl hematommate, ethyl orsellinate, methyl hematommate (3-formyl-2,4-dihydroxy-6-methylbenzoic acid methyl ester), 2-hydroxy-4-methoxy-3,6-dimethylbenzoic acid, 1-hydroxy-3,6-dimethoxy-8-methyl-xanthen-9-one, baeomycesic acid and salazinic acid, were isolated from the above extracts and identified by 1H NMR, 13C NMR and mass spectroscopic methods. When these metabolites were tested for antifungal activity against test pathogens, maximum antifungal activity was exhibited by (±)-protolichesterinic acid against R. solani (ED50=23.09 μg mL(-1)) and P. debaryanum (ED50=16.07 μg mL(-1)) and by atranorin against S. rolfsii (ED50=39.70 μg mL(-1)). The antifungal activity of protolichesterinic acid was found to be comparable to that of hexaconazole, a commercial fungicide.  相似文献   

15.
Two newly formed yellow pigments that revealed unique spectral features were detected and isolated from an aged Port red wine by TSK Toyopearl HW-40(s) gel chromatography and characterized by UV-visible spectrophotometry, 1H NMR and 13C NMR, and mass spectrometry (LC-ESI/MS). The UV-vis spectra of these pigments showed maximum absorption at 478 nm that is significantly hypsochromically shifted from those of original grape anthocyanins and other pyranoanthocyanins, exhibiting a more yellow hue in acidic solution. The structures of these pigments correspond to methyl-linked pyranomalvidin 3-glucoside and its respective coumaroyl glucoside derivative. They were shown to arise from the reaction between acetoacetic acid and genuine grape anthocyanins. Isolation and NMR identification using 1D and 2D NMR techniques are reported for the first time for this new family of anthocyanin-derived yellow pigments occurring in red wines.  相似文献   

16.
trans-Piceid and trans-resveratrol were authenticated for the first time by high-resoution mass spectrometry in red sorghum grains. A 0.4-1 mg/kg amount of trans-piceid and up to 0.2 mg/kg trans-resveratrol were quantified by reversed phase high-performance liquid chromatography-atmospheric pressure chemical ionization(+)-tandem mass spectrometry. The white sorghum samples contained only traces of trans-piceid (up to 0.1 mg/kg), and trans-resveratrol was absent. In much lower amounts than procyanidins, stilbenoids are not able to contribute significantly to the exceptional antioxidant activity of red sorghum (ORAC, 83-147 μmol TE/g; AAPH, 0.61-1.79 min/mg kg(-1)). More than 10 mg/kg of total stilbenoids have been reported in some hop varieties. Yet, as hop is a minor wort ingredient as compared to cereals, red sorghum could be the main source of trans-piceid in beer. Hop remains, however, the single source of cis-piceid.  相似文献   

17.
The moderate consumption of alcoholic beverages has been associated with protection against the development of coronary heart disease. Although alcohol itself can help prevent coronary heart disease through a number of mechanisms, red wine appears to offer protection above and beyond that attributable to alcohol alone. Red wine is a complex fluid containing grape, yeast, and wood-derived phenolic compounds, the majority of which have been recognized as potent antioxidants. The aim of this study was to investigate the major phenolic contributors to the antioxidant activity of wine. To this end, four wines were followed during the first 7-9 days of vinification. Individual phenolic compounds were quantified by HPLC, and antioxidant activity was determined by electron spin resonance spectroscopy. The extraction of the phenolics was found to be influenced by vinification procedure, grape quality, and grape variety. Although fermenting wines reached a total phenolic content comparable to that of a bottled wine after 9 days of vinification, the antioxidant activity was significantly lower than that of a finished wine. This suggests that the larger polyphenolic complexes and condensation products that appear during aging make a sizable contribution to the overall antioxidant activity of red wines.  相似文献   

18.
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   

19.
The study of the antioxidant capacity of foodstuffs requires the use of diverse determination methods to gain a wider picture of their multiple effects. The aim of this work was to evaluate the "antioxidant profile" of red wines applying TAC (total antioxidant capacity) methods: 2,2'-azinobis(3-ethyl-benzthiazoline-6-sulfonic acid) (ABTS), 2,2-diphenyl-1-picrylhydrazyl, N,N-dimethyl-p-phenylenediamine dihydrochloride, oxygen radical absorbance capacity, ferric reducing/antioxidant power, hydroxyl and superoxide radical scavenger activities, and biomarkers of oxidative stress methods such as lipid peroxidation inhibition and inhibition of damage to DNA. Furthermore, levels of total polyphenols (TPP) of wines were also evaluated. Three bottles of 107 different Spanish red wines (total samples 321), made from different grape varieties, aging processes, and vintages, were analyzed. The validation of TAC methods, the first step in this work, provided a good linearity, proportionality, and low detection limits. Among these methods, the ABTS was the most satisfactory for its rapidity, cost, and precision. All wines showed an important capacity to scavenge hydroxyl radicals and were capable of blocking superoxide radicals but with 10 times lower intensity. Wines also showed important protective action on biomarkers of oxidative stress; they were much more active to inhibit lipid peroxidation than DNA oxidation. Few statistically significant correlations among levels of TPP and antioxidant properties of wines were detected. Furthermore, values of these correlations were very low.  相似文献   

20.
Eight commercial Italian vini novelli (red wines prepared by carbonic maceration and supposed to be consumed within three months from their wine-making) were evaluated for their total antioxidant activity. The wines had an average total phenol content (1605.4 +/- 337.4 mg/L gallic acid equivalents) lower than that of wines prepared by traditional maceration and consumable after aging (2057. 3 +/- 524.0 mg/L gallic acid equivalents). The average flavanol content (424.7 +/- 121.3 mg/L catechin equivalents) and the total antioxidant activity (16.8 +/- 3.8 mmol/L Trolox equivalents) of vini novelli were higher than the corresponding values (382.7 +/- 174.5 mg/L catechin equivalents and 12.3 +/- 3.3 mmol/L Trolox equivalents) found for aged wines. Three couples of experimental wines were prepared from the same grapes by traditional or carbonic maceration. These wines showed a different phenolic pattern, anthocyanins being more abundant in vini novelli. However, the average total antioxidant activities of the wines were similar, suggesting that aging (and not the wine-making technique) is the main factor influencing the antioxidant activity of red wines.  相似文献   

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