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1.
The oxidative metabolism of the major soy isoflavones daidzein and genistein was investigated using liver microsomes from Aroclor-treated male Wistar rats. Both daidzein and genistein were extensively metabolized and are therefore excellent substrates for cytochrome P450 enzymes. The identity of the metabolites was elucidated using high-performance liquid chromatography (HPLC) with diode array detection, gas chromatography-mass spectrometry (GC/MS), and HPLC/atmospheric pressure ionization electrospray mass spectrometry (API-ES MS) as well as reference substances. Daidzein was converted to nine metabolites, comprising four monohydroxylated, four dihydroxylated, and one trihydroxylated metabolite. Genistein was metabolized to four monohydroxylated and two dihydroxylated products. With both isoflavones the additional hydroxy groups are exclusively introduced into the ortho positions of existing phenolic hydroxy groups. The major metabolites of daidzein were identified as 6,7,4'-trihydroxyisoflavone, 6,7,3',4'-tetrahydroxyisoflavone, 7,8, 4'-trihydroxyisoflavone, and 5,6,7,4'-tetrahydroxyisoflavone. The main microsomal metabolites of genistein were 5,6,7, 4'-tetrahydroxyisoflavone and 5,7,8,4'-tetrahydroxyisoflavone. Furthermore, the GC/MS and HPLC/API-ES MS analysis support the conclusion that one monohydroxylated metabolite of daidzein and genistein is hydroxylated at the aliphatic position C-2 of the C-ring. The UV-vis, GC/MS, and HPLC/MS data of all detected metabolites as well as the derived chemical structure of the metabolites are presented. Most metabolites are reported in this paper for the first time. On the basis of these findings it is suggested that hydroxylation reactions may also play an important role in the in vivo metabolism of the soy isoflavones daidzein and genistein.  相似文献   

2.
采用穗培养技术在7个氮素(NH4NO3为氮源)浓度水平(N1:0mg/L;N2:412.5 mg/L;N3:825.0mg/L;N4:1237.5mg/L;N5:1650.0ms/L;N6:3300.0mg/L;N7:4950.0mg/L)下研究了氮素对2个大麦品种籽粒中酚酸和蛋白质含量的影响.结果表明,在高氮水平(N...  相似文献   

3.
Abstract

Analytical procedures using gas chromatography–ion trap tandem mass spectrometry (GC‐MS/MS) were developed to analyze atrazine (ATR) and its dealkylated metabolites in four forage species (switchgrass, tall fescue, smooth bromegrass, and orchardgrass). Atrazine, deethylatrazine (DEA), and deisopropylatrazine (DIA) were extracted with methanol (CH3OH) followed by liquid–liquid extraction and partitioning into chloroform, with additional cleanup by C18 solid‐phase extraction (SPE). Through the optimization of ionization conditions and ion storage voltages, the background noise of product ion spectra (MS/MS) was reduced dramatically, providing sub‐µg/kg detection limits. Mean recoveries of ATR, DEA, and DIA were 94.3, 105.6, and 113.1%, respectively. The estimated limit of detection (LOD) was 0.6 µg/kg for ATR, 1.3 µg/kg for DEA, and 0.3 µg/kg for DIA. These LODs were one to two orders of magnitude lower than those reported for other GC‐MS, GC‐MS/MS, high pressure liquid chromatography (HPLC)‐UV, or HPLC‐MS/MS procedures designed for food‐safety monitoring purposes. To validate the developed method, a field experiment was carried out utilizing three replications of four forage treatments (orchardgrass, tall fescue, smooth bromegrass, and switchgrass). Forage plants were sampled for analyses 25 days after atrazine application. DEA concentrations in C3 grasses ranged from 47 to 96 µg/kg, about 10‐fold higher than in switchgrass, a C4 species. The ATR and DIA concentrations were similar, ranging from 1.5 to 13.2 µg/kg. The developed method provided sufficient sensitivity to determine the fate of ATR and its chlorinated metabolites via plant uptake from soil or dealkylation within living forage grasses. It also represented significant improvements in sensitivity compared to previous GC methods.  相似文献   

4.
Hepatic microsomes from aroclor-treated male Wistar rats biotransform enterolactone to 12 metabolites, six of which carry an additional hydroxy group at the aromatic and six at the aliphatic moiety according to HPLC/MS and GC/MS analysis. The aromatic hydroxylation products were identified with the help of synthesized reference compounds as enterolactone monohydroxylated in the para position and in both ortho positions of the original phenolic hydroxy group of either aromatic ring. The synthesis of the reference compounds and their spectroscopic characterization is described. Enterodiol is metabolized by hepatic microsomes from aroclor-treated male rats to three aromatic and four aliphatic monohydroxylated metabolites. Aromatic hydroxylation occurs in the para position and the two ortho positions of the original phenolic hydroxy group. Most of the metabolites of enterolactone and enterodiol were also formed with microsomes from uninduced rat, pig, and human liver, suggesting that oxidative metabolism is a common feature in the disposition of these lignans in the mammalian organism.  相似文献   

5.
Human bioavailability of curcumin from breads enriched with 1 g/portion of free curcumin (FCB), encapsulated curcumin (ECB), or encapsulated curcumin plus other polyphenols (ECBB) was evaluated. Parental and metabolized curcuminoids and phenolic acids were quantified by HPLC/MS/MS in blood, urine, and feces collected over 24 h. The concentrations of serum curcuminoids were always below 4 nmol/L and those of glucuronides 10-fold less. Encapsulation delayed and increased curcuminoid absorption as compared to the free ingredient. Serum and urinary concentrations of ferulic and vanillic acid were between 2- and 1000-fold higher than those of curcuminoids, with ECBB eliciting the highest amounts. Fecal curcuminoids were 6-fold more abundant after ECB than FCB, while phenolic acids after ECBB quadruplicated those after ECB. Curcuminoid encapsulation increased their bioavailability from enriched bread, probably preventing their biotransformation, with combined compounds slightly reducing this effect. Phenolic acids are the major metabolites of curcuminoids and may contribute to their biological properties.  相似文献   

6.
The phenolic content of lavandin waste obtained after the distillation of essential oils for the perfume industry was investigated to find an alternative use for this material. The antioxidant activity of different fractions as well as their total phenolic content were evaluated by different methods. Twenty-three phenolic compounds were identified by liquid chromatography coupled to ionspray mass spectrometry (LC/MS/MS), including phenolic acids, hydroxycinnamoylquinic acid derivatives, glucosides of hydroxycinnamic acids, and flavonoids, none of which have previously been reported in lavandin waste. Some structure-activity relationships were proposed by relating the type of scavenging activity of different fractions with the identified phenolic compounds. Contents of representative phenolic acids of Lamiaceae (chlorogenic and rosmarinic) were evaluated by high performance liquid chromatography-diode array detection (HPLC-DAD) and compared with those of other plant species.  相似文献   

7.
Volatiles from stored Kuerle fragrant pears (Pyrus serotina Reld) were studied using high-resolution gas chromatography and the solid-phase microextraction (SPME) method of gas chromatography/mass spectrometry (GC/MS). The dominant components were hexanal, ethyl hexanoate, ethyl butanoate, ethyl acetate, hexyl acetate, ethanol, alpha-farnesene, butyl acetate, and ethyl (E,Z)-2,4-decadienoate. By using GC-olfactometry, it demonstrated that the volatile compounds from SPME were responsible for the aroma of the Kuerle fragrant pear. The levels of sugars, organic acids, and phenolic acids in Kuerle fragrant pears were investigated using high-performance liquid chromatography (HPLC). Fructose was the dominant sugar, followed by glucose and sucrose. With increasing storage time, sucrose levels decreased; however, changes in fructose and glucose levels were not remarkable. There was a slight decrease in flesh firmness during storage. The general soluble solids concentration (SSC) declined slightly after 5 months storage. Some aroma-related volatile components increased during storage, while others decreased, especially the esters. The organic acids and phenolic acids also changed. The flavor of the Kuerle fragrant pears was affected by the change of volatile compounds and changes in chemical and physical properties.  相似文献   

8.
Laboratories devoted to the public health field have to face the analysis of a large number of organic contaminants/residues in many different types of samples. Analytical techniques applied in this field are normally focused on quantification of a limited number of analytes. At present, most of these techniques are based on gas chromatography (GC) or liquid chromatography (LC) coupled to tandem mass spectrometry (MS/MS). Using these techniques only analyte-specific information is acquired, and many other compounds that might be present in the samples would be ignored. In this paper, we explore the potential of time-of-flight (TOF) MS hyphenated to GC or LC to provide additional information, highly useful in this field. Thus, all positives reported by standard reference targeted LC-MS/MS methods were unequivocally confirmed by LC-QTOF MS. Only 61% of positives reported by targeted GC-MS/MS could be confirmed by GC-TOF MS, which was due to its lower sensitivity as nonconfirmations corresponded to analytes that were present at very low concentrations. In addition, the use of TOF MS allowed searching for additional compounds in large-scope screening methodologies. In this way, different contaminants/residues not included in either LC or GC tandem MS analyses were detected. This was the case of the insecticide thiacloprid, the plant growth regulator paclobutrazol, the fungicide prochloraz, or the UV filter benzophenone, among others. Finally, elucidation of unknowns was another of the possibilities offered by TOF MS thanks to the accurate-mass full-acquisition data available when using this technique.  相似文献   

9.
酚酸类和萜类是水稻化感作用研究中研究较多、争议较大的2大类化感物质,但目前有关水稻根系分泌物的研究多在实验室条件下进行。本文以国际公认的强化感水稻‘PI312777’和弱化感水稻‘Lemont’为材料,以未种植水稻的土壤为对照,研究了其在田间旱育条件下,不同土壤水分状态(旱地和湿地)时,根际土壤酚酸类和萜类物质的差异。结果表明,不同水分条件下不同化感潜力水稻品种和对照根际土壤中酚酸类物质和萜类物质的组成较为相似,但各物质含量存在一定差异。适度旱胁迫下,各处理根际土壤中所检测到的咖啡酸、对羟基苯甲酸、香草酸、阿魏酸和肉桂酸5种酚酸类物质及总量均有提高,其中强化感水稻‘PI312777’根际土壤中5种酚酸类物质提高最显著,比CK湿地处理提高2.84倍;在各处理根际土壤共检测到的27种萜类物质中,17种是含氧单萜;干旱胁迫导致各处理根际土壤单萜烯、含氧单萜、含氧倍半萜和总萜变化程度和变化趋势不同,单萜烯相对含量在强化感水稻‘PI312777’根际土壤中明显提高,而在弱化感水稻‘Lemont’和对照根际土壤中则降低。本文在此基础上讨论了由此导致2种水稻田间化感抑草效果差异的原因与机制。  相似文献   

10.
"Long-storage" tomato ( Solanum lycopersicum L.) is a niche product typical of the Mediterranean area, traditionally cultivated under no water supply, the fruits of which combine a good taste with excellent nutritional properties. High-performance liquid chromatography coupled with diode array detection and electron spray-mass spectrometry (HPLC/DAD/ESI-MS) was used to identify the phenolic profile in 10 landraces of long-storage tomato, grown under a typical semiarid climate, as compared to a processing tomato hybrid cultivated in the same environment, under both well-irrigated and unirrigated conditions. Sixteen different secondary metabolites, belonging to the classes of cinnamoylquinic acids and flavonoids, were identified. Quantitative analyses were also performed to monitor the changes in the phenolic content along the batch. The results highlighted that landraces originating from the same area exhibit different fruit morphologies but own a similar biochemical profile. Moreover, the two controls (well irrigated and unirrigated) are placed into the same cluster, suggesting that these secondary metabolites in tomato fruits may be more genetics-dependent than environment-dependent. Given the analysis of phenols nowadays represents a useful tool to assess the genetic variability in tomato, these compounds could be adopted as chemotaxonomic markers in the traceability of this niche product.  相似文献   

11.
A sensitive method is described for the determination and confirmation of zeranol and zearalenone, as well as their isomers and metabolites, in edible animal tissue. The analytes are extracted from tissue with methanol, hydrolyzed enzymatically, cleaned up by acid-base partitioning, determined by liquid chromatography (LC) with electrochemical (EC) detection, and confirmed by gas chromatography/mass spectrometry (GC/MS). LC analysis is performed by isocratic elution with a buffered mobile phase using a Nova-Pak reverse-phase C18 column with amperometric EC detection at +0.90 V. Capillary GC/MS analysis of the trimethylsilyl derivatives provides mass spectral confirmations.  相似文献   

12.
Deodorization of swine manure using minced horseradish roots and peroxides   总被引:1,自引:0,他引:1  
Public concerns about offensive odors from livestock manures are on the rise and so is the pressure to develop practical ways to reduce the odors. The use of minced horseradish (Armoracia rusticanaL) roots (1:10 w/v plant tissue to swine slurry ratio), with calcium peroxide (CaO2 at 26 or 34 mM) or hydrogen peroxide (H2O2 at 34, 52, or 68 mM) for the deodorization of swine manure, was evaluated through a series of laboratory experiments. The principle underlying this deodorization method is the oxidation of odorants by the concerted action of horseradish peroxidase (present in the plant tissue) and peroxide that serves as an electron acceptor, followed by polymerization of phenolic odorants with a possible copolymerization or adsorption of other odorant compounds. The deodorization effect was assessed by a human panel and gas chromatography (GC). In the case of the GC method, 12 compounds commonly associated with malodor (7 volatile fatty acids or VFAs, 3 phenolic compounds, and 2 indolic compounds) were used as odor indicators. Malodor assessment of the treated slurry by a human panel indicated a 50% reduction in odor intensity. GC results showed 100% removal of all phenolic odorants without reoccurrence for at least 72 h. In view of these data, using plant materials as enzyme carriers and peroxides as electron acceptors emerges as an effective approach to phenolic odor control in animal manure.  相似文献   

13.
Lychnophora ericoides Mart. (Asteraceae, Vernonieae) is a plant, endemic to Brazil, with occurrence restricted to the "cerrado" biome. Traditional medicine employs alcoholic and aqueous-alcoholic preparations of leaves from this species for the treatment of wounds, inflammation, and pain. Furthermore, leaves of L. ericoides are also widely used as flavorings for the Brazilian traditional spirit "cacha?a". A method has been developed for the extraction and HPLC-DAD analysis of the secondary metabolites of L. ericoides leaves. This analytical method was validated with 11 secondary metabolites chosen to represent the different classes and polarities of secondary metabolites occurring in L. ericoides leaves, and good responses were obtained for each validation parameter analyzed. The same HPLC analytical method was also employed for online secondary metabolite identification by HPLC-DAD-MS and HPLC-DAD-MS/MS, leading to the identification of di- C-glucosylflavones, coumaroylglucosylflavonols, flavone, flavanones, flavonols, chalcones, goyazensolide, and eremantholide-type sesquiterpene lactones and positional isomeric series of chlorogenic acids possessing caffeic and/or ferulic moieties. Among the 52 chromatographic peaks observed, 36 were fully identified and 8 were attributed to compounds belonging to series of caffeoylferuloylquinic and diferuloylquinic acids that could not be individualized from each other.  相似文献   

14.
Allelopathy, secondary metabolite-mediated plant-to-plant interaction, is gaining application in current agricultural science as well as in invasion ecology. However, the role of sorption to soil in modifying the bioavailability of components in complex allelochemical mixtures is still obscure. Hence, the role of preferential sorption to soil in altering the chemical composition of plant exudates was studied in a silt loam soil using representative mixtures of plant phenolic acids, namely, hydroxybenzoic acid, vanillic acid, coumaric acid, and ferulic acid. The experiment was conducted using a batch equilibration technique, and data were fitted to a Freundlich isotherm. The concentration-dependent sorption coefficient (K(d)) at 10 microg mL(-)(1) was used to assess the sorption affinity of phenolic acids across different systems. Along with solid phase dissolution, all of the phenolic acids exhibited strong site-specific sorption, as evident from their nonlinear isotherms. Removal of organic matter substantially decreased the sorption affinity of all phenolic acids. Direct competition for sorption sites was observed even at low concentrations of phenolic acids. The K(d) of hydroxybenzoic acid was decreased more than 90% in the presence of coumaric acid. About 95% of sorbed vanillic acid was displaced into the soil solution in the presence of ferulic acid. Hydroxybenzoic acid did not affect the sorption affinity of other phenolic acids significantly, whereas ferulic acid showed low displacement by other phenolic acids. The displacement pattern indicated directional sorption of phenolic acids with -OH and -COOH groups. Soil organic matter was associated with preferential sorption. This is the first study to elucidate competitive sorption characteristics of plant secondary metabolites in soil matrix. The results demonstrate that preferential sorption to soil can alter the availability of plant exudates in mixtures and thus may mediate their phytotoxic effects.  相似文献   

15.
Analysis of soil lipids may contribute to an improved understanding of atmosphere to soil carbon fluxes, soil organic matter source differentiation and pollutant accumulation. Soil lipids, mostly originating from plants and microorganisms, have traditionally been analysed by non‐automated extraction and separation methods, which produce several lipid fractions, operationally defined by polarity. Here we present a combination of fast, automated and reproducible techniques, adopted from organic geochemical studies, for preparative separation of individual soil lipid fractions with increasing polarity. These techniques involve commercially available instruments, including accelerated solvent extraction and a two‐step automated medium‐pressure liquid chromatography procedure. The method yields eight lipid fractions consisting of five fractions fully amenable to gas chromatography/mass spectrometry (GC/MS) (aliphatic hydrocarbons, aromatic hydrocarbons, ketones, alcohols, carboxylic acids), and three fractions of highly polar or high molecular weight compounds (bases, very long‐chain wax esters (C40+), high polarity compounds) that were not measurable with GC/MS under standard conditions. We tested the method on five agricultural soils. Results show that (i) mass recoveries for the individual fractions are reproducible, (ii) within individual fractions compound distribution patterns are reproducible, as demonstrated for alkanes and carboxylic acids, and (iii) individual fractions represent distinct and clean compound classes, free of interfering substances detectable by GC/MS. Thus, automated separation can be a fast, effective and reproducible procedure for fractionation of complex mixtures of soil lipids into clean compound classes, directly suitable for a variety of molecular (e.g. GC/MS) and isotopic characterizations (e.g. gas chromatography coupled with isotope ratio monitoring mass spectrometry or accelerator mass spectrometry).  相似文献   

16.
Phenolic acid profiles in some small berries   总被引:1,自引:0,他引:1  
The composition of phenolic acids in several small berries grown in Northeastern Poland, namely, low-bush blueberries, black mulberries, European juneberries, black currants, fruits of blue-berried honeysuckle, and blackberries, was determined by gas chromatography (GC) and mass spectrometry (MS). The total content of phenolic acids, identified by GC-MS, ranged from 2845.8 +/- 141.0 (black mulberries) to 5418.2 +/- 228.0 (blue-berried honeysuckle). Twenty phenolic acids were identified in the berries. Of these, hydroxycaffeic, m- and p-coumaric, and 3,4-dimethoxycinnamic acids were the major phenolic acids in blackberries and blueberries, m-coumaric acid was the major phenolic acid in blue-berried honeysuckle and black currant fruits, while salicylic, caffeic, and m- and p-coumaric acids were the predominant phenolic acids in European juneberries. Syringic and veratric acids were detected only in blueberries, while p-hydroxybenzoic and sinapic acids were present only in black currants and o-coumaric acid was present in blueberries and black mulberries. The phenolic acids liberated from esters and glycosidic bonds were the major fractions of phenolic acids in the berries.  相似文献   

17.
Leaf extracts from globe artichoke ( Cynara cardunculus L. var. scolymus) have been widely used in medicine as hepatoprotectant and choleretic agents. Globe artichoke leaves represent a natural source of phenolic acids with dicaffeoylquinic acids, such as cynarin (1,3-dicaffeoylquinic acid), along with its biosynthetic precursor chlorogenic acid (5-caffeoylquinic acid) as the most abundant molecules. This paper reports the development of an experimental system to induce caffeoylquinic acids. This system may serve to study the regulation of the biosynthesis of (poly)phenolic compounds in globe artichoke and the genetic basis of this metabolic regulation. By means of HPLC-PDA and accurate mass LC-QTOF MS and MS/MS analyses, the major phenolic compounds in globe artichoke leaves were identified: four isomers of dicaffeoylquinic acid, three isomers of caffeoylquinic acid, and the flavone luteolin 7-glucoside. Next, plant material was identified in which the concentration of phenolic compounds was comparable in the absence of particular treatments, with the aim to use this material to test the effect of stress application on the regulation of biosynthesis of caffeoylquinic acids. Using this material, the effect of UV-C, methyl jasmonate, and salicylic acid treatments on (poly)phenolic compounds was tested in different globe artichoke genotypes. UV-C exposure consistently increased the levels of dicaffeoylquinic acids in all genotypes, whereas the effect on compounds from the same biosynthetic pathway, for example, chlorogenic acid and luteolin-7-glucoside, was much less pronounced and was not statistically significant. No effect of methyl jasmonate or salicylic acid was found. Time-response experiments indicated that the level of dicaffeoylquinic acids reached a maximum at 24 h after UV radiation. On the basis of these results a role of dicaffeoylquinic acids in UV protection in globe artichoke is hypothesized.  相似文献   

18.
The pungent compounds piperine and isomers thereof, secondary metabolites present in black and white pepper fruit, undergo light-induced isomerizations. To facilitate studies in this area, an HPLC method has been developed for analysis and isolation of the following four possible piperine-derived photoinduced isomers: piperine, isopiperine, chavicine, and isochavicine. The limits of detection (LOD) estimated from calibration plots were approximately 15-30 ng for each isomer. Reproducibilities of the analyses were excellent, and recoveries of spiked samples were as follows (average +/- SD; n = 3): chavicine, 98.4 +/- 2.1%; isopiperine, 96.2 +/- 3.2%; piperine, 104 +/- 3.8%; isochavicine, 98.9 +/- 3.0%. To determine the kinetics of these isomerizations, fluorescent light, sunlight, and UV radiation at 254 nm was used to induce cis-trans geometric isomerization as a function of light intensities and time of exposure determined with the aid of high-performance liquid chromatography (HPLC) and liquid chromatography with diode array UV detection-mass spectrometry (LC-DAD/MS). HPLC was also used to determine the distribution of the isomers in four commercial ground black pepper products used as spices in culinary practice. Isomerization increased with light intensities and time of exposure and leveled off at the so-called photostationary phases. The piperine levels of the four products were quite similar, ranging (in wt %) from 10.17 to 11.68. The amounts of the other three isomers ranged from 0.01 to 0.07 of the total for chavicine; from 0.15 to 0.23 for isopiperine; and from 0.37 to 0.42 for isochavicine. The results establish the utility of the HPLC method for simultaneous analysis of the four isomers both in pure form and in black pepper extracts. The dietary significance of the results is discussed.  相似文献   

19.
The major constituents in grape seed and pine bark extracts are proanthocyanidins. To evaluate material available to consumers, select lots were analyzed using high-performance liquid chromatography, gas chromatography/mass spectrometry (GC/MS), liquid chromatography/mass spectrometry (LC/MS), gel permeation chromatography (GPC), and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). Atmospheric pressure chemical ionization (APCI) LC/MS was used to identify monomers, dimers, and trimers present. GC/MS analyses led to the identification of ethyl esters of hexadecanoic acid, linoleic acid, and oleic acid, as well as smaller phenolic and terpene components. The GPC molecular weight (MW) distribution indicated components ranging from approximately 162 to approximately 5500 MW (pine bark less than 1180 MW and grape seed approximately 1180 to approximately 5000 MW). MALDI-TOF MS analyses showed that pine bark did not contain oligomers with odd numbers of gallate units and grape seed contained oligomers with both odd and even numbers of gallate. Reflectron MALDI-TOF MS identified oligomers up to a pentamer and heptamer, and linear MALDI-TOF MS showed a mass range nearly double that of reflectron analyses.  相似文献   

20.
A method for the analysis of phenolic acids in plant and soil materials by high-performance liquid chromatography (HPLC) is described. Separation is by reversed-phase chromatography, based on differential polarity of the investigated compounds. Optimal separation conditions are achieved by using a concave gradient elution. The HPLC technique offers excellent resolution, reproducibility and an analysis time of 30 Min.  相似文献   

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