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1.
Equimolar aqueous solutions of d-glucose and glycine were heated at 50°C and 95°C at pH 6.7. The headspace volatiles and the ether extracts from the reaction mixture were analyzed by gas chromatography and gas chromatography-mass spectrometry, using a fused silica capillary column. The major components formed were identified as diacetyl, furfuryl alcohol, two pyrroles, one pyranone and two amides. In order to elucidate the formation mechanisms of the amides formed from amino-carbonyl reactions, two model systems were adopted. N-Butylacetamide and N-butylformamide were formed as major components from diacetyl-butylamine and glyoxalbutylamine systems, respectively. The results obtained suggest that such α-dicarbonyls as 3-deoxyosone, 1-deoxy-d-erythro-2,3-hexodiulose and diacetyl generated in the amino-carbonyl reaction react with amino compounds, amides then being formed by cleavage of the C-C bond in the a-dicarbonyls.  相似文献   

2.
The pyrolyzate of the nondialyzable melanoidin prepared from glucose-ammonia reaction system (kept in pH 5.3~6.0 during the reaction) was fractionated to volatile fraction and nonvolatile fraction. Among the volatile components, two pyridines and four alkylpyrazines were identified. On the other hand, one imidazole compound and two β-hydroxypyridines isolated from the nonvolatile fraction were identified as 4(5)-methylimidazole, 3-hydroxypyridine and 2-methyl-5-hydroxypyridine, respectively. It is inferred that these compounds are not produced by the fission of the main skeleton in the melanoidin molecule, but formed by pyrolysis of the heterocyclic compounds present as a small moiety in the melanoidin.  相似文献   

3.
Three angiotensin II receptor antagonists—losartan, candesartan, and zolarsartan—were investigated. All the compounds, which are structural analogues, are metabolized via conjugation to glucuronic acid. Interestingly, both O- and N-glucuronidation take place, so that regioisomers are formed. One ether O-glucuronide, two acyl O-glucuronides, and five tetrazole-N-glucuronides were biosynthesized, in milligram scale, from the three sartan aglycones. Liver microsomes from bovine, moose, rat, and pig and recombinant human UDP-glucuronosyltransferases were used as catalysts. The synthesized compounds were identified as sartan glucuronides by mass spectrometry, while the sites of glucuronidation were determined by nuclear magnetic resonance spectroscopy. Drug metabolites are needed as standards for pharmaceutical research and, as the present study shows, they can easily be produced with enzymes as catalyst.  相似文献   

4.
The effects of pH on the growth of Mycobacterium vanbaalenii PYR-1 and its degradation of phenanthrene and pyrene were compared at pH 6.5 and pH 7.5. Various degradation pathways were proposed in this study, based on the identification of metabolites from mass and NMR spectral analyses. In tryptic soy broth, M. vanbaalenii PYR-1 grew more rapidly at pH 7.5 (=0.058 h–1) than at pH 6.5 (=0.028 h–1). However, resting cells suspended in phosphate buffers with the same pH values displayed a shorter lag time for the degradation of phenanthrene and pyrene at pH 6.5 (6 h) than at pH 7.5 (48 h). The one-unit pH drop increased the degradation rates four-fold. Higher levels of both compounds were detected in the cytosol fractions obtained at pH 6.5. An acidic pH seemed to render the mycobacterial cells more permeable to hydrophobic substrates. The major pathways for the metabolism of phenanthrene and pyrene were initiated by oxidation at the K-regions. Phenanthrene-9,10- and pyrene-4,5-dihydrodiols were metabolized via transient catechols to the ring fission products, 2,2-diphenic acid and 4,5-dicarboxyphenanthrene, respectively. The metabolic pathways converged to form phthalic acid. At pH 6.5, M. vanbaalenii PYR-1 produced higher levels of the O-methylated derivatives of non-K-region phenanthrene- and pyrene-diols. Other non-K-region products, such as cis-4-(1-hydroxynaphth-2-yl)-2-oxobut-3-enoic acid, 1,2-dicarboxynaphthalene and benzocoumarin-like compounds, were also detected in the culture fluids. The non-K-region polycyclic aromatic hydrocarbon oxidation might be a significant burden to the cell due to the accumulation of toxic metabolites.  相似文献   

5.
Summary Soils which are flooded for lowland rice culture shift from aerobic to anaerobic organic matter transformations. Anaerobic carbon transformations, involving chiefly rice crop residues, are characterized by the formation of various organic acids. These may accumulate after prolonged incubations in amounts sufficient to be toxic to developing rice seedlings. In these experiments the effects of acetic, propionic, and butyric acids were studied at 1, 5, and 10 mN on the growth and nutrition of 14 day old (Oryza sativa L.) cultivar Earlirose rice seedlings. Nutrient solutions were used in the experiments with pH controlled at 6.5 in one experiment and in another the acid concentrations were allowed to attain equilibrium pH with the nutrient solution (1 mN=4.6, 5 mN=3.9, and 10 mN=3.8).Root elongation of rice seedlings was decreased by increased organic acid concentrations at both pH's. New root initiation was totally inhibited at all organic acid concentrations at equilibrium pH, and at 10 mN with pH 6.5. New root initiation at 1 and 5 mN at pH 6.5 allowed increased seedling dry matter production, whereas it was reduced in all other treatments. Plant height and weight were also decreased by increased acid concentrations. At pH 6.5 the plants showed no specific symptoms of organic acid toxicity except reduced growth. At equilibrium pH values specific symptoms were observed. At 1 mN, the seedlings withered, similar to desiccation; at 5 mN the leaf tips showed symptoms similar to bronzing; and at 10 mN the seedlings died after 24 hours.Uptake of both P and K by roots were reduced by increased concentrations of all organic acids at both pH's. P concentration and total uptake were reduced in the shoots with all treatments, whereas the effects on K in shoots were not consistent.The magnitude of organic acid toxicity is a function of the kind, concentration and the degree of dissociation of the acid. Increased media pH reduces the toxicity of the acid concentrations.Contribution from the Department of Agronomy and Range Science, University of California, Davis, California 95616.Contribution from the Department of Agronomy and Range Science, University of California, Davis, California 95616.  相似文献   

6.
A comprehensive inventory of the organic components and aroma-active compounds produced by Antrodia camphorata during growth in submerged culture has been established by extracting culture fluids using three different organic solvent systems and subjecting the extracts to gas chromatography-mass spectrometry (GC–MS) and gas chromatography–olfactometry (GC-O). Forty-two organic components, of which esters, alcohols, acids and ketones were the most prevalent, were identified in pentane/ether (1/1, v/v) extracts. The most representative of A. camphorata aroma-active compounds were detected in pentane/ether and ether extracts (eleven and nine aroma-active compounds, respectively) by GC-O. Of these, ethyl acetate, γ-undecalactone, linaloöl and 3-hydroxy-2-butanone were assessed to be present at the highest intensity.  相似文献   

7.
Zusammenfassung Die Bildung von flüchtigen Gärungsnebenprodukten durch Milchsäurebakterien wurde gaschromatographisch durch Analyse des Dampfraumes über den Kulturlösungen und Analyse von Ätherextrakten untersucht. Da von den meisten Substanzen nur sehr geringe Mengen gebildet werden, war es wegen des Vorkommens störender Substanzen in den Medien erforderlich, zur Kultur der Organismen synthetische Nährlösungen zu verwenden. In den Kulturlösungen der 3 homofermentativen Milchsäurebakterien Lactobacillus plantarum, Pediococcus cerevisiae und P. pentosaceus wurden nur Acetaldehyd, Acetoin, Diacetyl, sowie Spuren von 2- oder 3-Methyl-1-butanol, Isobutanol und 2 nicht identifizierte Substanzen gefunden. Bei den heterofermentativen Arten Lactobacillus brevis und Leuconostoc oenos wurde (neben Äthanol) zusätzlich die Bildung von sehr geringen Mengen von Propanol, i-Propanol, Essigsäureäthylester, n-Hexanol, 2,3-Butandiol, n-Octanol, n-Nonanol (oder Phenylacetaldehyd) und einiger weiterer Verbindungen nachgewiesen.
On the formation of volatile by-products of fermentation by lactic acid bacteria
Summary The formation of volatile by-products of fermentation by several strains of lactic acid bacteria was investigated by gas liquid chromatography. Since only very small amounts of volatile compounds were formed, the synthetic media used for the growth of the bacteria had to be stripped by vacuum distillation from substances interfering with the analysis. The culture solutions were analysed by gas chromatography using both the head-space-technique and extraction with ethyl ether. The homofermentative species Lactobacillus plantarum, Pediococcus pentosaceus, and P. cerevisiae were found to form small amounts of acetaldehyde, acetoin, diacetyl and traces of 2- or 3-methyl-1-butanol, isobutanol and two compounds that were not identified. In the culture solutions of the heterofermentative species L. brevis and Leuconostoc oenos a greater number of substances could be detected. These bacteria formed, besides ethanol and the products of the homofermentative organisms, small amounts of propanol, isopropanol, ethylacetate, n-hexanol, 2,3-butandiol, n-octanol and a few unidentified compounds.
  相似文献   

8.
《Free radical research》2013,47(8):643-650
Abstract

Heating glucose with lysine under alkaline conditions (pH 7.0–10.0) was found to take place with consumption of oxygen together with formation of brown-colored compounds. Highly reactive intermediary radicals were detected when lysine and glucose were heated at intermediate water activity at pH 7.0 and 8.0. The detection was based on initial trapping of highly reactive radicals by ethanol followed by spin trapping of 1-hydroxyethylradicals with α-(4-pyridyl N-oxide)-N-tert-butylnitrone (POBN) and Electron Spin Resonance (ESR) spectroscopy. The generation of reactive intermediary radicals from the Maillard reactions was favored by enhancing alkaline conditions (pH 8.0) and stimulated by presence of the transition metal ion Fe2+. The stability of the nitrone spin traps, N-tert-butyl-α-phenylnitrone and POBN was examined in buffered aqueous solutions within the pH range 1–12, and found to be less temperature dependent at acidic pH compared to alkaline conditions. A low rate (kobs) of hydrolysis of POBN was found at the used experimental conditions of 70°C and pH 7.0 and 8.0, which made this spin trap method suitable for the detection of radicals in the Maillard reaction system.  相似文献   

9.
李群  谭韵雅  王平  魏琴  钱双  石丹 《广西植物》2014,(4):520-524
为进一步明确大叶桉的化学成分,对大叶桉叶水浸提液分别用不同极性的有机溶剂石油醚、乙酸乙酯和正丁醇进行萃取,对各萃取相进行GC-MS分析。结果表明:大叶桉叶水浸提液共含有37种化合物,其中,石油醚萃取相中含有20种,主成分为草酸丁基异己酯(37.24%);乙酸乙酯萃取相中含有16种,主成分为2,2-二亚甲基双[6-(1,1-二甲基乙基-4-甲基)]-苯酚(50.05%);正丁醇萃取相中含有5种,主成分为丙基-2-甲基丁酸酯(54.57%)。在所有成分中,酯类物质居多,也有少量的烯、酮、醇、苯和烷烃。1-甲基,4-(1-甲基乙基)-1,4环己二烯、2,2-二亚甲基[6-(1,1-二甲基乙基)-4-甲基]苯酚、1-十八烯和二十烷为石油醚和乙酸乙酯的共有成分;1、2-苯二甲酸单(2-乙基己基)酯为乙酸乙酯和正丁醇的共有成分。该研究进一步明确了大叶桉的化学成分,为其在医药、化工和化感方面的应用研究奠定了基础。  相似文献   

10.
Volicitin-related compounds were found in the oral secretion of the three noctuid species, Helicoverpa armigera, Mythimna separata and Spodoptera litura, and one sphingid species, Agrius convolvuli. Volicitin [N-(17-hydroxylinolenoyl)-L-glutamine], N-(17-hydroxy-linoleoyl)-glutamine, N-linolenoylglutamine and N-linoleoylglutamine were identified in the secretion from the noctuid larvae. In secretions from the sphingid larvae, N-linolenoylglutamine and N-linoleoylglutamine were the main components. Furthermore, there were significant differences in the amounts of the N-acylamino acid conjugates in the secretions from the three noctuid species. These results suggest that the proportion of volicitin-related compounds in the regurgitant was species-specific.  相似文献   

11.
The aqueous extract of dried bonito (Katsuobushi) was distilled under reduced pressure. The resulting distillate with diethyl ether and the extract was separated into acidic, phenolic, basic and neutral fractions. The neutral fraction was further fractionated into ten sub-fractions by silica gel column chromatography. All these sub-fractions were analyzed by gas chromatography and gas chromatography-mass spectrometry.

One hundred and sixty-five compounds were identified and 12 compounds were tentatively identified from the neutral fraction. Among them, 111 compounds were newly identified as flavor components of Katsuobushi.  相似文献   

12.
Microorganisms associated with invertebrate hosts have long been suggested to be a source for bioactive metabolites. In this study, we reported that a sponge-associated fungus, Letendraea helminthicola, produced two antifouling compounds: 3-methyl-N-(2-phenylethyl) butanamide and cyclo(D-Pro-D-Phe). To optimize the production of these antifouling compounds, we then examined the production of compounds under different culture conditions (temperature, salinity, pH, and carbon and nitrogen sources). This fungus grew well and produced more compounds at temperatures between 18 and 30°C; the fungus grew well at 75 parts per thousand (ppt) salinity but produced the highest amount of antifouling compounds at 30 and 45 ppt. The optimal initial pH value for mycelial growth was 5.5 to 6.5, whereas the production of the antifouling compounds was maximized at pH 3.5 and 4.5. Glucose and xylose (as carbon sources) increased the production of antifouling compounds. Yeast extract and peptone (as nitrogen sources) maximized the production of mycelial biomass and antifouling compounds. Our results indicate that culture conditions greatly affect the production of bioactive compounds from mycelial fungal cultures as exemplified by strain L. helminthicola and that the conditions favorable for fungal growth may not be the best conditions for bioactive compound production.  相似文献   

13.
Incorporation of N-succinimidyl-3(4-hydroxyphenyl) propionate (Bolton-Hunter reagent) or its 125I-labeled derivative into peptides can be selectively directed towards either α- or ε-amine functions by modifying the pH of the reaction. Acylation of α-amino groups is favored at pH 6.5 whereas ε-amino groups react more readily at pH 8.5. We have taken advantage of this result to prepare two new 125I-labeled analogues of substance P and neurotensin that bind selectively and reversibly to their respective receptors. The method described here is of general interest and can be used to incorporate various reporter groups into peptide structures.  相似文献   

14.
Transformation of N′,N′-dimethyl-N-(hydroxyphenyl)ureas was assayed in the presence of purified laccase produced by the fungus Trametes versicolor. The para- and ortho-hydroxyphenyl derivatives were enzymatically transformed, whereas the meta derivative was not. The performance of laccase-mediated transformation depended on the pH, with an optimum for the para-derivative degradation rate at pH 5. The pH also influenced the nature of the reaction products. The chemical was exclusively oxidised into p-benzoquinone at pH 3 and into mainly N′,N′-dimethyl-N-[(2,5-cyclohexadiene-1-one)-4-ylidene]urea at pH 6. The ortho- derivative was transformed essentially into insoluble purple compounds, probably appearing as polymers resulting from coupling of the parent compound. Received: 14 September 1998 / Received revision: 23 November 1998 / Accepted: 29 November 1998  相似文献   

15.
The nondialyzable melanoidins prepared from glucose-butylamine (I) and xylose–butylamine (II) reaction systems, freeze-dried powder obtained from the dialyzable fraction of the glucose–butylamine reaction system (III) and N-butyl-glucosylamine (IV) were pyrolyzed at 350°C for 0.5-2 hr and the volatile pyrolysate was investigated. To trap the volatile compounds, Tenax GC trapping and cold trapping methods were used. Identification of these volatiles was made by gas chromatography-mass spectrometry, using a glass capillary column. The volatile components in the pyrolysates of I, II, III and IV were qualitatively similar to each other. The major volatile components in the pyrolysates of I, II, III and IV were identified as two furans, 1-butanol, two 1-butylpyrroles, 1-butylpyrrolidine, 1-butylaziridine and two N-butylamides. The results are discussed in relation to those obtained from previously investigated sugar-amino acid melanoidins.  相似文献   

16.
Methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside was treated with 2,3,4-tri-O-benzyl-6-O-(N-phenylcarbamoyl)-1-O-tosyl-D-glucopyranose in diethyl ether to give methyl 2,3,4,2',3',4'-hexa-O-benzyl-6'-O-(N-phenylcarbamoyl)-α-isomaltoside. The disaccharide was decarbanilated in ethanol with sodium ethoxide to give methyl 2,3,4,2',3',4'-hexa-O-benzyl-α-isomaltoside. The sequence of coupling with the same 1-O-tosyl-D-glucose derivative followed by removal of the N-phenylcarbamate group was repeated until the hexasaccharide derivative, methyl octadeca-O-benzyl-α-isomaltohexaoside, was formed. Methyl α-isomaltopentaoside was prepared by debenzylation of the corresponding benzylated oligosaccharide. The structures of the oligosaccharides were determined with the aid of both 1H- and 13C-n.m.r. spectroscopy. From spectral data, we estimate the coupling reaction to be 95% stereoselective.  相似文献   

17.
Glyoxylic acid, added to aqueous suspensions of chitosan, causes immediate dissolution of chitosan and gel formation within 3–4 h if the pH is 4.5–5.5. Solutions at lower pH values gel after 2 min of warming at 60–80°. Chitosan glyoxylate solutions brought to alkaline pH with sodium hydroxide do not precipitate chitosan. Evidence is given that a Schiff base, namely N-(carboxymethylidene)chitosan, is formed. N-(Carboxymethylidene)chitosans are reduced by sodium cyanoborohydride at room temperature to give N-(carboxymethyl)chitosans, obtained as white, free-flowing powders, soluble in water at all pH values. A series of N-(carboxymethyl)chitosans having various degrees of acetylation and N-carboxymethylation was obtained, and characterized by viscometry, elemental analysis, and i.r. spectrometry. For the fully substituted N-(carboxymethyl)chitosans, the pK′ is 2.3, the pK″ is 6.6, and the isoelectric point is 4.1. The addition of N-(carboxymethyl)chitosan to solutions (0.2–0.5mm) of transition-metal ions produces immediate insolubilization of N-(carboxymethyl)chitosan-metal ion chelates.  相似文献   

18.
Bacterial strains growing in medium with mustard gas reaction masses (RM) as the carbon source were obtained. Growth cessation in the above medium was caused by the exhaustion of bioutilizable substrates, first of all monoethanolamine (MEA) and ethyleneglycol (EG), rather than by the accumulation of toxic metabolites in the culture liquid or in the cells. The main RM components, 1,4-perhydrothiazines (PHT), formed in the course of chemical detoxication of mustard gas, were identified and analyzed. The predominant component of the PHT mixture was N-(2-hydroxyethyl)-2-methyl-1,4-perhydrothiazine hydrochloride. Concentrations of all the PHT decreased by 50% in the course of culture growth; their destruction was a result of microbial metabolism.  相似文献   

19.
A series of novel and selective N-[3-(6-benzyloxy-3-methoxyphenyl)propyl] amides has recently been shown to possess sub-nanomolar range binding affinity to the type 2 melatonin receptor (MT2). Pharmacokinetics studies suggested that these compounds were subject to vigorous CYP450-mediated metabolism, resulting in a series of metabolites with significantly decreased or diminished binding affinities toward MT2 receptor. The ether bonds were found to be the major positions susceptible to metabolism. In this study, the benzyl ether bond was either removed or replaced with a carbon–carbon bond in an attempt to improve metabolic stability and enhance their resistance towards phase I oxidation. The synthesis, receptor binding affinity, intrinsic potency and metabolic stability of modified structures are reported in this article. By removal or replacement of metabolic labile ether linkerage with carbon linkers, a novel compound was identified with good potency and MT2 selectivity, and with increased metabolic stability.  相似文献   

20.
Enzymatic hydrolysis with β‐glucuronidase/sulfatase was used for the enantioselective determination of N‐hydroxymexiletine glucuronide in plasma for pharmacokinetic studies. N‐Hydroxymexiletine glucuronide was determined as the quantity of mexiletine released by hydrolysis (difference between the enantiomeric concentrations of mexiletine obtained with and without hydrolysis). Plasma samples (100 μl) were treated at pH 5.0 with 10 mg of the enzyme (Limpet Acetone Powder type I) for 16 hr at 37°C and extracted at pH 10.4 with diisopropyl ether. Chiral mexiletine discrimination was obtained by reaction with o‐phthalaldehyde/N‐acetyl‐L ‐cysteine, separation of the resulting diastereomers on a C‐18 reversed‐phase column with a mobile phase of methanol–0.05 N acetate buffer, pH 5.5 (6.5:3.5, v/v), and fluorescence detection (λex 350 nm, λem 455 nm). The performance characteristics for the enantioselective analysis of mexiletine preceded by enzymatic hydrolysis were recovery ∼90%, quantification limit 1 ng/ml, and linearity up to 1000 ng/ml plasma for both enantiomers. The coefficients of variation obtained in the study of intra‐ and inter‐day precision were respectively 5% and 7% for both enantiomers. The assay was shown to be suitable for a pharmacokinetic study performed in a patient with the arrhythmic form of chronic Chagas' heart disease treated with 200 mg t.i.d. of racemic mexiletine hydrochloride. The high sensitivity of the method allows analysis of only 100 μl plasma. Chirality 11:85–90, 1999. © 1999 Wiley‐Liss, Inc.  相似文献   

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