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  • 1
    Electronic Resource
    Electronic Resource
    Oxford, UK : Munksgaard International Publishers
    Physiologia plantarum 119 (2003), S. 0 
    ISSN: 1399-3054
    Source: Blackwell Publishing Journal Backfiles 1879-2005
    Topics: Biology
    Notes: Plants and mammals contain polyunsaturated fatty acids (PUFAs) in their membranes. PUFAs belong to the most oxygen sensitive molecules encountered in nature. It would seem that nature has selected this property of PUFAs for signalling purposes: PUFAs are stored in the surface of cells and organelles not in free form but conjugated to phospho- and galactolipids. Any change in membrane structure apparently activates membrane-bound phospholipases, which cleave the conjugates. The obtained free PUFAs are substrates for lipoxygenases (LOX). These transform PUFAs to lipidhydroperoxides (LOOHs). LOOHs are converted to a great variety of secondary products. These lipid-peroxidation (LPO) products and the resulting generated products thereof represent biological signals, which do not require a preceding activation of genes. They are produced as a non-specific response to a large variety of external or internal impacts, which therefore do not need interaction with specific receptors. When, due to an external impact, e.g. attack of a microorganism, or to a change in temperature, the amount of liberated free PUFAs exceeds a certain threshold, LOX commit suicide. Thus iron ions, located in the active centre of LOX, are liberated. Iron ions react with LOOHs in the close surroundings by generating alkoxy radicals (LO.). These induce a non-enzymatic LPO. A fraction of the LO. radicals generated from linoleic acid (LPO products derived from linoleic acid play a dominant role in signalling which was previously overlooked) is converted to 2,4-dienals which induce the programmed cell death (PCD) and the hypersensitive reaction (HR). While peroxyl radicals (LOO.) generated as intermediates in the course of an enzymatic LPO are transformed within the enzyme complex to corresponding anions (LOO–), and thus lose their reactivity, peroxyl radicals generated in non-enzymatic reactions are not deactivated. They not only react by abstraction of hydrogen atoms from activated X-H bonds of molecules in their close vicinity, but also by epoxidation of double bonds and oxidation of a variety of biological molecules, causing a dramatic change in molecular structure which finally leads to cell death. As long as reducing agents, like glutathione, or compounds with free phenolic groups are available, the amount of LOOHs is kept low. Cell death is induced in a defined way by apoptosis. But when the reducing agents have been consumed, PCD seems to switch to necrotic processes. Thus proliferation is induced by minor changes at the cell membrane, while slow changes at cell membranes are linked with apoptosis (e.g. response to attack of microorganisms or drought) and necrosis (severe wounding), depending only on the amount, but not on the type, of applied stimulus.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Springer
    European food research and technology 187 (1988), S. 330-333 
    ISSN: 1438-2385
    Source: Springer Online Journal Archives 1860-2000
    Topics: Process Engineering, Biotechnology, Nutrition Technology
    Description / Table of Contents: Summary Unsaturated fatty acids are oxidized by lipoxygenase enzymes. The resulting products can easily be detected e.g., in strawberries, by comparing fruit homogenates obtained in water and in a chloroformmethanol mixture, since lipoxygenases are active only in aqueous solutions. A comparison can be made by applying gas chromatography to the methylated fatty acid fractions of the two homogenates. Moreover, the differences between ripe and unripe fruits can be detected using this method. 10-Hydroxy-octadeca-8,12-dienoic acid and 10-hydroxyoctadec-8-enoic acid were detected in large quantities in the aqueous homogenates. These compounds possess fungi-toxic activity and may be involved in the self-defence mechanism of the plant. Additionally, 8-(2-furyl)octanoic acid is detectable in aqueous homogenates. This compound has previously been shown to arise from the thermal decomposition of 9-hydroperoxy-10,12-epidioxyoctadecanoic acid.
    Notes: Zusammenfassung Ungesättigte Fettsäuren werden von Lipoxygenasen oxidiert und teilweise gespalten. Die entstehenden Reaktionsprodukte sind leicht erkennbar, wenn man — wie hier am Beispiel der Erdbeeren gezeigt — die Früchte einmal in wäßriger Lösung, ein zweites Mal in einer Methanol-Chloroformmischung homogenisiert. Da die Lipoxygenasen nur im wäßrigen Medium funktionstüchtig sind, erhält man nur in diesem Falle Oxidationsprodukte. Diese sind nach Umsatz mit Diazomethan durch Vergleich der Gaschromatogramme der Säurefraktionen der in wäßriger und organischer Lösung aufgearbeiteten Proben erkennbar. Zusätzlich kann man auf diese Weise vergleichen wie sich unreife von reifen Früchten unterscheiden. Im wäßrigen Homogenisat wurden auf diese Weise 10-Hydroxy-8-octadecensäure und 10-Hydroxy-8,12-octadecadiensäure nachgewiesen, die bekanntlich fungitoxische Wirkung haben und am Selbstabwehrsystem der Pflanze beteiligt sein könnten. Im wäßrigen Homogenisat wurde zusätzlich 8-(2-furyl)octansäure gefunden, eine Verbindung, von der man kürzlich nachwies, daß sie bei der thermischen Zersetzung von 9-hydroperoxy-10,12-epidioxyoctadecansäure entsteht.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 107 (1976), S. 459-472 
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The syntheses and mass spectra of the four 3,17β-dihydroxyandrostane-11,16-diones and of the two 17β-hydroxyandrostane-3,11,16-triones are described. These compounds decompose in the mass spectrometer in a different way than androstanes containing a carbonyl group in the position 11 or 16: First they eliminate the C-atoms 15 to 17. Then a cleavage of the C-atoms of the ringA plus C-6 follows resulting in key ions which contain the ringC and the C-atom 7. The connection of theA/B-ring system can be deduced by the spectra for all described compounds. The unequivocal determination of the configuration of the 3-hydroxy group is possible only for the 3,17β-dihydroxy-5β-androstan-11,16-diones.
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Springer
    Archives of toxicology 29 (1972), S. 153-157 
    ISSN: 1432-0738
    Keywords: AN 1 ; Amphetamine ; Doping Controls ; AN 1 ; Amphetamin ; Dopingkontrollen
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Description / Table of Contents: Zusammenfassung Nach Einnahme von AN 1 (1) (α-Phenyl-α-N-(1-phenyl-isopropyl)-amino-acetonitril) konnte im Urin von Versuchspersonen mit Hilfe der Kombination GC-MS Amphetamin (2) nachgewiesen werden. Da dieses Psychotonikum frei im Handel erhältlich ist, sollte dieser Befund in Zukunft bei der Durchführung von Dopingkontrollen berücksichtigt werden.
    Notes: Abstract After oral administration of the psychotonic AN 1 (1) (α-Phenyl-α-N-(1-phenylisopropyl)-amino-acetonitril), amphetamine (2) could be detected in the urine of volunteers by GC-MS-analysis. Since this drug is commercially free available this finding should be considered in doping controls in the future.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Springer
    Naturwissenschaften 82 (1995), S. 452-460 
    ISSN: 1432-1904
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology , Natural Sciences in General
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Springer
    Naturwissenschaften 82 (1995), S. 452-460 
    ISSN: 1432-1904
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology , Natural Sciences in General
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 111 (1980), S. 249-258 
    ISSN: 1434-4475
    Keywords: Amino acid conjugates ; Conjugates of amino acids ; Metabolic profiling
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The conjugates of glycine with furan 2,5-dicarboxylic acid and of picolinic acid as well as a conjugate of pyroglutamic acid with phenylacetic acid, previously unknown as natural metabolites, were detected to be normal metabolites in human urine.
    Type of Medium: Electronic Resource
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  • 8
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract The combination of a gaschromatograph with a high resolution mass spectrometer may provide in the investigation of steroids, isolated from natural sources, fast information about otherwise barely detectable minor steroid metabolites. The limit of detection is about 1 γ. Free steroids show more structure specific spectra than their corresponding trimethylsilyl derivatives. Therefore the preparation of trimethylsilyl derivatives for the purpose of gaschromatographic separation should be avoided if possible. If low volatility necessitates the preparation of a derivative, in most cases the preparation of keto derivatives from hydroxysteroids should be preferred to the preparation of trimethylsilyl ethers. Reactions can be carried out with the mixture, so that-without preparation of pure samples-at least partial structure determinations are possible with 10–20 γ.
    Notes: Zusammenfassung Die Kombination eines Gaschromatographen mit einem hochauflösenden Massenspektrometer kann bei der Untersuchung von Steroidgemischen, die aus biologischen Materialien isoliert wurden, rasche Information über sonst kaum nachweisbare Steroidmetaboliten liefern. Die Erfassungsgrenze liegt bei etwa1 γ. Freie Steroide zeigen strukturspezifischere Spektren als ihre Trimethylsilylderivate, so daß, wenn immer möglich, auf eine Silylierung zur gaschromatographischen Trennung verzichtet werden sollte. Ist wegen der Schwerflüchtigkeit der Verbindung eine Derivatbildung notwendig, so ist die Umwandlung von Hydroxysteroiden in entsprechende Ketosteroide in den meisten Fällen einer Trimethylsilylierung vorzuziehen. Umsetzungen können im Gemisch ausgeführt werden, so daß zumindest eine teilweise Strukturaufkläurung ohne Reinisolielierung der Probe mit Mengen von 10 bis 20 γ möglich ist.
    Type of Medium: Electronic Resource
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  • 9
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 99 (1968), S. 1839-1850 
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract Secondary alcohols of higher molecular weight undergo stepwise fragmentation in the mass spectrometer. In a first step, parent molecular ions give rise toM-18 fragments and key fragments formed by α-cleavage, i.e. cleavage of carbon-carbon bonds α to the hydroxyl group. Nearly all other fragments arise from further cracking of α-cleavage products by elimination of water and C n H2n molecules producing C n H2n−1 + fragments. The course of this fragmentation was studied by means of deuterated compounds. α-cleavage products of tertiary alcohols, however, eliminate alcohol molecules in dependence on the alkyl chain length. This was corroborated by the detection of peaks of meta-stabile ions.
    Notes: Zusammenfassung Höher molekulare sekundäre Alkohole werden im Massenspektrometer stufenweise abgebaut. Als primäre Spaltprodukte entstehen aus den MolekülionenM-18-Fragmente und Schlüsselbruchstücke, die durch Bruch einer zur Hydroxylgruppe benachbarten C−C-Bindung gebildet werden (α-Spaltung). Nahezu alle übrigen Fragmente entstehen durch weiteren Zerfall der α-Spaltungsprodukte. Zunächst wird aus diesen Wasser eliminiert, danach C n H2n -Moleküle unter Bildung von C n H2n−1 +-Bruchstücken. Der Verlauf dieser Abbaureaktionen worde mit Hilfe von deuteriummarkierten Verbindungen studiert. Dagegen zeigen die α-Spaltungsprodukte tertiärer Alkohole vorwiegend die Eliminierung von Alkoholmolekülen in Abhängigkeit von der Kettenlänge der Alkylreste. Dies konnte durch das Auffinden von Banden metastabiler Ionen belegt werden.
    Type of Medium: Electronic Resource
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  • 10
    Electronic Resource
    Electronic Resource
    Springer
    International journal of legal medicine 70 (1972), S. 245-250 
    ISSN: 1437-1596
    Keywords: Appetitzügler, Metaboliten ; Benzphetamin ; Furfenorex ; Methamphetamin, Metabolit des Benzphetamins
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine , Law
    Description / Table of Contents: Zusammenfassung Die Appetitzügler Didrex (1) [1-Phenyl-2-(N, N′-methyl-benzyl-amino)propan — Benzphetamin] und Frugalan (2) [1-Phenyl-2-(N, N′-methyl-furfuryl-amino)propan = Furfenorex] werden — wie GC-MS-Analysen ergaben — beim Menschen zu Methamphetamin (3) (1-Phenyl-2-methylamino-propan) metabolisiert. Käufliche Muster beider Präparate enthielten neben anderen Verunreinigungen Spuren von Methamphetamin (3).
    Notes: Summary The anorectics Didrex (1) [1-Phenyl-2-(N, N′-methyl-benzyl-amino)propane = Benzphetamine] and Frugalan (2) [1-Phenyl-2-(N, N′-methyl-furfuryl-amino)propane = Furfenorex] are metabolized to methamphetamine (3) (1-Phenyl-2-methylamino-propane) in man as demonstrated by GC-MS-analysis. Commercially available samples of the two drugs contained — besides other impurities — traces of methamphetamine (3).
    Type of Medium: Electronic Resource
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