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  • 1
    Electronic Resource
    Electronic Resource
    Oxidative responses in soybean foliage to herbivory by bean leaf beetle and three-cornered alfalfa hopper (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 639-650 
    Details
    ISSN: 1573-1561
    Keywords: Soybean ; lipoxygenase ; peroxidase ; polyphenol oxidase ; trypsin inhibitor ; ascorbate oxidase ; oxidative stress ; Lepidoptera ; Noctuidae ; Helicoverpa zea ; corn earworm ; Cerotoma trifurcata ; bean leaf beetle ; Coleoptera ; Chrysomelidae ; Spissistilus festinus ; three-cornered alfalfa hopper ; Homoptera ; Membracidae ; induced resistance ; interspecific competition
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Variation in induced responses in soybean is shown to be dependent, in part, upon herbivore species. Herbivory by the phloem-feeding three-cornered alfalfa hopper caused increases in the activities of several oxidative enzymes including lipoxygenases, peroxidases, ascorbate oxidase, and polyphenol oxidase. Bean leaf beetle defoliation caused increased lipoxygenase activity, but had little effect upon peroxidase, polyphenol oxidase, ascorbate oxidase, or trypsin inhibitor levels in either field or greenhouse studies. In one field experiment, prior herbivory by the bean leaf beetle subsequently reduced the suitability of foliage to the corn earwormHelicoverpa zea. The contribution of these findings to emerging theories of insect-plant interactions is discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02059604
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  • 2
    Electronic Resource
    Electronic Resource
    Induced resistance in soybean toHelicoverpa zea: Role of plant protein quality (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 183-198 
    Details
    ISSN: 1573-1561
    Keywords: Induced resistance ; protein quality ; Helicoverpa zea ; soybean ; Glycine max ; protease inhibitor ; lipoxygenase ; Lepidoptera ; noctuidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Resistance in soybean toHelicoverpa zea is comprised of both constitutive and inducible factors. In this study, we investigated the induction of resistance byH. zea in both greenhouse and field studies. In a greenhouse experiment, fourth-instarH. zea growth rates were reduced by 39% after 24 hr feeding and by 27% after 48 hr when larvae fed on previously wounded V3 foliage (cv. Forrest) compared with undamaged foliage. In a field study, the weight gain by larvae was more than 52% greater when larvae fed for 72 hr on undamaged R2/R3 soybean plants (cv. Braxton) compared to those that fed on previously wounded plants. A significant component of the induced resistance is due to a decline in the nutritional quality of foliar protein following foliar damage byH. zea. Foliar protein was extracted from damaged and undamaged foliage and incorporated into artificial diets. Larval growth was reduced 26% after four days and 49% after seven days on diets containing protein from damaged plants compared to larvae feeding on foliar protein from undamaged plants. Chemical analyses of protein quality also indicated a decline in quality in damaged plants compared to unwounded plants. Increases in lipoxygenase activity (53%), lipid peroxidation products (20%), and trypsin inhibitor content (34%) were observed in protein from wounded plants. Moreover, a 5.9% loss in free amines and 19% loss in total thiols occurred in protein from wounded plants. Larval feeding causes a significant increase in foliar lipoxygenase activity that varied among genotypes. Lipoxygenase isozymes were measured at pH 5.5, pH 7.0, and pH 8.5 in V3 stage plants of Forrest, Hark, D75-1069, and PI 417061 genotypes. Lipoxygenase activity in each genotype was significantly increased after 72 hr of larval feeding at each pH level tested, with the exception of lipoxygenase isozymes at pH 5.5 in genotype PI 417061. Larval feeding on R2/R3 stage plants (field-grown cv. Braxton) for six days also increased foliar lipoxygenase activity.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02066000
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  • 3
    Electronic Resource
    Electronic Resource
    Potential role of lipoxygenases in defense against insect herbivory (1994)
    Springer
    Journal of chemical ecology 20 (1994), S. 651-666 
    Details
    ISSN: 1573-1561
    Keywords: Helicoverpa zea ; Lepidoptera ; Noctuidae ; lipoxygenase ; lipid peroxidation ; resistance ; herbivory ; soybean ; tomato ; cotton ; oxidative stress ; induced defense
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The potential role of the plant enzyme lipoxygenase in host resistance against the corn earwormHelicoverpa zea was examined. Lipoxygenase is present in most of the common host plants ofH. zea, with highest activity in the leguminous hosts such as soybean and redbean. Treatment of dietary proteins with linoleic acid and lipoxygenase significantly reduced the nutritive quality of soybean protein and soy foliar protein. Larval growth was reduced from 24 to 63% depending upon treatment. Feeding byH. zea on soybean plants caused damage-induced increases in foliar lipoxygenase and lipid peroxidation products. Larvae feeding on previously wounded plant tissue demonstrated decreased growth rates compared to larvae feeding on unwounded tissue. Midgut epithelium from larvae feeding on wounded tissues showed evidence of oxidative damage as indicated by significant increases in lipid peroxidation products and losses in free primary amines. The potential role of oxidative and nutritional stress as a plant defensive response to herbivory is discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02059605
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  • 4
    Electronic Resource
    Electronic Resource
    Avoidance of antinutritive plant defense: Role of midgut pH in Colorado potato beetle (1992)
    Springer
    Journal of chemical ecology 18 (1992), S. 571-583 
    Details
    ISSN: 1573-1561
    Keywords: Leptinotarsa decemlineata ; Coleoptera ; Chrysomelidae ; Colorado potato beetle ; Helicoverpa zea ; Lepidoptera ; Noctuidae ; phenolics ; poly-phenol oxidase ; peroxidase ; chlorogenic acid ; Lycopersicon esculentum ; tomato ; host-plant resistance ; midgut pH
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The fate of the tomato foliar phenolic, chlorogenic acid, in the digestive systems of Colorado potato beetleLeptinotarsa decemlineata (Coleoptera: Chrysomelidae) andHelicoverpa tea (Lepidoptera: Noctuidae) is compared. In larvalH. zea and other lepidopteran species previously examined, approximately 35–50% of the ingested chlorogenic acid was oxidized in the digestive system by foliar phenolic oxidases (i.e., polyphenol oxidase and peroxidase) from the tomato plant. The oxidized form of chlorogenic acid, chlorogenoquinone, is a potent alkylator of dietary protein and can exert a strong antinutritive effect upon larvae through chemical degradation of essential amino acids. In contrast, inL. decemlineata less than 4% of the ingested dose of chlorogenic acid was bound to protein. In vitro experiments to determine the influence of pH on covalent binding of chlorogenic acid to protein showed that 30–45% less chlorogenic acid bound to protein at pHs representative of the beetle midgut (pH 5.5–6.5) than at a pH representing the lepidopteran midgut (pH 8.5). At an acidic pH, considerably more of the alkylatable functional groups of amino acids (−NH2, −SH) are in the nonreactive, protonated state. Hence, polyphenol oxidases are unlikely to have significant antinutritive effects against the Colorado potato beetle and may not be a useful biochemical source of resistance against this insect. The influence of feeding by larval Colorado potato beetle on foliar polyphenol oxidase activity in tomato foliage and its possible significance to interspecific competition is also considered.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00987820
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  • 5
    Electronic Resource
    Electronic Resource
    Potential role of ascorbate oxidase as a plant defense protein against insect herbivory (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 1553-1568 
    Details
    ISSN: 1573-1561
    Keywords: Ascorbic acid ; ascorbate oxidase ; plant resistance ; plant defense ; oxidative stress ; Helicoverpa zea ; Lepidoptera ; Noctuidae ; cotton ; tomato ; soybean
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Ascorbic acid is essential for both nutritive and antioxidant functions in phytophagous insects; however, maintaining sufficient quantities of reduced ascorbate may be problematical for them. In this investigation, we show that the plant enzyme ascorbate oxidase retains activity in the digestive system of the herbivoreHelicoverpa zea. High levels of the enzyme are present in several host plants ofH. zea, including cotton, tomato, soybean, crimson clover, and vetch. The enzyme oxidizesL-ascorbic acid to dehydro-L-ascorbic acid, a potentially toxic product. The oxidation of ascorbic acid also produces active oxygen species such as the highly reactive hydroxyl radical. The nutritional quality of protein for larvalH. zea was significantly reduced by treatment with ascorbate and ascorbate oxidase. Oxidative damage to the protein was indicated by decreased lysine content, increased carbonyl formation, and the occurrence of protein fragmentation and polymerization. Furthermore, the oxidative loss of ascorbate in the herbivore's digestive system prevents ascorbate from functioning as an important antioxidant against a plethora of dietary prooxidants.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00984896
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  • 6
    Electronic Resource
    Electronic Resource
    Tetrazolverbindungen. 6. Acylierung von 1-Aryl-5-(2-dialkylamino-vinyl)-1 H-tetrazolen mittels Trifluor- und Trichloracetanhydrid (1993)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 335 (1993), S. 461-464 
    Details
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Tetrazole Compounds. 6. Acylation of 1-Aryl-5-(2-dialkylamino-vinyl)-1 H-tetrazoles by Trifluoro- and Trichloroacetic Anhydrides
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19933350513
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  • 7
    Electronic Resource
    Electronic Resource
    Tetrazolverbindungen. 7. Neuartig verknüpfte Pyrazolyl- und Isoxazolyl-tetrazole aus Enaminoketon-Vorstufen (1994)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 336 (1994), S. 79-82 
    Details
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Tetrazole Compounds. 7. New Types of Pyrazolyl- and Isoxazolyl-tetrazoles from Enamino Ketone Precursors
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19943360118
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  • 8
    Electronic Resource
    Electronic Resource
    Tetrazolverbindungen. 5. Synthese und Umaminierung von Enaminoketonen der Tetrazolreihe (1990)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 332 (1990), S. 977-994 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Tetrazole Compounds. 5. Synthesis and Transamination of Enamino Ketones of the Tetrazole SeriesTetrazole-5-acetaldehyde enamines 5 react with aliphatic and aromatic carboxylic acid chlorides in the presence of an auxiliary base (e.g. pyridine or triethylamine) to give tetrazolylsubstituted enamino ketones 6. The latter can be modified by acid-catalyzed transamination with secondary aliphatic amines (e.g. diethylamine, pyrrolidine, piperidine, morpholine, hexamethylene imine) yielding 5-(1-acyl-2-dialkylamino-vinyl)-1-aryl-1 H-tetrazoles 7. The analogue transamination of 6 with primary alkyl, aralkyl, and aryl amines results in corresponding secondary enamino ketones 8, which exist in solution as an equilibrium mixture of the Z and E form. Acylation of secondary tetrazole-5-acetaldehyde enamines 9 does not lead to 8, but to the isomeric N-acyl derivatives 10. - Characteristic 1H-n.m.r., u.v., and i.r. spectroscopic data of the novel products are reported.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19903320615
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  • 9
    Electronic Resource
    Electronic Resource
    Substituierte 2-Amino-thiazole aus α-Thiocyanato-acetophenonen und DialkylaminenHerrn Prof. Dr. K. Gewald mit den besten Wünschen zum 60. Geburtstag gewidmet (1990)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 332 (1990), S. 453-460 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Substituted 2-Amino-thiazoles from α-Thiocyanato-acetophenones and Dialkylaminesα-Thiocyanato-acetophenones 1 react with dialkylammonium salts of weak acids (acetates, propionates, benzoates) to give 2-dialkylamino-4-aryl-thiazoles 4. As reaction medium aliphatic alcohols (methanol, ethanol), dipolar-aprotic solvents (acetonitrile, dimethylformamide, dimethyl sulphoxide) or chlorinated hydrocarbons (methylene chloride, chloroform, carbon tetrachloride) can be used. In comparison to known methods for the preparation of the thiazoles 4 the synthesis via α-thiocyanato-acetophenones 1 has the advantage of the simpler accessible starting compounds. - I.r., u.v., n.m.r. and mass spectroscopic data of the thiazoles 4 are reported.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19903320405
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  • 10
    Electronic Resource
    Electronic Resource
    2-Dialkylamino-thiazolin-4-one aus α-Thiocyanato-carbonsäurederivatenHerrn Prof. Dr. G. Zimmermann mit den besten Wünschen zum 60. Geburtstag gewidmet (1990)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 332 (1990), S. 540-546 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2-Dialkylamino-thiazolin-4-ones from α-Thiocyanato-carboxylic Acid Derivativesα-Thiocyanato-acetic acid esters 1a-c or amide 1d react with dialkylamine salts of weak acids to give 2-dialkylamino-thiazolin-4-ones 2a-f. The reaction can be performed using aliphatic alcohols, dipolar aprotic solvents or halogenated hydrocarbons as reaction medium or by heating the educts at 90°C without any solvent. According to the latter method, the 5-substituted thiazolinones 2g, h are obtained from α-thiocyanatopropionic acid ethyl ester (1d) or α-thiocyanato-phenylacetic acid ethyl ester (1e) and dimethylamine acetate. - I.r., u.v. and n.m.r. data of the thiazolinones 2 are reported.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19903320419
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