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Structural elucidation of 4-(cystein-S-yl)butyl glucosinolate from the leaves of Eruca sativa

Kim, S.J.(National Agricultural Research Center for Hokkaido Region, Memuro (Japan)) ; Kawaharada, C ; Jin, S ; Hashimoto, M ; Ishii, G ; Yamauchi, H

Bioscience, biotechnology, and biochemistry, 2007-01, Vol.71 (1), p.114-121 [Periódico revisado por pares]

Tokyo: Japan Society for Bioscience, Biotechnology, and Agrochemistry

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Título:
Structural elucidation of 4-(cystein-S-yl)butyl glucosinolate from the leaves of Eruca sativa
Autor: Kim, S.J.(National Agricultural Research Center for Hokkaido Region, Memuro (Japan)) ; Kawaharada, C ; Jin, S ; Hashimoto, M ; Ishii, G ; Yamauchi, H
Assuntos: 4-mercaptobutyl glucosinolate ; ammonia detoxification ; Biological and medical sciences ; Brassicaceae - chemistry ; Brassicaceae - drug effects ; Brassicaceae - metabolism ; CHEMICAL STRUCTURE ; CISTEINA ; CYSTEINE ; Cysteine - analogs & derivatives ; Cysteine - biosynthesis ; Cysteine - chemistry ; electrospray ionization mass spectrometry (ESI-MS)/MS ; ERUCA SATIVA ; ESPECTROMETRIA DE MASAS ; ESPECTROSCOPIA RMN ; ESTRUCTURA QUIMICA ; EXTRACCION ; EXTRACTION ; FEUILLE ; Fundamental and applied biological sciences. Psychology ; GLUCOSIDE ; GLUCOSIDES ; GLUCOSIDOS ; Glucosinolates - biosynthesis ; Glucosinolates - chemistry ; HIDROCARBUROS ; HOJAS ; HYDROCARBONS ; HYDROCARBURE ; L-Ser ; LEAVES ; MASS SPECTROMETRY ; Molecular Structure ; Nitrates - pharmacology ; NMR SPECTROSCOPY ; Plant Leaves - chemistry ; Plant Leaves - drug effects ; Plant Leaves - metabolism ; PURIFICACION ; PURIFICATION ; Quaternary Ammonium Compounds - pharmacology ; rocket salad (Eruca sativa Mill.) ; SPECTROMETRIE DE MASSE ; Spectrometry, Mass, Electrospray Ionization ; SPECTROSCOPIE RMN ; STRUCTURE CHIMIQUE ; Tandem Mass Spectrometry
É parte de: Bioscience, biotechnology, and biochemistry, 2007-01, Vol.71 (1), p.114-121
Notas: Q04
2007006156
ObjectType-Article-1
SourceType-Scholarly Journals-1
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Descrição: The structurally unique glucosinolate (GSL), 4-(cystein-S-yl)butyl GSL, was identified in the leaves of hydroponically-grown rocket salad (Eruca sativa Mill.). Its electrospray ionization mass spectrometry (ESI-MS)/MS spectrum indicated that this unusual GSL had a molecular weight of 414 as a desulfo (DS)-GSL, and a molecular formula of C14H25N2O8S2 based on its negative ion matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF-MS) spectrum. For further confirmation, the 4-(cystein-S-yl)butyl DS-GSL was prepared with authentic L-Ser and purified dimeric 4-mercaptobutyl DS-GSL, and its chemical structure then confirmed by ESI-MS/MS data. It is named 'glucorucolamine' as a trivial name from its ammonia sensitivity. This unique GSL was found to the greatest extent when rocket salad was grown in a 100% NH4sup(+)-N nutrient solution. Despite it clearly seems to reduce the detoxification of excess NH4sup(+) in the leaves of rocket salad, present knowledge about the unique GSL is still far from being sufficient.
Editor: Tokyo: Japan Society for Bioscience, Biotechnology, and Agrochemistry
Idioma: Inglês

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Structural elucidation of 4-(cystein-S-yl)butyl glucosinolate from the leaves of Eruca sativa

Kim, S.J.(National Agricultural Research Center for Hokkaido Region, Memuro (Japan)) ; Kawaharada, C ; Jin, S ; Hashimoto, M ; Ishii, G ; Yamauchi, H

Tokyo: Japan Society for Bioscience, Biotechnology, and Agrochemistry

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