title: Structural elucidation of 4-(cystein-S-yl)butyl glucosinolate from the leaves of Eruca sativa.
abstract: 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 C(14)H(25)N(2)O(8)S(2) 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% NH4+-N nutrient solution. Despite it clearly seems to reduce the detoxification of excess NH4+ in the leaves of rocket salad, present knowledge about the unique GSL is still far from being sufficient.
authors.affiliation: National Agricultural Research Center for Hokkaido Region, Japan. kimsunju@affrc.go.jp
authors.forename: Sun-Ju
authors.initials: SJ
authors.lastname: Kim
authors.forename: Chiami
authors.initials: C
authors.lastname: Kawaharada
authors.forename: Shigeki
authors.initials: S
authors.lastname: Jin
authors.forename: Makoto
authors.initials: M
authors.lastname: Hashimoto
authors.forename: Gensho
authors.initials: G
authors.lastname: Ishii
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Yamauchi
mesh_terms: D019607:Brassicaceae / Q000737:chemistry* / Q000187:drug effects / Q000378:metabolism; D003545:Cysteine / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000737:chemistry; D005961:Glucosinolates / Q000096:biosynthesis / Q000737:chemistry*; D015394:Molecular Structure; D009566:Nitrates / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry / Q000187:drug effects / Q000378:metabolism; D000644:Quaternary Ammonium Compounds / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D053719:Tandem Mass Spectrometry
chemical_list: C518436:4-(cystein-S-yl)butyl glucosinolate; D005961:Glucosinolates; D009566:Nitrates; D000644:Quaternary Ammonium Compounds; D003545:Cysteine