Structural elucidation of 4-(cystein-S-yl)butyl glucosinolate from the leaves of Eruca sativa.
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.
Kim
Sun-Ju
SJ
National Agricultural Research Center for Hokkaido Region, Japan. kimsunju@affrc.go.jp
Kawaharada
Chiami
C
Jin
Shigeki
S
Hashimoto
Makoto
M
Ishii
Gensho
G
Yamauchi
Hiroaki
H
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
C518436:4-(cystein-S-yl)butyl glucosinolate; D005961:Glucosinolates; D009566:Nitrates; D000644:Quaternary Ammonium Compounds; D003545:Cysteine