Structural Elucidation of 4-(Cystein-S-yl)butyl Glucosinolate from the Leaves of Eruca sativa
KIM, Sun-Ju | KAWAHARADA, Chiami | JIN, Shigeki | Hashimoto, Makoto | ISHII, Gensho | YAMAUCHI, Hiroaki
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% 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.
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