Isolation and structural elucidation of 4-(beta-D-glucopyranosyldisulfanyl)butyl glucosinolate from leaves of rocket salad (Eruca sativa L.) and its antioxidative activity.
A structurally unique glucosinolate (GSL) was identified to be 4-(beta-D-glucopyranosyldisulfanyl)butyl GSL in rocket leaves. The positive-ion electrospray ionization mass spectrometry (ESI-MS) data indicated that the new GSL had a molecular weight of 521 (m/z 522, [M+H](+), as desulfo-GSL). The molecular formula of the substance was determined to be C(17)H(32)O(11)NS(3) (m/z 522.1143, [M+H](+)) based on its positive-ion high-resolution fast atom bombardment mass spectrometry (HR-FAB-MS) data. For the further confirmation, desulfated GSL of 4-(beta-D-glucopyranosyldisulfanyl)butyl GSL was prepared by commercial 1-thio-beta-D-glucose and dimeric 4-mercaptobutyl desulfo-GSL, which was also isolated from rocket leaves, and its chemical structure was then confirmed by MS data and nuclear magnetic resonance (NMR) spectroscopy. In addition, the antioxidative activity of 4-(beta-D-glucopyranosyldisulfanyl)butyl desulfo-GSL was measured by means of chemiluminescence (CL) for evaluating the functional properties. The antioxidative activity (2.089 unit/g) was relatively higher than that of dimeric 4-mercaptobutyl desulfo-GSL (1.227).
Kim
Sun-Ju
SJ
National Agricultural Research Center for Hokkaido Region, Toyohira-ku, Sapporo 062-8555, Japan.
Jin
Shigeki
S
Ishii
Gensho
G
D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D019607:Brassicaceae / Q000737:chemistry*; D004220:Disulfides / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D005961:Glucosinolates / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D008163:Luminescent Measurements; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry
C501230:4-(glucopyranosyldisulfanyl)butyl glucosinolate; D000975:Antioxidants; D004220:Disulfides; D005961:Glucosinolates