1,4-Dimethoxyglucobrassicin in Barbarea and 4-Hydroxyglucobrassicin in Arabidopsis and Brassica

A novel indole glucosinolate, 1,4-dimethoxyglucobrassicin (1,4-dimethoxyindol-3-ylmethylglucosinolate), was isolated as the desulfo derivative from roots of the P-type of Barbarea vulgaris ssp. arcuata, and its structure was determined by spectroscopy including 2D NMR spectroscopy. 4-Hydroxyglucobra...

Full description

Saved in:
Bibliographic Details
Published in:Journal of agricultural and food chemistry 2001-03, Vol.49 (3), p.1502-1507
Main Authors: Agerbirk, Niels, Petersen, Bent Larsen, Olsen, Carl Erik, Halkier, Barbara Ann, Nielsen, Jens Kvist
Format: Article
Language:English
Subjects:
Agronomy. Soil science and plant productions
Arabidopsis - chemistry
Biological and medical sciences
Brassica - chemistry
Brassicaceae - chemistry
Chemical constitution
Economic plant physiology
Fundamental and applied biological sciences. Psychology
Glucosinolates
Indoles - chemistry
Indoles - isolation & purification
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Conformation
Molecular Structure
Monosaccharides - chemistry
Monosaccharides - isolation & purification
Plant physiology and development
Vegetables - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A novel indole glucosinolate, 1,4-dimethoxyglucobrassicin (1,4-dimethoxyindol-3-ylmethylglucosinolate), was isolated as the desulfo derivative from roots of the P-type of Barbarea vulgaris ssp. arcuata, and its structure was determined by spectroscopy including 2D NMR spectroscopy. 4-Hydroxyglucobrassicin (4-hydroxyindol-3-ylmethylglucosinolate) was isolated as the desulfo derivative from green siliques (fruits) of Arabidopsis thaliana and identified by comparison of its 1H NMR spectrum with the spectrum of the known desulfoglucosinolate from Brassica napus. The delayed elution of desulfo indole glucosinolates from the DEAE Sephadex column used in sample preparation was examined, and the diode-array UV spectra of desulfo indole glucosinolates were measured, to ensure a reliable determination of 1,4-dimethoxyglucobrassicin and 4-hydroxyglucobrassicin with the existing analysis method based on the HPLC of desulfoglucosinolates. 1,4-Dimethoxyglucobrassicin was not detected in 10 other Arabidopsis, Brassica, and Barbarea species, indicating an evolutionarily recent mutation in the indole glucosinolate biosynthesis in B. vulgaris ssp. arcuata type P. Keywords: Brassicaceae; Barbarea; Arabidopsis; Brassica; 1,4-dimethoxyindol-3-ylmethylglucosinolate; 1,4-dimethoxyglucobrassicin; 4-hydroxyindol-3-ylmethylglucosinolate; 4-hydroxyglucobrassicin; desulfoglucosinolate; indole phytoalexin; NMR; MS; UV; HPLC
ISSN:0021-8561
1520-5118
DOI:10.1021/jf001256r