Isolation and structure elucidation of a new thermal breakdown product of glucobrassicin, the parent indole glucosinolate

Journal of Agricultural and Food Chemistry

Volumn 50, Issue 18, 2002, Pages 5185-5190

  Chevolleau, Sylvie ^a   Debrauwer, Laurent ^a   Boyer, Gérard ^b   Tulliez, Jacques ^a  

^a CNRS   (France)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Anticarcinogenic substances; Glucobrassicin; Glucosinolates; Indole condensation product; Indole derivatives; Structure elucidation; Thermal breakdown

Indexed keywords

GLUCOBRASSICIN; GLUCOSINOLATE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DEGRADATION; HEAT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; TANDEM MASS SPECTROMETRY; VEGETABLE; ELECTROSPRAY MASS SPECTROMETRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLUCOSINOLATES; HEAT; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 0037189872     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf020125i     Document Type: Article

References (32)

1. The chemical diversity and distribution of glucosinolates and isothiocyanates among plants
2. Glucosinolates and their breakdown products in food and food plants
3. Chemical and biological properties of indole glucosinolates (Glucobrassicins): A review
4. Modification of carcinogen metabolism by indolylic autolysis products of Brassica oleraceae
5. Modulation of cytochrome P-450 and glutathione S-transferase isoform expression in vivo by intact and degraded indolyl glucosinolates
6. Selective cytostatic and cytotoxic effects of glucosinolates hydrolysis products on human colon cancer cells in vitro
7. Progress in cancer chemoprevention: Development of diet-derived chemopreventive agents
8. Formation of indole glucosinolate breakdown products in autolyzed, steamed and cooked Brassica vegetables
9. Indoleacetonitriles - Thermal degradation products of indole glucosinolates in commercial rapeseed (Brassica napus) meal
10. Chemistry of indole glucosinolates: Intermediacy of indol-3-ylmethyl isothiocyanates in the enzymatic hydrolysis of indole glucosinolates
11. High performance liquid chromatographic analysis of anticarcinogenic indoles in Brassica oleracea
12. Role of glucosinolates in the formation of N-nitroso compounds
13. 3H-labeled glucobrassicin, the parent indole glucosinolate
14. 3H]-labelled glucobrassicin, a potential radiotracer for metabolic studies of indole glucosinolates
15. First synthesis of an indole glucosinolate
16. Synthetic studies on indole glucosinolates. Part 1. Synthesis of glucobrassicin ands its 4- and 5-methoxy derivatives
17. Condensation of 3-hydroxymethylindoles with 3-substituted indoles. Formation of 2,3′-methylenediindole derivatives
18. Mechanisms of tumor modulation by indole-3-carbinol. Disposition and excretion in male Fisher 344 rats
19. Structure elucidation of acid reaction products of indole-3-carbinol: Detection in vivo and enzyme induction in vitro
20. Oligomerization of indole-3-carbinol in aqueous acid
21. Cytostatic and antiestrogenic effects of 2-(indol-3-ylmethyl)-3,3′-diindolylmethane, a major in vivo product of dietary indole-3-carbinol
22. Modulation of drug-metabolising enzyme expression by condensation products of indole-3-ylcarbinol, an inducer in cruciferous vegetables
23. The major cyclic trimeric product of indole-3-carbinol is a strong agonist of the estrogen receptor signaling pathway
24. Electrophilic substitution in indoles. V. Indolenines as intermediates in the benzylation of 3-subtituted indoles
25. Electrophilic substitution in indoles: Direct attack at the 2-position of 3-alkylindoles
26. -, 3-indolylacetonitril und ascorbigen in Brassica oleracea species
27. Occurrence, isolation, and properties of glucobrassicin and neoglucobrassicin
28. Indoles in edible members of the Cruciferae