Document Detail

Identification of the major glucosinolate (4-mercaptobutyl glucosinolate) in leaves of Eruca sativa L. (salad rocket).
MedLine Citation:
PMID:  12165298     Owner:  NLM     Status:  MEDLINE    
The major and structurally unique glucosinolate (GLS) in leaves of Eruca sativa L. (salad rocket) was identified as 4-mercaptobutyl GLS. Both 4-methylthiobutyl GLS and 4-methylsulfinylbutyl GLS were also present, but at lower concentrations. The 4-mercaptobutyl GLS was observed to oxidise under common GLS extraction conditions, generating a disulfide GLS that may be reduced efficiently by tris(2-carboxyethyl) phosphine hydrochloride (TCEP) to reform the parent molecule. The identities of 4-mercaptobutyl GLS and of the corresponding dimeric GLS were confirmed by LC/MS, MS/MS and NMR. Myrosinase treatment of an enriched GLS fraction or of the purified dimer GLS generated a mixture of unique bi-functional disulfides, including bis-(4-isothiocyanatobutyl) disulfide (previously identified elsewhere). TCEP reduction of the purified dimer, followed by myrosinase treatment, yielded only 4-mercaptobutyl ITC. GLS-derived volatiles generated by autolysis of fresh seedlings and true leaves were 4-mercaptobutyl ITC (from the newly identified GLS), 4-methylthiobutyl ITC (from 4-methylthiobutyl GLS) and 4-methylsulfinylbutyl ITC (from 4-methylsulfinyl-butyl GLS); no unusual bi-functional disulfides were found in fresh leaf autolysate. These results led to the conclusion that, in planta, the new GLS must be present as 4-mercaptobutyl GLS and not as the disulfide found after extraction and sample concentration. This new GLS and its isothiocyanate are likely to contribute to the unique odour and flavour of E. sativa.
Richard N Bennett; Fred A Mellon; Nigel P Botting; John Eagles; Eduardo A S Rosa; Gary Williamson
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Phytochemistry     Volume:  61     ISSN:  0031-9422     ISO Abbreviation:  Phytochemistry     Publication Date:  2002 Sep 
Date Detail:
Created Date:  2002-08-07     Completed Date:  2002-12-11     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0151434     Medline TA:  Phytochemistry     Country:  United States    
Other Details:
Languages:  eng     Pagination:  25-30     Citation Subset:  IM    
Copyright Information:
Copyright 2002 Elsevier Science Ltd.
Institute of Food Research, Norwich Research Park, Colney, Norwich NR4 7UA, UK.
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MeSH Terms
Brassicaceae / chemistry*
Chromatography, Liquid
Glucosinolates / analysis*,  chemistry,  isolation & purification
Magnetic Resonance Spectroscopy
Mass Spectrometry
Plant Leaves / chemistry*
Spectrometry, Mass, Electrospray Ionization
Reg. No./Substance:
0/4-mercaptobutyl glucosinolate; 0/Glucosinolates

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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