Document Detail


The biosynthesis of acetovanillone in tobacco cell-suspension cultures.
MedLine Citation:
PMID:  20188386     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A soluble enzyme, extracted from tobacco cell-suspension cultures 24h after treatment with 100 microM methyl jasmonate, has been shown to synthesize acetovanillone (apocynin) from feruloyl-CoA in the presence of NAD. The enzyme displayed Michaelis-Menten kinetics with apparent K(m) values of 5.6 microM for feruloyl-CoA and 260 microM for NAD and exhibited very high specificity for its substrates. The increase in acetovanillone synthase activity was followed by an increase in the concentration of both acetovanillone and acetosyringone in the culture medium. No intermediate could be detected when analysing the reaction medium by HPLC during the formation of acetovanillone in cell-free extracts. The apparent molecular mass estimated by gel permeation on an FPLC column was ca. 79 kDa. To our knowledge, this is the first report of an enzymic system catalysing the synthesis of an acetophenone. This work demonstrates that the biosynthesis of acetophenones in tobacco proceeds from hydroxycinnamic acids through a CoA-dependent beta-oxidation pathway. Interestingly in methyl jasmonate-treated cells, which synthesize very large amounts of hydroxycinnamoylputrescines, inhibition of the synthesis of these conjugates increased the concentration of acetovanillone and acetosyringone in the culture medium, suggesting that the two metabolic pathways can compete for their common precursors, i.e. hydroxycinnamoyl-CoA thioesters.
Authors:
Jonathan Negrel; Francine Javelle
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Publication Detail:
Type:  Journal Article     Date:  2010-02-24
Journal Detail:
Title:  Phytochemistry     Volume:  71     ISSN:  1873-3700     ISO Abbreviation:  Phytochemistry     Publication Date:  2010 May 
Date Detail:
Created Date:  2010-04-07     Completed Date:  2010-08-02     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0151434     Medline TA:  Phytochemistry     Country:  United States    
Other Details:
Languages:  eng     Pagination:  751-9     Citation Subset:  IM    
Copyright Information:
Copyright 2010 Elsevier Ltd. All rights reserved.
Affiliation:
INRA, UMR Plante-Microbe-Environnement, Dijon, France. negrel@dijon.inra.fr
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MeSH Terms
Descriptor/Qualifier:
Acetophenones / chemistry,  metabolism*
Cell-Free System
Cells, Cultured
Chromatography, Gel
Chromatography, High Pressure Liquid
Culture Media
Gas Chromatography-Mass Spectrometry
Molecular Weight
Tobacco / cytology,  metabolism*
Chemical
Reg. No./Substance:
0/Acetophenones; 0/Culture Media; 498-02-2/acetovanillone

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


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