Document Detail

Chlorogenic acid biosynthesis: characterization of a light-induced microsomal 5-O-(4-coumaroyl)-D-quinate/shikimate 3'-hydroxylase from carrot (Daucus carota L.) cell suspension cultures.
MedLine Citation:
PMID:  2821918     Owner:  NLM     Status:  MEDLINE    
Microsomal preparations from carrot (Daucus carota L.) cell suspension cultures catalyze the formation of trans-5-O-caffeoyl-D-quinate (chlorogenate) from trans-5-O-(4-coumaroyl)-D-quinate. trans-5-O-(4-Coumaroyl)shikimate is converted to about the same extent to trans-5-O-caffeoylshikimate. trans-4-O-(4-Coumaroyl)-D-quinate, trans-3-O-(4-coumaroyl)-D-quinate, trans-4-coumarate, and cis-5-O-(4-coumaroyl)-D-quinate do not act as substrates. The reaction is strictly dependent on molecular oxygen and on NADPH as reducing cofactor. NADH and ascorbic acid cannot substitute for NADPH. Cytochrome c, Tetcyclacis, and carbon monoxide inhibit the reaction suggesting a cytochrome P-450-dependent mixed-function monooxygenase. Competition experiments as well as induction and inhibition phenomena indicate that there is only one enzyme species which is responsibl for the hydroxylation of the 5-O-(4-coumaric) esters of both D-quinate and shikimate. The activity of this enzyme is greatly increased by in vivo irradiation of the cells with blue/uv light. We conclude that the biosynthesis of the predominant caffeic acid conjugates in carrot cells occurs via the corresponding 4-coumaric acid esters. Thus, in this system, 5-O-(4-coumaroyl)-D-quinate can be seen as the final intermediate in the chlorogenic acid pathway.
T Kühnl; U Koch; W Heller; E Wellmann
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Archives of biochemistry and biophysics     Volume:  258     ISSN:  0003-9861     ISO Abbreviation:  Arch. Biochem. Biophys.     Publication Date:  1987 Oct 
Date Detail:
Created Date:  1987-11-12     Completed Date:  1987-11-12     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0372430     Medline TA:  Arch Biochem Biophys     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  226-32     Citation Subset:  IM    
Biologisches Institut II, Universität Freiburg, Federal Republic of Germany.
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MeSH Terms
Carbon Monoxide / pharmacology
Cells, Cultured
Chlorogenic Acid / metabolism*
Cytochrome c Group / pharmacology
Microsomes / enzymology
Mixed Function Oxygenases / antagonists & inhibitors,  metabolism*,  radiation effects
NADP / pharmacology
Oxygen / pharmacology
Plants / enzymology*
Substrate Specificity
Triazoles / pharmacology
Reg. No./Substance:
0/Cytochrome c Group; 0/Triazoles; 327-97-9/Chlorogenic Acid; 53-59-8/NADP; 630-08-0/Carbon Monoxide; 65245-23-0/tetcyclacis; 7782-44-7/Oxygen; EC 1.-/Mixed Function Oxygenases; EC 1.14.13.-/5-O-(4-coumaroyl)shikimate 3'-hydroxylase

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

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