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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

Journal Article · · Arch. Biochem. Biophys.; (United States)
; ; ;

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 responsible 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.

Research Organization:
Universitaet Freiburg, Germany, F.R.
OSTI ID:
5840355
Journal Information:
Arch. Biochem. Biophys.; (United States), Journal Name: Arch. Biochem. Biophys.; (United States) Vol. 258:1; ISSN ABBIA
Country of Publication:
United States
Language:
English

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Related Subjects

560120* -- Radiation Effects on Biochemicals
Cells
& Tissue Culture
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AZOLES
BIOLOGICAL EFFECTS
BIOLOGICAL RADIATION EFFECTS
BIOSYNTHESIS
CARBON COMPOUNDS
CARBON MONOXIDE
CARBON OXIDES
CARBOXYLIC ACIDS
CARROTS
CELL CONSTITUENTS
CELL CULTURES
CHALCOGENIDES
CHEMICAL COMPOSITION
COENZYMES
ELECTROMAGNETIC RADIATION
ELEMENTS
ENZYMES
FOOD
HETEROCYCLIC COMPOUNDS
HYDROXYLASES
MICROSOMES
MIXED-FUNCTION OXIDASES
NADP
NONMETALS
NUCLEOTIDES
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANOIDS
OXIDES
OXIDOREDUCTASES
OXYGEN
OXYGEN COMPOUNDS
OXYGENASES
PLANT CELLS
PLANTS
RADIATION EFFECTS
RADIATIONS
SYNTHESIS
TRIAZOLES
ULTRAVIOLET RADIATION
VEGETABLES