Abstract
Chicory (Cichorium intybus L.), which is known to have a variety of terpene-hydroxylating activities, was screened for a P450 mono-oxygenase to convert (+)-valencene to (+)-nootkatone. A novel P450 cDNA was identified in a chicory root EST library. Co-expression of the enzyme with a valencene synthase in yeast, led to formation of trans-nootkatol, cis-nootkatol and (+)-nootkatone. The novel enzyme was also found to catalyse a three step conversion of germacrene A to germacra-1(10),4,11(13)-trien-12-oic acid, indicating its involvement in chicory sesquiterpene lactone biosynthesis. Likewise, amorpha-4,11-diene was converted to artemisinic acid. Surprisingly, the chicory P450 has a different regio-specificity on (+)-valencene compared to germacrene A and amorpha-4,11-diene.
Copyright © 2010 Federation of European Biochemical Societies. Published by Elsevier B.V. All rights reserved.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Biocatalysis
-
Cichorium intybus / enzymology*
-
Cichorium intybus / genetics
-
Cloning, Molecular
-
Cytochrome P-450 Enzyme System / genetics
-
Cytochrome P-450 Enzyme System / metabolism*
-
DNA, Complementary / chemistry
-
DNA, Complementary / genetics
-
Expressed Sequence Tags
-
Gene Library
-
Molecular Sequence Data
-
Oxidation-Reduction
-
Oxidoreductases / genetics
-
Oxidoreductases / metabolism
-
Plant Proteins / genetics
-
Plant Proteins / metabolism*
-
Polycyclic Sesquiterpenes
-
Sequence Analysis, DNA
-
Sesquiterpenes / chemistry
-
Sesquiterpenes / metabolism*
-
Sesquiterpenes, Germacrane / metabolism
-
Stereoisomerism
-
Yeasts / genetics
-
Yeasts / metabolism
Substances
-
DNA, Complementary
-
Plant Proteins
-
Polycyclic Sesquiterpenes
-
Sesquiterpenes
-
Sesquiterpenes, Germacrane
-
germacra-1(10),4,11(13)-trien-12-oic acid
-
germacrene A
-
Nootkatol
-
Cytochrome P-450 Enzyme System
-
valencene
-
Oxidoreductases
-
nootkatone