A chicory cytochrome P450 mono-oxygenase CYP71AV8 for the oxidation of (+)-valencene.
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.
Laboratory of Plant Physiology, Wageningen University and Research Centre, Wageningen, The Netherlands.
Katarina
K
Cankar
Adèle
A
van Houwelingen
Dirk
D
Bosch
Theo
T
Sonke
Harro
H
Bouwmeester
Jules
J
Beekwilder
D055162:Biocatalysis; D018651:Cichorium intybus / Q000201:enzymology* / Q000235:genetics; D003001:Cloning, Molecular; D003577:Cytochrome P-450 Enzyme System / Q000235:genetics / Q000378:metabolism*; D018076:DNA, Complementary / Q000737:chemistry / Q000235:genetics; D020224:Expressed Sequence Tags; D015723:Gene Library; D008969:Molecular Sequence Data; D010084:Oxidation-Reduction; D010088:Oxidoreductases / Q000235:genetics / Q000378:metabolism; D010940:Plant Proteins / Q000235:genetics / Q000378:metabolism*; D000081223:Polycyclic Sesquiterpenes; D017422:Sequence Analysis, DNA; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism*; D045788:Sesquiterpenes, Germacrane / Q000378:metabolism; D013237:Stereoisomerism; D015003:Yeasts / Q000235:genetics / Q000378:metabolism
D018076:DNA, Complementary; D010940:Plant Proteins; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D045788:Sesquiterpenes, Germacrane; C431525:germacra-1(10),4,11(13)-trien-12-oic acid; C471077:germacrene A; C041991:Nootkatol; D003577:Cytochrome P-450 Enzyme System; C506706:valencene; D010088:Oxidoreductases; C050302:nootkatone