Novel triterpene oxidizing activity of Arabidopsis thaliana CYP716A subfamily enzymes

Triterpenoids have diverse chemical structures and bioactivities. Cytochrome P450 monooxygenases play a key role in their structural diversification. In higher plants, CYP716A subfamily enzymes are triterpene oxidases. In this study, Arabidopsis thaliana CYP716A1 and CYP716A2 were characterized by h...

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Bibliographic Details
Published in:FEBS letters 2016-02, Vol.590 (4), p.533-540
Main Authors: Yasumoto, Shuhei, Fukushima, Ery O., Seki, Hikaru, Muranaka, Toshiya, Flügge, Ulf‐Ingo
Format: Article
Language:English
Subjects:
22α‐hydroxylation
Arabidopsis - enzymology
Arabidopsis Proteins - classification
Arabidopsis Proteins - genetics
Arabidopsis Proteins - metabolism
Arabidopsis thaliana
combinatorial biosyn‐thesis
CYP716A
Cytochrome P-450 Enzyme System - classification
Cytochrome P-450 Enzyme System - genetics
Cytochrome P-450 Enzyme System - metabolism
cytochrome P450 monooxygenase
Hydroxylation
Oleanolic Acid - analogs & derivatives
Oleanolic Acid - metabolism
Oxidation-Reduction
Phylogeny
Saccharomyces cerevisiae - genetics
Saccharomyces cerevisiae - metabolism
Triterpenes - metabolism
triterpenoids
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Summary:Triterpenoids have diverse chemical structures and bioactivities. Cytochrome P450 monooxygenases play a key role in their structural diversification. In higher plants, CYP716A subfamily enzymes are triterpene oxidases. In this study, Arabidopsis thaliana CYP716A1 and CYP716A2 were characterized by heterologously expressing them in simple triterpene‐producing yeast strains. In contrast to the C‐28 oxidative activity of CYP716A1 shown in several CYP716A subfamily enzymes, remarkably, CYP716A2 displayed 22α‐hydroxylation activity against α‐amyrin that has not been previously reported, which produces the cytotoxic triterpenoid, 22α‐hydroxy‐α‐amyrin. Our results contribute to the enrichment of the molecular toolbox that allows for the combinatorial biosynthesis of diverse triterpenoids.
ISSN:0014-5793
1873-3468
DOI:10.1002/1873-3468.12074