A Stereoselective Hydroxylation Step of Alkaloid Biosynthesis by a Unique Cytochrome P450 in Catharanthus roseus

Authors

Lesley Ann Giddings, Massachusetts Institute of TechnologyFollow
David K. Liscombe, Massachusetts Institute of Technology
John P. Hamilton, Michigan State University
Kevin L. Childs, Michigan State University
Dean DellaPenna, Michigan State University
C. Robin Buell, Michigan State University
Sarah E. O'Connor, Massachusetts Institute of Technology

Document Type

Article

Publication Date

5-13-2011

Publication Title

Journal of Biological Chemistry

Abstract

Plant cytochrome P450s are involved in the production of over a hundred thousand metabolites such as alkaloids, terpenoids, and phenylpropanoids. Although cytochrome P450 genes constitute one of the largest superfamilies in plants, many of the catalytic functions of the enzymes they encode remain unknown. Here, we report the identification and functional characterization of a cytochrome P450 gene in a new subfamily of CYP71, CYP71BJ1, involved in alkaloid biosynthesis. Co-expression analysis of putative cytochrome P450 genes in the Catharanthus roseus transcriptome identified candidate genes with expression profiles similar to known terpene indole alkaloid biosynthetic genes. Screening of these candidate genes by functional expression in Saccharomyces cerevisiae yielded a unique P450-dependent enzyme that stereoselectively hydroxylates the alkaloids tabersonine and lochnericine at the 19-position of the aspidosperma-type alkaloid scaffold. Tabersonine, which can be converted to either vindoline or 19-O-acetylhörhammericine, represents a branch point in alkaloid biosynthesis. The discovery of CYP71BJ1, which forms part of the pathway leading to 19-O-acetylhörhammericine, will help illuminate how this branch point is controlled in C. roseus.

Volume

286

Issue

19

First Page

16751

Last Page

16757

DOI

10.1074/jbc.M111.225383

ISSN

00219258

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Rights

©2011 by The American Society for Biochemistry and Molecular Biology, Inc.

Comments

Archived as published.

Recommended Citation

Giddings, Lesley Ann; Liscombe, David K.; Hamilton, John P.; Childs, Kevin L.; DellaPenna, Dean; Buell, C. Robin; and O'Connor, Sarah E., "A Stereoselective Hydroxylation Step of Alkaloid Biosynthesis by a Unique Cytochrome P450 in Catharanthus roseus" (2011). Chemistry: Faculty Publications, Smith College, Northampton, MA.
https://scholarworks.smith.edu/chm_facpubs/58