Characterization of CYP71AX36 from Sunflower (Helianthus annuus L., Asteraceae).

Abstract:

:Sesquiterpene lactones (STL) are a subclass of isoprenoids with many known bioactivities frequently found in the Asteraceae family. In recent years, remarkable progress has been made regarding the biochemistry of STL, and today the biosynthetic pathway of the core backbones of many STLs has been elucidated. Consequently, the focus has shifted to the discovery of the decorating enzymes that can modify the core skeleton with functional hydroxy groups. Using in vivo pathway reconstruction assays in heterologous organisms such as Saccharomyces cerevisiae and Nicotiana benthamiana, we have analyzed several cytochrome P450 enzyme genes of the CYP71AX subfamily from Helianthus annuus clustered in close proximity to one another on the sunflower genome. We show that one member of this subfamily, CYP71AX36, can catalyze the conversion of costunolide to 14-hydroxycostunolide. The catalytic activity of CYP71AX36 may be of use for the chemoenzymatic production of antileukemic 14-hydroxycostunolide derivatives and other STLs of pharmaceutical interest. We also describe the full 2D-NMR assignment of 14-hydroxycostunolide and provide all 13C chemical shifts of the carbon skeleton for the first time.

journal_name

Sci Rep

journal_title

Scientific reports

authors

Frey M,Klaiber I,Conrad J,Bersch A,Pateraki I,Ro DK,Spring O

doi

10.1038/s41598-019-50520-6

subject

Has Abstract

pub_date

2019-10-04 00:00:00

pages

14295

issue

1

issn

2045-2322

pii

10.1038/s41598-019-50520-6

journal_volume

9

pub_type

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