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Tripterygium wilfordii cytochrome P450s catalyze the methyl shift and epoxidations in the biosynthesis of triptonide
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Tripterygium wilfordii cytochrome P450s catalyze the methyl shift and epoxidations in the biosynthesis of triptonide
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Journal Article
Tripterygium wilfordii cytochrome P450s catalyze the methyl shift and epoxidations in the biosynthesis of triptonide
2022
Overview
The diterpenoid triepoxides triptolide and triptonide from
Tripterygium wilfordii
(thunder god wine) exhibit unique bioactivities with potential uses in disease treatment and as a non-hormonal male contraceptives. Here, we show that cytochrome P450s (CYPs) from the CYP71BE subfamily catalyze an unprecedented 18(4→3) methyl shift required for biosynthesis of the abeo-abietane core structure present in diterpenoid triepoxides and in several other plant diterpenoids. In combination with two CYPs of the CYP82D subfamily, four CYPs from
T. wilfordii
are shown to constitute the minimal set of biosynthetic genes that enables triptonide biosynthesis using
Nicotiana benthamiana
and
Saccharomyces cerevisiae
as heterologous hosts. In addition, co-expression of a specific
T. wilfordii
cytochrome
b
5
(
Tw
cyt
b
5
-A) increases triptonide output more than 9-fold in
S. cerevisiae
and affords isolation and structure elucidation by NMR spectroscopic analyses of 18 diterpenoids, providing insights into the biosynthesis of diterpenoid triepoxides. Our findings pave the way for diterpenoid triepoxide production via fermentation.
How triptonide is made in the medicinal plant
Tripterygium wilfordii
is largely unknown. Here, the authors report the identification and characterization of a suite of cytochrome P450s and show their function in catalyzing the formation of triptonide from miltriadiene in tobacco and baker’s yeast.
Publisher
Nature Publishing Group UK,Nature Publishing Group,Nature Portfolio
