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Two cytochromes P450 catalyze S-heterocyclizations in cabbage phytoalexin biosynthesis

Nature Chemical Biology volume 11, pages 837–839 (2015)Cite this article

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Abstract

Phytoalexins are abundant in edible crucifers and have important biological activities, yet no dedicated gene for their biosynthesis is known. Here, we report two new cytochromes P450 from Brassica rapa (Chinese cabbage) that catalyze unprecedented S-heterocyclizations in cyclobrassinin and spirobrassinin biosynthesis. Our results provide genetic and biochemical insights into the biosynthesis of a prominent pair of dietary metabolites and have implications for pathway discovery across >20 recently sequenced crucifers.

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Figure 1: Phytoalexins in Brassica rapa.
Figure 2: Phytoalexin production in B. rapa and in vitro analysis of CYPs in cruciferous phytoalexin biosynthesis.
Figure 3: Occurrence of CYP71CR genes and phytoalexins across the Brassicaceae family.

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GenBank/EMBL/DDBJ

Gene Expression Omnibus

NCBI Reference Sequence

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Acknowledgements

This work was supported by the US National Institutes of Health grants R00 GM089985 and DP2 AT008321 (E.S.S.). A.P.K. was supported by the US National Defense Science and Engineering Graduate Fellowship. We thank M. Jin (Korea Brassica Genome Project) and H.B. Lauffer (Wisconsin Fast Plants Program) for providing seeds. We thank X. Ji (Stanford Functional Genomics Facility) for RNA sequencing services. We thank L. Meyer-Teruel for help in initial metabolic profiling of B. rapa, J.-G. Kim and L. Sassoubre for qRT-PCR assistance, D. Nelson for CYP nomenclature assignment and S. Galanie and members of the Sattely Group for helpful comments on the manuscript.

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  1. Department of Chemical Engineering, Stanford University, Stanford, California, USA

    Andrew P Klein & Elizabeth S Sattely

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  1. Andrew P Klein
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  2. Elizabeth S Sattely
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A.P.K. and E.S.S. designed the study. A.P.K. performed all experiments. A.P.K. and E.S.S. analyzed the data and wrote the manuscript.

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Correspondence to Elizabeth S Sattely.

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Supplementary Results, Supplementary Figures 1–17 and Supplementary Tables 1–8. (PDF 13517 kb)

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Klein, A., Sattely, E. Two cytochromes P450 catalyze S-heterocyclizations in cabbage phytoalexin biosynthesis. Nat Chem Biol 11, 837–839 (2015). https://doi.org/10.1038/nchembio.1914

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