Repeated evolution of cytochrome P450-mediated spiroketal steroid biosynthesis in plants

Bastien Christ, Chengchao Xu, Menglong Xu, Fu-Shuang Li, Naoki Wada, Andrew J. Mitchell, Xiu-Lin Han, Meng-Liang Wen, Makoto Fujita and Jing-Ke Weng ()
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Bastien Christ: Whitehead Institute for Biomedical Research
Chengchao Xu: Whitehead Institute for Biomedical Research
Menglong Xu: Whitehead Institute for Biomedical Research
Fu-Shuang Li: Whitehead Institute for Biomedical Research
Naoki Wada: The University of Tokyo
Andrew J. Mitchell: Whitehead Institute for Biomedical Research
Xiu-Lin Han: Yunnan Institute of Microbiology, School of Life Sciences, Yunnan University
Meng-Liang Wen: Yunnan Institute of Microbiology, School of Life Sciences, Yunnan University
Makoto Fujita: The University of Tokyo
Jing-Ke Weng: Whitehead Institute for Biomedical Research

Nature Communications, 2019, vol. 10, issue 1, 1-11

Abstract: Abstract Diosgenin is a spiroketal steroidal natural product extracted from plants and used as the single most important precursor for the world steroid hormone industry. The sporadic occurrences of diosgenin in distantly related plants imply possible independent biosynthetic origins. The characteristic 5,6-spiroketal moiety in diosgenin is reminiscent of the spiroketal moiety present in anthelmintic avermectins isolated from actinomycete bacteria. How plants gained the ability to biosynthesize spiroketal natural products is unknown. Here, we report the diosgenin-biosynthetic pathways in himalayan paris (Paris polyphylla), a monocot medicinal plant with hemostatic and antibacterial properties, and fenugreek (Trigonella foenum–graecum), an eudicot culinary herb plant commonly used as a galactagogue. Both plants have independently recruited pairs of cytochromes P450 that catalyze oxidative 5,6-spiroketalization of cholesterol to produce diosgenin, with evolutionary progenitors traced to conserved phytohormone metabolism. This study paves the way for engineering the production of diosgenin and derived analogs in heterologous hosts.

Date: 2019
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DOI: 10.1038/s41467-019-11286-7

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