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. 2022 Aug 25;13:5011. doi: 10.1038/s41467-022-32667-5

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© The Author(s) 2022

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

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Fig. 1 — a Hypothesized scheme for the rearrangement of methyl groups on the A-ring of labdane type diterpenoids and examples of diterpenoids with the 18(4→3) abeo-abietane core structure. Examples of labdane type diterpenoids from the Lamiaceae species Coleus forskohlii and the Celastracae species T. wilfordii with an abeo-abietane core structure are shown. The rings of the tricyclic core structure are denoted A, B, and C. b Maximum-likelihood phylogenetic analysis of selected CYP genes from the 71 clan, including plant CYPs from the CYP82 and CYP71 subfamily, and NtCYP51 as the root. Shown CYPs are involved in either phenylpropanoid (purple) or terpenoid (grey) biosynthesis (Supplementary Table 22, Supplementary Fig. 1). TwCYP genes functionally characterized in this work highlighted in bold. Nodes marked * are supported by bootstrap values >85%. c Schematic overview of the genome location of the Tw genes used for heterologous biosynthesis of triptonide in the T. wilfordii genome⁶. Genes marked with * are found as tandem repeats with each copy having on average nucleotide sequence identity of 88.7% to the cDNA sequence of each of the genes used in this paper (Supplementary Table 23). TwCYP71BE84 and TwCYP71BE86 homologs are each found in tandem repeats in two different loci of the T. wilfordii genome.