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. 2024 Aug 1;43(18):4092–4109. doi: 10.1038/s44318-024-00181-7

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© The Author(s) 2024

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 licence, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence 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 licence, visit http://creativecommons.org/licenses/by/4.0/. Creative Commons Public Domain Dedication waiver http://creativecommons.org/publicdomain/zero/1.0/ applies to the data associated with this article, unless otherwise stated in a credit line to the data, but does not extend to the graphical or creative elements of illustrations, charts, or figures. This waiver removes legal barriers to the re-use and mining of research data. According to standard scholarly practice, it is recommended to provide appropriate citation and attribution whenever technically possible.

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(A) Schematic representation of the three steps of the general phenylpropanoid pathway. PAL, phenylalanine ammonia-lyase; C4H, cinnamic acid 4-hydroxylase; 4CL, 4-coumarate:CoA ligase. (B) Search for AtCYP73A5 homologs in Viridiplantae by a reciprocal best hit (RBH) strategy. MRCA, most recent common ancestor. (C) Maximum-likelihood nucleotide tree (IQ-TREE2, GTR + F + I + R7) describing the phylogenetic relationships between 275 CYP73 homologous sequences. SH-aLRT test and ultrafast bootstrap (1000 pseudo-replicates) supports are annotated on main branches. CYP73 homologs relevant to the present study are indicated. At, Arabidopsis thaliana; Bd, Brachypodium distachyon; Mp, Marchantia polymorpha; Pc, Phaeoceros carolinianus. Scale bar represents the number of nucleotide substitutions per site. Tree was rooted according to the midpoint method. (D) Representative UHPLC-MS/MS chromatograms showing the production in vitro of p-coumaric acid from t-cinnamic acid (C4H activity) by recombinant CYP73 proteins representative of the three major bryophyte groups: mosses (PpCYP73A48), liverworts (MpCYP73A1) and hornworts (PcCYP73A). Assays performed with microsomes derived from yeasts transformed with an empty vector were used as negative controls. Source data are available online for this figure.