Parallel evolution of UbiA superfamily proteins into aromatic -prenyltransferases in plants.

Ryosuke Munakata, Alexandre Olry, Tomoya Takemura, Kanade Tatsumi, Takuji Ichino, Cloé Villard, Joji Kageyama, Tetsuya Kurata, Masaru Nakayasu, Florence Jacob, Takao Koeduka, Hirobumi Yamamoto, Eiko Moriyoshi, Tetsuya Matsukawa, Jérémy Grosjean, Célia Krieger, Akifumi Sugiyama, Masaharu Mizutani, Frédéric Bourgaud, Alain Hehn, Kazufumi Yazaki

Journal: Proceedings of the National Academy of Sciences of the United States of America 2021;118(17):e2022294118

PMID: 33883279

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Abstract

Plants produce ∼300 aromatic compounds enzymatically linked to prenyl side chains via C-O bonds. These -prenylated aromatic compounds have been found in taxonomically distant plant taxa, with some of them being beneficial or detrimental to human health. Although their -prenyl moieties often play crucial roles in the biological activities of these compounds, no plant gene encoding an aromatic -prenyltransferase (-PT) has been isolated to date. This study describes the isolation of an aromatic -PT gene, , belonging to the UbiA superfamily, from grapefruit ( × Rutaceae). This gene was shown responsible for the biosynthesis of -prenylated coumarin derivatives that alter drug pharmacokinetics in the human body. Another coumarin -PT gene encoding a protein of the same family was identified in , an apiaceous medicinal plant containing pharmaceutically active -prenylated coumarins. Phylogenetic analysis of these -PTs suggested that aromatic -prenylation activity evolved independently from the same ancestral gene in these distant plant taxa. These findings shed light on understanding the evolution of plant secondary (specialized) metabolites via the UbiA superfamily.

Address: Laboratory of Plant Gene Expression, Research Institute for Sustainable Humanosphere, Kyoto University, Uji 611-0011, Japan.; Laboratoire Agronomie et Environnement, Université de Lorraine-National Institute for Agronomic and Environmental Research, F54000, Nancy, France.; Laboratoire Agronomie et Environnement, Université de Lorraine-National Institute for Agronomic and Environmental Research, F54000, Nancy, France.; Laboratory of Plant Gene Expression, Research Institute for Sustainable Humanosphere, Kyoto University, Uji 611-0011, Japan.; EditForce Inc., Fukuoka 810-0001, Japan.; PalmElit SAS, 34980 Montferrier sur Lez, France.; Graduate School of Sciences and Technology for Innovation, Yamaguchi University, Yamaguchi 753-8515, Japan.; Department of Applied Biosciences, Faculty of Life Sciences, Toyo University, Itakura 374-0193, Japan.; The Experimental Farm, Kindai University, Wakayama 643-0004, Japan.; Faculty of Biology-Oriented Science and Technology, Kindai University, Wakayama 649-6493, Japan.; Functional Phytochemistry, Graduate School of Agricultural Science, Kobe University, Kobe 657-8501, Japan.; Plant Advanced Technologies, 54500 Vandoeuvre, France.; Laboratoire Agronomie et Environnement, Université de Lorraine-National Institute for Agronomic and Environmental Research, F54000, Nancy, France; [email protected] [email protected].; Laboratory of Plant Gene Expression, Research Institute for Sustainable Humanosphere, Kyoto University, Uji 611-0011, Japan; [email protected] [email protected].

DOI: 10.1073/pnas.2022294118

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MeSH Terms: Angelica, Citrus paradisi, Evolution, Molecular, Furocoumarins, Phylogeny, Plant Proteins, Prenylation