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

• Published in: Proceedings of the National Academy of Sciences - PNAS Vol. 118; no. 17; pp. 1 - 9
• Main Authors: Munakata, Ryosuke, Olry, Alexandre, Takemura, Tomoya, Tatsumi, Kanade, Ichino, Takuji, Villard, Cloé, Kageyama, Joji, Kurata, Tetsuya, Nakayasu, Masaru, Jacob, Florence, Koeduka, Takao, Yamamoto, Hirobumi, Moriyoshi, Eiko, Matsukawa, Tetsuya, Grosjean, Jérémy, Krieger, Célia, Sugiyama, Akifumi, Mizutani, Masaharu, Bourgaud, Frédéric, Hehn, Alain, Yazaki, Kazufumi
• Format: Journal Article
• Language: English
• Published: United States National Academy of Sciences 27.04.2021
• Subjects: Aromatic compounds; Biological Sciences; Biosynthesis; Chemical bonds; Citrus paradisi; Coumarin; Evolution; Flowers & plants; Grapefruit; Herbal medicine; Life Sciences; Medicinal plants; Metabolites; Pharmacokinetics; Phylogeny; Prenyltransferases; Proteins; Taxa; parallel evolution; grapefruit–drug interactions; aromatic O-prenyltransferase; coumarin; plant-specialized metabolism
• ISSN: 0027-8424; 1091-6490
• DOI: 10.1073/pnas.2022294118

Plants produce ∼300 aromatic compounds enzymatically linked to prenyl side chains via C–O bonds. These O-prenylated aromatic compounds have been found in taxonomically distant plant taxa, with some of them being beneficial or detrimental to human health. Although their O-prenyl moieties often play crucial roles in the biological activities of these compounds, no plant gene encoding an aromatic O-prenyltransferase (O-PT) has been isolated to date. This study describes the isolation of an aromatic O-PT gene, CpPT1, belonging to the UbiA superfamily, from grapefruit (Citrus × paradisi, Rutaceae). This gene was shown responsible for the biosynthesis of O-prenylated coumarin derivatives that alter drug pharmacokinetics in the human body. Another coumarin O-PT gene encoding a protein of the same family was identified in Angelica keiskei, an apiaceous medicinal plant containing pharmaceutically active O-prenylated coumarins. Phylogenetic analysis of these O-PTs suggested that aromatic O-prenylation activity evolved independently fromthe 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.