- Parallel evolution of UbiA superfamily proteins into aromatic O-prenyltransferases in plants
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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 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.
- 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
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- Natural oxyprenylated coumarins are modulators of melanogenesis
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Naturally occurring coumarins 7-isopentenyloxycoumarin, auraptene, and umbelliprenin are able to modulate the biosynthesis of melanin in murine Melan-a cells probably through the interaction with selected biological targets like estrogen receptor β and aryl hydrocarbon receptor. Such a modulation strictly depends on the individual structure of the coumarin: the presence of a 3,3-dimethylallyloxy side chain is a structural determinant for tanning activation whereas a farnesyl one leads to the opposite effect. The parent compound with a free OH group, umbelliferone, did not provide any interaction. Other coumarins assayed, having shorter chains and/or being substituted in other positions, and prenyloxypsoralens, were not active or not further investigated in this context being cytotoxic at low doses.
- Fiorito, Serena,Epifano, Francesco,Preziuso, Francesca,Cacciatore, Ivana,di Stefano, Antonio,Taddeo, Vito Alessandro,de Medina, Philippe,Genovese, Salvatore
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p. 274 - 282
(2018/05/14)
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- Design, synthesis and evaluation of furanocoumarin monomers as inhibitors of CYP3A4
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A number of furanocoumarins isolated from grapefruit juice have been found to inhibit CYP3A4 activity in vitro. In this study, we have designed and synthesised a range of analogues based on bergamottin to investigate the relationship between chemical stru
- Row,Brown,Stachulski,Lennard
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p. 1604 - 1610
(2008/02/03)
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