| Title: | A promiscuous fatty acid omega-hydroxylase CYP94A90 is likely to be involved in biosynthesis of a floral nitro compound in loquat (Eriobotrya japonica) |
| Author(s): | Yamaguchi T; Matsui Y; Kitaoka N; Kuwahara Y; Asano Y; Matsuura H; Sunohara Y; Matsumoto H; |
| Address: | "Faculty of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki, 305-8572, Japan. Biotechnology Research Center, Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama, 939-0398, Japan. College of Biological Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki, 305-8572, Japan. Research Faculty of Agriculture, Hokkaido University, Kita-9 Nishi-9, Sapporo, Hokkaido, 060-8589, Japan" |
| ISSN/ISBN: | 1469-8137 (Electronic) 0028-646X (Linking) |
| Abstract: | "Nitro groups are often associated with synthetically manufactured compounds such as medicines and explosives, and rarely with natural products. Loquat emits a nitro compound, (2-nitroethyl)benzene, as a flower scent. The nitro compound exhibits fungistatic activity and is biosynthesised from l-phenylalanine via (E/Z)-phenylacetaldoxime. Although aldoxime-producing CYP79s have been intensively studied, it is unclear what enzymes form nitro groups from aldoximes either in plants or in other organisms. Here, we report the identification of two cytochrome P450s that are likely to be involved in (2-nitroethyl)benzene biosynthesis in loquat through differential gene expression analysis using RNA-seq and functional identification using yeast and tobacco. CYP79D80 and CYP94A90 catalysed the formation of (E/Z)-phenylacetaldoxime from l-phenylalanine and (2-nitroethyl)benzene from the aldoxime, respectively. Expression profiles of CYP79D80 and CYP94A90 were correlated with the emission of (2-nitroethyl)benzene from loquat flowers. CYP94A90 also functioned as a fatty acid omega-hydroxylase as do other CYP94A fatty acid omega-hydroxylases. The CYP94As tested from other plants were all found to catalyse the formation of (2-nitroethyl)benzene from (E/Z)-phenylacetaldoxime. CYP79D80 and CYP94A90 are likely to operate in concert to biosynthesise (2-nitroethyl)benzene in loquat. CYP94A90 and other CYP94As are 'promiscuous fatty acid omega-hydroxylases', catalysing the formation of nitro groups from aldoximes, and are widely distributed in dicot plants" |
| Keywords: | Cytochrome P-450 CYP4A *Eriobotrya Flowers Nitro Compounds Odorants cytochrome P450 enzyme promiscuity fatty acid omega-hydroxylase flower scent loquat nitro compound plant specialised metabolite; |
| Notes: | "MedlineYamaguchi, Takuya Matsui, Yumi Kitaoka, Naoki Kuwahara, Yasumasa Asano, Yasuhisa Matsuura, Hideyuki Sunohara, Yukari Matsumoto, Hiroshi eng Research Support, Non-U.S. Gov't England 2021/05/02 New Phytol. 2021 Aug; 231(3):1157-1170. doi: 10.1111/nph.17441. Epub 2021 May 31" |
