A promiscuous fatty acid ω‐hydroxylase CYP94A90 is likely involved in biosynthesis of a floral nitro compound in loquat (Eriobotrya japonica)
A promiscuous fatty acid ω‐hydroxylase CYP94A90 is likely involved in biosynthesis of a floral nitro compound in loquat (Eriobotrya japonica)
复制标题
一种混杂脂肪酸 ω-羟化酶 CYP94A90 可能参与枇杷 (Eriobotrya japonica) 中花硝基化合物的生物合成
DOI：
10.1111/nph.17441
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发表时间：
2022
期刊：
影响因子：
9.4
通讯作者：
Matsumoto Hiroshi
中科院分区：
文献类型：
--
作者：
Yamaguchi Takuya;Matsui Yumi;Kitaoka Naoki;Kuwahara Yasumasa;Asano Yasuhisa;Matsuura Hideyuki;Sunohara Yukari;Matsumoto Hiroshi
硝基基团通常与合成制造的化合物如药物和炸药有关，很少与天然产品有关。枇杷发出一种硝基化合物，（2-硝基乙基）苯，作为花香。该硝基化合物具有抑真菌活性，并通过（E/Z）-苯乙醛肟由l-苯丙氨酸生物合成。虽然产生醛肟的CYP 79已经被深入研究，但还不清楚是什么酶在植物或其他生物体中从醛肟形成硝基。我们报告了两种细胞色素P450的鉴定，它们可能参与了（2-硝基乙基）通过使用RNA测序的差异基因表达分析和使用酵母和烟草的功能鉴定，研究枇杷中的苯生物合成。CYP 79 D80和CYP 94 A90分别催化苯丙氨酸和2-硝基乙基苯生成（E/Z）-苯乙醛肟。CYP 79 D80和CYP 94 A90的表达谱与枇杷花中2-硝基乙基苯的释放相关。CYP 94 A90也像其他CYP 94 A脂肪酸ω-羟化酶一样作为脂肪酸ω-羟化酶发挥作用。其他植物的CYP 94 As均能催化（E/Z）-苯乙醛肟生成（2-硝基乙基）苯，而CYP 79 D80和CYP 94 A90可能协同作用，共同催化枇杷中的（2-硝基乙基）苯的生物合成。CYP 94 A90和其他CYP 94 A是“混杂脂肪酸ω-羟化酶”，催化醛肟形成硝基，广泛分布于双子叶植物中。
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 froml‐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 froml‐phenylalanine and (2‐nitroethyl)benzene from the aldoxime, respectively. Expression profiles ofCYP79D80andCYP94A90were correlated with the emission of (2‐nitroethyl)benzene from loquat flowers. CYP94A90 also functioned as a fatty acid ω‐hydroxylase as do other CYP94A fatty acid ω‐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 ω‐hydroxylases’, catalysing the formation of nitro groups from aldoximes, and are widely distributed in dicot plants.