香豆素,来源于苯丙素途径,代表被子植物中的主要代谢产物之一。四氢吡喃(THP)和四氢呋喃(THF)环与内酯结构的对齐导致形成至少四种类型的复合香豆素。然而,香豆素结构多样性的潜在机制仍然知之甚少。这里,我们报道了伤翅目的染色体水平基因组组装,跨越1.64Gb,重叠群N50值为22.7Mb,60,021个注释的蛋白质编码基因。此外,我们确定了决定香豆素结构多样性的关键酶,包括两种对简单香豆素基本骨架结构至关重要的对香豆素酰CoA2'-羟化酶,两个UbiA异戊二烯转移酶负责角或线性香豆素生物合成,和参与THP和THF环形成的五种CYP736环化酶。值得注意的是,首次鉴定出两种能够同时催化去甲基的木脂素和烯醇的双功能酶。进化分析意味着CYP736亚家族的串联和异位重复,特别产生于伞形科,促成了丁香香豆素的结构多样性。最后,本研究为不同被子植物之间复杂的香豆素生物合成途径提出了一个平行的进化情景,并为香豆素的异源工业生产提供了必要的合成生物学要素。
Coumarins, derived from the phenylpropanoid pathway, represent one of the primary metabolites found in angiosperms. The alignment of the tetrahydropyran (THP) and tetrahydrofuran (THF) rings with the lactone structure results in the formation of at least four types of complex coumarins. However, the mechanisms underlying the structural diversity of coumarin remain poorly understood. Here, we report the chromosome-level genome assembly of Notopterygium incisum, spanning 1.64 Gb, with a contig N50 value of 22.7 Mb and 60,021 annotated protein-coding genes. Additionally, we identified the key enzymes responsible for shaping the structural diversity of coumarins, including two p-coumaroyl CoA 2\'-hydroxylases crucial for simple coumarins basic skeleton architecture, two UbiA prenyltransferases responsible for angular or linear coumarins biosynthesis, and five CYP736 cyclases involved in THP and THF ring formation. Notably, two bifunctional enzymes capable of catalyzing both demethylsuberosin and osthenol were identified for the first time. Evolutionary analysis implies that tandem and ectopic duplications of the CYP736 subfamily, specifically arising in the Apiaceae, contributed to the structural diversity of coumarins in N. incisum. Conclusively, this study proposes a parallel evolution scenario for the complex coumarin biosynthetic pathway among different angiosperms and provides essential synthetic biology elements for the heterologous industrial production of coumarins.