Full biosynthetic pathway of pyrrolobenzoxazines  

作　　者：Kunya Wang Bingyu Liu Daojiang Yan Jian Bai Haibo Yu Youcai Hu 

机构地区：[1]State Key Laboratory of Bioactive Substance and Function of Natural Medicines,Institute of Materia Medica,Chinese Academy of Medical Sciences&Peking Union Medical College,Beijing 100050,China

出　　处：《Chinese Chemical Letters》2025年第1期433-436,共4页中国化学快报(英文版)

基　　金：supported financially by the National Natural Science Foundation of China(Nos.22107122 and 82225042);the CAMS Innovation Fund for Medical Sciences(CIFMS,No.2021I2M-1-029)。

摘　　要：Pyrrolobenzoxazines are a rare terpene-amino acid family of natural products with potent biological activities.Here,we reported the full biosynthetic pathway of paeciloxazine(1),a typical pyrrolobenzoxazine,with significant insecticidal activity.Base on heterologous expression,chemical complement experiment,and in vitro biochemical assays,we demonstrated the sesquiterpene portion of 1 derived from discontinuously oxidations of amorphdiene,in which P450 monooxygenase PaxH catalyzed a cascade of hydroxylation and epoxidation,while two flavin dependent monooxygenases are involved in the transformation of the esterified tryptophan into a pyrrolobenzoxazine core.Furthermore,a total of 15 compounds were generated through heterologous expression,of which 13,17 and 20 showed potential antiepileptic activity.This study fully elucidated the biosynthetic pathway of paeciloxazine(1)and showed the diversity and complexity of constructing natural products by organisms.

关 键 词：Pyrrolobenzoxazines Paeciloxazine BIOSYNTHESIS P450 monooxygenase Antiepileptic activity 

分 类 号：O62[理学—有机化学]