Two CYP71AJ enzymes function as psoralen synthase and angelicin synthase in the biosynthesis of furanocoumarins in Peuce
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Two CYP71AJ enzymes function as psoralen synthase and angelicin synthase in the biosynthesis of furanocoumarins in Peucedanum praeruptorum Dunn Xiangyun Jian1 · Yucheng Zhao1 · Ziwen Wang1 · Shan Li1 · Li Li1 · Jun Luo1 · Lingyi Kong1 Received: 19 January 2020 / Accepted: 31 July 2020 © Springer Nature B.V. 2020
Abstract Key Message Psoralen synthase and angelicin synthase responsible for the formation of psoralen and angelicin in Peucedanum praeruptorum Dunn were identified and functionally characterized, respectively. Abstract Furanocoumarins were reported to possess several activities such as anticancer, anti-inflammatory and neuroprotective, and function as phytotoxin and allelochemical in plants. Furanocoumarins are the main bioactive ingredient in P. praeruptorum which is a commonly used traditional Chinese medicine. Phenylalanine ammonia lyase (PAL), 4-coumarate: CoA ligase (4CL), p-coumaroyl CoA 2’-hyfroxylase (C2’H) were cloned previously to elucidate the biosynthetic mechanism of coumarin lactone ring. However, the genes involved in complex coumarins in P. praeruptorum have not been explored. Herein, putative psoralen synthase CYP71AJ49 and angelicin synthase CYP71AJ51 were cloned from P. praeruptorum. In vivo and in vitro yeast assays were conducted to confirm their activities. Furthermore, the results of High Performance Liquid Chromatography–Electrospray Ionization Mass Spectrometry (HPLC–ESI–MS) verified that CYP71AJ49 catalyzed the conversion of marmesin to psoralen, and CYP71AJ51 catalyzed columbianetin to angelicin. Subsequently, the expression profile showed that CYP71AJ49 and CYP71AJ51 were easily affected by environmental conditions, especially UV and temperature. The genes tissue-specific expression and compounds tissue-specific distribution pattern indicated the existence of substance transport in P. praeruptorum. Phylogenetic analysis was conducted with 27 CYP71AJs, CYP71AJ49 and CYP71AJ51 were classified in I-4 and I-2, respectively. These results provide further insight to understand the biosynthetic mechanism of complex coumarins. Keywords Psoralen synthase · Angelicin synthase · Peucedanum praeruptorum · Furanocoumarin biosynthesis · Functional characterization
Introduction
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11103-020-01045-4) contains supplementary material, which is available to authorized users. Xiangyun Jian and Yucheng Zhao contributed equally to this work. * Lingyi Kong [email protected] 1
Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, School of Traditional Chinese Pharmacy, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, People’s Republic of China
Furanocoumarins and its derivatives are important secondary metabolites in plants, and have been reported to have many pharmacological activities, such as antioxidant, antibacterial, antifungal, antiviral and anticancer (Hung et al. 2017; Piao et al. 2004; Raju et al. 2018; Yang et a
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