Identification of two multifunctional P450 enzymes for biosynthesis of sesteraltererol-type sesterterpenoids

Yue Liu; Zhuo-Jia Gan; Zhong-Yuan Zhang; Huan Zhao; Shao-Yang Li; Gao-Qian Wang; Guo-Dong Chen; Takayoshi Awakawa; Zhi-Qin Cao; Jian-Ming Lv; Dan Hu; Hao Gao

doi:10.1039/D6OB00650G

Identification of two multifunctional P450 enzymes for biosynthesis of sesteraltererol-type sesterterpenoids

Yue Liu,†^a Zhuo-Jia Gan,†^a Zhong-Yuan Zhang,†^a Huan Zhao,^c Shao-Yang Li,^a Gao-Qian Wang,^a Guo-Dong Chen,

^a Takayoshi Awakawa,

^d Zhi-Qin Cao,*^b Jian-Ming Lv,

*^a Dan Hu

*^a and Hao Gao

^a

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* Corresponding authors

^a Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy/State Key Laboratory of Bioactive Molecules and Druggability Assessment/International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Ministry of Education (MOE) of China/Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, China
E-mail: thudan@jnu.edu.cn, ljm21@jnu.edu.cn

^b Guangdong Provincial Key Laboratory of Natural Drugs Research and Development, The Affiliated Dongguan Songshan Lake Central Hospital, School of Pharmacy, Guangdong Medical University, Dongguan 523808, China
E-mail: tcaozq@gdmu.edu.cn

^c College of Traditional Chinese Medicine, Jinan University, Guangzhou 510632, China

^d RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan

Abstract

A five-gene cluster for biosynthesis of sesteraltererol-type sesterterpenoids was identified. Among them, the sesterterpene synthase AasA catalyzed the formation of sesteraltererol, similar to the known terpene synthase AaTPS1, and then two multifunctional P450 enzymes AasE and AasB sequentially mediated oxidation. Heterologous expression produced seven new compounds, two of which exhibited antifungal activity.

Organic & Biomolecular Chemistry

Identification of two multifunctional P450 enzymes for biosynthesis of sesteraltererol-type sesterterpenoids

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Identification of two multifunctional P450 enzymes for biosynthesis of sesteraltererol-type sesterterpenoids

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