Isolation and biosynthesis of daturamycins from Streptomyces sp. KIB-H1544

Yin Chen; Jinqiu Ren; Ruimin Yang; Jie Li; Sheng-Xiong Huang; Yijun Yan

doi:10.3762/bjoc.18.101

Isolation and biosynthesis of daturamycins from Streptomyces sp. KIB-H1544

Beilstein J Org Chem. 2022 Aug 9:18:1009-1016. doi: 10.3762/bjoc.18.101. eCollection 2022.

Authors

Yin Chen^#^{1

2}, Jinqiu Ren^#¹, Ruimin Yang¹, Jie Li^{1

2}, Sheng-Xiong Huang¹, Yijun Yan¹

Affiliations

¹ State Key Laboratory of Phytochemistry and Plant Resources in West China, and CAS Center for Excellence in Molecular Plant Sciences, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China.
² University of Chinese Academy of Sciences, Beijing 100049, China.

^# Contributed equally.

Abstract

Two novel diarylcyclopentenones daturamycin A and B (1 and 2), and one new p-terphenyl daturamycin C (3), along with three known congeners (4-6), were isolated from a rhizosphere soil-derived Streptomyces sp. KIB-H1544. The structures of new compounds were elucidated via a joint use of spectroscopic analyses and single-crystal X-ray diffractions. Compounds 1 and 2 belong to a rare class of tricyclic 6/5/6 diarylcyclopentenones, and compounds 3-6 possess a C-18 tricyclic aromatic skeleton. The biosynthetic gene cluster of daturamycins was identified through gene knockout and biochemical characterization experiments and the biosynthetic pathway of daturamycins was proposed.

Keywords: Streptomyces; biosynthesis; diarylcyclopentenone; p-terphenyl; polyporic acid synthetase.

Grants and funding

This research was financially supported by the National Natural Science Foundation of China (82073738, 31972852, and U1702285), the Yunnan Provincial Science and Technology Department (2019FJ007 and 2019FA034), Biological Resources Program (KFJ-BRP-009), and Research Program of Frontier Sciences (QYZDB-SSW-SMC051), Yunnan Thousand Talents Plan Young Talent and Youth Innovation Promotion Association (2018424), Chinese Academy of Sciences.