2. Academic Validation
  3. Discovery, Structure Correction, and Biosynthesis of Actinopyrones, Cytotoxic Polyketides from the Deep-Sea Hydrothermal-Vent-Derived Streptomyces sp. SCSIO ZS0520

Discovery, Structure Correction, and Biosynthesis of Actinopyrones, Cytotoxic Polyketides from the Deep-Sea Hydrothermal-Vent-Derived Streptomyces sp. SCSIO ZS0520

  • J Nat Prod. 2022 Mar 25;85(3):625-633. doi: 10.1021/acs.jnatprod.1c00901.
Huaran Zhang 1 2 3,  Xuejia Zhang 1,  Yun Huang 4,  Jie Yuan 5,  Xiaoyi Wei 6,  Jianhua Ju 1 2 3
Affiliations

Affiliations

  • 1 CAS Key Laboratory of Tropical Marine Bio-Resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, China.
  • 2 College of Oceanology, University of Chinese Academy of Sciences, Qingdao 266400, China.
  • 3 Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), No. 1119, Haibin Road, Nansha District, Guangzhou 511458, China.
  • 4 School of Basic Medical Sciences, Southern Medical University, Guangzhou 510515, China.
  • 5 Key Laboratory of Tropical Disease Control, Zhongshan School of Medicine, Sun Yat-sen University, Guangzhou 510080, China.
  • 6 Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, China.
PMID: 34852194 DOI: 10.1021/acs.jnatprod.1c00901
Abstract

Three new actinopyrone derivatives, actinopyrones E-G (1, 3, and 4), together with three known analogues, PM050463 (2), actinopyrone D (5), and PM050511 (6), were isolated from Streptomyces sp. SCSIO ZS0520 derived from a deep-sea hydrothermal vent. Their structures, complete with absolute configurations, were elucidated using extensive spectroscopic analyses combined with Mosher's method, ECD calculations, and bioinformatics analyses. These findings corrected the absolute configurations of previously reported actinopyrone analogues 2, 5, and 6 at C-3, C-9, and C-10. Notably, compound 6 displayed notable cytotoxicity against six human cell lines with IC50 values of 0.26-2.22 μM. A likely biosynthetic pathway and annotations of protein function are proposed on the basis of bioinformatics analyses. Genes coding for methyltransferase and Glycosyltransferase tailoring chemistries needed to generate final structures were notably absent from the biosynthetic gene cluster. Taken together, these results enable further bioengineering of the actinopyrones and related congeners as potential antitumor agents.

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