(±)-Feionemycin A and Chromonemycins A–D, Rearranged Aromatic Polyketides Uncovered by Type II Polyketide Gene Cluster Expression
Two novel spiro aromatic polyketides, (+)- and (-)-feionemycin A (<b>1</b>), along with four atypical angucyclinones named as chromonemycins A-D (<b>2</b>-<b>5</b>), were discovered through heterologous expression of a type II polyketide gene cluster, within which one previously characterized flavoprotein monooxygenase was deactivated. Among those structures, compound <b>1</b> features an unprecedented oxaspiro[5.4]undecane architecture, and compounds <b>2</b>-<b>5</b> represent novel atypical angucyclinone variants derived from unusual cyclization of the polyketide chains. The structures and absolute configurations were elucidated by NMR, MS, single-crystal X-ray diffraction, theoretical NMR calculations, DP4+ probability analysis, and ECD analyses. (+)-<b>1</b> showed cytotoxic activity against NCI-H446, with an IC<sub>50</sub> value of 2.26 μM.
Authors
- Qian Che (ORCID: https://orcid.org/0000-0003-0610-1593)
- Tianjiao Zhu (ORCID: https://orcid.org/0000-0003-4185-5593)
- Guojian Zhang (ORCID: https://orcid.org/0000-0002-4976-8083)
- Dehai Li (ORCID: https://orcid.org/0000-0002-7191-2002)
- Chuanteng Ma (ORCID: https://orcid.org/0000-0002-0262-8825)
- Xiaofei Huang
- Jiayi Li (ORCID: https://orcid.org/0000-0002-7770-7376)
- Xiao Xu (ORCID: https://orcid.org/0009-0003-5547-1686)
- Luning Zhou (ORCID: https://orcid.org/0000-0001-5283-4769)
- Wenxue Wang (ORCID: https://orcid.org/0000-0002-9137-8302)
Institutions
- Qingdao National Laboratory for Marine Science and Technology (CN)
- Zubov State Oceanographic Institute (RU)
- Marine Biomedical Research Institute of Qingdao (CN)
- Ocean University of China (CN)
Publication Details
- Journal
- Journal of Natural Products
- Published
- 2025-02-28
- DOI
- https://doi.org/10.1021/acs.jnatprod.4c01433
- Citations
- 1
- Primary Topic
- Microbial Natural Products and Biosynthesis
- Type
- article
- Field-Weighted Citation Impact
- 1.39
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Shandong Province
- Taishan Scholar Project of Shandong Province
- National Natural Science Foundation of China-Shandong Joint Fund
- National Key Research and Development Program of China
- Fundamental Research Funds for the Central Universities