[reaction: see text] A general method for the synthesis of benz[a]anthraquinones is reported. The key step is a catalytic cobalt-mediated [2+2+2]-cycloaddition of a triyne, which affords an angularly substituted tetracycle. Oxidation of this core gives the typical structure of angucyclinone antibiotics.
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Mar Drugs
January 2025
School of Biological Science and Technology, University of Jinan, 336 West Road of Nan Xinzhuang, Jinan 250022, China.
Angucyclines/angucyclinones, a class of polyketides with diverse chemical structures, display various bioactivities including antibacterial or antifungal, anticancer, anti-neuroinflammatory, and anti-α-glucosidase activities. Marine and terrestrial microorganisms have made significant contributions to the discovery of bioactive angucyclines/angucyclinones. This review covers 283 bioactive angucyclines/angucyclinones discovered from 1965 to 2023, and the emphasis is on the biological origins, chemical structures, and biological activities of these interesting natural products.
View Article and Find Full Text PDFEur J Med Chem
February 2025
The Affiliated Hospital of Qingdao University, Qingdao University, Qingdao, 266000, China; Institute of Regenerative Medicine and Laboratory Technology Innovation, Qingdao University, Qingdao, Shandong, 266071, China. Electronic address:
Actinomycete bacteria derived from marine environments are a good source of natural products with diverse biological activities such as cytotoxicity, antiviral, and antimicrobial actions. This review summarizes 191 angucyclines and angucyclinones derived from marine actinomycetes reported in the literature from 2014 to 2023 and introduced the latest developments in actinomycete-silenced biosynthetic gene cluster activation, including heterologous recombination and in situ activation. The key role of redox post-modifications in the biosynthetic process of atypical angucyclines.
View Article and Find Full Text PDFMar Drugs
October 2024
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China.
Heterologous expression has emerged as an effective strategy in activating cryptic gene clusters or improving yield. Eight compounds were successfully obtained by heterologous expression of the type II PKS gene cluster derived from marine sp. HDN155000 in the chassis host J1074.
View Article and Find Full Text PDFOrg Lett
September 2024
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, Shandong 266003, People's Republic of China.
Six new angucycline structures, including spirocyclione A (), which contains an unusual oxaspiro[5.5]undecane architecture, and its ring-A-cleaved product spirocyclione B (), were discovered by heterologous expression of a type II polyketide biosynthetic gene cluster captured from a marine actinomycete strain sp. HDN155000.
View Article and Find Full Text PDFMicrob Cell Fact
July 2024
State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, China.
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