Genome Mining-Based Discovery of Two New Anthraquinone-γ-Pyrones from Streptomyces fragilis

doi:10.6023/cjoc202604008

Chinese Journal of Organic Chemistry

ARTICLE

基于基因组挖掘的脆弱链霉菌中两个新型蒽醌-γ-吡喃酮类化合物的发现

王云帆^a,b, 游松^*,a, 唐功利^*,b,c, 侯现锋^*,b

^a沈阳药科大学生命科学与生物制药学院沈阳 110016;
^b中国科学院上海有机化学研究所上海 200032;
^c国科大杭州高等研究院化学与材料科学学院杭州 310024

收稿日期:2026-05-11 修回日期:2026-06-24 发布日期:2026-09-14
基金资助:
国家自然科学基金(No. 22077134) 和中国科学院青年创新促进会(2019257)资助项目.

Genome Mining-Based Discovery of Two New Anthraquinone-γ-Pyrones from Streptomyces fragilis

Yunfan Wang^a,b, Song You^*,a, Gong-Li Tang^*,b,c, Xian-Feng Hou^*,b

^aSchool of Life Sciences and Biopharmaceuticals, Shenyang Pharmaceutical University, Shenyang 110016, P.R. China;
^bShanghai Institute of Organic Chemistry, Chinese Academy of Sciences (CAS), University of CAS, Shanghai 200032, China;
^cSchool of Chemistry and Material Sciences, Hangzhou Institute for Advanced Study, University of CAS, Hangzhou 310024, China

Received:2026-05-11 Revised:2026-06-24 Published:2026-09-14
Contact: *E-mail: yousong206@aliyun.com, gltang@sioc.ac.cn; houxf3411@163.com
Supported by:
National Natural Science Foundation of China (No. 22077134). and the CAS (Youth Innovation Promotion Association 2019257).

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Abstract

Two new anthraquinone-γ-pyrones, fragoquinones A-B (1-2), were discovered from Streptomyces fragilis by overexpression of SARP regulator gene ctg18_196, encoding a cluster-specific positive transcription activator. Their structures were elucidated by analysis of their HRESIMS and NMR spectroscopic data. Preliminary evaluation of antibacterial activity indicated that these two compounds displayed no significant antibacterial effects.

Key words: Genome mining, Streptomyces fragilis, Anthraquinone-γ-pyrones, Structural elucidation, SARP regulator gene

Cite this article

Yunfan Wang, Song You, Gong-Li Tang, Xian-Feng Hou. Genome Mining-Based Discovery of Two New Anthraquinone-γ-Pyrones from Streptomyces fragilis[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202604008.

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[1] Procópio R. E.; Silva I. R.; Martins M. K.; Azevedo J. L.; Araújo J. M.Braz. J. Infect. Dis. 2012, 16, 466-471.
[2] Ikeda H.; Ishikawa J.; Hanamoto A.; Shinose M.; Kikuchi H.; Shiba T.; Sakaki Y.; Hattori M.; Omura S. Nat. Biotechnol.2003, 21, 526-531.
[3] Bentley S. D.; Chater K. F.; Cerdeño-Tárraga A. M.; … Hopwood, D. A. Nature.2002, 417, 141-147.
[4] Bachmann B. O.;Van Lanen, S. G.; Baltz, R. H.J. Ind. Microbiol. Biotechnol. 2014, 41, 175-184.
[5] Nett M.; Ikeda H.; Moore, B. S. Nat. Prod. Rep.2009, 26, 1362-1384.
[6] Zerikly M.; Challis G. L. ChemBiochem.2009; 10, 625-633.
[7] Rutledge P. J.; Challis, G. L. Nat. Rev. Microbiol.2015, 13, 509-523.
[8] Laureti L.; Song L.; Huang S.; Corre C.; Leblond P.; Challis G. L.; Aigle, B. Proc. Natl. Acad. Sci. U. S. A.2011, 108, 6258-6263.
[9] Bibb M. J.Curr. Opin. Microbiol. 2005, 8, 208-215.
[10] Weber T.; Blin K.; Duddela S.; Krug D.; Kim H.U.; Bruccoleri R.; Lee S. Y.; Fischbach M. A.; Müller R.; Wohlleben W.; Breitling R.; Takano E.; Medema, M. H. Nucleic Acids Res.2015, 43, 237-243.
[11] Pan H. X.; Chen Z.; Zeng T.; Jin, W. B; Geng, Y.; Lin G. M.; Zhao J.; Li, W. T; Xiong, Z.; Huang, S. X; Zhai, X.; Liu H. W.; Tang, G. L. Org. Lett.2019, 21, 1374-1378.
[12] Ji Z. Y.; Nie Q. Y.; Yin Y.; Zhang M.; Pan H. X.; Hou X. F.; Tang, G. L. Angew. Chem. Int. Ed.2019, 58, 18046-18054.
[13] Van Cura D.; Ng T. L.; Huang J.; Hager, H. Angew. Chem. Int. Ed.2023, 62, e202304646.
[14] Shikai Y.; Kawai S. Chem. Sci.2023, 14, 8766-8776.
[15] Dong L.; Shen Y.; Hou X. F.; Li W. J.; Tang, G. L. Org. Lett.2019, 21, 2322-2325.
[16] Hou X. F.; Song Y. J.; Zhang M.; Lan W.; Meng S.; Wang C.; Pan H. X.; Cao C.; Tang, G. L. Angew. Chem. Int. Ed.2018, 57, 13475-13479.
[17] Guo W.; Xiao Z.; Huang T.; Zhang K.; Pan H. X.; Tang G. L.; Deng Z.; Liang R.; Lin, S. Microb. Cell Fact.2023, 22, 127.
[18] Murphy B. T.; Narender T.; Kauffman C. A.; Woolery M.; Jensen P. R.; Fenical, W. Aust. J. Chem.2010, 63, 10.1071/CH10068.
[19] Zhou L.; Chen X. Mar. Drugs.2021, 19, 575.
[20] Zhang F.; Roberts C. D.; Lee T. H.; Braun D. R.; Bennett, Z. D. J. Nat. Prod.2025, 88, 2325-2332.
[21] Tietze L.F.; Singidi R.R.; Gericke, K M. Org. Lett.2006, 8, 5873-5876.

基于基因组挖掘的脆弱链霉菌中两个新型蒽醌-γ-吡喃酮类化合物的发现

Genome Mining-Based Discovery of Two New Anthraquinone-γ-Pyrones from Streptomyces fragilis

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