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1,4,6-trihydroxy-8-alkylated-9,10-anthraquinones with antibacterial activities from soil-derived Streptomyces sp. WS-13394

The Journal of Antibiotics volume 75, pages 375–379 (2022)Cite this article

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Abstract

Two new 1,4,6-trihydroxy-8-alkylated-9,10-anthraquinones (1–2) were isolated from the culture broth of the soil actinomycete Streptomyces sp. WS-13394. Their structures were elucidated on the basis of extensive spectroscopic analysis, including mass spectrometry (MS), nuclear magnetic resonance (NMR), and electronic circular dichroism (ECD). Compounds 1 and 2, together with eight analogs (3–10), were evaluated for their antibacterial activities against five pathogens. The tested derivatives of alkylated anthraquinone exhibited selective activities to Gram-positive bacteria, while compounds 1 and 5 showed obvious activities against two zoonotic pathogens, Erysipelothrix rhusiopathiae and Streptococcus suis, with MIC values ranging from 3.13 to 12.5 µg ml−1.

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References

  1. Semwal RB, Semwal DK, Combrinck S, Viljoen A. Emodin—a natural anthraquinone derivative with diverse pharmacological activities. Phytochemistry. 2021;190:112854.

    Article  CAS  Google Scholar 

  2. Singh J, Hussain Y, Luqman S, Meena A. Purpurin: a natural anthraquinone with multifaceted pharmacological activities. Phytother Res. 2020;35:2418–28.

    Article  Google Scholar 

  3. Prateeksha, Yusuf MA, Singh BN, Sudheer S, Kharwar RN, Siddiqui S, et al. Chrysophanol: a natural anthraquinone with multifaceted biotherapeutic potential. Biomolecules. 2019;9:68.

    Article  CAS  Google Scholar 

  4. Lu H, Wang CC, Lu WJ, Li XD, Wu ZY, Wang GY, et al. Apigenin and ampicillin as combined strategy to treat severe Streptococcus suis infection. Molecules. 2021;26:1980.

    Article  CAS  Google Scholar 

  5. Brooke CJ, Riley TV. Erysipelothrix rhusiopathiae: bacteriology, epidemiology and clinical manifestations of an occupational pathogen. J Med Microbiol. 1999;48:789–99.

    Article  Google Scholar 

  6. Wu ZY, Zhang YN, Fang W, Shi LQ, Wan ZY. Four new anthraquinone analogues from a soil actinomycete Streptomyces sp. WS-13394 and their bioactivities. Nat Prod Res. 2018;32:412–7.

    Article  CAS  Google Scholar 

  7. Wu ZY, Fang W, Shi LQ, Wan ZY, Min Y, Wang KM. New cytotoxic alkylated anthraquinone analogues from a soil actinomycete Streptomyces sp. WS-13394. Chem Pharm Bull. 2014;62:118–21.

    Article  CAS  Google Scholar 

  8. Luo XW, Lin XP, Tao HM, Wang JF, Li JF, Yang B, et al. Isochromophilones A-F, cytotoxic chloroazaphilones from the marine mangrove endophytic fungus Diaporthe sp. SCSIO 41011. J Nat Prod. 2018;81:934–41.

    Article  CAS  Google Scholar 

  9. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al. Gaussian 09, Revision D.01. Wallingford, CT: Gaussian Inc; 2013.

    Google Scholar 

  10. Liang Z, Gu TW, Wang JJ, She JL, Ye YX, Cao YX, et al. Chromene and chromone derivatives as liver X receptors modulators from a marine-derived Pestalotiopsis neglecta fungus. Bioorg Chem. 2021;112:104927.

    Article  CAS  Google Scholar 

  11. Wi YM, Greenwood-Quaintance KE, Schuetz AN, Ko KS, Peck KR, Song JH, et al. Activity of ceftolozane-tazobactam against carbapenem-resistant, non-carbapenemase-producing Pseudomonas aeruginosa and associated resistance mechanisms. Antimicrob Agents Chemother. 2017;62:e01970–17.

    PubMed  PubMed Central  Google Scholar 

  12. Lu H, Lu WJ, Zhu YW, Wang CC, Shi LM, Li XD, et al. Auranofin has advantages over first-line drugs in the treatment of severe Streptococcus suis infections. Antibiotics. 2020;10:26.

    Article  Google Scholar 

Download references

Acknowledgements

This research was financially supported by Natural Science Foundation of Hubei Province, China (2021CFB070) and Hubei Agricultural Science and Technology Innovation Center (2019-620-000-001-027).

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  1. These authors contributed equally: Zhaoyuan Wu, Manli Liu

Authors and Affiliations

  1. Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, No. 8, Nanhu Ave., Hongshan District, Wuhan, 430064, China

    Zhaoyuan Wu, Manli Liu, Kui Li, Fang Liu, Fei Zhang, Yani Zhang, Kaimei Wang & Wei Fang

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  1. Zhaoyuan Wu
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Correspondence to Wei Fang.

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Wu, Z., Liu, M., Li, K. et al. 1,4,6-trihydroxy-8-alkylated-9,10-anthraquinones with antibacterial activities from soil-derived Streptomyces sp. WS-13394. J Antibiot 75, 375–379 (2022). https://doi.org/10.1038/s41429-022-00533-7

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  • DOI: https://doi.org/10.1038/s41429-022-00533-7

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