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A novel chresdihydrochalcone from Streptomyces chrestomyceticus exhibiting activity against Gram-positive bacteria

The Journal of Antibiotics volume 73, pages 429–434 (2020)Cite this article

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Abstract

Microbial-derived natural products provide unique bioactivities and serve as a unique source of drug leads. In the present study, we isolated one new chresdihydrochalcone (1), one new chresphenylacetone (2), and one known streptimidone (3) from Streptomyces chrestomyceticus BCC 24770 using antibacterial activity-guided isolation and purification procedures. We determined their molecular weights using MS and HRMS and elucidated their chemical structures from their 1D and 2D NMR and electronic circular dichroism (ECD) spectra. Compound 1 showed moderate inhibitory activities against the Gram-positive bacteria Methicillin-resistant Staphylococcus aureus, Bacillus subtilis, and Micrococcus luteus. Cytotoxicity and hemolytic activity were not observed at a concentration of up to 100 μg ml−1. The specific antimicrobial activity and low toxicity of compound 1 indicate this compound to be a potential antibiotic candidate, especially as antibiotic resistance has become a significant public health threat.

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References

  1. Laxminarayan R, et al. Antibiotic resistance—the need for global solutions. Lancet Infect Dis. 2013;13:1057–98.

    Article  Google Scholar 

  2. de Lima Procópio RE, da Silva IR, Martins MK, de Azevedo JL, de Araújo JM. Antibiotics produced by Streptomyces. Braz J Infect Dis. 2012;16:466–71.

    Article  Google Scholar 

  3. Doernberg SB, et al. Gram-positive bacterial infections: research priorities, accomplishments, and future directions of the antibacterial resistance leadership group. Clin Infect Dis. 2017;64:S24–S9.

  4. Liu LL, et al. Four new antibacterial xanthones from the marine-derived actinomycetes Streptomyces caelestis. Mar Drugs. 2012;10:2571–83.

    Article  CAS  Google Scholar 

  5. Genilloud O. Actinomycetes: still a source of novel antibiotics. Nat Prod Rep. 2017;34:1203–32.

    Article  CAS  Google Scholar 

  6. Clardy J, Fischbach MA, Walsh CT. New antibiotics from bacterial natural products. Nat Biotechnol. 2006;24:1541–50.

    Article  CAS  Google Scholar 

  7. Bunyapaiboonsri T, et al. Polycyclic tetrahydroxanthones from Streptomyces chrestomyceticus BCC 24770. Tetrahedron. 2016;72:775–8.

    Article  CAS  Google Scholar 

  8. Halgren TA. Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94. J Comput Chem. 1996;17:490–519.

    Article  CAS  Google Scholar 

  9. Frisch MJ, et al. Gaussian 09, revision A.02. Wallingford, CT: Gaussian Inc.; 2009.

    Google Scholar 

  10. Goto H, Osawa E. Corner flapping: a simple and fast algorithm for exhaustive generation of ring conformations. J Am Chem Soc. 1989;111:8950–1.

    Article  CAS  Google Scholar 

  11. Li YX, Zhong Z, Zhang WP, Qian PY. Discovery of cationic nonribosomal peptides as Gram-negative antibiotics through global genome mining. Nat Commun. 2018;9:3273.

    Article  Google Scholar 

  12. Ecoy GAU, Chamni S, Suwanborirux K, Chanvorachote P, Chaotham C. Jorunnamycin A from Xestospongia sp. suppresses epithelial to mesenchymal transition and sensitizes anoikis in human lung cancer cells. J Nat Prod. 2019;82:1861–73.

    Article  CAS  Google Scholar 

  13. Meng J, Zhong Z, Qian PY, Paenialvin A-D. four peptide antibiotics produced by Paenibacillus alvei DSM 29. J Antibiot. 2018;71:769–77.

    Article  CAS  Google Scholar 

  14. Kim BS, Moon SS, Hwang BK. Isolation, antifungal activity, and structure elucidation of the glutarimide antibiotic, streptimidone, produced by Micromonospora coerulea. J Agric Food Chem. 1999;47:3372–80.

    Article  CAS  Google Scholar 

  15. Lavoie S, Legault J, Simard F, Chiasson É, Pichette A. New antibacterial dihydrochalcone derivatives from buds of Populus balsamifera. Tetrahedron Lett. 2013;54:1631–3.

    Article  CAS  Google Scholar 

  16. Koudokpon H, et al. Antibacterial activity of chalcone and dihydrochalcone compounds from Uvaria chamae roots against multidrug-resistant bacteria. BioMed Res Int. 2018;2018:1–10.

    Article  Google Scholar 

  17. Peng JN, et al. Structure-activity relationships of retro-dihydrochalcones isolated from Tacca sp. J Nat Prod. 2013;76:2189–94.

    Article  CAS  Google Scholar 

  18. Peng JN, et al. Evelynin, a cytotoxic benzoquinone-type retro-dihydrochalcone from Tacca chantrieri. J Nat Prod. 2010;73:1590–2.

    Article  CAS  Google Scholar 

  19. Risinger AL, et al. The bat flower: a source of microtubule-destabilizing and -stabilizing compounds with synergistic antiproliferative actions. J Nat Prod. 2013;76:1923–9.

    Article  CAS  Google Scholar 

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Acknowledgements

The authors would like to thank Mr Rui Feng of the Division of Life Science at the Hong Kong University of Science and Technology for performing the NMR experiment. The work was supported by the National Key Research and Development Program of China (2018YFA0903201) and the Hong Kong Branch of Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou) (SMSEGL20SC01).

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  1. These authors contributed equally: Weiyi She, Wenkang Ye

Authors and Affiliations

  1. SZU-HKUST Joint Ph.D. Program in Marine Environmental Science, Shenzhen University, Shenzhen, China

    Weiyi She & Wenkang Ye

  2. Department of Ocean Science, Division of Life Science and Hong Kong Branch of the Southern Marine Science and Engineering Guangdong Laboratory, The Hong Kong University of Science and Technology, Hong Kong, China

    Weiyi She, Wenkang Ye, Yusheng Shi & Pei-Yuan Qian

  3. Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China

    Le Zhou

  4. Department of Chemistry, The Hong Kong University of Science and Technology, Hong Kong, China

    Zhihong Zhang

  5. Institute for Advanced Study, Shenzhen University, 518060, Shenzhen, China

    Feng Chen

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  1. Weiyi She
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Correspondence to Feng Chen or Pei-Yuan Qian.

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She, W., Ye, W., Shi, Y. et al. A novel chresdihydrochalcone from Streptomyces chrestomyceticus exhibiting activity against Gram-positive bacteria. J Antibiot 73, 429–434 (2020). https://doi.org/10.1038/s41429-020-0298-1

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