Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Article
  • Published:

Mollicellins S-U, three new depsidones from Chaetomium brasiliense SD-596 with anti-MRSA activities

Abstract

Fungi are important resources for drug development, as they have a diversity of genes, that can produce novel secondary metabolites with effective bioactivities. Here, five depsidone-based analogs were isolated from the rice media of Chaetomium brasiliense SD-596. Their structures were elucidated using NMR and mass spectrometry analysis. Five compounds, including three new depsidone analogs, mollicellin S (1), mollicellin T (2), and mollicellin U (3), and two known compounds, mollicellin D (4) and mollicellin H (5), exhibited significant inhibition against Staphylococcus aureus and methicillin-resistant Staphylococcus aureus (MRSA), with MIC values ranging from 6.25 to 12.5 μg ml−1. Herein, we identified the predicted plausible biosynthetic cluster of the compounds and discussed the structure-activity relationship. Finally, we found that the introduction of aldehyde and methoxyl groups provide marked improvement for the inhibition against MRSA.

This is a preview of subscription content, access via your institution

Access options

Buy this article

Prices may be subject to local taxes which are calculated during checkout

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Zhang Q, Li HQ, Zong SC, Gao JM, Zhang AL. Chemical and bioactive diversities of the genus Chaetomium secondary metabolites. Mini Rev Med Chem. 2012;12:127–48.

    Article  Google Scholar 

  2. Li GY, Li BG, Yang T, Liu GY, Zhang GL. Secondary metabolites from the fungus Chaetomium brasiliense. Helv Chim Acta. 2008;91:124–9.

    Article  CAS  Google Scholar 

  3. Khumkomkhet P, Kanokmedhakul S, Kanokmedhakul K, Hahnvajanawong C, Soytong K. Antimalarial and cytotoxic depsidones from the fungus Chaetomium brasiliense. J Nat Prod. 2009;72:1487–91.

    Article  CAS  Google Scholar 

  4. Oh H, Swenson DC, Gloer JB, Wicklow DT, Dowd PF. Chaetochalasin A: a new bioactive metabolite from Chaetomium brasiliense. Tetrahedron Lett. 1998;39:7633–6.

    Article  CAS  Google Scholar 

  5. Luo R, Liu B, Xie Y, Li Z, Huang W, Yuan J, et al. SOAPdenovo2: an empirically improved memory-efficient short-read de novo assembler. GigaScience. 2012;1:18–18.

    Article  Google Scholar 

  6. Weber T, Blin K, Duddela S, Krug D, Kim HU, Bruccoleri R, et al. antiSMASH 3.0-a comprehensive resource for the genome mining of biosynthetic gene clusters. Nucleic Acids Res. 2015;43:W237–43.

    Article  CAS  Google Scholar 

  7. Wang QX, Bao L, Yang XL, Guo H, Yang RN, Ren B, et al. Polyketides with antimicrobial activity from the solid culture of an endolichenic fungus Ulocladium sp. Fitoterapia. 2012;83:209–14.

    Article  CAS  Google Scholar 

  8. Ouyang J, Mao Z, Guo H, Xie Y, Cui Z, Sun J, et al. Mollicellins O-R, four new depsidones isolated from the endophytic fungus Chaetomium sp. Eef-10. Molecules. 2018;23:3218.

    Article  Google Scholar 

  9. Cai R, Chen S, Long Y, Li C, Huang X, She Z. Depsidones from Talaromyces stipitatus SK-4, an endophytic fungus of the mangrove plant Acanthus ilicifolius. Phytochem Lett. 2017;20:196–9.

    Article  CAS  Google Scholar 

  10. Niu S, Liu D, Hu X, Proksch P, Shao Z, Lin W. Spiromastixones A–O, antibacterial chlorodepsidones from a deep-sea-derived Spiromastix sp. fungus. J Nat Prod. 2014;77:1021–30.

    Article  CAS  Google Scholar 

  11. Saetang P, Rukachaisirikul V, Phongpaichit S, Preedanon S, Sakayaroj J, Borwornpinyo S, et al. Depsidones and an α-pyrone derivative from Simpilcillium sp. PSU-H41, an endophytic fungus from Hevea brasiliensis leaf. Phytochemistry. 2017;143:115–23.

    Article  CAS  Google Scholar 

  12. Sisodia R, Geol M, Verma S, Rani A, Dureja P. Antibacterial and antioxidant activity of lichen species Ramalina roesleri. Nat Prod Res. 2013;27:2235–9.

    Article  CAS  Google Scholar 

  13. Sultana N, Afolayan AJ. A new depsidone and antibacterial activities of compounds from Usnea undulata Stirton. J Asian Nat Prod Res. 2011;13:1158–64.

    Article  CAS  Google Scholar 

  14. Sweidan A, Chollet-Krugler M, Sauvager A, van de Weghe P, Chokr A, Bonnaure-Mallet M, et al. Antibacterial activities of natural lichen compounds against Streptococcus gordonii and Porphyromonas gingivalis. Fitoterapia. 2017;121:164–9.

    Article  CAS  Google Scholar 

  15. Armaleo D, Sun X, Culberson C. Insights from the first putative biosynthetic gene cluster for a lichen depside and depsidone. Mycologia. 2011;103:741–54.

    Article  CAS  Google Scholar 

  16. Kroken S, Glass NL, Taylor JW, Yoder OC, Turgeon BG. Phylogenomic analysis of type I polyketide synthase genes in pathogenic and saprobic ascomycetes. Proc Natl Acad Sci USA. 2003;100:15670–5.

    Article  CAS  Google Scholar 

  17. Ibrahim SRM, Mohamed GA, Al Haidari RA, El-Kholy AA, Zayed MF, Khayat MT. Biologically active fungal depsidones: Chemistry, biosynthesis, structural characterization, and bioactivities. Fitoterapia. 2018;129:317–65.

    Article  CAS  Google Scholar 

  18. Klaiklay S, Rukachaisirikul V, Aungphao W, Phongpaichit S, Sakayaroj J. Depsidone and phthalide derivatives from the soil-derived fungus Aspergillus unguis PSU-RSPG199. Tetrahedron Lett. 2016;57:4348–51.

    Article  CAS  Google Scholar 

  19. Zhang Y, Mu J, Feng Y, Wen L, Han J. Four chlorinated depsidones from a seaweed-derived strain of Aspergillus unguis and their new biological activities. Nat Prod Res. 2014;28:503–6.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge the financial support of the National Key R&D Program of China (Nos. 2017YFF0209900, 2017YFF0209904, 2017YFF0209902), National Natural Science Foundation of China (31770024), Qilu University of Technology (Shandong Academy of Sciences) International Cooperation Program (2019GHPY07), the Taishan Scholar Project from Shandong Province to Lixin Zhang, Xuekui Xia, Qilu University of Technology (Shandong Academy of Sciences) Joint Fund for Young Doctors (2017BSH2016), Science, Education and Industry Integration Innovation Pilot Project of Qilu University of Technology (Shandong Academy of Sciences) (2020KJC-ZD08).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Lixin Zhang or Xuekui Xia.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhao, P., Yang, M., Zhu, G. et al. Mollicellins S-U, three new depsidones from Chaetomium brasiliense SD-596 with anti-MRSA activities. J Antibiot 74, 317–323 (2021). https://doi.org/10.1038/s41429-020-00398-8

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41429-020-00398-8

This article is cited by

Search

Quick links