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:

Antimalarial 9-methoxystrobilurin derivatives from cultures of the basidiomycete Favolaschia minutissima

The Journal of Antibiotics (2024)Cite this article

Subjects

Abstract

Investigation of cultures of the basidiomycete Favolaschia minutissima TBRC-BCC 19434 led to the isolation of two undescribed β-methoxyacrylate metabolites, 9-methoxystrobilurins R (1) and S (2), and a degraded aldehyde derivative, favodehyde E (3). 9-Methoxystrobilurin derivatives 1 and 2 exhibited significant antimalarial activity against Plasmodium falciparum K1 (multidrug-resistant strain) with IC50 values of 0.12 and 0.21 μM, respectively.

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

Access options

Buy this article

  • Purchase on Springer Link
  • Instant access to full article PDF
Buy now

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

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Nofiani R, de Mattos-Shipley K, Lebe KE, Han LC, Iqbal Z, Bailey AM, Willis CL, Simpson TJ, Cox RJ. Strobilurin biosynthesis in Basidiomycete fungi. Nat Comm 2018;9:3940. https://doi.org/10.1038/s41467-018-06202-4

    Article  CAS  Google Scholar 

  2. Iqbal Z, Han LC, Soares-Sello AM, Nofiani R, Thormann G, Zeeck A, Cox RJ, Willis CL, Simpson TJ. Investigations into the biosynthesis of the antifungal strobilurins. Org Biomol Chem 2018;16:5524–32. https://doi.org/10.1039/c8ob00608c

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Clough JM. The strobilurins, oudemansins, and myxothiazols, fungicidal derivatives of β-methoxyacrylic acid. Nat Prod Rep. 1993;10:565–74. https://doi.org/10.1039/NP9931000565

    Article  CAS  PubMed  Google Scholar 

  4. Sauter H, Steglich W, Anke T. Strobilurins: Evolution of a new class of active substances. Angew Chem Int Ed 1999;38:1328–49. https://doi.org/10.1002/(SICI)1521-3773(19990517)38:10<1328::AID-ANIE1328>3.0.CO;2-1

    Article  Google Scholar 

  5. Balba H. Review of strobilurin fungicide chemicals. J Environ Sci Health Part B 2007;42:441–51. https://doi.org/10.1080/03601230701316465

    Article  CAS  Google Scholar 

  6. Zapf S, Werle A, Anke T, Klostermeyer D, Steffan B, Steglich W. 9-Methoxystrobilurins – a link between strobilurins and oudemansins. Angew Chem Int Ed Engl. 1995;34:196–8. https://doi.org/10.1002/anie.199501961

    Article  CAS  Google Scholar 

  7. Wood KA, Kau DA, Wringley SK, Beneyto R, Renno DV, Ainsworth AM, Penn J, Hill D, Killacky J, Depledge P. Novel β-methoxyacrylates of the 9-methoxystrobilurin and oudemansin classes produced by the basidiomycete Favolaschia pustulosa. J Nat Prod 1996;59:646–9. https://doi.org/10.1021/np960325m

    Article  CAS  PubMed  Google Scholar 

  8. Nicholas GM, Blunt JW, Cole ALJ, Munro MHG. Investigation of the New Zealand basidiomycete Favolaschia calocera: revision of the structures of 9-methoxystrobilurins K and L, strobilurin D, and hydroxystrobilurin D. Tetrahedron Lett. 1997;38:7465–8. https://doi.org/10.1016/S0040-4039(97)01758-9

    Article  CAS  Google Scholar 

  9. Chepkirui C, Richter C, Matasyoh JC, Stadler M. Monochlorinated calocerins A–D and 9-oxostrobilurin derivatives from the basidiomycete Favolaschia calocera. Phytochemistry. 2016;132:95–101. https://doi.org/10.1016/j.phytochem.2016.10.001

    Article  CAS  PubMed  Google Scholar 

  10. Kornsakulkarn J, Thongpanchang C, Chainoy R, Choowong W, Nithithanasilp S, Thongpanchang T. Bioactive metabolites from cultures of basidiomycete Favolaschia tonkinensis. J Nat Prod 2010;73:759–62. https://doi.org/10.1021/np900777r

    Article  CAS  PubMed  Google Scholar 

  11. Kornsakulkarn J, Palasarn S, Choowong W, Thongpanchang T, Boonyuen N, Choeyklin R, Boonpratuang T, Isaka M, Thongpanchang C. Antimalarial 9-methoxystrobilurins, oudemansins, and related polyketides from cultures of basidiomycete Favolaschia species. J Nat Prod 2020;83:905–17. https://doi.org/10.1021/acs.jnatprod.9b00647

    Article  CAS  PubMed  Google Scholar 

  12. Palasarn S, Pruksatrakul T, Choowong W, Wiriyathanawudhiwong N, Thitiya Boonpratuang T, Surawatanawong P, Thongpanchang C. Isaka. Oudemansin and 9-methoxystrobilurin derivatives with antimalarial activity from cultures of the basidiomycete Favolaschia minutissima: assignments of the absolute configurations of the isoprene-derived units. Org Biomol Chem 2023;21:7944–53. https://doi.org/10.1039/d3ob01472

    Article  CAS  PubMed  Google Scholar 

  13. Zhang QY, Dai YC. Taxonomy and phylogeny of the Favolaschia calocera complex (Mycenaceae) with descriptions of four new species. Forests. 2021;12:1397 https://doi.org/10.3390/f12101397

    Article  Google Scholar 

  14. Bertram G, Sherer A, Steglich W, Weber W, Anke T. Total synthesis of (±)-strobilurin E. Tetrahedron Lett. 1996;37:7955–8. https://doi.org/10.1016/0040-4039(96)01833-3

    Article  CAS  Google Scholar 

  15. Kornsakulkarn J, Choowong W, Choeyklin R, Boonpratuang T, Isaka M, Thongpanchang C. Antimalarial (9Z)-9-methoxystrobilurins from cultures of Basidiomycete Favolaschia xtbgensis TBRC-BCC 18687. Tetrahedron. 2024;153:133847. https://doi.org/10.1016/j.tet.2024.133847

    Article  CAS  Google Scholar 

  16. Desjardins RE, Canfield CJ, Haynes JD, Chulay JD. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique. Antimicrob Agents Chemother 1979;16:710–8. https://doi.org/10.1128/AAC.16.6.710

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Hunt L, Jordan M, De Jesus M, Wurm FM. GFP-expressing mammalian cells for fast, sensitive, noninvasive cell growth assessment in a kinetic mode. Biotechnol. Bioeng. 1999;65:201–5.

Download references

Acknowledgements

Financial supports from National Research Council of Thailand (NRCT) (Grant No. N42A660851) is gratefully acknowledged.

Author information

Authors and Affiliations

  1. National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), 111 Thailand Science Park, Phahonyothin Road, Klong Luang, Pathumthani, 12120, Thailand

    Somporn Palasarn, Kitlada Srichomthong, Chawanee Thongpanchang & Masahiko Isaka

  2. National Biobank of Thailand, National Science and Technology Development Agency (NSTDA), 111 Thailand Science Park, Phahonyothin Road, Klong Luang, Pathumthani, 12120, Thailand

    Tuksaporn Thummarukcharoen

Authors
  1. Somporn Palasarn
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kitlada Srichomthong
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tuksaporn Thummarukcharoen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Chawanee Thongpanchang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Masahiko Isaka
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Masahiko Isaka.

Ethics declarations

Conflict of interest

The authors declare no competing interests.

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

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Palasarn, S., Srichomthong, K., Thummarukcharoen, T. et al. Antimalarial 9-methoxystrobilurin derivatives from cultures of the basidiomycete Favolaschia minutissima. J Antibiot (2024). https://doi.org/10.1038/s41429-024-00733-3

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1038/s41429-024-00733-3

Search

Advanced search

Quick links