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New potentiators of amphotericin B activity, shodoamides A to C produced by Pseudophialophora sp. BF-0158

The Journal of Antibiotics volume 76, pages 579–584 (2023)Cite this article

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A Correction to this article was published on 13 March 2025

This article has been updated

Abstract

During our screening program for new potentiators of amphotericin B activity against Candida albicans, shodoamides A to C (1–3) were isolated from a culture broth of the fungus Pseudophialophora sp. BF-0158 fermented under shaking conditions. A known congener named shodoamide D (4) in this paper was obtained from a culture broth of the BF-0158 strain fermented under static conditions. The structures of 1–4 were assigned based on spectroscopic analyses, including NMR and MS, and were found to have a common N-(2´,3´,4´-trihydroxybutyl)-6-methyl-2,4-tetradecadienamide structure. Compounds 1–3 exhibited no antifungal activity, but they induced up to 32-fold increases in amphotericin B activity against C. albicans by a microdilution method.

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Change history

  • 03 March 2025

    The original online version of this article was revised: The authors of the above article noted an error in the publication of this paper, whereby the incorrect data were used for the chemical shifts of hydroxyl groups.

    In the 'Structural elucidation of shodoamide' section on page 580, right-hand column, please replace the chemical shifts of 12-OH for 2 and 13-OH for 3 with the following corrected values:

    12-OH: δ 4.20 (previously reported as δ 4.43)

    13-OH: δ 4.28 (previously reported as δ 4.43)

    This revision is based on studies of the total synthesis of shodoamide C.

    Additionally, the corrected data in Table 2 are shown below.

    The original article has been corrected.

  • 13 March 2025

    A Correction to this paper has been published: https://doi.org/10.1038/s41429-025-00814-x

References

  1. Trejo WH, Bennett RE. Streptomyces nodosus sp. n., the amphotericin-producing organism. J Bacteriol. 1963;85:436–9.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Uchida R, Kondo A, Yagi A, Nonaka K, Masuma R, Kobayashi K, Tomoda H. Simpotentin, a new potentiator of amphotericin B activity against Candida albicans, produced by Simplicillium minatense FKI-4981. J Antibiot. 2019;72:134–40.

    Article  CAS  Google Scholar 

  3. Ohtawa M, Shimizu E, Saito A, Sakamoto S, Waki A, Kondo A, Yagi A, Uchida R, Tomoda H, Nagamitsu T. Total synthesis and absolute configuration of simpotentin, a potentiator of amphotericin B activity. Org Lett. 2019;21:5596–9.

    Article  CAS  PubMed  Google Scholar 

  4. Fukuda T, Nagai K, Yagi A, Kobayashi K, Uchida R, Yasuhara T, Tomoda H. Nectriatide, a potentiator of amphotericin B activity from Nectriaceae sp. BF-0114. J Nat Prod. 2019;82:2673–81.

    Article  CAS  PubMed  Google Scholar 

  5. Yagi A, Uchida R, Kobayashi K, Tomoda H. Polyketide glycosides phialotides A to H, new potentiators of amphotericin B activity, produced by Pseudophialophora sp. BF-0158. J Antibiot. 2020;73:211–23.

    Article  CAS  Google Scholar 

  6. Yagi A, Yamaguchi Y, Kawasaki K, Usui E, Yamazaki H, Uchida R. New piericidin rhamnosides as potentiators of amphotericin B activity against Candida albicans produced by actinomycete strain TMPU-A0287. J Antibiot. 2023;76:65–74.

    Article  CAS  Google Scholar 

  7. Bolessa EA, Schwartz RE, Bills GF, Giacobbe RA, Pelaez PF, Cabello AA, Diez MT, Martin FI, Vincente PF. Antifungal agent formulations containing alkadienes. United States, US5461071 A 1995-10-24.

  8. Luo J, Walsh E, Blystone D, Zhang N. Five new Pseudophialophora species from grass roots in the oligotrophic pine barrens ecosystem. Fungal Biol. 2015;119:1205–15.

    Article  PubMed  Google Scholar 

  9. Luo J, Walsh E, Zhang N. Four new species in Magnaporthaceae from grass roots in New Jersey Pine Barrens. Mycologia. 2014;106:580–8.

    Article  PubMed  Google Scholar 

  10. Zhu JN, Yu YJ, Dai MD, Zeng YL, Lu XJ, Wang L, Liu XH, Su ZZ, Lin FC. A New Species in Pseudophialophora from wild rice and beneficial potential. Front Microbiol. 2022;13:845104.

    Article  PubMed  PubMed Central  Google Scholar 

  11. Ishijima H, Uchida R, Ohtawa M, Kondo A, Nagai K, Shima K, Nonaka K, Masuma R, Iwamoto S, Onodera H, Nagamitsu T, Tomoda H. Simplifungin and valsafungins, antifungal antibiotics of fungal origin. J Org Chem. 2016;81:7373–83.

    Article  CAS  PubMed  Google Scholar 

  12. Clinical and Laboratory Standards Institute (CLSI). Reference method for broth dilution antifungal susceptibility testing of yeasts. 3rd edition; CLSI document M27-A3. Wayne, PA: Clinical and Laboratory Standards Institute; 2008.

  13. Clinical and Laboratory Standards Institute (CLSI). Reference method for broth dilution antifungal susceptibility testing of filamentous fungi; approved standard CLSI document M38-A2. 3rd edition. Wayne, PA: Clinical and Laboratory Standards Institute; 2008

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Acknowledgements

We express our thanks to Dr Kenichiro Nagai and Ms Noriko Sato of the School of Pharmacy, Kitasato University, for measuring NMR and mass spectra.

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Authors and Affiliations

  1. Division of Natural Product Chemistry, Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai, Miyagi, 981-8558, Japan

    Akiho Yagi & Ryuji Uchida

  2. Department of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan

    Masahiro Kashima, Hiroyuki Ishijima & Hiroshi Tomoda

  3. Drug Discovery Laboratory, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan

    Hiroshi Tomoda

Authors
  1. Akiho Yagi
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  2. Masahiro Kashima
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  3. Hiroyuki Ishijima
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  4. Hiroshi Tomoda
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  5. Ryuji Uchida
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Corresponding authors

Correspondence to Hiroshi Tomoda or Ryuji Uchida.

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The original online version of this article was revised: The authors of the above article noted an error in the publication of this paper, whereby the incorrect data were used for the chemical shifts of hydroxyl groups.

In the 'Structural elucidation of shodoamide' section on page 580, right-hand column, please replace the chemical shifts of 12-OH for 2 and 13-OH for 3 with the following corrected values:

12-OH: δ 4.20 (previously reported as δ 4.43)

13-OH: δ 4.28 (previously reported as δ 4.43)

This revision is based on studies of the total synthesis of shodoamide C.

Additionally, the corrected data in Table 2 are shown below.

The original article has been corrected.

Supplementary information

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Yagi, A., Kashima, M., Ishijima, H. et al. New potentiators of amphotericin B activity, shodoamides A to C produced by Pseudophialophora sp. BF-0158. J Antibiot 76, 579–584 (2023). https://doi.org/10.1038/s41429-023-00642-x

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