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:

New piericidin rhamnosides as potentiators of amphotericin B activity against Candida albicans produced by actinomycete strain TMPU-A0287

The Journal of Antibiotics volume 76, pages 65–74 (2023)Cite this article

Subjects

A Correction to this article was published on 21 September 2023

This article has been updated

Abstract

Four new piericidin rhamnosides (2, 4–6) together with three known piericidins (1, 3, 7) were isolated from the culture broth of the unidentified actinomycete strain TMPU-A0287 as potentiators of antifungal amphotericin B (AmB) activity. The structures of piericidins were elucidated by spectroscopic analyses, including NMR and MS. Compounds 2 and 4–6 possessed a ketone at C-10 and one or two methoxy groups on the rhamnose in their structures. Compounds 1–7 did not exhibit antifungal activity against Candida albicans and all potentiated AmB activity. The MIC values of AmB against C. albicans combined with 1–7 (4.0 μg ml−1) decreased from 0.50 to 0.063 or 0.031 μg ml−1, yielding an 8- or 16-fold increase in AmB activity.

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

Change history

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. Aversa F, Busca A, Candoni A, Cesaro S, Girmenia C, Luppi M, Nosari AM, Pagano L, Romani L, Rossi G, Venditti A, Novelli A. Liposomal amphotericin B (AmBisome®) at beginning of its third decade of clinical use. J Chemother. 2017;29:131–43.

    Article  CAS  PubMed  Google Scholar 

  3. Stone NR, Bicanic T, Salim R, Hope W. Liposomal Amphotericin B (AmBisome(®)): A Review of the Pharmacokinetics, Pharmacodynamics, Clinical Experience and Future Directions. Drugs 2016;76:485–500.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. 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 

  5. 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 

  6. Yagi Y, 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 

  7. 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 

  8. Clinical and Laboratory Standards Institute (CLSI): Reference method for broth dilution antifungal susceptibility testing of yeasts. 4rd ed; CLSI document M27-A4. Wayne, PA: Clinical and Laboratory Standards Institute; 2017.

  9. Clinical and Laboratory Standards Institute (CLSI): Reference method for broth dilution antifungal susceptibility testing of filamentous fungi; approved standard CLSI document M38-A3. 3rd ed. Wayne, PA: Clinical and Laboratory Standards Institute; 2017.

  10. Clinical and Laboratory Standards Institute (CLSI): Reference methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; approved standard CLSI document M07-A9. 9th ed. Wayne, PA: Clinical and Laboratory Standards Institute; 2012.

  11. Kimura K, Nakayama S, Nakajima N, Yoshihama M, Miyata N, Kawanishi G. A new piericidin rhamnoside, 3’-rhamnopiericidin A1. J Antibiot. 1990;43:1341–3.

    Article  CAS  Google Scholar 

  12. Tamura S, Takahashi N, Miyamoto S, Mori R, Suzuki S, Nagatsu J. Isolation and physiological activities of piericidin A, a natural insecticide produced by Streptomyces. Agr Biol Chem. 1963;2:576–82.

    Article  Google Scholar 

  13. Schnermann MJ, Romero FA, Hwang I, Nakamaru-Ogiso E, Yagi T, Boger DL. Total synthesis of piericidin A1 and B1 and key analogues. J Am Chem Soc. 2006;128:11799–807.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Bock K, Lundt I, Pedersen C. Assignment of anomer structure to carbohydrates through geminal 13C-1H coupling constants. Tetrahedron Lett. 1973;13:1037–40.

    Article  Google Scholar 

  15. Tanaka T, Nakashima T, Ueda T, Tomii K, Kouno I. Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chem Pharm Bull. 2007;55:899–901.

    Article  CAS  Google Scholar 

  16. Azad SM, Jin Y, Ser HL, Goh BH, Lee LH, Thawai C, He YW. Biological insights into the piericidin family of microbial metabolites. J Appl Microbiol. 2022;132:772–84.

    Article  CAS  PubMed  Google Scholar 

  17. Takahashi N, Suzuki A, Kimura Y, Miyamoto S, Tamura S, Mitsui T, Fukami J. Isolation, structure and physiological activities of piericidin B, natural insecticide produced by a Streptomyces. Agr Biol Chem. 1968;32:1115–22.

    CAS  Google Scholar 

  18. Two binding sites of inhibitors in NADH: ubiquinone oxidoreductase (complex I), Friedrich T, van Heek P, Leif H, Ohnishi T, Forche E, Kunze B, Jansen R, Trowitzsch-Kienast W, Höfle G, Reichenbach H, Weiss H. Eur J Biochem. 1994;219:691–8.

    Article  Google Scholar 

Download references

Acknowledgements

We express our thanks to Mr. T. Matsuki and S. Sato of Tohoku Medical and Pharmaceutical University for the NMR and mass spectra measurements.

Author information

Authors and Affiliations

  1. Division of Natural Product Chemistry, Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Sendai, Miyagi, Japan

    Akiho Yagi, Yuga Yamaguchi, Keiko Kawasaki, Eri Usui, Hiroyuki Yamazaki & Ryuji Uchida

Authors
  1. Akiho Yagi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yuga Yamaguchi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Keiko Kawasaki
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Eri Usui
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Hiroyuki Yamazaki
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ryuji Uchida
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ryuji Uchida.

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.

The original online version of this article was revised: The authors of the above article noticed the drawing error of α-L-rhamnose in the publication of this paper in Fig. 3. The correct structure is shown below.

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

Yagi, A., Yamaguchi, Y., Kawasaki, K. et al. New piericidin rhamnosides as potentiators of amphotericin B activity against Candida albicans produced by actinomycete strain TMPU-A0287. J Antibiot 76, 65–74 (2023). https://doi.org/10.1038/s41429-022-00581-z

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41429-022-00581-z

This article is cited by

Search

Advanced search

Quick links