Original Article

Wakodecalines A and B, new decaline metabolites isolated from a fungus Pyrenochaetopsis sp. RK10-F058

  • The Journal of Antibiotics 71, 123128 (2018)
  • doi:10.1038/ja.2017.103
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Abstract

Two new decaline metabolites, wakodecalines A and B, were isolated from a fungus, Pyrenochaetopsis sp. RK10-F058, by screening for structurally unique metabolites using LC/MS analysis. Their structures were determined on the basis of NMR and mass spectrometric measurements. The absolute structures were confirmed by a combination of chemical methods including chemical degradation, a modified Mosher’s method and Marfey’s method, and comparison of the experimental electronic CD (ECD) spectrum with calculated one. Both compounds had a cyclopentanone-fused decaline skeleton and an N-methylated amino acid moiety derived from a serine. They showed moderate antimalarial activity against the Plasmodium falciparum 3D7 strain.

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References

  1. 1.

    An overview on the diversity of actinomycete metabolites. Actinomycetol 15, 11–14 (2001).

  2. 2.

    Bioactive microbial metabolites. J. Antibiot. 58, 1–26 (2005).

  3. 3.

    & Natural products as sources of new drugs from 1981 to 2014. J. Nat. Prod. 79, 629–661 (2016).

  4. 4.

    , , & ChemGPS-NP: tuned for navigation in biologically relevant chemical space. J. Nat. Prod. 70, 789–794 (2007).

  5. 5.

    in Bioprobes (ed. 1–14 (Springer, Berlin, (2000).

  6. 6.

    , , , & Reveromycin A, a new antibiotic which inhibits the mitogenic activity of epidermal growth factor. J. Antibiot. 44, 259–261 (1991).

  7. 7.

    et al. Epoxyquinol A, a highly functionalized pentaketide dimer with antiangiogenic activity isolated from fungal metabolites. J. Am. Chem. Soc. 124, 3496–3497 (2002).

  8. 8.

    et al. Azaspirene: a novel angiogenesis inhibitor containing a 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione skeleton produced by the fungus Neosartorya sp. Org. Lett. 4, 2845–2848 (2002).

  9. 9.

    & Systematic isolation of microbial metabolites for natural products depository (NPDepo). Pure Appl. Chem. 81, 1407–1420 (2012).

  10. 10.

    , , , & Construction of a microbial natural product library for chemical biology studies. Curr. Opin. Chem. Biol. 16, 101–108 (2012).

  11. 11.

    et al. Verticilactam, a new macrolactam isolated from a microbial metabolite fraction library. Org. Lett. 12, 4564–4567 (2010).

  12. 12.

    et al. Spirotoamides A and B, novel 6,6-spiroacetal polyketides isolated from a microbial metabolite fraction library. J. Antibiot. 65, 123–128 (2012).

  13. 13.

    et al. Pyrrolizilactone, a new pyrrolizidinone metabolite produced by a fungus. J. Antibiot. 66, 621–623 (2013).

  14. 14.

    et al. Equisetin and a novel opposite stereochemical homolog phomasetin, two fungal metabolites as inhibitors of HIV-1 integrase. Tetrahedron Lett. 39, 2243–2246 (1998).

  15. 15.

    et al. A new enzyme involved in the control of the stereochemistry in the decalin formation during equisetin biosynthesis. Biochem. Biophys. Res. Commun. 460, 210–215 (2015).

  16. 16.

    , , , & Characterization of the Fusarium toxin equisetin: the use of phenylboronates in structure assignment. J. Am. Chem. Soc. 111, 8223–8231 (1989).

  17. 17.

    et al. Bioactive natural products from fungicolous Hawaiian isolates: secondary metabolites from a Phialemoniopsis sp. Mycology 5, 120–129 (2014).

  18. 18.

    , , & High-Field FT NMR application of Mosher’s method. The absolute configurations of marine terpenoids. J. Am. Chem. Soc. 113, 4092–4096 (1991).

  19. 19.

    Determination of D-amino acids. II. Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene. Carlsberg Res. Commun. 49, 591–596 (1984).

  20. 20.

    & Circular dichroism calculation for natural products. J. Nat. Med. 68, 1–10 (2014).

  21. 21.

    & Tetramic and tetronic acids: an update on new derivatives and biological aspects. Bioorg. Med. Chem. 16, 4203–4221 (2008).

  22. 22.

    et al. Fusarisetin A, an acinar morphogenesis inhibitor from a soil fungus, Fusarium sp. FN080326. J. Am. Chem. Soc. 133, 6865–6867 (2011).

  23. 23.

    et al. Correction to fusarisetin A, an acinar morphogenesis inhibitor from a soil fungus, Fusarium sp. FN080326. J. Am. Chem. Soc. 134, 7194 (2012).

  24. 24.

    , & Altercrasin A, a novel decalin derivative with spirotetramic acid, produced by a sea urchin-derived Alternaria sp. Tetrahedron Lett. 56, 1229–1232 (2015).

  25. 25.

    , , & The facile production of N-methyl amino acid via oxazolidinones. Aust. J. Chem. 53, 425–433 (2000).

  26. 26.

    et al. Gaussian 09 Revision E.01, Gaussian, Wallingford, CT, (2013).

  27. 27.

    et al. RK-1355A and B, novel quinomycin derivatives isolated from a microbial metabolites fraction library based on NPPlot screening. J. Antibiot. 67, 323–329 (2014).

  28. 28.

    et al. Opantimycin A, a new metabolite isolated from Streptomyces sp. RK88-1355. J. Antibiot. 70, 222–225 (2017).

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Acknowledgements

We thank Dr T Nakamura at RIKEN for the HRESITOFMS measurements; Ms H Aono, Ms M Tanaka, Dr J Otaka and Mr K Yamamoto at RIKEN for performing the activity tests; and Dr M Ueki, Ms N Morita and Mr T Abukawa at RIKEN for maintaining the RIKEN broth library. The computer calculation using the Gaussian 09 was performed using the HOKUSAI GreatWave at RIKEN. This work was supported in part by the JSPS KAKENHI, a grant-in-aid from the Research Program on Hepatitis from the Japan Agency for Medical Research and Development (AMED), and the Science and Technology Research Promotion Program for Agriculture, Forestry, Fisheries, and Food Industry.

Author information

Affiliations

  1. RIKEN Center for Sustainable Resource Science, Chemical Biology Research Group, Wako, Saitama, Japan

    • Toshihiko Nogawa
    • , Takeshi Shimizu
    • , Akiko Okano
    • , Yushi Futamura
    •  & Hiroyuki Osada
  2. RIKEN Center for Sustainable Resource Science, Natural Product Biosynthesis Research Unit, Saitama, Japan

    • Naoki Kato
    •  & Shunji Takahashi

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Competing interests

The authors declare no conflict of interest.

Corresponding author

Correspondence to Hiroyuki Osada.

Supplementary information

Supplementary Information accompanies the paper on The Journal of Antibiotics website (http://www.nature.com/ja)