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.

  • Brief Communication
  • Published:

Iseoic acids and bisiseoate: three new naphthohydroquinone/naphthoquinone-class metabolites from a coral-derived Streptomyces

The Journal of Antibiotics volume 76, pages 618–622 (2023)Cite this article

Subjects

Abstract

Two new naphthohydroquinone derivatives designated iseoic acids A (1) and B (2) and a new symmetrical glycerol bisester of naphthoquinonepropanoic acid designated bisiseoate (3) were isolated from the culture extract of a marine-derived actinomycete Streptomyces sp. DC4-5. The structures of 1–3 were determined by analyzing one- and two-dimensional NMR data and MS analytical data. The absolute configurations were determined by NOESY analysis and the phenylglycine methyl ester (PGME) method for 1 and by considering the structural similarity and biosynthesis for 2 and 3. Compound 3 exhibited modest cytotoxicity against P388 murine leukemia cells with an IC50 value of 19 μM.

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
Fig. 4
Fig. 5

References

  1. Bérdy J. Bioactive microbial metabolites. J Antibiot. 2005;58:1–26.

    Article  Google Scholar 

  2. Ameen F, Alnadhari S, Al-Homaidan AA. Marine microorganisms as an untapped source of bioactive compounds. Saudi J Biol Sci. 2021;28:224–31.

    Article  CAS  PubMed  Google Scholar 

  3. Demain AL. Importance of microbial natural products and the need to revitalize their discovery. J Ind Microbiol Biotechnol. 2014;41:185–201.

    Article  CAS  PubMed  Google Scholar 

  4. Bota DA, et al. Marizomib alone or in combination with bevacizumab in patients with recurrent glioblastoma: Phase I/II clinical trial data. Neurooncol Adv. 2021;3:vdab142.

    PubMed  PubMed Central  Google Scholar 

  5. Lam KS. Discovery of novel metabolites from marine actinomycetes. Curr Opin Microbiol. 2006;9:245–51.

    Article  CAS  PubMed  Google Scholar 

  6. Schinke C, Martins T, Queiroz SCN, Melo IS, Reyes FGR. Antibacterial compounds from marine bacteria, 2010−2015. J Nat Prod 2017;80:1215–28.

    Article  CAS  PubMed  Google Scholar 

  7. Mehbub MF, Tanner JE, Barnett SJ, Franco CM, Zhang W. The role of sponge-bacteria interactions: the sponge Aplysilla rosea challenged by its associated bacterium Streptomyces ACT-52A in a controlled aquarium system. Appl Microbiol Biotechnol. 2016;100:10609–26.

    Article  CAS  PubMed  Google Scholar 

  8. Fu P, et al. Antibiotic metabolites from the coral-associated actinomycete Streptomyces sp. OUCMDZ-1703. Chin J Chem. 2013;31:100–4.

    Article  CAS  Google Scholar 

  9. Nong XH, Zhang XY, Xu XY, Wang J, Qi SH. Nahuoic acids B-E, polyhydroxy polyketides from the marine-derived Streptomyces sp. SCSGAA 0027. J Nat Prod. 2015;79:141–8.

    Article  PubMed  Google Scholar 

  10. Nong XH, Wei XY, Qi SH. Pteridic acids C–G spirocyclic polyketides from the marine-derived Streptomyces sp. SCSGAA 0027. J Antibiot. 2017;70:1047–52.

    Article  CAS  Google Scholar 

  11. Sharma AR, Harunari E, Oku N, Matsuura N, Trianto A, Igarashi Y. Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus. Beilstein J Org Chem. 2020;16:297–304.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Zhang ZW, Zhou T, Harunari E, Oku N, Igarashi Y. Iseolides A–C, antifungal macrolides from a coral-derived actinomycete of the genus Streptomyces. J Antibiot. 2020;73:534–41.

    Article  CAS  Google Scholar 

  13. Yabuuchi T, Kusumi T. Phenylglycine methyl ester, a useful tool for absolute configuration determination of various chiral carboxylic acids. J Org Chem. 2000;65:397–404.

    Article  CAS  PubMed  Google Scholar 

  14. Zhang ZW, et al. Kumemicinones A−G, cytotoxic angucyclinones from a deep sea-derived actinomycete of the genus Actinomadura. J Nat Prod. 2022;85:1098–108.

    Article  CAS  PubMed  Google Scholar 

  15. Bianchi M, et al. Axenomycins, new anthelmintic, antiprotozoal and antifungal antibiotics, produced by streptomyces lisandri nov. sp. Arch Microbiol. 1974;98:289–99.

    Article  CAS  PubMed  Google Scholar 

  16. Pérez M, et al. PM100117 and PM100118, new antitumor macrolides produced by a marine Streptomyces caniferus GUA-06-05- 006A. J Antibiot. 2016;69:388–94.

    Article  Google Scholar 

  17. Alferova VA, et al. Astolides A and B, antifungal and cytotoxic naphthoquinone-derived polyol macrolactones from Streptomyces hygroscopicus. Tetrahedron 2018;74:7442–9.

    Article  CAS  Google Scholar 

  18. Takahashi I, Nishiie Y, Uosaki Y, Ochiai K. New substance GT35 and its production. Jpn. Kokai Tokkyo Koho. 1995: JPH09100290A.

  19. Takeuchi T, et al. ATP depletion assay led to the isolation of new 36-membered polyol macrolides deplelides A and B from Streptomyces sp. MM581-NF15. Org Lett. 2017;19:4207–10.

    Article  CAS  PubMed  Google Scholar 

  20. Pérez-Victoria I, et al. Structure elucidation and biosynthetic gene cluster analysis of caniferolides A-D, new bioactive glycosylated 36-membered polyol macrolides from the marine-derived Streptomyces caniferus CA-271066. Org Biomol Chem. 2019;17:2954–71.

    Article  PubMed  Google Scholar 

Download references

Acknowledgements

P388 cells were obtained from JCRB Cell Bank under an accession code JCRB0017 (Lot. 06252002). We also thank Drs. Md. Rokon Ul Karim and Tao Zhou at Toyama Prefectural University for cytotoxicity assay and structure analysis.

Author information

Authors and Affiliations

  1. Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama, 939-0398, Japan

    Zhiwei Zhang, Enjuro Harunari & Yasuhiro Igarashi

Authors
  1. Zhiwei Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Enjuro Harunari
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yasuhiro Igarashi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yasuhiro Igarashi.

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

41429_2023_644_MOESM1_ESM.docx

Supplementary Information for Iseoic acids and bisiseoate: three new naphthalene/naphthoquinone-class metabolites from a coral-derived actinomycete of the genus <i>Streptomyces</i>

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhang, Z., Harunari, E. & Igarashi, Y. Iseoic acids and bisiseoate: three new naphthohydroquinone/naphthoquinone-class metabolites from a coral-derived Streptomyces. J Antibiot 76, 618–622 (2023). https://doi.org/10.1038/s41429-023-00644-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41429-023-00644-9

Search

Advanced search

Quick links