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New amino-naphthoic acid derivatives produced by biological transformation using the deep-sea-derived bacterium Serinicoccus marinus KDM482

Abstract

Deep-sea-derived microorganisms are quite attractive as resources for new secondary metabolites, enzymes, and gene discovery. We have isolated many marine microorganisms from deep-sea creatures and screened the new secondary metabolites produced by them. Two new molecules designated amino-naphthoic acid derivatives (1 and 2) were obtained by biological transformation using the deep-sea derived bacterium Serinicoccus marinus KDM482 successfully. Structural analysis using 1D and 2D NMR and MS data revealed that both 1 and 2 were dimerized compounds of 3-amino-2-naphthoic acid. In biological assays, 1 and 2 moderately inhibited the growth of Malme-3M cells.

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References

  1. Costello MJ, Chaudhary C. Marine biodiversity, biogeography, deep-sea gradients, and conservation. Curr Biol. 2017;27:R511–27. https://doi.org/10.1016/j.cub.2017.04.060.

    Article  CAS  PubMed  Google Scholar 

  2. Francine KW. Omega-3 fatty acids and congnitive function. Current Opin Lipidol. 2023;34:12–21. https://doi.org/10.1097/MOL.0000000000000862.

    Article  Google Scholar 

  3. Uemura D, et al. Norhalichondrin A: an antitumor polyether macrolide from a marine sponge. J Am Chem Soc. 1985;107:4796–98. https://doi.org/10.1021/ja00302a042.

    Article  CAS  Google Scholar 

  4. Feling RH, et al. Salinosporamide A: a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus Salinospora. Angew Chem Int Ed. 2003;42:355–57.

    Article  CAS  Google Scholar 

  5. Ma L, Diao A. Marizomib, a potent second generation proteasome inhibitor from natural origin. Anticancer Agents Med Chem. 2015;15:298–306. https://doi.org/10.2174/1871520614666141114202606.

    Article  CAS  PubMed  Google Scholar 

  6. Kubota T, et al. Enantioselective utilization of D-amino acid by deep-sea microorganisms. Front Microbiol. 2016;7:511 https://doi.org/10.3389/fmicb.2016.00511.

    Article  PubMed  PubMed Central  Google Scholar 

  7. Trzoss L, et al. Seriniquinone, a selective anticancer agent, induces cell death by autophagocytosis, targeting the cancer-protective protein dermcidin. Proc Natl Acad Sci USA. 2014;111:14687–92.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Hirata AS, et al. Preclinical development of seriniquinones as selective dermcidin modulators for the treatment of melanoma. Mar Drugs. 2022;20:301. https://doi.org/10.3390/md20050301.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Kumar S, et al. MEGA X: molecular evolutionary genetics analysis across computing platforms. Mol Biol Evol. 2018;35:1547–49.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Yi H, et al. Serinicoccus marinus gen. nov., sp. nov., a novel actinomycete with L-ornithine and L-serine in the peptidoglycan. Int J Syst Evol Microbiol. 2004;54:1585–89. https://doi.org/10.1099/ijs.0.03036-0.

    Article  CAS  PubMed  Google Scholar 

  11. Ishida K, et al. New dihydronaphthothiophene derivatives by the biological transformation of seriniquinone using marine-derived actinomycete Streptomyces albogriseolus OM27-12. J Antibiot. 2022;75:9–15. https://doi.org/10.1038/s41429-021-00484-5.

    Article  CAS  Google Scholar 

  12. Korman JB, Fisher DE. Developing melanoma therapeutics: overview and update. Wiley Interdiscip Rev Syst Biol Med. 2013;5:257–71. https://doi.org/10.1002/wsbm.1210.

    Article  CAS  PubMed  Google Scholar 

  13. Lim SY, et al. Mechanisms and strategies to overcome resistance to molecularly targeted therapy for melanoma. Cancer. 2017;123:2118–29. https://doi.org/10.1002/concr.30435.

    Article  CAS  PubMed  Google Scholar 

  14. Jiang X, et al. Discovery of a new asymmetric dimer nenestatin B and implications of a dimerizing enzyme in a deep sea actinomycete. Org Biomol Chem. 2021;19:4243–47. https://doi.org/10.1039/d1ob00310k.

    Article  CAS  PubMed  Google Scholar 

  15. Liu Z, et al. Functional characterization of the halogenase SpmH and discovery of new deschloro-tryptophan dimers. Org Biomol Chem. 2019;17:1053–57. https://doi.org/10.1039/c8ob02775g.

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

We thank Ms. Saori Aoyama for supplying the deep-sea creatures. This work was supported by the Grant for Scientific Research from the Agriculture Technology and Innovation Research Institute, Kindai University.

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Correspondence to Takashi Fukuda.

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Sakaguchi, M., Kikuchi, K., Okamura, R. et al. New amino-naphthoic acid derivatives produced by biological transformation using the deep-sea-derived bacterium Serinicoccus marinus KDM482. J Antibiot 78, 573–576 (2025). https://doi.org/10.1038/s41429-025-00845-4

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