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13-Deoxo-13-iminodutomycin, a new neuroprotective compound from Streptomyces sp. RAP78

The Journal of Antibiotics volume 75, pages 40–43 (2022)Cite this article

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Abstract

A neuroprotective compound (2) was isolated from the culture broth of the dutomycin (1) producer Streptomyces sp. RAP78. The molecular formula of 2 was established as C44H55NO16 by high-resolution FAB-MS. The structure was determined to be a new dutomycin derivative possessing an acetimidoyl group in place of an acetyl group by NMR spectroscopic analysis. 13-Deoxo-13-iminodutomycin (2) but not dutomycin (1) protected C6 rat glioma cells and N18-RE-105 rat primary retina-mouse neuroblastoma hybrid cells from glutamate-induced toxicity with EC50s of 0.12 µM and 0.72 µM, respectively.

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References

  1. Taoufik E, Probert L. Ischemic neuronal damage. Curr Pharm Des. 2008;14:3565–73.

    Article  CAS  Google Scholar 

  2. Murphy TH, Miyamoto M, Sastre A, Schnaar RL, Coyle JT. Glutamate toxicity in a neuronal cell line involves inhibition of cystine transport leading to oxidative stress. Neuron. 1989;2:1547–58.

    Article  CAS  Google Scholar 

  3. Aoyama K, Watabe M, Nakaki T. Regulation of neuronal glutathione synthesis. J Pharm Sci. 2008;108:227–38.

    Article  CAS  Google Scholar 

  4. Mawatari K, Yasui Y, Sugitani K, Takadera T, Kato S. Reactive oxygen species involved in the glutamate toxicity of C6 glioma cells via XC- antiporter system. Neuroscience. 1996;73:201–8.

    Article  CAS  Google Scholar 

  5. Hayakawa Y, Kobayashi T, Izawa M. Indanostatin, a new neuroprotective compound from Streptomyces sp. J Antibiot. 2013;66:731–3.

    Article  CAS  Google Scholar 

  6. Weisburg WG, Barns SM, Pelletier DA, Lane DJ. 16S ribosomal DNA amplification for phylogenetic study. J Bacteriol. 1991;173:697–703.

    Article  CAS  Google Scholar 

  7. Xuan LJ, Xu SH, Zhang HL, Xu YM, Chen MQ. Dutomycin, a new anthracycline antibiotic from Streptomyces. J Antibiot. 1992;45:1974–6.

    Article  CAS  Google Scholar 

  8. Yu X, Guo Q, Su G, Yang A, Hu Z, Qu C, et al. Usnic acid derivatives with cytotoxic and antifungal activities from the lichen Usnea longissima. J Nat Prod. 2016;79:1373–80.

    Article  CAS  Google Scholar 

  9. Malouf AT, Schnaar RL, Coyle JT. Characterization of a glutamic acid neurotransmitter binding site on neuroblastoma hybrid cells. J Biol Chem. 1984;259:12756–62.

    Article  CAS  Google Scholar 

  10. Shin-ya K, Kunigami T, Kim JS, Furihata K, Hayakawa Y, Seto H. Carquinostatin B, a new neuronal cell-protecting substance produced by Streptomyces exfoliatus. Biosci Biotech Biochem. 1997;61:1768–9.

    Article  CAS  Google Scholar 

  11. Domercq M, Matute C. Neuroprotection by tetracyclines. Trends Pharm Sci. 2004;25:609–12.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We are grateful to Ms. Y. Yoshimura for assistance with mass spectrometry. We also thank Dr. K. Shin-ya, National Institute of Advanced Industrial Science and Technology, for providing N18-RE-105 cells.

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  1. Department of Medicinal and Life Science, Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba, 278-8510, Japan

    Yuta Ibusuki, Shoko Kimata & Yoichi Hayakawa

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  1. Yuta Ibusuki
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  2. Shoko Kimata
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  3. Yoichi Hayakawa
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Correspondence to Yoichi Hayakawa.

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Ibusuki, Y., Kimata, S. & Hayakawa, Y. 13-Deoxo-13-iminodutomycin, a new neuroprotective compound from Streptomyces sp. RAP78. J Antibiot 75, 40–43 (2022). https://doi.org/10.1038/s41429-021-00488-1

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