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New dihydronaphthothiophene derivatives by the biological transformation of seriniquinone using marine-derived actinomycete Streptomyces albogriseolus OM27-12

The Journal of Antibiotics volume 75, pages 9–15 (2022)Cite this article

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Abstract

Seriniquinone was originally isolated as a melanoma-selective anti-cancer agent from a culture broth of marine bacteria. Pharmacological studies on its selectivity and unique target are ongoing. A new dihydronaphthothiophene (1) was synthesized by the biological transformation of seriniquinone using marine-derived actinomycete Streptomyces albogriseolus OM27-12, and its derivatives (2–4) were chemically synthesized. Compounds 1–4 exhibited selective cytotoxic activity against melanoma and improved solubility.

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Fig. 1
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Scheme 1

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Funding

This work was supported by JSPS KAKENHI Grant Number 19K05855 (T.F.) and the Front and Grant for Scientific Research from the Faculty of Agriculture, Kindai University (T.F.).

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Authors and Affiliations

  1. Department of Fisheries, Faculty of Agriculture, Kindai University, Nara, Japan

    Kohei Ishida, Teruki Tanaka, Masashi Ando, Yasuyuki Tsukamasa & Takashi Fukuda

  2. Microbial Chemistry and Medicinal Research Laboratories, Graduate School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan

    Kenichiro Nagai

  3. Graduate School of Marine Science and Technology, Tokyo University of Marine Science and Technology, Tokyo, Japan

    Yoshimasa Furuichi & Takeshi Terahara

  4. Agricultural Technology and Innovation Research Institute, Kindai University, Nara, Japan

    Takashi Fukuda

Authors
  1. Kohei Ishida
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  2. Teruki Tanaka
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  3. Kenichiro Nagai
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  4. Yoshimasa Furuichi
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  5. Takeshi Terahara
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  6. Masashi Ando
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  7. Yasuyuki Tsukamasa
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  8. Takashi Fukuda
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Contributions

K.I., T.T., K.N., Y.F., T.T., M.A., Y.T., and T.F. designed research; K.I., T.T., K.N., Y.F., T.T., and T.F. performed research; K.I., T.T., K.N., Y.F., T.T., and T.F. contributed new reagents/analytic tools; K.I., T.T., K.N., Y.F., T.T., M.A., Y.T., and T.F. analyzed data; and K.I., T.T., K.N., Y.F., T.T., and T.F. wrote the paper.

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Correspondence to Takashi Fukuda.

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

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  • DOI: https://doi.org/10.1038/s41429-021-00484-5

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