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The Journal of Antibiotics
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Isolation and structure elucidation of a novel androgen antagonist, arabilin, produced byStreptomyces sp. MK756-CF1

The Journal of Antibioticsvolume 63, pages601–605 (2010)Cite this article

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Abstract

In the course of screening for a new type of androgen receptor (AR) antagonist, we isolated a novel compound, arabilin, with two structural isomers, spectinabilin and SNF4435C, produced byStreptomyces sp. MK756-CF1. Structure elucidation on the basis of the spectroscopic properties showed that arabilin is a novel polypropionate-derived metabolite with ap-nitrophenyl group and a substituted γ-pyrone ring. Arabilin competitively blocked the binding of androgen to the ligand-binding domain of ARin vitro. In addition, arabilin inhibited androgen-induced prostate-specific antigen mRNA expression in prostate cancer LNCaP cells.

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Acknowledgements

This study was partly supported by grants from the Ministry of Education, Culture, Sports, Science and Technology of Japan.

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Author notes

  1. Tatsuro Kawamura and Takahiro Fujimaki: These authors contributed equally to this work.

Authors and Affiliations

  1. Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University, Yokohama, Japan

    Tatsuro Kawamura, Takahiro Fujimaki, Natsuki Hamanaka, Kentaro Torii, Hiroki Kobayashi, Etsu Tashiro & Masaya Imoto

  2. Institute of Microbial Chemistry, Tokyo, Japan

    Yoshikazu Takahashi, Masayuki Igarashi, Naoko Kinoshita & Yoshio Nishimura

Authors
  1. Tatsuro Kawamura
  2. Takahiro Fujimaki
  3. Natsuki Hamanaka
  4. Kentaro Torii
  5. Hiroki Kobayashi
  6. Yoshikazu Takahashi
  7. Masayuki Igarashi
  8. Naoko Kinoshita
  9. Yoshio Nishimura
  10. Etsu Tashiro
  11. Masaya Imoto

Corresponding author

Correspondence toMasaya Imoto.

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Kawamura, T., Fujimaki, T., Hamanaka, N.et al. Isolation and structure elucidation of a novel androgen antagonist, arabilin, produced byStreptomyces sp. MK756-CF1.J Antibiot63, 601–605 (2010). https://doi.org/10.1038/ja.2010.98

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