Isolation and structure elucidation of a novel androgen antagonist, arabilin, produced by Streptomyces sp. MK756-CF1

Tatsuro Kawamura, Takahiro Fujimaki, Natsuki Hamanaka, Kentaro Torii, Hiroki Kobayashi, Yoshikazu Takahashi, Masayuki Igarashi, Naoko Kinoshita, Yoshio Nishimura, Etsu Tashiro, Masaya Imoto

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15 Citations (Scopus)

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 by Streptomyces sp. MK756-CF1. Structure elucidation on the basis of the spectroscopic properties showed that arabilin is a novel polypropionate-derived metabolite with a p-nitrophenyl group and a substituted γ-pyrone ring. Arabilin competitively blocked the binding of androgen to the ligand-binding domain of AR in vitro. In addition, arabilin inhibited androgen-induced prostate-specific antigen mRNA expression in prostate cancer LNCaP cells.

Original languageEnglish
Pages (from-to)601-605
Number of pages5
JournalJournal of Antibiotics
Volume63
Issue number10
DOIs
Publication statusPublished - 2010 Oct 1

Keywords

  • Androgen antagonist
  • PSA
  • prostate cancer

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

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    Kawamura, T., Fujimaki, T., Hamanaka, N., Torii, K., Kobayashi, H., Takahashi, Y., Igarashi, M., Kinoshita, N., Nishimura, Y., Tashiro, E., & Imoto, M. (2010). Isolation and structure elucidation of a novel androgen antagonist, arabilin, produced by Streptomyces sp. MK756-CF1. Journal of Antibiotics, 63(10), 601-605. https://doi.org/10.1038/ja.2010.98