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

Research output: Contribution to journalArticle

14 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

Fingerprint

Androgen Antagonists
Streptomyces
Androgens
Androgen Receptor Antagonists
Pyrones
Androgen Receptors
Prostate-Specific Antigen
Prostatic Neoplasms
Ligands
Messenger RNA
arabilin

Keywords

  • Androgen antagonist
  • prostate cancer
  • PSA

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

Cite this

Isolation and structure elucidation of a novel androgen antagonist, arabilin, produced by Streptomyces sp. MK756-CF1. / Kawamura, Tatsuro; Fujimaki, Takahiro; Hamanaka, Natsuki; Torii, Kentaro; Kobayashi, Hiroki; Takahashi, Yoshikazu; Igarashi, Masayuki; Kinoshita, Naoko; Nishimura, Yoshio; Tashiro, Etsu; Imoto, Masaya.

In: Journal of Antibiotics, Vol. 63, No. 10, 10.2010, p. 601-605.

Research output: Contribution to journalArticle

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, vol. 63, no. 10, pp. 601-605. https://doi.org/10.1038/ja.2010.98
Kawamura, Tatsuro ; Fujimaki, Takahiro ; Hamanaka, Natsuki ; Torii, Kentaro ; Kobayashi, Hiroki ; Takahashi, Yoshikazu ; Igarashi, Masayuki ; Kinoshita, Naoko ; Nishimura, Yoshio ; Tashiro, Etsu ; Imoto, Masaya. / Isolation and structure elucidation of a novel androgen antagonist, arabilin, produced by Streptomyces sp. MK756-CF1. In: Journal of Antibiotics. 2010 ; Vol. 63, No. 10. pp. 601-605.
@article{b1790815534648898cf65041c48674fb,
title = "Isolation and structure elucidation of a novel androgen antagonist, arabilin, produced by Streptomyces sp. MK756-CF1",
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.",
keywords = "Androgen antagonist, prostate cancer, PSA",
author = "Tatsuro Kawamura and Takahiro Fujimaki and Natsuki Hamanaka and Kentaro Torii and Hiroki Kobayashi and Yoshikazu Takahashi and Masayuki Igarashi and Naoko Kinoshita and Yoshio Nishimura and Etsu Tashiro and Masaya Imoto",
year = "2010",
month = "10",
doi = "10.1038/ja.2010.98",
language = "English",
volume = "63",
pages = "601--605",
journal = "Journal of Antibiotics",
issn = "0021-8820",
publisher = "Japan Antibiotics Research Association",
number = "10",

}

TY - JOUR

T1 - Isolation and structure elucidation of a novel androgen antagonist, arabilin, produced by Streptomyces sp. MK756-CF1

AU - Kawamura, Tatsuro

AU - Fujimaki, Takahiro

AU - Hamanaka, Natsuki

AU - Torii, Kentaro

AU - Kobayashi, Hiroki

AU - Takahashi, Yoshikazu

AU - Igarashi, Masayuki

AU - Kinoshita, Naoko

AU - Nishimura, Yoshio

AU - Tashiro, Etsu

AU - Imoto, Masaya

PY - 2010/10

Y1 - 2010/10

N2 - 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.

AB - 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.

KW - Androgen antagonist

KW - prostate cancer

KW - PSA

UR - http://www.scopus.com/inward/record.url?scp=78049274216&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=78049274216&partnerID=8YFLogxK

U2 - 10.1038/ja.2010.98

DO - 10.1038/ja.2010.98

M3 - Article

VL - 63

SP - 601

EP - 605

JO - Journal of Antibiotics

JF - Journal of Antibiotics

SN - 0021-8820

IS - 10

ER -