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

doi:10.1038/ja.2010.98

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 journal › Article › peer-review

19 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 language	English
Pages (from-to)	601-605
Number of pages	5
Journal	Journal of Antibiotics
Volume	63
Issue number	10
DOIs	https://doi.org/10.1038/ja.2010.98
Publication status	Published - 2010 Oct
Externally published	Yes

Keywords

Androgen antagonist
PSA
prostate cancer

ASJC Scopus subject areas

Pharmacology
Drug Discovery

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1038/ja.2010.98

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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, PSA, prostate cancer",

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",

note = "Funding Information: This study was partly supported by grants from the Ministry of Education, Culture, Sports, Science and Technology of Japan.",

year = "2010",

month = oct,

doi = "10.1038/ja.2010.98",

language = "English",

volume = "63",

pages = "601--605",

journal = "Journal of Antibiotics",

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publisher = "Japan Antibiotics Research Association",

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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

N1 - Funding Information: This study was partly supported by grants from the Ministry of Education, Culture, Sports, Science and Technology of Japan.

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 - PSA

KW - prostate cancer

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DO - 10.1038/ja.2010.98

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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