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

被引:19
|
作者
Kawamura, Tatsuro
Fujimaki, Takahiro
Hamanaka, Natsuki
Torii, Kentaro
Kobayashi, Hiroki
Takahashi, Yoshikazu [2 ]
Igarashi, Masayuki [2 ]
Kinoshita, Naoko [2 ]
Nishimura, Yoshio [2 ]
Tashiro, Etsu
Imoto, Masaya [1 ]
机构
[1] Keio Univ, Dept Biosci & Informat, Fac Sci & Technol, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
[2] Inst Microbial Chem, Tokyo 141, Japan
来源
JOURNAL OF ANTIBIOTICS | 2010年 / 63卷 / 10期
关键词
androgen antagonist; prostate cancer PSA; PROSTATE-CANCER; SNF4435C; RECEPTOR; SPECTINABILIN; SPECTABILIS; STRAIN;
D O I
10.1038/ja.2010.98
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
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 gamma 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 The Journal of Antibiotics (2010) 63, 601-605, doi 10 1038/ja 2010 98, published online 25 August 2010
引用
收藏
页码:601 / 605
页数:5
相关论文
共 50 条
  • [21] Naphthacemycins, novel circumventors of β-lactam resistance in MRSA, produced by Streptomyces sp. KB-3346-5. II. Structure elucidation
    Atsushi Fukumoto
    Yong-Pil Kim
    Masato Iwatsuki
    Tomoyasu Hirose
    Toshiaki Sunazuka
    Hideaki Hanaki
    Satoshi Ōmura
    Kazuro Shiomi
    The Journal of Antibiotics, 2017, 70 : 568 - 573
  • [23] Guignardic acid, a novel type of secondary metabolite produced by the endophytic fungus Guignardia sp.:: Isolation, structure elucidation, and asymmetric synthesis
    Rodrigues-Heerklotz, KF
    Drandarov, K
    Heerklotz, J
    Hesse, M
    Werner, C
    HELVETICA CHIMICA ACTA, 2001, 84 (12) : 3766 - 3772
  • [24] GUALAMYCIN, A NOVEL ACARICIDE PRODUCED BY STREPTOMYCES SP NK11687 .1. TAXONOMY, PRODUCTION, ISOLATION, AND PRELIMINARY CHARACTERIZATION
    TSUCHIYA, K
    KOBAYASHI, S
    HARADA, T
    KUROKAWA, T
    NAKAGAWA, T
    SHIMADA, N
    KOBAYASHI, K
    JOURNAL OF ANTIBIOTICS, 1995, 48 (07): : 626 - 629
  • [25] Cyclipostins, novel hormone-sensitive lipase inhibitors from Streptomyces sp DSM 13381 -: II.: Isolation, structure elucidation and biological properties
    Vértesy, L
    Beck, B
    Brönstrup, M
    Ehrlich, K
    Kurz, M
    Müller, G
    Schummer, D
    Seibert, G
    JOURNAL OF ANTIBIOTICS, 2002, 55 (05): : 480 - 494
  • [26] TMC-1 A, B, C and D, new antibiotics of the manumycin group produced by Streptomyces sp - Taxonomy, production, isolation, physico-chemical properties, structure elucidation and biological properties
    Kohno, J
    Nishio, M
    Kawano, K
    Nakanishi, N
    Suzuki, S
    Uchida, T
    Komatsubara, S
    JOURNAL OF ANTIBIOTICS, 1996, 49 (12): : 1212 - 1220
  • [27] Spirodionic acid, a novel metabolite from Streptomyces sp., part 1:: Structure elucidation and Diels-Alder-type biosynthesis
    Textor, Adriana
    Papastavrou, Ina
    Siewert, Juergen
    Magull, Joerg
    Kulik, Andreas
    Fiedler, Mans-Peter
    von Zezschwitz, Paultheo
    Grond, Stephanie
    CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (26) : 7416 - 7423
  • [28] Fattiviracin A1, a novel antiherpetic agent produced by Streptomyces microflavus strain no. 2445 -: I.: Taxonomy, fermentation, isolation, physico-chemical properties and structure elucidation
    Uyeda, M
    Yokomizo, K
    Miyamoto, Y
    Habib, ESE
    JOURNAL OF ANTIBIOTICS, 1998, 51 (09): : 823 - 828
  • [29] TETRONOTHIODIN, A NOVEL CHOLECYSTOKININ TYPE-B RECEPTOR ANTAGONIST PRODUCED BY STREPTOMYCES SP-NR0489 .2. ISOLATION, CHARACTERIZATION AND BIOLOGICAL-ACTIVITIES
    OHTSUKA, T
    KOTAKI, H
    NAKAYAMA, N
    ITEZONO, Y
    SHIMMA, N
    KUDOH, T
    KUWAHARA, T
    ARISAWA, M
    YOKOSE, K
    SETO, H
    JOURNAL OF ANTIBIOTICS, 1993, 46 (01): : 11 - 17
  • [30] Trierixin, a novel inhibitor of ER stress-induced XBP1 activation from Streptomyces sp -: II. structure elucidation
    Futamura, Yushi
    Tashiro, Etsu
    Hironiwa, Naoka
    Kohno, Jun
    Nishio, Maki
    Shindo, Kazutoshi
    Imoto, Masaya
    JOURNAL OF ANTIBIOTICS, 2007, 60 (09): : 582 - 585