Creation of an HDAC-Based Yeast Screening Method for Evaluation of Marine-Derived Actinomycetes: Discovery of Streptosetin A

被引:16
作者
Amagata, Taro [1 ]
Xiao, Jing [1 ]
Chen, Yi-Pei [1 ]
Holsopple, Nicholas [1 ]
Oliver, Allen G. [2 ]
Gokey, Trevor [1 ]
Guliaev, Anton B. [1 ]
Minoura, Katsuhiko [3 ]
机构
[1] San Francisco State Univ, Dept Chem & Biochem, San Francisco, CA 94132 USA
[2] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA
[3] Osaka Univ Pharmaceut Sci, Takatsuki, Osaka 5691094, Japan
来源
JOURNAL OF NATURAL PRODUCTS | 2012年 / 75卷 / 12期
关键词
ELECTRONIC CIRCULAR-DICHROISM; ABSOLUTE-CONFIGURATION; INHIBITORS; SIRT2; IDENTIFICATION; BIOSYNTHESIS; METABOLITE; EQUISETIN; FAMILY; CANCER;
D O I
10.1021/np300640g
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
A histone deacetylase (HDAC)-based yeast assay employing a URA3 reporter gene was applied as a primary screen to evaluate a marine-derived actinomycete extract library and identify human class III HDAC (SIRT) inhibitors. On the basis of the bioassay-guided purification, a new compound designated as streptosetin A (1) was obtained from one of the active strains identified through the yeast assay. The gross structure of the new compound was elucidated from the ID and 2D NMR data. The absolute stereostructure of 1 was determined based on X-ray crystal structure analysis and simulation of ECD spectra using time-dependent density functional theory calculations. This compound showed weak inhibitory activity against yeast Sir2p and human SIRT1 and SIRT2.
引用
收藏
页码:2193 / 2199
页数:7
相关论文
共 32 条
  • [1] [Anonymous], 2010, BRUK APEX 2 V2010 7
  • [2] Identification of a small molecule inhibitor of Sir2p
    Bedalov, A
    Gatbonton, T
    Irvine, WP
    Gottschling, DE
    Simon, JA
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2001, 98 (26) : 15113 - 15118
  • [3] THE SIR2 GENE FAMILY, CONSERVED FROM BACTERIA TO HUMANS, FUNCTIONS IN SILENCING, CELL-CYCLE PROGRESSION, AND CHROMOSOME STABILITY
    BRACHMANN, CB
    SHERMAN, JM
    DEVINE, SE
    CAMERON, EE
    PILLUS, L
    BOEKE, JD
    [J]. GENES & DEVELOPMENT, 1995, 9 (23) : 2888 - 2902
  • [4] ON ENANTIOMORPH-POLARITY ESTIMATION
    FLACK, HD
    [J]. ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV): : 876 - 881
  • [5] Frisch M. J., 2016, Gaussian 03 Revision B.03
  • [6] Phylogenetic classification of prokaryotic and eukaryotic Sir2-like proteins
    Frye, RA
    [J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2000, 273 (02) : 793 - 798
  • [7] Phloroglucinol derivatives guttiferone G, aristoforin, and hyperforin:: Inhibitors of human sirtuins SIRT1 and SIRT2
    Gey, Claudia
    Kyrylenko, Sergiy
    Hennig, Lothar
    Nguyen, Lien-Hoa D.
    Buettner, Anita
    Pham, Hung D.
    Giannis, Athanassios
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (27) : 5219 - 5222
  • [8] Identification of a class of small molecule inhibitors of the sirtuin family of NAD-dependent deacetylases by phenotypic screening
    Grozinger, CM
    Chao, ED
    Blackwell, HE
    Moazed, D
    Schreiber, SL
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (42) : 38837 - 38843
  • [9] Structural and Synthetic Investigations of Tanikolide Dimer, a SIRT2 Selective Inhibitor, and Tanikolide seco-Acid from the Madagascar Marine Cyanobacterium Lyngbya majuscula
    Gutierrez, Marcelino
    Andrianasolo, Eric H.
    Shin, Won Kyo
    Goeger, Douglas E.
    Yokochi, Alexandre
    Schemies, Joerg
    Jung, Manfred
    France, Dennis
    Cornell-Kennon, Susan
    Lee, Eun
    Gerwick, William H.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) : 5267 - 5275
  • [10] A chemical epigenetics approach for engineering the in situ biosynthesis of a cryptic natural product from Aspergillus niger
    Henrikson, Jon C.
    Hoover, Ashley R.
    Joyner, P. Matthew
    Cichewicz, Robert H.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (03) : 435 - 438