Activation of the Nuclear Factor E2-Related Factor 2 Pathway by Novel Natural Products Halomadurones A-D and a Synthetic Analogue

被引：19
作者：
Wyche, Thomas P. [1 ]
Standiford, Miranda [1 ]
Hou, Yanpeng [1 ]
Braun, Doug [1 ]
Johnson, Delinda A. [1 ]
Johnson, Jeffrey A. [1 ]
Bugni, Tim S. [1 ]
机构：
[1] Univ Wisconsin, Div Pharmaceut Sci, Madison, WI 53705 USA
来源：
MARINE DRUGS | 2013年 / 11卷 / 12期
关键词：
Ecteinascidia turbinata; halomadurones; Actinomadura; nuclear factor E2-related factor antioxidant response element; CYANOBACTERIUM LYNGBYA-MAJUSCULA; ANTIOXIDANT RESPONSE ELEMENT; STREPTOMYCES-CARZINOSTATICUS; NEURODEGENERATIVE DISEASE; NRF2-ARE PATHWAY; OXIDATIVE STRESS; HEME OXYGENASE-1; NEOCARZILIN-A; GENE; BIOSYNTHESIS;
D O I：
10.3390/md11125089
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Two novel chlorinated pyrones, halomadurones A and B, and two novel brominated analogues, halomadurones C and D, were isolated from a marine Actinomadura sp. cultivated from the ascidian Ecteinascidia turbinata. Additionally, a non-halogenated analogue, 2-methyl-6-((E)-3-methyl-1,3-hexadiene)--pyrone, was synthesized to understand the role of the halogens for activity. Halomadurones C and D demonstrated potent nuclear factor E2-related factor antioxidant response element (Nrf2-ARE) activation, which is an important therapeutic approach for treatment of neurodegenerative diseases.
引用
收藏
页码：5089 / 5099
页数：11
相关论文
共 32 条
  • [1] Curcurnin activates the haem oxygenase-1 gene via regulation of Nrf2 and the antioxidant-responsive element
    Balogun, E
    Hoque, M
    Gong, PF
    Killeen, E
    Green, CJ
    Foresti, R
    Alam, J
    Motterlini, R
    [J]. BIOCHEMICAL JOURNAL, 2003, 371 : 887 - 895
  • [2] Calkins MJ, 2009, ANTIOXID REDOX SIGN, V11, P497, DOI 10.1089/ARS.2008.2242
  • [3] Nrf2-induced antioxidant Protection: A Promising target to counteract ROS-mediated damage in neurodegenerative disease?
    de Vries, Helga E.
    Witte, Maarten
    Hondius, David
    Rozermuller, Annemieke J. M.
    Drukarch, Benjamin
    Hoozemans, Jeroen
    van Horssen, Jack
    [J]. FREE RADICAL BIOLOGY AND MEDICINE, 2008, 45 (10) : 1375 - 1383
  • [4] Discovery and characterization of a marine bacterial SAM-dependent chlorinase
    Eustaquio, Alessandra S.
    Pojer, Florence
    Noel, Joseph P.
    Moore, Bradley S.
    [J]. NATURE CHEMICAL BIOLOGY, 2008, 4 (01) : 69 - 74
  • [5] Structure activity relationship of phenolic diterpenes from Salvia officinalis as activators of the nuclear factor E2-related factor 2 pathway
    Fischedick, Justin T.
    Standiford, Miranda
    Johnson, Delinda A.
    Johnson, Jeffrey A.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (09) : 2618 - 2622
  • [6] A novel method for the synthesis of formyl and hydroxymethyl derivatives of 4H-pyran-4-one
    Ghandi, M
    Bayat, Y
    Teimuri-mofrad, R
    [J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2002, 34 (05) : 525 - 530
  • [7] Triterpenoid electrophiles (avicins) activate the innate stress response by redox regulation of a gene battery
    Haridas, V
    Hanausek, M
    Nishimura, G
    Soehnge, H
    Gaikwad, A
    Narog, M
    Spears, E
    Zoltaszek, R
    Walaszek, Z
    Gutterman, JU
    [J]. JOURNAL OF CLINICAL INVESTIGATION, 2004, 113 (01) : 65 - 73
  • [8] Alzheimer disease in the United States (2010-2050) estimated using the 2010 census
    Hebert, Liesi E.
    Weuve, Jennifer
    Scherr, Paul A.
    Evans, Denis A.
    [J]. NEUROLOGY, 2013, 80 (19) : 1778 - 1783
  • [9] Microbial Strain Prioritization Using Metabolomics Tools for the Discovery of Natural Products
    Hou, Yanpeng
    Braun, Doug R.
    Michel, Cole R.
    Klassen, Jonathan L.
    Adnani, Navid
    Wyche, Thomas P.
    Bugni, Tim S.
    [J]. ANALYTICAL CHEMISTRY, 2012, 84 (10) : 4277 - 4283
  • [10] Regulatory mechanisms of cellular response to oxidative stress
    Itoh, K
    Ishii, T
    Wakabayashi, N
    Yamamoto, M
    [J]. FREE RADICAL RESEARCH, 1999, 31 (04) : 319 - 324
1234