Tripartin, a Histone Demethylase Inhibitor from a Bacterium Associated with a Dung Beetle Larva

被引:80
作者
Kim, Seong-Hwan [1 ]
Kwon, So Hee [2 ]
Park, Seon-Hui [1 ]
Lee, Jae Kyun [3 ]
Bang, Hea-Son [4 ]
Nam, Sang-Jip [5 ]
Kwon, Hak Cheol [6 ]
Shin, Jongheon [1 ]
Oh, Dong-Chan [1 ]
机构
[1] Seoul Natl Univ, Coll Pharm, Inst Nat Prod Res, Seoul 151742, South Korea
[2] Yonsei Univ, Coll Pharm, Yonsei Inst Pharmaceut Sci, Inchon 406840, South Korea
[3] Korea Inst Sci & Technol, Neuromed Ctr, Seoul 130650, South Korea
[4] Natl Acad Agr Sci, Agr Environm Dept, Suwon 441707, South Korea
[5] Ewha Womans Univ, Dept Chem & Nano Sci, Seoul 120750, South Korea
[6] Korea Inst Sci & Technol, Nat Prod Res Ctr, Kangnung 210340, Gangwon Do, South Korea
基金
新加坡国家研究基金会;
关键词
BIOSYNTHESIS; MEDIATOR; HYPOXIA;
D O I
10.1021/ol4004417
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tripartin (1), a new dichlorinated indanone, was isolated from the culture broth of the Streptomyces sp. associated with a larva of the dung beetle Copris tripartitus Waterhouse. The planar structure of tripartin (1) was identified by the spectroscopic analyses of NMR, mass, UV, and IR data. The structure was confirmed, and the absolute configuration of 1 was determined by X-ray crystallography. Tripartin displayed specific activity as an inhibitor of the histone H3 lysine 9 demethylase KDM4 in HeLa cells.
引用
收藏
页码:1834 / 1837
页数:4
相关论文
共 33 条
[11]   Actinotetraoses A-H: Tetrasaccharide Derivatives from a Grasshopper-Associated Amycolatopsis sp HCa1 [J].
Guo, Zhi Kai ;
Zhang, Gao Fei ;
Jiao, Rui Hua ;
Shen, Yan ;
Xu, Qiang ;
Tan, Ren Xiang ;
Ge, Hui Ming .
PLANTA MEDICA, 2012, 78 (10) :988-994
[12]   Design, Synthesis, Enzyme-Inhibitory Activity, and Effect on Human Cancer Cells of a Novel Series of Jumonji Domain-Containing Protein 2 Histone Demethylase Inhibitors [J].
Hamada, Shohei ;
Suzuki, Takayoshi ;
Mino, Koshiki ;
Kosek, Koichi ;
Oehme, Felix ;
Flamme, Ingo ;
Ozasa, Hiroki ;
Itoh, Yukihiro ;
Ogasawara, Daisuke ;
Komaarashi, Haruka ;
Kato, Aiko ;
Tsumoto, Hiroki ;
Nakagawa, Hidehiko ;
Hasegawa, Makoto ;
Sasaki, Ryuzo ;
Mizukami, Tamio ;
Miyata, Naoki .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (15) :5629-5638
[13]   KDM2b/JHDM1b, an H3K36me2-specific demethylase, is required for initiation and maintenance of acute myeloid leukemia [J].
He, Jin ;
Anh Tram Nguyen ;
Zhang, Yi .
BLOOD, 2011, 117 (14) :3869-3880
[14]   Coprismycins A and B, neuroprotective phenylpyridines from the dung beetle-associated bacterium, Streptomyces sp. [J].
Kim, Seong-Hwan ;
Ko, Hyeonseok ;
Bang, Hea-Son ;
Park, Seon-Hui ;
Kim, Dong-Gyu ;
Kwon, Hak Cheol ;
Kim, Sun Yeou ;
Shin, Jongheon ;
Oh, Dong-Chan .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (19) :5715-5718
[15]  
KUROYANAGI M, 1974, CHEM PHARM BULL, V22, P2762
[16]   A Selective Inhibitor and Probe of the Cellular Functions of Jumonji C Domain-Containing Histone Demethylases [J].
Luo, Xuelai ;
Liu, Yongxiang ;
Kubicek, Stefan ;
Myllyharju, Johanna ;
Tumber, Anthony ;
Ng, Stanley ;
Che, Ka Hing ;
Podoll, Jessica ;
Heightman, Tom D. ;
Oppermann, Udo ;
Schreiber, Stuart L. ;
Wang, Xiang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (24) :9451-9456
[17]   The diverse functions of histone lysine methylation [J].
Martin, C ;
Zhang, Y .
NATURE REVIEWS MOLECULAR CELL BIOLOGY, 2005, 6 (11) :838-849
[18]   A new indanone from the marine cyanobacterium Lyngbya majuscula that inhibits hypoxia-induced activation of the VEGF promoter in Hep3B cells [J].
Nagle, DG ;
Zhou, YD ;
Park, PU ;
Paul, VJ ;
Rajbhandari, I ;
Duncan, CJG ;
Pasco, DS .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (10) :1431-1433
[19]   An ecological perspective of microbial secondary metabolism [J].
O'Brien, Jonathan ;
Wright, Gerard D. .
CURRENT OPINION IN BIOTECHNOLOGY, 2011, 22 (04) :552-558
[20]   Sceliphrolactam, a Polyene Macrocyclic Lactam from a Wasp-Associated Streptomyces sp. [J].
Oh, Dong-Chan ;
Poulsen, Michael ;
Currie, Cameron R. ;
Clardy, Jon .
ORGANIC LETTERS, 2011, 13 (04) :752-755