Swinhoeisterols from the South China Sea Sponge Theonella swinhoei

被引：23
作者：
Li, Jiao [1 ]
Tang, Hua [1 ]
Kurtan, Tibor [2 ]
Mandi, Attila [2 ]
Zhuang, Chun-Lin [1 ]
Su, Li [1 ]
Zheng, Gui-Liang [3 ]
Zhang, Wen [1 ]
机构：
[1] Second Mil Med Univ, Sch Pharm, 325 Guo He Rd, Shanghai 200433, Peoples R China
[2] Univ Debrecen, Dept Organ Chem, POB 400, H-4002 Debrecen, Hungary
[3] Shanghai Jiao Tong Univ, Sch Med, Xinhua Hosp, Dept Otorhinolaryngol Head & Neck Surg, 1665 Kong Jiang Rd, Shanghai 200092, Peoples R China
来源：
JOURNAL OF NATURAL PRODUCTS | 2018年 / 81卷 / 07期
关键词：
CYCLIC PENTAPEPTIDES; A-C; INHIBITORS; ACETYLTRANSFERASE; P300; 4-METHYLENESTEROLS; CBP/P300;
D O I：
10.1021/acs.jnatprod.8b00281
中图分类号：
Q94 [植物学];
学科分类号：
071001 ;
摘要：
Swinhoeisterols C-F (1-4), four new steroids having a rearranged 6/6/5/7 ring system, were isolated from the Xisha sponge Theonella swinhoei, together with the known analogue swinhoeisterol A (5). Their structures were determined based on spectroscopic analysis, TDDFT-ECD and optical rotation calculations, and biogenetic correlations. In an in vitro assay, compound 1 showed an inhibitory effect on (h)p300 with an IC50 value of 8.8 mu M, whereas compounds 2-4 were not active.
引用
收藏
页码：1645 / 1650
页数：6
相关论文
共 38 条
  • [1] [Anonymous], 2015, MACROMODEL
  • [2] Curcumin, a novel p300/CREB-binding protein-specific inhibitor of acetyltransferase, represses the acetylation of histone/nonhistone proteins and histone acetyltransferase-dependent chromatin transcription
    Balasubramanyam, K
    Varier, RA
    Altaf, M
    Swaminathan, V
    Siddappa, NB
    Ranga, U
    Kundu, TK
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (49) : 51163 - 51171
  • [3] 4-Methylenesterols from Theonella swinhoei sponge are natural pregnane-X-receptor agonists and farnesoid-X-receptor antagonists that modulate innate immunity
    De Marino, Simona
    Ummarino, Raffaella
    D'Auria, Maria Valeria
    Chini, Maria Giovanna
    Bifulco, Giuseppe
    D'Amore, Claudio
    Renga, Barbara
    Mencarelli, Andrea
    Petek, Sylvain
    Fiorucci, Stefano
    Zampella, Angela
    [J]. STEROIDS, 2012, 77 (05) : 484 - 495
  • [4] Theonellasterols and Conicasterols from Theonella swinhoei. Novel Marine Natural Ligands for Human Nuclear Receptors
    De Marino, Simona
    Ummarino, Raffaella
    D'Auria, Maria Valeria
    Chini, Maria Giovanna
    Bifulco, Giuseppe
    Renga, Barbara
    D'Amore, Claudio
    Fiorucci, Stefano
    Debitus, Cecile
    Zampella, Angela
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (08) : 3065 - 3075
  • [5] PYRIDINE-INDUCED SOLVENT SHIFTS IN NUCLEAR MAGNETIC RESONANCE SPECTRA OF HYDROXYLIC COMPOUNDS
    DEMARCO, PV
    FARKAS, E
    DODDRELL, D
    MYLARI, BL
    WENKERT, E
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) : 5480 - &
  • [6] Anti-inflammatory cyclopeptides from the marine sponge Theonella swinhoei
    Festa, Carmen
    De Marino, Simona
    D'Auria, Maria Valeria
    Monti, Maria Chiara
    Bucci, Mariarosaria
    Vellecco, Valentina
    Debitus, Cecile
    Zampella, Angela
    [J]. TETRAHEDRON, 2012, 68 (13) : 2851 - 2857
  • [7] Frisch, 2016, GAUSSIAN 16 REVISION
  • [8] Nazumazoles D-F, Cyclic Pentapeptides That Inhibit Chymotrypsin, from the Marine Sponge Theonella swinhoei
    Fukuhara, Kazuya
    Takada, Kentaro
    Okada, Shigeru
    Matsunaga, Shigeki
    [J]. JOURNAL OF NATURAL PRODUCTS, 2016, 79 (06): : 1694 - 1697
  • [9] Nazumazoles A-C, Cyclic Pentapeptides Dimerized through a Disulfide Bond from the Marine Sponge Theonella swinhoei
    Fukuhara, Kazuya
    Takada, Kentaro
    Okada, Shigeru
    Matsunaga, Shigeki
    [J]. ORGANIC LETTERS, 2015, 17 (11) : 2646 - 2648
  • [10] A Histone Acetyltransferase p300 Inhibitor C646 Induces Cell Cycle Arrest and Apoptosis Selectively in AML1-ETO-Positive AML Cells
    Gao, Xiao-ning
    Lin, Ji
    Ning, Qiao-yang
    Gao, Li
    Yao, Yu-shi
    Zhou, Ji-hao
    Li, Yong-hui
    Wang, Li-li
    Yu, Li
    [J]. PLOS ONE, 2013, 8 (02):
1234