Sharkquinone, a new ana-quinonoid tetracene derivative from marine-derived Streptomyces sp EGY1 with TRAIL resistance-overcoming activity

被引:8
作者
Abdelfattah, Mohamed S. [1 ,2 ]
Elmallah, Mohammed I. Y. [1 ,2 ]
Mohamed, Adal A. [2 ]
Ishibashi, Masami [3 ]
机构
[1] Helwan Univ, Fac Sci, Marine Nat Prod Unit MNPRU, Cairo 11795, Egypt
[2] Helwan Univ, Fac Sci, Chem Dept, Cairo 11795, Egypt
[3] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan
关键词
Actinomycetes; ana-Quinonoid; Spectroscopy; TRAIL; C-13; NMR-SPECTRA; SP IFM 11307; UP-REGULATION; APOPTOSIS; METABOLITES; MECHANISMS; ALKALOIDS;
D O I
10.1007/s11418-017-1086-5
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A new ana-quinonoid tetracene metabolite, named sharkquinone (1), and the known SS-228R (2) have been isolated from the ethyl acetate extract of the culture of marine Streptomyces sp. EGY1. The strain was isolated from sediment sample collected from the Red Sea coast of Egypt. The structure of sharkquinone (1) was elucidated using detailed spectral (HRESI-MS, 1D and 2D NMR) analyses and quantum chemical calculations. This is the first report of the isolation of ana-quinonoid tetracene derivative from a natural source. Compound 1 showed the ability to overcome tumor necrosis factor-related apoptosis- inducing ligand (TRAIL) resistance at a concentration of 10 mu M in human gastric adenocarcinoma (AGS) cells.
引用
收藏
页码:564 / 569
页数:6
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