title: Sharkquinone, a new ana-quinonoid tetracene derivative from marine-derived Streptomyces sp. EGY1 with TRAIL resistance-overcoming activity.
abstract: 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 μM in human gastric adenocarcinoma (AGS) cells.
authors.affiliation: Marine Natural Products Unit (MNPRU), Faculty of Science, Helwan University, Ain Helwan, Cairo, 11795, Egypt. mabdelfattah@science.helwan.edu.eg.|Chemistry Department, Faculty of Science, Helwan University, Ain Helwan, Cairo, 11795, Egypt. mabdelfattah@science.helwan.edu.eg.
authors.forename: Mohamed S
authors.initials: MS
authors.lastname: Abdelfattah
authors.affiliation: Marine Natural Products Unit (MNPRU), Faculty of Science, Helwan University, Ain Helwan, Cairo, 11795, Egypt.|Chemistry Department, Faculty of Science, Helwan University, Ain Helwan, Cairo, 11795, Egypt.
authors.forename: Mohammed I Y
authors.initials: MIY
authors.lastname: Elmallah
authors.affiliation: Chemistry Department, Faculty of Science, Helwan University, Ain Helwan, Cairo, 11795, Egypt.
authors.forename: Adal A
authors.initials: AA
authors.lastname: Mohamed
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba, 260-8675, Japan.
authors.forename: Masami
authors.initials: M
authors.lastname: Ishibashi
mesh_terms: D006801:Humans; D000230:Adenocarcinoma / Q000378:metabolism; D059001:Aquatic Organisms; D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D004534:Egypt; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009279:Naphthacenes; D011809:Quinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013274:Stomach Neoplasms / Q000378:metabolism; D013302:Streptomyces / Q000737:chemistry; D053221:TNF-Related Apoptosis-Inducing Ligand / Q000378:metabolism
chemical_list: D001688:Biological Products; C487736:naphthacene; D009279:Naphthacenes; D011809:Quinones; C000625117:sharkquinone; D053221:TNF-Related Apoptosis-Inducing Ligand
keywords: Actinomycetes; Spectroscopy; TRAIL; ana-Quinonoid