title: Bioactive secondary metabolites from the Red Sea marine Verongid sponge Suberea species.
abstract: In a continuation of our efforts to identify bioactive compounds from Red Sea Verongid sponges, the organic extract of the sponge Suberea species afforded seven compounds including two new dibrominated alkaloids, subereamollines C and D (1 and 2), together with the known compounds aerothionin (3), homoaerothionin (4), aeroplysinin-1 (5), aeroplysinin-2 (6) and a revised subereaphenol C (7) as ethyl 2-(2,4-dibromo-3,6-dihydroxyphenyl)acetate. The structures of the isolated compounds were assigned by different spectral data including optical rotations, 1D (1H and 13C) and 2D (COSY, multiplicity-edited HSQC, and HMBC) NMR and high-resolution mass spectroscopy. Aerothionin (3) and subereaphenol C (7) displayed potent cytotoxic activity against HeLa cell line with IC50 values of 29 and 13.3 µM, respectively. In addition, aeroplysinin-2 (6) showed potent antimigratory activity against the human breast cancer cell line MDA-MB-231 with IC50 of 18 µM. Subereamollines C and D are new congeners of the previously reported compounds subereamollines A and B with methyl ester functionalities on the side chain. These findings provide further insight into the biosynthetic capabilities of members of the genus Suberea and the chemical diversity as well as the biological activity of these compounds.
authors: Natural Products Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Saudi Arabia. lshalla@kau.edu.sa.|Suez Canal University Hospital, Suez Canal University, Ismailia 41522, Egypt. lshalla@kau.edu.sa.
authors: Lamiaa A
authors: LA
authors: Shaala
authors: Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia. dyoussef@kau.edu.sa.
authors: Diaa T A
authors: DT
authors: Youssef
authors: Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia. jibrahim@kau.edu.sa.|Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt. jibrahim@kau.edu.sa.
authors: Jihan M
authors: JM
authors: Badr
authors: Department of Pharmacology, Faculty of Medicine, King Abdulaziz University, Jeddah 21589, Saudi Arabia. misulaiman@kau.edu.sa.
authors: Mansour
authors: M
authors: Sulaiman
authors: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia. khedr1961@gmail.com.
authors: Alaa
authors: A
authors: Khedr
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001572:Benzofurans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001969:Bromobenzenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002465:Cell Movement / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects; D055808:Drug Discovery; D004534:Egypt; D006801:Humans; D006842:Hydrocarbons, Brominated / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006873:Hydroquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007555:Isoxazoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy; D009792:Oceans and Seas; D011161:Porifera / Q000737:chemistry* / Q000254:growth & development; D012529:Saudi Arabia; D064210:Secondary Metabolism; D021241:Spectrometry, Mass, Electrospray Ionization; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000970:Antineoplastic Agents; D001572:Benzofurans; D001969:Bromobenzenes; D006842:Hydrocarbons, Brominated; D006873:Hydroquinones; D007555:Isoxazoles; D013141:Spiro Compounds; C000603846:aeroplysinin-2; C000603844:aerothionin; C000603845:subereaphenol C