title: Cytotoxic bromoindole derivatives and terpenes from the Philippine marine sponge Smenospongia sp.
abstract: A detailed chemical analysis of a Philippine marine sponge Smenospongia sp. has been performed. This study yielded four new metabolites, 5-bromo-L-tryptophan (1), 5-bromoabrine (2), 5,6-dibromoabrine (3) and 5-bromoindole-3-acetic acid (4). The pyrroloiminoquinone alkaloid, makaluvamine O (5) as well as 5,6-dibromotryptamine (6), aureol (7) and furospinulosin 1 (8) were also isolated. Although 1 and 4 have been synthesized previously, this is the first report on the isolation of these compounds from a natural source. The furanosesterterpene furospinulosin 1 (8) was obtained for the first time from the genus Smenospongia. The structures of all compounds were established by spectroscopic methods (UV, IR, 1D and 2D NMR, MS, [alpha]D). The cytotoxic potential of 1-8 was evaluated in a panel of isogenic HCT-116 human colon tumor cell lines.
authors.affiliation: Department of Medicinal Chemistry, College of Pharmacy, University of Utah, Salt Lake City 84112, USA. dtasdemi@hacettepe.edu.tr
authors.forename: Deniz
authors.initials: D
authors.lastname: Tasdemir
authors.forename: Timothy S
authors.initials: TS
authors.lastname: Bugni
authors.forename: Gina C
authors.initials: GC
authors.lastname: Mangalindan
authors.forename: Gisela P
authors.initials: GP
authors.lastname: Concepción
authors.forename: Mary Kay
authors.initials: MK
authors.lastname: Harper
authors.forename: Chris M
authors.initials: CM
authors.lastname: Ireland
mesh_terms: D000818:Animals; D002470:Cell Survival / Q000187:drug effects*; D003603:Cytotoxins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D007211:Indoles / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D010679:Philippines; D011161:Porifera / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013729:Terpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D014020:Tissue Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D014407:Tumor Cells, Cultured
chemical_list: D003603:Cytotoxins; D007211:Indoles; D013729:Terpenes; D014020:Tissue Extracts