title: Antibiotic and cytotoxic activity of brominated compounds from the marine sponge Verongia aerophoba.
abstract: Analysis of the marine sponge Verongia aerophoba from the Canary Islands afforded eight brominated secondary metabolites including the small molecular weight compounds aeroplysinin-1 (5) and the dienone (7) which were previously shown to arise by enzymatically catalyzed degradation of aerophobin-2 (4) and isofistularin-3 (1) following breakdown of the cellular compartmentation of the sponge. All compounds were identified from their NMR and mass spectra. Aeroplysinin-1 as well as dienone which arise from isofistularin-3 or aerophobin-2 by biotransformation within the sponge showed a significantly higher antibiotic as well as cytotoxic activity than their biogenetic precursors. Antibiotic activity was studied with respect to several gram-positive and gram-negative bacteria including B. subtilis, S. aureus and E. coli. The MICs (MBCs) of aeroplysinin-1 (5) and the dienone (7) varied between 12.5-25 (50-100) micrograms/ml respectively. Cytotoxicity was tested in vitro towards HeLa cells, a human cervix uteri tumour cell line. Aeroplysinin-1 (5) and the dienone (7) displayed pronounced cytotoxic activity with IC50s of 3.0 and 3.2 microM respectively. A five-fold increase in cytotoxicity was observed after O-acetylation of the dienone (7). The IC50 of the dienone O-acetate (0.6 microM) was comparable to that of the clinically used anticancer drug cisplatin (0.7 microM).
authors.affiliation: Julius-von-Sachs-Institut für Biowissenschaften, Lehrstuhl für Pharmazeutische Biologie, Universität Würzburg, Bundesrepublik Deutschland.
authors.forename: R
authors.initials: R
authors.lastname: Teeyapant
authors.forename: H J
authors.initials: HJ
authors.lastname: Woerdenbag
authors.forename: P
authors.initials: P
authors.lastname: Kreis
authors.forename: J
authors.initials: J
authors.lastname: Hacker
authors.forename: V
authors.initials: V
authors.lastname: Wray
authors.forename: L
authors.initials: L
authors.lastname: Witte
authors.forename: P
authors.initials: P
authors.lastname: Proksch
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000302:isolation & purification* / Q000633:toxicity; D000970:Antineoplastic Agents / Q000302:isolation & purification* / Q000633:toxicity; D002470:Cell Survival / Q000187:drug effects*; D002851:Chromatography, High Pressure Liquid; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006367:HeLa Cells; D006801:Humans; D006842:Hydrocarbons, Brominated / Q000302:isolation & purification* / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011161:Porifera; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D006842:Hydrocarbons, Brominated