New and biologically active imidazole alkaloids from two sponges of the genus Leucetta.
Chemical investigation of two sponges, Leucetta chagosensis and Leucetta cf chagosensis, collected from the Great Barrier Reef and the Fiji Islands, respectively, has led to the isolation of three new imidazole alkaloids (1-3), along with the known compounds isonaamine B (4) and naamine A (5). The structures of the new compounds (1-3) were elucidated by employing spectroscopic techniques (NMR, MS, UV, and IR). The structures of the known compounds 4 and 5 were determined by comparison of their (1)H and (13)C NMR spectroscopic data with published values. Compounds 1 and 2 were found to be cytotoxic toward several tumor cell lines (GI(50) values ranged from 1.3 to 7.0 microg/mL).
Gross
Harald
H
Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, Germany.
Kehraus
Stefan
S
König
Gabriele M
GM
Woerheide
Gert
G
Wright
Anthony D
AD
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001315:Australia; D001410:Bacillus megaterium / Q000187:drug effects; D006528:Carcinoma, Hepatocellular; D002851:Chromatography, High Pressure Liquid; D004354:Drug Screening Assays, Antitumor; D004926:Escherichia coli / Q000187:drug effects; D005367:Fiji; D005658:Fungi / Q000187:drug effects; D054303:HIV Reverse Transcriptase / Q000187:drug effects; D006801:Humans; D007093:Imidazoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D008113:Liver Neoplasms; D013058:Mass Spectrometry; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D013274:Stomach Neoplasms; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000470:Alkaloids; D000970:Antineoplastic Agents; D007093:Imidazoles; C466598:isonaamidine E; C466602:isonaamine B; C466599:isonaamine C; C466603:naamine A; C466601:naamine E; D054303:HIV Reverse Transcriptase