A new cytotoxic calyculinamide derivative, geometricin A, from the Australian sponge Luffariella geometrica.
Geometricin A (1), together with the known compounds (7E,12E,18S,20Z)-variabilin (2), clathryimine A (3), tryptophol (4), and L-tryptophan, has been isolated from the methanol extract of the Australian sponge Luffariella geometrica. The structure of the new compound geometricin A (1) was elucidated by employing spectroscopic techniques (NMR, MS, UV, and IR) and by comparison of its NMR data with those of the calyculins and calyculinamides. Geometricin A (1) was found to be moderately cytotoxic toward the tumor cell lines HM02 and HEPG2 with GI50's of 1.7 and 2.8 microg/mL, respectively, and to have antialgal activity (growth inhibition zone 5 mm at the 50 microg level).
Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, D-53115 Bonn, Germany.
Stefan
S
Kehraus
Gabriele M
GM
König
Anthony D
AD
Wright
D000818:Animals; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001315:Australia; D001410:Bacillus megaterium / Q000187:drug effects; D001713:Biphenyl Compounds / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D004354:Drug Screening Assays, Antitumor; D004926:Escherichia coli / Q000187:drug effects; D056890:Eukaryota / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D054303:HIV Reverse Transcriptase / Q000378:metabolism; D006801:Humans; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D008113:Liver Neoplasms; D019860:Lymphocyte Specific Protein Tyrosine Kinase p56(lck) / Q000378:metabolism; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010080:Oxazoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry*; D011807:Quinolizines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013274:Stomach Neoplasms; D014407:Tumor Cells, Cultured / Q000187:drug effects; D036343:Pterocarpans; D000438:Alcohols
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D001713:Biphenyl Compounds; D005663:Furans; D054303:HIV Reverse Transcriptase; D007211:Indoles; D019860:Lymphocyte Specific Protein Tyrosine Kinase p56(lck); D010080:Oxazoles; D011807:Quinolizines; C465908:(7E,12E,18S,20Z)-variabilin; D036343:Pterocarpans; C465907:clathryimine A; C465906:geometricin A; C005949:tryptophol; D000438:Alcohols