Micromide and guamamide: cytotoxic alkaloids from a species of the marine cyanobacterium Symploca.
Two new cytotoxins have been isolated from a species of marine cyanobacterium belonging to the genus Symploca that was collected in Guam. These new compounds, micromide (1) and guamamide (2), were accompanied by the known lipopeptides apramides A (3), B (4), and G (5). The planar structures of both alkaloids were elucidated by standard 2D NMR techniques, and the configurations of the amino acid-derived units in 1 were determined by chiral HPLC. The stereochemistry of the beta-methoxyhexanoic acid in 1 was determined by derivatization with methyl d-mandelate, after acid hydrolysis, and comparison with synthetic standards.
Williams
Philip G
PG
Department of Chemistry, University of Hawaii at Manoa, Honolulu, HI 96822, USA.
Yoshida
Wesley Y
WY
Moore
Richard E
RE
Paul
Valerie J
VJ
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002851:Chromatography, High Pressure Liquid; D000458:Cyanobacteria / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D006141:Guam; D006801:Humans; D020128:Inhibitory Concentration 50; D007624:KB Cells; D008074:Lipoproteins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009842:Oligopeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism
D000470:Alkaloids; D008074:Lipoproteins; D009842:Oligopeptides; C483003:apramide A; C483004:apramide B; C483005:apramide G; C483002:guamamide; C483001:micromide