Novel bromotyrosine alkaloids: inhibitors of mycothiol S-conjugate amidase.
[structure: see text] The novel alkaloids 1 and 4 were isolated from an Australian non-verongid sponge, Oceanapia sp. Compound 1 contains an unprecedented imidazolyl-quinolinone substructure attached to a bromotyrosine-derived spiro-isoxazoline. Three other known alkaloids were isolated in addition to 1 and 4 and together represent the first examples of inhibitors of a new mycobacterial enzyme mycothiol S-conjugate amidase (MCA).
Nicholas
G M
GM
Laboratory of Bioorganic Chemistry, NIDDK, National Institutes of Health, Bethesda, Maryland 20892-0820, USA.
Newton
G L
GL
Fahey
R C
RC
Bewley
C A
CA
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D000581:Amidohydrolases / Q000037:antagonists & inhibitors*; D000818:Animals; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D014443:Tyrosine / Q000031:analogs & derivatives
D000470:Alkaloids; D000890:Anti-Infective Agents; D004791:Enzyme Inhibitors; D014443:Tyrosine; D000581:Amidohydrolases; C413523:mycothiol S-conjugate amidase