Petrosamine B, an inhibitor of the Helicobacter pylori enzyme aspartyl semialdehyde dehydrogenase from the Australian sponge Oceanapia sp.
Bioassay-guided fractionation of the MeOH extract of the sponge Oceanapia sp. using the Helicobacter pylori enzyme, aspartyl semialdehyde dehydrogenase, ASD, to detect antibacterial activity, led to the isolation of a new pyridoacridine alkaloid, petrosamine B (1). Petrosamine B is a bright blue compound that is sparingly soluble in many organic solvents. The structure of 1 was determined from detailed NMR studies performed in TFA/D2O. Petrosamine B was found to be a weak inhibitor of ASD with an IC50 of 306 microM.
Carroll
Anthony R
AR
Natural Product Discovery, Eskitis Institute, Griffith University, Brisbane, Queensland, Australia 4111. A.Carroll@griffith.edu.au
Ngo
Anna
A
Quinn
Ronald J
RJ
Redburn
Joanne
J
Hooper
John N A
JN
D000166:Acridines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000444:Aldehyde Dehydrogenase / Q000037:antagonists & inhibitors*; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D001315:Australia; D001426:Bacterial Proteins / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D016480:Helicobacter pylori / Q000201:enzymology*; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010616:Phenanthrenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry*
D000166:Acridines; D000470:Alkaloids; D001426:Bacterial Proteins; D004791:Enzyme Inhibitors; D010616:Phenanthrenes; C501791:petrosamine B; D000444:Aldehyde Dehydrogenase; C501792:aspartyl semialdehyde dehydrogenase, Helicobacter pylori