TL;DR: In this paper, a novel heteroaromatic substance, aaptamine possessing an α-adrenoceptor blocking activity has been isolated from the tropical sea sponge Aaptos aaptos and its structure has been determined to be 1 on the basis of spectral data and chemical degradation.
TL;DR: Four aaptamines isolated from the marine sponge Aaptos aaptos and their inhibitory activities against sortase A, an enzyme that plays a key role in cell wall protein anchoring and virulence in Staphylococcus aureus, were evaluated, providing the basis for further development of potent inhibitors.
TL;DR: In this paper, demethylaaptamine (2) and demethyl(oxy)aaptamines (3) have been isolated from the Okinawan marine sponge Aaptos aaptos as cytotoxic and antimicrobial substances.
Abstract: Two new a apptamine alkaloids, demethylaaptamine (2) and demethyl(oxy)aaptamine (3), have been isolated from the Okinawan marine sponge Aaptos aaptos as cytotoxic and antimicrobial substances. The structures of demethylaaptamine (2) and demethyl(oxy)aaptamine (3) were determined by interpretation of spectral data and results of chemical degradation experiments.
TL;DR: In the rabbit isolated aorta and renal artery, aaptamine produced a parallel, rightward shift of the dose‐response curve for noradrenaline, whereas that for histamine or KCl was not affected.
Abstract: In the rabbit isolated aorta and renal artery, aaptamine (3 X 10(-5)M), a novel heteroaromatic substance isolated from a sea sponge Aaptos aaptos produced a parallel, rightward shift of the dose-response curve for noradrenaline, whereas that for histamine or KCl was not affected. But, the derivatives of aaptamine, demethylaaptamine, demethyloxyaaptamine, dihydroaaptamine and dihydrodemethylaaptamine at concentrations of 10(-5) to 10(-4)M had no effect on the dose-response curve for noradrenaline. These results suggest that aaptamine is a competitive antagonist of alpha-adrenoceptors in vascular smooth muscles.
TL;DR: Two new derivatives of the alkaloid aaptamine were isolated from the bioactive chloroform fraction of the crude methanolic extract, enabling their identification to be 3-(phenethylamino)demethyl(oxy)aaptamine and 3-(isopentylamino).
Abstract: In a preliminary screen, Aaptos aaptos showed significant cytotoxic activity towards a panel of cell lines and was thus subjected to bioassay-guided isolation of the bioactive constituents. In addition to the known aaptamine, two new derivatives of the alkaloid were isolated from the bioactive chloroform fraction of the crude methanolic extract. Detailed analysis by NMR and mass spectroscopy enabled their identification to be 3-(phenethylamino)demethyl(oxy)aaptamine and 3-(isopentylamino)demethyl(oxy) aaptamine. The cytotoxic activities of the three alkaloids were further evaluated against CEM-SS cells.