Arenosclerins A-C and haliclonacyclamine E, new tetracyclic alkaloids from a Brazilian endemic Haplosclerid sponge Arenosclera brasiliensis.
Arenosclerins A (2), B (3), and C (4), as well as haliclonacyclamine E (1), are new tetracyclic alkylpiperidine alkaloids isolated from a new species of marine sponge belonging to the order Haplosclerida, Arenosclera brasiliensis, a species endemic to the southeastern Brazilian coast. The alkaloids were isolated as their hydrochloride salts and identified by analysis of spectroscopic data. Data obtained from (1)H-(1)H COSY, HMBC, and HSQC-TOCSY NMR experiments allowed complete assignment of the (1)H and (13)C resonances, and analysis of the NOESY and ROESY spectra showed that the only differences between 2, 3, and 4 were the relative stereochemistries of the bispiperidine ring system. Arenosclerins A-C are the first haliclonacyclamine/halicyclamine-related alkaloids with a hydroxy group in the bridging alkyl chain.
Torres
Y R
YR
Instituto de Química de São Carlos, Universidade de São Paulo CP 780, CEP 13560-970, São Carlos, SP, Brasil.
Berlinck
R G
RG
Magalhães
A
A
Schefer
A B
AB
Ferreira
A G
AG
Hajdu
E
E
Muricy
G
G
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D000818:Animals; D001938:Brazil; D002850:Chromatography, Gel; D002855:Chromatography, Thin Layer; D047028:Macrocyclic Compounds; D009682:Magnetic Resonance Spectroscopy; D010880:Piperidines / Q000737:chemistry / Q000302:isolation & purification*; D011161:Porifera / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D000470:Alkaloids; D047028:Macrocyclic Compounds; D010880:Piperidines; C414423:arenosclerin A; C414424:arenosclerin B; C414425:arenosclerin C; C414422:haliclonacyclamine E