Two unprecedented dibromotyrosine-derived alkaloids from the Brazilian endemic marine sponge Aplysina caissara.
Two new bromotyrosine-derived alkaloids, caissarine A (1) and caissarine B (2), along with three known biogenetically related alkaloids, aeroplysinin-1, fistularin-3, and the artifact of isolation 2-(3,5-dibromo-4-dimethoxy-1-hydroxy-2,5-cyclohexadien-1-yl)ethanamide, have been isolated from Aplysina caissara, an endemic species of marine sponge from the Southeastern Brazilian coast. The alkaloids have been identified by analysis of spectroscopic data. While caissarine A has a 2-hydroxyagmatine moiety in its structure, caissarin B is the first naturally occurring compound encompassing the unprecedented 1,7-diamino-3-hydroxyheptane moiety.
Saeki
Beatriz M
BM
Instituto de Química de São Carlos, Universidade de São Paulo CP 780, CEP 13560-970, São Carlos, SP, Brazil.
Granato
Ana Claudia
AC
Berlinck
Roberto G S
RG
Magalhães
Alviclér
A
Schefer
Alexandre B
AB
Ferreira
Antonio G
AG
Pinheiro
Ulisses S
US
Hajdu
Eduardo
E
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D000818:Animals; D001938:Brazil; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D014443:Tyrosine / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification*
D000470:Alkaloids; C461800:caissarine A; C461801:caissarine B; D014443:Tyrosine