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 Aplysin...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2002-05, Vol.65 (5), p.796-799
Main Authors: SAEKI, Beatriz M., GRANATO, Ana Claudia, BERLINCK, Roberto G. S., MAGALHãES, Alviclér, SCHEFER, Alexandre B., FERREIRA, Antonio G., PINHEIRO, Ulisses S., HAJDU, Eduardo
Format: Article
Language:English
Subjects:
Alcaloids
alkaloids
Alkaloids - chemistry
Alkaloids - isolation & purification
Analytical, structural and metabolic biochemistry
Animals
Aplysina caissara
Biological and medical sciences
Brazil
caissarines
Chromatography, High Pressure Liquid
Circular Dichroism
Fundamental and applied biological sciences. Psychology
Heterocyclic compounds, pigments
Marine
Molecular Structure
natural products
Nuclear Magnetic Resonance, Biomolecular
Other biological molecules
Porifera - chemistry
Spectroscopy, Fourier Transform Infrared
Tyrosine - analogs & derivatives
Tyrosine - chemistry
Tyrosine - isolation & purification
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Summary: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.
ISSN:0163-3864
1520-6025
DOI:10.1021/np0105735