Viscosaline: new 3-alkyl pyridinium alkaloid from the Arctic sponge Haliclona viscosa

Abstract

Polycyclic pyridinium alkaloids are widely distributed in several sponges of the order Haplosclerida. So far, studies on Haliclona and related genera were mainly concentrated on warm or tropical waters. Here, we describe the chemical investigation of the Arctic sponge Haliclona viscosa and structure elucidation of the acyclic 1,3-dialkyl pyridinium alkaloid viscosaline. A novel structural motif of viscosaline is that beta-alanine is covalently bound to one alkyl chain.

Secondary Metabolites from Polar Organisms

“…In 2003, chemical investigation of the Arctic sponge Haliclona viscosa led to the isolation of a new trimeric 3-alkyl pyridinium alkaloid, viscosamine ( 168 ) (Figure 17) [93]. Further investigation of this sponge yielded one new 3-alkyl pyridinium alkaloid, viscosaline ( 169 ) (Figure 17) [94], and two new 3-alkyltetrahy-dropyridine alkaloids, haliclamines C ( 170 ) and D ( 171 ) (Figure 17) [95]. In 2009, new haliclamines E ( 172 ) and F ( 173 ) (Figure 17) were subsequently obtained from this Arctic sponge [96].…”

In vitro screening of antifungal activity of marine sponge extracts against five phytopathogenic fungi

“…1989 have isolated two cytotoxic compounds, haliclamine A and B from H. viscosa . Volk and Kock 2003 have isolated viscosamine, then viscosaline in Volk and Kock 2004. Recently, two forms of viscosaline have been isolated (Schmidt et al 2012).…”

Comparison of two marine sponge-associatedPenicillium strains DQ25 and SC10: differences in secondary metabolites and their bioactivities

“…They are conspicuous organisms of benthic communities, and are well known as a resource for a variety of secondary metabolites. The examples include a pyridinium alkaloid from the Arctic sponge Haliclona viscose (Volk and Köck, 2004), the antifouling quinolizidine alkaloid from Haliclona exigua (LimnaMol et al, 2009), cyclic peptide from a Palaun Haliclona sp. (Sera et al, 2002).…”