Two New Haliclamines from the Arctic Sponge Haliclona viscosa

Abstract

There are a large number of studies on sponges from warm or tropical waters, whereas little is known about the chemistry of sponges from Arctic waters. Here, we describe the isolation and structure elucidation of two new 3-alkyltetrahydropyridine alkaloids (haliclamines C and D) from the Arctic sponge Haliclona viscosa. MS and 2D NMR spectroscopy

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

“…Recently, two forms of viscosaline have been isolated (Schmidt et al 2012). In addition to this, two other alkaloids, haliclamine C and D, were isolated from H. viscosa (Volk et al 2004). …”

Polycyclic Diamine Alkaloids from Marine Sponges

“…The EtOAc and n-BuOH extracts of the sponge Haliclona viscosa collected off the coast of Blomstrandhalvøya, Svalbard, Arctic Sea, yielded haliclamines C (1) and D (2) [12]. Both alkaloids have been isolated by gel permeation chromatography on Sephadex LH-20 and purified by C 18 RP-HPLC.…”

“…However, both alkaloids displayed significant antibacterial activity. Interestingly, both 1 and 2 have been isolated from samples of H. viscosa collected during 1999, but these alkaloids were not detected in samples of the same sponge collected in 2000 and 2001 [12]. …”

Structure Elucidation of Submilligram Quantities of Natural Products - Application to Haliclamines G and H from the Arctic Marine Sponge Haliclona viscosa

“…Another group of 3-APAs are the haliclamines, cyclic dimeric 3-alkyl tetrahydropyridine alkaloids in which two tetrahydropyridine moieties are connected in 1-and 3-position [7] by alkyl chains of variable length (Scheme 1, Table 1). While the originally described haliclamines A (3) and B (4) possess at least one double bond in each alkyl chain [8], haliclamines C to F (5-8) [9,10] contain saturated alkyl chains. Mono-, di-, tri-, and polymeric 3-alkyl pyridinium compounds have been identified in six different sponge families of the order Haplosclerida from all over the world.…”

“…In contrast to the 3-APAs in general, the dimeric haliclamines have been reported to date from only two locations: a) Hiburi-jima, Japan, source Scheme 1. Haliclamines A-H (1-8) and viscosaline C (9). The assignment of the indices (m, n) to the different haliclamines is given in Table 1. of haliclamines A and B (3 and 4) and b) the Svalbard archipelago, source of haliclamines C to F (5-8), and only from the sponge genus Haliclona.…”