Synthesis of 3-Alkyl Pyridinium Alkaloids from the Arctic Sponge Haliclona viscosa

Timm, Christoph; Mordhorst, Thorsten; Köck, Matthias

doi:10.3390/md8030483

Cited by 22 publications

(15 citation statements)

References 40 publications

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“…lendenfeldi might be related to the presence of Latrunculia -associated natural products that have already been reported to have inhibitory potential against various Gram-positive and Gram-negative bacteria, which are known as the discorhabdins [21,22,23] and trunculins [24]. Furthermore, sponges of the genus Haliclona , which also include polar species, are known to contain antibacterial 3-alkylpyridinium alkaloids [25,26]. Similarly, sesquiterpenoids halichonadins [27] and a galactoside-specific lectin [28] from Halichondria sponges have been described to have antibacterial and antifungal effects, while extracts from sponges of the genus Hemigellius have not yet been reported to show any antibiotic properties.…”

Section: Resultsmentioning

confidence: 99%

Biological Activities of Ethanolic Extracts from Deep-Sea Antarctic Marine Sponges

et al. 2013

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We report on the screening of ethanolic extracts from 33 deep-sea Antarctic marine sponges for different biological activities. We monitored hemolysis, inhibition of acetylcholinesterase, cytotoxicity towards normal and transformed cells and growth inhibition of laboratory, commensal and clinically and ecologically relevant bacteria. The most prominent activities were associated with the extracts from sponges belonging to the genus Latrunculia, which show all of these activities. While most of these activities are associated to already known secondary metabolites, the extremely strong acetylcholinesterase inhibitory potential appears to be related to a compound unknown to date. Extracts from Tetilla leptoderma, Bathydorus cf. spinosus, Xestospongia sp., Rossella sp., Rossella cf. racovitzae and Halichondria osculum were hemolytic, with the last two also showing moderate cytotoxic potential. The antibacterial tests showed significantly greater activities of the extracts of these Antarctic sponges towards ecologically relevant bacteria from sea water and from Arctic ice. This indicates their ecological relevance for inhibition of bacterial microfouling.

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Section: Resultsmentioning

confidence: 99%

Biological Activities of Ethanolic Extracts from Deep-Sea Antarctic Marine Sponges

et al. 2013

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“…In 2009, new haliclamines E ( 172 ) and F ( 173 ) (Figure 17) were subsequently obtained from this Arctic sponge [96]. Compound 169 showed activity in the feeding deterrence assay against the amphipod Anonyx nugax and the starfish Asterias rubens from the North Sea [97]. Compounds 169 and 170 showed a strong inhibition against two bacterial strains isolated from the vicinity of the sponge [95,97].…”

Section: Spongesmentioning

confidence: 99%

“…Compound 169 showed activity in the feeding deterrence assay against the amphipod Anonyx nugax and the starfish Asterias rubens from the North Sea [97]. Compounds 169 and 170 showed a strong inhibition against two bacterial strains isolated from the vicinity of the sponge [95,97]. The synthesis of the Arctic sponge alkaloids were also achieved by two groups [97,98].…”

Section: Spongesmentioning

confidence: 99%

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Secondary Metabolites from Polar Organisms

Tian

Zhao

2017

Marine Drugs

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Polar organisms have been found to develop unique defences against the extreme environment environment, leading to the biosynthesis of novel molecules with diverse bioactivities. This review covers the 219 novel natural products described since 2001, from the Arctic and the Antarctic microoganisms, lichen, moss and marine faunas. The structures of the new compounds and details of the source organism, along with any relevant biological activities are presented. Where reported, synthetic and biosynthetic studies on the polar metabolites have also been included.

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“…N-Alkyl quaternary pyridinium salts can be prepared by simple, economical and short synthetic methods. Pyridinium salts, largely of synthetic origin, and some natural products (Timm et al, 2010) have been found to show good antimicrobial activity (Obando et al, 2009;Ilangovan et al, 2012). Pyridinium succinate and acesulfamate showed good antimicrobial and insect deterrent activity (Hough-Troutman et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

1-Alkyl-(N,N-dimethylamino)pyridinium bromides: inhibitory effect on virulence factors of Candida albicans and on the growth of bacterial pathogens

Sundararaman

Kumar

Venkatesan

et al. 2013

Journal of Medical Microbiology

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A homologous series of 1-alkyl-(N,N-dimethylamino)pyridinium bromides, termed compounds 1-11, was synthesized and studied for antibacterial and antifungal activity. Of these, compound 8, containing a ten-carbon alkyl chain, showed maximum inhibition against all the tested bacterial strains. The highest antibacterial activity using a disc diffusion method was recorded against Mycobacterium smegmatis [zone of inhibition (ZOI): 45.75±0.25 mm], followed by Escherichia coli, Proteus mirabilis, Vibrio cholerae, Staphylococcus aureus and Salmonella typhi. In addition to antibacterial activity, compounds 3-11 displayed good inhibitory action against the human opportunistic yeast pathogens Cryptococcus neoformans and various Candida spp. The maximum ZOI was observed against Cryptococcus neoformans (51.5±0.5 mm) using compound 8, with ZOIs of 23.5±0.5, 32.0±0.0, 27.75±0.25 and 41.5±0.5 mm against Candida albicans, Candida glabrata, Candida tropicalis and Candida krusei, respectively. Furthermore, compound 8 caused inhibition of the candidal yeast-hyphae transition at a concentration of 0.29 mM and also inhibited the secretion of extracellular hydrolytic enzyme such as secreted aspartyl proteinase at subinhibitory concentrations. Compound 8 showed very little haemolytic activity at a concentration of 0.58 mM (1.315±0.75 %), with its highest haemolytic activity (47.806±2.32 %) observed at a concentration of 2.9 mM.

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Synthesis of 3-Alkyl Pyridinium Alkaloids from the Arctic Sponge Haliclona viscosa

Cited by 22 publications

References 40 publications

Biological Activities of Ethanolic Extracts from Deep-Sea Antarctic Marine Sponges

Biological Activities of Ethanolic Extracts from Deep-Sea Antarctic Marine Sponges

Secondary Metabolites from Polar Organisms

1-Alkyl-(N,N-dimethylamino)pyridinium bromides: inhibitory effect on virulence factors of Candida albicans and on the growth of bacterial pathogens

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