Nostocyclamide: A new macrocyclic, thiazole-containing allelochemical from Nostoc sp. 31 (cyanobacteria)

Todorova, Albena K.; Juettner, Friedrich; Linden, Anthony; Pluess, Thomas; Philipsborn, W. Von

doi:10.1021/jo00129a032

Cited by 140 publications

(95 citation statements)

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“…The ecological and functional roles of these compounds remain enigmatic but involvement in metal-detoxification or metal-concentration mechanisms has been suggested (Bertram and Pattenden, 2007). Interestingly, other compounds within the same chemical family, that is, cyanobactins, are toxic to other cyanobacteria, possibly providing Prochloron and other cyanobacteria synthesizing such compounds with competitive advantages over other cyanobacteria (Todorova et al, 1995;Jü ttner et al, 2001;Hirose et al, 2009). Such allelopathic interactions may explain our finding of only a few other cyanobacteria within the cloacal cavity of L. patella.…”

Section: Discussionmentioning

confidence: 99%

Microbial diversity of biofilm communities in microniches associated with the didemnid ascidian Lissoclinum patella

et al. 2011

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We assessed the microbial diversity and microenvironmental niche characteristics in the didemnid ascidian Lissoclinum patella using 16S rRNA gene sequencing, microsensor and imaging techniques. L. patella harbors three distinct microbial communities spatially separated by few millimeters of tunic tissue: (i) a biofilm on its upper surface exposed to high irradiance and O 2 levels, (ii) a cloacal cavity dominated by the prochlorophyte Prochloron spp. characterized by strong depletion of visible light and a dynamic chemical microenvironment ranging from hyperoxia in light to anoxia in darkness and (iii) a biofilm covering the underside of the animal, where light is depleted of visible wavelengths and enriched in near-infrared radiation (NIR). Variable chlorophyll fluorescence imaging demonstrated photosynthetic activity, and hyperspectral imaging revealed a diversity of photopigments in all microhabitats. Amplicon sequencing revealed the dominance of cyanobacteria in all three layers. Sequences representing the chlorophyll d containing cyanobacterium Acaryochloris marina and anoxygenic phototrophs were abundant on the underside of the ascidian in shallow waters but declined in deeper waters. This depth dependency was supported by a negative correlation between A. marina abundance and collection depth, explained by the increased attenuation of NIR as a function of water depth. The combination of microenvironmental analysis and fine-scale sampling techniques used in this investigation gives valuable first insights into the distribution, abundance and diversity of bacterial communities associated with tropical ascidians. In particular, we show that microenvironments and microbial diversity can vary significantly over scales of a few millimeters in such habitats; which is information easily lost by bulk sampling.

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Section: Discussionmentioning

confidence: 99%

Microbial diversity of biofilm communities in microniches associated with the didemnid ascidian Lissoclinum patella

et al. 2011

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“…Nostoc linckia produced and released another allelochemical named cyanobacterin LU-1 that inhibited the growth of many cyanobacteria and eukaryotic algae but not heterotrophic bacteria and fungi (Gromov et al, 1991). Nostoc strain 31 produces cyclic heptapeptides, nostocyclamide and nostocyclamide M, which are allelopathically active against cyanobacteria and algae (Todorova and Jüttner, 1995;Jüttner et al, 2001).…”

Section: Cyanobacteriamentioning

confidence: 99%

Allelopathy of Aquatic Autotrophs

Gross¹

2003

Critical Reviews in Plant Sciences

537

355

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Allelopathy in aquatic environments may provide a competitive advantage to angiosperms, algae, or cyanobacteria in their interaction with other primary producers. Allelopathy can influence the competition between different photoautotrophs for resources and change the succession of species, for exarnple, in phytoplankton cornmunities. Field evidence and laboratory studies indicate that allelopathy occurs in all aquatic habitats (marine and freshwater), and that ail prirnary producing organisms (cyanobacteria, micro-and macroalgae as well as angiospenns) are capable of producing and releasing allelopathically active compounds. Although allelopathy also includes positive (stimulating) interactions, the majority of studies describe the inhibitory activity of ailelopathicaily active compounds. Different mechanisms operate depending on whether allelopathy takes place in the Open water (pelagic zone) or is Substrate associated (benthic habitats). Allelopathical interactions are especiaily common in fully aquatic species, such as submersed macrophytes or benthic algae and cyanobacteria. The prevention of shading by epiphytic and planktonic primary producers and the competition for space may be the ultimate cause for allelopathical interactions. Aquatic ailelochemicals often target multiple physiological processes. The inhibition of photosynthesis of competing primary producers seems tobe a frequent mode of action. Multiple biotic and abiotic factors determine the strength of allelopathic interactions. Bacteria associated with the donor or target organism can metabolize excreted aiielochemicals. Frequently, the impact of surplus or limiting nutrients has been shown to affect the overail production of allelochemicals and their effect on target species. Similarities and differences of ailelopathic interactions in marine and freshwater habitats as well as between the different types of producing organisms are discussed.

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“…that inhibit several microorganisms (23, 24); and the nostocyclamides, relatively small cyclic peptides from Nostoc sp. that inhibit cyanobacteria and microalgae (25,26). Different ecological roles have been attributed to the production of allelochemicals by cyanobacteria, including phytoplankton succession, bloom formation, resource and interference competition (27), and invasive fitness (28).…”

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Synergistic allelochemicals from a freshwater cyanobacterium

Leão

Pereira²,

Liu³

et al. 2010

Proc. Natl. Acad. Sci. U.S.A.

112

108

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The ability of cyanobacteria to produce complex secondary metabolites with potent biological activities has gathered considerable attention due to their potential therapeutic and agrochemical applications. However, the precise physiological or ecological roles played by a majority of these metabolites have remained elusive. Several studies have shown that cyanobacteria are able to interfere with other organisms in their communities through the release of compounds into the surrounding medium, a phenomenon usually referred to as allelopathy. Exudates from the freshwater cyanobacterium Oscillatoria sp. had previously been shown to inhibit the green microalga Chlorella vulgaris. In this study, we observed that maximal allelopathic activity is highest in early growth stages of the cyanobacterium, and this provided sufficient material for isolation and chemical characterization of active compounds that inhibited the growth of C. vulgaris. Using a bioassay-guided approach, we isolated and structurally characterized these metabolites as cyclic peptides containing several unusually modified amino acids that are found both in the cells and in the spent media of Oscillatoria sp. cultures. Strikingly, only the mixture of the two most abundant metabolites in the cells was active toward C. vulgaris. Synergism was also observed in a lung cancer cell cytotoxicity assay. The binary mixture inhibited other phytoplanktonic organisms, supporting a natural function of this synergistic mixture of metabolites as allelochemicals.allelopathy | chemical ecology | Oscillatoria | cyclic peptides | synergism C yanobacteria are a prolific source of nearly 800 diverse bioactive secondary metabolites, originating mainly from nonribosomal peptide synthetase (NRPS) or mixed polyketide synthase (PKS)-NRPS biosynthesis (1, 2). Efforts to isolate and characterize cyanobacterial metabolites have usually been motivated from a desire to describe either their natural toxicity toward animals in natural settings (e.g., ref.3) or promising activities from in vitro biomedical screening programs (e.g., ref. 4, 5). However, in general the ecological role played by the majority of these metabolites is not well known (6, 7). Functions established to date for cyanobacterial secondary metabolites include nitrogen storage (8), UV protection (9), metal chelation (10), defense against predation (11), and quorum sensing (12).Allelopathy refers to the chemically mediated interaction between plants or microorganisms (13). These interactions are characterized by the release of allelopathic compounds (allelochemicals) into the surrounding medium, eliciting either a positive or deleterious response in a target organism (13). In aquatic ecosystems, allelopathy is regarded as an important process influencing the shaping of microbial communities (14-16). Toxic properties have been attributed to cyanobacteria over the last 130 yr (e.g., ref. 17), and the allelopathic potential of these organisms was described through field-derived observations in the 1970s (18,19). Since th...

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Nostocyclamide: A new macrocyclic, thiazole-containing allelochemical from Nostoc sp. 31 (cyanobacteria)

Cited by 140 publications

References 2 publications

Microbial diversity of biofilm communities in microniches associated with the didemnid ascidian Lissoclinum patella

Microbial diversity of biofilm communities in microniches associated with the didemnid ascidian Lissoclinum patella

Allelopathy of Aquatic Autotrophs

Synergistic allelochemicals from a freshwater cyanobacterium

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