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Journal articles on the topic 'Cyanopeptoline'

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Published: 4 June 2021
Last updated: 17 February 2022

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1

Rounge, Trine B., Thomas Rohrlack, Ave Tooming-Klunderud, Tom Kristensen, and Kjetill S. Jakobsen. "Comparison of Cyanopeptolin Genes in Planktothrix, Microcystis, and Anabaena Strains: Evidence for Independent Evolution within Each Genus." Applied and Environmental Microbiology 73, no. 22 (October 5, 2007): 7322–30. http://dx.doi.org/10.1128/aem.01475-07.

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ABSTRACT The major cyclic peptide cyanopeptolin 1138, produced by Planktothrix strain NIVA CYA 116, was characterized and shown to be structurally very close to the earlier-characterized oscillapeptin E. A cyanopeptolin gene cluster likely to encode the corresponding peptide synthetase was sequenced from the same strain. The 30-kb oci gene cluster contains two novel domains previously not detected in nonribosomal peptide synthetase gene clusters (a putative glyceric acid-activating domain and a sulfotransferase domain), in addition to seven nonribosomal peptide synthetase modules. Unlike in two previously described cyanopeptolin gene clusters from Anabaena and Microcystis, a halogenase gene is not present. The three cyanopeptolin gene clusters show similar gene and domain arrangements, while the binding pocket signatures deduced from the adenylation domain sequences and the additional tailoring domains vary. This suggests loss and gain of tailoring domains within each genus, after the diversification of the three clades, as major events leading to the present diversity. The ABC transporter genes associated with the cyanopeptolin gene clusters form a monophyletic clade and accordingly are likely to have evolved as part of the functional unit. Phylogenetic analyses of adenylation and condensation domains, including domains from cyanopeptolins and microcystins, show a closer similarity between the Planktothrix and Microcystis cyanopeptolin domains than between these and the Anabaena domain. No clear evidence of recombination between cyanopeptolins and microcystins could be detected. There were no strong indications of horizontal gene transfer of cyanopeptolin gene sequences across the three genera, supporting independent evolution within each genus.
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2

Choi, Hyukjae, Sun Kwan Oh, Wonho Yih, Jungwook Chin, Heonjoong Kang, and Jung-Rae Rho. "Cyanopeptoline CB071: A Cyclic Depsipeptide Isolated from the Freshwater Cyanobacterium Aphanocapsa sp." CHEMICAL & PHARMACEUTICAL BULLETIN 56, no. 8 (2008): 1191–93. http://dx.doi.org/10.1248/cpb.56.1191.

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3

Fastner, Jutta, Marcel Erhard, and Hans von Döhren. "Determination of Oligopeptide Diversity within a Natural Population of Microcystis spp. (Cyanobacteria) by Typing Single Colonies by Matrix-Assisted Laser Desorption Ionization–Time of Flight Mass Spectrometry." Applied and Environmental Microbiology 67, no. 11 (November 1, 2001): 5069–76. http://dx.doi.org/10.1128/aem.67.11.5069-5076.2001.

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ABSTRACT Besides the most prominent peptide toxin, microcystin, the cyanobacteria Microcystis spp. have been shown to produce a large variety of other bioactive oligopeptides. We investigated for the first time the oligopeptide diversity within a naturalMicrocystis population by analyzing single colonies directly with matrix-assisted laser desorption ionization–time of flight mass spectrometry (MALDI-TOF MS). The results demonstrate a high diversity of known cyanobacterial peptides such as microcystins, anabaenopeptins, microginins, aeruginosins, and cyanopeptolins, but also many unknown substances in the Microcystis colonies. Oligopeptide patterns were mostly related to specificMicrocystis taxa. Microcystis aeruginosa(Kütz.) Kütz. colonies contained mainly microcystins, occasionally accompanied by aeruginosins. In contrast, microcystins were not detected in Microcystis ichthyoblabeKütz.; instead, colonies of this species contained anabaenopeptins and/or microginins or unknown peptides. Within a third group, Microcystis wesenbergii (Kom.) Kom. in Kondr., chiefly a cyanopeptolin and an unknown peptide were found. Similar patterns, however, were also found in colonies which could not be identified to species level. The significance of oligopeptides as a chemotaxonomic tool within the genus Microcystis is discussed. It could be demonstrated that the typing of single colonies by MALDI-TOF MS may be a valuable tool for ecological studies of the genus Microcystis as well as in early warning of toxic cyanobacterial blooms.
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4

Weckesser, Jürgen, Cornel Martin, and Clemens Jakobi. "Cyanopeptolins, depsipeptides from cyanobacteria." Systematic and Applied Microbiology 19, no. 2 (August 1996): 133–38. http://dx.doi.org/10.1016/s0723-2020(96)80038-5.

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5

Köcher, Steffen, Sarah Resch, Till Kessenbrock, Lukas Schrapp, Michael Ehrmann, and Markus Kaiser. "From dolastatin 13 to cyanopeptolins, micropeptins, and lyngbyastatins: the chemical biology of Ahp-cyclodepsipeptides." Natural Product Reports 37, no. 2 (2020): 163–74. http://dx.doi.org/10.1039/c9np00033j.

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Ahp-cyclodepsipeptides (also known as Ahp-containing cyclodepsipeptides, cyanopeptolins, micropeptins, microginines, and lyngbyastatins, and by many other names) are a natural product family with potent serine protease inhibitory properties.
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6

Bister, Bojan, Simone Keller, Heike I. Baumann, Graeme Nicholson, Stefan Weist, Günther Jung, Roderich D. Süssmuth, and Friedrich Jüttner. "Cyanopeptolin 963A, a Chymotrypsin Inhibitor ofMicrocystisPCC 7806." Journal of Natural Products 67, no. 10 (October 2004): 1755–57. http://dx.doi.org/10.1021/np049828f.

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7

Matern, Ute, Lukas Oberer, Marcel Erhard, Michael Herdman, and Jürgen Weckesser. "Hofmannolin, a cyanopeptolin from Scytonema hofmanni PCC 7110." Phytochemistry 64, no. 6 (November 2003): 1061–67. http://dx.doi.org/10.1016/s0031-9422(03)00467-9.

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8

Kodani, Shinya, Hisayuki Komaki, Hikaru Hemmi, Yuto Miyake, Issara Kaweewan, and Hideo Dohra. "Streptopeptolin, a Cyanopeptolin-Type Peptide from Streptomyces olivochromogenes." ACS Omega 3, no. 7 (July 19, 2018): 8104–10. http://dx.doi.org/10.1021/acsomega.8b01042.

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9

MARTIN, CORNEL, LUKAS OBERER, TOMIO INO, WILFRIED A. KÖNIG, MICHAEL BUSCH, and JÜRGEN WECKESSER. "Cyanopeptolins, new depsipeptides from the cyanobacterium Microcystis sp. pcc 7806." Journal of Antibiotics 46, no. 10 (1993): 1550–56. http://dx.doi.org/10.7164/antibiotics.46.1550.

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10

von Elert, Eric, Lukas Oberer, Petra Merkel, Thomas Huhn, and Judith F. Blom. "Cyanopeptolin 954, a Chlorine-Containing Chymotrypsin Inhibitor ofMicrocystisaeruginosaNIVA Cya 43." Journal of Natural Products 68, no. 9 (September 2005): 1324–27. http://dx.doi.org/10.1021/np050079r.

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11

Jakobi, Clemens, Lukas Oberer, Charles Quiquerez, Wilfried A. König, and Jürgen Weckesser. "Cyanopeptolin S, a sulfate-containing depsipeptide from a water bloom ofMicrocystissp." FEMS Microbiology Letters 129, no. 2-3 (June 1995): 129–33. http://dx.doi.org/10.1111/j.1574-6968.1995.tb07569.x.

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12

JAKOBI, C., L. OBERER, C. QUIQUEREZ, W. KONIG, and J. WECKESSER. "Cyanopeptolin S, a sulfate-containing depsipeptide from a water bloom of sp." FEMS Microbiology Letters 129, no. 2-3 (June 15, 1995): 129–33. http://dx.doi.org/10.1016/0378-1097(95)00146-v.

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13

Mazur-Marzec, Hanna, Anna Fidor, Marta Cegłowska, Ewa Wieczerzak, Magdalena Kropidłowska, Marie Goua, Jenny Macaskill, and Christine Edwards. "Cyanopeptolins with Trypsin and Chymotrypsin Inhibitory Activity from the Cyanobacterium Nostoc edaphicum CCNP1411." Marine Drugs 16, no. 7 (June 26, 2018): 220. http://dx.doi.org/10.3390/md16070220.

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14

Hasin, Ohad, and Shmuel Carmeli. "Isolation and Structure Elucidation of Secondary Metabolites from a Microcystis sp. Bloom Material Collected in Southern Israel." Natural Product Communications 13, no. 10 (October 2018): 1934578X1801301. http://dx.doi.org/10.1177/1934578x1801301020.

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The hydrophilic extract of Microcystis sp. bloom material collected from Bror Hayil Reservoir in southern Israel afforded four new metabolites, (2 S,3 S)-3-hydeoxy-1,4-diphenylbutan-2-yl-acetate, aeruginosins BH604, BH462A and BH462B, and two known metabolites cyanopeptolins S and SS. The planar structure of 1–4 was established by analyses of their 1D and 2D NMR data and mass spectrometric data. The absolute configurations of the chiral centers of 1 were established by Mosher method and analysis of the coupling constants between H-2 and H-3, and those of 2–4 by Merfay's method and advanced Merfay's method and chiral HPLC. The compounds do not inhibit the serine proteases trypsin and thrombin.
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15

Gademann, Karl, Cyril Portmann, Judith F. Blom, Michael Zeder, and Friedrich Jüttner. "Multiple Toxin Production in the CyanobacteriumMicrocystis: Isolation of the Toxic Protease Inhibitor Cyanopeptolin 1020." Journal of Natural Products 73, no. 5 (May 28, 2010): 980–84. http://dx.doi.org/10.1021/np900818c.

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16

Jakobi, Clemens, Kenneth L. Rinehart, Rolf Neuber, Konstanze Mez, and Jürgen Weckesser. "Cyanopeptolin SS, a disulphated depsipeptide from a water bloom: structural elucidation and biological activities." Phycologia 35, sup6 (November 1996): 111–16. http://dx.doi.org/10.2216/i0031-8884-35-6s-111.1.

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17

Racine, Marianne, Ammar Saleem, and Frances R. Pick. "Metabolome Variation between Strains of Microcystis aeruginosa by Untargeted Mass Spectrometry." Toxins 11, no. 12 (December 11, 2019): 723. http://dx.doi.org/10.3390/toxins11120723.

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Cyanobacteria are notorious for their potential to produce hepatotoxic microcystins (MCs), but other bioactive compounds synthesized in the cells could be as toxic, and thus present interest for characterization. Ultra performance liquid chromatography and high-resolution accurate mass spectrometry (UPLC-QTOF-MS/MS) combined with untargeted analysis was used to compare the metabolomes of five different strains of the common bloom-forming cyanobacterium, Microcystis aeruginosa. Even in microcystin-producing strains, other classes of oligopeptides including cyanopeptolins, aeruginosins, and aerucyclamides, were often the more dominant compounds. The distinct and large variation between strains of the same widespread species highlights the need to characterize the metabolome of a larger number of cyanobacteria, especially as several metabolites other than microcystins can affect ecological and human health.
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18

Okumura, Hilary S., Benjamin Philmus, Cyril Portmann, and Thomas K. Hemscheidt. "Homotyrosine-Containing Cyanopeptolins 880 and 960 and Anabaenopeptins 908 and 915 fromPlanktothrix agardhiiCYA 126/8." Journal of Natural Products 72, no. 1 (January 23, 2009): 172–76. http://dx.doi.org/10.1021/np800557m.

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19

Lenz, Kade A., Todd R. Miller, and Hongbo Ma. "Anabaenopeptins and cyanopeptolins induce systemic toxicity effects in a model organism the nematode Caenorhabditis elegans." Chemosphere 214 (January 2019): 60–69. http://dx.doi.org/10.1016/j.chemosphere.2018.09.076.

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20

Tonk, Linda, Martin Welker, Jef Huisman, and Petra M. Visser. "Production of cyanopeptolins, anabaenopeptins, and microcystins by the harmful cyanobacteria Anabaena 90 and Microcystis PCC 7806." Harmful Algae 8, no. 2 (January 2009): 219–24. http://dx.doi.org/10.1016/j.hal.2008.05.005.

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21

Rounge, Trine B., Thomas Rohrlack, Tom Kristensen, and Kjetill S. Jakobsen. "Recombination and selectional forces in cyanopeptolin NRPS operons from highly similar, but geographically remote Planktothrix strains." BMC Microbiology 8, no. 1 (2008): 141. http://dx.doi.org/10.1186/1471-2180-8-141.

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22

Fidor, Anna, Robert Konkel, and Hanna Mazur-Marzec. "Bioactive Peptides Produced by Cyanobacteria of the Genus Nostoc: A Review." Marine Drugs 17, no. 10 (September 29, 2019): 561. http://dx.doi.org/10.3390/md17100561.

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Cyanobacteria of the genus Nostoc are widespread in all kinds of habitats. They occur in a free-living state or in association with other organisms. Members of this genus belong to prolific producers of bioactive metabolites, some of which have been recognized as potential therapeutic agents. Of these, peptides and peptide-like structures show the most promising properties and are of a particular interest for both research laboratories and pharmaceutical companies. Nostoc is a sole source of some lead compounds such as cytotoxic cryptophycins, antiviral cyanovirin-N, or the antitoxic nostocyclopeptides. Nostoc also produces the same bioactive peptides as other cyanobacterial genera, but they frequently have some unique modifications in the structure. This includes hepatotoxic microcystins and potent proteases inhibitors such as cyanopeptolins, anabaenopeptins, and microginins. In this review, we described the most studied peptides produced by Nostoc, focusing especially on the structure, the activity, and a potential application of the compounds.
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23

Faltermann, Susanne, Sara Zucchi, Esther Kohler, Judith F. Blom, Jakob Pernthaler, and Karl Fent. "Molecular effects of the cyanobacterial toxin cyanopeptolin (CP1020) occurring in algal blooms: Global transcriptome analysis in zebrafish embryos." Aquatic Toxicology 149 (April 2014): 33–39. http://dx.doi.org/10.1016/j.aquatox.2014.01.018.

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24

Overlingė, Donata, Anna Toruńska-Sitarz, Marta Cegłowska, Agata Błaszczyk, Karolina Szubert, Renata Pilkaitytė, and Hanna Mazur-Marzec. "Phytoplankton of the Curonian Lagoon as a New Interesting Source for Bioactive Natural Products. Special Impact on Cyanobacterial Metabolites." Biomolecules 11, no. 8 (August 2, 2021): 1139. http://dx.doi.org/10.3390/biom11081139.

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The bioprospecting of marine and brackish water systems has increased during the last decades. In this respect, microalgae, including cyanobacteria, and their metabolites are one of the most widely explored resources. Most of the bioactive compounds are isolated from ex situ cultures of microorganisms; however, analysis of field samples could also supply valuable information about the metabolic and biotechnological potential of microalgae communities. In this work, the activity of phytoplankton samples from the Curonian Lagoon was studied. The samples were active against antibiotic resistant clinical and environmental bacterial strains as well as against serine proteases and T47D human breast adenocarcinoma cells. No significant effect was found on Daphnia magna. In addition, using LC-MS/MS, we documented the diversity of metabolites present in field samples. A list of 117 detected cyanopeptides was presented. Cyanopeptolins constituted the largest class of cyanopeptides. As complex bloom samples were analyzed, no link between the observed activity and a specific sample component can be established. However, the results of the study showed a biotechnological potential of natural products from the Curonian Lagoon.
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25

Kust, Andreja, Klára Řeháková, Jaroslav Vrba, Vincent Maicher, Jan Mareš, Pavel Hrouzek, Maria-Cecilia Chiriac, Zdeňka Benedová, Blanka Tesařová, and Kumar Saurav. "Insight into Unprecedented Diversity of Cyanopeptides in Eutrophic Ponds Using an MS/MS Networking Approach." Toxins 12, no. 9 (August 31, 2020): 561. http://dx.doi.org/10.3390/toxins12090561.

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Man-made shallow fishponds in the Czech Republic have been facing high eutrophication since the 1950s. Anthropogenic eutrophication and feeding of fish have strongly affected the physicochemical properties of water and its aquatic community composition, leading to harmful algal bloom formation. In our current study, we characterized the phytoplankton community across three eutrophic ponds to assess the phytoplankton dynamics during the vegetation season. We microscopically identified and quantified 29 cyanobacterial taxa comprising non-toxigenic and toxigenic species. Further, a detailed cyanopeptides (CNPs) profiling was performed using molecular networking analysis of liquid chromatography-tandem mass spectrometry (LC-MS/MS) data coupled with a dereplication strategy. This MS networking approach, coupled with dereplication, on the online global natural product social networking (GNPS) web platform led us to putatively identify forty CNPs: fourteen anabaenopeptins, ten microcystins, five cyanopeptolins, six microginins, two cyanobactins, a dipeptide radiosumin, a cyclooctapeptide planktocyclin, and epidolastatin 12. We applied the binary logistic regression to estimate the CNPs producers by correlating the GNPS data with the species abundance. The usage of the GNPS web platform proved a valuable approach for the rapid and simultaneous detection of a large number of peptides and rapid risk assessments for harmful blooms.
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Pilkaitytė, Renata, Donata Overlingė, Zita Rasuolė Gasiūnaitė, and Hanna Mazur-Marzec. "Spatial and Temporal Diversity of Cyanometabolites in the Eutrophic Curonian Lagoon (SE Baltic Sea)." Water 13, no. 13 (June 25, 2021): 1760. http://dx.doi.org/10.3390/w13131760.

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This work aims to determine the profiles of cyanopeptides and anatoxin synthetized by cyanobacteria in the Lithuanian part of the Curonian Lagoon (SE Baltic Sea) and to characterize their spatial and temporal patterns in this ecosystem. Cyanometabolites were analysed by a LC-MS/MS system and were coupled to a hybrid triple quadrupole/linear ion trap mass spectrometer. During the investigation period (2013–2017), 10 microcystins, nodularin, anatoxin-a, 16 anabaenopeptins, including 1 oscillamide, 12 aeruginosins, 1 aeruginosamide, 3 cyanopeptolins and 4 microginins were detected. The most frequently detected metabolites were found at all investigated sites. Demethylated microcystin variants and anabaenopeptins had the strongest relationship with Planktothrix agardhii, while non-demethylated microcystin variants and anatoxin had the strongest relationship with Microcystis spp. Low concentrations of some microcystins: [Asp3]MC-RR, MC-RR, MC-LR, as well as a few other cyanopeptides: AP-A and AEG-A were found during the cold period (December–March). Over the study period, Aphanizomenon, Planktothrix and Microcystis were the main dominant cyanobacteria species, while Planktothrix, Microcystis, and Dolichospermum were potentially producers of cyanopeptides and anatoxin detected in samples from the Curonian Lagoon.
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27

Brzuzan, Paweł, Hanna Mazur-Marzec, Maciej Florczyk, Filip Stefaniak, Anna Fidor, Robert Konkel, and Maciej Woźny. "Luciferase reporter assay for small-molecule inhibitors of MIR92b-3p function: Screening cyanopeptolins produced by Nostoc from the Baltic Sea." Toxicology in Vitro 68 (October 2020): 104951. http://dx.doi.org/10.1016/j.tiv.2020.104951.

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28

Tooming-Klunderud, Ave, Thomas Rohrlack, Kamran Shalchian-Tabrizi, Tom Kristensen, and Kjetill S. Jakobsen. "Structural analysis of a non-ribosomal halogenated cyclic peptide and its putative operon from Microcystis: implication for evolution of cyanopeptolins." Microbiology 155, no. 6 (June 1, 2009): 2106–8. http://dx.doi.org/10.1099/mic.0.30275-0.

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29

Tooming-Klunderud, Ave, Thomas Rohrlack, Kamran Shalchian-Tabrizi, Tom Kristensen, and Kjetill S. Jakobsen. "Structural analysis of a non-ribosomal halogenated cyclic peptide and its putative operon from Microcystis: implications for evolution of cyanopeptolins." Microbiology 153, no. 5 (May 1, 2007): 1382–93. http://dx.doi.org/10.1099/mic.0.2006/001123-0.

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30

Neumann, Uwe, Victoriano Campos, Sergio Cantarero, Homero Urrutia, Rita Heinze, Jürgen Weckesser, and Marcel Erhard. "Co-Occurrence of Non-toxic (Cyanopeptolin) and Toxic (Microcystin) Peptides in a Bloom of Microcystis sp. from a Chilean Lake." Systematic and Applied Microbiology 23, no. 2 (June 2000): 191–97. http://dx.doi.org/10.1016/s0723-2020(00)80004-1.

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31

Egli, Christine M., Regiane S. Natumi, Martin R. Jones, and Elisabeth M. L. Janssen. "Inhibition of Extracellular Enzymes Exposed to Cyanopeptides." CHIMIA International Journal for Chemistry 74, no. 3 (March 25, 2020): 122–28. http://dx.doi.org/10.2533/chimia.2020.122.

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Harmful cyanobacterial blooms in freshwater ecosystems produce bioactive secondary metabolites including cyanopeptides that pose ecological and human health risks. Only adverse effects of one class of cyanopeptides, microcystins, have been studied extensively and have consequently been included in water quality assessments. Inhibition is a commonly observed effect for enzymes exposed to cyanopeptides and has mostly been investigated for human biologically relevant model enzymes. Here, we investigated the inhibition of ubiquitous aquatic enzymes by cyanobacterial metabolites. Hydrolytic enzymes are utilized in the metabolism of aquatic organisms and extracellularly by heterotrophic bacteria to obtain assimilable substrates. The ubiquitous occurrence of hydrolytic enzymes leads to the co-occurrence with cyanopeptides especially during cyanobacterial blooms. Bacterial leucine aminopeptidase and alkaline phosphatase were exposed to cyanopeptide extracts of different cyanobacterial strains ( Microcystis aeruginosa wild type and microcystin-free mutant, Planktothrix rubescens) and purified cyanopeptides. We observed inhibition of aminopeptidase and phosphatase upon exposure, especially to the apolar fractions of the cyanobacterial extracts. Exposure to the dominant cyanopeptides in these extracts confirmed that purified microcystins, aerucyclamide A and cyanopeptolin A inhibit the aminopeptidase in the low mg L–1 range while the phosphatase was less affected. Inhibition of aquatic enzymes can reduce the turnover of nutrients and carbon substrates and may also impair metabolic functions of grazing organisms.
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32

Pearson, Leanne A., Nicholas D. Crosbie, and Brett A. Neilan. "Distribution and conservation of known secondary metabolite biosynthesis gene clusters in the genomes of geographically diverse Microcystis aeruginosa strains." Marine and Freshwater Research 71, no. 5 (2020): 701. http://dx.doi.org/10.1071/mf18406.

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The cyanobacterium Microcystis aeruginosa has been linked to toxic blooms worldwide. In addition to producing hepatotoxic microcystins, many strains are capable of synthesising a variety of biologically active compounds, including protease and phosphatase inhibitors, which may affect aquatic ecosystems and pose a risk to their use. This study explored the distribution, composition and conservation of known secondary metabolite (SM) biosynthesis gene clusters in the genomes of 27 M. aeruginosa strains isolated from six different Köppen–Geiger climates. Our analysis identified gene clusters with significant homology to nine SM biosynthesis gene clusters spanning four different compound classes: non-ribosomal peptides, hybrid polyketide–non-ribosomal peptides, cyanobactins and microviridins. The aeruginosin, microviridin, cyanopeptolin and microcystin biosynthesis gene clusters were the most frequently observed, but hybrid polyketide–non-ribosomal peptide biosynthesis clusters were the most common class overall. Although some biogeographic relationships were observed, taxonomic markers and geography were not reliable indicators of SM biosynthesis cluster distribution, possibly due to previous genetic deletions or horizontal gene transfer events. The only cyanotoxin biosynthesis gene cluster identified in our screening study was the microcystin synthetase (mcy) gene cluster, suggesting that the production of non-microcystin cyanotoxins by this taxon, such as anatoxin-a or paralytic shellfish poison analogues, is either absent or rare.
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33

Bojadzija Savic, Gorenka, Christine Edwards, Enora Briand, Linda Lawton, Claudia Wiegand, and Myriam Bormans. "Daphnia magna Exudates Impact Physiological and Metabolic Changes in Microcystis aeruginosa." Toxins 11, no. 7 (July 19, 2019): 421. http://dx.doi.org/10.3390/toxins11070421.

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While the intracellular function of many toxic and bioactive cyanobacterial metabolites is not yet known, microcystins have been suggested to have a protective role in the cyanobacterial metabolism, giving advantage to toxic over nontoxic strains under stress conditions. The zooplankton grazer Daphnia reduce cyanobacterial dominance until a certain density, which may be supported by Daphnia exudates, affecting the cyanobacterial physiological state and metabolites’ production. Therefore, we hypothesized that D. magna spent medium will impact the production of cyanobacterial bioactive metabolites and affect cyanobacterial photosynthetic activity in the nontoxic, but not the toxic strain. Microcystin (MC-LR and des-MC-LR) producing M. aeruginosa PCC7806 and its non-microcystin producing mutant were exposed to spent media of different D. magna densities and culture durations. D. magna spent medium of the highest density (200/L) cultivated for the shortest time (24 h) provoked the strongest effect. D.magna spent medium negatively impacted the photosynthetic activity of M. aeruginosa PCC7806, as well as the dynamics of intracellular and extracellular cyanobacterial metabolites, while its mutant was unaffected. In the presence of Daphnia medium, microcystin does not appear to have a protective role for the strain. On the contrary, extracellular cyanopeptolin A increased in M. aeruginosa PCC7806 although the potential anti-grazing role of this compound would require further studies.
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34

Faltermann, Susanne, Simon Hutter, Verena Christen, Timm Hettich, and Karl Fent. "Anti-Inflammatory Activity of Cyanobacterial Serine Protease Inhibitors Aeruginosin 828A and Cyanopeptolin 1020 in Human Hepatoma Cell Line Huh7 and Effects in Zebrafish (Danio rerio)." Toxins 8, no. 7 (July 14, 2016): 219. http://dx.doi.org/10.3390/toxins8070219.

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35

Toporowska, Magdalena, Hanna Mazur-Marzec, and Barbara Pawlik-Skowrońska. "The Effects of Cyanobacterial Bloom Extracts on the Biomass, Chl-a, MC and Other Oligopeptides Contents in a Natural Planktothrix agardhii Population." International Journal of Environmental Research and Public Health 17, no. 8 (April 22, 2020): 2881. http://dx.doi.org/10.3390/ijerph17082881.

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Blooms of the cyanobacterium Planktothrix agardhii are common in shallow, eutrophic freshwaters. P. agardhii may produce hepatotoxic microcystins (MCs) and many other bioactive secondary metabolites belonging mostly to non-ribosomal oligopeptides. The aim of this work was to study the effects of two extracts (Pa-A and Pa-B) of P. agardhii-predominated bloom samples with different oligopeptide profiles and high concentration of biogenic compounds on another natural P. agardhii population. We hypothesised that the P. agardhii biomass and content of oligopeptides in P. agardhii is shaped in a different manner by diverse mixtures of metabolites of different P. agardhii-dominated cyanobacterial assemblages. For this purpose, the biomass, chlorophyll a and oligopeptides content in the treated P. agardhii were measured. Seven-day microcosm experiments with four concentrations of the extracts Pa-A and Pa-B were carried out. Generally, aeruginosins (AERs), cyanopeptolins (CPs) and anabaenopeptins (APs) were the most numerous peptides; however, only 16% of them were common for both extracts. The addition of the extracts resulted in similar effects on P. agardhii: an increase in biomass, Chl-a and MC content in the exposed P. agardhii as well as changes in its oligopeptide profile were observed. MCs present in the extracts did not inhibit accumulation of P. agardhii biomass, and did not have any negative effect on MC and Chl-a content. No evidence for bioaccumulation of dissolved peptides in the P. agardhii exposed was found. As the two tested extracts differed considerably in oligopeptide composition, but contained similar high concentrations of nutrients, it seems that biogenic compounds, not oligopeptides themselves, positively influenced the mixed natural P. agardhii population.
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Welker, Martin, Matthias Brunke, Karina Preussel, Indra Lippert, and Hans von Döhren. "Diversity and distribution of Microcystis (Cyanobacteria) oligopeptide chemotypes from natural communities studied by single-colony mass spectrometry." Microbiology 150, no. 6 (June 1, 2004): 1785–96. http://dx.doi.org/10.1099/mic.0.26947-0.

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Microcystis sp. has been recognized in recent years as a producer of a high number of secondary metabolites. Among these, peptides that are produced by the non-ribosomal peptide synthetase pathway often show bioactivity or are toxic to humans. The production of particular peptides is specific for individual Microcystis clones, allowing their characterization as chemotypes by analysing the peptidome. The authors studied the in situ diversity of peptides and chemotypes in Microcystis communities from lakes in and around Berlin, Germany, by direct analysis of individual colonies by MALDI-TOF mass spectrometry. From 165 colonies analysed a total of 46 individual peptides could be identified, 21 of which have not been described previously. For six of the new peptides the structures could be elucidated from fragment patterns, while for others only a preliminary classification could be achieved. In most colonies, two to ten individual peptides were detected. In 19 colonies, 16 of which were identified as M. wesenbergii, no peptide metabolites could be detected. The peptide data of 146 colonies were subjected to an ordination (principal components analysis). The principal components were clearly formed by the microcystin variants Mcyst-LR, -RR and -YR, anabaenopeptins B and E/F, a putative microviridin, and a new cyanopeptolin. In the resulting ordination plots most colonies were grouped into five distinct groups, while 40 colonies scattered widely outside these groups. In some cases colonies from different lakes clustered closely, indicating the presence of similar chemotypes in the respective samples. With respect to colony morphology no clear correlation between a chemotype and a morphospecies could be established, but M. aeruginosa, for example, was found to produce predominantly microcystins. In contrast, M. ichthyoblabe colonies were mostly negative for microcystins and instead produced anabaenopeptins. The number of peptides detected in a limited number of samples and the various combinations of peptides in individual Microcystis colonies highlights the immense metabolic potential and diversity of this genus.
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37

Zastepa, Arthur, Todd R. Miller, L. Cynthia Watson, Hedy Kling, and Susan B. Watson. "Toxins and Other Bioactive Metabolites in Deep Chlorophyll Layers Containing the Cyanobacteria Planktothrix cf. isothrix in Two Georgian Bay Embayments, Lake Huron." Toxins 13, no. 7 (June 27, 2021): 445. http://dx.doi.org/10.3390/toxins13070445.

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The understanding of deep chlorophyll layers (DCLs) in the Great Lakes—largely reported as a mix of picoplankton and mixotrophic nanoflagellates—is predominantly based on studies of deep (>30 m), offshore locations. Here, we document and characterize nearshore DCLs from two meso-oligotrophic embayments, Twelve Mile Bay (TMB) and South Bay (SB), along eastern Georgian Bay, Lake Huron (Ontario, Canada) in 2014, 2015, and 2018. Both embayments showed the annual formation of DCLs, present as dense, thin, metalimnetic plates dominated by the large, potentially toxic, and bloom-forming cyanobacteria Planktothrix cf. isothrix. The contribution of P. cf. isothrix to the deep-living total biomass (TB) increased as thermal stratification progressed over the ice-free season, reaching 40% in TMB (0.6 mg/L at 9.5 m) and 65% in South Bay (3.5 mg/L at 7.5 m) in 2015. The euphotic zone in each embayment extended down past the mixed layer, into the nutrient-enriched hypoxic hypolimnia, consistent with other studies of similar systems with DCLs. The co-occurrence of the metal-oxidizing bacteria Leptothrix spp. and bactivorous flagellates within the metalimnetic DCLs suggests that the microbial loop plays an important role in recycling nutrients within these layers, particularly phosphate (PO4) and iron (Fe). Samples taken through the water column in both embayments showed measurable concentrations of the cyanobacterial toxins microcystins (max. 0.4 µg/L) and the other bioactive metabolites anabaenopeptins (max. ~7 µg/L) and cyanopeptolins (max. 1 ng/L), along with the corresponding genes (max. in 2018). These oligopeptides are known to act as metabolic inhibitors (e.g., in chemical defence against grazers, parasites) and allow a competitive advantage. In TMB, the 2018 peaks in these oligopeptides and genes coincided with the P. cf. isothrix DCLs, suggesting this species as the main source. Our data indicate that intersecting physicochemical gradients of light and nutrient-enriched hypoxic hypolimnia are key factors in supporting DCLs in TMB and SB. Microbial activity and allelopathy may also influence DCL community structure and function, and require further investigation, particularly related to the dominance of potentially toxigenic species such as P. cf. isothrix.
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38

Choi, Hyukjae, Sun Kwan Oh, Wonho Yih, Jungwook Chin, Heonjoong Kang, and Jung-Rae Rho. "ChemInform Abstract: Cyanopeptoline CB071: A Cyclic Depsipeptide Isolated from the Freshwater Cyanobacterium Aphanocapsa sp." ChemInform 40, no. 3 (January 20, 2009). http://dx.doi.org/10.1002/chin.200903196.

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39

McDonald, Kimberlynn, Justin B. Renaud, Frances R. Pick, J. David Miller, Mark W. Sumarah, and David R. McMullin. "Diagnostic Fragmentation Filtering for Cyanopeptolin Detection." Environmental Toxicology and Chemistry, November 25, 2020. http://dx.doi.org/10.1002/etc.4941.

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40

Matern, Ute, Lukas Oberer, Marcel Erhard, Michael Herdman, and Juergen Weckesser. "Hofmannolin, a Cyanopeptolin from Scytonema hofmanni PCC 7110." ChemInform 35, no. 10 (March 9, 2004). http://dx.doi.org/10.1002/chin.200410177.

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41

Filatova, Daria, Martin R. Jones, John A. Haley, Oscar Núñez, Marinella Farré, and Elisabeth M. L. Janssen. "Cyanobacteria and their secondary metabolites in three freshwater reservoirs in the United Kingdom." Environmental Sciences Europe 33, no. 1 (March 9, 2021). http://dx.doi.org/10.1186/s12302-021-00472-4.

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Abstract Background Bloom-forming cyanobacteria occur globally in aquatic environments. They produce diverse bioactive metabolites, some of which are known to be toxic. The most studied cyanobacterial toxins are microcystins, anatoxin, and cylindrospermopsin, yet more than 2000 bioactive metabolites have been identified to date. Data on the occurrence of cyanopeptides other than microcystins in surface waters are sparse. Results We used a high-performance liquid chromatography–high-resolution tandem mass spectrometry/tandem mass spectrometry (HPLC–HRMS/MS) method to analyse cyanotoxin and cyanopeptide profiles in raw drinking water collected from three freshwater reservoirs in the United Kingdom. A total of 8 cyanopeptides were identified and quantified using reference standards. A further 20 cyanopeptides were identified based on a suspect-screening procedure, with class-equivalent quantification. Samples from Ingbirchworth reservoir showed the highest total cyanopeptide concentrations, reaching 5.8, 61, and 0.8 µg/L in August, September, and October, respectively. Several classes of cyanopeptides were identified with anabaenopeptins, cyanopeptolins, and microcystins dominating in September with 37%, 36%, and 26%, respectively. Samples from Tophill Low reservoir reached 2.4 µg/L in September, but remained below 0.2 µg/L in other months. Samples from Embsay reservoir did not exceed 0.1 µg/L. At Ingbirchworth and Tophill Low, the maximum chlorophyll-a concentrations of 37 µg/L and 22 µg/L, respectively, and cyanobacterial count of 6 × 104 cells/mL were observed at, or a few days after, peak cyanopeptide concentrations. These values exceed the World Health Organization’s guideline levels for relatively low probability of adverse health effects, which are defined as 10 µg/L chlorophyll-a and 2 × 104 cells/mL. Conclusions This data is the first to present concentrations of anabaenopeptins, cyanopeptolins, aeruginosins, and microginins, along with microcystins, in U.K. reservoirs. A better understanding of those cyanopeptides that are abundant in drinking water reservoirs can inform future monitoring and studies on abatement efficiency during water treatment.
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Bober, Beata, Ewelina Chrapusta-Srebrny, and Jan Bialczyk. "Novel cyanobacterial metabolites, cyanopeptolin 1081 and anabaenopeptin 899, isolated from an enrichment culture dominated by Woronichinia naegeliana (Unger) Elenkin." European Journal of Phycology, October 14, 2020, 1–11. http://dx.doi.org/10.1080/09670262.2020.1813809.

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43

Jacinavicius, Fernanda Rios, Vanessa Geraldes, Camila M. Crnkovic, Endrews Delbaje, Marli F. Fiore, and Ernani Pinto. "Effect of ultraviolet radiation on the metabolomic profiles of potentially toxic cyanobacteria." FEMS Microbiology Ecology 97, no. 1 (November 26, 2020). http://dx.doi.org/10.1093/femsec/fiaa243.

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ABSTRACT Interactions between climate change and ultraviolet radiation (UVR) have a substantial impact on aquatic ecosystems, especially on photosynthetic organisms. To counteract the damaging effects of UVR, cyanobacteria developed adaptive strategies such as the biosynthesis of secondary metabolites. This study aimed to evaluate the effects of UVR on the metabolomic profiles of potentially toxic cyanobacteria. Twelve strains were irradiated with ultraviolet A and ultraviolet B radiation and parabolic aluminized reflector lamps for 3 days, followed by liquid chromatography–tandem mass spectometry (LC-MS/MS) analysis to assess changes in metabolomic profiles. Matrices were used to generate principal component analysis biplots, and molecular networks were obtained using the Global Natural Products platform. Most strains showed significant changes in their metabolomic profiles after UVR exposure. On average, 7% of MS features were shown to be exclusive to metabolomic profiles before UVR exposure, while 9% were unique to metabolomic profiles after UVR exposure. The identified compounds included aeruginosins, spumigins, cyanopeptolins, microginins, namalides, pseudospumigins, anabaenopeptins, mycosporine-like amino acids, nodularins and microcystins. Data showed that cyanobacteria display broad metabolic plasticity upon UVR exposure, including the synthesis and differential expression of a variety of secondary metabolites. This could result in a competitive advantage, supporting cyanobacterial blooms under various UVR light exposures.
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44

Natumi, Regiane, Sandro Marcotullio, and Elisabeth M. L. Janssen. "Phototransformation kinetics of cyanobacterial toxins and secondary metabolites in surface waters." Environmental Sciences Europe 33, no. 1 (March 1, 2021). http://dx.doi.org/10.1186/s12302-021-00465-3.

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Abstract Background Cyanobacteria and their toxins occur in high concentrations during the so-called bloom events in surface waters. To be able to assess the risks associated with cyanobacterial blooms, we need to understand the persistence and fate processes of these toxins and other bioactive metabolites. In this study, we investigated the photochemical fate of 54 cyanopeptides extracted from two strains of Microcystis aeruginosa (PCC7806 and UV006), Planktothrix rubescens, and Dolichospermum flos aquae. We determined half-lives during sunlight exposure in lake water and inspected the effect of pH on transformation kinetics for 27 microcystins, 8 anabaenopeptins, 14 cyanopeptolins, 2 cyclamides, and 3 aeruginosins. Results For cyanopeptides from D. flos aquae and P. rubescens, we observed the highest removal of 28 and 26%, respectively, after 3-h sunlight exposure. Most cyanopeptides produced by the two M. aeruginosa strains were rather persistent with only up to 3% removal. The more reactive cyanopeptides contained amino acids known to undergo phototransformation, including methionine and tyrosine moieties or their derivatives. Photochemical half-lives of 14 tyrosine-containing cyanopeptides decreased by one order of magnitude from nearly persistent conditions at pH 7 (half-life > 70 h) to shorter half-lives at pH 10 (< 10 h). Conclusions More work is needed to distinguish the contribution of different photochemical reaction pathways including the contributions to the pH effect. To the best of our knowledge, this is the first assessment of transformation kinetics of such a wide range of cyanopeptides. The abundant and persistent cyanopeptides that have not been studied in detail yet should be prioritized for the evaluation of their ecosystem and human health risks and for their abatement during drinking water treatment.
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Harke, Matthew J., Jennifer G. Jankowiak, Brooke K. Morrell, and Christopher J. Gobler. "Transcriptomic Responses in the Bloom-Forming Cyanobacterium Microcystis Induced during Exposure to Zooplankton." Applied and Environmental Microbiology 83, no. 5 (December 21, 2016). http://dx.doi.org/10.1128/aem.02832-16.

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ABSTRACT The bloom-forming, toxic cyanobacterium Microcystis synthesizes multiple secondary metabolites and has been shown to deter zooplankton grazing. However, the biochemical and/or molecular basis by which Microcystis deters zooplankton remains unclear. This global transcriptomic study explored the response of Microcystis to direct and indirect exposures to multiple densities of two cladoceran grazers, Daphnia pulex and D. magna. Higher densities of both daphnids significantly reduced Microcystis cell densities and elicited a stronger transcriptional response in Microcystis. While many putative grazer deterrence genes (encoding microcystin, aeruginosin, cyanopeptolin, and microviridin) were largely unaffected by zooplankton, transcripts for heat shock proteins (hsp) increased in abundance. Beyond metabolites and hsp, large increases in the abundances of transcripts from photosynthetic processes were observed, evidencing energy acquisition pathways were stimulated by grazing. In addition, transcripts of genes associated with the production of extracellular polysaccharides and gas vesicles significantly increased in abundance. These genes have been associated with colony formation and may have been invoked to deter grazers. Collectively, this study demonstrates that daphnid grazers induce a significant transcriptomic response in Microcystis, suggesting this cyanobacterium upregulates specific biochemical pathways to adapt to predation. IMPORTANCE This work explores the transcriptomic responses of Microcystis aeruginosa following exposure to grazing by two cladocerans, Daphnia magna and D. pulex. Contrary to previous hypotheses, Microcystis did not employ putative grazing deterrent secondary metabolites in response to the cladocerans, suggesting they may have other roles within the cell, such as oxidative stress protection. The transcriptional metabolic signature during intense grazing was largely reflective of a growth and stress response, although increasing abundances of transcripts encoding extracellular polysaccharides and gas vesicles were potentially related to predator avoidance.
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