# Cyanopeptolin > Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Cyanopeptolin > Markdown URL: https://mediated.wiki/source/Cyanopeptolin.md > Source: https://en.wikipedia.org/wiki/Cyanopeptolin > Source revision: 1311599255 > License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/) {{Short description|Poisonous biological substance}} '''Cyanopeptolins''' (CPs) are a class of [oligopeptide](/source/oligopeptide)s produced by [Microcystis](/source/Microcystis) and [Planktothrix](/source/Planktothrix) algae strains, and can be [neurotoxic](/source/neurotoxin).{{cite journal|title=Molecular effects of the cyanobacterial toxin cyanopeptolin (CP1020) occurring in algal blooms: Global transcriptome analysis in zebrafish embryos|date=April 2014|author=Susanne Faltermann |author2=Sara Zucchi |author3=Esther Kohler |author4=Judith F. Blom |author5=Jakob Pernthaler |author6=Karl Fent |doi=10.1016/j.aquatox.2014.01.018|pmid=24561424|volume=149|journal=Aquatic Toxicology|pages=33–39|url=https://www.zora.uzh.ch/id/eprint/106906/1/Faltermann%20et%20al_140111_rev.pdf}}{{cite journal|title=Multiple Toxin Production in the Cyanobacterium Microcystis: Isolation of the Toxic Protease Inhibitor Cyanopeptolin 1020|year=2010|journal=J. Nat. Prod.|author=Karl Gademann|author2=Cyril Portmann|author3=Judith F. Blom|author4=Michael Zeder|author5=Friedrich Jüttner|doi=10.1021/np900818c|pmid=20405925|volume=73|issue=5|pages=980–984|url=http://www.zora.uzh.ch/id/eprint/46453/4/JNP_2010_Gademann_Blom_V.pdf|access-date=2019-07-14|archive-date=2022-02-02|archive-url=https://web.archive.org/web/20220202221752/https://www.zora.uzh.ch/id/eprint/46453/4/JNP_2010_Gademann_Blom_V.pdf|url-status=dead}}{{cite journal|title=Cyanobacterial peptides – Nature's own combinatorial biosynthesis|year=2006|journal=FEMS Microbiology Reviews|author1=Martin Welker |author2=Hans Von Döhren |doi=10.1111/j.1574-6976.2006.00022.x|pmid=16774586|volume=30|issue = 4|pages=530–563|doi-access=free}} The production of cyanopeptolins occurs through [nonribosomal peptide](/source/nonribosomal_peptide)s synthases (NRPS).{{cite journal|title=Limited Stability of Microcystins in Oligopeptide Compositions of Microcystis aeruginosa (Cyanobacteria): Implications in the Definition of Chemotypes|year=2013|journal=Toxins|author1=Ramsy Agha |author2=Samuel Cirés |author3=Lars Wörmer |author4=Antonio Quesada |doi=10.3390/toxins5061089|pmid=23744054|pmc=3717771|volume=5|issue=6|pages=1089–1104|doi-access=free }} == Chemistry == CPs are, in general, a six-residue peptide formed into a ring by a beta-[lactone](/source/lactone) bridge,{{cite journal |last1=Janssen |first1=Elisabeth M.-L. |title=Cyanobacterial peptides beyond microcystins – A review on co-occurrence, toxicity, and challenges for risk assessment |journal=Water Research |date=March 2019 |volume=151 |pages=488–499 |doi=10.1016/j.watres.2018.12.048 |pmid=30641464 |doi-access=free}} making them chemically depsipeptides (peptidolactones). The first position is usually [threonine](/source/threonine), which links to one or two residues via an ester bound on the beta-hydroxyl group; the third position is conserved to be 3-amino-6-hydroxy-2-piperidone (Ahp) or a derivative. All other positions are highly variable.{{cite journal |last1=Mazur-Marzec |first1=Hanna |last2=Fidor |first2=Anna |last3=Cegłowska |first3=Marta |last4=Wieczerzak |first4=Ewa |last5=Kropidłowska |first5=Magdalena |last6=Goua |first6=Marie |last7=Macaskill |first7=Jenny |last8=Edwards |first8=Christine |title=Cyanopeptolins with Trypsin and Chymotrypsin Inhibitory Activity from the Cyanobacterium Nostoc edaphicum CCNP1411 |journal=Marine Drugs |date=26 June 2018 |volume=16 |issue=7 |page=220 |doi=10.3390/md16070220 |pmid=29949853 |pmc=6070996 |doi-access=free}} There is not a single, unified nomenclature, for CPs. Names such as CP1020{{cite web |title=Cyanopeptolin CP1020 |url=https://pubchem.ncbi.nlm.nih.gov/compound/Cyanopeptolin-CP1020 |website=pubchem.ncbi.nlm.nih.gov |language=en}} and CP1138 refer to the [molar mass](/source/molar_mass). Others, such as aeruginopeptins, micropeptins, microcystilide, nostopeptins, and oscillapeptins, refer to the organism the substance is originally found in. ==Factors affecting production== Increased water temperatures, because of [climate change](/source/climate_change) and [eutrophication](/source/eutrophication) of inland waters promote blooms of [cyanobacteria](/source/cyanobacteria), potentially threaten water contamination by the production of the toxic cyanopeptolin CP1020. ==Biological activity== Most CPs are [serine protease](/source/serine_protease) [inhibitor](/source/Protease_inhibitor_(biology))s. Cyanopeptolin CP1020 exposure in [zebrafish](/source/zebrafish) affected pathways related to DNA damage, the [circadian rhythm](/source/circadian_rhythm) and response to light. == Evolutionary history == CPs are probably very ancient: the cyanobacterial genera that produce CPs appear to have inherited the key modules vertically and not horizontally.{{cite journal |last1=Rounge |first1=Trine B. |last2=Rohrlack |first2=Thomas |last3=Tooming-Klunderud |first3=Ave |last4=Kristensen |first4=Tom |last5=Jakobsen |first5=Kjetill S. |title=Comparison of Cyanopeptolin Genes in Planktothrix, Microcystis, and Anabaena Strains: Evidence for Independent Evolution within Each Genus |journal=Applied and Environmental Microbiology |date=15 November 2007 |volume=73 |issue=22 |pages=7322–7330 |doi=10.1128/AEM.01475-07|pmid=17921284 |pmc=2168201 |bibcode=2007ApEnM..73.7322R }} ==See also== *[Cyanotoxin](/source/Cyanotoxin) *[Microviridin](/source/Microviridin) *[Microcystin](/source/Microcystin) ==References== {{reflist|2}} ==External links== * [https://www.nytimes.com/2014/08/07/science/cyanobacteria-are-far-from-just-toledos-problem.html?_r=0 Cyanobacteria, and toxin production (The New York Times)] {{Cyanotoxins}} Category:Peptides Category:Cyanotoxins --- Adapted from the Wikipedia article [Cyanopeptolin](https://en.wikipedia.org/wiki/Cyanopeptolin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Cyanopeptolin?action=history)). 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