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The cyanobacterial metabolite nocuolin A is a natural oxadiazine that triggers apoptosis in human cancer cells
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SYSNO ASEP 0479204 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název The cyanobacterial metabolite nocuolin A is a natural oxadiazine that triggers apoptosis in human cancer cells Tvůrce(i) Voráčová, K. (CZ)
Hájek, J. (CZ)
Mareš, Jan (BU-J) RID
Urajová, P. (CZ)
Kuzma, M. (CZ)
Cheel, J. (CZ)
Villunger, A. (AT)
Kapuscik, A. (CZ)
Bally, M. (CA)
Novák, P. (CZ)
Kabeláč, M. (CZ)
Krumschnabel, G. (AT)
Lukeš, M. (CZ)
Voloshko, L. (RU)
Kopecký, J. (CZ)
Hrouzek, P. (CZ)Číslo článku e0172850 Zdroj.dok. PLoS ONE. - : Public Library of Science - ISSN 1932-6203
Roč. 12, č. 3 (2017)Poč.str. 20 s. Jazyk dok. eng - angličtina Země vyd. US - Spojené státy americké Klíč. slova secondary metabolite ; cancer ; non-ribosomal synthetase Vědní obor RIV EE - Mikrobiologie, virologie Obor OECD Microbiology Institucionální podpora BU-J - RVO:67985939 UT WOS 000396011300042 EID SCOPUS 85014240038 DOI 10.1371/journal.pone.0172850 Anotace Oxadiazines are heterocyclic compounds containing N-N-O or N-N-C-O system within a six membered ring. These structures have been up to now exclusively prepared via organic synthesis. Here, we report the discovery of a natural oxadiazine nocuolin A (NoA) that has a unique structure based on 1,2,3-oxadiazine. We have identified this compound in three independent cyanobacterial strains of genera Nostoc, Nodularia, and Anabaena and recognized the putative gene clusters for NoA biosynthesis in their genomes. Its structure was characterized using a combination of NMR, HRMS and FTIR methods. The compound was first isolated as a positive hit during screening for apoptotic inducers in crude cyanobacterial extracts. We demonstrated that NoA-induced cell death has attributes of caspase-dependent apoptosis. Moreover, NoA exhibits a potent anti-proliferative activity (0.7±4.5 μM) against several human cancer lines, with p53-mutated cell lines being even more sensitive. Since cancers bearing p53 mutations are resistant to several conventional anti-cancer drugs, NoA may offer a new scaffold for the development of drugs that have the potential to target tumor cells independent of their p53 status. As no analogous type of compound was previously described in the nature, NoA establishes a novel class of bioactive secondary metabolites. Pracoviště Botanický ústav Kontakt Martina Bartošová, martina.bartosova@ibot.cas.cz, ibot@ibot.cas.cz, Tel.: 271 015 242 ; Marie Jakšová, marie.jaksova@ibot.cas.cz, Tel.: 384 721 156-8 Rok sběru 2018
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