ArticlePloS one2017
The cyanobacterial metabolite nocuolin a is a natural oxadiazine that triggers apoptosis in human cancer cells.
Article in PloS one, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 63 citations in OpenAlex.
- Natural Products as Promising Pharmacological Agents Against Cancer: A Holistic Overview of Their Anti-Cancer Mechanisms of Action of the Last Five Years.Pharmaceuticals (Basel, Switzerland) · 2026Review
- Phycocompounds from Cyanobacteria: Exploring Synergistic Effects with Conventional Anticancer and Antimicrobial Properties.ACS omega · 2025Review
- The Cyanobacterial Oxadiazine Nocuolin A Shows Broad-Spectrum Toxicity Against Protozoans and the Nematode C. elegans.Microbial ecology · 2025Article
- Chemical diversity of cyanobacterial natural products.Natural product reports · 2025Review
- Isolation of Nocuolin A and Synthesis of New Oxadiazine Derivatives. Design, Synthesis, Molecular Docking, Apoptotic Evaluation, and Cathepsin B Inhibition.Marine drugs · 2023Article
- Emerging Trends of Nanotechnology and Genetic Engineering in Cyanobacteria to Optimize Production for Future Applications.Life (Basel, Switzerland) · 2022Review
- Biosynthesis of the Unusual Carbon Skeleton of Nocuolin A.ACS chemical biology · 2022Article
- Research Progresses on the Physiological and Pharmacological Benefits of Microalgae-Derived Biomolecules.Foods (Basel, Switzerland) · 2022Review
- Draft genome sequence of the cyanobacterium Sphaerospermopsis aphanizomenoides BCCUSP55 from the Brazilian semiarid region reveals potential for anti-cancer applications.Archives of microbiology · 2021Article
- Article
- Discovery of Cyanobacterial Natural Products Containing Fatty Acid Residues*.Angewandte Chemie (International ed. in English) · 2021Article
- Biosynthesis of Chlorinated Lactylates inJournal of natural products · 2021Article
- Cyanobacteria as Natural Therapeutics and Pharmaceutical Potential: Role in Antitumor Activity and as Nanovectors.Molecules (Basel, Switzerland) · 2021Review
- The Cytotoxic and Apoptotic Effects of the Brown AlgaeMolecules (Basel, Switzerland) · 2020Article
- Alternative Biosynthetic Starter Units Enhance the Structural Diversity of Cyanobacterial Lipopeptides.Applied and environmental microbiology · 2019Article
- New Drugs from the Sea: Pro-Apoptotic Activity of Sponges and Algae Derived Compounds.Marine drugs · 2019Review
- Antiproliferative Effects of the Natural Oxadiazine Nocuolin A Are Associated With Impairment of Mitochondrial Oxidative Phosphorylation.Frontiers in oncology · 2019Article
- Calothrixamides A and B from the Cultured Cyanobacterium Calothrix sp. UIC 10520.Journal of natural products · 2018Article
- Developments of Cyanobacteria for Nano-Marine Drugs: Relevance of Nanoformulations in Cancer Therapies.Marine drugs · 2018Review
- Highly divergent 16S rRNA sequences in ribosomal operons of Scytonema hyalinum (Cyanobacteria).PloS one · 2017Article
Corrections and comments
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Authors and funding
16 authors at 6 institutions in 4 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
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.
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