ArticleTetrahedron2012
Nitrile-Containing Fischerindoles from the Cultured Cyanobacterium Fischerella sp.
Article in Tetrahedron, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 38 citations in OpenAlex.
- Chemical diversity of cyanobacterial natural products.Natural product reports · 2025Review
- Naturally Occurring Organohalogen Compounds-A Comprehensive Review.Progress in the chemistry of organic natural products · 2023Review
- Recent advances in hapalindole-type cyanobacterial alkaloids: biosynthesis, synthesis, and biological activity.Natural product reports · 2021Review
- Bacterial terpenome.Natural product reports · 2021Review
- Article
- Halogenation-Guided Chemical Screening Provides Insight into Tjipanazole Biosynthesis by the Cyanobacterium Fischerella ambigua.Chembiochem : a European journal of chemical biology · 2020Article
- Natural Products from Cyanobacteria: Focus on Beneficial Activities.Marine drugs · 2019Review
- Total Synthesis of Pentacyclic (-)-Ambiguine P Using Sequential Indole Functionalizations.Journal of the American Chemical Society · 2019Article
- Structural Diversity, Biological Properties and Applications of Natural Products from Cyanobacteria. A Review.Marine drugs · 2017Review
- Decoding cyclase-dependent assembly of hapalindole and fischerindole alkaloids.Nature chemical biology · 2017Article
- Indole Alkaloids of the Stigonematales (Cyanophyta): Chemical Diversity, Biosynthesis and Biological Activity.Marine drugs · 2016Review
- Genome mining for natural product biosynthetic gene clusters in the Subsection V cyanobacteria.BMC genomics · 2015Article
- Review
- Scalable Total Syntheses of (-)-Hapalindole U and (+)-Ambiguine H.Tetrahedron · 2015Article
- Indole alkaloids from Fischerella inhibit vertebrate development in the zebrafish (Danio rerio) embryo model.Toxins · 2014Article
- Indole alkaloids from two cultured cyanobacteria, Westiellopsis sp. and Fischerella muscicola.Bioorganic & medicinal chemistry · 2012Article
- Chemical Diversity of Metabolites from Fungi, Cyanobacteria, and Plants Relative to FDA-Approved Anticancer Agents.ACS medicinal chemistry letters · 2012Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
Abstract
Chemical investigation of the cultured cyanobacterium Fischerella sp. (SAG strain number 46.79) led to the isolation of four nitrile-containing indole alkaloids, namely 12-epi-fischerindole I nitrile (1), deschloro 12-epi-fischerindole I nitrile (2), 12-epi-fischerindole W nitrile (3), and deschloro 12-epi-fischerindole W nitrile (4) along with a known metabolite hapalosin. The structures were determined by detailed spectroscopic analyses on the basis of 1D and 2D NMR and HRESIMS data. All isolates were evaluated for cytotoxicity against human cancer cells and for 20S proteasome inhibition. Deschloro 12-epi-fischerindole I nitrile (2) was found to be weakly cytotoxic against HT-29 cells with an ED(50) value of 23 μM. Hapalosin showed weak cytotoxicity against HT-29 and MCF-7 cells with ED(50) values of 22 and 27 μM, respectively, as well as moderate 20S proteasome inhibition with an IC(50) value of 12 μM. Compounds 1-4 all contain a nitrile moiety instead of the isonitrile found in all fischerindoles reported to date. Compounds 3 and 4 also display a new carbon skeleton, in which a six-membered ring replaces the five-membered ring normally found in fischerindole-type alkaloids.
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.