Cited by 378Aquatic Ecosystems and Phytoplankton DynamicsMicrobial Natural Products and BiosynthesisMarine Toxins and Detection Methods

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Anatoxin-a, a toxic alkaloid from Anabaena flos-aquae NRC-44h

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Devlin, J. P., Edwards, O. E., Gorham, P. R., Hunter, N. R., Pike, R. K., Stavric, B.·1977·Canadian Journal of Chemistry

DOI 10.1139/v77-189

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Abstract

A toxic alkaloid, anatoxin-a, has been isolated from mass cultures of a unialgal clone, NRC-44h, of the freshwater blue-green algae Anabaena flos-aquae (Lyngb.) de Bréb., and its structure determined.

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Algae, Man and the Environment
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FIRST REPORT OF THE CYANOTOXIN ANATOXIN‐A FROM APHANIZOMENON ISSATSCHENKOI (CYANOBACTERIA)1
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“ene) and its methylene homologue homoanatoxin-a (HANTX) (2-(propan-1-oxo-1-yl)-9-azabicyclo[4.2.1]non- 2-ene) ( Devlin et al., 1977; Skulberg et al., 1992), are lowmolecular-mass bicyclic secondary amines synthesized by some planktonic and benthic strains of the genera Anabaena, Oscillatoria, Aphanizomenon and Cylindr…”
BackgroundInfluential
Anatoxins from clones of Anabaena flos-aquae isolated from lakes of western Canada
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Self-citation
Appendix 2: Cyanobacteria Associated With the Production of Cyanotoxins
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EFFECT OF CULTURE AND BLOOM DEVELOPMENT AND OF SAMPLE STORAGE ON PARALYTIC SHELLFISH POISONS IN THE CYANOBACTERIUM ANABAENA CIRCINALIS
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Application of Intramolecular Enyne Metathesis to the Synthesis of Aza[4.2.1]bicyclics: Enantiospecific Total Synthesis of (+)-Anatoxin-a
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Saxitoxins (PSP toxins) in Danish lakes
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Guanitoxin, re-naming a cyanobacterial organophosphate toxin
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“…flos-aquae, Ana. spiroides, Ana. planctonica, Aphanizomenon flos-aquae, Microcystis aeruginosa, Cylindrospermum sp., Planktothrix agardhii and P. rubescens (Huber 1972, Devlin et al. 1977, Sivonen et al. 1989, Edwards et al. 1992, Skulberg et al. 1992, Park et al. 1993, Rapala et al. 1993).”
Background
Impacts of microbial assemblage and environmental conditions on the distribution of anatoxin-a producing cyanobacteria within a river network
Bouma‐Gregson, K., Olm, M. R., Probst, A. J., Anantharaman, K., Power, M. E., & Banfield, J. F. (2019) · The ISME Journal · doi:10.1038/s41396-019-0374-3 · Cited by 88
“Anatoxin-a is a neurotoxic alkaloid that inhibits neuromuscular nicotinic acetylcholine receptors by disrupting cellular ion channels, which causes muscle failure and can lead to death [32, 33].”
Background
The use of miniaturized algal bioassays in comparison to the standard flask assay
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“The two pharmacologically most important naturally-occurring homotropane nicotinic agonists are anatoxin-a 1 [9,18] and homoanatoxin 2 [19,20,21] (Figure 1), and these alkaloids, together with their derivatives, form the primary focus of this review.”
Background
Liquid chromatography/mass spectrometric detection of anatoxin-a, a neurotoxin from cyanobacteria
Harada, K., Nagai, H., Kimura, Y., Suzuki, M., Park, H.-D., Watanabe, M. F., Luukkainen, R., Sivonen, K., & Carmichael, W. W. (1993) · Tetrahedron · doi:10.1016/0040-4020(93)80011-h · Cited by 81
Algal Toxins
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Biogenetic Diversity of Cyanobacterial Metabolites
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Anatoxin-a: Overview on a harmful cyanobacterial neurotoxin from the environmental scale to the molecular target
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Synthetic approaches to anatoxin-a
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A new procedure for the analysis and purification of naturally occurring anatoxin-a from the blue-green alga Anabaena flos-aquae
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Acute effects of an anatoxin-a producing cyanobacterium on juvenile fish—Cyprinus carpio L.
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“Among the neurotoxins, anatoxin-a is one of the most common worldwide, being reported in countries such as Canada (Devlin et al., 1977), USA (Stevens and Krieger, 1991), Scotland (Edwards et al.”
Background
Enantioselective synthesis of (+)-anatoxin-a via enyne metathesis
Brenneman, J. B., Machauer, R., & Martin, S. F. (2004) · Tetrahedron · doi:10.1016/j.tet.2004.06.021 · Cited by 74
Liquid chromatography with electrospray ion‐trap mass spectrometry for the determination of anatoxins in cyanobacteria and drinking water
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Gold‐ and Silver‐Catalyzed Tandem Amination/Ring Expansion of Cyclopropyl Methanols with Sulfonamides as an Expedient Route to Pyrrolidines
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Hierridin B and 2,4-dimethoxy-6-heptadecyl-phenol, secondary metabolites from the cyanobacterium Phormidium ectocarpi with antiplasmodial activity
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Authors: Devlin, J. P., Edwards, O. E., Gorham, P. R., Hunter, N. R., Pike, R. K., & Stavric, B.
ORCID: Devlin, J. P.
Venue: Canadian Journal of Chemistry
Publisher: Canadian Science Publishing
Published: 1977-04-15
Volume: 55
Issue: 8
Pages: 1367-1371
ISSN: 0008-4042 (ISSN-L)
1480-3291
DOI: 10.1139/v77-189
OpenAlex: W2015312835
Cited by: 378
References: 1
Citations by year: 2026: 4 · 2025: 7 · 2024: 13 · 2023: 13 · 2022: 11 · 2021: 16 · 2020: 18 · 2019: 14 · 2018: 9 · 2017: 11 · 2016: 19 · 2015: 12 · 2014: 17 · 2013: 12 · 2012: 14
FWCI: 3.77
Type: journal article
Language: en
Open access: bronze
doi.org
Licence: www.nrcresearchpress.com/page/about/CorporateTextAndDataMining (tdm)
Locations: Canadian Journal of Chemistry (publishedVersion)
Topics: Physical Sciences › Environmental Science › Environmental Chemistry › Aquatic Ecosystems and Phytoplankton Dynamics
Life Sciences › Immunology and Microbiology › Applied Microbiology and Biotechnology › Microbial Natural Products and Biosynthesis
Physical Sciences › Environmental Science › Environmental Chemistry › Marine Toxins and Detection Methods
Keywords: anatoxin-a, toxic alkaloids, Anabaena flos-aquae, cyanobacteria, structure elucidation, natural product isolation, mass culture

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Anatoxin-a, a toxic alkaloid from Anabaena flos-aquae NRC-44h

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