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The structure of cyanoginosin-LA, a cyclic heptapeptide toxin from the cyanobacterium Microcystis aeruginosa
Abstract
The structure of cyanoginosin-LA (previously referred to by us as toxin BE-4) is cyclo(-D-Ala-L-Leu-erythro-β-methyl-D-isoAsp-L-Ala-Adda-D-Glu-N-methyldehydroAla)(17a), where Adda refers to the novel β-amino acid residue of 3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid (11). The connectivity of Adda is deduced from 1H- and 13C-n.m.r. data, but the stereochemistry at carbons 2,3,8, and 9 remains unknown. The residue sequence is derived from the mass spectra of cyclic and linear derivatives of the toxin. A new nomenclature for the related toxins of Microcystis aeruginosa is discussed.
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Citations
Cited by
Inhibition of protein phosphatases by microcystis and nodularin associated with hepatotoxicity
Yoshizawa, S., Matsushima, R., Watanabe, M. F., Harada, K.-I., Ichihara, A., Carmichael, W. W., & Fujiki, H. (1990) · Journal of Cancer Research and Clinical Oncology · doi:10.1007/bf01637082 · Cited by 578
Cyanobacterial toxins: removal during drinking water treatment, and human risk assessment.
Hitzfeld, B. C., Höger, S. J., & Dietrich, D. R. (2000) · Environmental Health Perspectives · doi:10.1289/ehp.00108s1113 · Cited by 438
Hepatocyte deformation induced by cyanobacterial toxins reflects inhibition of protein phosphatases
Eriksson, J. E., Toivola, D., Meriluoto, J. A. O., Karaki, H., Han, Y.-G., & Hartshorne, D. (1990) · Biochemical and Biophysical Research Communications · doi:10.1016/s0006-291x(05)80936-2 · Cited by 340
Cyclic peptides and depsipeptides from cyanobacteria: A review
Moore, R. E. (1996) · Journal of Industrial Microbiology · doi:10.1007/bf01570074 · Cited by 277
Metadata
- Authors
- Botes, D. P., Tuinman, A. A., Wessels, P. L., Viljoen, C. C., Kruger, H., Williams, D. H., Santikarn, S., Smith, R. J., & Hammond, S. J.
- Venue
- Journal of the Chemical Society, Perkin Transactions 1
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 1984
- Pages
- 2311
- ISSN
- 1364-5463 (ISSN-L)
- 0300-922X
- OpenAlex
- W2017387930
- Cited by
- 332
- References
- 0
- FWCI
- 4.78
- Type
- journal article
- Language
- en
- Open access
- closed
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- Botes, D. P., Tuinman, A. A., Wessels, P. L., Viljoen, C. C., Kruger, H., Williams, D. H., Santikarn, S., Smith, R. J., & Hammond, S. J. (1984). The structure of cyanoginosin-LA, a cyclic heptapeptide toxin from the cyanobacterium Microcystis aeruginosa. Journal of the Chemical Society, Perkin Transactions 1. https://doi.org/10.1039/p19840002311
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