Comparative study of toxic and non-toxic cyanobacterial products: Novel peptides from toxic Nodularia spumigena AV1

Fujii, Kiyonaga; Sivonen, Kaarina; Adachi, Kyoko; Noguchi, Kazuyoshi; Sano, Hiroshi; Hirayama, Kazuo; Suzuki, Makoto; Harada, Kenichi

doi:10.1016/s0040-4039(97)01192-1

Cited by 95 publications

(117 citation statements)

References 13 publications

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“…strain ATCC 53789 (1). Interestingly, in an aeruginosin-like peptide from Nodularia spumigena, spumigin (12), an intact C-terminal arginine moiety has been identified.…”

Section: Resultsmentioning

confidence: 99%

Plasticity and Evolution of Aeruginosin Biosynthesis in Cyanobacteria

Ishida

Welker

Christiansen

et al. 2009

Appl Environ Microbiol

100

110

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“…strain ATCC 53789 (1). Interestingly, in an aeruginosin-like peptide from Nodularia spumigena, spumigin (12), an intact C-terminal arginine moiety has been identified.…”

Section: Resultsmentioning

confidence: 99%

Plasticity and Evolution of Aeruginosin Biosynthesis in Cyanobacteria

Ishida

Welker

Christiansen

et al. 2009

Appl Environ Microbiol

100

110

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“…Spumigins are linear peptides with arginine and related amino acids. 22) Ocsillacyclin is a typical cyclic peptide containing 9 amino acid residues. As mentioned earlier, nostophycin was a 22-membered cyclic peptide isolated from Nostoc sp.…”

Section: Structural Classification Of Isolated Compoundsmentioning

confidence: 99%

Production of Secondary Metabolites by Freshwater Cyanobacteria

Harada

2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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Freshwater cyanobacteria produce lethal toxins such as microcystins and anatoxins. During the purification of microcystins in bloom samples we found that a toxic cyanobacterium produced not only microcystins but also other types-peptides in early 1990. Since then we have isolated approximately thirty peptides from freshwater cyanobacteria. In this manuscript we focused on the following topics concerning the isolated peptides: 1) how to isolate desired compounds and to determine their structures, 2) structural classification of isolated compounds, 3) isolation of similar peptides from laboratory strains and bloom materials, 4) structurally related peptides from freshwater and marine origins, 5) b b-amino acid containing peptides from cyanobacteria, 6) comprehensive analysis system for the biosynthetic study of peptides produced by cyanobacteria, 7) biological activities of isolated compounds.

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“…Reference Marfey derivatives of l-and d-amino acids were prepared similarly with amino acid solutions (50 mL, 50 mm). Reference compound (2S,4S)-4-MePro was obtained by hydrolysing spumigins A, B1, B2 and C purified from Nodularia spumigena AV1 [30] at 112 8C for 24 h.…”

Section: Derivatisation Of Nostocyclopeptide M1mentioning

confidence: 99%

A Novel Cyanobacterial Nostocyclopeptide is a Potent Antitoxin against Microcystins

et al. 2010

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Cyanobacterial hepatotoxins (microcystins and nodularins) cause numerous animal poisonings worldwide each year and are threats to human health. However, we found that extracts from several cyanobacteria isolates failed to induce hepatotoxicity even if they contained high concentrations of the liver toxin microcystin. The antitoxic activity abolishes all morphological hallmarks of microcystin-induced apoptosis, and therefore invalidates cell-based assays of the microcystin content of bloom-forming cyanobacteria. The antitoxin was purified from a cyanobacterial isolate (Nostoc sp. XSPORK 13A) from the Baltic Sea, and the activity was shown to reside in a novel cyclic peptide of the nostocyclopeptide family (nostocyclopeptide M1, Ncp-M1) that consists of seven amino acids (Tyr1-Tyr2-D-HSe3-L-Pro4-L-Val5-(2S,4S)-4-MPr6-Tyr7; MW=881) with an imino linkage between Tyr1 and Tyr7. Ncp-M1 did not compete with labelled microcystin for binding to protein phosphatase 2A; this explains why the antitoxin did not interfere with phosphatase-based microcystin assays. Currently used agents that interfere with microcystin action, such as inhibitors of ROS formation, microcystin uptake and Cam-kinase activity, are themselves inherently toxic. Since Ncp-M1 is potent and nontoxic it promises to become a useful mechanistic tool as soon as its exact cellular target is elucidated.

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Comparative study of toxic and non-toxic cyanobacterial products: Novel peptides from toxic Nodularia spumigena AV1

Cited by 95 publications

References 13 publications

Plasticity and Evolution of Aeruginosin Biosynthesis in Cyanobacteria

Plasticity and Evolution of Aeruginosin Biosynthesis in Cyanobacteria

Production of Secondary Metabolites by Freshwater Cyanobacteria

A Novel Cyanobacterial Nostocyclopeptide is a Potent Antitoxin against Microcystins

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