Microcystins from Anabaena flos-aquae NRC 525-17

Harada, Kenichi; Ogawa, Kiyoshi; Kimura, Yukio; Murata, Hideaki; Suzuki, Makoto; Thorn, Patti M.; Evans, William; Carmichael, Wayne W.

doi:10.1021/tx00023a008

Cited by 118 publications

(56 citation statements)

References 34 publications

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“…We identified variant B as MCYST-HtyR ( Fig. 2 and 3), which has been documented from Anabaena flos-aquae NRC 525-17 (12) and is the only variant having an m/z value of 1,059. Variants C and D were classified as [D-Asp 3 ]MCYST-LR and MCYST-LR, respectively ( Fig.…”

Section: Extraction Of Microcystins Frommentioning

confidence: 82%

Direct Evidence for Production of Microcystins by Anabaena Strains from the Baltic Sea

Halinen

Jokela

Fewer

et al. 2007

Appl Environ Microbiol

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Section: Extraction Of Microcystins Frommentioning

confidence: 82%

Direct Evidence for Production of Microcystins by Anabaena Strains from the Baltic Sea

Halinen

Jokela

Fewer

et al. 2007

Appl Environ Microbiol

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“…5a. 14) In the next step we have to differentiate microcystins from other type-compounds. For this purpose LC/MS is quite effective, because any microcystin gives a common characteristic fragment ion, m/z 135, which is derived from the Adda ((2S,3S,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4(E),6(E)-dienoic acid) portion and this is available for the differentiation of microcystins from other typecompounds.…”

Section: How To Isolate Desired Compounds and To Determine Their Strumentioning

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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“…Strains of the genus Anabaena produce a broad range of N-methylated microcystins Halinen et al, 2007;Harada et al, 1991;Krishnamurthy et al, 1989;Sivonen et al, 1992a, b). It has been shown in several studies that strains of the genus Anabaena produce mixtures of microcystins, some of which lack the N-methyl group (Halinen et al, 2007;Namikoshi et al, 1992aNamikoshi et al, , b, 1998Sivonen et al, 1992a, b).…”

Section: Introductionmentioning

confidence: 99%

Natural occurrence of microcystin synthetase deletion mutants capable of producing microcystins in strains of the genus Anabaena (Cyanobacteria)

et al. 2008

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Microcystins form a large family of small cyclic heptapeptides harbouring extensive modifications in amino acid residue composition and functional group chemistry. These peptide hepatotoxins contain a range of non-proteinogenic amino acids and unusual peptide bonds, and are typically N-methylated. They are synthesized on large enzyme complexes consisting of non-ribosomal peptide synthetases and polyketide synthases in a variety of distantly related cyanobacterial genera. Here we report a 1236 bp in-frame deletion mutation in the mcyA gene of the microcystin biosynthetic pathway in nine strains of the genus Anabaena. The deletion removed almost the entire N-methyltransferase (NMT) domain. Strains of Anabaena carrying the in-frame deletion mutation incorporated mainly dehydroalanine (Dha) into the microcystins they produce while strains with full-length mcyA genes incorporated mainly N-methyldehydroalanine (Mdha). Interestingly, the strains of Anabaena lacking the NMT domain also incorporated elevated amounts of L-Ser, the precursor of Mdha and Dha, into the microcystin they produced relative to strains carrying functional NMT domains. We provide evidence for the in-frame deletion of the NMT domain without the co-conversion of the flanking adenylation domain. Our results demonstrate a further example of the strategies employed by cyanobacteria in the biosynthesis of microcystin variants.

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Microcystins from Anabaena flos-aquae NRC 525-17

Cited by 118 publications

References 34 publications

Direct Evidence for Production of Microcystins by Anabaena Strains from the Baltic Sea

Direct Evidence for Production of Microcystins by Anabaena Strains from the Baltic Sea

Production of Secondary Metabolites by Freshwater Cyanobacteria

Natural occurrence of microcystin synthetase deletion mutants capable of producing microcystins in strains of the genus Anabaena (Cyanobacteria)

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