Deoxycylindrospermopsin, an analog of cylindrospermopsin from Cylindrospermopsis raciborskii

Norris, Ross; Eaglesham, G.; Pierens, Greg; Shaw, G. R.; Smith, Maree J.; Chiswell, Robyn K.; Seawright, A. A.; Moore, Michael R.

doi:10.1002/(sici)1522-7278(199902)14:1<163::aid-tox21>3.3.co;2-m

Cited by 46 publications

(76 citation statements)

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“…A Fugue search and an iterated Psi-BLAST revealed that CyrI is similar to a hydroxylase belonging to the 2-oxoglutarate-and Fe(II)-dependent oxygenase superfamily, which includes the mammalian prolyl 4-hydroxylase alpha subunit, which catalyzes the hydroxylation of collagen. We propose that CyrI catalyzes the hydroxylation of C-7, a residue that along with the uracil ring seems to confer much of the toxicity of cylindrospermopsin (28). This is supported by the feeding experiments showing that the hydroxyl group at C-7 of cylindrospermopsin is not of acetate origin.…”

Section: The Mt Domain Identified In Cyrb Via the Nrps/pks Databases mentioning

confidence: 99%

Characterization of the Gene Cluster Responsible for Cylindrospermopsin Biosynthesis

Mihali

Kellmann

Muenchhoff

et al. 2008

Appl Environ Microbiol

264

263

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Toxic cyanobacterial blooms cause economic losses and pose significant public health threats on a global scale. Characterization of the gene cluster for the biosynthesis of the cyanobacterial toxin cylindrospermopsin (cyr) in Cylindrospermopsis raciborskii AWT205 is described, and the complete biosynthetic pathway is proposed. The cyr gene cluster spans 43 kb and is comprised of 15 open reading frames containing genes required for the biosynthesis, regulation, and export of the toxin. Biosynthesis is initiated via an amidinotransfer onto glycine followed by five polyketide extensions and subsequent reductions, and rings are formed via Michael additions in a stepwise manner. The uracil ring is formed by a novel pyrimidine biosynthesis mechanism and tailoring reactions, including sulfation and hydroxylation that complete biosynthesis. These findings enable the design of toxic strain-specific probes and allow the future study of the regulation and biological role of cylindrospermopsin.

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Section: The Mt Domain Identified In Cyrb Via the Nrps/pks Databases mentioning

confidence: 99%

Characterization of the Gene Cluster Responsible for Cylindrospermopsin Biosynthesis

Mihali

Kellmann

Muenchhoff

et al. 2008

Appl Environ Microbiol

264

263

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“…[106]. CYN has two known derivatives, one of them is toxic, 7-epicylindrospermopsin [1] and the other virtually nontoxic, deoxy-cylindrospermosin [86].…”

Section: Cylindrospermopsinsmentioning

confidence: 99%

Health hazards for terrestrial vertebrates from toxic cyanobacteria in surface water ecosystems

Briand¹,

Jacquet²,

et al. 2003

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-Toxigenic cyanobacteria are photosynthetic prokaryotes that are most often recognized in marine and freshwater systems, such as lakes, ponds, rivers, and estuaries. When environmental conditions (such as light, nutrients, water column stability, etc.) are suitable for their growth, cyanobacteria may proliferate and form toxic blooms in the upper, sunlit layers. The biology and ecology of cyanobacteria have been extensively studied throughout the world during the last two decades, but we still know little about the factors and processes involved in regulating toxin production for many cyanobacterial species. In this minireview, we discuss these microorganisms, and more especially the toxins they produce, as a potential and important health risk for wild and domestic animals.

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“…One of these analogues is 7-epi-CYN, a C-7 epimer of CYN with toxicity similar to CYN (2). The other is 7-deoxy-CYN, which lacks the hydroxyl group on C-7 and shows no toxicity to mice by intraperitoneal injection (35). In another study, however, 7-deoxy-CYN was proven to be a potent inhibitor of protein synthesis in vitro, and oxygenation at C7 was not essential for its toxicity (27).…”

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confidence: 99%

Molecular Basis and Phylogenetic Implications of Deoxycylindrospermopsin Biosynthesis in the Cyanobacterium Raphidiopsis curvata

Jiang

Xiao

et al. 2012

Appl Environ Microbiol

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ABSTRACTNew insights into the distribution and biochemistry of the cyanotoxin cylindrospermopsin (CYN) have been provided by the recent determination of its biosynthesis gene cluster (cyr) in several cyanobacterial species.Raphidiopsis curvataCHAB1150 isolated from China was analyzed for CYN analogues. Only 7-deoxy-CYN was detected in the cell extracts. Thecyrgene cluster ofR. curvataCHAB1150 was sequenced, and thecyrgenes of this strain were found to have extremely high similarities (96% to 100%) to those from other nostocalean species. These species includeCylindrospermopsis raciborskiiAWT205,Aphanizomenonsp. strain 10E6, andAphanizomenon ovalisporumILC-146. Insertion mutation was identified within thecyrIgene, and transcripts ofcyrIand another functional genecyrJwere detected inR. curvataCHAB1150. General congruence between the phylogenetic trees based on bothcyrand 16Srrnwas displayed. Neutral evolution was found on the whole sequences of thecyrgenes, and 0 to 89 negative selected codons were detected in each gene. Therefore, the function of CyrI is to catalyze the oxygenation of 7-deoxy-CYN in CYN biosynthesis. The transcripts of the mutatedcyrIgene may result from polycistronic transcription. The high conservation of thecyrgenes may be ascribed to purifying selection and horizontal gene transfer.

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Deoxycylindrospermopsin, an analog of cylindrospermopsin from Cylindrospermopsis raciborskii

Cited by 46 publications

References 0 publications

Characterization of the Gene Cluster Responsible for Cylindrospermopsin Biosynthesis

Characterization of the Gene Cluster Responsible for Cylindrospermopsin Biosynthesis

Health hazards for terrestrial vertebrates from toxic cyanobacteria in surface water ecosystems

Molecular Basis and Phylogenetic Implications of Deoxycylindrospermopsin Biosynthesis in the Cyanobacterium Raphidiopsis curvata

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