Deoxycylindrospermopsin, an analog of cylindrospermopsin fromCylindrospermopsis 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>3.0.co;2-v

Cited by 177 publications

(68 citation statements)

References 3 publications

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“…In contrast with microcystin and saxitoxin, for which numerous chemical variants have been described (e.g. Schantz, 1986;Welker & von Döhren, 2006), only two analogues of cylindrospermopsin are known: 7-epi-CYN and deoxy-CYN (Banker et al, 2000;Norris et al, 1999). The genetic basis of these CYN variants is not known, but it is likely that the dearth of analogues is related to the high sequence conservation.…”

Section: Discussionmentioning

confidence: 99%

The cylindrospermopsin gene cluster of Aphanizomenon sp. strain 10E6: organization and recombination

Stüken

Jakobsen

2010

Microbiology

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Cylindrospermopsin (CYN), a potent hepatoxin, occurs in freshwaters worldwide. Several cyanobacterial species produce the toxin, but the producing species vary between geographical regions. Aphanizomenon flos-aquae, a common algae species in temperate fresh and brackish waters, is one of the three well-documented CYN producers in European waters. So far, no genetic information on the CYN genes of this species has been available. Here, we describe the complete CYN gene cluster, including flanking regions from the German Aphanizomenon sp. strain 10E6 using a full genome sequencing approach by 454 pyrosequencing and bioinformatic identification of the gene cluster. In addition, we have sequenced a~7 kb fragment covering the genes cyrC (partially), cyrA and cyrB (partially) of the same gene cluster in the CYN-producing Aphanizomenon sp. strains 10E9 and 22D11. Comparisons with the orthologous gene clusters of the Australian Cylindrospermopsis raciborskii strains AWT205 and CS505 and the partial gene cluster of the Israeli Aphanizomenon ovalisporum strain ILC-146 revealed a high gene sequence similarity, but also extensive rearrangements of gene order. The high sequence similarity (generally higher than that of 16S rRNA gene fragments from the same strains), atypical GCcontent and signs of transposase activities support the suggestion that the CYN genes have been horizontally transferred.

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Section: Discussionmentioning

confidence: 99%

The cylindrospermopsin gene cluster of Aphanizomenon sp. strain 10E6: organization and recombination

Stüken

Jakobsen

2010

Microbiology

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“…Other members of the family include 7- epi -cylindrospermopsin ( 4 ), isolated from A. ovalisporum (3), and 7-deoxycylindrospermopsin ( 5 ), isolated from C. raciborskii (4). While 3 and 4 were shown to be equipotent hepatotoxic glutathione biosynthesis inhibitors, the deoxy analogue 5 showed no activity.…”

Section: Cylindrospermopsinmentioning

confidence: 99%

“…Acidic hydrolysis of the acetyl group and pyrimidines produced a separable mixture. Finally, treatment of 18 with sulfur trioxide-pyridine and molecular sieves in DMF gave a moderate yield of 7- epi -cylindrospermopsin (4) as a 2:1 mixture with the bissulfate (9). Cylindrospermopsin (3) was synthesized in a similar fashion (10).…”

Section: Cylindrospermopsinmentioning

confidence: 99%

ChemInform Abstract: New Tricks in Amino Acid Synthesis: Applications to Complex Natural Products

Williams

Burnett

2009

ChemInform

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“…A sensitive and selective procedure was proposed for the determination of glutathione and its oxidized form in liver tissues using HPLC in combination with tandem mass spectrometry [65] with detection limits of 0.2 pmol for glutathione and 2 pmol for the oxidized form.…”

Section: Determination Of Low-molecular Bioantioxidantsmentioning

confidence: 99%

Antioxidants As Analytes in Analytical Chemistry

Будников

Ziyatdinova

2005

J Anal Chem

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Procedures for the determination of individual antioxidants of different nature in biological materials with the use of electrochemical, chromatographic, spectrochemical, and other methods were considered. The main performance characteristics of these procedures are presented. JOURNAL OF ANALYTICAL CHEMISTRY Vol. 60 No. 7 2005 ANTIOXIDANTS AS ANALYTES IN ANALYTICAL CHEMISTRY 601rings, the ortho and para positions of hydroxyl groups, their tert -butyl screening, the formation of semiquinone forms, thiol-containing compounds, the chelation of variable-valence metals, receptor interactions with the cell membrane, etc.

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Deoxycylindrospermopsin, an analog of cylindrospermopsin fromCylindrospermopsis raciborskii

Cited by 177 publications

References 3 publications

The cylindrospermopsin gene cluster of Aphanizomenon sp. strain 10E6: organization and recombination

The cylindrospermopsin gene cluster of Aphanizomenon sp. strain 10E6: organization and recombination

ChemInform Abstract: New Tricks in Amino Acid Synthesis: Applications to Complex Natural Products

Antioxidants As Analytes in Analytical Chemistry

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