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Chemical Compound Review:

Toxoflavin 4,10-dimethyl-2,4,7,9,10...

Synonyms: Toxoflavine, Xanthotricin, Xanthothricin, Xanthrothricin, GNF-Pf-67, ...

Kim, J. et al., Zhao, N. et al., Nagamatsu, T. et al., Wang, Z. et al., Lin, L.M. et al., et al.

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Disease relevance of U-7118

Quorum sensing and the LysR-type transcriptional activator ToxR regulate toxoflavin biosynthesis and transport in Burkholderia glumae [1].
1. It has been suggested that the toxic effect of toxoflavin (TXF) produced by Pseudomonas cocovenenas is mainly due to the impairment of electron transfer of the mitochondrial respiratory chain [2].

High impact information on U-7118

Non-motile qsmR, fliA and flhDC mutants produced toxoflavin, but lost pathogenicity for rice [3].
Using Tn3-gusA reporter fusions, we found that ToxR, a LysR-type regulator, regulates both the toxABCDE and toxFGHI operons in the presence of toxoflavin as a coinducer [1].
Our molecular and genetic analyses of toxoflavin-deficient mutants demonstrated that gene clusters for toxoflavin production consist of four transcriptional units [1].
Pseudomonas cocovenenans, the producer of bongkrekic acid and toxoflavin, has been described previously by us (N.-X. Zhao, M.-S. Ma, Y.-P. Zhang, and D.-C. Xu, Int. J. Syst. Bacteriol. 40:452-455, 1990) in terms of more than 180 phenotypic traits, G+C content, and DNA relatedness [4].
The application of the method to the simultaneous determination of bongkrekic acid and toxoflavin, the toxic metabolites produced by Pseudomonas farinofermentans, is described [5].

Biological context of U-7118

6-Phenyl analogs of toxoflavin (1-methyl-6-phenylpyrimido[5,4-e]-1,2,4-triazine-5,7(1H,6H)-diones ) (7a--f) and their 4-oxides (8a-f) were synthesized by nitrosative or nitrative cyclization of the aldehyde hydrazones (6a-f) of 6-(1-methylhydrazino)-3-phenyluracil (5) [6].

References

Quorum sensing and the LysR-type transcriptional activator ToxR regulate toxoflavin biosynthesis and transport in Burkholderia glumae. Kim, J., Kim, J.G., Kang, Y., Jang, J.Y., Jog, G.J., Lim, J.Y., Kim, S., Suga, H., Nagamatsu, T., Hwang, I. Mol. Microbiol. (2004) [Pubmed]
Enhanced vasocontraction of rat tail arteries by toxoflavin. Wang, Z., Ma, M., Wang, R. Br. J. Pharmacol. (1996) [Pubmed]
Regulation of polar flagellum genes is mediated by quorum sensing and FlhDC in Burkholderia glumae. Kim, J., Kang, Y., Choi, O., Jeong, Y., Jeong, J.E., Lim, J.Y., Kim, M., Moon, J.S., Suga, H., Hwang, I. Mol. Microbiol. (2007) [Pubmed]
Phylogenetic evidence for the transfer of Pseudomonas cocovenenans (van Damme et al. 1960) to the genus Burkholderia as Burkholderia cocovenenans (van Damme et al. 1960) comb. nov. Zhao, N., Qu, C., Wang, E., Chen, W. Int. J. Syst. Bacteriol. (1995) [Pubmed]
Simultaneous determination of toxic metabolites by linear combination derivative spectrophotometry. Lin, L.M., Zhao, N.X. The Analyst. (1991) [Pubmed]
Syntheses of 3-substituted 1-methyl-6-phenylpyrimido[5,4-e]-1,2,4-triazine-5,7(1H,6H)-diones (6-phenyl analogs of toxoflavin) and their 4-oxides, and evaluation of antimicrobial activity of toxoflavins and their analogs. Nagamatsu, T., Yamasaki, H., Hirota, T., Yamato, M., Kido, Y., Shibata, M., Yoneda, F. Chem. Pharm. Bull. (1993) [Pubmed]

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