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Chemical Compound Review

Flaviolin     4,5,7-trihydroxynaphthalene- 1,2-dione

Synonyms: SureCN703160, AG-J-10675, SureCN2315695, CHEBI:42646, AC1L4NOY, ...
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Disease relevance of Flaviolin

  • Binding of two flaviolin substrate molecules, oxidative coupling, and crystal structure of Streptomyces coelicolor A3(2) cytochrome P450 158A2 [1].
  • The soluble, diffusible red-brown pigment produced by a Saccharopolyspora erythraea "red variant" has been shown to contain glycosylated and polymerized derivatives of 2,5,7-trihydroxy-1,4-naphthoquinone (flaviolin) [2].

High impact information on Flaviolin

  • Particularly interesting is the presence of two molecules of flaviolin in the closed active site [1].
  • Following cloning, expression, and purification of this cytochrome P450, we have shown that it can produce dimer and trimer products from the substrate flaviolin and that the structures of two of the dimeric products were established using mass spectrometry and multiple NMR methods [1].
  • CYP158A2 has been suggested to produce polymers of flaviolin, a pigment that may protect microbes from UV radiation, in combination with the adjacent rppA gene, which encodes the type III polyketide synthase, 1,3,6,8-tetrahydroxynaphthalene synthase [1].
  • Our analyses also suggest that Ser214 and Tyr288, forming hydrogen bonds with the alternative binding states of 1,6-dihydroxynaphthalene and flaviolin, are good candidates for site-directed mutagenesis, and changing them to, for example, their hydrophobic counterparts would affect the substrate selectivity and product regioselectivity [3].
  • Scytalone and flaviolin obtained from cultures of the reddish brown mutant were identified by thin-layer chromatography, high-performance liquid chromatography, and UV spectra [4].

Chemical compound and disease context of Flaviolin


Associations of Flaviolin with other chemical compounds


  1. Binding of two flaviolin substrate molecules, oxidative coupling, and crystal structure of Streptomyces coelicolor A3(2) cytochrome P450 158A2. Zhao, B., Guengerich, F.P., Bellamine, A., Lamb, D.C., Izumikawa, M., Lei, L., Podust, L.M., Sundaramoorthy, M., Kalaitzis, J.A., Reddy, L.M., Kelly, S.L., Moore, B.S., Stec, D., Voehler, M., Falck, J.R., Shimada, T., Waterman, M.R. J. Biol. Chem. (2005) [Pubmed]
  2. Identification and cloning of a type III polyketide synthase required for diffusible pigment biosynthesis in Saccharopolyspora erythraea. Cortés, J., Velasco, J., Foster, G., Blackaby, A.P., Rudd, B.A., Wilkinson, B. Mol. Microbiol. (2002) [Pubmed]
  3. Understanding the substrate selectivity and the product regioselectivity of orf2-catalyzed aromatic prenylations. Cui, G., Li, X., Merz, K.M. Biochemistry (2007) [Pubmed]
  4. Biosynthesis and functions of melanin in Sporothrix schenckii. Romero-Martinez, R., Wheeler, M., Guerrero-Plata, A., Rico, G., Torres-Guerrero, H. Infect. Immun. (2000) [Pubmed]
  5. Biosynthesis of flaviolin and 5,8-dihydroxy-2,7-dimethoxy-1,4-naphthoquinone. McGovern, E.P., Bentley, R. Biochemistry (1975) [Pubmed]
  6. Melanin biosynthesis and the metabolism of flaviolin and 2-hydroxyjuglone in Wangiella dermatitidis. Wheeler, M.H., Stipanovic, R.D. Arch. Microbiol. (1985) [Pubmed]
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