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Chemical Compound Review

AC1NSV08     (3S,10S,13R,17R)- 4,4,10,13,14-pentamethyl...

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High impact information on Eburicol

  • Eburicol and obtusifolione are unable to support cell growth, and the 3-ketosteroid has been shown to disturb membranes [1].
  • The accumulation of obtusifolione as well as eburicol indicates that itraconazole inhibits not only the 14 alpha-demethylase but also (directly or indirectly) the NADPH-dependent 3-ketosteroid reductase, i.e., the enzyme catalyzing the last step in the demethylation at C-4 [1].
  • Interestingly the binding site, beyond the C-3 position, contains a cleft which cannot accommodate a 4 beta-methyl substituent present in lanosterol or eburicol, the precursors of 14-desmethylsterols respectively in mammals and yeast [2].
  • We used the nucleotide sequences of the gene that encodes eburicol 14alpha-demethylase (CYP51) and of the ribosomal DNA internal transcribed spacer 1 (ITS1), ITS2, and 5 [3].
  • Resistance to sterol 14alpha-demethylase inhibiting fungicides (DMIs) has been correlated with mutations in the CYP51 gene, which encodes the target enzyme eburicol 14alpha-demethylase [4].

Biological context of Eburicol


Anatomical context of Eburicol

  • No metabolism of lanosterol and eburicol, the substrates of the fungal and mammalian CYP51s, nor metabolism of herbicides and fatty acids was detected in the recombinant yeast microsomes [7].

Gene context of Eburicol

  • In this paper we describe the effects of over-expression of the Penicillium italicum gene encoding eburicol 14 alpha-demethylase (cyp51), in Aspergillus niger strains with one or multiple copies of the gene encoding cytochrome P450 reductase (cprA), on the eburicol 14 alpha-demethylase activity [8].

Analytical, diagnostic and therapeutic context of Eburicol

  • Cloning and sequence analysis of the eburicol 14alpha-demethylase gene of the obligate biotrophic grape powdery mildew fungus [9].
  • A cloning strategy based on PCR has therefore been used to clone the eburicol 14alpha-demethylase (CYP51) gene of the obligate fungus Erysiphe graminis f. sp. hordei (Egh) using minute amounts of genomic DNA [6].


  1. Effects of itraconazole on cytochrome P-450-dependent sterol 14 alpha-demethylation and reduction of 3-ketosteroids in Cryptococcus neoformans. Vanden Bossche, H., Marichal, P., Le Jeune, L., Coene, M.C., Gorrens, J., Cools, W. Antimicrob. Agents Chemother. (1993) [Pubmed]
  2. Properties and structural requirements for substrate specificity of cytochrome P-450-dependent obtusifoliol 14 alpha-demethylase from maize (Zea mays) seedlings. Taton, M., Rahier, A. Biochem. J. (1991) [Pubmed]
  3. Nested allele-specific PCR primers distinguish genetic groups of Uncinula necator. Délye, C., Ronchi, V., Laigret, F., Corio-Costet, M.F. Appl. Environ. Microbiol. (1999) [Pubmed]
  4. Sequence variation in the CYP51 gene of Blumeria graminis associated with resistance to sterol demethylase inhibiting fungicides. Wyand, R.A., Brown, J.K. Fungal Genet. Biol. (2005) [Pubmed]
  5. Isolation and molecular characterisation of the gene encoding eburicol 14 alpha-demethylase (cYP51) from Penicillium italicum. van Nistelrooy, J.G., van den Brink, J.M., van Kan, J.A., van Gorcom, R.F., de Waard, M.A. Mol. Gen. Genet. (1996) [Pubmed]
  6. PCR cloning and detection of point mutations in the eburicol 14alpha-demethylase (CYP51) gene from Erysiphe graminis f. sp. hordei, a "recalcitrant" fungus. Délye, C., Bousset, L., Corio-Costet, M.F. Curr. Genet. (1998) [Pubmed]
  7. Optimized expression and catalytic properties of a wheat obtusifoliol 14alpha-demethylase (CYP51) expressed in yeast. Complementation of erg11Delta yeast mutants by plant CYP51. Cabello-Hurtado, F., Taton, M., Forthoffer, N., Kahn, R., Bak, S., Rahier, A., Werck-Reichhart, D. Eur. J. Biochem. (1999) [Pubmed]
  8. Increased resistance to 14 alpha-demethylase inhibitors (DMIs) in Aspergillus niger by coexpression of the Penicillium italicum eburicol 14 alpha-demethylase (cyp51) and the A. niger cytochrome P450 reductase (cprA) genes. van den Brink, H.J., van Nistelrooy, H.J., de Waard, M.A., van den Hondel, C.A., van Gorcom, R.F. J. Biotechnol. (1996) [Pubmed]
  9. Cloning and sequence analysis of the eburicol 14alpha-demethylase gene of the obligate biotrophic grape powdery mildew fungus. Délye, C., Laigret, F., Corio-Costet, M.F. Gene (1997) [Pubmed]
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