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Chemical Compound Review

Obtusifoliol     (3S,4S,5S,10S,13R,14R,17R)- 4,10,13,14...

Synonyms: CHEMBL481434, SureCN2511101, LMST01030101, AC1L22WJ, C01943, ...
 
 
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Disease relevance of C01943

 

High impact information on C01943

  • CYP51 removes the 14alpha-methyl group from sterol precursors such as lanosterol, obtusifoliol, dihydrolanosterol, and 24(28)-methylene-24,25-dihydrolanosterol [3].
  • The heme-thiolate (cytochrome P450) enzyme which catalyzes the 14alpha-demethylation of obtusifoliol has been isolated from microsomes prepared from etiolated seedlings of Sorghum bicolor (L.) Moench [4].
  • Therefore it is conceivable that the obtusifoliol 14alpha-demethylase from plants also belongs to the CYP51 family, the only P450 family so far known to be conserved across the phyla [4].
  • Plant CYP51 encodes an obtusifoliol 14alpha-demethylase involved in the postsqualene sterol biosynthetic pathway [5].
  • Furthermore, treatments of leaves with (14)C-labeled obtusifoliol demonstrated that this sterol could be transported in distal parts of the plant away from the sprayed leaves [6].
 

Chemical compound and disease context of C01943

 

Biological context of C01943

 

Anatomical context of C01943

  • Obtusifoliol 14alpha-demethylase has an apparent molecular mass of 53 kDa and is estimated to constitute approximately 20% of the total cytochrome P450 content of the microsomal membranes and about 0.2% of the total microsomal protein [4].
 

Associations of C01943 with other chemical compounds

  • Measurements of endogenous sterol levels in the cyp51A2 mutant revealed that it accumulates obtusifoliol, the substrate of CYP51, and a high proportion of 14alpha-methyl-delta8-sterols, at the expense of campesterol and sitosterol [5].
 

Gene context of C01943

  • Cloning and functional expression in yeast of a cDNA coding for an obtusifoliol 14alpha-demethylase (CYP51) in wheat [11].
  • CYP51 from Trypanosoma brucei is obtusifoliol-specific [12].
  • It is concluded that in Zea mays microsomes, the C-4 demethylation of 1 results from a multistep process involving a terminal oxygenation system sensitive to cyanide which is distinct from cytochrome P-450 and in particular from that involved in the 14 alpha-demethylation of obtusifoliol [13].

References

  1. Functional cloning of an Arabidopsis thaliana cDNA encoding cycloeucalenol cycloisomerase. Lovato, M.A., Hart, E.A., Segura, M.J., Giner, J.L., Matsuda, S.P. J. Biol. Chem. (2000) [Pubmed]
  2. Sterol composition of Cryptococcus neoformans in the presence and absence of fluconazole. Ghannoum, M.A., Spellberg, B.J., Ibrahim, A.S., Ritchie, J.A., Currie, B., Spitzer, E.D., Edwards, J.E., Casadevall, A. Antimicrob. Agents Chemother. (1994) [Pubmed]
  3. Crystal structure of cytochrome P450 14alpha -sterol demethylase (CYP51) from Mycobacterium tuberculosis in complex with azole inhibitors. Podust, L.M., Poulos, T.L., Waterman, M.R. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  4. Isolation and reconstitution of the heme-thiolate protein obtusifoliol 14alpha-demethylase from Sorghum bicolor (L.) Moench. Kahn, R.A., Bak, S., Olsen, C.E., Svendsen, I., Moller, B.L. J. Biol. Chem. (1996) [Pubmed]
  5. Arabidopsis cyp51 mutant shows postembryonic seedling lethality associated with lack of membrane integrity. Kim, H.B., Schaller, H., Goh, C.H., Kwon, M., Choe, S., An, C.S., Durst, F., Feldmann, K.A., Feyereisen, R. Plant Physiol. (2005) [Pubmed]
  6. Lipid signaling in plants. Cloning and expression analysis of the obtusifoliol 14alpha-demethylase from Solanum chacoense Bitt., a pollination- and fertilization-induced gene with both obtusifoliol and lanosterol demethylase activity. O'Brien, M., Chantha, S.C., Rahier, A., Matton, D.P. Plant Physiol. (2005) [Pubmed]
  7. Cloning and expression in Escherichia coli of the obtusifoliol 14 alpha-demethylase of Sorghum bicolor (L.) Moench, a cytochrome P450 orthologous to the sterol 14 alpha-demethylases (CYP51) from fungi and mammals. Bak, S., Kahn, R.A., Olsen, C.E., Halkier, B.A. Plant J. (1997) [Pubmed]
  8. 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]
  9. Accumulation of 3-ketosteroids induced by itraconazole in azole-resistant clinical Candida albicans isolates. Marichal, P., Gorrens, J., Laurijssens, L., Vermuyten, K., Van Hove, C., Le Jeune, L., Verhasselt, P., Sanglard, D., Borgers, M., Ramaekers, F.C., Odds, F., Vanden Bossche, H. Antimicrob. Agents Chemother. (1999) [Pubmed]
  10. Virus-induced silencing of sterol biosynthetic genes: identification of a Nicotiana tabacum L. obtusifoliol-14alpha-demethylase (CYP51) by genetic manipulation of the sterol biosynthetic pathway in Nicotiana benthamiana L. Burger, C., Rondet, S., Benveniste, P., Schaller, H. J. Exp. Bot. (2003) [Pubmed]
  11. Cloning and functional expression in yeast of a cDNA coding for an obtusifoliol 14alpha-demethylase (CYP51) in wheat. Cabello-Hurtado, F., Zimmerlin, A., Rahier, A., Taton, M., DeRose, R., Nedelkina, S., Batard, Y., Durst, F., Pallett, K.E., Werck-Reichhart, D. Biochem. Biophys. Res. Commun. (1997) [Pubmed]
  12. CYP51 from Trypanosoma brucei is obtusifoliol-specific. Lepesheva, G.I., Nes, W.D., Zhou, W., Hill, G.C., Waterman, M.R. Biochemistry (2004) [Pubmed]
  13. Oxidative C4-demethylation of 24-methylene cycloartanol by a cyanide-sensitive enzymatic system from higher plant microsomes. Pascal, S., Taton, M., Rahier, A. Biochem. Biophys. Res. Commun. (1990) [Pubmed]
 
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