A low-toxicity method for the separation of lanosterol and dihydrolanosterol from commercial mixtures

Steroids

Volumn 69, Issue 10, 2004, Pages 697-700

  Kavtaradze, Levan K ^a   Manley Harris, Merilyn ^a   Nicholson, Brian K ^a  

^a UNIVERSITY OF WAIKATO   (New Zealand)

Author keywords

Dihydrolanosterol; Dihydroxylation; Hydroxyhalogenation; Hypophosphorous acid; Lanosterol

Indexed keywords

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; DIHYDROLANOSTEROL; DIHYDROLANOSTEROL ACETATE; IMIDE; LANOSTEROL; PHOSPHORUS ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOAVAILABILITY; CATALYSIS; CATALYST; CHEMICAL BOND; CONTROLLED STUDY; EPOXIDATION; HALOGENATION; HUMAN; RACEMIC MIXTURE; TOXICITY;

ACETYLATION; EPOXY COMPOUNDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HALOGENS; LANOSTEROL; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 4644330530     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2004.07.003     Document Type: Article

References (13)

1. W.D. Nes Sterol methyl transferase: enzymology and inhibition Biochim Biophys Acta 1529 2000 63 88
2. V.R. Chinthalapally, H.L. Newmark, and S.R. Bandaru Chemopreventative effects of farnesol and lanosterol on colon carcinogenesis Cancer Detect Prev 26 2002 419 425
3. M. Maienthal, and P.J. Franklin Preparation of lanosterol from bromolanosterol J Org Chem 20 1955 1627 1630
4. D.A. Lewis, and J.F. McGhie Isolation and reaction of lanosta-8,24-dien-3β-ol Chem Ind (Lond) 1956 550 551
5. J.D. Johnston, F. Gautschi, and K. Bloch Isolation of lanosterol from "isocholesterol" J Biol Chem 224 1957 185 190
6. R.B. Boar, D.A. Lewis, and J.F. McGhie Isolation and some reactions of lanosterol. A synthesis of agnosterol J Chem Soc Perkin Trans I 15 1973 1583 1588
7. W.J. Rodewald, and J.J. Jagodzinski A new method of isolating lanosterol from "isocholesterol" Pol J Chem 52 1978 2473 2477
8. Kavtaradze LK, Manley-Harris M, Nicholson BK. Efficient routes to epimerically-pure side-chain derivatives of lanosterol. Steroids 2004;69:227-33.
9. Y. Honda, T. Honda, S. Roy, and G.W. Gribble Revision and confirmation of the regiochemistry of isoxazoles derived from methyl oleanonate and lanost-8-en-3-one. Synthesis of a new lanostane triterpenoid with a cyano-enone functionality in ring A J Org Chem 68 2003 4991 4993
10. K.H. Raab, N.J. De Souza, and W.R. Nes The H-migration in the alkylation of sterols at C-24 Biochim Biophys Acta 1968 742 748
11. Y. Sato, and Y.S. Sonada Synthesis of lanosterol analogs with modified side chains Chem Pharm Bull 29 1981 356 365
12. G.T. Emmons, W.K. Wilson, and G.J. Schroepfer Proton and carbon-13 NMR assignment for lanostan-3β-ol derivatives: revised assignments for lanosterol Magn Res Chem 27 1989 1012 1024
13. F.W. Eastwood, K.J. Harrington, J.S. Josan, and J.L. Pura The conversion of 2-dimethylamino-1, 3-dioxolanes into alkenes Tetrahedron Lett 60 1970 5223 5224