라노스테롤

라노스테롤 화학적 특성, 용도, 생산

• 개요

  Lanosterol is a naturally-occurring sterol and biosynthetic precursor of several animal, fungal, and protozoan steroids, including cholesterol and ergosterol. Defects in the processing of lanosterol contribute to a wide variety of disorders, including the formation of cataracts. Similarly, certain fungicides act by blocking lanosterol processing by fungi.

• 용도

  Lanosterol has been used:
  
  • as a standard in HPLC for the quantification in testis samples
  • in S-adenosyl-L-methionine:Δ²⁴-sterol-C-methyltransferase (SMT) assay
  • to treat wild-type cells growing in rich medium to know its effects on Sre1 protein
  
  

• 정의

  ChEBI: A tetracyclic triterpenoid that is lanosta-8,24-diene substituted by a beta-hydroxy group at the 3beta position. It is the compound from which all steroids are derived.

• 일반 설명

  Lanosterol, an amphipathic molecule, that is produced by?lanosterol?synthase (LSS). It is enriched in the lens.

• Purification Methods

  If very impure, then it should be acetylated, converted to the dibromide acetate [crystallised from EtOAc with slow cooling, m 168-170o, [] D +214o (CHCl3)], de-brominated with Zn dust to give the acetate (below) which is recrystallised from 3-4 parts of Me2CO/MeOH (4:1) and hydrolysed as for stigmasterol (below). Recrystallise it from anhydrous MeOH. Dry it in vacuo over P2O5 for 3hours at 90o. The purity is checked by proton magnetic resonance. The acetate crystallises from MeOH with m 131-133o and [ ] 25D +62o (c 1,CHCl3). [Block & Urech Biochemical Preparations 6 32 1958. van Tamelen et al. J Am Chem Soc 104 6479, 6480 1982, Beilstein 6 III 2880, 6 IV 4188.]

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