RESUMO
(22S,23S)-22,23-Epoxysitosterol, (22R,23R)-22,23-epoxysitosterol, (22S,23S)-22,23-epoxy-7-ketositosterol, (22R,23R)-22,23-epoxy-7-ketositosterol, (22S,23S)-22,23-epoxy-7alpha-hydroxysitosterol, (22R,23R)-22,23-epoxy-7alpha-hydroxysitosterol, (22S,23S)-22,23-epoxy-7beta-hydroxysitosterol, and (22R,23R)-22,23-epoxy-7beta-hydroxysitosterol were synthesized. Their 1H and 13C NMR and the mass spectra of their trimethylsilyl derivatives were studied.
Assuntos
Compostos de Epóxi/síntese química , Sitosteroides/síntese química , Compostos de Epóxi/química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Modelos Moleculares , Estrutura Molecular , Sitosteroides/químicaRESUMO
New analogues of 3beta-hydroxy-5alpha-cholest-8(14)-en-15-one (15-ketosterol) with modified 17-chains [(22S,23S,24S)- and (22R,23R,24S)-3beta-hydroxy-24-methyl-22,23-oxido-5alpha-cholest-8(14)-en-15-ones and (22RS,23xi,24S)-24-methyl-5alpha-cholesta-3beta,22,23-triol-15-one] were synthesized from (22E,24S)-3beta-acetoxy-24-methyl-5alpha-cholesta-8(14),22-dien-15-one. The chiralities of their 22 and 23 centers were determined by NMR spectroscopy. The isomeric 22,23-epoxides effectively inhibited cholesterol biosynthesis in hepatoma Hep G2 cells (IC50 0.9 +/- 0.2 and 0.7 +/- 0.2 microM, respectively), and their activities significantly exceeded those of 15-ketosterol (IC50 4.0 +/- 0.5 microM), (22E,24S)-3beta-hydroxy-24-methyl-5alpha-cholesta-8(14),22-dien-15-one (IC50 3.1 +/- 0.4 microM), and the 3beta,22,23-triol synthesized (IC50 6.0 +/- 1.0 microM). The English version of the paper: Russian Journal of Bioorganic Chemistry, 2005, vol. 31, no. 3; see also http://www.maik.ru.
Assuntos
Anticolesterolemiantes/síntese química , Anticolesterolemiantes/farmacologia , Cetocolesteróis/síntese química , Cetocolesteróis/farmacologia , Anticolesterolemiantes/química , Linhagem Celular Tumoral , Humanos , Cetocolesteróis/químicaRESUMO
The nucleotide sequence of a 208-bp fragment of the pfk gene encoding phosphofructokinase from Baikalian fish Cottocomephorus grewingki (Cottidae family) was determined. The fragment shows the codes of a sequence of 38 amino acid residues and contains a 94-bp intron. The nucleotide sequence of the C. grewingki phosphofructokinase gene and the corresponding amino acid sequence display the maximum homology to phosphofructokinases from rabbit muscles and a rat liver.
