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Volumn 48, Issue 2, 2013, Pages 197-207

Stereoselective synthesis and NMR characterization of C-24 Epimeric Pairs of 24-Alkyl oxysterols

Author keywords

(24R) (24S) Epimer; 24 Hydroxylation; 25 Hydroxylation; 13C NMR; 1H NMR; Alkylsterol; Aromatic solvent induced shift by C5D5N; Oxysterol

Indexed keywords

25 HYDROXY 24 METHYL 5 ALPHA CHOLESTAN 3 BETA YL ACETATE; HYDROXY 24 METHYL 5 ALPHA CHOLESTAN 3 BETA YL ACETATE; OXYSTEROL; UNCLASSIFIED DRUG;

EID: 84878368858     PISSN: 00244201     EISSN: 15589307     Source Type: Journal    
DOI: 10.1007/s11745-012-3739-1     Document Type: Article
Times cited : (2)

References (30)
  • 1
    • 0002429169 scopus 로고
    • Naturally occurring sterols and related compounds from plants
    • Patterson GW, Nes WD (eds) AOCS press, Champaign
    • Akihisa T, Kokke W (1991) Naturally occurring sterols and related compounds from plants In: Patterson GW, Nes WD (eds) Physiology and biochemistry of sterols. AOCS press, Champaign
    • (1991) Physiology and Biochemistry of Sterols
    • Akihisa, T.1    Kokke, W.2
  • 2
    • 77951914409 scopus 로고    scopus 로고
    • Effects of plant sterols and stanols beyond low-density lipoprotein cholesterol lowering
    • 20200328 10.1177/1074248409357921 1:CAS:528:DC%2BC3cXnsVOqtrY%3D
    • Derdemezis CS, Filippatos TD, Mikhailidis DP, Elisaf MS (2010) Effects of plant sterols and stanols beyond low-density lipoprotein cholesterol lowering. J Cardiovasc Pharmacol Ther 15:120-134
    • (2010) J Cardiovasc Pharmacol Ther , vol.15 , pp. 120-134
    • Derdemezis, C.S.1    Filippatos, T.D.2    Mikhailidis, D.P.3    Elisaf, M.S.4
  • 3
    • 0033594903 scopus 로고    scopus 로고
    • CDNA cloning of cholesterol 24-hydroxylase, a mediator of cholesterol homeostasis in the brain
    • 10377398 10.1073/pnas.96.13.7238 1:CAS:528:DyaK1MXltVOrtbg%3D
    • Lund EG, Guileyardo JM, Russell DW (1999) cDNA cloning of cholesterol 24-hydroxylase, a mediator of cholesterol homeostasis in the brain. Proc Natl Acad Sci USA 96:7238-7243
    • (1999) Proc Natl Acad Sci USA , vol.96 , pp. 7238-7243
    • Lund, E.G.1    Guileyardo, J.M.2    Russell, D.W.3
  • 4
    • 33646767428 scopus 로고    scopus 로고
    • Identification of a novel sulfonated oxysterol, 5-cholesten-3β,25- diol 3-sulfonate, in hepatocyte nuclei and mitochondria
    • 16505492 10.1194/jlr.M600019-JLR200 1:CAS:528:DC%2BD28XkvVCgsrg%3D
    • Ren S, Hylemon P, Zhang ZP, Rodriguez-Agudo D, Marques D, Li X, Zhou H, Gil G, Pandak WM (2006) Identification of a novel sulfonated oxysterol, 5-cholesten-3β,25-diol 3-sulfonate, in hepatocyte nuclei and mitochondria. J Lipid Res 47:1081-1090
    • (2006) J Lipid Res , vol.47 , pp. 1081-1090
    • Ren, S.1    Hylemon, P.2    Zhang, Z.P.3    Rodriguez-Agudo, D.4    Marques, D.5    Li, X.6    Zhou, H.7    Gil, G.8    Pandak, W.M.9
  • 5
    • 34447566893 scopus 로고    scopus 로고
    • Sulfated oxysterol, 25HC3S, is a potent regulator of lipid metabolism in human hepatocytes
    • 17624300 10.1016/j.bbrc.2007.06.143 1:CAS:528:DC%2BD2sXotVWmt7g%3D
    • Ren S, Li X, Rodriguez-Agudo D, Gil G, Hylemon P, Pandak WM (2007) Sulfated oxysterol, 25HC3S, is a potent regulator of lipid metabolism in human hepatocytes. Biochem Biophys Res Commun 360:802-808
    • (2007) Biochem Biophys Res Commun , vol.360 , pp. 802-808
    • Ren, S.1    Li, X.2    Rodriguez-Agudo, D.3    Gil, G.4    Hylemon, P.5    Pandak, W.M.6
  • 8
    • 0036736781 scopus 로고    scopus 로고
    • Do oxysterols control cholesterol homeostasis?
    • 12235099 1:CAS:528:DC%2BD38Xnt1ehtL4%3D
    • Bjorkhem I (2002) Do oxysterols control cholesterol homeostasis? J Clin Invest 110:725-730
    • (2002) J Clin Invest , vol.110 , pp. 725-730
    • Bjorkhem, I.1
  • 9
    • 80051469033 scopus 로고    scopus 로고
    • 24S-Hydroxycholesterol and cholesterol-24S-hydroxylase (CYP46A1) in the retina: From cholesterol homeostasis to pathophysiology of glaucoma
    • 21531213 10.1016/j.chemphyslip.2011.04.006 1:CAS:528:DC%2BC3MXpvFCntbc%3D
    • Fourgeux C, Bron A, Acar N, Creuzot-Garcher C, Bretillon L (2011) 24S-Hydroxycholesterol and cholesterol-24S-hydroxylase (CYP46A1) in the retina: from cholesterol homeostasis to pathophysiology of glaucoma. Chem Phys Lipids 164:496-499
    • (2011) Chem Phys Lipids , vol.164 , pp. 496-499
    • Fourgeux, C.1    Bron, A.2    Acar, N.3    Creuzot-Garcher, C.4    Bretillon, L.5
  • 10
    • 0025914556 scopus 로고
    • Mutations in the bile acid biosynthetic enzyme sterol 27-hydroxylase underlie cerebrotendinous xanthomatosis
    • 2019602 1:CAS:528:DyaK3MXksVOhtL8%3D
    • Cali JJ, Hsieh CL, Francke U, Russell DW (1991) Mutations in the bile acid biosynthetic enzyme sterol 27-hydroxylase underlie cerebrotendinous xanthomatosis. J Biol Chem 266:7779-7783
    • (1991) J Biol Chem , vol.266 , pp. 7779-7783
    • Cali, J.J.1    Hsieh, C.L.2    Francke, U.3    Russell, D.W.4
  • 11
    • 0034672672 scopus 로고    scopus 로고
    • Oxysterol biosynthetic enzymes
    • 11111082 10.1016/S1388-1981(00)00142-6 1:CAS:528:DC%2BD3cXosFCgsLw%3D
    • Russell DW (2000) Oxysterol biosynthetic enzymes. Biochim Biophys Acta 1529:126-135
    • (2000) Biochim Biophys Acta , vol.1529 , pp. 126-135
    • Russell, D.W.1
  • 12
    • 54249101311 scopus 로고    scopus 로고
    • Cytochrome P450 induction by rifampicin in healthy subjects: Determination using the Karolinska cocktail and the endogenous CYP3A4 marker 4β-hydroxycholesterol
    • 18650803 10.1038/clpt.2008.132 1:CAS:528:DC%2BD1cXht1OisLrL
    • Kanebratt KP, Diczfalusy U, Backstrom T, Sparve E, Bredberg E, Bottiger Y, Andersson TB, Bertilsson L (2008) Cytochrome P450 induction by rifampicin in healthy subjects: determination using the Karolinska cocktail and the endogenous CYP3A4 marker 4β-hydroxycholesterol. Clin Pharmacol Ther 84:589-594
    • (2008) Clin Pharmacol Ther , vol.84 , pp. 589-594
    • Kanebratt, K.P.1    Diczfalusy, U.2    Backstrom, T.3    Sparve, E.4    Bredberg, E.5    Bottiger, Y.6    Andersson, T.B.7    Bertilsson, L.8
  • 13
    • 79955997571 scopus 로고    scopus 로고
    • An oxysterol biomarker for 7-dehydrocholesterol oxidation in cell/mouse models for Smith-Lemli-Opitz syndrome
    • 21402677 10.1194/jlr.M014498 1:CAS:528:DC%2BC3MXmslOit7c%3D
    • Xu L, Korade Z, Rosado DA Jr, Liu W, Lamberson CR, Porter NA (2011) An oxysterol biomarker for 7-dehydrocholesterol oxidation in cell/mouse models for Smith-Lemli-Opitz syndrome. J Lipid Res 52:1222-1233
    • (2011) J Lipid Res , vol.52 , pp. 1222-1233
    • Xu, L.1    Korade, Z.2    Rosado, Jr.D.A.3    Liu, W.4    Lamberson, C.R.5    Porter, N.A.6
  • 14
    • 80051472136 scopus 로고    scopus 로고
    • Oxysterols as biomarkers in neurodegenerative diseases
    • 21515244 10.1016/j.chemphyslip.2011.04.002 1:CAS:528:DC%2BC3MXpvFCnur8%3D
    • Leoni V, Caccia C (2011) Oxysterols as biomarkers in neurodegenerative diseases. Chem Phys Lipids 164:515-524
    • (2011) Chem Phys Lipids , vol.164 , pp. 515-524
    • Leoni, V.1    Caccia, C.2
  • 15
    • 0037227662 scopus 로고    scopus 로고
    • Cyp46 (24S-cholesterol hydroxylase): A genetic risk factor for Alzheimer disease
    • 12533083 10.1001/archneur.60.1.16
    • Wolozin B (2003) Cyp46 (24S-cholesterol hydroxylase): a genetic risk factor for Alzheimer disease. Arch Neurol 60:16-18
    • (2003) Arch Neurol , vol.60 , pp. 16-18
    • Wolozin, B.1
  • 16
    • 57249113718 scopus 로고    scopus 로고
    • A facile synthesis of C-24 and C-25 oxysterols by in situ generated ethyl(trifluoromethyl)dioxirane
    • 18996406 10.1016/j.steroids.2008.09.015 1:CAS:528:DC%2BD1cXhsV2gsL3O
    • Ogawa S, Kakiyama G, Muto A, Hosoda A, Mitamura K, Ikegawa S, Hofmann AF, Iida T (2009) A facile synthesis of C-24 and C-25 oxysterols by in situ generated ethyl(trifluoromethyl)dioxirane. Steroids 74:81-87
    • (2009) Steroids , vol.74 , pp. 81-87
    • Ogawa, S.1    Kakiyama, G.2    Muto, A.3    Hosoda, A.4    Mitamura, K.5    Ikegawa, S.6    Hofmann, A.F.7    Iida, T.8
  • 17
    • 0034741051 scopus 로고    scopus 로고
    • A highly efficient, stereoselective oxyfunctionalization of unactivated carbons in steroids with dimethyldioxirane
    • 10.1039/b104938k
    • Iida T, Yamaguchi T, Nakamori R, Hikosaka M, Mano N, Goto J, Nambara T (2001) A highly efficient, stereoselective oxyfunctionalization of unactivated carbons in steroids with dimethyldioxirane. J Chem Soc Perkin Trans 1:2229-2236
    • (2001) J Chem Soc Perkin Trans , vol.1 , pp. 2229-2236
    • Iida, T.1    Yamaguchi, T.2    Nakamori, R.3    Hikosaka, M.4    Mano, N.5    Goto, J.6    Nambara, T.7
  • 18
    • 11144351962 scopus 로고    scopus 로고
    • Biomimetic oxidation of unactivated carbons in steroids by a model of cytochrome P-450, oxorutheniumporphyrinate complex
    • 10.1007/s11745-004-1309-0 1:CAS:528:DC%2BD2MXjvFGmtg%3D%3D
    • Iida T, Ogawa S, Miyata S, Goto T, Mano N, Goto J, Nambara T (2004) Biomimetic oxidation of unactivated carbons in steroids by a model of cytochrome P-450, oxorutheniumporphyrinate complex. Lipids 39:873-880
    • (2004) Lipids , vol.39 , pp. 873-880
    • Iida, T.1    Ogawa, S.2    Miyata, S.3    Goto, T.4    Mano, N.5    Goto, J.6    Nambara, T.7
  • 19
    • 0001739660 scopus 로고
    • Highly efficient oxidation of alkanes and alkyl alcohols with heteroaromatic N-oxides catalyzed by ruthenium porphyrins
    • 10.1021/ja00052a086 1:CAS:528:DyaK3sXotVWqsQ%3D%3D
    • Ohtake H, Higuchi T, Hirobe M (1992) Highly efficient oxidation of alkanes and alkyl alcohols with heteroaromatic N-oxides catalyzed by ruthenium porphyrins. J Am Chem Soc 114:10660-10662
    • (1992) J Am Chem Soc , vol.114 , pp. 10660-10662
    • Ohtake, H.1    Higuchi, T.2    Hirobe, M.3
  • 20
    • 0030913725 scopus 로고    scopus 로고
    • Regio- and stereo-selective oxidation of steroids using 2,6-dichloropyridine N-oxide catalysed by ruthenium porphyrins
    • Shingaki T, Miura K, Higuchi T, Hirobe M, Nagano T (1997) Regio- and stereo-selective oxidation of steroids using 2,6-dichloropyridine N-oxide catalysed by ruthenium porphyrins. Chem Commun 861-862
    • (1997) Chem Commun , pp. 861-862
    • Shingaki, T.1    Miura, K.2    Higuchi, T.3    Hirobe, M.4    Nagano, T.5
  • 21
    • 25844514391 scopus 로고
    • Lanthanide and aromatic solvent-induced shift effects on proton resonances in C-4-methylated steroids and tetracyclic triterpenoids
    • 10.1016/0009-3084(77)90088-3 1:CAS:528:DyaE1cXmt1GhtA%3D%3D
    • Iida T, Kikuchi M, Tamura T, Matsumoto T (1977) Lanthanide and aromatic solvent-induced shift effects on proton resonances in C-4-methylated steroids and tetracyclic triterpenoids. Chem Phys Lipids 20:157-174
    • (1977) Chem Phys Lipids , vol.20 , pp. 157-174
    • Iida, T.1    Kikuchi, M.2    Tamura, T.3    Matsumoto, T.4
  • 22
    • 0018993856 scopus 로고
    • Proton nuclear magnetic resonance identification and discrimination of side chain isomers of phytosterols using a lanthanide shift reagent
    • 7381327 1:CAS:528:DyaL3cXitFWhs70%3D
    • Iida T, Tamura T, Matsumoto T (1980) Proton nuclear magnetic resonance identification and discrimination of side chain isomers of phytosterols using a lanthanide shift reagent. J Lipid Res 21:326-338
    • (1980) J Lipid Res , vol.21 , pp. 326-338
    • Iida, T.1    Tamura, T.2    Matsumoto, T.3
  • 24
    • 84986738357 scopus 로고
    • 13C n.m.r. spectra of steroids - A survey and commentary
    • 10.1002/mrc.1270090802 1:CAS:528:DyaE1cXhtlKrsbk%3D
    • 13C n.m.r. spectra of steroids - a survey and commentary. Org Magn Reson 9:439-464
    • (1977) Org Magn Reson , vol.9 , pp. 439-464
    • Blunt, J.W.1    Stothers, J.B.2
  • 27
    • 0001034476 scopus 로고
    • The 220 MHz NMR spectra of phytosterols
    • 10.1016/S0031-9422(00)89083-4 1:CAS:528:DyaE28XhtlGqsLo%3D
    • Rubinstein I, Goad LJ, Clague ADH, Mulheirn LJ (1976) The 220 MHz NMR spectra of phytosterols. Phytochem 15:195-200
    • (1976) Phytochem , vol.15 , pp. 195-200
    • Rubinstein, I.1    Goad, L.J.2    Clague, A.D.H.3    Mulheirn, L.J.4
  • 29
    • 0001215056 scopus 로고
    • 13C chemical shifts
    • 10.1139/v76-423 1:CAS:528:DyaE2sXovV2gtw%3D%3D
    • 13C chemical shifts. Can J Chem 54:2985-2995
    • (1976) Can J Chem , vol.54 , pp. 2985-2995
    • Beierbeck, H.1    Saunders, J.K.2
  • 30
    • 33947093210 scopus 로고
    • Analysis of carbon-13 nuclear magnetic resonance for monohydroxy steroids incorporating geometric distortions
    • 10.1021/jo00400a011 1:CAS:528:DyaE1cXht1Wms7Y%3D
    • Schwenzer GM (1978) Analysis of carbon-13 nuclear magnetic resonance for monohydroxy steroids incorporating geometric distortions. J Org Chem 43:1079-1083
    • (1978) J Org Chem , vol.43 , pp. 1079-1083
    • Schwenzer, G.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.