메뉴 건너뛰기




Volumn 75, Issue 12, 2010, Pages 879-883

A concise synthesis of β-sitosterol and other phytosterols

Author keywords

Campesterol; Deoxygenation; Epoxide; Phytosterol; Sitosterol; Synthesis

Indexed keywords

(3BETA,5ALPHA,6ALPHA)ERGOST 5,6 EPOXY 22 EN 3 YL ACETATE; (3BETA,5ALPHA,6ALPHA)PREGNANE 20 BETA CARBOXALDEHYDE 5,6 EPOXY 3 YL ACETATE; (3BETA,5BETA,6BETA)ERGOST 5,6 EPOXY 22 EN 3 YL ACETATE; (3BETA,5BETA,6BETA)PREGNANE 20 BETA CARBOXALDEHYDE 5,6 EPOXY 3 YL ACETATE; 2 (2,3 DIMETHYLBUTYLSULFONYL)BENZOTHIAZOLE; 2 (2,3 DIMETHYLBUTYLTHIO)BENZOTHIAZOLE; 2,3 DIMETHYLBUTAN 1 OL; 5ALPHA,6ALPHA EPOXIDE; 5ALPHA,6ALPHA EPOXYSITOSTEROL ACETATE; 5BETA,6BETA EPOXIDE; 5BETA,6BETA EPOXYSITOSTEROL ACETATE; ALKENE; CAMPESTEROL ACETATE; EPOXIDE; PHYTOSTEROL; PORIFERASTEROL; SITOSTEROL; STIGMASTEROL; UNCLASSIFIED DRUG;

EID: 77955925616     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2010.05.016     Document Type: Article
Times cited : (25)

References (27)
  • 1
    • 0034705517 scopus 로고    scopus 로고
    • Pharmacolgical properties of plant sterols: In vivo and in vitro observations
    • M.H. Moghadasian Pharmacolgical properties of plant sterols: in vivo and in vitro observations Life Sci 67 2000 605 615
    • (2000) Life Sci , vol.67 , pp. 605-615
    • Moghadasian, M.H.1
  • 2
    • 0034657215 scopus 로고    scopus 로고
    • Plant sterols: Biosynthesis, biological function and their importance to human nutrition
    • V. Piironen, D.G. Lindsay, T.A. Miettinen, J. Toivo, and A.M. Lampi Plant sterols: biosynthesis, biological function and their importance to human nutrition J Sci Food Agric 80 2000 939 966
    • (2000) J Sci Food Agric , vol.80 , pp. 939-966
    • Piironen, V.1    Lindsay, D.G.2    Miettinen, T.A.3    Toivo, J.4    Lampi, A.M.5
  • 3
    • 0029035238 scopus 로고
    • Dietary phytosterols: A review of metabolism, benefits and side effects
    • W.H. Ling, and P.J.H. Jone Dietary phytosterols: a review of metabolism, benefits and side effects Life Sci 57 1995 195 206
    • (1995) Life Sci , vol.57 , pp. 195-206
    • Ling, W.H.1    Jone, P.J.H.2
  • 4
    • 33845959674 scopus 로고    scopus 로고
    • Sitosterol-containing lipoproteins trigger free sterol-induced caspase-independent death in ACAT-competent macrophages
    • L. Bao, Y. Li, S.X. Deng, D. Landry, and I. Tabas Sitosterol-containing lipoproteins trigger free sterol-induced caspase-independent death in ACAT-competent macrophages J Biol Chem 281 2006 33635 33649
    • (2006) J Biol Chem , vol.281 , pp. 33635-33649
    • Bao, L.1    Li, Y.2    Deng, S.X.3    Landry, D.4    Tabas, I.5
  • 5
    • 77949460855 scopus 로고    scopus 로고
    • The effects of pomegranate seed extract and β-sitosterol on rat uterine contractions
    • W. Promprom, P. Kupittayanant, K. Indrapichate, S. Wray, and S. Kupittayanant The effects of pomegranate seed extract and β-sitosterol on rat uterine contractions Reprod Sci 17 2010 288 296
    • (2010) Reprod Sci , vol.17 , pp. 288-296
    • Promprom, W.1    Kupittayanant, P.2    Indrapichate, K.3    Wray, S.4    Kupittayanant, S.5
  • 6
    • 77955920418 scopus 로고    scopus 로고
    • Plant sterol and stanol substrate specificity of pancreatic cholesterol ester lipase
    • A.W. Brown, J. Hang, P.H. Dussault, and T. Carr Plant sterol and stanol substrate specificity of pancreatic cholesterol ester lipase J Nutr Biochem 2009 Available online 16 July 2009
    • (2009) J Nutr Biochem
    • Brown, A.W.1    Hang, J.2    Dussault, P.H.3    Carr, T.4
  • 7
    • 33751110656 scopus 로고    scopus 로고
    • Reduction in cholesterol absorption is enhanced by stearate-enriched plant sterol esters in hamsters
    • H.E. Rasmussen, D.M. Guderian Jr., C.A. Wray, P.H. Dussault, V.L. Schlegel, and T. Carr Reduction in cholesterol absorption is enhanced by stearate-enriched plant sterol esters in hamsters J Nutr 136 2006 2722 2727
    • (2006) J Nutr , vol.136 , pp. 2722-2727
    • Rasmussen, H.E.1    Guderian Jr., D.M.2    Wray, C.A.3    Dussault, P.H.4    Schlegel, V.L.5    Carr, T.6
  • 9
    • 27644580817 scopus 로고    scopus 로고
    • Gram-scale chromatographic purification of β-sitosterol: Synthesis and characterization of β-sitosterol oxides
    • X. Zhang, P. Geoffroy, M. Miesch, D. Julien-David, F. Raul, and D. Aoude-Werner Gram-scale chromatographic purification of β-sitosterol: synthesis and characterization of β-sitosterol oxides Steroids 70 2005 886 895
    • (2005) Steroids , vol.70 , pp. 886-895
    • Zhang, X.1    Geoffroy, P.2    Miesch, M.3    Julien-David, D.4    Raul, F.5    Aoude-Werner, D.6
  • 10
    • 51649171162 scopus 로고
    • Purification of sitosterol
    • H.W. Kircher, and F.U. Rosenstein Purification of sitosterol Lipids 8 1973 97 100
    • (1973) Lipids , vol.8 , pp. 97-100
    • Kircher, H.W.1    Rosenstein, F.U.2
  • 11
    • 43849103835 scopus 로고    scopus 로고
    • Synthesis of highly pure oxyphytosterols and (oxy)phytosterol esters: Part I. Regioselective hydrogenation of stigmasterol: An easy access to oxyphytosterols
    • For an overview of stigmasterol hydrogenation, see: P. Geoffroy, D. Julien-David, E. Marchioni, F. Raul, D. Aoude-Werner, and M. Miesch Synthesis of highly pure oxyphytosterols and (oxy)phytosterol esters: Part I. Regioselective hydrogenation of stigmasterol: an easy access to oxyphytosterols Steroids 73 2008 702 707
    • (2008) Steroids , vol.73 , pp. 702-707
    • Geoffroy, P.1    Julien-David, D.2    Marchioni, E.3    Raul, F.4    Aoude-Werner, D.5    Miesch, M.6
  • 12
    • 5544295969 scopus 로고
    • The Solvolysis of Stigmasteryl tosylate
    • J.A. Steele, and E. Mosettig The Solvolysis of Stigmasteryl tosylate J Org Chem 28 1963 571 572
    • (1963) J Org Chem , vol.28 , pp. 571-572
    • Steele, J.A.1    Mosettig, E.2
  • 14
    • 19344363060 scopus 로고    scopus 로고
    • Preparation of (25R)- and (25S)-26-functionalized steroids as tools for biosynthetic studies of cholic acids
    • For an application to sidechain-modified steroids, see: V.A. Khripach, V.N. Zhabinskii, O.V. Konstantinova, N.B. Khripach, A.V. Antonchick, A.P. Antonchick, and B. Schneider Preparation of (25R)- and (25S)-26-functionalized steroids as tools for biosynthetic studies of cholic acids Steroids 70 2005 551 562
    • (2005) Steroids , vol.70 , pp. 551-562
    • Khripach, V.A.1    Zhabinskii, V.N.2    Konstantinova, O.V.3    Khripach, N.B.4    Antonchick, A.V.5    Antonchick, A.P.6    Schneider, B.7
  • 15
    • 0002277673 scopus 로고
    • Aluminum triiodide: A convenient reagent for deoxygenation of oxiranes
    • P. Sarmah, and N.C. Barua Aluminum triiodide: a convenient reagent for deoxygenation of oxiranes Tetrahedron Lett 29 1988 5815 5816
    • (1988) Tetrahedron Lett , vol.29 , pp. 5815-5816
    • Sarmah, P.1    Barua, N.C.2
  • 17
    • 64349123859 scopus 로고    scopus 로고
    • A study of the epoxidation of cycloolefins by the t-BuOH copper-permanganate system
    • Y. Baqi, S. Giroux, and E.J. Corey A study of the epoxidation of cycloolefins by the t-BuOH copper-permanganate system Org Lett 11 2009 959 961
    • (2009) Org Lett , vol.11 , pp. 959-961
    • Baqi, Y.1    Giroux, S.2    Corey, E.J.3
  • 18
    • 33845943238 scopus 로고    scopus 로고
    • Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide
    • S.M. Wang, Y.B. Zhang, H.M. Liu, G.B. Yu, and K.R. Wang Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide Steroids 72 2007 26 30
    • (2007) Steroids , vol.72 , pp. 26-30
    • Wang, S.M.1    Zhang, Y.B.2    Liu, H.M.3    Yu, G.B.4    Wang, K.R.5
  • 19
    • 38849133490 scopus 로고    scopus 로고
    • Enantioselective synthesis of 2-substituted alcohols using (+)-(1S,2S)-pseudoephedrine as chiral auxiliary
    • L.F. Tietze, C. Raith, C.C. Brazel, S. Hoelsken, and J. Magull Enantioselective synthesis of 2-substituted alcohols using (+)-(1S,2S)- pseudoephedrine as chiral auxiliary Synthesis 2008 229 236
    • (2008) Synthesis , pp. 229-236
    • Tietze, L.F.1    Raith, C.2    Brazel, C.C.3    Hoelsken, S.4    Magull, J.5
  • 23
    • 77955926225 scopus 로고    scopus 로고
    • 23.
    • 23
  • 25
    • 0037038993 scopus 로고    scopus 로고
    • The modified Julia olefination: Alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds
    • P.R. Blakemore The modified Julia olefination: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds Perkins 1 2002 2563 2585
    • (2002) Perkins , vol.1 , pp. 2563-2585
    • Blakemore, P.R.1
  • 26
    • 84990805234 scopus 로고
    • Benzothiazole compounds. XVII. 2-Alkyl- and 2- aralkylsulfonylbenzothiazoles and their antimicrobial activity
    • V. Sutoris, P. Foltinova, and A. Gaplovsky Benzothiazole compounds. XVII. 2-Alkyl- and 2-aralkylsulfonylbenzothiazoles and their antimicrobial activity Chem Zvesti 34 1980 404 412
    • (1980) Chem Zvesti , vol.34 , pp. 404-412
    • Sutoris, V.1    Foltinova, P.2    Gaplovsky, A.3
  • 27
    • 37649017392 scopus 로고    scopus 로고
    • Synthesis of enol ethers from lactones using modified Julia olefination reagents: Application to the preparation of tri- and tetrasubstituted exoglycals
    • B. Bourdon, M. Corbet, P. Fontaine, P.G. Goekjian, and D. Gueyrard Synthesis of enol ethers from lactones using modified Julia olefination reagents: application to the preparation of tri- and tetrasubstituted exoglycals Tetrahedron Lett 49 2008 747 749
    • (2008) Tetrahedron Lett , vol.49 , pp. 747-749
    • Bourdon, B.1    Corbet, M.2    Fontaine, P.3    Goekjian, P.G.4    Gueyrard, D.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.