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Volumn 77, Issue 3, 2012, Pages 250-254

Novel stereoselective synthesis and chromatographic evaluation of E-guggulsterone

Author keywords

FXR; Guggulsterone; HPLC; Stereoselective synthesis

Indexed keywords

ANDROSTENEDIONE; GUGGULSTERONE;

EID: 84855900100     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2011.11.012     Document Type: Article
Times cited : (16)

References (34)
  • 1
    • 0005350144 scopus 로고
    • A promising hypolipidemic agent from gum guggul (Commiphora wightii)
    • G.V. Satyavati A promising hypolipidemic agent from gum guggul (Commiphora wightii) Econ Med Plant Res 5 1991 47 82
    • (1991) Econ Med Plant Res , vol.5 , pp. 47-82
    • Satyavati, G.V.1
  • 2
    • 0042130513 scopus 로고    scopus 로고
    • Gugulipid: A natural cholesterol-lowering agent
    • DOI 10.1146/annurev.nutr.23.011702.073102
    • N.L. Urizar, and D.D. Moore Guggulipid: a natural cholesterol lowering agent Ann Rev Nutr 23 2003 303 313 (Pubitemid 37059726)
    • (2003) Annual Review of Nutrition , vol.23 , pp. 303-313
    • Urizar, N.L.1    Moore, D.D.2
  • 4
    • 0015665269 scopus 로고
    • Cholesterol lowering activity of the various fractions of guggul
    • S. Nityanand, and N.K. Kapoor Cholesterol lowering activity of the various fractions of guggul Indian J Exp Biol 11 1973 395 398
    • (1973) Indian J Exp Biol , vol.11 , pp. 395-398
    • Nityanand, S.1    Kapoor, N.K.2
  • 6
    • 0842281422 scopus 로고    scopus 로고
    • The hypolipidemic natural product Commiphora mukul and its component guggulsterone inhibit oxidative modification of LDL
    • DOI 10.1016/j.atherosclerosis.2003.10.008
    • X. Wang, J. Greilberger, G. Ledinski, G. Kager, B. Paigen, and G. Jurgens The hypolipidemic natural product Commiphora mukul and its component guggulsterone inhibit oxidative modification of LDL Atherosclerosis 172 2004 239 246 (Pubitemid 38167534)
    • (2004) Atherosclerosis , vol.172 , Issue.2 , pp. 239-246
    • Wang, X.1    Greilberger, J.2    Ledinski, G.3    Kager, G.4    Paigen, B.5    Jurgens, G.6
  • 7
    • 36849034877 scopus 로고    scopus 로고
    • Therapeutic effects of guggul and its constituent guggulsterone: Cardiovascular benefits
    • DOI 10.1111/j.1527-3466.2007.00023.x
    • R. Deng Therapeutic effects of guggul and its constituent guggulsterone: cardiovascular benefits Cardiovascular Drug Rev 25 2007 375 390 (Pubitemid 350233357)
    • (2007) Cardiovascular Drug Reviews , vol.25 , Issue.4 , pp. 375-390
    • Deng, R.1
  • 8
    • 8744234076 scopus 로고    scopus 로고
    • Guggulsterone inhibits NF-κB and IκBα kinase activation, suppresses expression of anti-apoptotic gene products, and enhances apoptosis
    • DOI 10.1074/jbc.M408093200
    • S. Shishodia, and B.B. Aggarwal Guggulsterone inhibits NF-kappaB and IkappaBalpha kinase activation, suppresses expression of anti-apoptotic gene products, and enhances apoptosis J Biol Chem 279 2004 47148 47158 (Pubitemid 39518371)
    • (2004) Journal of Biological Chemistry , vol.279 , Issue.45 , pp. 47148-47158
    • Shishodia, S.1    Aggarwal, B.B.2
  • 10
    • 0003295132 scopus 로고    scopus 로고
    • Guggulsterone is a farnesoid X receptor antagonist in coactivator association assays but acts to enhance transcription of bile salt export pump
    • DOI 10.1074/jbc.M209323200
    • J. Cui, L. Huang, A. Zhao, J.L. Lew, S. Sahoo, P.T. Meinke, I. Royo, F. Pelaez, and S.D. Wright Guggulsterone is a farnesoid X receptor antagonist in coactivator association assays but acts to enhance transcription of bile salt export pump J Biol Chem 278 2003 10214 10220 (Pubitemid 36800282)
    • (2003) Journal of Biological Chemistry , vol.278 , Issue.12 , pp. 10214-10220
    • Cui, J.1    Huang, L.2    Zhao, A.3    Lew, J.-L.4    Yu, J.5    Sahoo, S.6    Meinke, P.T.7    Royo, I.8    Pelaez, F.9    Wright, S.D.10
  • 11
    • 85047685018 scopus 로고    scopus 로고
    • The hypolipidemic natural product guggulsterone acts as an antagonist of the bile acid receptor
    • DOI 10.1210/me.16.7.1590
    • J. Wu, C. Xia, J. Meier, S. Li, X. Hu, and D.S. Lala The hypolipidemic natural product guggulsterone acts as an antagonist of the bile acid receptor Mol Endocrinol 16 2002 1590 1597 (Pubitemid 34743677)
    • (2002) Molecular Endocrinology , vol.16 , Issue.7 , pp. 1590-1597
    • Wu, J.1    Xia, C.2    Meier, J.3    Li, S.4    Hu, X.5    Lala, D.S.6
  • 12
    • 53349108487 scopus 로고    scopus 로고
    • Guggulsterone modulates MAPK and NF-κB pathways and inhibits skin tumorigenesis in SENCAR mice
    • S. Sarfaraz, I.A. Siddiqui, D.N. Syed, F. Afaq, and H. Mukhatar Guggulsterone modulates MAPK and NF-κB pathways and inhibits skin tumorigenesis in SENCAR mice Carcinogenesis 29 2008 2011 2018
    • (2008) Carcinogenesis , vol.29 , pp. 2011-2018
    • Sarfaraz, S.1    Siddiqui, I.A.2    Syed, D.N.3    Afaq, F.4    Mukhatar, H.5
  • 14
    • 39449104855 scopus 로고    scopus 로고
    • Guggulsterone inhibits adipocyte differentiation and induces apoptosis in 3T3-L1 Cells
    • DOI 10.1038/oby.2007.24, PII OBY200724
    • J.Y. Yang, M.A. Della Fera, and C.A. Baile Guggulsterone inhibits adipocyte differentiation and induces apoptosis in 3t3-l1 cells Obesity 16 2008 16 22 (Pubitemid 351271944)
    • (2008) Obesity , vol.16 , Issue.1 , pp. 16-22
    • Yang, J.-Y.1    Della-Fera, M.A.2    Baile, C.A.3
  • 17
    • 0000431437 scopus 로고
    • The synthesis and stereochemistry of isomeric 16-hydroxy-17(20)-pregnenes
    • W.R. Benn, and R.M. Dodson The synthesis and stereochemistry of isomeric 16-hydroxy-17(20)-pregnenes J Org Chem 29 1964 1142 1148
    • (1964) J Org Chem , vol.29 , pp. 1142-1148
    • Benn, W.R.1    Dodson, R.M.2
  • 18
    • 0000400994 scopus 로고
    • Chemistry of ayurvedic crude drugs: Guggulu (resin from commiphora mukul) - 1: Steroidal constituents
    • V.D. Patil, U.R. Nayak, and S. Dev Chemistry of ayurvedic crude drugs: guggulu (resin from commiphora mukul) - 1: steroidal constituents Tetrahedron 28 1972 2341 2352
    • (1972) Tetrahedron , vol.28 , pp. 2341-2352
    • Patil, V.D.1    Nayak, U.R.2    Dev, S.3
  • 21
    • 79957614233 scopus 로고    scopus 로고
    • A regioselective synthesis of E-guggulsterone
    • J. Ham, J. Chin, and H. Kang A regioselective synthesis of E-guggulsterone Molecules 16 2011 4171 4615
    • (2011) Molecules , vol.16 , pp. 4171-4615
    • Ham, J.1    Chin, J.2    Kang, H.3
  • 23
    • 4143056853 scopus 로고    scopus 로고
    • Bile acid derivatives as ligands of the farnesoid X receptor. Synthesis, evaluation, and structure - Activity relationship of a series of body and side chain modified analogues of chenodeoxycholic acid
    • DOI 10.1021/jm049904b
    • R. Pellicciari, G. Costantino, E. Camaioni, B.M. Sadeghpour, A. Entrena, T.M. Willson, S. Fiorucci, C. Clerici, and A. Gioiello Bile acid derivatives as ligands of the farnesoid X receptor Synthesis, evaluation, and structure-activity relationship of a series of body and side chain modified analogues of chenodeoxycholic acid J Med Chem 47 2004 4559 4569 (Pubitemid 39096842)
    • (2004) Journal of Medicinal Chemistry , vol.47 , Issue.18 , pp. 4559-4569
    • Pellicciari, R.1    Costantino, G.2    Camaioni, E.3    Sadeghpour, B.M.4    Entrena, A.5    Willson, T.M.6    Fiorucci, S.7    Clerici, C.8    Gioiello, A.9
  • 24
    • 33745852636 scopus 로고    scopus 로고
    • Back door modulation of the farnesoid X receptor: Design, synthesis, and biological evaluation of a series of side chain modified chenodeoxycholic acid derivatives
    • DOI 10.1021/jm060294k
    • R. Pellicciari, A. Gioiello, G. Costantino, B.M. Sadeghpour, G. Rizzo, D.J. Parks, A. Entrena-Guadix, and S. Fiorucci Back door modulation of the farnesoid x receptor (FXR): design, synthesis and biological evaluation of a series of side chain-modified chenodeoxycholic acid derivatives J Med Chem 49 2006 4208 4215 (Pubitemid 44036664)
    • (2006) Journal of Medicinal Chemistry , vol.49 , Issue.14 , pp. 4208-4215
    • Pellicciari, R.1    Gioiello, A.2    Costantino, G.3    Sadeghpour, B.M.4    Rizzo, G.5    Meyer, U.6    Parks, D.J.7    Entrena-Guadix, A.8    Fiorucci, S.9
  • 25
    • 79954416610 scopus 로고    scopus 로고
    • Extending SAR of bile acids as FXR ligands: Discovery of 23-N-(carbocinnamyloxy)-3α, 7α-dihydroxy-6α-ethyl-24-nor- 5β-cholan-23-amine
    • A. Gioiello, A. Macchiarulo, A. Carotti, P. Filipponi, G. Costantino, G. Rizzo, L. Adorini, and R. Pellicciari Extending SAR of bile acids as FXR ligands: discovery of 23-N-(carbocinnamyloxy)-3α, 7α-dihydroxy- 6α-ethyl-24-nor-5β-cholan-23-amine Bioorg Med Chem 19 2011 2650 2658
    • (2011) Bioorg Med Chem , vol.19 , pp. 2650-2658
    • Gioiello, A.1    MacChiarulo, A.2    Carotti, A.3    Filipponi, P.4    Costantino, G.5    Rizzo, G.6    Adorini, L.7    Pellicciari, R.8
  • 27
    • 0034829735 scopus 로고    scopus 로고
    • A new strategy for the stereoselective introduction of steroid side chain via α-alkoxy vinyl cuprates: Total synthesis of a highly potent antitumor natural product OSW-1 [2]
    • DOI 10.1021/ja004098t
    • W. Yu, and Z. Jin A new strategy for the stereoselective introduction of steroid side chain via α-alkoxy vinyl cuprates: total synthesis of a highly potent antitumor natural product OSW-1 J Am Chem Soc 123 2001 3369 3370 (Pubitemid 32884627)
    • (2001) Journal of the American Chemical Society , vol.123 , Issue.14 , pp. 3369-3370
    • Yu, W.1    Jin, Z.2
  • 28
    • 0001116524 scopus 로고
    • Organocuprate-mediated methods for the stereospecific introduction of steroid side chains at C-20
    • N.R. Schmuff, and B.M. Trost Organocuprate-mediated methods for the stereospecific introduction of steroid side chains at C-20 J Org Chem 48 1983 1404 1412
    • (1983) J Org Chem , vol.48 , pp. 1404-1412
    • Schmuff, N.R.1    Trost, B.M.2
  • 29
    • 0032562523 scopus 로고    scopus 로고
    • Simultaneous determination of the stereoisomers of guggulsterone in serum by high-performance liquid chromatography
    • DOI 10.1016/S0378-4347(97)00626-9, PII S0378434797006269
    • N. Verma, S.K. Singh, and R.C. Gupta Simultaneous determination of the stereoisomers of guggulsterone in serum by high-performance liquid chromatography J Chromatogr B 708 1998 243 248 (Pubitemid 28239911)
    • (1998) Journal of Chromatography B: Biomedical Applications , vol.708 , Issue.1-2 , pp. 243-248
    • Verma, N.1    Singh, S.K.2    Gupta, R.C.3
  • 30
    • 79961129733 scopus 로고    scopus 로고
    • Simultaneous estimation of E- and Z-isomers of guggulsterone in rabbit plasma using liquid chromatography tandem mass spectrometry and its application to pharmacokinetic study
    • doi:10.1002/bmc.1574
    • Bhatta RS, Kumar D, Chhonker YS, Jain GK. Simultaneous estimation of E- and Z-isomers of guggulsterone in rabbit plasma using liquid chromatography tandem mass spectrometry and its application to pharmacokinetic study. Biomed Chromatogr. doi:10.1002/bmc.1574.
    • Biomed Chromatogr.
    • Bhatta, R.S.1    Kumar, D.2    Chhonker, Y.S.3    Jain, G.K.4
  • 31
    • 0032509463 scopus 로고    scopus 로고
    • High-performance liquid chromatographic method for fingerprinting and quantitative determination of E- and Z-guggulsterones in Commiphora mukul resin and its products
    • DOI 10.1016/S0378-4347(98)00433-2, PII S0378434798004332
    • B. Mesrob, C. Nesbitt, R. Misra, and R.C. Pandey High-performance liquid chromatographic method for fingerprinting and quantitative determination of E- and Z-guggulsterones in Commiphora mukul resin and its products J Chromatogr B 720 1998 189 196 (Pubitemid 29000946)
    • (1998) Journal of Chromatography B: Biomedical Applications , vol.720 , Issue.1-2 , pp. 189-196
    • Mesrob, B.1    Nesbitt, C.2    Misra, R.3    Pandey, R.C.4
  • 32
    • 84889442369 scopus 로고    scopus 로고
    • Role of polysaccharides in chiral separations by liquid chromatography and capillary electrophoresis
    • S. Subramanian, 3rd ed. Wiley-VCH Verlag GmbH & Co. KGaA Weinheim
    • I. Ali, and H.Y. Aboul-Enein Role of polysaccharides in chiral separations by liquid chromatography and capillary electrophoresis S. Subramanian, Chiral separation techniques 3rd ed. 2007 Wiley-VCH Verlag GmbH & Co. KGaA Weinheim 29 97
    • (2007) Chiral Separation Techniques , pp. 29-97
    • Ali, I.1    Aboul-Enein, H.Y.2
  • 33
    • 84889433836 scopus 로고    scopus 로고
    • Analytical and preparative potential of immobilized polysaccharide- derived chiral stationary phases
    • S. Subramanian, 3rd ed. Wiley-VCH Verlag GmbH & Co. KGaA Weinheim
    • T. Zhang, and P. Franco Analytical and preparative potential of immobilized polysaccharide-derived chiral stationary phases S. Subramanian, Chiral separation techniques 3rd ed. 2007 Wiley-VCH Verlag GmbH & Co. KGaA Weinheim 99 134
    • (2007) Chiral Separation Techniques , pp. 99-134
    • Zhang, T.1    Franco, P.2
  • 34
    • 33748940093 scopus 로고    scopus 로고
    • The farnesoid X receptor promotes adipocyte differentiation and regulates adipose cell function in vivo
    • DOI 10.1124/mol.106.023820
    • G. Rizzo, M. Disante, A. Mencarelli, B. Renga, A. Gioiello, R. Pellicciari, and S. Fiorucci The farnesoid X receptor promotes adipocyte differentiation and regulates adipose cell function in vivo Mol Pharmacol 70 2006 1164 1173 (Pubitemid 44435967)
    • (2006) Molecular Pharmacology , vol.70 , Issue.4 , pp. 1164-1173
    • Rizzo, G.1    Disante, M.2    Mencarelli, A.3    Renga, B.4    Gioiello, A.5    Pellicciari, R.6    Fiorucci, S.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.