메뉴 건너뛰기




Volumn 73, Issue 4, 2008, Pages 458-465

A simple chemical method for synthesizing malonyl hemiesters of 21-hydroxypregnanes, potential intermediates in cardenolide biosynthesis

Author keywords

21 Hydroxypregnane; Butenolide ring; Cardiac glycoside; Digitalis; Malonylation; Malonyltransferase

Indexed keywords

3 BETA ACETOXY 5 BETA PREGNANE 14 BETA 21 DIOL 20 ONE; CARDENOLIDE; DEOXYCORTICOSTERONE; PREGNANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 39549120415     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2007.12.012     Document Type: Article
Times cited : (8)

References (29)
  • 3
    • 0142197809 scopus 로고    scopus 로고
    • Acaricidal effects of cardiac glycosides, azadirachtin and neem oil against the camel tick, Hyalomma dromedarii (Acari: Ixodidae)
    • Al-Rajhy D.H., Alahmed A.M., Hussein H.I., and Kheir S.M. Acaricidal effects of cardiac glycosides, azadirachtin and neem oil against the camel tick, Hyalomma dromedarii (Acari: Ixodidae). Pest Manage Sci 59 (2003) 1250-1254
    • (2003) Pest Manage Sci , vol.59 , pp. 1250-1254
    • Al-Rajhy, D.H.1    Alahmed, A.M.2    Hussein, H.I.3    Kheir, S.M.4
  • 4
    • 33745683916 scopus 로고    scopus 로고
    • Streblus asper Lour (Shakhotaka): a review of its chemical, pharmacological and ethnomedicinal properties
    • Rastogi S., Kulshreshtha D.K., and Rawat A.K.S. Streblus asper Lour (Shakhotaka): a review of its chemical, pharmacological and ethnomedicinal properties. eCAM 3 (2006) 217-222
    • (2006) eCAM , vol.3 , pp. 217-222
    • Rastogi, S.1    Kulshreshtha, D.K.2    Rawat, A.K.S.3
  • 5
    • 0032752048 scopus 로고    scopus 로고
    • Molluscicidal activity of Pergularia tomentosa (L.), methomyl and methiocarb, against land snails
    • Hussein H.I., Al-Rajhy D., El-Shahawi F.I., and Hashem S.M. Molluscicidal activity of Pergularia tomentosa (L.), methomyl and methiocarb, against land snails. Int J Pest Manag 45 (1999) 211-213
    • (1999) Int J Pest Manag , vol.45 , pp. 211-213
    • Hussein, H.I.1    Al-Rajhy, D.2    El-Shahawi, F.I.3    Hashem, S.M.4
  • 6
    • 0032953843 scopus 로고    scopus 로고
    • A novel antibacterial and cardiac steroid from the roots of Nerium oleander
    • Huq M.M., Jabbar A., Rashid M.A., and Hasan C.M. A novel antibacterial and cardiac steroid from the roots of Nerium oleander. Fitoterapia 70 (1999) 5-9
    • (1999) Fitoterapia , vol.70 , pp. 5-9
    • Huq, M.M.1    Jabbar, A.2    Rashid, M.A.3    Hasan, C.M.4
  • 7
    • 33644974357 scopus 로고    scopus 로고
    • The cardenolide UNBS1450 is able to deactivate nuclear factor kappaB-mediated cytoprotective effects in human non-small cell lung cancer cells
    • Mijatovic T., Op De Beeck A., Van Quaquebeke E., Dewelle J., Darro F., de Launoit Y., et al. The cardenolide UNBS1450 is able to deactivate nuclear factor kappaB-mediated cytoprotective effects in human non-small cell lung cancer cells. Mol Cancer Ther 5 (2006) 391-399
    • (2006) Mol Cancer Ther , vol.5 , pp. 391-399
    • Mijatovic, T.1    Op De Beeck, A.2    Van Quaquebeke, E.3    Dewelle, J.4    Darro, F.5    de Launoit, Y.6
  • 8
    • 0031830211 scopus 로고    scopus 로고
    • Cardenolide biosynthesis in Floxglove
    • Kreis W., Hensel A., and Stuhlemmer U. Cardenolide biosynthesis in Floxglove. Planta Med 64 (1998) 491-499
    • (1998) Planta Med , vol.64 , pp. 491-499
    • Kreis, W.1    Hensel, A.2    Stuhlemmer, U.3
  • 9
    • 34447268136 scopus 로고    scopus 로고
    • The mevalonate and deoxyxylulose phosphate pathways: terpenoids and steroids
    • John Wiley & Sons, New York pp. 167-289
    • Dewick P.M. The mevalonate and deoxyxylulose phosphate pathways: terpenoids and steroids. Medicinal natural products. A biosynthetic approach (2001), John Wiley & Sons, New York pp. 167-289
    • (2001) Medicinal natural products. A biosynthetic approach
    • Dewick, P.M.1
  • 11
    • 0030794759 scopus 로고    scopus 로고
    • Effects of various pregnanes and two 23-nor-5-cholenic acids on cardenolide accumulation in cell and organ cultures of Digitalis lanata
    • Haussmann W., Kreis W., Stuhlemmer U., and Reinhard E. Effects of various pregnanes and two 23-nor-5-cholenic acids on cardenolide accumulation in cell and organ cultures of Digitalis lanata. Planta Med 63 (1997) 446-453
    • (1997) Planta Med , vol.63 , pp. 446-453
    • Haussmann, W.1    Kreis, W.2    Stuhlemmer, U.3    Reinhard, E.4
  • 12
    • 0015507258 scopus 로고
    • Biosynthesis of cardenolides, bufadienolides and steroid sapogenins
    • Tschesche R. Biosynthesis of cardenolides, bufadienolides and steroid sapogenins. Proc R Soc Lond B 180 (1972) 187-202
    • (1972) Proc R Soc Lond B , vol.180 , pp. 187-202
    • Tschesche, R.1
  • 13
    • 0012977301 scopus 로고
    • Neue Beiträge zur Biogenese der Cardenolide in Digitalis lanata
    • Tschesche R., Hombach R., Scholten H., and Peters M. Neue Beiträge zur Biogenese der Cardenolide in Digitalis lanata. Phytochemistry 9 (1970) 1505-1515
    • (1970) Phytochemistry , vol.9 , pp. 1505-1515
    • Tschesche, R.1    Hombach, R.2    Scholten, H.3    Peters, M.4
  • 14
    • 84984085863 scopus 로고
    • Die Biosynthese des Digitoxigenins, Herkunft des C-20
    • Euw J.V., and Reichstein T. Die Biosynthese des Digitoxigenins, Herkunft des C-20. Helv Chim Acta 47 (1964) 711-724
    • (1964) Helv Chim Acta , vol.47 , pp. 711-724
    • Euw, J.V.1    Reichstein, T.2
  • 15
    • 0005646979 scopus 로고
    • Biosynthesis of plants steroids. I. The origin of the butenolide ring of digitoxigenin
    • Leete E., Gregory H., and Gros E.G. Biosynthesis of plants steroids. I. The origin of the butenolide ring of digitoxigenin. J Am Chem Soc 87 (1965) 3475-3479
    • (1965) J Am Chem Soc , vol.87 , pp. 3475-3479
    • Leete, E.1    Gregory, H.2    Gros, E.G.3
  • 16
    • 0029916434 scopus 로고    scopus 로고
    • Does the malonyl-coenzyme A:21-hydroxypregnane 21-hydroxymalonyltransferase catalyse the first step in the formation of the butenolide ring of cardenolides?
    • Stuhlemmer U., and Kreis W. Does the malonyl-coenzyme A:21-hydroxypregnane 21-hydroxymalonyltransferase catalyse the first step in the formation of the butenolide ring of cardenolides?. Tetrahedron Lett 37 (1996) 2221-2224
    • (1996) Tetrahedron Lett , vol.37 , pp. 2221-2224
    • Stuhlemmer, U.1    Kreis, W.2
  • 17
    • 0030668871 scopus 로고    scopus 로고
    • GLC-MS investigations on cardenolide genins
    • Hensel A., and Kreis W. GLC-MS investigations on cardenolide genins. Pharm Acta Helv 72 (1997) 243-246
    • (1997) Pharm Acta Helv , vol.72 , pp. 243-246
    • Hensel, A.1    Kreis, W.2
  • 19
    • 0015137907 scopus 로고
    • Ozon/Pyridin-Abbau der Cardenolidtrigiditoxoside Digitoxin and Digoxin zu Isopregnanolontridigitoxosiden
    • Rabitzsch G. Ozon/Pyridin-Abbau der Cardenolidtrigiditoxoside Digitoxin and Digoxin zu Isopregnanolontridigitoxosiden. Pharmazie 26 (1971) 592-597
    • (1971) Pharmazie , vol.26 , pp. 592-597
    • Rabitzsch, G.1
  • 20
    • 37049080243 scopus 로고
    • Synthesis of the 3β, 14β-dihydroxy-5β-pregnan-20-one C-3 derivates: ozonolysis of digitoxin and digitoxigenin and their derivates followed by zinc-acetic acid reduction to the C-21 methyl ketone.
    • Templeton J.F., Ling Y., Jin J., Boehmer M.A., Zeglam T.H., and LaBella F.S. Synthesis of the 3β, 14β-dihydroxy-5β-pregnan-20-one C-3 derivates: ozonolysis of digitoxin and digitoxigenin and their derivates followed by zinc-acetic acid reduction to the C-21 methyl ketone. J Chem Soc, Perkin Trans I (1991) 823-829
    • (1991) J Chem Soc, Perkin Trans I , pp. 823-829
    • Templeton, J.F.1    Ling, Y.2    Jin, J.3    Boehmer, M.A.4    Zeglam, T.H.5    LaBella, F.S.6
  • 22
    • 33747855471 scopus 로고    scopus 로고
    • Reaction of methyl thiocarbamate with nonsubstituted malonyl dichloride. Effect of conditions on reaction direction
    • Lalaev B.Y., Yakovlev I.P., and Zakhs V.E. Reaction of methyl thiocarbamate with nonsubstituted malonyl dichloride. Effect of conditions on reaction direction. Russ J Gen Chem 76 (2006) 133-134
    • (2006) Russ J Gen Chem , vol.76 , pp. 133-134
    • Lalaev, B.Y.1    Yakovlev, I.P.2    Zakhs, V.E.3
  • 23
    • 0035940720 scopus 로고    scopus 로고
    • Gas chromatography and high performance liquid chromatography of natural steroids
    • Shimada K., Mitamura K., and Higashi T. Gas chromatography and high performance liquid chromatography of natural steroids. J Chromatogr A 935 (2001) 141-172
    • (2001) J Chromatogr A , vol.935 , pp. 141-172
    • Shimada, K.1    Mitamura, K.2    Higashi, T.3
  • 24
    • 4444236940 scopus 로고    scopus 로고
    • Derivatization of neural steroids to enhance their detection characteristics in liquid chromatography-mass spectrometry
    • Higashi T., and Shimada K. Derivatization of neural steroids to enhance their detection characteristics in liquid chromatography-mass spectrometry. Anal Bioanal Chem 378 (2004) 875-882
    • (2004) Anal Bioanal Chem , vol.378 , pp. 875-882
    • Higashi, T.1    Shimada, K.2
  • 26
    • 39549098031 scopus 로고    scopus 로고
    • LC-MS-Hinweise zur Optimierung und Fehlersuche
    • Kromidas S. (Ed), Wiley-VCH, Weinheim
    • Mandel F., and Kopplungstechniken. LC-MS-Hinweise zur Optimierung und Fehlersuche. In: Kromidas S. (Ed). HPLC richtig optimiert (2006), Wiley-VCH, Weinheim 529-586
    • (2006) HPLC richtig optimiert , pp. 529-586
    • Mandel, F.1    Kopplungstechniken2
  • 27
    • 0024204856 scopus 로고
    • Structural analysis of 21-hydroxypregn-4-ene-3,20-dione (deoxycorticosterone, DOC) derivative compounds. Part II. Proton NMR spectra
    • Kouadio L., Bernard P., Sabot J.F., Petit-Ramel M.M., Barbier C.M., and Pinatel H.J. Structural analysis of 21-hydroxypregn-4-ene-3,20-dione (deoxycorticosterone, DOC) derivative compounds. Part II. Proton NMR spectra. Steroids 51 (1988) 363-384
    • (1988) Steroids , vol.51 , pp. 363-384
    • Kouadio, L.1    Bernard, P.2    Sabot, J.F.3    Petit-Ramel, M.M.4    Barbier, C.M.5    Pinatel, H.J.6
  • 28
    • 37049081387 scopus 로고
    • A survey of the high-field 1H NMR spectra of the steroid hormones, their hydroxylated derivatives, and related compounds
    • Kirk D.N., Toms H.C., Douglas C., White K.A., Smith K.E., Latif S., et al. A survey of the high-field 1H NMR spectra of the steroid hormones, their hydroxylated derivatives, and related compounds. J Chem Soc, Perkin Trans 2 (1990) 1567-1594
    • (1990) J Chem Soc, Perkin Trans , vol.2 , pp. 1567-1594
    • Kirk, D.N.1    Toms, H.C.2    Douglas, C.3    White, K.A.4    Smith, K.E.5    Latif, S.6
  • 29
    • 38349164512 scopus 로고    scopus 로고
    • Purification and characterization of malonyl-coenzyme: 21-Hydroxypregnane 21-O-malonyltransferase (Dp21MaT) from leaves of Digitalis purpurea L.
    • Kuate S.P., Pádua R.M., Eisenbeiss W.F., and Kreis W. Purification and characterization of malonyl-coenzyme: 21-Hydroxypregnane 21-O-malonyltransferase (Dp21MaT) from leaves of Digitalis purpurea L. Phytochemistry 69 (2008) 619-626
    • (2008) Phytochemistry , vol.69 , pp. 619-626
    • Kuate, S.P.1    Pádua, R.M.2    Eisenbeiss, W.F.3    Kreis, W.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.