A new look into the reaction between ergosterol and singlet oxygen in vitro.
作者： Mar??a A. Ponce , Javier A. Ramirez , Lydia R. Galagovsky , Eduardo G. Gros , Rosa Erra-Balsells*
DOI: 10.1039/B204452H
关键词: Ethanol 、 Pyridine 、 Diene 、 Stereoselectivity 、 Medicinal chemistry 、 Moiety 、 Rose bengal 、 Singlet oxygen 、 Ether 、 Organic chemistry 、 Chemistry
摘要: The reaction of ergosterol (ERGO) with singlet oxygen in vitro was studied by using different combinations the photosensitizers (i.e. rose Bengal and eosine) solvents pyridine, ethanol methyl tert-butyl ether) all products obtained were isolated fully characterized (mp, Rf, UV, 1H-NMR, 13C-NMR, EI-MS, ESI-MS HR-MS). In together expected (22E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol, EEP, keto derivative (22E)-3β-hydroxyergosta-5,8(9),22-trien-7-one, KE, obtained. EEP (22E)-5α,8α-epidioxyergosta-6,9,22-trien-3β-ol, EEP9(11), (22E)-ergosta-6,9,22-triene-3β,5α,8α-triol, DHOE, as main (22E)-ergosta-5,7,9,22-tetraen-3β-ol, DHE, trace amounts. ether, a complex mixture (22E)-7α-hydroperoxyergosta-5,8(9),22-trien-3β-ol, EHP, (22E)-ergosta-5,8(9),22-triene-3β,7α-diol, EH, minor showed strong dependence on medium. regioselective stereoselective character attack ERGO diene moiety is discussed terms HOMO's properties.
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sci-hub.se 参考文章(15)
Till Böcking, Kevin D. Barrow, Andrew G. Netting, Terry C. Chilcott, Hans G. L. Coster, Milan Höfer, Effects of singlet oxygen on membrane sterols in the yeast Saccharomyces cerevisiae European Journal of Biochemistry. ,vol. 267, pp. 1607- 1618 ,(2000) , 10.1046/J.1432-1327.2000.01179.X
Phillip W. Albro, Jean T. Corbett, Joanna L. Schroeder, DOUBLY ALLYLIC HYDROPEROXIDE FORMED IN THE REACTION BETWEEN STEROL 5,7‐DIENES AND SINGLET OXYGEN Photochemistry and Photobiology. ,vol. 60, pp. 310- 315 ,(1994) , 10.1111/J.1751-1097.1994.TB05109.X
Michael H. Fisch, Robert Ernst, Brigitta H. Flick, Joseph Arditti, Derek H. R. Barton, Philip D. Magnus, Ian D. Menzies, Identity of ergosterol ‘5β,8β-peroxide’ J. Chem. Soc., Chem. Commun.. ,vol. 0, pp. 530- 530 ,(1973) , 10.1039/C39730000530
A. A. Leslie Gunatilaka, Yalamanchili Gopichand, Francis J. Schmitz, Carl Djerassi, Minor and trace sterols in marine invertebrates. 26. Isolation and structure elucidation of nine new 5.alpha.,8.alpha.-epidoxy sterols from four marine organisms Journal of Organic Chemistry. ,vol. 46, pp. 3860- 3866 ,(1981) , 10.1021/JO00332A020
Younus M. Sheikh, Carl Djerassi, Steroids from sponges Tetrahedron. ,vol. 30, pp. 4095- 4103 ,(1974) , 10.1016/S0040-4020(01)97391-0
Joanna Diak, INVESTIGATION ON SOME COMPOUNDS BIOSYNTHESIZED BY FRUITBODIES OF NAEMATOLOMA FASCICULARE/HUDS. EX FR./P. KARST Planta Medica. ,vol. 32, pp. 181- 187 ,(1977) , 10.1055/S-0028-1097581
John Olmsted, Photocalorimetric studies of singlet oxygen reactions Journal of the American Chemical Society. ,vol. 102, pp. 66- 71 ,(1980) , 10.1021/JA00521A012
Kirsti Kahlos, L. Kangas, R. Hiltunen, Ergosterol peroxide, an active compound from Inonotus radiatus Planta Medica. ,vol. 55, pp. 389- 390 ,(1989) , 10.1055/S-2006-962036
Carlos Jiménez, Emilio Quiñoa, Ricardo Riguera, Ramón Vilalta, Josi María Quintela, The dietary origin of epidioxysteroids in actinia equina. A carbon-14 incorporation experiment Journal of Natural Products. ,vol. 52, pp. 619- 622 ,(1989) , 10.1021/NP50063A023
William G. Dauben, Gerhard J. Fonken, The Structure of Photoisopyrocalciferol and Photopyrocalciferol1-3 Journal of the American Chemical Society. ,vol. 81, pp. 4060- 4068 ,(1959) , 10.1021/JA01524A062