Artículo
Ponce, M.A.; Ramirez, J.A.; Galagovsky, L.R.; Gros, E.G.; Erra-Balsells, R. "A new look into the reaction between ergosterol and singlet oxygen in vitro" (2002) Photochemical and Photobiological Sciences. 1(10):749-756
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Abstract:
The reaction of ergosterol (ERGO) with singlet oxygen in vitro was studied by using different combinations of the photosensitizers (i.e. rose Bengal and eosine) and solvents (i.e. pyridine, ethanol and methyl tert-butyl ether) and all the products obtained were isolated and fully characterized (mp, Rf, UV, 1H-NMR, 13C-NMR, EI-MS, ESI-MS and HR-MS). In pyridine, together with the expected (22E -5α,8α-epidioxyergosta-6,22-dien-3β-ol, EEP, the keto derivative (22E)-3β-hydroxyergosta-5,8(9),22-trien-7-one, KE, was obtained. In ethanol the expected EEP was obtained together with (22E -5α,8α-epidioxyergosta-6,9,22-trien-3β-ol, EEP9(11), and (22E)-ergosta-6,9,22-triene-3β,5α,8α-triol, DHOE, as main products and (22E)-ergosta-5,7,9,22-tetraen-3β-ol, DHE, in trace amounts. In methyl tert-butyl ether, a complex mixture of EEP, KE, DHOE, EEP9(11), DHE, together with (22E -7α-hydroperoxy-ergosta-5,8(9),22-trien-3β-ol, EHP, and (22E -ergosta-5,8(9),22-triene-3β,7α-diol, EH, was obtained. The minor products were characterized and showed strong dependence on the reaction medium. The regioselective and stereoselective character of the singlet oxygen attack on the ERGO diene moiety is discussed in terms of ERGO HOMO's properties.
Registro:
| Documento: | Artículo |
| Título: | A new look into the reaction between ergosterol and singlet oxygen in vitro |
| Autor: | Ponce, M.A.; Ramirez, J.A.; Galagovsky, L.R.; Gros, E.G.; Erra-Balsells, R. |
| Filiación: | UMYMFOR, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II 3, 1428 Buenos Aires, Argentina Laboratorio de Fotoquimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II 3, 1428 Buenos Aires, Argentina Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II 3, 1428 Buenos Aires, Argentina |
| Palabras clave: | alcohol; carbon 13; eosin; ergosterol; photosensitizing agent; proton; pyridine; rose bengal; singlet oxygen; solvent; tert butyl methyl ether; article; carbon nuclear magnetic resonance; chemical analysis; chemical reaction; chemical structure; controlled study; in vitro study; isolation procedure; mass spectrometry; priority journal; proton nuclear magnetic resonance; stereochemistry; chemistry; light; radiation exposure; Eosine Yellowish-(YS); Ergosterol; Light; Models, Molecular; Molecular Structure; Photosensitizing Agents; Rose Bengal; Singlet Oxygen; Solvents |
| Año: | 2002 |
| Volumen: | 1 |
| Número: | 10 |
| Página de inicio: | 749 |
| Página de fin: | 756 |
| DOI: | http://dx.doi.org/10.1039/b204452h |
| Título revista: | Photochemical and Photobiological Sciences |
| Título revista abreviado: | Photochem. Photobiol. Sci. |
| ISSN: | 1474905X |
| CODEN: | PPSHC |
| CAS: | alcohol, 64-17-5; carbon 13, 14762-74-4; eosin, 17372-87-1, 51395-88-1, 548-26-5; ergosterol, 23637-22-1, 2418-45-3, 3992-98-1, 57-87-4; proton, 12408-02-5, 12586-59-3; pyridine, 110-86-1; rose bengal, 11121-48-5, 11139-83-6, 632-68-8; tert butyl methyl ether, 1634-04-4; Eosine Yellowish-(YS), 17372-87-1; Ergosterol, 57-87-4; Photosensitizing Agents; Rose Bengal, 11121-48-5; Singlet Oxygen, 17778-80-2; Solvents |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v1_n10_p749_Ponce |
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Citas:
---------- APA ----------
Ponce, M.A., Ramirez, J.A., Galagovsky, L.R., Gros, E.G. & Erra-Balsells, R. (2002) . A new look into the reaction between ergosterol and singlet oxygen in vitro. Photochemical and Photobiological Sciences, 1(10), 749-756.http://dx.doi.org/10.1039/b204452h
---------- CHICAGO ----------
Ponce, M.A., Ramirez, J.A., Galagovsky, L.R., Gros, E.G., Erra-Balsells, R. "A new look into the reaction between ergosterol and singlet oxygen in vitro" . Photochemical and Photobiological Sciences 1, no. 10 (2002) : 749-756.http://dx.doi.org/10.1039/b204452h
---------- MLA ----------
Ponce, M.A., Ramirez, J.A., Galagovsky, L.R., Gros, E.G., Erra-Balsells, R. "A new look into the reaction between ergosterol and singlet oxygen in vitro" . Photochemical and Photobiological Sciences, vol. 1, no. 10, 2002, pp. 749-756.http://dx.doi.org/10.1039/b204452h
---------- VANCOUVER ----------
Ponce, M.A., Ramirez, J.A., Galagovsky, L.R., Gros, E.G., Erra-Balsells, R. A new look into the reaction between ergosterol and singlet oxygen in vitro. Photochem. Photobiol. Sci. 2002;1(10):749-756.http://dx.doi.org/10.1039/b204452h
