A new look into the reaction between ergosterol and singlet oxygen in vitro

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,...

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Autores principales:	Ponce, María Alejandra, Ramirez, Javier Alberto, Gros, Eduardo Gervasio, Erra Balsells, Rosa
Publicado:	2002
Materias:	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
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v1_n10_p749_Ponce http://hdl.handle.net/20.500.12110/paper_1474905X_v1_n10_p749_Ponce
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_1474905X_v1_n10_p749_Ponce
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spelling	paper:paper_1474905X_v1_n10_p749_Ponce2023-06-08T16:17:43Z A new look into the reaction between ergosterol and singlet oxygen in vitro Ponce, María Alejandra Ramirez, Javier Alberto Gros, Eduardo Gervasio Erra Balsells, Rosa 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 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. Fil:Ponce, M.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ramirez, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Gros, E.G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Erra-Balsells, R. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2002 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v1_n10_p749_Ponce http://hdl.handle.net/20.500.12110/paper_1474905X_v1_n10_p749_Ponce
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	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
spellingShingle	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 Ponce, María Alejandra Ramirez, Javier Alberto Gros, Eduardo Gervasio Erra Balsells, Rosa A new look into the reaction between ergosterol and singlet oxygen in vitro
topic_facet	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
description	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.
author	Ponce, María Alejandra Ramirez, Javier Alberto Gros, Eduardo Gervasio Erra Balsells, Rosa
author_facet	Ponce, María Alejandra Ramirez, Javier Alberto Gros, Eduardo Gervasio Erra Balsells, Rosa
author_sort	Ponce, María Alejandra
title	A new look into the reaction between ergosterol and singlet oxygen in vitro
title_short	A new look into the reaction between ergosterol and singlet oxygen in vitro
title_full	A new look into the reaction between ergosterol and singlet oxygen in vitro
title_fullStr	A new look into the reaction between ergosterol and singlet oxygen in vitro
title_full_unstemmed	A new look into the reaction between ergosterol and singlet oxygen in vitro
title_sort	new look into the reaction between ergosterol and singlet oxygen in vitro
publishDate	2002
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v1_n10_p749_Ponce http://hdl.handle.net/20.500.12110/paper_1474905X_v1_n10_p749_Ponce
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A new look into the reaction between ergosterol and singlet oxygen in vitro

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