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,...
Guardado en:
| Autores principales: | , , , , |
|---|---|
| Formato: | JOUR |
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_1474905X_v1_n10_p749_Ponce |
| Aporte de: |
| id |
todo:paper_1474905X_v1_n10_p749_Ponce |
|---|---|
| record_format |
dspace |
| spelling |
todo:paper_1474905X_v1_n10_p749_Ponce2023-10-03T16:18:22Z A new look into the reaction between ergosterol and singlet oxygen in vitro Ponce, M.A. Ramirez, J.A. Galagovsky, L.R. Gros, E.G. Erra-Balsells, R. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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, 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 |
| 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. |
| format |
JOUR |
| author |
Ponce, M.A. Ramirez, J.A. Galagovsky, L.R. Gros, E.G. Erra-Balsells, R. |
| author_facet |
Ponce, M.A. Ramirez, J.A. Galagovsky, L.R. Gros, E.G. Erra-Balsells, R. |
| author_sort |
Ponce, M.A. |
| 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 |
| url |
http://hdl.handle.net/20.500.12110/paper_1474905X_v1_n10_p749_Ponce |
| work_keys_str_mv |
AT poncema anewlookintothereactionbetweenergosterolandsingletoxygeninvitro AT ramirezja anewlookintothereactionbetweenergosterolandsingletoxygeninvitro AT galagovskylr anewlookintothereactionbetweenergosterolandsingletoxygeninvitro AT groseg anewlookintothereactionbetweenergosterolandsingletoxygeninvitro AT errabalsellsr anewlookintothereactionbetweenergosterolandsingletoxygeninvitro AT poncema newlookintothereactionbetweenergosterolandsingletoxygeninvitro AT ramirezja newlookintothereactionbetweenergosterolandsingletoxygeninvitro AT galagovskylr newlookintothereactionbetweenergosterolandsingletoxygeninvitro AT groseg newlookintothereactionbetweenergosterolandsingletoxygeninvitro AT errabalsellsr newlookintothereactionbetweenergosterolandsingletoxygeninvitro |
| _version_ |
1807316224729677824 |