Synthesis, Molecular Characterization and Preliminary Antioxidant Activity Evaluation of Quercetin Fatty Esters
Abstract Quercetin shows interesting pharmacological effects, but its use in topical applications is limited by its low skin permeability and solubility. In this work, the synthesis of highly lipophilic quercetin esters with oleic, linoleic and linolenic acid useful as topical quercetin prodrugs is...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Mainini, Francesca [verfasserIn] |
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| Format: |
Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2013 |
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| Schlagwörter: |
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| Anmerkung: |
© AOCS 2013 |
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| Übergeordnetes Werk: |
Enthalten in: Journal of the American Oil Chemists' Society - Springer Berlin Heidelberg, 1947, 90(2013), 11 vom: 06. Sept., Seite 1751-1759 |
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| Übergeordnetes Werk: |
volume:90 ; year:2013 ; number:11 ; day:06 ; month:09 ; pages:1751-1759 |
| Links: |
|---|
| DOI / URN: |
10.1007/s11746-013-2314-0 |
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OLC2068160536 |
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| 520 | |a Abstract Quercetin shows interesting pharmacological effects, but its use in topical applications is limited by its low skin permeability and solubility. In this work, the synthesis of highly lipophilic quercetin esters with oleic, linoleic and linolenic acid useful as topical quercetin prodrugs is reported. Partial OH esterification is advisable to maintain the antioxidant activity of these compounds; tetraesters and triesters can be achieved by modulating the reaction conditions utilized for the total esterification of quercetin. The chemical structures of the esters were proven by spectroscopic techniques; quantum chemical NMR calculation were mandatory to unequivocally assign the free position in triesters. Finally, the antioxidant activity of all the synthesized compounds was determined by the 2,2-diphenyl-1-picryl-hydrazyl method and by 2,2-azinobis(3-ethyl-benzothiazoline-6-sulfonic acid) assay. | ||
| 650 | 4 | |a Quercetin pentaesters | |
| 650 | 4 | |a Quercetin tetraesters | |
| 650 | 4 | |a Quercetin trimesters | |
| 650 | 4 | |a Fatty acids | |
| 650 | 4 | |a Bi-dimensional NMR techniques | |
| 650 | 4 | |a Quantum chemical NMR calculation | |
| 650 | 4 | |a DPPH | |
| 650 | 4 | |a ABTS | |
| 700 | 1 | |a Contini, Alessandro |4 aut | |
| 700 | 1 | |a Nava, Donatella |4 aut | |
| 700 | 1 | |a Corsetto, Paola Antonia |4 aut | |
| 700 | 1 | |a Rizzo, Angela Maria |4 aut | |
| 700 | 1 | |a Agradi, Elisabetta |4 aut | |
| 700 | 1 | |a Pini, Elena |4 aut | |
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10.1007/s11746-013-2314-0 doi (DE-627)OLC2068160536 (DE-He213)s11746-013-2314-0-p DE-627 ger DE-627 rakwb eng 660 VZ Mainini, Francesca verfasserin aut Synthesis, Molecular Characterization and Preliminary Antioxidant Activity Evaluation of Quercetin Fatty Esters 2013 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © AOCS 2013 Abstract Quercetin shows interesting pharmacological effects, but its use in topical applications is limited by its low skin permeability and solubility. In this work, the synthesis of highly lipophilic quercetin esters with oleic, linoleic and linolenic acid useful as topical quercetin prodrugs is reported. Partial OH esterification is advisable to maintain the antioxidant activity of these compounds; tetraesters and triesters can be achieved by modulating the reaction conditions utilized for the total esterification of quercetin. The chemical structures of the esters were proven by spectroscopic techniques; quantum chemical NMR calculation were mandatory to unequivocally assign the free position in triesters. Finally, the antioxidant activity of all the synthesized compounds was determined by the 2,2-diphenyl-1-picryl-hydrazyl method and by 2,2-azinobis(3-ethyl-benzothiazoline-6-sulfonic acid) assay. Quercetin pentaesters Quercetin tetraesters Quercetin trimesters Fatty acids Bi-dimensional NMR techniques Quantum chemical NMR calculation DPPH ABTS Contini, Alessandro aut Nava, Donatella aut Corsetto, Paola Antonia aut Rizzo, Angela Maria aut Agradi, Elisabetta aut Pini, Elena aut Enthalten in Journal of the American Oil Chemists' Society Springer Berlin Heidelberg, 1947 90(2013), 11 vom: 06. Sept., Seite 1751-1759 (DE-627)129595691 (DE-600)240684-6 (DE-576)015088715 0003-021X nnns volume:90 year:2013 number:11 day:06 month:09 pages:1751-1759 https://doi.org/10.1007/s11746-013-2314-0 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_70 GBV_ILN_183 GBV_ILN_2018 GBV_ILN_4012 GBV_ILN_4219 AR 90 2013 11 06 09 1751-1759 |
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10.1007/s11746-013-2314-0 doi (DE-627)OLC2068160536 (DE-He213)s11746-013-2314-0-p DE-627 ger DE-627 rakwb eng 660 VZ Mainini, Francesca verfasserin aut Synthesis, Molecular Characterization and Preliminary Antioxidant Activity Evaluation of Quercetin Fatty Esters 2013 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © AOCS 2013 Abstract Quercetin shows interesting pharmacological effects, but its use in topical applications is limited by its low skin permeability and solubility. In this work, the synthesis of highly lipophilic quercetin esters with oleic, linoleic and linolenic acid useful as topical quercetin prodrugs is reported. Partial OH esterification is advisable to maintain the antioxidant activity of these compounds; tetraesters and triesters can be achieved by modulating the reaction conditions utilized for the total esterification of quercetin. The chemical structures of the esters were proven by spectroscopic techniques; quantum chemical NMR calculation were mandatory to unequivocally assign the free position in triesters. Finally, the antioxidant activity of all the synthesized compounds was determined by the 2,2-diphenyl-1-picryl-hydrazyl method and by 2,2-azinobis(3-ethyl-benzothiazoline-6-sulfonic acid) assay. Quercetin pentaesters Quercetin tetraesters Quercetin trimesters Fatty acids Bi-dimensional NMR techniques Quantum chemical NMR calculation DPPH ABTS Contini, Alessandro aut Nava, Donatella aut Corsetto, Paola Antonia aut Rizzo, Angela Maria aut Agradi, Elisabetta aut Pini, Elena aut Enthalten in Journal of the American Oil Chemists' Society Springer Berlin Heidelberg, 1947 90(2013), 11 vom: 06. Sept., Seite 1751-1759 (DE-627)129595691 (DE-600)240684-6 (DE-576)015088715 0003-021X nnns volume:90 year:2013 number:11 day:06 month:09 pages:1751-1759 https://doi.org/10.1007/s11746-013-2314-0 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_70 GBV_ILN_183 GBV_ILN_2018 GBV_ILN_4012 GBV_ILN_4219 AR 90 2013 11 06 09 1751-1759 |
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10.1007/s11746-013-2314-0 doi (DE-627)OLC2068160536 (DE-He213)s11746-013-2314-0-p DE-627 ger DE-627 rakwb eng 660 VZ Mainini, Francesca verfasserin aut Synthesis, Molecular Characterization and Preliminary Antioxidant Activity Evaluation of Quercetin Fatty Esters 2013 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © AOCS 2013 Abstract Quercetin shows interesting pharmacological effects, but its use in topical applications is limited by its low skin permeability and solubility. In this work, the synthesis of highly lipophilic quercetin esters with oleic, linoleic and linolenic acid useful as topical quercetin prodrugs is reported. Partial OH esterification is advisable to maintain the antioxidant activity of these compounds; tetraesters and triesters can be achieved by modulating the reaction conditions utilized for the total esterification of quercetin. The chemical structures of the esters were proven by spectroscopic techniques; quantum chemical NMR calculation were mandatory to unequivocally assign the free position in triesters. Finally, the antioxidant activity of all the synthesized compounds was determined by the 2,2-diphenyl-1-picryl-hydrazyl method and by 2,2-azinobis(3-ethyl-benzothiazoline-6-sulfonic acid) assay. Quercetin pentaesters Quercetin tetraesters Quercetin trimesters Fatty acids Bi-dimensional NMR techniques Quantum chemical NMR calculation DPPH ABTS Contini, Alessandro aut Nava, Donatella aut Corsetto, Paola Antonia aut Rizzo, Angela Maria aut Agradi, Elisabetta aut Pini, Elena aut Enthalten in Journal of the American Oil Chemists' Society Springer Berlin Heidelberg, 1947 90(2013), 11 vom: 06. Sept., Seite 1751-1759 (DE-627)129595691 (DE-600)240684-6 (DE-576)015088715 0003-021X nnns volume:90 year:2013 number:11 day:06 month:09 pages:1751-1759 https://doi.org/10.1007/s11746-013-2314-0 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_70 GBV_ILN_183 GBV_ILN_2018 GBV_ILN_4012 GBV_ILN_4219 AR 90 2013 11 06 09 1751-1759 |
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10.1007/s11746-013-2314-0 doi (DE-627)OLC2068160536 (DE-He213)s11746-013-2314-0-p DE-627 ger DE-627 rakwb eng 660 VZ Mainini, Francesca verfasserin aut Synthesis, Molecular Characterization and Preliminary Antioxidant Activity Evaluation of Quercetin Fatty Esters 2013 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © AOCS 2013 Abstract Quercetin shows interesting pharmacological effects, but its use in topical applications is limited by its low skin permeability and solubility. In this work, the synthesis of highly lipophilic quercetin esters with oleic, linoleic and linolenic acid useful as topical quercetin prodrugs is reported. Partial OH esterification is advisable to maintain the antioxidant activity of these compounds; tetraesters and triesters can be achieved by modulating the reaction conditions utilized for the total esterification of quercetin. The chemical structures of the esters were proven by spectroscopic techniques; quantum chemical NMR calculation were mandatory to unequivocally assign the free position in triesters. Finally, the antioxidant activity of all the synthesized compounds was determined by the 2,2-diphenyl-1-picryl-hydrazyl method and by 2,2-azinobis(3-ethyl-benzothiazoline-6-sulfonic acid) assay. Quercetin pentaesters Quercetin tetraesters Quercetin trimesters Fatty acids Bi-dimensional NMR techniques Quantum chemical NMR calculation DPPH ABTS Contini, Alessandro aut Nava, Donatella aut Corsetto, Paola Antonia aut Rizzo, Angela Maria aut Agradi, Elisabetta aut Pini, Elena aut Enthalten in Journal of the American Oil Chemists' Society Springer Berlin Heidelberg, 1947 90(2013), 11 vom: 06. Sept., Seite 1751-1759 (DE-627)129595691 (DE-600)240684-6 (DE-576)015088715 0003-021X nnns volume:90 year:2013 number:11 day:06 month:09 pages:1751-1759 https://doi.org/10.1007/s11746-013-2314-0 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_70 GBV_ILN_183 GBV_ILN_2018 GBV_ILN_4012 GBV_ILN_4219 AR 90 2013 11 06 09 1751-1759 |
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10.1007/s11746-013-2314-0 doi (DE-627)OLC2068160536 (DE-He213)s11746-013-2314-0-p DE-627 ger DE-627 rakwb eng 660 VZ Mainini, Francesca verfasserin aut Synthesis, Molecular Characterization and Preliminary Antioxidant Activity Evaluation of Quercetin Fatty Esters 2013 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © AOCS 2013 Abstract Quercetin shows interesting pharmacological effects, but its use in topical applications is limited by its low skin permeability and solubility. In this work, the synthesis of highly lipophilic quercetin esters with oleic, linoleic and linolenic acid useful as topical quercetin prodrugs is reported. Partial OH esterification is advisable to maintain the antioxidant activity of these compounds; tetraesters and triesters can be achieved by modulating the reaction conditions utilized for the total esterification of quercetin. The chemical structures of the esters were proven by spectroscopic techniques; quantum chemical NMR calculation were mandatory to unequivocally assign the free position in triesters. Finally, the antioxidant activity of all the synthesized compounds was determined by the 2,2-diphenyl-1-picryl-hydrazyl method and by 2,2-azinobis(3-ethyl-benzothiazoline-6-sulfonic acid) assay. Quercetin pentaesters Quercetin tetraesters Quercetin trimesters Fatty acids Bi-dimensional NMR techniques Quantum chemical NMR calculation DPPH ABTS Contini, Alessandro aut Nava, Donatella aut Corsetto, Paola Antonia aut Rizzo, Angela Maria aut Agradi, Elisabetta aut Pini, Elena aut Enthalten in Journal of the American Oil Chemists' Society Springer Berlin Heidelberg, 1947 90(2013), 11 vom: 06. Sept., Seite 1751-1759 (DE-627)129595691 (DE-600)240684-6 (DE-576)015088715 0003-021X nnns volume:90 year:2013 number:11 day:06 month:09 pages:1751-1759 https://doi.org/10.1007/s11746-013-2314-0 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_70 GBV_ILN_183 GBV_ILN_2018 GBV_ILN_4012 GBV_ILN_4219 AR 90 2013 11 06 09 1751-1759 |
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Synthesis, Molecular Characterization and Preliminary Antioxidant Activity Evaluation of Quercetin Fatty Esters |
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Synthesis, Molecular Characterization and Preliminary Antioxidant Activity Evaluation of Quercetin Fatty Esters |
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Mainini, Francesca |
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Journal of the American Oil Chemists' Society |
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Mainini, Francesca Contini, Alessandro Nava, Donatella Corsetto, Paola Antonia Rizzo, Angela Maria Agradi, Elisabetta Pini, Elena |
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synthesis, molecular characterization and preliminary antioxidant activity evaluation of quercetin fatty esters |
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Synthesis, Molecular Characterization and Preliminary Antioxidant Activity Evaluation of Quercetin Fatty Esters |
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Abstract Quercetin shows interesting pharmacological effects, but its use in topical applications is limited by its low skin permeability and solubility. In this work, the synthesis of highly lipophilic quercetin esters with oleic, linoleic and linolenic acid useful as topical quercetin prodrugs is reported. Partial OH esterification is advisable to maintain the antioxidant activity of these compounds; tetraesters and triesters can be achieved by modulating the reaction conditions utilized for the total esterification of quercetin. The chemical structures of the esters were proven by spectroscopic techniques; quantum chemical NMR calculation were mandatory to unequivocally assign the free position in triesters. Finally, the antioxidant activity of all the synthesized compounds was determined by the 2,2-diphenyl-1-picryl-hydrazyl method and by 2,2-azinobis(3-ethyl-benzothiazoline-6-sulfonic acid) assay. © AOCS 2013 |
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Abstract Quercetin shows interesting pharmacological effects, but its use in topical applications is limited by its low skin permeability and solubility. In this work, the synthesis of highly lipophilic quercetin esters with oleic, linoleic and linolenic acid useful as topical quercetin prodrugs is reported. Partial OH esterification is advisable to maintain the antioxidant activity of these compounds; tetraesters and triesters can be achieved by modulating the reaction conditions utilized for the total esterification of quercetin. The chemical structures of the esters were proven by spectroscopic techniques; quantum chemical NMR calculation were mandatory to unequivocally assign the free position in triesters. Finally, the antioxidant activity of all the synthesized compounds was determined by the 2,2-diphenyl-1-picryl-hydrazyl method and by 2,2-azinobis(3-ethyl-benzothiazoline-6-sulfonic acid) assay. © AOCS 2013 |
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Abstract Quercetin shows interesting pharmacological effects, but its use in topical applications is limited by its low skin permeability and solubility. In this work, the synthesis of highly lipophilic quercetin esters with oleic, linoleic and linolenic acid useful as topical quercetin prodrugs is reported. Partial OH esterification is advisable to maintain the antioxidant activity of these compounds; tetraesters and triesters can be achieved by modulating the reaction conditions utilized for the total esterification of quercetin. The chemical structures of the esters were proven by spectroscopic techniques; quantum chemical NMR calculation were mandatory to unequivocally assign the free position in triesters. Finally, the antioxidant activity of all the synthesized compounds was determined by the 2,2-diphenyl-1-picryl-hydrazyl method and by 2,2-azinobis(3-ethyl-benzothiazoline-6-sulfonic acid) assay. © AOCS 2013 |
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Synthesis, Molecular Characterization and Preliminary Antioxidant Activity Evaluation of Quercetin Fatty Esters |
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