HSCCC Separations of Rutin Esters Obtained by Enzymatic Reaction Catalyzed by Lipase
The flavonoid rutin presents several pharmacological effects, despite this, its application in the pharmaceutical industry can be significantly limited by its low bioavailability. The development of lipophilic derivatives by esterification of hydroxyl groups with fatty acid chains may be an effectiv...
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Sociedade Brasileira de Química
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ftjscielo:oai:scielo:S0103-50532021000300523 2023-05-15T13:41:51+02:00 HSCCC Separations of Rutin Esters Obtained by Enzymatic Reaction Catalyzed by Lipase Couto,Jéssyca F. O. Simas,Daniel L. R. Silva,Marcos V. T. e Barth,Thiago Pinto,Shaft C. Tinoco,Luzineide W. Freire,Denise M. G. Muzitano,Michelle F. Leal,Ivana C. R. 2021-03-01 text/html http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000300523 en eng Sociedade Brasileira de Química 10.21577/0103-5053.20200206 info:eu-repo/semantics/openAccess Journal of the Brazilian Chemical Society v.32 n.3 2021 countercurrent chromatography esterification reaction fatty acids Novozyme rutin esters info:eu-repo/semantics/article 2021 ftjscielo 2021-03-11T11:28:17Z The flavonoid rutin presents several pharmacological effects, despite this, its application in the pharmaceutical industry can be significantly limited by its low bioavailability. The development of lipophilic derivatives by esterification of hydroxyl groups with fatty acid chains may be an effective strategy to change their physicochemical properties. This work aims to use high-speed countercurrent chromatography (HSCCC) to isolate rutin esters produced by esterification reactions catalyzed by the immobilized lipase from Candida antarctica (Novozyme 435®). The lipase-catalyzed synthesis of rutin esters (R3-R18:2) in 2-methyl-2-butanol exhibited conversions that ranged from 16 to 40% and highest conversion for short chain fatty acids (R4-R12). After initial partitioning tests of the reaction mixture in different solvent proportions followed by thin layer chromatography (TLC) analysis, the biphasic solvent systems consisting in HEMWat (hexane/ethyl acetate/methanol/water) in different proportions were chosen to separate rutin esters. These esters were separated for the first time to the reaction mixture via HSCCC. This technique proved to be more advantageous than the traditionally one since it allowed quick isolation and high purity (≥ 90%) of the products. It also permitted a substrate recovery for reuse in other enzymatic reactions. Furthermore, the results add valuable information, specially concerning the structures elucidation of different rutin esters not previously described. Article in Journal/Newspaper Antarc* Antarctica SciELO Brazil (Scientific Electronic Library Online) |
institution |
Open Polar |
collection |
SciELO Brazil (Scientific Electronic Library Online) |
op_collection_id |
ftjscielo |
language |
English |
topic |
countercurrent chromatography esterification reaction fatty acids Novozyme rutin esters |
spellingShingle |
countercurrent chromatography esterification reaction fatty acids Novozyme rutin esters Couto,Jéssyca F. O. Simas,Daniel L. R. Silva,Marcos V. T. e Barth,Thiago Pinto,Shaft C. Tinoco,Luzineide W. Freire,Denise M. G. Muzitano,Michelle F. Leal,Ivana C. R. HSCCC Separations of Rutin Esters Obtained by Enzymatic Reaction Catalyzed by Lipase |
topic_facet |
countercurrent chromatography esterification reaction fatty acids Novozyme rutin esters |
description |
The flavonoid rutin presents several pharmacological effects, despite this, its application in the pharmaceutical industry can be significantly limited by its low bioavailability. The development of lipophilic derivatives by esterification of hydroxyl groups with fatty acid chains may be an effective strategy to change their physicochemical properties. This work aims to use high-speed countercurrent chromatography (HSCCC) to isolate rutin esters produced by esterification reactions catalyzed by the immobilized lipase from Candida antarctica (Novozyme 435®). The lipase-catalyzed synthesis of rutin esters (R3-R18:2) in 2-methyl-2-butanol exhibited conversions that ranged from 16 to 40% and highest conversion for short chain fatty acids (R4-R12). After initial partitioning tests of the reaction mixture in different solvent proportions followed by thin layer chromatography (TLC) analysis, the biphasic solvent systems consisting in HEMWat (hexane/ethyl acetate/methanol/water) in different proportions were chosen to separate rutin esters. These esters were separated for the first time to the reaction mixture via HSCCC. This technique proved to be more advantageous than the traditionally one since it allowed quick isolation and high purity (≥ 90%) of the products. It also permitted a substrate recovery for reuse in other enzymatic reactions. Furthermore, the results add valuable information, specially concerning the structures elucidation of different rutin esters not previously described. |
format |
Article in Journal/Newspaper |
author |
Couto,Jéssyca F. O. Simas,Daniel L. R. Silva,Marcos V. T. e Barth,Thiago Pinto,Shaft C. Tinoco,Luzineide W. Freire,Denise M. G. Muzitano,Michelle F. Leal,Ivana C. R. |
author_facet |
Couto,Jéssyca F. O. Simas,Daniel L. R. Silva,Marcos V. T. e Barth,Thiago Pinto,Shaft C. Tinoco,Luzineide W. Freire,Denise M. G. Muzitano,Michelle F. Leal,Ivana C. R. |
author_sort |
Couto,Jéssyca F. O. |
title |
HSCCC Separations of Rutin Esters Obtained by Enzymatic Reaction Catalyzed by Lipase |
title_short |
HSCCC Separations of Rutin Esters Obtained by Enzymatic Reaction Catalyzed by Lipase |
title_full |
HSCCC Separations of Rutin Esters Obtained by Enzymatic Reaction Catalyzed by Lipase |
title_fullStr |
HSCCC Separations of Rutin Esters Obtained by Enzymatic Reaction Catalyzed by Lipase |
title_full_unstemmed |
HSCCC Separations of Rutin Esters Obtained by Enzymatic Reaction Catalyzed by Lipase |
title_sort |
hsccc separations of rutin esters obtained by enzymatic reaction catalyzed by lipase |
publisher |
Sociedade Brasileira de Química |
publishDate |
2021 |
url |
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000300523 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Journal of the Brazilian Chemical Society v.32 n.3 2021 |
op_relation |
10.21577/0103-5053.20200206 |
op_rights |
info:eu-repo/semantics/openAccess |
_version_ |
1766159141572706304 |