Isoquercitrin Esters with Mono- or Dicarboxylic Acids: Enzymatic Preparation and Properties
A series of isoquercitrin (quercetin-3-O-β-d-glucopyranoside) esters with mono- or dicarboxylic acids was designed to modulate hydro- and lipophilicity and biological properties. Esterification of isoquercitrin was accomplished by direct chemoenzymatic reaction using Novozym 435 (lipase from Candida...
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ftpubmed:oai:pubmedcentral.nih.gov:4926433 2023-05-15T13:51:09+02:00 Isoquercitrin Esters with Mono- or Dicarboxylic Acids: Enzymatic Preparation and Properties Vavříková, Eva Langschwager, Fanny Jezova-Kalachova, Lubica Křenková, Alena Mikulová, Barbora Kuzma, Marek Křen, Vladimír Valentová, Kateřina 2016-06-07 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4926433/ http://www.ncbi.nlm.nih.gov/pubmed/27338349 https://doi.org/10.3390/ijms17060899 en eng MDPI http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4926433/ http://www.ncbi.nlm.nih.gov/pubmed/27338349 http://dx.doi.org/10.3390/ijms17060899 © 2016 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/). CC-BY Article Text 2016 ftpubmed https://doi.org/10.3390/ijms17060899 2016-07-10T00:13:31Z A series of isoquercitrin (quercetin-3-O-β-d-glucopyranoside) esters with mono- or dicarboxylic acids was designed to modulate hydro- and lipophilicity and biological properties. Esterification of isoquercitrin was accomplished by direct chemoenzymatic reaction using Novozym 435 (lipase from Candida antarctica), which accepted C5- to C12-dicarboxylic acids; the shorter ones, such as oxalic (C2), malonic (C3), succinic (C4) and maleic (C4) acids were not substrates of the lipase. Lipophilicity of monocarboxylic acid derivatives, measured as log P, increased with the chain length. Esters with glutaric and adipic acids exhibited hydrophilicity, and the dodecanedioic acid hemiester was more lipophilic. All derivatives were less able to reduce Folin–Ciocalteau reagent (FCR) and scavenge DPPH (1,1-diphenyl-2-picrylhydrazyl) than isoquercitrin; ABTS (2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid)) radical-scavenging activity was comparable. Dodecanoate and palmitate were the least active in FCR and ABTS scavenging; dodecanoate and hemiglutarate were the strongest DPPH scavengers. In contrast, most derivatives were much better inhibitors of microsomal lipoperoxidation than isoquercitrin; butyrate and hexanoate were the most efficient. Anti-lipoperoxidant activity of monocarboxylic derivatives, except acetates, decreased with increasing aliphatic chain. The opposite trend was noted for dicarboxylic acid hemiesters, isoquercitrin hemidodecanedioate being the most active. Overall, IQ butyrate, hexanoate and hemidodecanedioate are the most promising candidates for further studies. Text Antarc* Antarctica PubMed Central (PMC) International Journal of Molecular Sciences 17 6 899 |
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Article Vavříková, Eva Langschwager, Fanny Jezova-Kalachova, Lubica Křenková, Alena Mikulová, Barbora Kuzma, Marek Křen, Vladimír Valentová, Kateřina Isoquercitrin Esters with Mono- or Dicarboxylic Acids: Enzymatic Preparation and Properties |
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Article |
description |
A series of isoquercitrin (quercetin-3-O-β-d-glucopyranoside) esters with mono- or dicarboxylic acids was designed to modulate hydro- and lipophilicity and biological properties. Esterification of isoquercitrin was accomplished by direct chemoenzymatic reaction using Novozym 435 (lipase from Candida antarctica), which accepted C5- to C12-dicarboxylic acids; the shorter ones, such as oxalic (C2), malonic (C3), succinic (C4) and maleic (C4) acids were not substrates of the lipase. Lipophilicity of monocarboxylic acid derivatives, measured as log P, increased with the chain length. Esters with glutaric and adipic acids exhibited hydrophilicity, and the dodecanedioic acid hemiester was more lipophilic. All derivatives were less able to reduce Folin–Ciocalteau reagent (FCR) and scavenge DPPH (1,1-diphenyl-2-picrylhydrazyl) than isoquercitrin; ABTS (2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid)) radical-scavenging activity was comparable. Dodecanoate and palmitate were the least active in FCR and ABTS scavenging; dodecanoate and hemiglutarate were the strongest DPPH scavengers. In contrast, most derivatives were much better inhibitors of microsomal lipoperoxidation than isoquercitrin; butyrate and hexanoate were the most efficient. Anti-lipoperoxidant activity of monocarboxylic derivatives, except acetates, decreased with increasing aliphatic chain. The opposite trend was noted for dicarboxylic acid hemiesters, isoquercitrin hemidodecanedioate being the most active. Overall, IQ butyrate, hexanoate and hemidodecanedioate are the most promising candidates for further studies. |
format |
Text |
author |
Vavříková, Eva Langschwager, Fanny Jezova-Kalachova, Lubica Křenková, Alena Mikulová, Barbora Kuzma, Marek Křen, Vladimír Valentová, Kateřina |
author_facet |
Vavříková, Eva Langschwager, Fanny Jezova-Kalachova, Lubica Křenková, Alena Mikulová, Barbora Kuzma, Marek Křen, Vladimír Valentová, Kateřina |
author_sort |
Vavříková, Eva |
title |
Isoquercitrin Esters with Mono- or Dicarboxylic Acids: Enzymatic Preparation and Properties |
title_short |
Isoquercitrin Esters with Mono- or Dicarboxylic Acids: Enzymatic Preparation and Properties |
title_full |
Isoquercitrin Esters with Mono- or Dicarboxylic Acids: Enzymatic Preparation and Properties |
title_fullStr |
Isoquercitrin Esters with Mono- or Dicarboxylic Acids: Enzymatic Preparation and Properties |
title_full_unstemmed |
Isoquercitrin Esters with Mono- or Dicarboxylic Acids: Enzymatic Preparation and Properties |
title_sort |
isoquercitrin esters with mono- or dicarboxylic acids: enzymatic preparation and properties |
publisher |
MDPI |
publishDate |
2016 |
url |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4926433/ http://www.ncbi.nlm.nih.gov/pubmed/27338349 https://doi.org/10.3390/ijms17060899 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4926433/ http://www.ncbi.nlm.nih.gov/pubmed/27338349 http://dx.doi.org/10.3390/ijms17060899 |
op_rights |
© 2016 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/). |
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CC-BY |
op_doi |
https://doi.org/10.3390/ijms17060899 |
container_title |
International Journal of Molecular Sciences |
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17 |
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6 |
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899 |
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1766254764777013248 |