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Article

Isoquercitrin Esters with Mono- or Dicarboxylic Acids: Enzymatic Preparation and Properties

1
Laboratory of Biotransformation, Institute of Microbiology, Czech Academy of Sciences, Vídeňská 1083, CZ-142 20 Prague, Czech Republic
2
Institute of Chemistry, University of Rostock, Albert-Einstein-Str. 3a, GE-18059 Rostock, Germany
*
Author to whom correspondence should be addressed.
Academic Editor: Maurizio Battino
Int. J. Mol. Sci. 2016, 17(6), 899; https://doi.org/10.3390/ijms17060899
Received: 14 April 2016 / Revised: 25 May 2016 / Accepted: 30 May 2016 / Published: 7 June 2016
(This article belongs to the Special Issue Macro- and Micro-nutrient Antioxidants)
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. View Full-Text
Keywords: isoquercitrin; quercetin; fatty acid; antioxidant activity; log P; Novozym 435; lipase; DPPH; lipoperoxidation isoquercitrin; quercetin; fatty acid; antioxidant activity; log P; Novozym 435; lipase; DPPH; lipoperoxidation
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MDPI and ACS Style

Vavříková, E.; Langschwager, F.; Jezova-Kalachova, L.; Křenková, A.; Mikulová, B.; Kuzma, M.; Křen, V.; Valentová, K. Isoquercitrin Esters with Mono- or Dicarboxylic Acids: Enzymatic Preparation and Properties. Int. J. Mol. Sci. 2016, 17, 899. https://doi.org/10.3390/ijms17060899

AMA Style

Vavříková E, Langschwager F, Jezova-Kalachova L, Křenková A, Mikulová B, Kuzma M, Křen V, Valentová K. Isoquercitrin Esters with Mono- or Dicarboxylic Acids: Enzymatic Preparation and Properties. International Journal of Molecular Sciences. 2016; 17(6):899. https://doi.org/10.3390/ijms17060899

Chicago/Turabian Style

Vavříková, Eva, Fanny Langschwager, Lubica Jezova-Kalachova, Alena Křenková, Barbora Mikulová, Marek Kuzma, Vladimír Křen, and Kateřina Valentová. 2016. "Isoquercitrin Esters with Mono- or Dicarboxylic Acids: Enzymatic Preparation and Properties" International Journal of Molecular Sciences 17, no. 6: 899. https://doi.org/10.3390/ijms17060899

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