Next Article in Journal
Rheumatoid Arthritis: The Stride from Research to Clinical Practice
Next Article in Special Issue
A Review of the Latest Advances in Encrypted Bioactive Peptides from Protein-Rich Waste
Previous Article in Journal
Development of an in Silico Model of DPPH• Free Radical Scavenging Capacity: Prediction of Antioxidant Activity of Coumarin Type Compounds
Previous Article in Special Issue
Home-Processed Red Beetroot (Beta vulgaris L.) Products: Changes in Antioxidant Properties and Bioaccessibility
Article Menu
Issue 6 (June) cover image

Export Article

Open AccessArticle
Int. J. Mol. Sci. 2016, 17(6), 899; doi:10.3390/ijms17060899

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
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)
View Full-Text   |   Download PDF [551 KB, uploaded 7 June 2016]   |  

Abstract

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
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Int. J. Mol. Sci. EISSN 1422-0067 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top