Natural phenolics greatly increase flax (Linum usitatissimum) oil stability

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Abstract

Background

Flaxseed oil is characterized by high content of essential polyunsaturated fatty acids (PUFA) promoted as a human dietary supplement protecting against atherosclerosis. The disadvantage of the high PUFA content in flax oil is high susceptibility to oxidation, which can result in carcinogenic compound formation. Linola flax cultivar is characterized by high linoleic acid content in comparison to traditional flax cultivars rich in linolenic acid. The changes in fatty acid proportions increase oxidative stability of Linola oil and broaden its use as an edible oil for cooking. However one of investigated transgenic lines has high ALA content making it suitable as omega-3 source. Protection of PUFA oxidation is a critical factor in oil quality. The aim of this study was to investigate the impact of phenylpropanoid contents on the oil properties important during the whole technological process from seed storage to grinding and oil pressing, which may influence health benefits as well as shelf-life, and to establish guidelines for the selection of new cultivars.

Methods

The composition of oils was determined by chromatographic (GS-FID and LC-PDA-MS) methods. Antioxidant properties of secondary metabolites were analyzed by DPPH method. The stability of oils was investigated: a) during regular storage by measuring acid value peroxide value p-anisidine value malondialdehyde, conjugated dienes and trienes; b) by using accelerated rancidity tests by TBARS reaction; c) by thermoanalytical - differential scanning calorimetry (DSC).

Results

In one approach, in order to increase oil stability, exogenous substances added are mainly lipid soluble antioxidants from the isoprenoid pathway, such as tocopherol and carotene. The other approach is based on transgenic plant generation that accumulates water soluble compounds. Increased accumulation of phenolic compounds in flax seeds was achieved by three different strategies that modify genes coding for enzymes from the phenylpropanoid pathway. The three types of transgenic flax had different phenylpropanoid profiles detected in oil, highly increasing its stability.

Conclusions

We found that hydrophilic phenylpropanoids more than lipophilic isoprenoid compounds determine oil stability however they can work synergistically. Among phenolics the caffeic acid was most effective in increasing oil stability.

Related collections

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The metal chelating properties of flavonoids suggest that they may play a role in metal-overload diseases and in all oxidative stress conditions involving a transition metal ion. A detailed study has been made of the ability of flavonoids to chelate iron (including Fe3+) and copper ions and its dependence of structure and pH. The acid medium may be important in some pathological conditions. In addition, the ability of flavonoids to reduce iron and copper ions and their activity-structure relationships were also investigated. To fulfill these objectives, flavones (apigenin, luteolin, kaempferol, quercetin, myricetin and rutin), isoflavones (daidzein and genistein), flavanones (taxifolin, naringenin and naringin) and a flavanol (catechin) were investigated. All flavonoids studied show higher reducing capacity for copper ions than for iron ions. The flavonoids with better Fe3+ reducing activity are those with a 2,3-double bond and possessing both the catechol group in the B-ring and the 3-hydroxyl group. The copper reducing activity seems to depend largely on the number of hydroxyl groups. The chelation studies were carried out by means of ultraviolet spectroscopy and electrospray ionisation mass spectrometry. Only flavones and the flavanol catechin interact with metal ions. At pH 7.4 and pH 5.5 all flavones studied appear to chelate Cu2+ at the same site, probably between the 5-hydroxyl and the 4-oxo groups. Myricetin and quercetin, however, at pH 7.4, appear to chelate Cu2+ additionally at the ortho-catechol group, the chelating site for catechin with Cu2+ at pH 7.4. Chelation studies of Fe3+ to flavonoids were investigated only at pH 5.5. Only myricetin and quercetin interact strongly with Fe3+, complexation probably occurring again between the 5-hydroxyl and the 4-oxo groups. Their behaviour can be explained by their ability to reduce Fe3+ at pH 5.5, suggesting that flavonoids reduce Fe3+ to Fe2+ before association.

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Author and article information

Contributors

Karolina Hasiewicz-Derkacz: haska3@vp.pl

Anna Kulma: +48713756326 , kulma@ibmb.uni.wroc.pl

Tadeusz Czuj: thadeus@ibmb.uni.wroc.pl

Anna Prescha: aprescha@gmail.com

Magdalena Żuk: mzuk@ibmb.uni.wroc.pl

Magdalena Grajzer: magdalena.grajzer@gmail.com

Marcin Łukaszewicz: marcin.lukaszewicz@uni.wroc.pl

Jan Szopa: szopa@ibmb.uni.wroc.pl

Journal

Journal ID (nlm-ta): BMC Biotechnol

Journal ID (iso-abbrev): BMC Biotechnol

Title: BMC Biotechnology

Publisher: BioMed Central (London )

ISSN (Electronic): 1472-6750

Publication date (Electronic): 30 June 2015

Publication date PMC-release: 30 June 2015

Publication date Collection: 2015

Volume: 15

Electronic Location Identifier: 62

Affiliations

[ ]Faculty of Biotechnology, University of Wroclaw, Przybyszewskiego 63/77, 51-148 Wroclaw, Poland

[ ]Linum Foundation, Plac Grunwaldzki 24a, 50-363 Wroclaw, Poland

[ ]Department of Food Science and Dietetics, Wroclaw Medical University, Borowska 211, 50-556 Wroclaw, Poland

[ ]Department of Genetics, Plant Breeding and Seed Production, The Faculty of Life Sciences and Technology, Wroclaw University of Environmental and Plant Sciences, Pl. Grunwaldzki 24A, 53-363 Wrocław, Poland

[ ]Faculty of Biotechnology, University of Wroclaw, Fryderyka Joliot-Curie 14a, 50-383 Wrocław, Poland

Article

Publisher ID: 178

DOI: 10.1186/s12896-015-0178-0

PMC ID: 4485345

PubMed ID: 26123633

SO-VID: ecf8db5b-14b4-4698-a297-0d8596338955

License:

This is an Open Access article distributed under the terms of the Creative Commons Attribution License ( http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly credited. The Creative Commons Public Domain Dedication waiver ( http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated.

History

Date received : 25 September 2014

Date accepted : 1 June 2015

Custom metadata

ScienceOpen disciplines: Biotechnology

Keywords: flaxseed oil,oil stability,antioxidant activity,phenolic compounds,radical scavenging activity

Data availability:

ScienceOpen disciplines: Biotechnology

Keywords: flaxseed oil, oil stability, antioxidant activity, phenolic compounds, radical scavenging activity

Natural phenolics greatly increase flax ( Linum usitatissimum) oil stability

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