The physicochemical characteristics of seven cold-pressed flaxseed oils sold in New Zealand were investigated for their fatty acid composition, tocopherol composition, moisture and volatile matter, free fatty acids, chlorophyll pigments, unsaponifiable matter, total phenolic acids and flavanoids, and colour. The seven cold-pressed flaxseed oils exhibited significant variations in their physicochemical characteristics. Quality of the oils in terms of oxidative stability was also investigated. Four oils were found to be within the limit of good stability oil indices, measured in terms of peroxide value, p-anisidine value, conjugated dienoic acids, specific extinction in ultraviolet spectrum, acid value and food oil sensor readings (to indicate total polar compounds).
The role of minor constituents in the oxidative stability of two selected oils with different levels of fatty acid composition and minor constituents was investigated. Pan heating at 150�C caused loss of tocopherols, plastochromanol-8, phenolic acids, chlorophyll pigments, β-carotene and lutein and changes in the fatty acid composition. The pan-heated oils exceeded the limit of good stability oil indices using the measurement mentioned above except for acid value. The addition of α-tocopherol to the oils did not provide enhanced protection to the oils in accelerated aging of oil tests at 60�C. It was most likely that phenolic acids present in the oils played a dominant role in the oxidative stability of the oils.
Lipase-catalyzed transesterification of triolein with cinnamic and ferulic acids using a commercially available immobilized lipase B from Candida antarctica (Novozym 435) was conducted to evaluate the antioxidant activity of the lipophilized products as model systems for enhanced protection of unsaturated oil. The lipophilized products were identified using Electrospray Ionization-Mass Spectroscopy (ESI-MS). Separation and isolation of two classes of lipophilized products was also achieved using a solid phase extraction method developed in this study for further investigation into the structure-free radical scavenging activity. Free radical scavenging activity was determined using the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) method. The polarity of the solvents proved important in determining the free radical scavenging activity of the substrates. Ferulic acid showed much higher free radical scavenging activity than cinnamic acid, which had limited activity. The esterification of cinnamic acid and ferulic acid with triolein resulted in significant increase and decrease in the free radical scavenging activity, respectively. These opposite effects were due to the effect of addition of electron-donating alkyl groups on the predominant mechanism of reaction (hydrogen atom transfer or electron transfer) of a species with DPPH. The effect of esterification of cinnamic acid was confirmed using ethyl cinnamate which greatly enhances the free radical scavenging activity. Although, compared with the lipophilized cinnamic acid product, the activity was lower. The free radical scavenging activity of the main component isolated from lipophilized cinnamic acid product using solid phase extraction, monocinnamoyldioleoylglycerol, was as good as the unseparated mixture of lipophilized product. Based on the ratio of a substrate to DPPH concentration, lipophilized ferulic acid was a much more efficient free radical scavenger than lipophilized cinnamic acid.
Lipase-catalyzed transesterification of flaxseed oil with cinnamic and ferulic acids using Novozym 435 was conducted to evaluate whether the lipophilized products provided enhanced antioxidant activity in the oil. The lipophilized products were identified using ESI-MS and were examined for their free radical scavenging activity toward DPPH in ethanol and ethyl acetate. Ferulic acid showed the highest free radical scavenging activity among all substrates tested while cinnamic acid had negligible activity. The effect of esterification of cinnamic acid and ferulic acid with flaxseed oil was similar to that with triolein. Lipophilized ferulic acid was a better free radical scavenger as compared with lipophilized cinnamic acid and extended the naturally-occuring antioxidant capacity of the flaxseed oil. Lipophilized cinnamic acid did not provide much enhanced radical scavenging activity in the flaxseed oil as the presence of natural hydrophilic antioxidants in the oil had much greater radical scavenging activity. It may still be useful for unsaturated oils with a small amount of natural antioxidants in them. Lipophilized cinnamic and ferulic acids showed higher free radical scavenging activity when tested in a less polar solvent (ethyl acetate) whereas ferulic acid showed better activity in a more polar solvent (ethanol).
These results indicate that the choice of solvent for the DPPH assay is critical in evaluating the free radical scavenging activity of substrates of differing polarity, and support previous observations by other authors that the solubility of an antioxidant in relation to the site of oxidation is an important factor for consideration in the use of antioxidants.
| Identifer | oai:union.ndltd.org:ADTP/201527 |
| Date | January 2008 |
| Creators | Choo, Wee Sim, n/a |
| Publisher | University of Otago. Department of Food Science |
| Source Sets | Australiasian Digital Theses Program |
| Language | English |
| Detected Language | English |
| Rights | http://policy01.otago.ac.nz/policies/FMPro?-db=policies.fm&-format=viewpolicy.html&-lay=viewpolicy&-sortfield=Title&Type=Academic&-recid=33025&-find), Copyright Wee Sim Choo |
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