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Oxidation of Polyunsaturated Fatty Acids and its Impact on Food Quality and Human Health

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For many years, both preclinical and clinical studies have provided evidences to support the beneficial effects of ω-3 Polyunsaturated fatty acids (PUFAs), particularly Eicosapen-taenoic acid (EPA) and Docosahexaenoic acid (DHA) in the prevention of chronic diseases. However, recently, an increasing number of studies reported adverse or contradictory effects of ω-3 PUFAs on human health. While dose and experimental condition need to be considered when evaluating these effects, oxidation of PUFAs also serves as an important factor contribut-ing to the inconsistent results. In fact, oxidation of PUFAs happens frequently during food pro-cessing and storage, cooking and even after food ingestion. The free radicals and metabolites generated from PUFA oxidation may adversely affect food quality and shelf life by producing off-flavors and reducing nutritional values. The impact of PUFA oxidation in human health is more complicated, depending on the concentration of products, disease background and targets. This review will introduce different types of PUFA oxidation, discuss its impact on food quality and human health and provide some thoughts for the future research directions.
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Advances in food technology and
nutritional sciences
Open Journal http://dx.doi.org/10.17140/AFTNSOJ-1-123
Adv Food Technol Nutr Sci Open J
ISSN 2377-8350
Oxidation of Polyunsaturated Fatty Acids
and its Impact on Food Quality and
Human Health
Ling Tao*
Department of Animal Science, Cornell University, Ithaca, NY, USA
*Corresponding author:
Ling Tao, PhD
Department of Animal Science
Cornell University
149 Morrison Hall
Ithaca, NY 14853, USA
E-mail: Lt364@cornell.edu
Article History:
Received: November 24th, 2015
Accepted: December 17th, 2015
Published: December 18th, 2015
Citation:
Tao L. Oxidation of polyunsaturated
fatty acids and its impact on food
quality and human health. Adv Food
Technol Nutr Sci Open J. 2015; 1(6):
134-141.
Copyright:
© 2015 Tao L. This is an open ac-
cess article distributed under the
Creative Commons Attribution Li-
cense, which permits unrestricted
use, distribution, and reproduction
in any medium, provided the origi-
nal work is properly cited.
Volume 1 : Issue 6
Article Ref. #: 1000AFTNSOJ1123
Mini Review
Page 134
ABSTRACT
For many years, both preclinical and clinical studies have provided evidences to sup-
port the benecial effects of ω-3 Polyunsaturated fatty acids (PUFAs), particularly Eicosapen-
taenoic acid (EPA) and Docosahexaenoic acid (DHA) in the prevention of chronic diseases.
However, recently, an increasing number of studies reported adverse or contradictory effects
of ω-3 PUFAs on human health. While dose and experimental condition need to be considered
when evaluating these effects, oxidation of PUFAs also serves as an important factor contribut-
ing to the inconsistent results. In fact, oxidation of PUFAs happens frequently during food pro-
cessing and storage, cooking and even after food ingestion. The free radicals and metabolites
generated from PUFA oxidation may adversely affect food quality and shelf life by producing
off-avors and reducing nutritional values. The impact of PUFA oxidation in human health is
more complicated, depending on the concentration of products, disease background and targets.
This review will introduce different types of PUFA oxidation, discuss its impact on food quality
and human health and provide some thoughts for the future research directions.
KEYWORDS: Polyunsaturated fatty acids; Oxidation; Food quality; Human health.
ABBREVIATIONS: ALA: α-Linolenic acid; LOX: Lipoxygenase; COX: Cyclooxygenase; MaR:
Maresin; CYP: Cytochromes P450; PD/NPD: Protectin/neuroprotectin; DHA: Docosahexae-
noic acid; PL: Phospholipase; EPA: Eicosapentaenoic acid; PUFA: Polyunsaturated fatty acid;
GST: Glutathione S-transferase; RvD: D-series resolvin; HHE: 4-Hydroxy-2-hexenal; RvE: E-
series resolvin; HNE: 4-Hydroxy-2-nonenal; FAO: Food and Agriculture Organization; WHO:
World Health Organization; AHA: American Heart Association.
INTRODUCTION
Over the past few decades, chronic diseases including cardiovascular diseases, obesity,
diabetes and cancer have increased rapidly in the USA and other countries of the world.1 Diet
and nutrition are important factors in the maintenance and promotion of good health throughout
the entire life. By far, both preclinical and clinical studies have shown that ω-3 Polyunsatu-
rated fatty acids (PUFAs) in particular Eicosapentaenoic acid (EPA) and Docosahexaenoic acid
(DHA) exert heath benecial effects on cardiovascular diseases, diabetes, cancer and so on.2-5
This leads to institutions worldwide publishing recommendations on the intake of EPA and
DHA. For instance, Food and Agriculture Organization (FAO) and World Health Organization
(WHO) recommend adults to take 0.25-2 g EPA+DHA per day.6 American Heart Association
(AHA) recommends daily intake of 0.5-1 g EPA+DHA per day per adult.7
However, as reviewed by Weylandt et al more recently, there are controversial re-
sults regarding to the health efcacy of ω-3 PUFAs.8 On one hand, the dose and experimental
designs may contribute to the variation in results. On the other hand, with the nature of un-
saturated bonds, PUFAs are prone to oxidation which generates various metabolites as well as
reactive oxygen species. The extent of oxidation and the resulting metabolites may positively
or negatively affect the efcacy of PUFAs. This review will introduce different types of PUFA
Advances in food technology and
nutritional sciences
Open Journal http://dx.doi.org/10.17140/AFTNSOJ-1-123
Adv Food Technol Nutr Sci Open J
ISSN 2377-8350
Page 135
oxidation and discuss the effects of oxidation on food quality
and human health.
ENZYMATIC AND NON-ENZYMATIC OXIDATION OF PUFAs
With multiple unsaturated bonds, PUFA is susceptible
to oxidation, which is categorized into non-enzymatic oxida-
tion and enzymatic oxidation. Non-enzymatic oxidation can
be further divided into autoxidation (mediated by free radicals)
and photooxidation (mediated by ultraviolet or singlet oxygen).
In cells, several types of enzymes including Cyclooxygenases
(COXs), Lipoxygenases (LOXs) and Cytochromes P450 (CYPs)
are able to oxidize PUFAs and generate various metabolites.9
Non-Enzymatic Oxidation
In autoxidation, the reaction is mediated by free radi-
cals, giving rise to a lipid hydroperoxide as the primary oxida-
tion product.10 In many cases, hydroperoxides can be further
oxidized to ketones and ultimate malonaldehyde.11 Hydroxy al-
kenals such as 4-Hydroxy-2-nonenal (HNE), generated by per-
oxidation of ω-6 PUFAs,12-14 and 4-Hydroxy-2-hexenal (HHE),
a product from peroxidation of ω-3 PUFAs15-17 are also widely-
studied autoxidative products of PUFAs. Apart from autooxida-
tion, PUFAs are susceptible to light-induced photooxidation:
photochemical oxidation and photosensitized oxidation.18 The
former one is initiated during exposure to ultraviolet irradia-
tion. Photosensitized oxidation, instead, requires photosensitiz-
ers (i.e. chlorophyll, hemeprotein, riboavin and synthetic dyes)
and visible light.19 The reaction can be categorized into two
types: Type I reaction involves the production of free radicals
by interaction of the excited sensitizer with a substrate; Type
II reaction involves generation of singlet oxygen which further
reacts with PUFAs to produce hydroperoxides.20,21 In this case,
vegetable oils with chlorophyll-like pigments are likely to un-
dergo photooxidation during storage.
Enzymatic Oxidation
In enzymatic oxidation, Phospholipases A2 (PLA2) is
the major phospholipase that cleaves phospholipids at the sn-2
position resulting in free PUFAs and lysophospholipids.22 Af-
ter freeing from membrane, PUFAs can be further catalyzed by
COXs (COX1 or COX2) to form prostaglandin H2. It is unstable
and can be converted into various prostanoids depending on the
cellular prevalence of terminal prostanoid synthases.23,24 In ad-
dition to COX, free fatty acids can be converted by LOXs to
form hydroperoxides. LOXs belong to a family of dioxygenases
which catalyze the insertion of molecular oxygen into PUFAs
with at least one cis, cis-1,4-pentadiene in the structure.25 Some
of the LOX-catalyzed products have recently been discovered as
potent lipid mediators. For example, enzymatic oxygenation of
EPA yields new metabolites, named E-series Resolvins (RvEs),
which were the rst omega-3 lipid mediators reported to resolve
inammation via receptor-specic actions.26-28 Likewise, DHA
can form D-series Resolvins (RvDs),29,30 Protectins/neuroprotec-
tins (PDs/NPDs)31-33 and Maresins (MaRs)34-36 through enzymes-
mediated oxygenation. Those metabolites have been widely
studied to dampen or resolve inammation, protect from renal
or brain dysfunctions, etc. COXs and LOXs can also convert ω-3
and ω-6 PUFAs into different series of prostaglandins, throm-
boxanes and leukotrienes.37 CYPs are better known for their role
in xenobiotic metabolism. However, they can also transform
PUFAs to epoxy-, monohydoxylated-and dihydroxylated-me-
tabolites. Recent work using recombinant human CYP enzymes
has identied the predominant products from the expoxidation
of EPA and DHA as 17,18-epoxyeicosatetraenoic acid and ep-
oxy docosapentaenoic acid, respectively.38
IMPACT OF PUFA OXIDATION ON FOOD QUALITY
Plant oils and sh are known as major sources of ω-3
PUFAs. Soybean oil, canola oil are commonly consumed oil
and are rich in α-Linolenic acid or Alpha-linolenic acid ((ALA),
7.8-9.2%), while some fatty sh including salmon, sardine, and
menhaden contain abundant EPA and DHA (17%-27% of total
fatty acids). Other dietary sources of ω-3 PUFAs include nuts,
seeds, egg yolk, etc.39,40 With the recognition of the health ben-
ecial effects of ω-3 PUFAs, there is a growing industry provid-
ing novel sources of ω-3 PUFAs such as sh oil capsules, algae
products and food enriched with ω-3 PUFAs.41 Our lab recently
used defatted green microalgal biomass to enrich ω-3 PUFAs in
chicken meat42 and eggs (unpublished).
Susceptibility of lipid peroxidation in food depends on
the lipid composition, the presence of prooxidants and antioxi-
dants, oxygen levels, temperature, light and processing meth-
ods.43 PUFA-rich foods are more susceptible for lipid oxidation.
Likewise, presence of prooxidants such as redox active metals
(Fe, Cu) and hemeproteins, exposure to high oxygen levels and
high temperature may accelerate oxidation process. Lipid oxi-
dation often brings problems in food processing and storage.
First, it negatively affects food avor due to the formation of
aldehydes and ketones. Oxidation of PUFAs produces a com-
plex mixture of volatile secondary oxidation products, and these
cause particularly objectionable off-avors.44 For example, soy-
bean oil can undergo “avor reversion”, a type of light-induced
oxidation.45 It has been suggested that the oxidation of ALA in
soybean oil is responsible for the formation of 2-pentylfuran
and its isomer, which may result in avor reversion.46 Butter en-
riched with unsaturated fatty acids or conjugated linoleic acid
may be susceptible to off-avor by generation of oxidized prod-
ucts including 3-methyl-1H-indole (mothball-like), pentanal
(fatty), heptanal (green) and butanoic acid (cheesy).47 Second,
lipid oxidation may reduce the nutritional value by causing the
destruction of essential fatty acids and the lipid-soluble vitamins
A, D, E, and K as well as the decrease in caloric content.48 Third,
free radicals and metabolites formed during oxidation may exert
adverse effects on human health.49 More details of impact on hu-
man will be discussed in the next section.
Given lipid oxidation-triggered negative effects, mul-
Advances in food technology and
nutritional sciences
Open Journal http://dx.doi.org/10.17140/AFTNSOJ-1-123
Adv Food Technol Nutr Sci Open J
ISSN 2377-8350
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tiple methods have been applied to reduce or prevent lipid oxida-
tion so as to improve the food quality. The most commonly used
method is addition of antioxidants. Since the 1940’s, it is known
that vitamin E is a major lipophilic chain-breaking antioxidant
which protects tissue PUFAs against peroxidation50 Serfert et
al found a combination of tocopherols (rich in the δ-derivative
and low in the α-derivative), ascorbyl palmitate and trace metal
chelators (lecithin or citrem) efciently stabilized the oil during
microencapsulation. Addition of rosemary extract in the micro-
encapsulated oil further retarded autoxidation during storage.51
Besides vitamin E, other vitamins or precursors like ascorbic
acid and β-carotene were shown antioxidant activity in food
system.18,52 Plant bioactive compounds particularly polyphenols
have been widely reported to have antioxidant effects. For ex-
ample, apple skin extracts prepared from “Northern Spy” culti-
var were found effective in reducing the lipid oxidation induced
by heat, Ultraviolet (UV) light and peroxyl radicals.53 Although
it is plausible that natural polyphenols could prevent lipid oxida-
tion, the approach of incorporating polyphenols into food and
the effects of polyphenol additives on food avor are not com-
pletely understood. In addition to the antioxidant supplementa-
tion, other methods are used to reduce lipid oxidation. Arruda et
al reported that using nitrogen ushing to remove oxygen in the
headspace of bottled soybean oil increased the sensory quality
during storage. Shelf life can also be increased from 60 up to 180
days as the initial oxygen concentration is reduced from >15%
to <3%.54 Larsen et al found that cups with a high light barrier
(incorporation of a black pigment into the packaging material)
can sufciently protect the sour cream from getting rancid due to
photooxidation.55
IMPACT OF PUFA OXIDATION ON HUMAN HEALTH
In human body, PUFA is susceptible to oxidation un-
der the exposure of free radicals and enzymes such as COXs,
LOXs and CYPs. An increasing number of studies have been
conducted to identify the oxidation pathway of PUFAs and re-
lated metabolites. However, the impact of PUFA oxidation on
human health remains elusive.
HNE, a product from ω-6 oxidation of PUFAs, has been
found in many diseases including atherosclerosis,56,57 neurode-
generative diseases,58,59 cancer60,61 and so on. Indeed, Uchida et
al have recently found that HNE markedly induced intracellular
ROS production in cultured rat hepatocytes RL34 cells.62 This
pro-oxidant effect of HNE was also observed in human neuro-
blastoma SH-SY5Y cells.63 Awada et al reported that oxidized
PUFAs (rich in HNE and HHE) induced oxidative stress and in-
ammation in mice and in human intestinal Caco-2/TC7 cells.64
In human trials, Jenkinson et al also found that high PUFA diet
(15% PUFA) signicantly increased whole blood oxidized glu-
tathione and urinary thiobarbituric acid reactive substances, in-
dices of oxidative stress, in healthy male subjects.65 Interestingly,
PUFA oxidation products have also been reported to activate
antioxidant pathways which detoxify cytotoxic xenobiotics. For
instance, HNE has been shown to enhance the gene and protein
expression of class P Glutathione S-Transferase (GST-P) as well
as the total GST activity in normal rat liver epithelial cells.66
HNE can also activate antioxidant response element, leading
to the induction of class A GST isozymes, such as GSTA1 and
GSTA4, in rat clone 9 hepatoma cells.67 In addition, HHE up-
regulated nuclear factor, erythroid 2-like 2, an important regula-
tor of antioxidant responses in the heart of high fat-fed mice.68
The bi-directional effects of HNE or HHE are concentration de-
pendent. HNE at concentration lower than 10 μM tends to exert
benecial effects while higher concentrations may have toxic
effects.69 As supported by Zhang et al, treating cardiomyocytes
with small, subtoxic doses (5 μM) of HNE offered protection
from subsequent exposure to toxic doses (>=20 μM).70
Over a decade, a growing number of PUFA metabolites
have been discovered, including ω-3 PUFAs-derived resolvins,
protectins, maresins, prostaglandin-3-, thromboxane-3- and
leukotriene-5-series as well as ω-6 PUFA-derived prostaglan-
din-2-, thromboxane-2- and leukotriene-4-series.37,71 ω-3 PU-
FA-derived metabolites have shown potent anti-inammatory,
tissue protective and resolution-stimulating functions. For in-
stance, RvDs and PD1/NPD1 inhibit neutrophil inltration into
injured kidneys, block toll-like receptor-mediated inammatory
activation of macrophages and mitigate renal dysfunctions.72
Recently, Chiang et al demonstrated a previously unrecognized
role of GPR18 as a receptor for RvD2 that stimulates effero-
cytosis and mediates the resolution of inammation.73 Anoth-
er type of lipid mediator, MaR1 and MaR2 were identied to
have potency at enhancing human macrophage phagocytosis
and efferocytosis.34,74 ω-3 PUFAs-derived prostaglandin-3- and
leukotriene-5-series have been found to exert anti-arrhythmic
and anti-inammatory effects, respectively. By contrast,
ω-6 PUFAs-derived prostaglandin-2-series have shown pro-
arrhythmic effects and leukotriene-4-series from ω-6 PUFAs
have presented pro-inammatory effects.37,75 This indicates that
enzymatic oxidation products of ω-3 and ω-6 PUFA may exert
opposing effects on human health.
From current studies, we learnt that more PUFAs do
not necessarily yield better effects as they may undergo oxida-
tion and produce metabolites that exert adverse effects at high
levels. Co-supplementation with antioxidants such as vitamin C
and vitamin E may reduce autoxidation of PUFAs and poten-
tially enhance the efcacy. In addition, increasing ω-3 to ω-6
ratio in the diet is likely to produce more benecial metabolites,
thereby enhancing efcacies of PUFAs. The optimal dose of PU-
FAs, antioxidant supplementation as well as ω-3 to ω-6 ratio,
however, require additional research evidences.
CONCLUSION
As summarized in Figure 1, through non-enzymatic
and enzymatic oxidation, PUFAs are transformed to various
metabolites. In most cases, oxidation of PUFAs results in off-
avors and reduction of food quality and shelf life. The oxida-
tion may induce oxidative stress and inammation when the
Advances in food technology and
nutritional sciences
Open Journal http://dx.doi.org/10.17140/AFTNSOJ-1-123
Adv Food Technol Nutr Sci Open J
ISSN 2377-8350
Page 137
metabolites are at high concentrations. At low concentrations,
the metabolites may exert antioxidant effects. The enzymatic
oxidative products of ω-3 and ω-6 PUFAs may have opposing
effects on inammation and cardiac arrhythmicity. At present,
the functions and working mechanisms of PUFA metabolites are
not completely understood. Moreover, whether PUFA itself or
oxidized PUFA metabolites play more important roles in vari-
ous disease context remains unclear. Herein, future studies are
needed to tackle these problems.
CONFLICTS OF INTEREST
The authors declare that they have no conicts of interest.
ACKNOWLEDGMENT
The author would like to acknowledge Dr. Lei Liu, currently
an Assistant Professor in College of Veterinary Medline, Hunan
Agricultural University, China for the helpful comments and
suggestions.
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Figure 1: The oxidation of PUFAs and its impact on food quality and human health. With multiple unsaturated bonds, PUFAs can undergo both non-
enzymatic and enzymatic oxidation and generate a variety of metabolites. Oxidation of PUFAs often brings adverse effects to food by producing off-avors,
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COX: Cyclooxygenase; CYP: Cytochromes P450; DHA: Docosahexaenoic acid; EPA: Eicosapentaenoic acid; HHE: 4-Hydroxy-2-hexenal; HNE: 4-Hy-
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... However, they are also sensitive to oxygen and can potentially cause adverse effects. It is hypothesized that the quality and stability of cosmetic formulations affects many different areas: a. Skin care and dermatological effectiveness: when ingredients change due to oxidative degradation, their anti-inflammatory and anti-oxidant effects can be reduced [2]. b. ...
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... But, the main obstacle for developing omega-3 fatty acids fortified stable functional food is that they are highly susceptible to auto-oxidation due to high degree of unsaturation in their molecular structure [6]. The oxidation of double bonds in highly unsaturated omega-3 fatty acids reduces the nutritional benefits, and produced reactive oxygen species, as well as unhealthy volatile compounds with off-flavors and undesirable odors [7]. Relevant literature reveals that among the methods employed for controlling lipid oxidation, use of antioxidants is the most effective, convenient and economical means. ...
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