View Article Online / Journal Homepage / Table of Contents for this issue

TUTORIAL REVIEW www.rsc.org/csr | Chemical Society Reviews

Lipid oxidation and improving the oxidative stability

Fereidoon Shahidi and Ying Zhong
Received 22nd October 2009
DOI: 10.1039/b922183m
Published on 09 July 2010. Downloaded by Lomonosov Moscow State University on 12/06/2013 14:59:58.

Lipids are a major component of food and important structural and functional constituents of
cells in biological systems. However, this diverse group of substances is prone to oxidation
through various pathways. Their oxidative stability depends on a number of intrinsic and
extrinsic factors, including the unsaturation of their fatty acids, composition of minor
components, environment conditions, delivery techniques and use of antioxidants, among others.
Lipid oxidation has detrimental effects on both food quality and human health, and efforts must
be made to minimize oxidation and improve oxidative stability of lipid products. Antioxidant
strategy has been successfully employed in the food industry for quality preservation of the food
products and in the medicinal industry for risk reduction of numerous oxidative stress-mediated
diseases. This tutorial review will provide important knowledge about lipid oxidation, including
the mechanism and factors involved in oxidation, as well as strategies for improving oxidative
stability of lipids.

1. Introduction of lipids
Lipids are an important component of food and most
biological systems and are also used in a number of industrial
applications. They serve as a condense source of energy and
lipid-soluble vitamins in food and constitute the structural
components of cell membranes while also functioning as
important signaling agents in biological systems. Lipids in
food products, either naturally occurring or added exogenously,
provide a heat transfer medium for food processing and render
desirable texture and flavour to the products. Lipids are one of
the major macronutrients required for growth and maintenance
of the functions of living organisms, however, excessive dietary
intake of lipids has its own implications. Overconsumption of
lipids especially the ‘‘bad’’ lipids (e.g. certain saturated lipids
Department of Biochemistry, Memorial University of Newfoundland,
St.John’s, NL, Canada A1B 3X9
and trans fats) has been associated with a number of diseases
and health conditions, including obesity, hypertension,
cardiovascular disease and cancers.
1.1 Composition of lipids
There is no precise definition available for the term ‘‘lipid’’.
While early definitions were mainly based on their solubility in
organic solvents such as hexane, chloroform or ether and
insolubility in water, limitations apply where exceptions are
found for monoacylglycerols of some short chain fatty acids,
which are more soluble in water than in organic solvents. It is
generally accepted that lipids include a broad spectrum of
compounds that have the same common properties and
compositional similarities and these relate to a larger extent
to their solubility than their structural characteristics.1 Hence
a diverse group of compounds are referred to as lipids,
including triacylglycerols (TAG), diacylglyerols (DAG),
monoacylglycerols (MAG), glycolipids (GL), phospholipids

Fereidoon Shahidi received his Ying (Joy) Zhong received

Fereidoon Shahidi
PhD in physical organic
chemistry from McGill Uni-
versity in Montreal, Canada.
Currently, he is a University
Research Professor in the
Department of Biochemistry
at Memorial University of
Newfoundland. He has received
numerous awards, including
the American Chemical Society
Award for the Advancement of
Application of Agricultural
and Food Chemistry as well
as the 2010 European Lipid
Technology Award from
European Federation For the
Science and Technology of
Lipids.
her MSc degree in Food
Science from Memorial
University of Newfoundland
in St. John’s, Canada and
is continuing towards her
PhD degree with Professor
Fereidoon Shahidi in the same
University. Her research
interests focus on the chemistry
of natural antioxidants and
their health benefits.
Ying Zhong

This journal is 
c The Royal Society of Chemistry 2010 Chem. Soc. Rev., 2010, 39, 4067–4079 | 4067

Table 1 Lipid classes and examples
Lipid class Example
Neutral lipids
Triacylglyerol 1,2,3-Trioleoylglycerol
Diacylglyerol 1,3-Dioleoylglycerol
Monoacylglyerol 1-Oleoylglycerol
Fatty acid Oleic acid
Published on 09 July 2010. Downloaded by Lomonosov Moscow State University on 12/06/2013 14:59:58.
Alcohol Hexadecanol
Wax Hexadecyl oleate
Sterol Cholesterol, b-sitosterol
Sterol ester Cholesteryl oleate
Hydrocarbon b-Carotene
Polar lipids
Glycolipids Digalactoyldiacylglyerol
Phospholipids Phosphatidylcholine
Sphingolipids Sphingomyelin
Fat-soluble vitamin Vitamins A, D, E and K
(PL), sphingolipids, fatty acids, long chain alcohols, waxes,
sterols, and fat-soluble vitamins, among others (Table 1).
These compounds can be categorized into different lipid
classes based on their physical properties (fats/oils), polarity
(neutral/polar), chemical structure (simple/complex/derived)
or essentiality (essential/nonessential).
Lipids are mostly esters of fatty acids and glycerol. Nearly
98% of lipids in plants and animals consist of acylglyerols,
namely, TAG, DAG and MAG, which contain three, two and
one ester bond, respectively. TAG are the most abundant
constituents in fats and oils of commercial and dietary
importance. In vegetable oil, for example, TAG comprise
more than 95% of the total lipid.2 In living organisms, TAG
play an important role in metabolism as energy sources and
transporters of dietary fat. Different from TAG, PL are
surface active, due to the presence of both lipophilic and
hydrophilic portions in their molecules, and constitute the
major components of biological membranes. PL usually have
a different fatty acid composition from that of TAG, displaying a
higher degree of unsaturation.
Fatty acids are the building blocks of lipids and to a large
extent determine their physico-chemical and physiological
properties. Natural fats contain primarily even-numbered
straight-chain fatty acids. However, odd-numbered, branched-
chain or cyclic, and hydroxyl acids are also present in minor
amounts in natural as well as processed fats. Naturally
occurring fatty acids show varied degree of unsaturation
depending on their origin. Depot fats of most, if not all,
higher land animals are high in saturated fatty acids, in
particular stearic acid (C18:0). Plant oils are relatively low in
saturated fatty acids, with palmitic (C16:0), oleic (C18:1),
linoleic (C18:2) and linolenic (C18:3) acids being predominant.
Milk fat contains a large proportion of short chain fatty acids
(C4–C10). Marine oils, including algal, marine fish and marine
mammal oils, are a rich source of polyunsaturated fatty acids
(PUFA), especially those with long chains (C20, C22),
which are of biomedical interest.3–5 While some fatty acids,
mainly saturated and monounsaturated fatty acids, can be
biosynthesized in the body, PUFA must be provided through
the diet and/or supplements for health maintenance. The latter
group is known as essential fatty acids (EFA), which include
some omega-6 and omega-3 PUFA derived from linoleic
4068 | Chem. Soc. Rev., 2010, 39, 4067–4079
View Article Online
and a-linolenic acid, respectively, through elongation and
desaturation. Plants are able to synthesize and interconvert
these EFA and provide dietary sources for animals. EFA are
precursors of the metabolically active prostagladins and
leukotrienes, which play important roles in the immune
response.6 Omega-3 PUFA are of biological and medicinal
interest, and have been shown to possess a variety of health
effects, including anti-inflammatory, cardioprotective and
anticancer activities, among others.7–10 Omega-3 oils are
now commercially available in various forms as specialty
lipids. Unlike PUFA, saturated fatty acids are considered less
desirable for health and nutrition, as they are believed to
render harmful effects to health. Saturated fatty acids have
been associated with increased incidence of atherosclerosis and
coronary heart disease.11 However, stearic acid has recently
been found to be neutral or even protective in development of
cardiovascular disease.12
Although acylglycerols predominate in fats and oils, minor
components also make important contributions to the quality
characteristics, stability and applications of lipids. Minor
components in fats and oils include mainly phospholipids
and unsaponifiable matter such as sterols (cholesterol in
animal fats and phytosterols in plant oils), terpenic and
aliphatic alcohols, phenolics (including tocopherols and
tocotrienols, collectively known as tocols), and hydrocarbons
(including carotenoids and squalene), among others. They are
generally present in oils at less than 2%, but may play a major
role in rendering stability and special functionalities to oils.2
These components not only provide good markers for the
authentication of fats and oils (e.g. phytosterols), they also
possess biological and physiological activities (e.g. tocols,
carotenoids, phytosterols, etc.) and thus are considered as a
potential source of nutraceuticals. Some may exhibit anti-
oxidant properties that help to stabilize lipids against
oxidation, while others may act as pro-oxidants under certain
conditions and adversely affect their oxidative stability. The
antioxidant/pro-oxidant balance is important in predicting the
oxidative stability of the lipid.
1.2 Occurrence of lipids
Lipids are widely distributed among plant, animal and
microbial sources. Lipids for food, cosmetic and medicinal
use are produced from plants such as oilseeds, tropical fruits,
herbs and spices, and alga as well as from animal origins such
as land-based animals, fish, marine mammals and derived
sources. In addition to naturally occurring fats and oils, novel
lipids are developed to achieve desired physical and/or
chemical properties, extended shelf-life, improved nutritional
value and expanded applications. Fatty acid profile of lipids,
including the chain length, unsaturation of fatty acids and the
TAG structure, can be modified through breeding and genetic
engineering of the source plant.13 Alternatively, lipids can be
modified by chemical or enzymatic means and via processes
such as hydrogenation, fractionation and interesterification.
For example, incorporation of marine-derived long-chain
essential fatty acids into plant oils results in structured lipids
with altered fatty acid composition and/or positional distribution
on the glycerol backbone.14,15 Structured lipids have been of
This journal is 
c The Royal Society of Chemistry 2010

great interest as nutraceuticals and functional food ingredients
due to their beneficial effects on a range of metabolic para-
meters including immune function, nitrogen balance,
and improved energy release and lipid clearance from the
bloodstream, among others.16
Published on 09 July 2010. Downloaded by Lomonosov Moscow State University on 12/06/2013 14:59:58.
2. Lipid oxidation
2.1 Introduction of lipid oxidation
Lipid oxidation is a major cause of quality deterioration in
food and negatively affects the integrity of biological systems.
The oxidative changes in food give rise to the development of
off-flavours, loss of nutrients and bioactives, and even formation
of potentially toxic compounds, thus making the lipid or lipid-
containing foods unsuitable for consumption. Lipids in living
organisms may also undergo oxidation during normal aerobic
metabolism or upon exposure to other oxidizing agents.17
Oxidation in vivo has destructive cellular effects and has been
associated with pathophysiology of numerous diseases and
health conditions including inflammation, atherosclerosis,
cancer and aging, among others.18–21
Lipids are susceptible to oxidation in the presence of
catalytic systems such as light, heat, enzymes, metals, metallo-
proteins and microorganisms, leading to complex processes of
autoxidation, photooxidation, thermal or enzymatic oxidation,
most of which involve free radicals and/or other reactive
species as the intermediate. Autoxidation is the most common
process among all and is defined as the spontaneous reaction
of lipids with atmospheric oxygen through a chain reaction
Fig. 1 Lipid autoxidation pathways.
This journal is 
c The Royal Society of Chemistry 2010
View Article Online
of free radicals. The process can be accelerated at higher
temperatures as in thermal oxidation. Photooxidation involves
excitation of a photosensitizer and energy transfer to lipid
molecules or oxygen. Oxidation can also be catalyzed by
certain enzymes such as lipoxygenases. Unsaturated fatty
acids are the major reactants affected by such reactions,
whether they are present as free fatty acids, simple alkyl esters,
acylglycerols or phospholipids. The PUFA in membrane
phospholipids and cholesterol, especially low density lipo-
protein (LDL)-cholesterol, are the major target substrates of
oxidation in vivo, causing irreversible cellular and tissue
damage.
2.2 Lipid autoxidation pathways
It has been widely accepted that lipid autoxidation occurs via a
free radical chain mechanism that proceeds through three
distinct stages of initiation, propagation, and termination,
leading to a series of complex chemical changes. A simplified
scheme explaining the mechanism of autoxidation is given in
Fig. 1.
Unsaturated lipid molecules, in the presence of initiators
such as heat, light/ionizing radiation and metal ions/metallo-
proteins, lose a hydrogen atom and produce free radicals. The
lipid radicals then react with oxygen to form peroxyl radicals,
which act as the chain carriers of the rapid progressing
reaction by attacking a new lipid molecule. This reaction
may be repeated for several thousand times during propagation
until no hydrogen source is available or the chain is
interrupted, for example, by antioxidants.13 Therefore, lipid
Chem. Soc. Rev., 2010, 39, 4067–4079 | 4069

oxidation is a self-propagating and self-accelerating process.
Oxidation normally proceeds very slowly at the initial stage,
until it reaches a sudden increase after an induction period.
The initiation of lipid oxidation requires the presence of
initiators or catalysts, which have been summarized by
Schaich.22 The initiation process is quite complex and not
yet fully understood; however, it is believed to involve removing
Published on 09 July 2010. Downloaded by Lomonosov Moscow State University on 12/06/2013 14:59:58.
of a hydrogen atom in the lipid molecule. The loss of hydrogen
atom takes place most readily at the carbon next to the double
bond in the olefinic fatty acids, due to lower C-H bond energy.
The dissociation energy of hydrogen in various compounds
was presented by Ohloff23 as given in Table 2. The bisallylic
hydrogen in PUFA requires the lowest activation energy
for initiation of free radical formation, followed by allylic
hydrogen while alkyl hydrogen requires the highest
energy, suggesting their decreased susceptibility to oxidation.
In other words, oxidation is accompanied by a reduced
Table 2 The dissociation energy of hydrogen in various compounds
Compounds DE (kcal/mol)
103
100
85
77
65
H–OO–R 90
1
Fig. 2 H NMR spectrum of canola oil.
4070 | Chem. Soc. Rev., 2010, 39, 4067–4079
View Article Online
proportion of allylic and bisallylic hydrogens, which can be
monitored by using proton NMR spectroscopy (e.g. as in Fig. 2).
The lipid free radicals generated during initiation and
propagation are stabilized by radical resonance (as shown
below), which also leads to shift of double bonds and cis-trans
isomerization.
Conjugated dienes and trienes are produced, due to the
rearrangement of the methylene-interrupted double bonds in
PUFA, and are used as an indicator of oxidation.24
During propagation, lipid hydroperoxides are produced as
primary products of oxidation (Fig. 1). They are unstable and
break down to a wide range of secondary oxidation products,
including aldehydes, ketones, alcohols, hydrocarbons, volatile
organic acids and epoxy compounds, among others, some of
which have undesirable odours with very low threshold values.
Therefore, oxidation-related rancidity are generally related to
the secondary oxidation products. Meanwhile, alkoxyl (RO ),
peroxyl (ROO ), hydroxyl ( OH) and new lipid radicals (R )
are generated from decomposition of hydroperoxides, and
further participate in the chain reaction of free radicals.
Decomposition of hydroperoxides is more likely through
cleavage of O–O bond of the hydroperoxide to form alkoxyl
and hydroxyl radicals, as O–O bond cleavage (DE 44 kcal/mol)
is thermodynamically more favoured than that of the
O–H bond which requires a higher activation energy
(DE 90 kcal/mol).25 Possible pathways for hydroperoxide
This journal is 
c The Royal Society of Chemistry 2010

decomposition and formation of secondary oxidation
products are given below.
Published on 09 July 2010. Downloaded by Lomonosov Moscow State University on 12/06/2013 14:59:58.
At low temperatures such as in cold storage, breakdown of
hydroperoxides is dominated by metal ion-mediated electron
transfer mechanism (as shown below).26 The haem and
non-haem iron provide a source of metal ion required for this
reaction.
Fe2+ + ROOH - Fe3+ + RO + OH
The alkoxyl radicals may also undergo rearrangement and
cyclization to form stereospecific epoxides. The type of
secondary oxidation products produced depends on the
composition of the hydroperoxides and pattern of oxidative
cleavage, in other words, the composition of the fatty acid
substrates and reaction conditions. For instance, hexanal is
formed as one of the major secondary oxidation products of
linoleic and other o6 fatty acids, whereas oxidation of o3 fatty
acids results in the production of propanal.27 Individual
carbonyl compounds as indicators of lipid oxidation can be
identified and quantified by using chromatographic techniques
for assessing oxidative deterioration of different lipid systems.
The aldehydes formed from hydroperoxide decomposition
can be further oxidized to organic acids and other tertiary
oxidation products, which may be measured by monitoring the
system conductivity changes. Hydroperoxides and many of the
secondary oxidation products are highly reactive themselves
and may initiate further oxidation reactions. They are
also toxic to tissues and cells of living organisms. In the
termination stage of oxidation, radicals neutralize each
other through radical–radical coupling or radical–radical
disproportionation to form stable non-radical products,
including a variety of polymers products.26 The formation of
polymers during oxidation of membrane phospholipids leads to
reduced fluidity of the membranes, affecting membrane transport
and cell signaling, as observed in Alzheimer’s disease.28
2.3 Photooxidation
In addition to the normal or ground state (triplet) oxygen in
autoxidation, the excited state (singlet) oxygen can be involved
in lipid oxidation by directly reacting with the double bonds of
This journal is 
c The Royal Society of Chemistry 2010
View Article Online
unsaturated fatty acids through non-radical pathways, as
commonly encountered in photooxidation. Singlet oxygen
(1O2) is an excited state of oxygen, which can be generated
from triplet oxygen by chemical, photochemical and
enzymatic means as well as by decomposition of hydro-
peroxides.29 Singlet oxygen is a major reactive oxygen species
(ROS) that readily (1500 times faster than triplet oxygen)
participates in the oxidation process. Light-induced
production of singlet oxygen requires the presence of photo-
sensitizers such as chlorophyll, pheophytins, riboflavin,
myoglobin and heavy metals, which are widely found in
nature. These photosensitizers absorb energy from light
(visible or ultraviolet) and are activated to an excited singlet
state (1Sen*). The excited singlet photosensitizers are very
unstable and tend to return to ground state by either reacting
directly with the lipid substrates (type I photosensitizers) or
activating triplet oxygen to singlet oxygen (type II photo-
sensitizers), which readily initiates the oxidation process.
The reactions of photosensitizer-involed lipid oxidation are
shown in a simplified scheme below.
Type I
hn
Sen ! 1Sen
O2
1
Sen þ RH ! 
SenH þ R ! ROOH þ Sen; or
1
Sen þ RH ! ðSen þ RHþ Þ or ðSenþ þ RH Þ
O2
! ROOH þ Sen
Type II
hn
Sen ! 1Sen
1
Sen* + O2 - Sen + 1O2
1
O2 + RH - ROOH
Type I photooxidation proceeds via a free radical or free
radical ion route, leading to the formation of hydroperoxides;
whereas in type II photooxidation, the highly electrophilic
singlet oxygen reacts directly with the double bonds of
unsaturated fatty acids by addition rather than through free
radical intermediates. Hydroperoxides are generated during
singlet oxygen attack, accompanied by a shift of the double
bonds in the molecules, as shown below for photooxidation of
methyl linoleate.
Instead of loss of the the bisallylic hydrogen and formation
of equal amounts of C9–OOH and C13–OOH with a
concomitant formation of a conjugated diene structure
(D10,12 or D9,11) in autoxidation, photo-oxidation of linoleate
yields a mixture of four derivatives with the hydroperoxy
Chem. Soc. Rev., 2010, 39, 4067–4079 | 4071

group on either of C9, C10, C12 or C13. The autoxidation
may then proceed following formation of hydroperoxide by
singlet oxygen, producing multiple intermediates and oxidation
products that change with reaction conditions and time.
Photooxidation makes significant contribution to oxidative
changes of foods or biological organisms exposed to solar light
and UV radiation, such as liposomes and cell membranes that
Published on 09 July 2010. Downloaded by Lomonosov Moscow State University on 12/06/2013 14:59:58.
are subjected to photooxidation in numerous skin disorders,
including phototoxicity, photoallergy, photosenescence,
photoaging and photocarcinogenesis. The significant effect
of photooxidation has been attributed to the long lifetime of
singlet oxygen in the hydrophobic cell membrane (longer than
in aqueous solution), and the quick occurrence of the reaction
(30 000 times quicker than autoxidation for oleic acid and
1000–1500 times quicker for polyenes).
3. Factors affecting lipid oxidation
3.1 Fatty acid profile
Lipid oxidation is a complex process whose rate and course are
influenced by many factors. Oxidative susceptibility of lipids
depends primarily on the composition of their fatty acids,
more specifically, their degree of unsaturation or methylene
bridge index (MBI, the mean number of bisallylic methylene
positions). PUFA (structures shown in Fig. 3) with the highest
MBI value are most susceptible to oxidation. The oxidation
rate of the fatty acid series stearic, oleic, linoleic and linolenic
acid, for instance, was reported to be in the ratio of
1 : 100 : 1200 : 2500.13 Oils with high proportions of unsaturated
fatty acids show compromised oxidative stability. Oils
originating from certain plant sources as well as those from
marine origin such as algae, fish/shellfish and mammal oils are
Fig. 3 Chemical structures of typical long-chain omega-3 polyunsaturated fatty acids (PUFA).
4072 | Chem. Soc. Rev., 2010, 39, 4067–4079
View Article Online
known for their high PUFA content, and are among the highly
unstable oils. Unsaturated fatty acids as main reactants
display significant compositional changes during oxidation,
which provide an indirect measure for the extent of oxidation.
3.2 Positional distribution of fatty acids
The stereospecific positional distribution of fatty acids in the
TAG molecules also plays a role in susceptibility of lipids to
oxidation. It is believed that the location of PUFA in the sn-2
position of the glycerol backbone helps their stability
against oxidation.30 Shen and Wijesundera31 investigated the
oxidative stability of two regio-isomer TAG molecules SSD
(1,2-distearoyl-3-docosaenoyl glycerol) and SDS (1,2-distearoyl-
3-docosaenoyl glycerol) and revealed that DHA is more stable
to oxidation when located at the sn-2 position of the TAG.
This may, at least partially, explain why randomized vegetable
oils oxidize faster than their corresponding parent natural oils,
in which PUFA are preferentially located at sn-2 positions.32
The difference in oxidation rate observed for TAG regio-
isomers may be attributed to the interaction of acyl chains
within the same TAG molecule and possible steric hindrance
for hydroperoxide formation, which are to be further
investigated.
3.3 Lipid class
Variations in oxidative stability exist among different lipid
classes. In general, fatty acids have been shown to oxidize
faster in the free form than their glyceryl esters, possibly due to
greater ability to pick up trace metals from the environment.33
PL show higher susceptibility to oxidation than TAG, and are
major contributors to the development of warmed-over
flavour in meat. The relatively high reactivity of PL in oxidation
This journal is 
c The Royal Society of Chemistry 2010
 View Article Online

has been attributed to the: (1) difference in their fatty acid 3.5 Environmental factors
composition, e.g. higher proportions of PUFA in PL in order
In addition to the nature of the lipid, environmental factors to
to keep fluidity of membranes; (2) location at the tissue-air
which lipid is exposed during processing and storage may
interface and arrangement in membrane that facilitates
also affect its oxidation rate. Although lipids are naturally
propagation; and (3) greater proximity to catalytic sites of
occurring in various sources, procurement of commercial fats
oxidative enzymes.26 PL in the body are important membrane
and oils requires extraction and refining operations, which
material, and their oxidation leads to alterations of fluidity,
Published on 09 July 2010. Downloaded by Lomonosov Moscow State University on 12/06/2013 14:59:58.

may introduce modulations in the oxidative stability of the

permeability and selectivity of the membrane and
final products through exposure to high temperature, light,
consequently modulation of cellular metabolisms. Within the
atmospheric oxygen and moisture, and possibly the contact
PL class, individual PL compounds have varying oxidative
with worn metals. The refining processes may affect the minor
stability depending on their fatty acids profile and the
components which are important to oxidative stability of the
nature of the polar head group which influences the alignment
lipids (Table 3). Lipids may also undergo oxidative changes
of the PL molecule. Pikul and Kummerow34 indicated that
during packaging and upon storage of bulk oils as well as
phosphatidylinositol (PI) with the highest PUFA percentage
during processing of the lipid-containing materials such as
exhibited the highest oxidation rate, followed by phosphatidyl-
roasting and deep frying.
ethanolamine (PE), phosphatidylserine (PS) and phosphatidyl-
In biological systems, oxidative stress is rendered by numerous
choline (PC). In a liposome model system of constant fatty acid
reactive oxygen species (ROS) in the environment, leading to
composition, PE-based liposomes were oxidized to a greater
many pathological alterations. The primary ROS is superoxide
extent than PC-based liposomes.35
anion (O2 ), which is formed from the single-electron
reduction of molecular oxygen through a variety of sources
3.4 Minor components under both physiological and pathophysiological conditions.
Approximately 2–5% oxygen consumed by a cell is reduced to
The presence of minor components in fats and oils also affects
oxygen radicals.40 Superoxide anion can be neutralized by
their oxidative stability in both positive and negative manners.
superoxide dismutase (SOD) to yield hydrogen peroxide; the
Phospholipids have been demonstrated to act as antioxidants
latter is a known non-radical ROS and, although less reactive
synergistically with other antioxidative substances.36 Tocols
than superoxide anion, has a longer lifetime and a higher
(vitamin E) are important fat-soluble antioxidants and show
diffusibility and can cross biological membranes freely.41
enhanced antioxidant efficiency in the presence of phospholipid
Moreover, it can react in Fenton reaction with reduced metal
synergists.36 Carotenoids, the yellow-red pigments in most
ions such as Fe2+ and Cu+ to form hydroxyl radical ( OH),
crude oils, are a group of unsaturated tetraterpenes and
which is considered as the most harmful ROS. Other ROS
their oxygenated derivatives, whose antioxidant activity has
include hydroxyalkenals, singlet oxygen and ozone, among others.
been well documented.37 Tocols and carotenoids contribute to
the stability of crude oils, in which they are not removed by
deodourization and bleaching during the refining process. Table 3 Effect of processing steps on the removal of minor
Phenolic compounds, other than tocols, are among the components from the oils
most abundant antioxidants from natural sources and their
Processing Components eliminated
presence in vegetable oils plays an important role in the
protection against oxidation. Major phenolics in olive oil, Degumming Phospholipids
for example, include oleuropein, ligstroside, tyrosol, Refining Free fatty acids, phospholipids,
metal ions and soaps
hydroxytyrosol and certain lignans.30 Chlorophylls which Bleaching Pigments, primary oxidation
render a green colour to most plants and plant products, products
including oils, may function as antioxidants in the dark, Fractionation Waxes, solid triacylglycerols
Deodourization Free fatty acids, secondary
however, they act as photosensitizers in the presence of light oxidation products, residual
and thus catalyze lipid photooxidation. These minor pigments, sterols, hydrocarbons,
components constitute a cocktail mixture in fats and oils, other volatiles
modulating the oxidation process through various mechanisms.
Effect of minor components on oxidative stability of oils Table 4 Major reactive species in food and biological systems
has been investigated by comparing oxidation of stripped
and non-stripped natural oils.38,39 In food or biological Free radicals Non-radicals
environments where the non-lipid components with antioxidant Reactive oxygen species (ROS)
potential are present (e.g. free amino acids and peptides, Superoxide anion (O2 ) Hydrogen peroxide (H2O2)
Hydroxyl ( OH) Hydrochlorous acid (HOCl)
Maillard reaction products, and/or additives), the lipids may Alkyl (R ) Singlet oxygen (1O2)
show enhanced oxidative stability. On the other hand, other Alkoxyl (RO ) Ozone (O3)
components like trace metals, certain enzymes and haem Peroxyl (ROO ) Hydroxyalkenals
compounds act as catalysts of oxidation reactions and lead Hydroperoxyl (HOO )
Reactive nitrogen species (RNS)
to compromised oxidative stability of the lipids in the Nitric oxide ( NO) Peroxynitrite (ONOO)
envrionment. Therefore, qualitative and quantitative control Nitrogen dioxide (NO2 ) Alkyl peroxynitrite (LOONO)
of these minor components is important in quality assurance Dinitrogen trioxide (N2O3)
Nitrous acid (HNO2)
of lipid and non-lipid based products.

This journal is 
c The Royal Society of Chemistry 2010 Chem. Soc. Rev., 2010, 39, 4067–4079 | 4073

Nitrogen dioxide and peroxynitrite anion formed from the
interaction of nitric acid with superoxide anion are also strong
oxidants, and together with nitric oxide (NO) are known as
reactive nitrogen species (RNS). Table 4 summarizes the
reactive oxygen and nitrogen species involved in biological
oxidation.
Published on 09 July 2010. Downloaded by Lomonosov Moscow State University on 12/06/2013 14:59:58.
4. Improving the oxidative stability of lipids
4.1 Encapsulation
Encapsulation/microencapsulation techniques have been
employed for stabilization of specialty lipids such as omega-3
oils for pharmaceutical, food and supplement use. The omega-3
fatty acid-rich fish oils contain high proportions of long
chain PUFA such as EPA (eicosapentaenoic acid) and DHA
(docosahexaenoic acid), and to a lesser extent DPA (docosa-
pentaenoic acid), which are also commercially available in
their concentrated forms. These long-chain omega-3 PUFA
are known to lower blood serum TAG levels, and to be
effective for alleviating arrhythmia. Furthermore, DHA is
essential for proper functioning of the eye and may play a
structural role in the brain. EPA serves as a precursor to
eicosanoids and has therapeutic benefits for human cardiovascular
diseases as well as mental disorders such as Schizophrenia
where inflammation might be involved.8,9 However, the highly
unsaturated fatty acids in the oils are exceptionally susceptible
to autoxidation and can form complex mixtures of high
molecular weight polymeric products, whose health effects
are unknown. Encapsulation/microencapsulation provides an
effective means to enhance the oxidative stability of these oils.
The microencapsulation technology deals with packaging
solids, liquids or gaseous materials into miniature sealed
capsules that can release their contents at controlled rates
under specific conditions.42 The membrane of the capsules
protects the core material from undesirable effects of light,
moisture and oxygen, thus increasing the shelf-life of the
encapsulated products. Inspired by the rapidly growing nano-
technology, the food and drug industries have shown much
attention to the nanoencapsulation technique as an effective
and efficient means for the delivery of bioactive ingredients/
drugs and improvement of their stability. Enhanced oxidative
stability of encapsulated fats and oils has been reported.
4.2 Antioxidants
4.2.1 Antioxidant mechanisms. Among the many methods
employed for controlling lipid oxidation, use of antioxidants is
the most effective, convenient and economical means. Food
manufacturers world-wide use antioxidants to stabilize
food lipids and thus preventing quality deterioration of the
products. In the health-related areas antioxidants are used for
health promotion due to their ability to protect the body
against oxidative damage.
Antioxidants are substances that when present at low
concentrations compared to that of an oxidizable substrate
markedly delay or prevent its oxidation. Antioxidants that fit
in this definition include free radical scavengers, singlet oxygen
quenchers, inactivators of peroxides and other ROS, metal ion
chelators, quenchers of secondary oxidation products, and
4074 | Chem. Soc. Rev., 2010, 39, 4067–4079
View Article Online
inhibitors of pro-oxidative enzymes, among others. Anti-
oxidants may exert their inhibitory effect against oxidation
via different mechanisms and with varied activities. They may
be broadly classified based on their mode of action into
primary antioxidants which break the chain reaction of
oxidation by scavenging free radical intermediates, and
secondary antioxidants which prevent or retard oxidation by
suppression of oxidation initiator or accelerators or regeneration
of primary antioxidants.
Primary antioxidants such as most phenolic compounds are
able to neutralize free radicals by donating a hydrogen atom,
as shown below.
R + AH - RH + A
ROO + AH - ROOH + A
RO + AH - ROH + A
The resultant antioxidant radicals are stabilized by delocalization
of the unpaired electron around the phenol ring to form stable
resonance hybrids. These radicals have low reactivity and
generally do not initiate formation of new radicals, thus
breaking the chain-reaction of free radical propagation. Moreover,
the antioxidant radicals so formed can further scavenge free
radicals by participating in the termination of oxidation.
ROO + A - ROOA
RO + A - ROA
A + A - AA
Therefore, primary antioxidants can trap two lipid radicals by
donating a hydrogen atom to one radical and receiving an
electron from another radical to form stable non-radical
products.43
Secondary antioxidants prevent or retard oxidation by
several mechanisms. They exert their inhibitory effect by
suppressing the oxidation promoters, including metal ions,44
singlet oxygen,45 pro-oxidative enzymes46 and other oxidants.
Reducing agents can reduce lipid peroxides and related
oxidants through redox reactions, thus are also referred to
as oxygen scavengers. An example is thioethers, which convert
hydroperoxides into stable components in a non-radical
pathway.47 Metal ions are known to act as catalysts of
oxidation reaction, producing free radicals through electron
transfer, as shown below:
M(n+1)+ + RH - Mn+ + H+ + R
M(n+1)+ + ROOH - Mn+ + H+ + ROO
Mn+ + ROOH - M(n+1)+ + OH + RO
Metal chelators such as citric acid, phosphoric acid and
ethylenediaminetrtraacetic acid (EDTA) can decrease the
pro-oxidant effect of metal ions by forming a thermodynamically
stable complex and reducing their redox potentials.
Singlet oxygen quenchers such as carotenoids are able to
inactivate singlet oxygen by absorbing its excess energy and
This journal is 
c The Royal Society of Chemistry 2010

converting it to ground state triplet oxygen. The energy
absorbed is then released in the form of heat (scheme shown
below using b-carotene as an example).
1
O2 + b-carotene - 3b-carotene* + 3O2
3
b-carotene* - b-carotene + heat
Published on 09 July 2010. Downloaded by Lomonosov Moscow State University on 12/06/2013 14:59:58.
Therefore, the major mechanism of singlet oxygen inactivation
by carotenoids is physical quenching. Chemical quenching
may also take place when singlet oxygen reacts with the
electron-rich carotenoid molecules at the conjugated
double bonds to form the corresponding hydroperoxides.48
The ability of carotenoids to quench singlet oxygen is directly
dependent on the number of double bonds in the molecule.
One molecule of b-carotene, the predominant carotenoid in
many fruits and vegetables, consisting of 11 double bonds, is
able to quench up to 1000 molecules of singlet oxygen.49
Some secondary antioxidants can regenerate primary anti-
oxidants by replenishing hydrogen atom, thus inhibiting
depletion of important primary antioxidants. An example is
ascorbic acid, which can readily regenerate tocopherols from
their radicals and therefore act in a synergistic manner with
tocopherols in oxidation inhibition. Some other secondary
antioxidants catalyze decomposition of hydroperoxides into
non-radical species, or absorb UV radiation thus protecting
lipids from UV-induced photooxidation. An antioxidant may
protect against oxidation by one or a combination of different
mechanisms, as for multi-functional antioxidants. The
operative or dominant mechanism in a particular situation
determines to a great extent the kinetics and hence the activity
of the antioxidant.
The effectiveness of antioxidants is influenced by numerous
factors, including their structural features, concentration,
temperature, type of oxidation substrate and physical state of
the system as well as presence of pro-oxidants and synergists.
The chemical structure of an antioxidant determines its reactivity
towards free radicals and other ROS and hence its antioxidant
activity. The efficiency of antioxidants varies with their
concentration, necessitating the use of optimal concentrations
of antioxidants in order to achieve the greatest efficiency. It is
important to note that antioxidants may exhibit pro-oxidant
effects at higher concentrations.50 Antioxidant activity is also
affected by the system environment. For example, the
activity of antioxidants in bulk oils is different from that of
oil-in-water emulsions.51 In addition, antioxidants may offer
short-term or long-term protection against oxidation. This is
dependent on the reaction kinetics which involves the rate at
which an antioxidant reacts with a specific radical, the thermo-
dynamics and the extent that the reaction proceeds.
Table 5 Major antioxidants from natural sources
Antioxidants Example
Tocopherols a-, b-, g-, and d-tocopherols
Tocotrienols a-, b-, g-, and d-tocotrienols
Ascorbic acid Ascorbic acid, ascorbate
Carotenoids b-carotene, lycopene, astaxanthin, fucoxanthin
Phenolics Ferulic acid, quercetin, catechin, resveratrol, cyanidin
Peptides Ferritin, transferrin, lactoferrin
Enzymes Superoxide dismutase, catalase, glutathione peroxidase
This journal is 
c The Royal Society of Chemistry 2010
View Article Online
4.2.2 Sources of antioxidants. Antioxidant substances are
widely distributed in plant materials, animal tissues and
microorganisms, protecting the organisms from oxidative
stress and providing natural antioxidants to humans. Antiox-
idants can be isolated as pure compounds from natural sources
and used for food preservation, nutrition supplementation and
medicinal purposes. In addition, plant or animal extracts
containing a mixture of antioxidant substances are also used
directly to inhibit in vitro and in vivo oxidation. A large body
of research has been carried out in searching for antioxidant
sources and assessing their effectiveness and potential use in
different applications.
Higher plants and their constituents provide a rich source of
natural antioxidants. Fruits, vegetables, spices, herbs, cereals,
grains, oils, seeds, and teas are important sources of
plant-derived antioxidants, especially phenolic compounds,
including tocols. Antioxidants from marine origin such as
algae, fish/shellfish and marine bacteria, as well as products
derived from them such as protein hydrolysates, have recently
been of growing interest to researchers.52,53 A variety of
antioxidant constituents present in such resources have been
characterized and quantified. Among these are tocols, ascorbic
acid, carotenoids, polyphenols, antioxidant peptides and
enzymes (Table 5).
Tocols (Fig. 4) are fat-soluble antioxidants that are
extensively used to enhance the oxidative stability of foods.
Tocols are primary antioxidants that can effectively scavenge
lipid peroxyl radicals and produce a more stable tocopheroxyl
radical. The antioxidant activities of tocotrienols generally
exceeds those of their corresponding tocopherols. Tocols act
synergistically with ascorbic acid and phospholipids. Tocols
are distributed widely in plant tissues. The main sources of
natural tocopherols are soybean oil and other vegetable oils,
especially their deodourizer distillates during the oil
production, where individual tocopherols can be isolated.
Tocotrienols, less common than tocopherols, are present in
palm oil, rice bran oil and wheat germ oil, as well as
cereals and legumes.49 Purified or mixed tocols obtained as
value-added by-products during processing of vegetable oils
are used in the food and feed as well as pharmaceutical and
cosmetic applications.
Unlike tocols, ascorbic acid (vitamin C) (Fig. 5) is a water-
soluble antioxidant found primarily in fruits and vegetables.
Ascorbic acid exerts its antioxidant effect via multiple mechanisms,
including quenching various forms of oxygen, reduction of
free radicals and regeneration of primary antioxidants. The
effect of ascorbic acid on lipid stability is mainly due to its
synergistic interactions with other antioxidants. It shows
excellent synergism with a-tocopherol, citric acid, butylated
Source
Seeds, grains, nuts, vegetable oils, etc.
Palm oil, rice bran oil
Fruits, vegetables, etc.
Carrots, tomato, fish/shellfish, marine algae, etc.
Fruits, vegetables, nuts, cereals, etc.
Milk, egg, etc.
Plant and animal organisms
Chem. Soc. Rev., 2010, 39, 4067–4079 | 4075
 View Article Online
Published on 09 July 2010. Downloaded by Lomonosov Moscow State University on 12/06/2013 14:59:58.

Fig. 4 Chemical structures of tocopherols and tocotrienols.

hydroxyanisole (BHA), butylated hydrolxytoluene (BHT) and

Fig. 5 Chemical structure of ascorbic acid (vitamin C).
metal chelators. Ascorbic acid is susceptible to heat, light, pH,
oxygen, acrid smoke and water activity and often needs to be
replenished from exogenous sources. In biological systems,
ascorbic acid protects compounds in the water soluble
portions of cells and tissues and regenerates tocopherols at
the cellular membranes, hence playing a preventive role in a
number of human diseases. However, excessive ascorbic acid

Fig. 6 Chemical structures of some major carotenoids.

4076 | Chem. Soc. Rev., 2010, 39, 4067–4079 This journal is 

c The Royal Society of Chemistry 2010

may act as prooxidant by producing ferrous ion, an important
catalyst of oxidative damage.54
Carotenoids, including carotenes and xanthophylls, are
40-carbon isoprenoids (Fig. 6) that occur widely in plants,
fruits and vegetables as yellow, orange and red lipid-soluble
pigments. They are also minor components in many plant oils.
In addition to their provitamin A activity, carotenoids are
Published on 09 July 2010. Downloaded by Lomonosov Moscow State University on 12/06/2013 14:59:58.
important antioxidant nutrients against lipid oxidation and
oxidative stress both in in vitro and in vivo systems. They act
mainly as secondary antioxidants by quenching singlet
oxygen, as mentioned earlier, and may also prevent oxidation
by trapping free radicals. b-Carotene, lutein, lycopene and
isozeaxanthin are typical carotenoids that effectively retard
oxidation in foods. Astaxanthin has antioxidant activity that is
10 times greater than that of b-carotene, lutein, zeaxanthin
and canthaxanthin, and is often used in fish products.55
Phenolic compounds are another important group of anti-
oxidant naturally occurring, mainly in the plant kingdom.
The antioxidant activity of phenolic compounds arises from
their unique structures, which render a superior hydrogen
Fig. 7 Chemical structures of selected polyphenols (R groups are either H or OH, depending on the specific compound).
This journal is 
c The Royal Society of Chemistry 2010
View Article Online
donating capability over many other compounds. Phenolics,
including phenolic acids, stilbenes, flavonoids and lignans
(Fig. 7), act as free radical scavengers, metal chelators,
reducing agents and excellent synergists to other antioxidants,
and therefore showing great potential in inhibiting oxidation
in foods and biological systems. Various plant extracts
containing a broad array of phenolic compounds have
extensively been investigated for their composition, anti-
oxidant efficiency and potential application in the food,
cosmetic and pharmaceutical industries.
Proteins, protein hydrolysates, individual peptides and
amino acids have been shown to possess significant antioxidant
activities. However, in many cases, peptide fractions or protein
hydrolysates display greater antioxidant activity than intact
proteins or free amino acid mixtures, suggesting that peptides
play a major role in antioxidant action of proteins.
More recently, individual peptides responsible for antioxidant
activity of protein or protein hydrolysates have been separated
and identified.56 Protein digests have varied antioxidant
activities depending on the peptide structure, i.e. size of the
Chem. Soc. Rev., 2010, 39, 4067–4079 | 4077
 View Article Online
Published on 09 July 2010. Downloaded by Lomonosov Moscow State University on 12/06/2013 14:59:58.

Fig. 8 Chemical structures of common synthetic antioxidants; BHA, butylated hydroxyanisole; BHT, butylated hydroxytoluene; TBHQ, tert-
butylhydroquinone; and PG, propyl gallate.

peptides and their amino acid sequences, which are influenced PG propyl gallate
by the source of protein and conditions of hydrolysis process PI phosphatidylinositol
involved. There appears to be a relationship between PL phospholipids
the antioxidant properties of peptides and the presence of PS phosphatidylserine
aromatic, imidazole, sulfur-containing amino and imino acids. PUFA polyunsaturated fatty acids
The antioxidant mechanism (structure–activity relationship) ROS reactive oxygen species
of peptides is not yet fully understood. The radical scavenging RNS reactive nitrogen species
of aromatic amino acid-containing peptides is likely due to the SDS 1,2-distearoyl-3-docosaenoyl glycerol
hydrogen atom donor activity of the phenolic and indolic SOD superoxide dismutase
groups and higher stability of the phenoxyl and indolyl SSD 1,2-distearoyl-3-docosaenoyl glycerol
radicals than that of simple peroxyl radical.57 TAG triacylglycerols
Synthetic antioxidants were introduced to the food industry TBHQ tert-butylhydroquinone
in the 1940’s when BHA was found to retard oxidation and the
antioxidant effectiveness of several alkyl esters of gallic acid
was revealed. Common synthetic antioxidants currently used References
by the food industry include BHA, BHT, propyl gallate (PG) 1 H. D. Belitz, W. Grosch and P. Schieberle, Food Chemistry,
and tert-butylhydroquinone (TBHQ) (Fig. 8). However, use of Springer-Verlag, New York, NY, 3rd revised edn, 2004.
synthetic antioxidants is now limited owing to the growing 2 F. Shahidi and V. K. S. Shukla, Inform., 1996, 7, 1227.
3 R. G. Ackman, in Bailey’s Industrial Oil and Fat Products,
concern over their potential carcinogenic effects.58 Use of these ed. F. Shahidi, John Wiley & Sons, Inc., Hoboken, NJ, 6th edn,
antioxidants is subject to regulations that vary from country to 2005, vol. 3, pp. 279–318.
country. 4 F. Shahidi and Y. Zhong, in Bailey’s Industrial Oil and Fat
Products, ed. F. Shahidi, John Wiley & Sons, Inc., Hoboken,
NJ, 6th edn, 2005a, vol. 3, pp. 259–278.
Abbreviations 5 F. Shahidi, in Marine Nutraceuticals and Functional Foods, ed.
C. Barrow and F. Shahidi, Taylor & Francis Group, LLC, Boca
BHA butylated hydroxyanisole Raton, FL, 2007, pp. 23–62.
BHT butylated hydrolxytoluene 6 D. M. Klurfeld, in Food Lipids, ed. C. C. Akoh and D. B. Min,
Marcel Dekker, Inc., New York, NY, 6th edn, 2002, pp. 589–602.
DAG diacylglyerols 7 Omega-3 fatty acids: chemistry, nutrition and health effects,
DHA docosahexaenoic acid ACS Symposium Series 788, ed. F. Shahidi and J. Finley,
DPA docosapentaenoic acid American Chemical Society, Washington, DC, 2001.
8 F. Shahidi and H. Miraliakbari, J. Med. Food, 2004, 7, 387.
EDTA ethylenediaminetrtraacetic acid 9 F. Shahidi and H. Miraliakbari, J. Med. Food, 2005, 8, 133.
EFA essential fatty acids 10 F. Shahidi and H. Miraliakbari, in Nutraceutical and specialty
EPA eicosapentaenoic acid lipids and their co-products, ed. F. Shahidi, Taylor & Francis
GL glycolipids Group, LLC, Boca Raton, FL, 2006, pp. 227–250.
11 M. U. Jakobsen, K. Overvad, J. Dyerberg, M. Schroll and
LDL low density lipoprotein B. L. Heitmann, Am. J. Epidemiol., 2004, 160, 141.
MAG monoacylglycerols 12 M. Crupkin and A. Zambelli, Compr. Rev. Food Sci. Food Saf.,
MBI methylene bridge index 2008, 7, 271.
NO nitric oxide 13 J. M. deMan, Principles of Food Chemistry, Aspen Publishers, Inc.,
Gaithersburg, Marryland, 3rd edn, 1999, pp. 33–110.
PC phosphatidylcholine 14 F. Hamam and F. Shahidi, Food Chem., 2005, 91, 583.
PE phosphatidylethanolamine 15 F. Hamam and F. Shahidi, J. Agric. Food Chem., 2006, 54, 4390.

4078 | Chem. Soc. Rev., 2010, 39, 4067–4079 This journal is 

c The Royal Society of Chemistry 2010

16 S. P. J. N. Senanayake and F. Shahidi, in Bailey’s Industrial Oil and
Fat Products, ed. F. Shahidi, John Wiley & Sons, Inc., Hoboken,
NJ, 6th edn, 2005, vol. 3, pp. 555–584.
17 K. B. Beckman and B. N. Ames, Physiol. Rev., 1998, 78, 547.
18 L. Kruidenier and H. W. Verspaget, Aliment. Pharmacol. Ther.,
2002, 16, 1997.
19 T. P. Dalton, H. G. Shertzer and A. Puga, Annu. Rev. Pharmacol.
Toxicol., 1999, 39, 67.
20 K. J. Davies, IUBMB Life, 2000, 50, 279.
Published on 09 July 2010. Downloaded by Lomonosov Moscow State University on 12/06/2013 14:59:58.
21 R. A. Floyd and K. Hensley, Neurobiol. Aging, 2002, 23, 795.
22 K. M. Schaich, in Bailey’s Industrial Oil and Fat Products,
ed. F. Shahidi, John Wiley & Sons, Inc., Hoboken, NJ, 6th edn,
2005, vol. 1, pp. 269–356.
23 G. Ohloff, in Functional Properties of Fats in Foods, ed. J. Solms,
Forster Publishing, Zurich, Switzerland, 1973.
24 F. Shahidi and Y. Zhong, in Bailey’s Industrial Oil and Fat
Products, ed. F. Shahidi, John Wiley & Sons, Inc., Hoboken,
NJ, 6th edn, 2005b, vol. 1, pp. 357–386.
25 R. Hiatt, T. Mill, K. C. Irwin, T. R. Mayo, C. W. Gould and
J. K. Castleman, J. Org. Chem., 1968, 33, 1416.
26 M. C. Erickson, in Food Lipids, ed. C. C. Akoh and D. B. Min,
Marcel Dekker, Inc., New York, NY, 2002, pp. 365–412.
27 F. Shahidi and U. N. Wanasundara, in Food Lipids, ed. C. C. Akoh
and D. B. Min, Marcel Dekker, Inc., New York, NY, 2002,
pp. 465–487.
28 L. Lyras, N. J. Cairns, A. Jenner and P. Jenner, Neurochemistry,
1997, 68, 2061.
29 D. B. Min and J. M. Boff, in Food Lipids, ed. C. C. Akoh and
D. B. Min, Marcel Dekker, Inc., New York, NY, 2002a,
pp. 335–364.
30 F. D. Gunstone, Vegetable Oils in Food Technology: Composition,
Properties and Uses, CRC Press, Boca Raton, FL, 2002.
31 Z. Shen and C. Wijesundera, J. Food Lipids, 2009, 16, 62.
32 C. Wijesundera, Lipid Technol., 2008, 20, 199.
33 W. W. Nawar, in Food Storage Stability, ed. I. A. Taub and
R. P. Singh, CRC Press, 1997, pp. 89–104.
34 J. Pikul and F. A. Kummerow, J. Food Sci., 1990, 55, 1243.
35 M. C. Yin and C. Faustman, J. Agric. Food Chem., 1993, 41, 853.
36 M. A. Khan and F. Shahidi, J. Food Lipids, 2000, 7, 143.
This journal is 
c The Royal Society of Chemistry 2010
View Article Online
37 F. Shahidi, Metusalach and J. A. Brown, Crit. Rev. Food Sci.
Nutr., 1998, 38, 1.
38 M. A. Khan and F. Shahidi, Food Chem., 2002, 79, 47.
39 R. Abuzaytoun and F. Shahidi, J. Am. Oil Chem. Soc., 2006, 83,
855.
40 R. A. Floyd and K. Hensley, Neurobiol. Aging, 2002, 23, 795.
41 L. Tylicki, B. Rutkowski and W. H. Horl, Kidney Blood Pressure
Res., 2003, 26, 303.
42 R. B. Pegg and F. Shahidi, in Handbook of Food Preservation,
ed. M. S. Rahman, Taylor & Francis Group, LLC, Boca Raton,
FL, 2007, pp. 509–570.
43 I. S. Young and I. S. Woodside, J. Clin. Pathol., 2001, 54, 176.
44 M. Leopoldini, N. Russo, S. Chiodo and M. Toscano, J. Agric.
Food Chem., 2006, 54, 6343.
45 D. B. Min and J. M. Boff, Compr. Res. Food Csci. Food Safety,
2002, 1, 56.
46 G. F. Sud’ina, O. K. Mirzoeva, M. A. Pushkareva,
G. A. Korshunova, N. V. Sumbatyan and S. D. Varfolomeev,
FEBS Lett., 1993, 329, 21.
47 J. Pokorny, Eur. J. Lipid Sci. Technol., 2007, 109, 629.
48 P. Racine and B. Auffray, Fitoterapia, 2005, 76, 316.
49 D. W. Reische, D. A. Lillard and R. R. Eitenmiller, in Food Lipids,
ed. C. C. Akoh and D. B. Min, Marcel Dekker Inc., New York,
NY, 2002, pp. 489–516.
50 J. Cillard and P. Cillard, J. Am. Oil Chem. Soc., 1986, 63, 1165.
51 W. L. Porter, Toxicol. Ind. Health, 1993, 9, 93.
52 S. K. Kim, Y. T. Kim, H. G. Byun, K. S. Nam, D. S. Joo and
F. Shahidi, J. Agric. Food Chem., 2001, 49, 1984.
53 Y. Athukorala, K. W. Lee, C. Song, C. B. Ahn, T. S. Shin,
Y. J. Cha, F. Shahidi and Y. J. Jeon, J. Food Lipids, 2003, 10, 251.
54 C. Kaur and H. C. Kapoor, Int. J. Food Sci. Technol., 2001, 36,
703.
55 K. Mikova, in Antioxidants in Food: Practical Applications, ed.
J. Pokorny, N. Yanishlieva and M. Gordon, Woodhead Publishing
Ltd., Cambridge, England, 2001, pp. 267–283.
56 F. Shahidi and Y. Zhong, J. AOAC Int., 2008, 91, 914.
57 A. Pihlanto, Int. Dairy J., 2006, 16, 1306.
58 E. R. Sherwin, in Food Additives, ed. L. Branen, Marcel Dekker,
New York, NY, 1990, pp. 139–193.
Chem. Soc. Rev., 2010, 39, 4067–4079 | 4079