Natural Antioxidants: Sources, Compounds,

Mechanisms of Action, and Potential Applications

M.S. Brewer

Abstract: While use of synthetic antioxidants (such as butylated hydroxytoluene and butylated hydroxyanisole) to
maintain the quality of ready-to-eat food products has become commonplace, consumer concern regarding their safety
has motivated the food industry to seek natural alternatives. Phenolic antioxidants can inhibit free radical formation and/or
interrupt propagation of autoxidation. Fat-soluble vitamin E (α-tocopherol) and water-soluble vitamin C (L-ascorbic
acid) are both effective in the appropriate matrix. Plant extracts, generally used for their flavoring characteristics, often
have strong H-donating activity thus making them extremely effective antioxidants. This antioxidant activity is most
often due to phenolic acids (gallic, protocatechuic, caffeic, and rosmarinic acids), phenolic diterpenes (carnosol, carnosic
acid, rosmanol, and rosmadial), flavonoids (quercetin, catechin, naringenin, and kaempferol), and volatile oils (eugenol,
carvacrol, thymol, and menthol). Some plant pigments (anthocyanin and anthocyanidin) can chelate metals and donate H
to oxygen radicals thus slowing oxidation via 2 mechanisms. Tea and extracts of grape seeds and skins contain catechins,
epicatechins, phenolic acids, proanthocyanidins, and resveratrol, all of which contribute to their antioxidative activity.
The objective of this article is to provide an overview of natural antioxidants, their mechanisms of action, and potential
applications.

Introduction
Ultimately, food quality is defined in terms of consumer ac-
ceptability: taste, aroma, and appearance characteristics. The in-
creasing demand for convenient foods has led to rapid growth in
the ready-to-eat product category (Hofstrand 2008). Many of the
food ingredients contain unsaturated fatty acids that are quite sus-
ceptible to quality deterioration, especially under oxidative stress.
For this reason, efforts to reduce oxidation have increased. Most
often, the best strategy is the addition of antioxidants.
Synthetic phenolic antioxidants (butylated hydroxyanisole
[BHA], butylated hydroxytoluene [BHT], and propyl gallate)
effectively inhibit oxidation; chelating agents, such as ethylene
diamine tetra acetic acid (EDTA), can bind metals reducing their
contribution to the process. Some vitamins (ascorbic acid [AA] and
α-tocopherol), many herbs and spices (rosemary, thyme, oregano,
sage, basil, pepper, clove, cinnamon, and nutmeg), and plant ex-
tracts (tea and grapeseed) contain antioxidant components as well
(Hinneburg and others 2006). Natural phenolic antioxidants, such
as synthetics, can effectively scavenge free radicals, absorb light in
the ultraviolet (UV) region (100 to 400 nm), and chelate tran-
sition metals, thus stopping progressive autoxidative damage and
production of off-odors and off-tastes.
MS 20101442 Submitted 10/22/2010, Accepted 3/8/2011. Author is with the
Dept. of Food Science and Human Nutrition, 202 ABL, 1302 W. Pennsylvania
Ave., Univ. of Illinois, Urbana, IL 61801, U.S.A. Direct inquiries to author Brewer
(E-mail: msbrewer@uiuc.edu).
Since 1994, consumers have expressed concern about the safety
of preservatives and additives in their food (Brewer and Russon
1994; Brewer and Prestat 2002; Rojas and Brewer 2008b). More
than 12 y ago, Sloan (1999) reported that one of the top 10 trends
for the food industry to watch included the sales of natural, or-
ganic, and vegetarian foods. There is a clear trend in consumer
preference for clean labeling (Hillmann 2010), for food ingre-
dients and additives that are organic/natural with names that are
familiar, and that are perceived to be healthy (Joppen 2006). In ad-
dition, the call for sustainable sources and environmentally friendly
production is forcing the food industry to move in that direction
(Berger 2009).
Defrancesco and Trestini (2008) estimated that consumers were
willing to pay a price premium (up to 70% more) for organic
fresh produce (tomatoes) for their health-promoting antioxidant
content. Of an estimated $17 billion in sales in the United States,
organic foods account for only 3% of total retail food sales. This
category has been growing at 7 times the rate of the average
food category and has maintained a growth rate of more than 15%
per year. However, based on the results of a recent study, Evans and
others (2010) concluded that products with physical changes, less
processing, with identifiable ingredients would also be perceived
to be more natural.
Consumer expectations about ingredients that may suitably be
labeled as “natural” do not always coincide with current guidelines
(Williams and others 2009). A clear definition can guide manufac-
turers. However, the lack of consumer consensus makes it difficult
for them to understand the implications. For consumers, “natural”

c 2011 Institute of Food Technologists®


doi: 10.1111/j.1541-4337.2011.00156.x Vol. 10, 2011 r Comprehensive Reviews in Food Science and Food Safety 221
Natural antioxidants . . .

and “clean label” are related to what they perceive an ingredient Table 1–Flavors and aromas associated with volatile compounds resulting
to be. from lipid oxidation.
This article provides an overview of naturally occurring an- Compound Flavors and aromas
tioxidant compounds, their sources, and mechanisms of action. Butanoic acid Rancid
Various different mechanisms may contribute to oxidative pro- Propanoic acid Pungent, rancid, soy
cesses in complex systems, such as foods. These include reactions Pentanal Pungent, malt
Hexanal Green, grassy, tallowy
that generate reactive oxygen species that target different struc- Heptanal Green, oily, rancid
tures (lipids, proteins, and carbohydrates), and Fenton reactions, Octanal Sweet, fatty, soapy
where transition metal ions play a vital role. It should be noted Nonanal Tallowy, waxy
Decanal Rancid, burnt
that antioxidant activity of food extracts can be determined using a Decanal Soapy, tallowy
variety of tests (stable free radical scavengers: galvinoxyl, diphenyl- 2-Nonenal Paper
b-picrylhydrazyl [DPPH]; lipid oxidation: peroxide oxygen, con- 2-Hexenal Rancid
jugated dienes, Rancimat [measurements of oxygen consumption Nona-2(E)-enal Tallowy, fatty
E-2-Hexenal Green, fat, rancid
of a linoleic acid emulsion and oxidation induction period in lard E-2-Octenal Fatty, nutty, green
at 100 ◦ C], oxygen radical absorbance capacity [ORAC] values ), E-2-Decenal Green, pungent,
active oxygen method, iodine value (measure of the change in E,E-Deca-2, 4-dienal Fatty, fried potato, green
E,E-Nona-2, 4-dienal Green, grassy, fatty
number of double bonds that bind I), anisidine value (reaction of 2-Propanone Livery
acetic acid p-anisidine and aldehydes to produce a yellow color 3-Hydroxy-2-butanone Rancid, beany, grassy
that absorbs at 350 nm), measurement of absorbance at 234 nm 2,3-Octanedione Oxidized fat or oil
Nonenone Pungent
(conjugated dienes) and 268 nm (conjugated trienes) to assess oxi- 2-Heptanone Soapy
dation in the early stages, and chromatographic methods; however, Dimethyl disulfide Onion, cabbage, putrid
Dimethyl trisulfide Sulfur, fish, cabbage
extraction procedures strongly influence the composition of the Methanethiol Garlic, sulfur
extracts and, therefore, also influence the antioxidant activity re-
Kerler and Grosch (1996), Yong and others (2000), Ahn and others (2002, 2007), Jensen and others
sults (Halliwell 1997; Schwarz and others 2001; Trojakova and (2002), Jo and others (2003), Mahrour and others (2003), Nam and Ahn (2003), Nam and others
(2003), Acree and Arn (2004), Rochat and Chaintreau (2005), Obana and others (2006), and Yancey
others 2001). In addition, the effect of the antioxidant compound and others (2006).
in a food matrix may be significantly different than the activity of
a purified extract.
primary products of lipid oxidation. They are tasteless and odor-
Food Lipids less; however, in the presence of heat, metal ions, and/or light, they
The fatty acids in the lipids of food tissues may be saturated or can decompose to compounds r that contribute roff-odors and off-
unsaturated and may be part of the neutral triglyceride fraction tastes. Alkoxy radicals (RO ) can also abstract H from unsaturated
(triacylglycerol) or part of the phospholipid fraction. Free fatty fatty acids continuing the chain reaction (see nr 5 below; r Decker
acids are electron-deficient at the oxygen atom of the carbonyl 2002; Srinivasan and others 2008). Hydroxyl radicals ( OH) can
group (C=O); unsaturated fatty acids are also electron-deficient react with conjugated systems continuing the oxidation process.
at points of carbon–carbon unsaturation (C=C). These electron- This chain reaction terminates when 2 radical species combine to
deficient regions make fatty acids susceptible to attack by a vari- form a nonradical species (see nr 6 below). Antioxidants (A:H) r
ety of oxidizing and high-energy agents generating free radicals inhibit the chain reaction by donating hydrogen atoms (H ) to
(Nawar 1996). Triglycerides contain straight chains of primarily radicals (see nr 7 below). The antioxidant free radical may then
16- to 18-carbon fatty acids and minimal amounts of unsaturated form a stable peroxy-antioxidant compound (see nr 8 below).
fatty acids. Phospholipids in tissue membranes contain up to 15 r r
times the amount of unsaturated fatty acids (C18:4, C20:4, C20:5,
(1) R:H r → R + HOO
r + O::O + Initiator
(2) R + rO::O → ROO r
C22:5, and C22:6) found in triglycerides. They are much more (3) ROO + R:H →
susceptible to oxidation because of the increase in the number of r ROOH r +R
(4) RO:OHr→ RO + HO r
points of carbon–carbon unsaturation (C=C) (Elmore and others (5) R::R +r OH → R:R-O
1999). r
(6) Rr + R →r R:R
(7) R + rROO → rROOR
Oxidation r (8) ROOr + ROO → ROOR +r O2
When a hydrogen atom (H ) is abstracted rfrom an unsaturated
fatty acid (R:H) forming an alkyl radical (R ), lipid oxidation is
(9) ROOr + AHr → ROOH + A
(10) ROO + A → ROOA.
initiated (see nr 1 below). Generation of this lipid radical is ther-
modynamically unfavorable and ris usually initiated by the presence Ultimately, oxidation depends on the addition of oxygen to a
of other radical compounds (R ), singletstate oxygen (1 O2 ), de- compound; however, the energy level of the oxygen has a sig-
composition of hydroperoxides (ROOH), or pigments that r act as nificant impact on the ease of the oxidation reaction. Singlet
photoensitizers. In order to stabilize, the alkyl radical (R ) usually state oxygen (1 O2 ) has spin-coupled electrons and is a nonrad-
undergoes a shift in the position of the double bond (cis r to trans) ical, high-energy species (Decker 2002; Min and Boff 2002). It is
and production of a conjugated diene system. The R r can react electrophilic and can react with other electron-rich, nonradical,
with O2 to form a high-energy peroxyl radical (ROO ; see nr 2 singlet state compounds containing double bonds (C=C, C=O).
below).
r The peroxyl radical can then abstract a hydrogen atom However, oxygen in its lowest energy state, triplet state oxygen
(H ) from another unsaturated fatty acid (see nr 3 below) forming
r (3 O2 ), has 2 unpaired, parallel spin electrons. It is very reactive
a hydroperoxide (ROOH) and a new, free alkyl radical (R ). This (primarily with radical species). Most food components, such as
process then propagates to another fatty acid (see nr 4 below; Srini- carbohydrates and proteins, are nonradical (singlet state) and are
vasan and others 2008). Lipid hydroperoxides (ROOH) are the relatively unreactive with triplet state oxygen (3 O2 ); however, they

222 Comprehensive Reviews in Food Science and Food Safety r Vol. 10, 2011 c 2011 Institute of Food Technologists®

Natural antioxidants . . .

are reactive with singlet state oxygen (1 O2 ) that can be generated Table 2–Total ORAC values (μm TE/100 g; Prior and others 2003) of
in response to temperature change, reduction of activation en- selected herbs and spices, berries, roots, and teas.
ergy (presence of transition metals), exposure to UV light, and Food Total ORAC SEM
physical damage to tissues. Singlet oxygen and free radicals can Basil (fresh) 4805 225
cause biological damage to macromolecules and membrane con- Marjoram (fresh) 27297 1306
stituents. The presence of natural antioxidants may help control Oregano (fresh) 13970 545
these degradative reactions. Sage (fresh) 32004 1548
Savory (fresh) 9465 436
Oxidation of unsaturated fatty acids can produce a variety of Basil (dried) 61063 2280
aldehydes, alkanals, alkenes, and alkanes; many of which con- Cinnamon (ground) 131420 13867
tribute off-odors that are perceptible at very low concentrations. Clove (ground) 290283 3292
Ginger (ground) 39041 1835
Odor detection thresholds for pentanal, hexanal, and heptanal, Nutmeg (ground) 69640 6859
compounds typically generated from the breakdown of oxidized Oregano (dried) 175295 7683
linoleic acid have been reported to be <34, <38, and 62 ppb, re- Pepper, black 34053 289
Rosemary (dried) 165280 1391
spectively, in a gelatin model system (Vega and Brewer 1995). The Sage (ground) 119929 20305
odors of a variety of oxidation-generated compounds are shown Thyme (fresh) 27426 1251
in Table 1. Thyme (dried) 157380 1629
Turmeric (ground) 127068 11181
Grapes (red, raw) 1837 248
Raspberries (raw) 5065 205
Antioxidants Garlic (raw) 5708 475
Antioxidants are compounds or systems that delay autoxidation Ginger root (raw) 14840 530
Onions, red (raw) 1521 69
by inhibiting formation of free radicals or by interrupting propaga- Tea brewed 1128 −
tion of the free radical by one (or more) of several mechanisms: (1) Tea, green, brewed 1253 −
scavenging species that initiate peroxidation, (2) chelating metal The oxygen radical absorbance capacity (ORAC) method is based on the inhibition of the
peroxyl-radical-induced oxidation initiated by thermal decomposition of azo compounds. Prior and
ions such that they are unable to generater reactive species or de- others (2003) used 2,2 -azo bis (2 amidino propane) dihydrochloride (AAPH) as the azo generator,
compose lipid peroxides, (3) quenching O2 − preventing forma- incubated at 37 ◦ C for 30 min with fluorescein (14 μm) as a fluorescent detector.
Source: USDA (2010).
tion of peroxides, (4) breaking the autoxidative chain reaction,
and/or (5) reducing localized O2 concentrations (Nawar 1996).
Chain-breaking antioxidants differ in their antioxidative effec-
tiveness depending on their chemical characteristics and physical
Natural Antioxidants
location within a food (proximity to membrane phospholipids,
Food tissues, because they are (or were) living, are under con-
emulsion interfaces, or in the aqueous phase). The chemical po-
stant oxidative stress from free radicals, reactive oxygen species,
tency of an antioxidant and solubility in oil influence its acces-
and prooxidants generated both exogenously (heat and light) and
sibility to peroxy radicals especially in membrane, micellar and
endogenously (H2 O2 and transition metals). For this reason, many
emulsion systems, and the amphiphilic character required for ef-
of these tissues have developed antioxidant systems to control free
fectiveness in these systems (Wanatabe and others 2010).
radicals, lipid oxidation catalysts, oxidation intermediates, and sec-
Antioxidant effectiveness is related to activation energy, rate
ondary breakdown products (Nakatani 2003; Agati and others
constants, oxidation–reduction potential, ease with which the an-
2007; Brown and Kelly 2007; Chen 2008; Iacopini and others
tioxidant is lost or destroyed (volatility and heat susceptibility),
2008). These antioxidant compounds include flavonoids, pheno-
and antioxidant solubility (Nawar 1996). In addition, inhibitor
lic acids, carotenoids, and tocopherols that can inhibit Fe3+ /AA-
and chain propagation reactions are both exothermic. As the
induced oxidation, scavenge free radicals, and act as reductants
A:H and R:H bond dissociation energies increase, the activation
(Khanduja 2003; Ozsoy and others 2009).
increases and the antioxidant efficiency decreases. Conversely, as
Spices and herbs, used in foods for their flavor and in medicinal
these bond energies decrease, the antioxidant efficiency increases.
mixtures for their physiological effects, often contain high con-
The most effective antioxidants are those that interrupt the free
centrations of phenolic compounds that have strong H-donating
radical chain reaction. Usually containing
r aromatic or phenolic
activity (Lugasi and others 1995; Muchuweti and others 2007).
rings, these antioxidants donate H to the free radicals formed
during oxidation becoming a radical themselves (see step nr 7).
These radical intermediates are stabilized by the resonance delo- Table 3– Content of redox-active compounds (antioxidants) of selected
calization of the electron within the aromatic ring and formation of foods (mmol/100 g).
quinone structures (Nawar 1996). In addition, many of the phe-
Redox-active compound
nolics lack positions suitable for molecular oxygen attack. Both Food content (mmol/100 g)
synthetic antioxidants (BHA, BHT, and propyl gallate) and natural
Cloves, ground 125.5
botanicals contain phenolics (flavonoids) function in this manner. Oregano leaf, dried 40.3
Botanical extracts with antioxidant activity generally quench free Ginger, ground 21.6
radical oxygen with phenolic compounds as well. Cinnamon, ground 17.7
Turmeric powder 15.7
Because bivalent transition metal ions, Fe2+ in particular, can Basil leaf, dried 12.3
catalyze oxidative processes, leading to formation of hydroxyl rad- Curry powder 10.0
icals, and can decompose hydroperoxides via Fenton reactions, Paprika 8.6
Pepper, black 4.4
chelating these metals can effectively reduce oxidation (Halliwell Raspberries 2.3
and others 1987). Food materials containing significant amounts Wine, red 2.1
of these transition metals (red meat) can be particularly susceptible Cherries, sour 1.8
to metal-catalyzed reactions. Sources: McCormick Institute Antioxidant Comparison (2009) and Halvorsen and others (2006).

c 2011 Institute of Food Technologists®

 Vol. 10, 2011 r Comprehensive Reviews in Food Science and Food Safety 223
Natural antioxidants . . .

O OH Figure 1–Antioxidative phenolic acids (gallic,

protochatechuic, p-coumaric acid, caffeic, and
rosmarinic) found in plant extracts. All
O OH
structures generated using ChemBioOffice
COOH
(2008).

HO OH HO

OH OH OH

Gallic acid Protocatechuic acid p-Coumaric acid

OH

OH

HO

O OH
O O

HO HO

OH OH

Caffeic acid Rosmarinic acid

Many also have high ORAC values (Table 2 and 3). Some plant-
derived compounds (carnosol, rosmanol, rosmariquinone, and
rosmaridiphenol) are better antioxidants than BHA (Richheimer
and others 1996; Carvalho and others 2005).
The major antioxidative plant phenolics can be divided into
4 general groups: phenolic acids (gallic, protochatechuic, caffeic,
and rosmarinic acids; Figure 1), phenolic diterpenes (carnosol
and carnosic acid; Figure 2), flavonoids (quercetin and catechin;
Figure 3), and volatile oils (eugenol, carvacrol, thymol, and men-
thol; Figure 4; Shan and others 2005). Phenolic acids generally
act as antioxidants by trapping free radicals; flavonoids can scav-
enge free radicals and chelate metals as well (Engeseth and Geldof
2001).
The common characteristic of the flavonoids (flavones,
flavonols, flavanols, and flavanones) is the basic 15-carbon flavan
structure (C6 C3 C6 ; Figure 5). These carbon atoms are arranged
in 3 rings (A, B, and C). Classes of flavonoids differ in the level of
saturation of the C ring. Individual compounds within a class dif-
fer in the substitution pattern of the A and B rings that influence
the phenoxyl radical stability and the antioxidant properties of the
substances (Wojdyło and others 2007).
The free radical-scavenging potential of natural polyphenolic
compounds appears to depend on the pattern (both number and
location) of free −OH groups on the flavonoid skeleton (Lupea
and others 2008). The B-ring substitution pattern is especially
important to free radical-scavenging ability of flavonols. Study-
ing the ability of 4 flavonols substituted at different points on the
B-ring (galangin, kaempferol, quercetin, and myricetin) to quench
the intrinsic fluorescence of bovine serum albumen, Xiao and
others (2008) found that myricetin > quercetin > kaempferol >
galangin. Authors interpret these findings as indicating that hy-
drogen bond force plays an important role.
Flavonoids with multiple hydroxyl groups are more effective
antioxidants than those with only one. The presence of the ortho-
3,4-dihydroxy structure increases the antioxidative activity (Geldof
and Engeseth 2002). Flavonoids can dampen transition metal

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Natural antioxidants . . .

CH3 CH 3 Figure 2–Antioxidative phenolic diterpenes

H 3C CH3 (carnosol, carnosic acid, rosmanol, and
rosmarinic acid) found in plants.
OH

CH 3
Diterpene structure

OH
H
O
HO

O
COOH

OH

OH
OH

Carnosol Carnosic acid

OH

OH

HO

O O
OH CH 3

HO
CH3

O CH

OCH 2CH 3 HO

H 3C CH3 OH

Rosmanol Rosmarinic acid

r
enhancement of oxidation by donating a H to them, rendering
them less proxidative. In addition, flavones and some flavanones
(naringenin) can preferentially bind metals at the 5-hydroxyl and
4-oxo groups (Fernandez and others 2002).
Brown and Kelly (2007) evaluated the antioxidative activity of
structurally related (poly)phenols, anthocyan(id)ins, and phenolic
acids at physiologically relevant concentrations (100 to 1000 nM)
using a Cu2+ -mediated low-density lipoprotein oxidation model.
(Poly)phenols with an ortho-dihydroxy substituted arrange-
ment (cyanidin-3-glucoside, cyanidin, and protocatechuic acid)
were the most effective, while trihydroxy-substituted compounds
(gallic acid) had only intermediate efficacy. This was explained, in
part, by their ability to chelate Cu2+ ions. It seems likely that the
steric relationship of these −OH groups and their arrangement on
the ring(s) both play a role in the ability of the substance to chelate
metal ions. However, differences in lipid/hydrophilic phase parti-
tioning and in H-donating abilities were also hypothesized to have
contributed to the structure-activity relationships.
Alamed and others (2009) reported that the order of free radical-
scavenging activity of a group of polar compounds was ferulic
acid > coumaric acid > propyl gallate > gallic acid > AA; the
free radical-scavenging activity of a group of nonpolar compounds
was rosmarinic acid > BHT, tert-butylhydroquinone (TBHQ) >
α-tocopherol. Only propyl gallate, TBHQ, gallic acid, and
rosmarinic acid inhibited lipid oxidation in an oil-in-water emul-
sion that may reflect the ability of these compounds to orient at
the interface of the oil droplet in the emulsion.
Evaluating the antioxidative activity of hydroxycinnamic acids
with similar structures (caffeic, chlorogenic, o-coumaric, and
ferulic acids) in a fish muscle system, Medina and others (2007)
found that the capacity of these compounds to donate electrons
(bond dissociation energies) appeared to play the most significant

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 Vol. 10, 2011 r Comprehensive Reviews in Food Science and Food Safety 225
Natural antioxidants . . .

OH
OH
OH
OH

HO O
HO O

OH OH

OH OH O

Epicatechin Quercetin (flavanol)

OH
OH

HO
OH

O OH
HO O
HO
OH

O
HO O

HO OH
OH
O
O

HO
OH

OH
OH

Epicatechin gallate Epigallocatechin gallate

OH

HO

O O OH

HO
O OH
O

HO

OH O O

HO OH

Rutin OH

Figure 3–Antioxidative flavonoids (epicatechin, quercetin, epicatechin gallate, epigallocatechin gallate, and rutin) found in plant extracts.

226 Comprehensive Reviews in Food Science and Food Safety r Vol. 10, 2011 c 2011 Institute of Food Technologists®

Natural antioxidants . . .

OH 3C
O

HO

HO O

Eugenol Carvacrol Safrole

H 3C
O

O
OH OH

O
H2 C

Thymol Menthol Myristicin

OH H 3C CH 3 O

CH3
H3 C

CH 3 CH3

1,8-Cineol - Terpineol p-Cymene Cinnamaldehyde

O
N

Piperine

Figure 4–Antioxidant volatile oils (eugenol, carvacrol, safrole, thymol, menthol, 1,8-cineole, α-terpineol, p-cymene, cinnamaldehyde, myristicin, and
piperine) found in plant extracts.

role in delaying rancidity, while the ability to chelate metals and
the distribution between oily and aqueous phases were not cor-
related with inhibitory activities. The latter finding may reflect
the type of matrix, fish muscle, in which the oxidative activity
was studied. Caffeic acid was the most effective of this antioxidant
group (similar to propyl gallate).
Potapovich and Kostyuk (2003) reported that, of a variety of
flavonoids (rutin, dihydroquercetin, quercetin, epigallocatechin
gallate, and epicatechin gallate), the catechins were most
effective in inhibiting microsomal lipid peroxidation. All rwere
able to chelate Fe2+ , Fe3+ , and Cu2+ and were effective O2 −
scavengers to varying degrees. Authors speculate that the

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Natural antioxidants . . .

B
8
7 9
A
6 4 2
5 3 1

Basic C6, C3, C6 structure Chalcone

B B B
HO O O O

A C A C A C

OH

OH O O O

Flavone Flavonol Flavanone

HO

R1
O OH

3' R2
4'
+ O O
R7 O 5' OH
7 R3 HO O
O

6 3
HO OH
R6 5 R4
HO OH
OH
R5 OH

Anthocyanin (R2= -OH, R4= -OH Anthocyanidin-3,5-glucoside

or H, R5 and R7= -OH or –OCH3

Figure 5–Flavonoid structure and flavonoids (flavanones: chalcone, flavone, flavanol, and flavanones; and flavans: anthocyanin and
anthocyanidin-3,5-glycoside) found in plant extracts.

r
relative ability to scavenge O2 − may be responsible for the relative
antioxidative difference among these compounds.
Many of the antioxidative flavonoid compounds are naturally
occurring pigments. It appears that chloroplast-located
r flavonoids
perform a photo-protective role against O2 − in plants (Agati and
others 2007). Anthocyanins are the glycosides of polyhydroxy or
polymethoxy derivatives of the flavylium cation. Hydrolysis of
the sugar moiety yields an aglycone, anthocyanindin (Figure 5).
Anthocyanins and anthocyanindins exhibit visual color because
of the extreme mobility of the electrons within the molecular
structure (double bonds) in response to light in the visible spectrum
(approximately 400 to 700 nm). The pigments are quite water-
soluble and 4 −OH groups are bound to the aromatic rings. pH
has a significant effect on anthocyanin pigments.r These −OH
groups can give
r up H+ (in a basic solution) or H to an oxidizing
lipid (ROO ).
Proanthocyanidins also contain
r multiple −OH groups that can
donate hydrogen, quench O2 − , and chelate metals (Shahidi and
Wanasundara 1992; Fukumoto and Mazza 2000). Free radical-
scavenging ability increases as the number of phenolic −OH
groups increases (Kondo and others 2001).
Some phenols can polymerize into polyphenols that can bind
minerals. Proanthocyanidins often occur as oligomers or poly-
mers of monomeric flavonoids, polyhydroxy flavan-3-ols such as

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Natural antioxidants . . .

H 3C H 3C

CH3 CH3

H CH2 H 2C H

CH3 H CH2 H 2C H

HO HO

O H3 C O
CH3
CH 3 CH 3
CH3 CH3

Alpha tocopherol Gamma tocopherol

O

OH

CH3 CH 2O C (CH2) 14 CH 3

CH HCOH
H O
OH C O
C O
O
C
C
OH
OH
OH OH

Ascorbic acid Ascorbyl palmitate

OH
OH

HO OH

O O

HO OH

Propyl gallate Resveratrol

Figure 6–Natural antioxidants (alpha- and gamma-tocopherol, ascorbic acid, ascorbyl palmitate, propyl gallate, and resveratrol).

[+]-catechin and [−]-epicatechin (Dixon and others 2005;
Figure 3 and 5). The polymeric procyanidins are better antiox-
idants than the corresponding monomers, catechin, and epicat-
echin (Ursini and others 2001). Catechin and epicatechin can
combine to form esters, such as catechin/epicatechin gallate, or
bond with sugars and proteins to yield glycosides and polyphe-
nolic proteins. Glycosylation of flavonoids at the 3 −OH group
usually decreases the antioxidative activity due to the reduction of
the number of phenolic groups (quercetin/rutin; Figure 3).
Proanthocyanidins with demonstrated antioxidant activity and
potential biologically therapeutic effects occur in fruits (apples and
cherries), some berries (rosehips, raspberries, blackberries, and
strawberries), as well as in the leaves (tea), seeds (grape, sorghum,
soy, and cocoa bean), and bark of many plants (Dixon and others
2005; Buricova and Reblova 2008; Bak and others 2010).
α-Tocopherol
α-Tocopherol (vitamin E) is a fat-soluble carotenoid whose
antioxidative capacity has been studied extensively (Figure 6).
α-Tocopherol is the major vitamin E compound in plant leaves
where it is located in the chloroplast envelope and thylakoid mem-
branes in proximity to phospholipids (Onibi and others 2000). It

c 2011 Institute of Food Technologists®

 Vol. 10, 2011 r Comprehensive Reviews in Food Science and Food Safety 229
Natural antioxidants . . .
deactivates
r photosynthesis-derived reactive oxygen species (es-
pecially O2 − ) and prevents the propagation of lipid peroxida-
tion by scavenging lipid peroxyl radicals in thylakoid membranes
(Munné-Bosch 2005).
Trolox is a water-soluble derivative of vitamin E. Structurally
related lipid-soluble antioxidants that differ in the number of
methyl groups (δ-tocopherol compared with α-tocopherol) have
different free radical-scavenging activities and different surface
activities (Figure 6; Chaiyasit and others 2005). Giuffrida and
others (2007) evaluated the ability of α-tocopherol, δ-tocopherol,
ascorbyl palmitate, and propyl gallate (300 mg/kg; Figure 6) to pre-
vent oxidation in sunflower oil and high-oleic sunflower oil, both
rich in di-unsaturated fatty acids, and in partially hydrogenated
palm oil containing monounsaturated fatty acids. δ-Tocopherol
was the most effective antioxidant in sunflower oil, and propyl
gallate was the most effective in the more saturated oils. Yeum
and others (2009) reported synergistic effects between AA and
α-tocopherol in protecting an in vitro biological model system.
r AA regenerates α-tocopherol after α-tocopherol
It may be that
donates a H to an oxidizing lipid.
α-Tocopherol can also inhibit oxidation of protein. Estévez and
Heinonen (2010) demonstrated that α-tocopherol reduced for-
mation of α-aminoadipic and γ -glutamic semialdehydes from ox-
idized myofibrillar proteins.
In general, vitamin E added to water-based food systems us-
ing an oil carrier targets the neutral lipid fraction (triacylglyc-
erols) rather than the polar lipid fraction (phospholipids) and is
not an effective antioxidant. However, δ-tocopherol added using
a polar carrier can be incorporated into the phospholipid fraction
and is an effective antioxidant (Wills and others 2007). In a lard
model system, the antioxidative activity of the tocopherols is tem-
perature dependent (Reblova 2006). At 80 ◦ C, the antioxidative
activity of δ-tocopherol is about twice that of α-tocopherol; how-
ever, it decreases as temperature increases. Antioxidative activity of
α-tocopherol decreases above 110 ◦ C, and both lose their activity
above 150 ◦ C.
Dietary supplementation of α-tocopherol increases incorpo-
ration of the antioxidant into the phospholipid membrane re-
gion where the polyunsaturated fatty acids are located. Including
α-tocopherol in livestock diets has been shown to have signifi-
cant effects on the antioxidative activities of their tissues and the
stability of meat derived from them (Formanek and others 2001;
Swigert and others 2004; Guo and others 2006; Boler and others
2009; Lahucky and others 2010).
Ascorbic acid
AA has 4 −OH groups that can donate hydrogen to an oxi-
dizing system (Figure 6). Because the −OH groups (2 pairs of 2)
are on adjacent carbon atoms, AA is able to chelater metal ions
(Fe++ ). It also scavenges free radicals, quenches O2 − , and acts as
a reducing agent. At high levels (>1000 mg/kg), AA shifts the
balance between ferrous (Fe2+ ) and ferric iron (Fe3+ ), acts as an
oxygen scavenger, and inhibits oxidation. However, at low levels
(<100 mg/kg), it can catalyze oxidation (in muscle tissue; Ahn
and others 2007; Yetella and Min 2008).
Environmental conditions and the presence of other compounds
in the system can alter the antioxidative capacity of AA. Allam and
Mohamed (2002) reported that, using the induction period for
the oxidation of sunflower oil as a measure of antioxidant activity
after heating (180 ◦ C), ascorbyl palmitate was less thermally stable
than mixed tocopherols, propyl gallate, BHT, or BHA. This may
be a function of the water solubility of AA.
230 Comprehensive Reviews in Food Science and Food Safety r Vol. 10, 2011
Herbs
A number of spices and herbs contain compounds that can be
removed and added to food systems to prevent oxidation (Lee and
Shibamoto 2002; Ahn and others 2007; Rojas and Brewer 2007,
2008a; Sasse and others 2009). Antioxidant (and flavor) compo-
nents of herbs and spices may be removed/concentrated as extracts,
essential oils, or resins. Extracts are soluble fractions that can be
removed from plant materials by solubilizing the component(s) of
interest in an aqueous, lipid, alcohol, solvent, or supercritical CO2
phase then removing it. Essential oils are the volatile oils and often
contain isoprenoid compounds. Chemically, essential oils are ex-
tremely complex mixtures containing compounds of every major
functional group class. Essential oils are isolated by steam distilla-
tion, extraction (solvent or CO2 ), or mechanical expression from
the plant material. Plants also contain resins that are nonvolatile,
high molecular weight, amorphous solids, or semisolids that flow
when subjected to heat or stress. They are typically light yellow
to dark brown in color, tasteless, odorless or faintly aromatic, and
translucent or transparent. Most resins are bicyclic terpenes (alpha-
and beta-pinene, delta-3 carene, and sabinene), monocyclic ter-
penes (limonene and terpinolene), and tricyclic sesquiterpenes
(longifolene, caryophyllene, and delta-cadinene). They are solu-
ble in most organic solvents but not in water. Resins may contain
small amounts of volatile phenolic compounds.
Extracts of many members of the Labiatae (Lamiaceae) fam-
ily (oregano, marjoram, savory, sage, rosemary, thyme, and basil),
which are antioxidative, have a high total phenol content (Chen
and others 2007). They do not necessarily have a high free radical-
scavenging ability but appear to contain components that func-
tion by at least 2 different antioxidative mechanisms (Madsen and
others 1996). Dorman and others (2003) observed that, while
these antioxidant characteristics are not entirely related to the total
phenolic contents, they do appear to be strongly dependent on ros-
marinic acid, the major phenolic component present. Rosmarinic
acid has vicinal −OH groups on each of 2 aromatic rings, while
carnosic acid, carnosol, and rosmanol each have vicinal −OH
groups on only 1 aromatic ring (Figure 3). A number of herbs
(chamomile, rosehip, hawthorn, and lemon verbena) can enhance
the activity of antioxidative enzymes such as superoxide dismutase
and catalase in a dose-dependent manner and have been shown to
enhance cell viability and provide protective effects against oxida-
tive stress induced by hydrogen peroxide (in lung fibroblasts; Yoo
and others 2008).
Rosemary
Chen and others (2007) reported that, of several herbs (Psidium
guajava L., Camellia sinensis [Gamma Amino Butyric Acid tea], T.
sinensis Roem., and Rosemarinus officinalis L.), the aqueous extract
of rosemary contained the highest concentration of phenolic sub-
stances (185 mg/g; Folin–Ciocalteau) and total flavonoids (141
mg/g). This aqueous extract inhibited UVB-induced (100 to 400
nm) oxidation of an erythrocyte ghost system (in vivo model sys-
tem) at a relatively low concentration (100 μg/mL; Chen and
others 2007). At 100 mcg/mL, rosemary extract was able to scav-
enge 39% of the DPPH radicals (0.2 μm); at 500 mcg/mL, it
scavenged 55%. Rosemary extract (100 mcg/mL) inhibited lipo-
some (egg lecithin with Fe3+/AA/H2 O2 ) oxidation by 98%.
The most active antioxidative constituents of rosemary (R.
officinalis) are phenolic diterpenes (carnosic, carnosol, rosmanol,
rosmadial, 12-methoxycarnosic acid, epi-, and iso-rosmanol) and
phenolic acids (rosmarinic and caffeic) (Table 4; Figure 1 and 2;
Frankel 1991; Frankel and others 1996; Richheimer and others
c 2011 Institute of Food Technologists®

Natural antioxidants . . .

Nakatani and Inatani (1981), Arouma and others (1992), Cuvelier and others (1994), Dorman and others (2000, 2003), Ahn and others (2002, 2007), Aoki and Wada (2003), Dorman and others (2003), Thorsen and Hildebrandt (2003), Lee and others (2005), Bozin and others (2006),
noids∗
1996; Nakatani 2003; Thorsen and Hildebrandt 2003; Carvalho

Flavo-

X
X
X
X
X

X
X
and others 2005). Carnosic acid has several times the antioxida-
tive activity as BHT and BHA (Richheimer and others 1996).
The synthetic phenolic antioxidants, BHA and BHT, each have

Cymene
aromatic ring with 1 −OH group capable of donating

p-
a single

X
X

X
r
H . While carnosic acid also has ar single aromatic ring, it has
2 −OH groups that can serve as H donors. In addition, vicinal
Phenylpropanoids

acrol
Carv −OH groups can chelate prooxidative metals thereby preventing

X
oxidation via 2 mechanisms. Hra and others (2000) reported that,
in sunflower oil, rosemary extract exhibited antioxidant activity
Eugenol

superior to α-tocopherol. The polyphenol, rosmarinic acid has

X
X
2 aromatic rrings, each with 2 −OH groups that are capable of
donating H and chelating metals. Adding α-tocopherol to rose-
Thymol

mary can have either an antagonistic effect (Hra and others 2000)
X
X

X
or a synergistic effect (Aoki and Wada 2003). This may indicate
that there are components in rosemary, other than rosmarinic acid,
which make substantial contributions to the antioxidative capacity
pinene
α, β

of the extract. It may also be a function of the solubility of the

X
X

X
X

rosemary fractions used compared to that of α-tocopherol with

respect to the food system to which it being added.
Volatiles

Thujene

In lipid-based systems, carnosic acid and carnosol effectively

α-

chelate iron and scavenge peroxyl radical (Arouma and others

1992). However, free radical-scavenging activity ability does vary
among the different compounds: 1,8-cineole = 62.5%, β-pinene =
Cineole

46.2%, and α-pinene = 42.7% found in rosemary essential oil

1,8-

X
X

(Wang and others 2008). The ethanol extract of rosemary has

higher antioxidative activity than do the individual phenolic com-
Carrillo and Tena (2006), Yanishieva and others (2006), Hatzidimitrioua and others (2007), Bitar and others (2008), and Hernandez-Hernandez and others (2009).

pounds (carnosic acid, carnosol, 1,8-cineole, α-pinene, camphor,

Caffeic
acids
X

camphene, and β-pinene) separately (Wang and others 2008;

Hernandez-Hernandez and others 2009). Solvents of medium po-
Phenolic acids

larity extract higher concentrations of carnosic acid from rosemary

phenolic
Simple
acids

and sage than do solvents of higher or lower polarity (Trojakova and

X
X
X

X
X

others 2001). In addition, different varieties of rosemary, grown

in different regions under different conditions may vary in the
inic acid
Rosmar-

content of these phenolic compounds.

X
X
X
X
X
X

Oregano
Water/ethanol, dichloromethane, and ethanol extracts of
Carn-
osol

oregano (Origanum vulgare L.) also contain high concentrations

X
X

X
X

of phenols, primarily rosmarinic acid, as well as phenolic car-

boxylic acids and glycosides that are both antioxidative and ef-
Carnosic
Table 4–Selected antioxidant compounds identified in selected herbs.

fective superoxide anion radical scavengers (Kim and Cho 2001;

acid
X
X

Bendini and others 2002; Nakatani 2003; Hernandez-Hernandez

and others 2009; Table 3 and 4). Oregano has a high total phe-
nolic compound concentration (15.8 mg gallic acid equivalent
Rosmari-
diphenol
Phenolic diterpenes

[GAE]/g) and antioxidant activity. Using the reducing power as-

X

say, radical-scavenging assay, and the beta-carotene linoleic acid

model system, Muchuweti and others (2007) determined that
oregano had an antioxidant activity of 58.3% exceeded only by
madial
Ros-

cinnamon (61.8%). Using hexanal as an indicator, Stashenko and

others (2002) demonstrated that the essential oils of oregano and
rosemary were both more effective at inhibiting Fe2+ -induced oxi-
ros manol
Epi-, iso-

dation of linoleic acid in a sunflower oil model system than vitamin

X
X

E, Trolox, or BHA. This fraction contained unglycosylated and

glycosylated flavanones as well as dihydroflavonols, all of which
have antioxidative activity.
manol
Ros-

X
X

Marjoram
∗ Lamiaceae family.

Of a number of herbs and spices (bay leaves, rosemary, sage,

Rosemary∗

Marjoram∗
savory∗
Oregano∗

marjoram, oregano, cinnamon, parsley, sweet basil, and mint),

Bay Leaf
Summer
Thyme∗
Sage∗

Basil∗

marjoram (Origanum majorana L.) has the highest proportion of

simple phenolic compounds (96%; Muchuweti and others 2007).

c 2011 Institute of Food Technologists®

 Vol. 10, 2011 r Comprehensive Reviews in Food Science and Food Safety 231
Natural antioxidants . . .

Marjoram essential oil also contains a significant amount of both number of −OH groups appears to coincide with the antioxidant
rosmarinic acid and carnosol (Table 4; Figurer 1 and 2). The es- potential of these compounds.
sential oil can scavenge hydroxyl radicals (OH ). It has antiradical Using an aldehyde/carboxylic acid assay, Lee and others (2005)
activity exceeding that of the phenolic component thymol. In a demonstrated that carvacrol and thymol (5 ppm) can inhibit oxida-
linoleic acid model system, at 5 mg/mL, marjoram has a radical- tion almost completely for 30 d. The primary aroma compounds
scavenging activity of 92%, inhibits conjugated diene formation in thyme include 1,8-cineole, thymol, carvacrol, and α-terpineol
by 50%, and formation of secondary oxidation products by 80% (Table 4; Figure 4; Lee and others 2005). Given that thymol is
(Schmidt and others 2008). the most effective antioxidative component and also one of the
Jun and others (2001) isolated a component (T3b) from marjo- primary aroma compounds in thyme, using extracts of this herb
ram, which is likely a phenolic substance, that is a better superoxide would likely impart unwanted flavors to foods to which they are
anion radical scavenger than α-tocopherol, BHA, BHT, AA, epi- added unless other antioxidative but nonaromatic components can
gallocatechin gallate, quercetin, or epicatechin (Figure 3). The be separated from the extract.
inhibitory mechanism of T3b appears to depend on the action
of superoxide dismutase, an endogenous enzyme that destroys su- Basil
peroxide anion by converting it to H2 O2 . These authors reported In basil, a significant correlation exists between the total phe-
that the methanol extract of marjoram exhibited strong superoxide nolic content and antioxidant activity (Juliani and Simon 2002).
anion radical-scavenging ability (85.5%). Purple basil (Ocimum basilicum) extracts have a higher total phe-
Marjoram essential oil is also rich in terpinen-4-ol, cis-sabinene nolic acid content and greater antioxidant activity than do green
hydrate, p-cymene, and γ -terpinene (Vera and Chane-Ming 1999; basil extracts. The essential oil contains <18% eugenol (Figure 4)
Edris and others 2003; Novák and others 2003). The bicyclic as a percentage of the total volatiles; however, it is correlated with
monoterpenes, cis-sabinene hydrate and cis-sabinene hydrate ac- antioxidant activity. However, the low contribution of the essential
etate, appear to be responsible for the flavor of marjoram (Richter oil to the total antioxidant activity (0.05% to 5.9%) suggests that
and Schellenberg 2007). To the extent that these aromatic com- the antioxidant activity of these plants is not due to the presence of
pounds can be separated from marjoram, this herb could be added the essential oils as such, but to other phenolic compounds in green
to foods without adding unwanted flavors. basil and to anthocyanins in purple basil (Juliani and Simon 2002).
The aqueous extract of basil is a concentration-dependent super-
Sage oxide and hydroxyl radical scavenger (Padurar and others 2008).
The polar extracts of sage (Salvia officinalis) have strong radical- The antioxidant activity of this extract has been attributed to its
scavenging ability and superoxide anion radical-inhibiting ability polar phenolic compounds. The total phenolic content of water
(Orhan and others 2007). The antioxidative activity of sage oil and ethanol extracts of basil (GAE) was reported to be equivalent.
compounds, due primarily to the presence of compounds with Hinneburg and others (2006) reported that hydrodistilled extracts
vicinal −OH groups, is correlated with the oxygenated diter- from basil and laurel had the highest antioxidant activities of sev-
pene and sesquiterpene concentrations (Papageorgiou and oth- eral herbs (basil, laurel, parsley, juniper, aniseed, fennel, cumin,
ers 2008). Sage contains some of the same antioxidant phenolic cardamom, and ginger) but not the greatest iron chelation ability.
diterpene compounds found in rosemary such as carnosol, ros- In a linoleic acid peroxidation assay, basil extract was as effective
manol, and rosmadial, in addition to some not found in rosemary as Trolox. Basil also exhibited significant iron-reducing capacity.
(methyl carnosate, 9-ethylrosmanol ether, epirosmanol, isoros- Rosmarinic acid has been identified as the primary pheno-
manol, and galdosol) (Table 4; Figure 1 and 2; Cuvelier and others lic compound in basil leaves and stems (Lee and Scagel 2009).
1994; Miura and others 2002; Pizzale and others 2002; Nakatani Linalool, epi-α-cadinol, and α-bergamotene (7.4% to 9.2%) and
2003). γ -cadinene have been identified as the most common compounds
In model systems, the polar extracts of the Salvia species exhibit in basil essential oil (Hussain and others 2008). Basil essential oil
excellent antioxidant activities compared to BHT (Tepe and others strongly inhibits lipid peroxidation whether induced by Fe2+ ascor-
2006). However, adding sage (0.05%) to raw pork is a less effective bate or by Fe2+ /H2 O2 (Bozin and others 2006). Chicoric acid
antioxidant than feeding α-tocopherol (1000 mg/kg feed) to pigs (caffeic acid derivatized with tartaric acid) has also been identi-
prior to slaughter in terms of preventing oxidation in cooked fied in substantial quantities (Lee and Scagel 2009). Additional
pork patties (McCarthy and others 2001). This suggests that there antioxidant compounds found in basil are shown in Table 4.
is a component of the polar extract that either locates in the
phospholipid membrane, chelates, or reduces free iron or affects Spices
endogenous oxidative systems. Like herbs, spices can have significant antioxidative effects (Suhaj
2006). Wojdyło and others (2007) measured total equivalent an-
Thyme tioxidant capacities and phenolic contents (Folin–Ciocalteu) of
Thymus vulgaris, T. mastichina, T. caespititius, and T. camphorate all 32 spices. Major phenolic acids identified in these spices in-
have antioxidative activities comparable to those of α-tocopherol cluded caffeic, p-coumaric, ferulic, and neochlorogenic. Predom-
and BHT (Miguel and others 2004). Thyme essential oil exhibits inant flavonoids were quercetin, luteolin, apigenin, kaempferol,
very strong free radical-scavenging ability and inhibits lipid oxi- and isorhamnetin.
dation induced by both Fe2+ /ascorbate and Fe2+ /H2 O2 (Bozin Spices can also have antibacterial effects. Shan and others (2005,
and others 2006). In terms of antioxidative activity, thyme oil > 2007) found that, of 46 spice extracts evaluated, many exhibited
thymol > carvacrol > γ -terpinene > myrcene > linalool > p- antibacterial activity against foodborne pathogens. Gram-positive
cymene > limonene > 1,8-cineole > α-pinene (Youdim and bacteria were generally more sensitive than Gram-negative bac-
others 2002). Carvacrol and thymol each have 1 aromatic ring and teria. Staphylococcus aureus was the most sensitive, while Echerichia
1 −OH group, 1-terpineol has 1 −OH group, while p-cymene coli was the most resistant. The antibacterial activity of the extracts
has 1 aromatic group. The presence of aromatic groups and the was closely associated with their phenolic content.

232 Comprehensive Reviews in Food Science and Food Safety r Vol. 10, 2011 c 2011 Institute of Food Technologists®

Natural antioxidants . . .

enol
Eug
Cinnamon

Nakatani and Inatani (1981), Arouma and others (1992), Ahn and others (2002, 2007), Dorman and others (2003), Shan and others (2005), Carrillo and Tena (2006), Jirovetz and others (2006), Jukic and others (2006), Schmidt and others (2006), Yanishieva and others (2006), Chaieb
X
X
X

X
X
Cinnamon (Cinnamonum zeylanicum) contains a number of

acid benzoic acid benz aldehye aric acid Pinene phyllene cumin taene phene lool gerol ine Limonene mene acrol alde hyde alde hyde
antioxidative components including vanillic, caffeic, gallic, pro-

Cinn-am-
Phenylpropanoids
tochatechuic, p-hydroxybenzoic, p-coumaricd, and ferulic acids

X
X

X
and p-hydroxybenzaldehyde (Table 5, Figure 1, 2, 4, and 5;
(Muchuweti and others 2007). Of a number of herbs and spices

Cumin-
(bay leaves, rosemary, sage, marjoram, oregano, cinnamon, pars-

X
ley, sweet basil, and mint) evaluated, cinnamon has been re-
ported to have the highest polyphenolic compound concentration
(13.7 mg GAE/g; Muchuweti and others 2007). Of 42 commonly

Cy- Carv

X
X
used essential oils, cinnamon bark, oregano, and thyme have been
reported to have the strongest free radical-scavenging abilities (Wen

X
X
X
X
X
X
and others 2009). At 5 mg/mL, cinnamon a radical-scavenging
activity of 92% (Muchuweti and others 2007). The major com-
ponents responsible for this activity were identified as eugenol,

X
carvacrol, and thymol. Jayaprakasha and others (2003) identified
27 compounds in the volatile oil of cinnamon stalks. The volatile
oil was 44.7% hydrocarbons and 52.6% oxygenated compounds.

Cur Argen Cam- Lina Gin Piper

Using a β-carotene-linoleate model system, the volatile oil in-

X
hibited 55.9% and 66.9% of the oxidation at 100 and 200 ppm,

∗ Flavonoids: kaempferol glycosides, rutin, apigenin, kaempferol, hesperetin, dihydroquercetin, quercetin, and catechins (catechin, epicatechin epigallocatechin gallate, and epicatechin gallate).
respectively, compared to the control. The antioxidant capability

X
of cinnamon essential oil is stronger than its free radical-scavenging
capacity (Chen 2008). However, it is a better superoxide radical

X
X
X
Volatiles
scavenger than propyl gallate, mint, anise, BHA, licorice, vanilla,
ginger, nutmeg, or BHT (Murcia and others 2004).

X
Cinnamon (bark and leaf) oleoresin can significantly inhibit
formation of primary and secondary oxidation products. Singh

X
and others (2007) identified 13 components, which accounted
for 100% of the total amount, in cinnamon bark volatile oil. The
bark oleoresin contained 17 components that accounted for 92.3%

X
of the total amount. The major component in cinnamon bark
oleoresin was (E)-cinnamaldehyde (49.9%). Schmidt and others
(2006) identified small amounts of β-caryophyllene, benzyl ben-
Caro
α, β

X
X

X
zoate, linalool, eugenyl acetate, and cinnamyl acetate in cinnamon

and others (2007), Hatzidimitrioua and others (2007), Hernandez-Hernandez and others (2009), and El-Ghorab and others (2010).
leaf essential oil. The major component identified in cinnamon
p- Coum α, β-

leaf oil was eugenol (87.2%). Cinnamon leaf oil has a significant
X
X
X
X
inhibitory effect on hydroxyl radicals and acts as an iron chelator ef-
ficiently inhibiting formation of conjugated dienes and generation
of secondary products from lipid peroxidation at a concentration
X
X

X
X

equivalent to BHT.
Table 5–Selected antioxidant compounds identified in selected spices.

Clove
droxy
p-Hy

The primary components of clove (Eugenia caryophyllus) essen-

X
X

tial oil are phenylpropanoids such as eugenol, carvacrol, thymol,

and cinnamaldehyde (Figure 4; Chaieb and others 2007). Clove
also contains a variety of nonvolatile compounds (tannins, sterols,
Phenolic acids

flavonoids, and triterpenes). Jirovetz and others (2006) identi-

droxy
p-Hy

X
X

fied 23 compounds in clove oil including eugenol (76.8%), β-

caryophyllene (17.4%), α-humulene (2.1%), and eugenyl acetate
(1.2%). A variety of the antioxidative compounds are shown in
Van-illic Caffeic Gallic

Table 5.
X
X
X
X

Clove essential oil is inhibitory toward hydroxyl radicals and

can chelate iron. Comparing 16 spices, Khatun and others
acid
X
X
X
X
X
X

(2006) found that clove had the highest radical-scavenging activity

followed by allspice and cinnamon. Eugenol has been reported
to have an antioxidative activity equivalent to Trolox, carvacrol
acid
X

(oregano), and thymol (thyme; Dorman and others 2000). The

essential oil scavenges free radicals at concentrations lower than
Black pepper

those of eugenol, BHT, and BHA alone. Using peroxide values

Cinn-amon

Turm-eric

and formation of conjugated dienes, Marinova and others (2008)

Nut-meg
Ginger

established that in sunflower oil at 100 ◦ C, myricetin is a more

Clove

effective and stronger antioxidant than α-tocopherol. Mixtures of

c 2011 Institute of Food Technologists®

 Vol. 10, 2011 r Comprehensive Reviews in Food Science and Food Safety 233
Natural antioxidants . . .

the 2 exhibited a synergistic effect that was optimized in an equal out Asia for centuries. Ground turmeric consists primarily of
molar ratio of the 2. curcumin, dimethoxycurcumin and bis-dimethoxycurcumin, and
The antioxidant activity of glycosidically bound volatile com- 2,5-xylenol (Zhang and others 2009). Curcumin is an unsaturated
pounds in clove essential oil has been reported to be significantly diketone that exhibits keto-enol tautomerism (Anand and others
greater than that of the volatile aglycones (Politeo and others 2008).r It is a classical phenolic chain-breaking antioxidant, donat-
2010). The glycosides can undergo enzymatic hydrolysis releasing ing H from the phenolic groups rather than from the CH2 group
their aglycones, therefore, could be considered as potential antiox- (Ross and others 2000). Jayaprakashaa and others (2006) reported
idant precursors. Heating at 100 ◦ C for up to 6 h increases the per- that the antioxidant activity of the curcuminoids is curcumin >
oxy radical-scavenging activity of clove (Khatun and others 2006). BHT, dimethoxycurcumin > bisdemithoxycurcumin. All of these
polyphenolic molecules have limited water solubility. Curcumin is
Nutmeg highly effective in neutralizing free radicals (Yu and others 2008).
Jukic and others (2006) isolated glycosidically bound volatiles At the same concentration, curcumin has about twice the an-
from nutmeg and identified free aglycones in the essential oil. The tioxidative activity of the polyphenol resveratrol (Aftab and Vieira
glycosidically bound and aglycone fractions had only 2 compounds 2009). Turmeric oil has a free radical-scavenging ability compa-
in common, eugenol and terpinen-4-ol. The aglycone fraction rable to vitamin E and BHT (Yu and others 2008). The major
had stronger antioxidant properties than did the free volatiles from components of turmeric oil responsible for this antioxidant activ-
the oil. Nutmeg (Myristica fragans and M. argentea) contains ar- ity are α- and β-turmerone, curlone, and α-terpineol (Carolina
genteane, a flavanol diglycoside, which appears to be the primary and others 2003).
antioxidative compound (Calliste and others 2010). Bis-erythro Heating dry ginger and turmeric and their essential oils at
argenteane is a di-lignan that has been isolated from nutmeg mace 120 ◦ C results in different degrees of retention of antioxidant ac-
(the lace-like seed membrane of nutmeg). The argenteane central tivity (Tiwari and others 2006). Antioxidant activity of turmeric
moiety (3,3 -dimethoxy-1,1 -biphenyl-4,4 -diol) appears to ower oil is higher after heating while that of ginger oil is lower. This
its free radical-scavenging ability to its ability to release 1 or 2 H may be due to the difference in monoterpene content or to the
(Chatterjee and others 2007; Calliste and others 2010). Nutmeg release of bound antioxidants caused by the heat treatment. A va-
also contains significant amounts of myristicin and safrole that are riety of the antioxidant compounds found in ginger and nutmeg
responsible for the characteristic aroma of nutmeg (Fisher 1992). are shown in Table 5.
Myristicin and safrole have similar structures: a 6-membered aro- Cumin is derived from Cuminum cyminum. The major com-
matic ring bound to an oxygenated 5-carbon ring on one side ponents in cumin volatile oil are cuminal, γ -terpinene, and
and a hydrocarbon side chain on the other (Figure 4). After heat- pinocarveol (El-Ghorab and others 2010). Cumin essential oil is
ing (180 ◦ C, 10 min), nutmeg oil has a significantly higher free better at reducing Fe3+ ions than dried or fresh ginger or cumin.
radical-scavenging activity, compared to basil, cinnamon, clove,
oregano, and thyme (Tomaino and others 2005). A variety of the Black pepper
antioxidant compounds found in nutmeg are shown in Table 5. Black pepper (Piper nigrum) is a highly valued spice for its distinct
biting quality that occurs at 1.35 ppm. It has a pungency 150 times
Ginger, turmeric, and cumin that of capsaisan (United States Consumer Product Safety Com-
Ginger is derived from the root of Zinger officinale. Fresh and mission 1992) due to the alkaloid piperine (Figure 4; Srinivasan
dried ginger contain relatively large amounts of the volatile oils 2007). The flavor quality is measured by the volatile oil and by the
camphene, p-cineole, alpha-terpineol, zingiberene, and pentade- nonvolatile methylene chloride extract, piperine. Piperine stim-
canoic acid (Figure 4; Tiwari and others 2006; El-Ghorab and ulates the digestive enzymes of the pancreas, enhances digestive
others 2010). The maximum total phenolic contents were ex- capacity, and reduces gastrointestinal food transit time. Piperine
tractable with methanol from fresh ginger (95.2 mg/g dry extract) can also quench free radicals and reactive oxygen species. It can
followed by hexane extraction of fresh ginger (87.5 mg/g dry ex- protect against oxidative damage in vitro. Piperine acts as a hydroxyl
tract). Hydrodistillation produced 23 mg GAE/g (Hinneman and radical scavenger at low concentrations (Mittal and Gupta 2000).
others 2006). Ginger extract has been shown to have antioxidant Kapoor and others (2009) reported that black pepper (P. nigrum)
activity almost equal to that of synthetic antioxidants (BHA and volatile oil contains 54 components that represent about 97% of
BHT; Rehman and others 2003). the total weight. β-Caryophylline (30%) is the major compo-
Kikuzaki and Nakatani (2006) reported that 12 of the 5 nent along with limonene (13%), β-pinene (7.9%), and sabinene
gingerol-related compounds and 8 diarylheptanoids isolated (5.9%). Pepper essential oils also contain α- and β-pinene,
from ginger rhizomes exhibit higher antioxidative activity than cyclohexene, 1-methyl-4-(1-methylethylidene)-2,3-cyclohexen-
α-tocopherol. Authors suggest that this is likely dependent upon 1-ol, limonen-6-ol, (E)-3(10)-caren-4-ol, and t-caryophyllene
side chain structures in addition to substitution patterns on the (Liang and others 2010). The major component of both ethanol-
benzene ring. Hinneburg and others (2006) have suggested that, and ethyl acetate-extracted oleoresins is piperine (63.9% and
for ginger, it may advisable to use extraction media that are able 39.0%, respectively, Liang and others 2010). Using peroxide, p-
to extract the lipophilic antioxidant compounds. anisidine, and thiobarbituric acid tests, the oil and oleoresins
Turmeric is a spice derived from the rhizomes the Cur- have been shown to have stronger antioxidant activity than
cuma longa plant, which is a member of the ginger family BHA and BHT (Kapoor and others 2009) but less than that of
(Zingiberaceae). Rhizomes are horizontal underground stems propyl gallate. Gurdip and others (2004) reported that, while ex-
that send out shoots as well as roots. The bright yellow color tracts were predominantly piperine, piperolein B, piperamide, and
of turmeric is primarily due to fat-soluble, polyphenolic pig- guineensine, the predominant compounds in essential oils were β-
ments known as curcuminoids, primarily curcumin (diferuloyl caryophyllene, limonene, sabinene, β-bisabolene, and α-coapene.
methane; Priyadarsini and others 2003; Anand and others 2008). Some of the antioxidant compounds found in black pepper are
Turmeric has been used as a spice and medicinal herb through- shown in Table 5.

234 Comprehensive Reviews in Food Science and Food Safety r Vol. 10, 2011 c 2011 Institute of Food Technologists®

Natural antioxidants . . .

O Figure 7–Antioxidative sulfur-containing

compounds (S-allyl—cysteine sulfoxide,
diallyl sulfide, allyl trisulfide, and
S OH allyl-cysteine) in allium plant extracts.

O N S

S-allyl L-cysteine sulfoxide Diallyl sulfide

N
OH

S S
S

Allyl trisulfide Allyl-cysteine

Given that piperine is one of the most effective antioxidative The antioxidative effects of shallots are related primarily to their
components and also one of the primary aroma compounds in phenol content (Leelarungrayub and others 2006). According to
pepper, using extracts of this herb would likely impart unwanted Nuutila and others (2003), methanol extracts of onions have sig-
flavors to foods to which they are added unless other antioxidative nificantly higher radical-scavenging activities than garlic and red
but nonaromatic components can be separated from the extract. onion has higher activity than yellow onion. Quercetin content is
highest in red onions (Gorinstein and others 2008). The radical-
Garlic and related herbs scavenging activities are positively correlated with the total phe-
Garlic (Allium sativum L.) has been widely used as a foodstuff nolics in these extracts.
since antiquity. It has acquired a reputation as a therapeutic agent
and herbal remedy in many cultures to prevent and treat heart and Tea extracts
metabolic diseases, such as atherosclerosis, thrombosis, hyperten- The 3 primary types of tea, green, black, and oolong, are pro-
sion, dementia, cancer, and diabetes (Tyler 1993). duced by different processing procedures. Of these types, green tea
Garlic and shallots (Allium ascalonicum) have antioxidant and extracts have the highest total phenolics content, 94% of which
free radical-scavenging characteristics and identifiable odors at are flavonoids (catechins; Duh and others 2004). Oolong tea con-
low concentrations. They contain 2 main classes of antioxi- tains about 18% total phenolics and 4.4% flavonoids. Theaflavins
dant compounds: flavonoids (flavones and quercetins; Figure 3) and thearubigins predominate in black tea. Black tea also con-
and sulfur-containing compounds (allyl-cysteine, diallyl sulfide, tains chlorogenic, caffeic, p-coumaric, and quinic acids (Figure 1;
and allyl trisulfide; Figure 7). The sulfur-containing amino acid Kiehne and Engelhardt 1996). Some of the antioxidant com-
derivative, alliin (S-allyl-L-cystein sulfoxide), can be converted pounds found in tea are shown in Table 6.
into allicin (diallyldisulfide-S-oxide), the compound commonly Much of the antioxidative activity of green tea (C. sinensis)
associated with garlic odor, by the enzyme alliinase. Thiosulfi- appears to be due to natural flavonoids, tannins, and some vitamins
nates, such as allicin, give garlic its characteristic odor; however, (Abdullin and others 2001). The antioxidant activity is linearly
they are not necessarily responsible for all of the various antiox- related to the phenol content (Apak and others 2006) that has
idative and health benefits attributed to it (Amagase 2006). Okada been reported to be about 450 mg/g (Peschel and others 2007).
and others (2005) have suggested that a combination of the allyl Catechins in green tea consist primarily of gallic acid derivatives
group (−CH2 CH=CH2 ) and the −S(O)S− group is necessary (Chen and others 2007). Catechin flavanols appear to account for
for the antioxidant action of thiosulfinates in garlic extracts. S- more than 80% of the total antioxidant activity of green tea but
allylcysteine, S-allyl mercaptocysteine, and nonsulfur compounds, less than 60% of that of black tea (Gardner and others 1998). The
such as saponins, may contribute to the health benefits (hy- radical-quenching ability of green tea has been shown to be more
polipidemic, antiplatelet, procirculatory, immune enhancement, than 20% more effective than that of black tea in both aqueous
anticancer, and chemopreventive activities) associated with garlic. and lipophilic systems.
Gorinstein and others (2008) reported that trans-hydroxycinnamic In tea extracts, the strongest antioxidant and H2 O2 -scavenging
acid (caffeic, p-coumaric, ferulic, and sinapic acids) concentrations activity is due to phenols, with 3 −OH groups bonded to the
in garlic were twice that in onions. Some of the antioxidant com- aromatic ring, adjacent to each other (Sroka and Cisowski 2003).
pounds found in garlic are shown in Table 6, and sulfur-containing Epigallocatechin, which has 3 adjacent −OH substitutions on
compounds are shown in Figure 7. the B ring, has the highest antioxidant activity (Figure 3). In

c 2011 Institute of Food Technologists®

 Vol. 10, 2011 r Comprehensive Reviews in Food Science and Food Safety 235
Natural antioxidants . . .

addition to a flavonoid ring, a 3 ,4 ,5 -trihydroxy (galloyl) group

Rutin

Nakatani and Inatani (1981), Arouma and others (1992), Cuvelier and others (1994), Kiehne and Engelhardt (1996), Dorman and others (2000, 2003), Ahn and others (2002, 2007), Okada and others (2005), Carrillo and Tena (2006), Yanishieva and others (2006), Chen and others
X
are required for Fe++ binding in catechins (Khokhar and Owusu-
Apenten 2003). These polyphenolic flavonoids are particularly
effective free radical scavengers (Figure 3; Lien and others 2008).

Myre
cetin
Others

X
The primary catechin polyphenol [(−)-epigallocatechin-3-gallate]
is also the primary peroxyl-radical-scavenging compound in tea
extracts (Caldwell 2001; Cabrera and others 2003). In terms of free

veratrol
radical-scavenging ability, epicatechin gallate > epigallocatechin >

Res

X
epicatechin (Guo and others 1996). The first 2 compounds have
3 ,4 ,5 -trihydroxy (galloyl) groups while the last does not. Both
Ferulic their iron-chelating and free radical-scavenging activities appear
X to be responsible for the ability of these compounds to protect
X membranes from Fe2+ /Fe3+ -initiated lipid oxidation. In an iron-
Hydrocinnamic acids

mediated reaction, Grey and Adlercreutz (2006) demonstrated

Coumaric

that catechin inhibited oxidation better than AA. They concluded

that catechin’s chelating ability, rather than its radical-scavenging
p-

X
X

mechanism alone, is responsible for the observed antioxidative

activity.
In more complex food systems, tea catechins can have vary-
Caffeic

ing effects. Mitsumoto and others (2005) found that adding tea
X
X
X

catechins to raw beef (200 or 400 mg/kg) inhibited (P < 0.05)

lipid oxidation to a greater extent than vitamin C (200 or 400
mg/kg); however, they increased discoloration in cooked beef
sulfide
Sulfur-containing compounds
Tri

and chicken meat. Chen and others (1998) reported that green
(2007), Hatzidimitrioua and others (2007), Gorinstein and others (2008), Iacopini and others (2008), Hernandez-Hernandez and others (2009), and Calliste and others (2010).

tea catechin extract, consisting primarily of 4 epicatechin iso-

mers, was much more antioxidative than rosemary extract when
sulfide
Diallyl

added to canola oil, pork lard, and chicken fat. In maize (corn)
X

oil triglycerides, Huang and Frankel (1997) found that epigallo-

catechin (140 M), epigallocatechin gallate, and epicatechin gallate
were better antioxidants than either epicatechin or catechin. Both
cysteine
Allyl

gallic acid and propyl gallate were more effective than epicate-
X

chin and catechin. However, in a maize oil-in-water emulsion,

all tea catechins, gallic acid, and propyl gallate were prooxidative
(5 and 20 M) accelerating hydroperoxide and hexanal formation.
catechin gallate

The improved antioxidant activity of tea catechins in liposomes,

Table 6–Selected antioxidant compounds identified in garlic, tea, and grapeseed extract.

Epi gallo

compared with emulsions, may be due to the greater affinity of

X

the polar catechins toward the polar surface of the lecithin bilay-
ers, thus affording better protection (Hatzidimitrioua and others
2007). In a model system mixture of the flavanols, in the same
concentrations as they occur in the tea extracts, the antioxidant
potential has been shown to be a simple summation of the activ-
Epi catechin

ity of the individual components with no apparent synergism or

gallate

antagonism occurring (Gardner and others 1998).

X
X
Flavonoids

Alkyl compounds with double bond(s), such as 3,7-dimethyl-

1,6-octadien-3-ol in green tea extracts and heterocyclic com-
pounds (furfural) in roasted green tea extracts, are major
catechin

volatile constituents that also exhibit some antioxidative activity

Epi

X
X

(Yanagimoto and others 2003).

Grape seed extract

Because red wines are produced from red grapes, the antioxi-
Cate
quin
X
X
X

dant capacity and chemical composition are related to the grapes.

The antioxidant activity of red wines is associated with the con-
tent of polyphenols such as flavonoids, phenolic acids, stilbenes,
cetin
Quer

X
X
X

coummarines, and lignoids (Radovanovic and others 2009). The

phenolic composition varies greatly due to grape variety, envi-
ronmental and climate conditions, soil type, degree of ripeness,
Grape seed extract
Garlic and shallots

and winemaking process (Table 6; Jayaprakasha and others 2001;

Hatzidimitrioua and others 2007; Lachman and others 2007;
Tea extract

Iacopini and others 2008; Rababah and others 2008; Xu and oth-
ers 2010;). Touns and others (2009) reported wide variations in
the contents of total phenols (122 to 441 mg GAE/g), flavonoids

236 Comprehensive Reviews in Food Science and Food Safety r Vol. 10, 2011 c 2011 Institute of Food Technologists®

Natural antioxidants . . .
17 to 48 mc epicatechin [EC]/g), and tannins (15 to 37 mc EC/g)
in the methanolic extracts from seeds of 3 varieties of grapes.
Phenolic compounds in grape seeds and skins include cate-
chins, epicatechins, epicatechin-3-O-gallate, phenolic acids, caf-
feic acid, quercetin, myricetin, proanthocyanidins, and resveratrol
(Figure 1, 3, and 4; Jayaprakasha and others 2001; Hatzidimitri-
oua and others 2007). Many have strong antiradical activity. Most
of the phenolic compounds found in red wines are derived from
the condensation of flavan-2-ol into oligomers (proanthocyani-
dins) and polymers (condensed tannins). Resveratrol, quercetin,
and rutin are generally found in grape skin extracts, while cat-
echin and epicatechin are found in the seeds (Figure 3 and 6).
The phenolic content of grape seeds defatted with hexane then
extracted with methanol and dried under vacuum has been re-
ported to be about 5 mg/100 g, while the anthocyanin content is
between 0.14 and 0.68 g/100 g (Rababah and others 2008).
Iacopini and others (2008) assessed the antioxidant activity of
the extracts and pure compounds using 2 different in vitro tests:
scavenging of the stable DPPH radical and of authentic perox-
ynitrite (ONOO−). Antioxidant activities of grape seed extract
ranged from 66.4% to 81.4%, compared to vitamin E that ranges
from 90.3% to 94.7%. Monophenols, quercetin, rutin, and resver-
atrol may act either synergistically or antagonistically depending
on their concentrations and the reaction temperature. Grape seed
extract has been shown to inhibit both lipid hydroperoxide and
propanal formation in an emulsion system (Hu and Skibsted 2002).
Oligomeric procyanidins may be better antioxidants than their
monomeric counterparts due to their ability to concentrate where
the oxidative reaction is likely to occur.
Resveratrol (trans-3,4 ,5-trihydroxystilbene), produced primar-
ily in the grapevine, is present in various parts of the grape,
including the skin. It has strong antioxidant activity exceeding
that of propyl gallate, vanillin, phenol, BHT, and α-tocopherol
(Murcia and Martinez-Tome 2001). This may be because it has
more phenolic rings (2 compared with 1) than propyl gallate,
phenol, and BHT, and because it has more −OH groups than
α-tocopherol (3 compared with 1). Resveratrol inhibits peroxida-
tion in a concentration-dependent manner. However, it does not
scavenge hydroxyl radicals or does it react with H2 O2 , making it an
inefficient catalyst of subsequent oxidation (Murcia and Martinez-
Tome 2001). Some of the antioxidant compounds found in grape
seed extract are shown in Table 6.
Soares and others (2003) demonstrated that resveratrol,
vitamins C and E, BHT, and propyl gallate were all able to signifi-
cantly inhibit the oxidation of β-carotene by hydroxyl free radicals.
Polyphenolic fractions from grape pomace can repair α-tocopherol
by reducing the α-tocopheroxyl radical (Pazos and others 2009).
Most of the phenolic compounds in fresh wine are derived from
condensation of flavan-3-ol into oligomers (proanthocyanidins)
and polymers (tannins; Granato and others 2011). Granato and
others (2011) reported that the primary phenolics exerting antiox-
idant effects (DPPH and ORAC assays) in Brazilian red wines were
nonanthocyanin flavonoids. Anthocyanins present in these wines
were present solely in their monomeric form and ranged from
about 9 to 237 mg/mL. Flavonoid content varied from 520 to
1795 mg catechin equivalents [CTE]/L. However, after evaluating
80 Spanish red wines, Rivero Perez and others (2008) found that
the free anthocyanin fraction is the primary fraction responsible
for antioxidant capacity and is correlated with electron transfer
processes.
Pazos and others (2006) evaluated the effectiveness of a grape
phenol fraction, isolated grape procyanidins, hydroxytyrosol (from
c 2011 Institute of Food Technologists®
 Vol. 10, 2011 r Comprehensive Reviews in Food Science and Food Safety 237
olive oil), and propyl gallate in inhibiting lipid oxidation in a
fish (hake) microsomal model system. Oxidation was initiated by
hemoglobin, enzymatic NADH iron and nonenzymatic ascorbate
iron. The relative antioxidant efficiency was independent of the
prooxidant system and was isolated grape procyanidin > propyl
gallate > grape phenolic extract > hydroxytyrosol. Antioxidative
effectiveness was positively correlated with incorporation of the
substance into microsomes. However, polarity appeared to play
less of a role in inhibition of hemoglobin oxidation by pheno-
lics underscoring the fact that an exogenous antioxidant must be
incorporated into membranes where unsaturated fatty acids and
iron-reducing enzymes are located in order to be effective. Poiana
and others (2008) demonstrated that during the ageing of red wine,
polymeric anthocyanins increased from about 9% to over 75% after
6 mo, while monomeric anthocyanins decreased from over 75% to
less than 24%. Total antioxidant capacity decreased and was highly
correlated with the monomeric anthocyanin fraction (r > 0.98);
however, free radical-scavenging ability increased and was highly
correlated with the polymeric anthocyanin fraction.
Granato and others (2010) also evaluated the antioxidant activity
and the phenolic content of red wines and verified that ORAC
values correlated well to flavonoid content (r = 0.47; P = 0.01),
total phenolics (r = 0.44), and DPPH (r = 0.67). DPPH values
also correlated well to the content of flavonoids (r = 0.69), total
phenolic compounds (r = 0.60), and nonflavonoid compounds (r =
0.46) (in beers; Granato and others 2011).
The Stereochemistry of Flavanones
Enantiomers are molecules that are mirror images of each an-
other but cannot be superimposed onto one another. Molecules
exhibit stereoisomerism (enantiomers) because they have one or
more chiral centers. A chiral center results from the presence of an
assymetrical carbon atom, that is, one that is attached to 4 differ-
ent atoms or 4 different groups of atoms (making its mirror image
nonsuperimposable). Enantiomers rotate the plane of polarized
light in opposite directions.
Enantiomer names use the R/S system. This system involves no
reference but labels each chiral center R or S using a system in
which its substituents are each assigned a priority, according to the
Cahn-Ingold-Prelog priority rules (Cahn and others 1966), based
on atomic number. If the center is oriented so that the lowest
priority of the 4 substituents is pointed away from a viewer, the
viewer will then see 2 possibilities: if the priority of the remaining
3 substituents decreases in a clockwise direction, it is labeled R
(rectus), and if it decreases in a counterclockwise direction, it is S
(sinister).
Flavanones can have chiral carbon atoms; therefore, they can ex-
ist as S- and R-enantiomers. These enantiomers can be produced
in different quantities in different plant materials under different
growing conditions (Yanez and others 2005, 2008, 2007). They
can have different effects in both biological and inorganic systems.
For these reasons, separating and quantifying them has been of
interest to the medical, biological, and agricultural industries in
the recent past.
The flavanone glycosides naringin and neohesperidin found
in some citrus species have a chiral center in the C-2 position
of the flavanone moiety (Uchiyama and others 2008; Figure 8).
The flavanone hesperetin, the aglycone of hesperidin and major
flavonoid in oranges, contains a chiral C-atom, so it can also
exist as an S- and R-enantiomer. The 2S-herperidin and its S-
hesperitin aglycone predominate in nature (Uchiyama and others
2008).
Natural antioxidants . . .

OH

OH HO OH

HO
HO
O O OH

O OH
O OH
O

O
O OH

O O OH OH

Hesperitin Naringen

OH

O HO OH

HO
OH
O OH
O O O O

HO OH

OH OH

Neohesperidin OH

OH
O O

HO
OH O OH

O O O OH

HO OH

OH OH

Hesperidin

Figure 8–Natural antioxidants that exist as stereoisomers (hesperitin, naringin, neohesperidin, and hesperidin).

Enantiomers can react with other compounds or other enan-
tiomers in different ways or at different rates. Brand and oth-
ers (2010) have demonstrated small, but significant, differences
in the metabolism and transport characteristics, and bioactivity
between S- and R-hesperetin. Naringin, the major flavanone-
7-O-glycoside of sour orange, is responsible for the bitter taste
of the fruit (Caccamese and others (2010). The relative ratios of
naringin and neohesperidin to their C-2 epimers varies depend-
ing on species, maturity, and processing. Separation of naringin
from neohesperidin is complicated by the presence of stereoiso-
mers (Belboukhari and others 2010). Takemoto and others (2008)
developed a high-performance liquid chromatography (HPLC)
method using UV detection for the stereospecific analysis of the
flavan, sakuranetin, found in grapefruit and oranges. Stereospecific
HPLC methods have been developed for separation of epimers in
tea, grapes, orange juice, and C-2 epimers from other sources

238 Comprehensive Reviews in Food Science and Food Safety r Vol. 10, 2011 c 2011 Institute of Food Technologists®

Natural antioxidants . . .

(Uchiyama and others 2008; Caccamese and others 2010; Vega- and others 2001). Three primary extraction techniques are used for
Villas and others 2008; Kim and others 2009; Belboukhari and polyphenols: solvents, solid-phase extraction, and supercritical ex-
others 2010). traction. Using a Soxhlet apparatus combines percolation and im-
Si-Ahmed and others (2010) reported that different mo- mersion that increases extraction efficiency. Several extractions can
bile phases in different ratios are required to accomplish be accomplished with solvents having different polarities (petrol
enantiomeric and diastereomeric separation of a variety of ether, toluene, acetone, ethanol, methanol, ethyl acetate, and wa-
flavanones (flavanone, 2 -hydroxyflavanone, 4 -hydroxyflavanone, ter). Methanol/water/HCl (70:29:1, v/v/v) has been shown to be
6-hydroxyflavanone, 7-hydroxyflavanone, 4 -methoxyflavanone, the best among several solvents evaluated for extracting phenolics
6-methoxyflavanone, 7-methoxyflavanone, hesperetin, hes- from grape seed (Xu and others 2010). Grinding in a mortar in
peridin, naringenin, and naringin). Others have reported simi- liquid nitrogen provides uniform particle size allowing for a more
lar differences in chiral discrimination ability (toward flavanones) consistent extraction.
depending on the buffer and alcohol modifier enantioselectivity Ultrasound can be used to assist liquid solvent extraction. Xu
(Cirilli and others 2008). Abbate and others (2009) described a and others (2010) reported that sequential sonication was a pre-
method for assessing configurational and conformational proper- ferred to mechanical agitation as an extraction method for assessing
ties (of naringenin) using vibrational circular dichroism. phenolic content in grapeseed. Supercritical CO2 extraction can
The stereoselectivity of chiral flavanones and epimers has sig- also be used (Schwarz and others 2001).
nificant biological effects in terms of their pharmacological activ- Hydrodistillation of plant materials has several advantages. The
ity and disposition in humans and livestock. Gardana and others essential oils that carry the intrinsic flavor of a spice can be removed
(2009) reported that some human intestinal bacteria can transform and polyphenols, primary antioxidant compounds, are concen-
diadzein to equol, O-desmethylangolensin, or dihydrodaidzein. trated. In addition, the hydrodistilled compounds are generally
Diet has a clear effect. A diet lower in fiber, vegetables, and cere- more soluble in aqueous media than are those extracted using
als and higher in lipids from animal sources increases production organic solvents. They are often more soluble than synthetic an-
of equol. These stereoselective differences in the chiral forms of tioxidants as well. Hydrodistillation also avoids potential residues
flavonone antioxidants may result in differences in antioxidative from organic solvents. Hydrodistilled extracts have also been re-
effects of the various epimers depending on the matrix and oxi- ported to have a variety of functional effects in foods and in human
dizing group. For these reasons, a concerted effort is being made health (Hinneburg and others 2006). Optimizing the extraction
to separate these chiral compounds and to evaluate their specific process could lead to even better results.
characteristics under defined conditions. The distillation process can also concentrate antioxidant com-
ponents. Naz and others (2011) found that deodorizer distillates
Effects of Processing from sunflower oil processing were richer in tocopherols than the
Endogenous antioxidant systems (enzymatic) can be damaged deodorized oil itself. The implication is that, while the distillation
during food processing (particle size reduction and heating), by process removes unwanted materials from the oil, it may, in fact,
certain ingredients (salts and organic acids), and by storage con- concentrate some of the antioxidants.
ditions (presence of oxygen) such that they are ineffective (Chen
and others 1998). NaCl, in particular, reduces the activity of the Heat treatment
antioxidant enzymes catalase, glutathione peroxidase, and superox- When we think of processing, heat treatment is often the first
ide dismutase that reduces their capacity to perform antioxidative process that comes to mind.
functions (Lee and others 1997). Ingredients, such as AA and citric Antioxidative activity of a given compound may increase, de-
acid, can work synergistically with flavonoid antioxidants. crease, or remain unchanged as a function of temperature. Stability
Spices and herbs can be added to foods in various forms: whole, of an antioxidant to heat is advantageous in the food industry, since
ground, or as isolates from their extracts. Extracting antioxidant many fat- and oil-containing foods are heated during processing
◦
components from a complex matrix depends on the solubility of and since heat is often the initiator of lipid oxidation. At 80 C,
the extractant, the solvent, and the presence of other substances the antioxidative activity of δ-tocopherol is about twice that of α-
that may compete with the extraction process, and the extraction tocopherol; however, it decreases as temperature increases from 80
◦
process itself (vacuum, distillation, pressure, and so on). Because to 150 C. Antioxidative activity of α-tocopherol remains fairly
◦
these substances are aromatic, pungent food ingredients, they may constant between 80 and 110 C, decreasing only at tempera-
◦
or may not be desirable in a nonflavoring (antioxidant or other) tures above 110 C. Neither retains their antioxidative activity at
◦
application (Ruberto and others 2000; Teissedre and Waterhouse 150 C.
2000). For example, even at low concentrations, some components Ginger extract has good thermal stability and inhibits more
◦
of rosemary essential oil (verbenone, borneol, and camphor) can than 85% of linoleic acid peroxidation when heated at 185 C for
◦
impart a rosemary odor to foods (Carrillo and Tena 2006). Solid 120 min (Rehman and others 2003). Heating (120 C) dry ginger
rosemary extract can contain >356 μg/g verbenone, 190 μg/g and turmeric essential oils results in different degrees of antioxidant
borneol, and >135 μg/g camphor (Carrillo and Tena 2006). activity retention. The antioxidant activity of turmeric oil is higher
after heating (120 ◦ C), unlike ginger oil that loses antioxidant
Extraction activity (Tiwari and others 2006). Turmeric oil contains a higher
Because many antioxidants are unstable to oxygen and endoge- concentration of monoterpenes than does ginger oil; however,
nous enzymes, most are extracted from freeze-dried plant materi- release of bound antioxidants by the heat treatment should not be
als. Selecting an appropriate extraction procedure can increase the ruled out.
concentration of the antioxidant compound. Extraction using edi-
ble oil or fat is relatively simple. Herbs and spices can be mixed with Adding antioxidants to livestock diets
fats, oils, or medium-chain triglycerides, allowed to extract under Including herb distillates into livestock diets can have positive
defined time/temperature control, then filtered for use (Pokorny effects. Moclino and others (2008) found that feeding a steam

c 2011 Institute of Food Technologists®

 Vol. 10, 2011 r Comprehensive Reviews in Food Science and Food Safety 239
Natural antioxidants . . .
distilled rosemary by-product to ewes increased rosmarinic acid,
carnosol, and carnosic acid content in the meat. Fresh meat from
these animals had higher total ferric reducing antioxidant power
and lower DPPH values than controls indicating that the rosemary
distillate partitioned into the meat tissues and reduced susceptibil-
ity to oxidation. McCarthy and others (2001) have shown similar
results with pigs. Boler and others (2009) found that feeding vita-
min E to pigs increased pork stability during storage. Simitzis and
others (2008) found that meat from lambs fed a feed that had been
sprayed with oregano essential oil (1 mL/kg) was much more stable
to lipid oxidation during both refrigerated and frozen storage than
that from controls. Gobert and others (2010) found that adding
antioxidants to diets of cattle fed a polyunsaturated fatty acid
(PUFA)-rich diet improved lipid stability in steaks; the combina-
tion of vitamin E and plant extracts rich in polyphenols was more
efficient than vitamin E alone indicating some synergism between
the 2.
Effects of the food matrix and ingredients
Natural plant antioxidants can protect food components from
oxidation under the stress of heating and storage. However, the
inherent characteristics (ionic strength and pH) of the food, the
food matrix (emulsion, foam, aqueous, and protein), and ingredi-
ents can influence antioxidant effectiveness.
Vitamin E added to water-based food systems in an oil carrier
concentrates in the neutral lipid fraction rather than the polar lipid
fraction and is not an effective antioxidant. However, δ-tocopherol
added using a polar carrier can be incorporated into the phos-
pholipid fraction and is an effective antioxidant (Wills and others
2007). In a lard model system, the antioxidative activity of the
tocopherols is temperature dependent (Reblova 2006). Wanatabe
and others (2010) demonstrated that, in a methyl lineoleate/water
emulsion, the effectiveness of AA and acyl ascorbates depended
on whether the oxidation process was initiated by an oil-soluble
prooxidant or a water-soluble prooxidant. The AA concentrated
in the aqueous phase and suppressed oxidation to a greater de-
gree at the oil/water interface when the prooxidant was water
soluble. Docecanoyl and hexadecanoyl ascorbates dissolved in the
oil phase and suppressed oxidation the oil phase (droplets) rather
than at the interface. Increasing the pH appeared to enhance the
electron-donating ability of AA in the water phase ultimately af-
fecting oxidation. Hexadecanoyl ascorbate in the oil phase was not
susceptible to these pH effects. Authors suggest that another expla-
nation may be destabilization of the emulsion through flocculation
and coalescence of the oil droplets at low pH.
Thymol can prevent loss of α-tocopherol (in oil) following
heating at 180 ◦ C for 10 min (Tomaino and others 2005). Using a
lipophilic model system, Lee and Shibamoto (2002) demonstrated
that volatile extracts of thyme (and basil) inhibited the oxidation
of hexanal for 40 d. These extracts also inhibited methyl linoleate
deterioration at 40 ◦ C. In sunflower oil, aroma detection thresholds
of carvacrol, thymol, and p-cymene 2,3-diol have been reported to
be 30, 124, and 794 ppm, respectively (Bitar and others 2008). p-
Cymene 2,3-diol at 335 ppm imparted no negative flavor changes
and reduced oxidation by more than 46%.
Estevez and others (2008) evaluated several phenols (gallic acid,
cyanidin-3-glucoside, (+)-epicatechin, chlorogenic acid, genis-
tein, and rutin) and α-tocopherol in terms of anti- or prooxidative
effects of oil-in-water emulsions containing myofibrillar proteins
(1%). Gallic acid, cyanidin-3-glucoside, and genistein were the
most efficient inhibitors of lipid and protein oxidation. They con-
240 Comprehensive Reviews in Food Science and Food Safety r Vol. 10, 2011
cluded that the nature and conformation of the proteins as well
as the chemical structure of the phenols influenced the overall
effect.
Antioxidant content of raw materials can change over time and
are likely related to storage conditions. Hatzidimitrioua and others
(2007) reported that total phenol content of grape seeds decreases
during storage. Changes were minor for samples stored at less than
55% relative humidity; however, high humidity (75%) accelerated
degradation resulting in a 50% reduction of total phenol content.
Based on the continuous gallic acid release, authors suggested that
this degradation was related to hydrolytic reactions. Modifications
of the storage process would be expected to enhance retention of
antioxidative compounds in grape seeds.
Ingredients, such as salt, can act as prooxidants in food systems;
however, antioxidants can help reduce it. Brannan (2008) found
that grape seed extract helps to mitigate the prooxidative effects
of NaCl in stored ground chicken without affecting moisture
content or pH. The author suggests that grapeseed extract may
alter the effect of NaCl on protein solubility in salted chicken
patties. Whether it affects physicochemical interactions in cooked
meat quality remains to be assessed.
Akarpat and others (2008) demonstrated that adding a hot water
extract of rosemary (10%) to ground beef containing salt (1.5%)
protected color and preserved oxidative quality during frozen stor-
age (120 d). Fasseas and others (2008) found that essential oils from
oregano and sage added to ground beef and pork (3% w/w) re-
duced oxidation. The effect was even more dramatic in cooked
meat than in raw meat.
The antioxidant components of rosemary, sage, basil, black pep-
per, garlic, and onion appear to be relatively stable. Microwave
treatment of these herbs has no effect on reducing power or iron-
chelating capacity (Bertelli and others 2004). However, the effects
on other components, such as flavor components and pigments,
are unknown.
Marinating and cooking (chicken) significantly reduces the an-
tioxidant activities of marinating sauces and consequently reduces
the amounts of antioxidant available (Thomas and others 2010).
Marinating chicken (in herb and spice-based marinades) prior to
cooking reduced the total antioxidant activity (45% to 70%) orig-
inally present in the sauce. This may be due to the ionic effects of
various salts typically included in marinades, the effects of reduced
pH on the phenolic components of the marinades, and/or to
the interactions between antioxidants or between antioxidants and
protein. Loss of antioxidant activity due to cooking may reflect the
protective action of antioxidants on proteins (which are denatured
by heating) or their protective action toward other components
(vitamins).
In addition to reducing lipid oxidation, antioxidants may have
other benefits in food systems. Adding rosemary essential oil
and/or citrus fiber washing water to bologna has been shown
to lower the levels of residual nitrite (Viuda-Martos and others
2010). Flavonoids, hesperidin, and narirutin were identified in
the bologna with hesperidin concentrations being higher than
narirutin concentrations. The preferred (sensory) sample was that
which contained 50 g/kg citrus fiber water and 200 mg/kg rose-
mary essential oil.
There are many types of food matrices to which these antioxi-
dant compounds might be added and many types of processing that
the product might then undergo. There are currently no general
guidelines as to what/when to use plant extracts in food matrices.
More studies are necessary to elucidate that substances are effective
in what systems and under what condition.
c 2011 Institute of Food Technologists®

Natural antioxidants . . .
Synergism
Combining antioxidants may increase their effectiveness. Smet
and others (2008) found that dietary synthetic antioxidants com-
bined with α-tocopherol were more effective than rosemary, green
tea, grape seed, or tomato extracts (100 to 200 ppm) alone or in
combination in sparing tocopherols oxidation and in preventing
oxidation of fresh frozen chicken patties. It has been proposed
that the mixed free radical acceptors involve 2 antioxidants: one
that reacts with the peroxy radical (and is consumed) and a 2nd
that regenerates the 1st, effectively sparing. Phenolic antioxidants
and AA appear to work synergistically in this way (Uri 1961).
r r
(1) ROO
r + A:H = ROO:H
r +A
(2) A + B:H = A:H + B .
Some acidic compounds, such as AA and citric acid, can exert
a synergistic effect when added along with polyphenolic antiox-
idants. These acidic compounds chelate metals. These synergists
form an antioxidant radical synergist
r complex (A:S) such thatr nei-
ther the antioxidant radical (A ) nor the synergist radical (S ) can
catalyze oxidation reactions. This chemical association suppresses
the antioxidant radical’s ability to assist in the breakdown of lipid
peroxides (Aurand and Woods 1979).
Addition of anthocyanin can prevent oxidation of AA by metal
ions such as copper (Sarma and others 1997). Anthocyanin not
only chelates metal ions, but also forms an AA (copigment-metal-
anthocyanin) complex that may be the basis for its antioxidative
activity. Because of the number of −OH groups on the aro-
matic rings, and because of their water solubility, anthocyanins are
pH-sensitive. In a basic solution, the −OH groups can give r up
H+; in a more neutral r environment, they can donater H to an
oxidizing lipid (ROO ). For this reason, the antioxidative capacity
of an anthocyanin is dependent on the anthocyanin itself (num-
ber and location of −OH groups), the pH of the surrounding
environment, and the other components of the system (metals,
continuous phase).
Lee and others (2005) found that combinations of chelators
(sodium tripolyphosphate or sodium citrate) with reductants (ery-
thorbate), and/or free radical scavengers (BHA and rosemary ex-
tract) were effective antioxidants. The combination of rosemary
and erythorbate was most effective in delaying lipid oxidation in
ground beef. The rosemary/citrate/erythorbate combination was
most effective in stabilizing color and delaying lipid oxidation.
These findings indicate that combining a reductant with a free
radical scavenger is more effective at preventing lipid oxidation
than either alone.
In a mixture of 3 monophenols (catechin, resveratrol, and/or
quercetin) derived from grapeseed, Pinelo and others (2004) found
an initial increase in antioxidative activity followed by a subse-
quent decrease for all solution combinations. They also reported a
possible synergy between quercetin, rutin, and resveratrol toward
ONOO−. The effect was additive for catechin and epicatechin.
These compounds may be acting independently, while other com-
binations may react with each other.
Granato and others (2010) found that (in brown ales) flavonoids,
total phenolics, and nonflavonoid phenolics (hydroxycinnamates
and hydroxybenzoates), derived from both the malt and the hops,
are strongly correlated with antioxidant activity (ORAC and
DPPH). Ghiselli and others (2000) have shown that beer increases
serum antioxidant capacity. Ethanol increases absorption of phe-
nolic acids. However, the increase in antioxidant capacity is not
due to either ethanol or phenolic acids alone, but rather because
of a synergistic effect between the 2.
c 2011 Institute of Food Technologists®
 Vol. 10, 2011 r Comprehensive Reviews in Food Science and Food Safety 241
Regulatory Status of Extracts, Concentrates, and
Resins
Synthetic antioxidants (BHA, BHT, and EDTA) are regulated
by the Food and Drug Administration (FDA) as direct food addi-
tives. They may be used alone or in combination not to exceed
0.02% (2 ppm) of the final product in specified food products
(21CFR172.110). These antioxidants are considered to be safe
and suitable ingredients for use in meat, poultry, and egg products,
alone or in combination, not to exceed 0.02% of the fat content
(FSIS Directive 7120.1. revision 5).
Some herb and spice extracts and oleoresins are Generally Rec-
ognized As Safe (GRAS). Some are considered to be indirect ad-
ditives (21 CFR Vol. 3. Part 101); as such, solvents permitted for
the extraction process and solvent residues allowed are specified.
Some extracts, concentrates, and resins are regulated by the FDA
“Dietary Supplement Health and Education Act of 1994” and are
considered to be one (or more) of several defined dietary ingre-
dients (a vitamin, a mineral, an herb or other botanical, amino
acid, a dietary substance for use by man to supplement the diet
by increasing the total dietary intake, or a concentrate, metabolite,
constituent, extract, or combination of any ingredient described in
clause (A), (B), (C), (D), or (E) and is excluded from regulation as
a food additive. Extracts, concentrates, and resins are also regulated
under the Food Labeling Regulation, Amendments; Food Reg-
ulation Uniform Compliance Date; and New Dietary Ingredient
Premarket Notification Final Rule (1997). If they are added to
cause flavor or color changes, they are regulated as such and specific
quantities allowable for use in various foods are set forth. Based on
the number of various classifications under which an extract, con-
centrate or resin could be covered, allowable use levels vary widely.
Summary
Plant and animal tissues contain unsaturated fatty acids, primar-
ily in the phospholipid fraction of cell membranes. These lipids
are especially susceptible to oxidation because of their electron-
deficient double bonds. The breakdown products of oxidation can
produce off-odors, new flavors, loss of nutrient content, and color
deterioration. To manufacture high-quality, stable food products,
the most effective solution is often the addition of antioxidants,
either synthetic or natural, which can serve as “chain breakers,” by
intercepting the free radicals generated during various stages of ox-
idation or to chelate metals. Chain-breaking antioxidants are gen-
erally the most effective. A common feature of these compounds
is that they have one or more aromatic rings (often phenolic) with
one or more −OH groups capable of donating H· to the oxidiz-
ing lipid. Synthetic antioxidants, such as BHA, BHT, and propyl
gallate, have one aromatic ring. The natural antioxidants AA and
α-tocopherol each have 1 aromatic ring as well. However, many of
the natural antioxidants (flavonoids and anthocyanins) have more
than 1 aromatic ring. The effectiveness of these aromatic antiox-
idants is generally proportional to the number of −OH groups
present on the aromatic ring(s). Depending on the arrangement
of the −OH groups, these compounds may also chelate prooxida-
tive metals. The facts that they are natural, and have antioxidative
activity that is as good or better than the synthetic antioxidants,
makes them particularly attractive for commercial food processors
because of consumer demand for natural ingredients.
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