Food Chemistry 218 (2017) 99106

Contents lists available at ScienceDirect

Food Chemistry
journal homepage: www.elsevier.com/locate/foodchem

Review

A review of phenolic compounds in oil-bearing plants: Distribution,

identification and occurrence of phenolic compounds
Muhammad H. Aludatt a,b,, Taha Rababah a, Mohammad N. Alhamad c, Majdi A. Al-Mahasneh d,
Ali Almajwal e, Sana Gammoh a, Khalil Ereifej a, Ayman Johargy f, Inteaz Alli b
a

Department of Nutrition and Food Technology, Faculty of Agriculture, Jordan University of Science and Technology, P.O. Box 3030, Irbid 22110, Jordan
Department of Food Science and Agricultural Chemistry, Macdonald Campus, McGill University, 21, 111 Lakeshore Road, Ste-Anne-De-Bellevue, Quebec H9X 3V9, Canada
Department of Natural Resources and Environment, Faculty of Agriculture, Jordan University of Science and Technology, P.O. Box 3030, Irbid 22110, Jordan
d
Department of Chemical Engineering, Jordan University of Science and Technology, P.O. Box 3030, Irbid 22110, Jordan
e
Department of Community Health Sciences, College of Applied Medical Sciences, King Saud University, P.O. Box: 10219, Riyadh 11433 Saudi Arabia
f
Faculty of Medicine, University of Um Al-Qura, Makkah, Saudi Arabia
b
c

a r t i c l e

i n f o

Article history:
Received 22 January 2016
Received in revised form 5 September 2016
Accepted 8 September 2016
Available online 13 September 2016
Keywords:
Distribution
Oil-seed
Total phenolic
Identification
Occurrence
Antioxidant

a b s t r a c t
Over the last two decades, separation, identification and measurement of the total and individual content
of phenolic compounds has been widely investigated. Recently, the presence of a wide range of phenolic
compounds in oil-bearing plants has been shown to contribute to their therapeutic properties, including
anti-cancer, anti-viral, anti-oxidant, hypoglycemic, hypo-lipidemic, and anti-inflammatory activities.
Phenolics in oil-bearing plants are now recognized as important minor food components due to several
organoleptic and health properties, and they are used as food or sources of food ingredients. Variations in
the content of phenolics in oil-bearing plants have largely been attributed to several factors, including the
cultivation, time of harvest and soil types. A number of authors have suggested that the presence phenolics in extracted proteins, carbohydrates and oils may contribute to objectionable off flavors The objective
of this study was to review the distribution, identification and occurrence of free and bound phenolic
compounds in oil-bearing plants.
2016 Elsevier Ltd. All rights reserved.

Contents
1.
2.

3.

Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 99
Types and identification of phenolic compounds in oil-bearing Plants . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 100
2.1.
Phenolic compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 100
2.2.
Polyphenol compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 102
2.3.
Lignans . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 103
2.4.
Extraction, separation and determination of phenolics . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 104
2.5.
Antioxidant activity measurements . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 104
Summary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 104
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 104

1. Introduction
Corresponding author at: Department of Nutrition and Food Technology,
Faculty of Agriculture, Jordan University of Science and Technology, P.O.
Box 3030, Irbid 22110, Jordan, Department of Food Science and Agricultural
Chemistry, Macdonald Campus, McGill University, 21, 111 Lakeshore Road,
Ste-Anne-De-Bellevue, Quebec H9X 3V9, Canada.
E-mail addresses: muhammad.aludatt@mail.mcgill.ca, malodat@just.edu.jo
(M.H. Aludatt).
http://dx.doi.org/10.1016/j.foodchem.2016.09.057
0308-8146/ 2016 Elsevier Ltd. All rights reserved.

Conventionally, oil-bearing plants, such as soybeans, canola,

flaxseed and olives, have been widely used as vital sources of oils
and proteins (Aludatt et al., 2016; CETIOM, 2014; Fine,
Chardigny, Redlingshfer, & Renard, 2015). More recently, the
phenolic compounds of these oil-bearing plants have generated

100

M.H. Aludatt et al. / Food Chemistry 218 (2017) 99106

interest due to their antimicrobial, anti-cancer, anti-viral, antiinflammatory, hypo-lipidemic and hypoglycemic effects (Aludatt,
Rababah, & Alli, 2014; Aludatt, Rababah, Ereifej, Brewer, & Alli,
2013; Bravo, 1998; Khattab, Eskin, & Thiyam-Hollander, 2014).
Variations in the types, amounts and properties of phenolic compounds in oil-bearing plants and their processed food products
have been studied extensively (Aludatt, Rababah, Ereifej, Brewer,
& Alli, 2013; Aludatt et al., 2014; Bravo, 1998; Herchi et al., 2014).
Recently, the nutritional characteristics of phenolic compounds
have been more widely studied because of the deleterious effects
that are produced by the chemical nature of phenolic compounds
that allows them to conjugate with other food constituents, such
as vitamins, minerals, fatty acids, peptides, proteins, lipids and carbohydrates. This may reduce the digestibility and nutritional properties of food products (Aludatt, Rababah, Ereifej, & Alli, 2013;
Aludatt, Rababah, Ereifej, Brewer, & Alli, 2013; Aludatt et al.,
2014). Numerous groups of phenolic compounds have been isolated and identified in oil-bearing plants, including simple phenolic
compounds (Aludatt, Rababah, Ereifej, & Alli, 2013; Aludatt et al.,
2014; Janiak, Slavova-Kazakova, Kancheva, & Amarowicz, 2014;
Shim, Gui, Arnison, Wang, & Reaney, 2014) and complex phenolic
compounds (Janiak et al., 2014; Shim et al., 2014).
In some cases, the functional properties of oil-bearing plants are
influenced by the interactions of individual food components with
phenolic compounds (Aludatt, Rababah, Ereifej, & Alli, 2013;
Aludatt et al., 2014). Protein-lipid-phenolic interactions, proteinphenolic interactions and lipid-phenolic interactions have been
studied extensively both in vitro and in vivo (Aludatt, Rababah,
Ereifej, Brewer, & Alli, 2013; Aludatt et al., 2014). This review will
discuss issues related to the phenolic extraction, content, profile
and identification of oil-bearing plants due to the pharmaceutical
and nutraceutical value of the phenolic compounds to the human
health and food industry.

2. Types and identification of phenolic compounds in oilbearing Plants

2.1. Phenolic compounds
Phenolic compounds are classified divided according to their
chemical structures into simple phenols (e.g., phenol, cresol, thymol and orcinol), phenolic acids (e.g., gallic, protocatechuic, vanillic
and syringic acids), aldehyde forms of phenolic acids (e.g., vanillin,
syringaldehyde and p-hydroxybenzaldehyde), phenylacetic acids,
acetophenones, phenylpropanoids and their derivatives, chromones and coumarins (e.g., umbilliferone and aesculetin), and cinnamyl alcohols (e.g., coniferyl, sinapyl, syringyl and p-coumaryl
alcohols) (Aludatt, Rababah, Ereifej, & Alli, 2013; Aludatt,
Rababah, Ereifej, Brewer, & Alli, 2013; Aludatt et al., 2014; Bravo,
1998). Phenolic compounds exist in food in both the free form
and bound to other food components due the nature of their chemical structures (Bravo, 1998). Four different forms of phenolic compounds have been reported in oil-seeds, including free, esterified,
etherified and insoluble bound phenolic acids (Aludatt, Rababah,
Ereifej, Brewer, & Alli, 2013; Dabrowski & Sosulski, 1984;
Kozlowska, Zadernowski, & Sosulski, 1983; Krygier, Sosulski, &
Hoggie, 1982; Naczk & Shahidi, 1989).
The nomenclature of phenolic acids depend on their chemical
compositions and structures. According to Shahidi and Naczk
(2004), phenylpropanoid and cinnamic acid derivatives are
referred to as phenolic acids. Fig. 1 shows the chemical structures
of the phenolic acids identified in oil-bearing plants. Flaxseed
contains phenylpropanoids, such as p-coumaric, o-coumaric, ferulic, p-hydroxybenzoic, vanillic and sinapic acids, in the free form.
However, p-coumaric acid glycoside, ferulic acid glucoside and

p-coumaric glucoside exist in bound forms (Aludatt, Rababah,

Ereifej, & Alli, 2013; Kozlowska et al., 1983). Dabrowski and
Sosulski (1984) reported that the levels of esterified, free and
bound phenolic compounds were 81 mg, 73.9 mg and
7.2 mg/100 g, respectively, in dehulled, defatted flaxseed meal.
Varga and Diosady (1994) reported a total phenolic content of
between 0.355 and 0.442 g/100 g in flaxseed meal, while insoluble
bound phenolic compounds composed 2629% of the total phenolic compounds. Oomah, Kenaschuk, and Mazza (1995) reported a
total phenolic content of 810 g/kg in flaxseed, and the esterified
phenolic acids composed approximately 4866% of the total phenolic compounds. Phenolic compounds that were not released after
extraction and alkaline hydrolysis were assumed to be etherbound phenolic compounds (Oomah et al., 1995). Tables 13 show
the distribution of total, esterified, free and bound phenolic acids in
flaxseed.
The level of free phenolic compounds in soybean flake was
25.6 mg/100 g (Maga & Lorenz, 1974), while Dabrowski and
Sosulski (1984) reported that soybean flour contains
73.6 mg/100 g of phenolic compounds. Kozlowska, Naczk,
Shahidi, and Zadernowski (1991) reported that the level of phenolic compounds was 0.23 mg/g (dry weight basis) in soybean flour,
and Naczk, Diosady, and Rubin (1986) reported that soybean meal
contains 4.6 mg/g of phenolic compounds. Ethanol extraction of
defatted soy flour revealed that syringic acid is the predominant
phenolic acid (Arai, Suzuki, Fujimaki, & Sakura, 1966). The major
phenolic compounds identified in soybean flour include ferulic,
syringic and vanillic acids (Lee et al., 2008; Maga & Lorenz,
1974). Dabrowski and Sosulski (1984) also reported that syringic
acid is the predominant free phenolic acid in soybean flour. However, How and Morr (1982) demonstrated that o-coumaric, p-coumaric and ferulic acid were also major phenolic acids. Maga and
Lorenz (1974) found a wide range of distribution of free phenolic
acids in soybeans, peanuts and cottonseed flours, with syringic, ferulic and vanillic acids being the major components. Tables 13
show the distribution of phenolic compounds in soybeans.
Sunflowers are considered to be an important source of oil with
considerable amounts of certain phenolic constituents. Chlorogenic acid has been reported to be the major phenolic acid in sunflower kernels, and they contain much lower levels of caffeic acid
(Mikolajczak, Smith, & Wolff, 1970). Tables 13 show the levels
of free and bound phenolic compounds in sunflower seeds.
Full-fat rapeseed flour contains 1030% higher levels of phenolic compounds than Oleaginous seeds. The levels of phenolic
compounds in defatted rapeseed meal are higher than those in
defatted soybean meal (Shahidi & Naczk, 1992). The phenolic compounds in rapeseed have been classified according to the occurrence of the free, esterified, and insoluble bound forms that are
derived from benzoic and cinnamic acids. The total content of
phenolic compounds in defatted rapeseed meal is 18.4 g/kg, while
full-fat rapeseed flour contains 6.212.8 g/kg (Naczk, Wanasundara,
& Shahidi, 1992). Sinapine, the major phenolic compound of rapeseed, has been shown to vary from 1.22.5% in defatted meal
(Austin & Wolff, 1968; Clandinin, 1961), depending on the location
and cultivars (Mueller, Ryl, Fenton, & Clandinin, 1978). Similarly,
wide ranges of sinapine values (0.41.8%) on a dry matter basis
were reported for several cultivars of Cruciferae crops, including
the Brassica species (Kerber & Buchloh, 1980). Kozlowska et al.
(1991) reported that rapeseed contains the following phenolic
compounds in free form: p-hydroxybenzoic acid, vanillic acid,
protocatechuic acid, syringic acid, p-coumaric acid, cis-and transferulic acid, caffeic acid and chlorogenic acid. Krygier et al.
(1982) reported that the predominant phenolic acids present in
rapeseed protein products are esterified phenolic acids and that
they consist of 80% of the total content of phenolic compounds.
Full-fat flours of rapeseed contain higher amounts of esterified

101

M.H. Aludatt et al. / Food Chemistry 218 (2017) 99106

Protocatechuic
Vanillic
Syringic
Gallic
p-Hydroxybenzoic

H
OCH3
OCH3
OH
H

OH
H
OCH3
OH
H

p-Coumaric
Caffeic
Ferulic
Sinapic

H
H
H
OCH3

H
OH
OCH3
OCH3

Tyrosol
Hydroxytyrosol
Verbascoside

H
OH
OH

OH
OH
Rhamnose

Oleuropein
Demethyloleuropein
Ligstroside

OH
OH
H

CH3
H
CH3

Fig. 1. Structures of phenolic acids (A, B, C and D) found in oil-bearing plants (Shahidi & Naczk, 2004).

Table 1
Distribution of phenolic compounds in different oil-bearing plants for different cultivars.
Phenolic Compounds (g/kg)
Oil-bearing Plant

Total

Free

Esterified

Insoluble Bound

Flaxseeda
Soybeanb
Rapeseedc
Olived

7.4610.55
1.432.25
6.3018.87
0.821.71

NR
NR
0.602.62
NR

4.795.42
NR
5.7015.20
NR

2.675.13
NR
0.001.05
NR

NR: Not Reported.

Sources:
a
Oomah and Mazza (1998).
b
Genovese, Hassimotto, and Lajolo (2005).
c
Kozlowska, Sabir, Sosulski, and Coxworth (1975); Kozlowska et al. (1983); Krygier et al. (1982); Naczk and Shahidi (1989).
d
Boskou et al. (2006).

102

M.H. Aludatt et al. / Food Chemistry 218 (2017) 99106

Table 2
Phenolic acids liberated from soluble esters of oil-seed flours (mg/100 g).
Phenolic Acid

Soybean

Flaxseed

Rapeseed

Sunflower

p-Hydroxybenzoic acid
Vanillic acid
Protocatechuic acid
Syringic acid
trans-p-Coumaric acid
trans-Ferulic acid
trans-Caffeic acid
cis-Sinapic acid
trans-Sinapic acid

13.00
0.00
0.00
26.40
9.40
14.50
5.20
0.00
0.00

2.60
Trace
0.00
0.40
4.90
33.30
3.60
0.00
29.10

5.60
0.70
Trace
1.10
Trace
15.00
Trace
33.00
1110.70

6.00
0.80
0.00
2.20
5.60
5.80
960.90
0.00
0.00

Total

68.50

73.90

1166.10

981.30

Source: Dabrowski and Sosulski (1984).

Table 3
Phenolic acids liberated from insoluble residues of oil-seed flours (mg/100 g).
Phenolic Acid

Rapeseed

Soybean

Flaxseed

Sunflower

p-Hydroxybenzoic acid
Syringic acid
trans-p-Coumaric acid
trans-Ferulic acid
trans-Caffeic acid

0.90
2.20
0.00
1.20
0.80

Trace
0.00
1.20
4.30
1.70

0.00
0.00
0.00
0.00
0.00

1.40
1.40
Trace
1.40
18.20

Total

5.10

7.20

0.00

22.40

Source: Dabrowski and Sosulski (1984).

phenolic acids compared to defatted meal (Krygier et al., 1982),

and this author reported that the predominant phenolic acid in
both rapeseed meal and flour is sinapic acid, which amounts to
7197% of the total phenolic acid liberated from esterified phenolic
acids. Pokorny and Reblova (1995) reported that sinapine, the choline ester of sinapic acid, is the most predominant phenolic choline
ester present in rapeseed flour and meal. Blair and Reichert (1984)
reported that the content of sinapine in defatted rapeseed and
canola is approximately 2.672.85%. Durkee and Thivierge (1975)
and Kozlowska et al. (1983) identified sinapic acid as the most predominant insoluble, bound phenolic compound in rapeseed flour,
consisting of 3059% of the total insoluble fraction of phenolic
compounds. The most abundant glycoside sinapate in rapeseed/canola was 1-O-b-D glucopyranosyl sinapate (Amarowicz,
Wanasundara, & Shahidi, 1994). Naczk and Shahidi (1989)
reported the content of insoluble bound phenolic compounds in
canola meal to be 1 g/kg. Kozlowska et al. (1983) found the content
of insoluble bound phenolic compounds in rapeseed/canola flour to
be 3250 mg/kg. Tables 13 show the distribution of phenolic
compounds in rapeseed. Simple phenolic compounds identified
in olive meals include tyrosol, hydroxytyrosol, gallic, protocatechuic, p-hydroxybenzoic, vanillic, caffeic, syringic, p-coumaric, ocoumaric, ferulic and cinnamic acids (Akasbi, Shoeman, &
Csallany, 1993; Montedoro, Servili, Baldioli, & Miniati, 1992a,
1992b).
Simple phenolic acids have the ability to strongly associate with
primary metabolites, such as proteins and carbohydrates (Vekey
et al., 1997). Table 1 shows the distribution of phenolic compounds
in olive meal. The major phenolic acids identified in olive meal
include hydroxycinnamic acid, hydroxybenzoic acid, hydroxycaffeic acid and hydroxyphenylacetic acid (Bianco & Uccella 2000;
Servili et al., 1999a, 1999b). Cinnamic acid and 2-4 (hydroxyphenyl) ethyl acetate have also been detected in olive oil
(Brenes-Balbuena, Garcia-Garcia, Rios, & Garrido, 1999).
Other phenolic compounds in olive oil include aglycons, which
are derived from oleuropein and ligstroside (Montedoro
et al., 1992a, 1992b). Oleuropein is an ester of 20 -(30 ,
40 -dihydroxyphenyl) ethanol (hydroxytyrosol and tyrosol) (SolerRivas, Espn, & Wichers, 2000) and belongs to a very specific group

of coumarin-like compounds that are referred to as secoiridoids,

which are abundant in the Oleaceas family. Secoiridoids, iridoids
and demethyloleuropein are compounds that are bound to glycoside (Bianco, Lo Scalzo, & Scarpati, 1993; Damtoft, Franzyk, &
Jensen, 1995). Oleuropein glycoside, aglycon and elenolic acid are
derived from the hydrolysis of oleuropein, as well as aglycons of
ligstroside and oleuropein (Montedoro et al., 1992a, 1992b).
Phenolic glucosides include verbascoside, which is a heterosidic
ester of caffeic acid and hydroxytyrosol (Owen et al., 2000;
Romani, Mulinacci, Pinelli, Vincieri, & Cimato, 1999). Hydroxytyrosol and tyrosol are the main phenolic compounds in extravirgin olive oil (Servili et al., 1999a, 1999b). Hydrophilic
extracts of olive oil contain many phenolic compounds and
phenyl-alcohols. The secoiridoid compounds identified in olive
oil include 3,4-dihydroxyphenylethanol, 4-hydroxyphenylethanol,
4-hydroxyphenylacetic acid, 3,5-dimethoxy-4-hydroxybenzoic
acid, 4-hydroxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid,
2-hydroxycinnamic
acid,
4-hydroxycinnamic
acid,
3,4dihydroxyphenylacetic acid and isomers of oleuropein (Amiot,
Fleuriet, & Macheix, 1986; Bianco et al., 1993; Brenes-Balbuena,
Garcia-Garcia, & Garrido-Fernandez, 1992). Oleuropein, hydroxytyrosol and their derivatives are found in large quantities in olive
leaves and olive fruits (Servili et al., 1999a, 1999b). Fig. 1 shows
the structures of some phenolic compounds in olive meal. Bianco
and Uccella (2000) reported the presence of hydroxyisochromans
and their derivatives in olives.
2.2. Polyphenol compounds
The condensation of more than one unit of phenylpropanoides
(C6-C3) leads to the formation of flavonoids that have a basic
skeleton of diphenylpropanes (C6-C3-C6). These include flavones,
isoflavones and anthocynidins (Shahidi & Naczk, 2004). The total
content of flavonoids in flaxseed is 3571 mg/100 g (Oomah,
Mazza, & Kenaschuk, 1996), and the major flavonoids in flaxseed
are C-glycosides and O-glycosides (Ibraham & Shaw, 1970).
Huang, Hseih, and Chang (1979) reported that the isoflavone group
consists of daidzein (7,40 -dihydroxyisoflavone),
glycitein
(7,40 - dihydroxy-6-methylisoflavone) and genistein (6,7,40 trihy-

M.H. Aludatt et al. / Food Chemistry 218 (2017) 99106

103

Fig. 2. Structures of complex phenolic compounds, including tannic acid and condensed tannin, in oil-bearing plants (Bravo, 1998), flaxseed lignans (secoisolariciresinol and
matairesinol) (Meagher et al., 1999), olive lignans (pinoresinol and acetoxypinoresinol) (Owen et al., 2000) and soybean isoflavones (daidzein, glycitein and genistein)
(Shahidi & Naczk, 2004).

droxyisoflavone) (Fig. 2). These daidzein, glycitein and genistein

isoflavones are present in soybeans as glucosides, malonylglucosides (malonyldaidzein, malonylglycitein and malonylgenistein),
acetylglucosides, (acetyldaidzein, acetylglycitein and acetylgenistein), isoformononetin, trihydroxyisoflavone, dihydrodaidzin and
dihydrogenistein (Barnes, Kirk & Coward, 1994; Gyorgy, Murata,
& Ikehata, 1964; Hoeck, Fehr, Murphy, & Welke, 2000; Hosny &
Rosazza, 2002; Ingham, Keen, Mulheirn, & Lyne, 1981; Kudou
et al., 1991; Liu et al. 2016). Cyanidin-3-glucoside, a major anthocyanin, was identified by Kuroda and Wade (1993) in soybeans.
Isoflavonoid phytoalexins, such as coumestrol, have been identified in soybeans, and the coumestrol content of soybeans is
0.127.11 mg/100 g (Knuckles, de Fremery, & Kohler, 1976). The
content of polyphenols in olive fruits is approximately
80 mg/100 g (Visioli et al., 2000), depending on the cultivar, season, location and degree of ripening (Amiot et al., 1986). The flavonoids identified in olive meal and olive oil include rutin, quercetin,
luteolin-7-glucosides and apigenin glucosides (Amiot et al., 1986;
Brenes-Balbuena et al., 1999).
Tannins are classified according to their chemical structures
into hydrolyzable tannins (tannic acid) and condensed tannins
(proanthocyanidins). Hydrozable tannins consist of gallic acid
and its dimeric condensation product, hexahydroxydiphenolic acid
esterified to a polyol, which is mainly glucose (Fig. 2). It is a gallotannin consisting of a pentagalloyl glucose molecule that can
be further esterified to form five gallic acid units (Porter, 1989).
Condensed tannins have been identified in rapeseed hulls (BateSmith & Ribereau-Gayon, 1959). The content of tannins in rapeseed
meal is 3% (Clandinin & Heard, 1968). Blair and Reichert (1984)

reported the content of tannins to be between 0.09 and 0.39% in

defatted rapeseed cotyledons and between 0.23 and 0.54% in defatted canola cotyledons. Canola meal consists of 0.68 to 0.77% condensed tannins (Shahidi & Naczk, 1988; Shahidi & Naczk, 1989).
The total tannin content in rapeseed/canola hull is 0.1423 g/kg,
and the crude tannin extract from canola hull consists of 20%
proanthocyanidins (Naczk, Nichols, Pink, & Sosulskill, 1994).
2.3. Lignans
Lignans are phytochemicals that are formed by the combination
of two units of phenylpropanoids (C6-C3) linked by the central
carbon of their side chain in the plant cell wall. They have been
classified into four major groups: lignans, lignolides, monoepoxylignans and biepoxylignans (Shahidi and Naczk, 2004). Flaxseed is considered to be a good source of lignan, with over 800
times more lignan than any other plant (Pszczola, 2002). Secoisolariciresinol and other phenolic compounds in flaxseed are found
in both glucosidic- and ester-bound forms (Bambagiotti-Alberti,
Coran, Ghiara, Giannellini, & Raffaelli, 1994). Plant lignans, such
as matairesinol and secoisolariciresinol diglucoside (SDG), have
been shown to be precursors of mammalian lignans, which are
produced in the colon by the bacterial flora (Thompson, Robb,
Serraino, & Cheung, 1991). SDG is a major component of lignan,
and defatted flaxseed consists of 14% lignans (Bakke &
Klosterman, 1956). The most important mammalian lignans are
enterolactone and enterodiol, which are generated by the removal
of two methyl groups and two hydroxyl groups from matairesinol
and SDG, respectively (Qiu et al., 1999). Matairesinol is present in

104

M.H. Aludatt et al. / Food Chemistry 218 (2017) 99106

flaxseed in relatively low amounts compared to SDG (Mazur &

Adlercreutz, 1998). Other lignans found in flaxseed include the isomer of SDG, isolariciresinol and pinoresinol diglucoside
(Bambagiotti-Alberti et al., 1994; Meagher, Beecher, Flanagan, &
Li, 1999; Qiu et al., 1999). The lignans found in olive oil include
pinoresinol, 1-acetoxypinoresinol and pinoresinol diglucoside.
The content of pinoresinol and 1-acetoxypinoresinol in olive oil
is approximately 567 mg/kg (Brenes-Balbuena et al., 1999; Qiu
et al., 1999). Fig. 2 shows the structures of lignans in oil-bearing
plants.

ciresinol levels were analyzed by HPLC using UV detection

(Meagher et al., 1999). Bambagiotti-Alberti et al. (1994) used LCMS methods to analyze samples without using derivatization.
The sensitivity and selectivity of detection could be increased by
using a coulometric electrode array detector (Nurmi &
Adlercreutz, 1999). Separations of the lignan were analyzed with
a high performance liquid chromatography/diode array detection
system using a C-18 column (Obermeyer et al., 1995).

2.4. Extraction, separation and determination of phenolics

Many assay methods based on the determination of the primary

and secondary products of the autoxidation of lipids have been
used for the evaluation of total antioxidant activity, such as colorimetric, spectrophotometric, electrochemical or chromatographic
techniques (Alhakmani et al., 2013; Shahidi & Naczk, 2004;
Wong-Paz et al., 2015). The different techniques that have been
reported to measure antioxidant activity include ABTS, DPPH,
FRAP, beta-carotene-linoleic and ORAC assays (Aludatt et al.,
2016; Dini, Tenore, & Dini, 2013; Luthria, 2012). Antioxidant activities are measured using different methods under normal conditions, such as storage, temperature and metal ions, or under
certain conditions designed to increase the rate of oxidation, such
as the Active Oxygen Species Method, Schaal Oven Test, Oxygen
Bomb Calorimetry, use of oxidative stability instruments, Rancimat
Method, Oxidograph Method and use of a luminescence apparatus
(Alhakmani et al., 2013; Wong-Paz et al., 2015).

The levels of phenolic compounds in oil-bearing plants have

recently been measured using the Folin-Ciocalteu colorimetric
method (Hoff & Singleton, 1977). According to reports in the literature, many solvents have been used to extract phenolic compounds from samples, including mixtures of the solvents
methanolwater, water, methanol, and tetrahydrofuran-water
(Alhakmani, Kumar, & Khan, 2013; Shahidi & Naczk, 2004;
Wong-Paz et al., 2015).
Different analytical methods have been identified based on the
determination of both the naturally occurring phenolic compounds
and the polyphenol compounds (Mazur & Adlercreutz, 1998;
Obermeyer et al, 1995; Wong-Paz et al., 2015). Two main extraction techniques have been reported in the literature: liquidliquid
extraction (Montedoro et al., 1992a, 1992b) and solid-phase
extraction (Pirisi, Cabras, Falqui Cao, Migliorini, & Muggelli, 2000;
Wong-Paz et al., 2015). High-performance liquid chromatography
(HPLC) and gas chromatography (GC) have been used for the separation and determination phenolic compounds (Liu et al., 2016).
Analysis of the phenolic compounds in virgin olive oil is currently
performed by HPLC (Alhakmani et al., 2013; Montedoro et al.,
1992a, 1992b; Wong-Paz et al., 2015).
Simple and complex phenolic compounds have been detected
by HPLC using UV, a diode array or electrochemical detectors
(Montedoro et al., 1992a, 1992b; Pirisi et al., 2000; Romani et al.,
1999). The extracted phenolic compounds have been fractionated
using classical low-pressure column chromatography on Sephadex
columns (Janiak et al., 2014; Montedoro et al., 1992a, 1992b). Multiple mobile phases have been employed with different modifiers
(methanol, acetonitrile or tetrahydrofuran), acids (acetic or formic
acid) and salts (ammonium phosphate). Thin layer chromatography (TLC), nuclear magnetic resonance (NMR), capillary electrophoresis (CE), capillary zone electrophoresis (CZE) and HPLC
have been used to analyze phenolic compounds (Pirisi et al.,
2000). Many techniques to remove and extract polyphenols from
the by-products of flaxseeds and others seeds have been reported,
such as high voltage electrical discharges, coagulation and ultrafiltration techniques (Boussetta, Vorobiev, Le, Cordin-Falcimaigne, &
Lanoisell, 2012; Boussetta et al., 2011; Loginov, Boussetta,
Lebovka, & Vorobiev, 2013). More recently, maceration, solidphase extractions and ultrasound-assisted solid liquid extractions
have been developed to extract and separate individual phenolic
compounds from olive fruit (Alarcn Flores, Romero-Gonzlez,
Garrido Frenich, & Martnez Vidal, 2012; Ansari, Kazemipour, &
Fathi, 2011; Jerman, Trebe, & Mozetic Vodopivec, 2010).
Simple phenolic compounds can be separated and quantified by
GC based on the derivatization process, while HPLC methods are
commonly used to omit the derivatization step of sample preparation. GC-Mass spectrophotometer (GCMS) detection of derivatized phenolic compounds has been reported (Angerosa,
dAlessandro, Konstantinou, & Di Giacinto, 1995). Recently,
Liggins, Bluck, and Runswick (2000) identified secoisolariciresinol
and matairesinol in food samples after hydrolysis was used to
break the conjugated compounds by GCMS. The secoisolari-

2.5. Antioxidant activity measurements

3. Summary
Oilseeds are considered to be good sources of oil, proteins and
phenolic compounds. Phenolic compounds have been studied
extensively due to their therapeutic and antioxidant properties.
There has been nutritional interest regarding the deleterious
effects of phenolic compounds caused by the ability of certain phenolic compounds to bind with macromolecules, such as proteins
and carbohydrates. Variations in the organoleptic, nutraceutical,
therapeutic, functional and pharmaceutical properties of oilseeds
are due to variations in the types, contents and metabolic properties of phenolic compounds. Two major groups of simple and complex phenolic compounds have been identified in oil-bearing
plants. In some cases, the functional properties of oil are influenced
by the interactions of individual food components with phenolic
compounds. This review revealed that there are no optimal extraction conditions for phenolic compounds due to the wide range of
polarity of phenolic compounds in oil-seed plants.
References
Akasbi, M., Shoeman, D. W., & Csallany, A. S. (1993). High-performance liquid
chromatography of selected phenolic compounds in olive oils. Journal of
American Oil Chemical Society, 70, 367370.
Alarcn Flores, M. I., Romero-Gonzlez, R., Garrido Frenich, A., & Martnez Vidal, J. L.
(2012). Analysis of phenolic compounds in olive oil by solid-phase extraction
and ultra high performance liquid chromatographytandem mass
spectrometry. Food Chemistry, 134, 24652472.
Alhakmani, F., Kumar, S., & Khan, S. A. (2013). Estimation of total phenolic content,
in-vitro antioxidant and anti-inflammatory activity of flowers of Moringa
oleifera. Asian Pacific Journal of Tropical Biomedcine, 3(8), 623627.
Aludatt, M. H., Rababah, T., & Alli, I. (2014). Effect of phenolic compound removal
on rheological, thermal and physico-chemical properties of soybean and
flaxseed proteins. Food Chemistry, 146, 608613.
Aludatt, M. H., Rababah, T., Ereifej, K., & Alli, I. (2013). Distribution, antioxidant and
characterisation of phenolic compounds in soybeans, flaxseed and olives. Food
Chemistry, 139, 9399.
Aludatt, M. H., Rababah, T., Ereifej, K., Brewer, S., & Alli, I. (2013). Phenolic-protein
interactions in oilseed protein isolates. Food Research International, 52(1),
178184.
Aludatt, M. H., Rababah, T., Alhamad, M. N., Gammoh, S., Ereifej, K., Kubow, S., et al.
(2016). Characterization and antioxidant activities of phenolic interactions

M.H. Aludatt et al. / Food Chemistry 218 (2017) 99106

identified in byproducts of soybean and flaxseed protein isolation. Food
Hydrocolloids, 61, 119127.
Amarowicz, R., Wanasundara, U., & Shahidi, F. (1994). Chromatographic separation
of flaxseed phenolics. Nahrung, 38, 520526.
Amiot, M. J., Fleuriet, A., & Macheix, J. J. (1986). Importance and evolution of
phenolic compounds in olive during growth and maturation. Journal of
Agricultural and Food Chemistry, 34, 823826.
Angerosa, F., dAlessandro, N., Konstantinou, P., & Di Giacinto, L. (1995). GC-MS
evaluation of phenolic compounds in virgin olive oil. Journal of Agricultural and
Food Chemistry, 43, 18021807.
Ansari, M., Kazemipour, M., & Fathi, S. (2011). Development of a simple green
extraction procedure and HPLC method for determination of oleuropein in olive
leaf extract applied to a multi-source comparative study. Journal of the Iranian
Chemical Society, 8, 3847.
Arai, S., Suzuki, H., Fujimaki, M., & Sakurai, Y. (1966). Flavour compounds in
soybean. II. Phenolic acids in defatted soybean flour. Agricultural and Biological
Chemistry, 30, 364369.
Austin, F. L., & Wolff, I. A. (1968). Sinapine and related esters in seed meal of Crambe
abyssinica. Journal of Agricultural and Food Chemistry, 16, 132135.
Bakke, J. E., & Klosterman, H. J. (1956). A new diglucoside from flaxseed. Proceeding
of The North Dakota Academy of Science, 10, 1822.
Bambagiotti-Alberti, M., Coran, S. A., Ghiara, C., Giannellini, V., & Raffaelli, A. (1994).
Revealing the mammalian lignan precursor secoisolariciresinol diglucoside in
flax seed by ion spray mass spectrometry. Rapid Communications in Mass
Spectrometry, 8, 595598.
Barnes, S., Kirk, M., & Coward, L. (1994). Isoflavones and their conjugates in soy
foods: Extraction conditions and analysis by HPLC-mass spectrometry. Journal
of Agricultural and Food Chemistry, 42, 24662474.
Bate-Smith, E. C., & Ribereau-Gayon, P. (1959). Leucoanthocyanins in seeds. Quality
Plant Material Vegetable, 5, 189198.
Bianco, A., Lo Scalzo, R., & Scarpati, M. L. (1993). Isolation of cornoside from
Olea europaea and its transformation into halleridone. Phytochemistry, 32,
455457.
Bianco, A., & Uccella, N. (2000). Biophenolic components of olives. Food Research
International, 33, 475485.
Blair, R., & Reichert, R. D. (1984). Carbohydrate and phenolic constituents in a
comprehensive range of rapeseed and canola fractions: Nutritional significant
for animals. Journal of the Science of Food and Agriculture, 35, 2935.
Boskou, G., Salta, F. N., Chrysostomou, S., Mylona, A., Chiou, A., & Andrikopoulos, N.
K. (2006). Antioxidant capacity and phenolic profile of table olives from the
Greek market. Food Chemistry, 94, 558564.
Boussetta, N., Vorobiev, E., Deloison, V., Pochez, F., Falcimaigne-Cordin, A., &
Lanoisell, J.-L. (2011). Valorisation of grape pomace by the extraction of
phenolic antioxidants: application of high voltage electrical discharges. Food
Chemistry, 128, 364370.
Boussetta, N., Vorobiev, E., Le, L. H., Cordin-Falcimaigne, A., & Lanoisell, J.-L. (2012).
Application of electrical treatments in alcoholic solvent for polyphenols
extraction from grape seeds. LWTFood Science and Technology, 46, 127134.
Bravo, L. (1998). Polyphenols: chemistry, dietary sources, metabolism, and
nutritional significance. Nutrition Reviews, 56, 317333.
Brenes-Balbuena, M., Garcia-Garcia, P., & Garrido-Fernandez, A. (1992). Phenolic
compounds related to the black color formed during the processing of ripe
olives. Journal of Agricultural and Food Chemistry, 40, 11921196.
Brenes-Balbuena, M., Garcia-Garcia, P., Rios, J. J., & Garrido, A. (1999). Phenolic
compounds in spanish olive oils. Journal of Agricultural and Food Chemistry, 47,
35353540.
CETIOM, (2014). Composition of oilseeds and meals [Online]. Available on: <http://
www.cetiom.fr/uploads/tx cetiomlists/qualite graines colza recolte 2014. pdf/>
(accessed 18.03.15.).
Clandinin, D. R. (1961). Rapeseed oil meal studies. IV. Effect of sinapin, the bitter
substance in rapeseed oil meal, on the growth of chickens. Poultry Science, 40,
484487.
Clandinin, D., & Heard, J. (1968). Tannins in prepress-solvent and solvent-processed
rapeseed meal. Poultry Science, 47, 688689.
Dabrowski, K., & Sosulski, F. (1984). Composition of free and hydrolyzable phenolics
acids in defatted flours of ten oilseeds. Journal of Agricultural and Food Chemistry,
32, 128130.
Damtoft, S., Franzyk, H., & Jensen, S. R. (1995). Biosynthesis of secoiridoids in
fontanesia. Phytochemistry, 38, 615621.
Dini, I., Tenore, G. C., & Dini, A. (2013). Effect of industrial and domestic processing
on antioxidant properties of pumpkin pulp. LWTFood Science and Technology,
53, 382385.
Durkee, A., & Thivierge, P. (1975). Bound phenolic acids in Brassica and sinapic
oilseeds. Journal of Food Science, 40, 820822.
Fine, F. L., Chardigny, J., Redlingshfer, B., & Renard, M. (2015). Food losses and
waste in the French oil crops sector. Oilseeds and Fats Crops and Lipids, 22(3),
A302.
Genovese, M. I., Hassimotto, N. M. A., & Lajolo, F. M. (2005). Isoflavone profile and
antioxidant activity of Brazilian soybean varieties. Food Science and Technology
International, 11, 205211.
Gyorgy, P., Murata, K., & Ikehata, H. (1964). Antioxidants isolated from fermented
soybeans (tempeh). Nature, 203, 870872.
Herchi, W., Arrez-Romn, D., Trabelsi, H., Bouali, I., Boukhchina, S., Kallel, H., et al.
(2014). Phenolic compounds in flaxseed: a review of their properties and
analytical methods. An overview of the last decade. Journal of Oleo Science, 63
(1), 714.

105

Hoeck, J. A., Fehr, W. R., Murphy, P. A., & Welke, G. A. (2000). Influence of genotype
and environment on isoflavone contents of soybean. Crop Science, 40,
4851.
Hoff, J. E., & Singleton, K. I. A. (1977). Method for determination of tannins in foods
by means of immobilized protein. Journal of Food Science, 42, 15661569.
Hosny, M., & Rosazza, J. P. (2002). New isoflavone and triterpene glycosides from
soybeans. Journal of Natural Product, 65, 805813.
How, J. S. L., & Morr, C. V. (1982). Removal of phenolic compounds from soy protein
extracts using activated carbon. Journal of Food Science, 47, 933940.
Huang, A. S., Hseih, O., & Chang, S. S. (1979). Charcterization of nonvoltile constituents
responsiple for bitter and astringent taste in soybean protein. MO, USA: Annual
Meeting of the Institue of Food Technologist.
Ibraham, R. K., & Shaw, M. (1970). Phenolic constituents of oil flax (linum
usitatissimum). Phytochemistry, 9, 18551858.
Ingham, J. L., Keen, N. T., Mulheirn, L. J., & Lyne, R. L. (1981). Inducibly-formed
isoflavonoids from leaves of soybean. Phytochemistry, 20, 795798.
Janiak, M., Slavova-Kazakova, A., Kancheva, V., & Amarowicz, R. (2014). Sephadex
LH-20 column chromatography of the hydrolysed lignan macromolecule of
flaxseed. Bulgarian Chemical Communications, 46, 640644.
Jerman, T., Trebe, P., & Mozetic Vodopivec, B. (2010). Ultrasound-assisted solid
liquid extraction (USLE) of olive fruit (Olea europaea) phenolic compounds. Food
Chemistry, 123, 175182.
Kerber, E., & Buchloh, G. (1980). The sinapine content Crucifer seeds. Angewandte
Botanik, 54, 4754.
Khattab, R. Y., Eskin, M. N. A., & Thiyam-Hollander, U. (2014). Production of
canololfrom canola meal phenolics via hydrolysis and microwave-induced
decarboxylation. Journal of American Oil Chemical Society, 91, 8997.
Knuckles, B. E., de Fremery, D., & Kohler, G. O. (1976). Coumestrol content of
fractions obtained during wet processing of alfalfa. Journal of Agricultural and
Food Chemistry, 24, 11771180.
Kozlowska, H., Naczk, M., Shahidi, F., & Zadernowski, R. (1991). Phenolic acids and
tannins in rapeseed and canola. In F. Shahidi (Ed.), Canola and rapeseed:
Production, chemistry, nutrition and processing technology (pp. 193210). New
York, NY: AVI Book.
Kozlowska, H., Sabir, M. A., Sosulski, F. W., & Coxworth, E. (1975). Phenolic
constituents in rapeseed flour. Canadian Institute of Food Science and Technology
Journal, 8, 160163.
Kozlowska, H., Zadernowski, R., & Sosulski, F. W. (1983). Phenolic acids in oilseed
flours. Nahrung, 27, 449453.
Krygier, K., Sosulski, F., & Hoggie, I. (1982). Free, esterified, and insoluble-bound
phenolic acids. Composition of phenolic acids in rapeseed flour and hulls.
Journal of Agricultural and Food Chemistry, 30, 334336.
Kudou, S., Fleury, Y., Welti, D., Magnolato, D., Uchida, T., Kitamura, K., & Okubo, K.
(1991). Malonyl isoflavone glycosides in soybean seeds (Glycine max M.).
Agricultural and Biological Chemistry, 55, 22272233.
Kuroda, C., & Wade, M. (1993). The coloring matter of kuro-mame. Proceedings of the
Imperial Academy (Tokyo), 9, 1718.
Lee, S. J., Kim, J. J., Moon, H. I., Ahn, J. K., Chun, S. C., Jung, W. S., et al. (2008). Analysis
of isoflavones and phenolic compounds in Korean soybean [glycine max (l.)
Merrill] seeds of different seed weights. Journal of Agricultural and Food
Chemistry, 56, 27512758.
Liggins, J., Bluck, L. J. C., Runswick, S., Atkinson, C., Coward, W. A., & Bingham, S. A.
(2000). Daidzein and genistein content of fruits and nuts. Journal of Nutritional
Biochemistry, 11, 326331.
Liu, J., Yang, C. Q., Zhang, Q., Lou, Y., Wu, H. J., Deng, J. C., et al. (2016). Partial
improvements in the flavor quality of soybean seeds using intercropping
systems with appropriate shading. Food Chemistry, 207, 107114.
Loginov, M., Boussetta, N., Lebovka, N., & Vorobiev, E. (2013). Separation of
polyphenols and proteins from flaxseed hull extracts by coagulation and
ultrafiltration. Journal of Membrane Science, 442, 177186.
Luthria, D. L. (2012). A simplified UV spectral scan method for the estimation of
phenolic acids and antioxidant capacity in eggplant pulp extracts. Journal of
Functional Foods, 4, 38242.
Maga, J. A., & Lorenz, K. (1974). Gas-liquid chromatography separation of the free
phenolic acid fractions in various oilseed protein sources. Journal of the Science
of Food and Agriculture, 25, 797802.
Mazur, W., & Adlercreutz, H. (1998). Natural and anthropogenic environmental
estrogens: The scientific basis for risk assessment. Naturally occurring
estrogens in food. Pure and Applied Chemistry, 70, 17591776.
Meagher, L. P., Beecher, G. R., Flanagan, V. P., & Li, B. W. (1999). Isolation and
characterization of the lignans, isolariciresinol and pinoresinol, in flaxseed
meal. Journal of Agricultural and Food Chemistry, 47, 31733180.
Mikolajczak, K. L., Smith, C. J., & Wolff, I. A. (1970). Phenolic and sugar components
of Armavireo variety sunflower (Helianthus annuus) seed meal. Journal of
Agricultural and Food Chemistry, 18, 2732.
Montedoro, G., Servili, M., Baldioli, M., & Miniati, E. (1992a). Simple and
hydrolysable phenolic compounds in virgin olive oil. 1. Their extraction,
separation, and quantitative and semi quantitative evaluation by HPLC.
Journal of Agricultural and Food Chemistry, 40, 15711576.
Montedoro, G., Servili, M., Baldioli, M., & Miniati, E. (1992b). Simple and
hydrolyzable phenolic compounds in virgin olive oil. 2. Initial characterization
of the hydrolyzable fraction. Journal of Agricultural and Food Chemistry, 40,
15771580.
Mueller, M. M., Ryl, E. B., Fenton, T., & Clandinin, D. R. (1978). Cultivar and growing
location differences on the sinapine content of rapeseed. Canadian Journal of
Animal Science, 58, 579583.

106

M.H. Aludatt et al. / Food Chemistry 218 (2017) 99106

Naczk, M., Diosady, L. L., & Rubin, L. J. (1986). The phytate and complex phenol
content of meals produced by alkanol-ammonia/hexane extraction of canola.
Lebensmittelwissen and Technogie, 19, 1316.
Naczk, M., Nichols, T., Pink, D., & Sosulskill, F. (1994). Condensed tannins in canola
hulls. Journal of Agricultural and Food Chemistry, 42, 21962200.
Naczk, M., & Shahidi, F. (1989). The effect of methanol-ammonia-water treatment
on content of phenolic acid of canola. Food Chemistry, 31, 159164.
Naczk, M., Wanasundara, P., & Shahidi, F. (1992). Facile spectroscopic determination
of sinapine acid in Brassica seeds. Journal of Agricultural and Food Chemistry, 40,
444448.
Nurmi, T., & Adlercreutz, H. (1999). Sensitive high-performance liquid
chromatographic method for profiling phytoestrogens using coulometric
electrode array detection: Application to plasma analysis. Analytical
Biochemistry, 274, 110117.
Obermeyer, W. R., Musser, S. M., Betz, J. M., Casey, R. E., Pohland, A. E., & Page, S. W.
(1995). Chemical studies of phytoestrogens and related compounds in dietary
supplements: Flax and chaparral. Proceedings of the Society for Experimental
Biology and Medicine, 208, 612.
Oomah, B. D., Kenaschuk, E. O., & Mazza, G. (1995). Phenolic acids in flaxseed.
Journal of Agricultural and Food Chemistry, 43, 20162019.
Oomah, B. D., Mazza, G., & Kenaschuk, E. O. (1996). Flavonoids content in flaxseed.
Influence of cultivar and environment. Euphytica, 90, 163167.
Oomah, B. D., & Mazza, G. (1998). Flaxseed products for disease prevention. In G.
Mazza (Ed.), Functional foods: Biochemical and processing aspects (pp. 91138).
Lanchester, PA, USA: Technomic Pub Co Inc.. Chapter 4.
Owen, R. W., Mier, W., Giacosa, A., Hull, W. E., Spiegelhalder, B., & Bartsch, H. (2000).
Phenolic compounds and squalene in olive oils: The concentration and
antioxidant potential of total phenols, simple phenols, secoiridoids, lignans
and squalene. Food and Chemical Toxicology, 38, 647659.
Pirisi, F. M., Cabras, P., Falqui Cao, C., Migliorini, M., & Muggelli, M. (2000). Phenolic
compounds in virgin olive oil. 2. Reappraisal of the extraction, HPLC separation,
and quantification procedures. Journal of Agricultural and Food Chemistry, 48,
11911196.
Pokorny, J., & Reblova, Z. (1995). Sinapines and other phenolics of Brasicaceae seeds.
Potravinarske Vedy, 13, 155168.
Porter, L. J. (1989). Tannins. In P. M. Dey & J. B. Harborne (Eds.), Methods in plant
biochemistry (pp. 389419). London: Academic Press.
Pszczola, D. E. (2002). Evolving ingredient components offer specific health value.
Food Technology, 56, 5056.

Qiu, S., Lu, Z., Luyengi, L., Lee, S. K., Pezzuto, J. M., Farnsworth, N. R., et al. (1999).
Isolation and characterization of flaxseed (Linum usitatissimum) constituents.
Pharmaceutical Biology, 37, 17.
Romani, A., Mulinacci, N., Pinelli, P., Vincieri, F. F., & Cimato, A. (1999). Polyphenolic
content in five tuscany cultivars of Olea europaea L. Journal of Agricultural and
Food Chemistry, 47, 964967.
Servili, M., Baldioli, M., Selvaggini, R., Miniati, E., Macchioni, A., & Montedoro, G. F.
(1999a). High-performance liquid chromatography evaluation of phenols in
olive fruit, virgin olive oil, vegetation waters, and pomace and 1D- and 2Dnuclear magnetic resonance characterization. Journal of American Oil Chemical
Society, 76, 873882.
Servili, M., Baldioli, M., Selvaggini, R., Miniati, E., Macchioni, A., & Montedoro, G. F.
(1999b). Phenolic compounds of olive fruit: One and two-dimensional nuclear
magnetic resonance characterization of nuezhenide and Its distribution in the
constitutive parts of fruit. Journal of Agricultural and Food Chemistry, 47, 1218.
Shahidi, F., & Naczk, M. (1988). Effect of processing on the phenolic constituents of
canola. Bulletin de Liaison-Groupe Polyphenols, 14, 8992.
Shahidi, F., & Naczk, M. (1989). Effect of processing on the content of condensed
tannins in rapeseed meals. Journal of Food Science, 54, 10821083.
Shahidi, F., & Naczk, M. (1992). An overview of the phenolics of canola and
rapeseed: Chemical, sensory and nutritional implications. Journal of American
Oil Chemical Society, 69, 917924.
Shahidi, F., & Naczk, M. (2004). Phenolic in food and nutraceutical (pp. 1558). Boca
Raton: CRC Press, Flordia, USA.
Shim, Y. Y., Gui, B., Arnison, P. G., Wang, Y., & Reaney, M. J. T. (2014). Flaxseed (Linum
usitatissimum L.) bioactive compounds and peptide nomenclature: A review.
Trends in Food Science and Technology, 1, 520.
Thompson, L. U., Robb, P., Serraino, M., & Cheung, F. (1991). Mammalian lignan
production from various foods. Nutrition Cancer, 16, 4352.
Vekey, K., Malorni, A., Pocsfalvi, G., Piperno, A., Romeo, G., & Uccella, N. (1997).
Biophenol-protein supramolecular models by fast atom bombardment-mass
spectrometric experiments. Journal of Agricultural and Food Chemistry, 45,
24472451.
Visioli, F., Galli, C., Bernet, F., Mattei, A., Patelli, R., Galli, G., et al. (2000). Olive oil
phenolics are dose dependent absorbed in humans. FEBS Letters, 468, 159160.
Wong-Paz, J. E., Contreras-Esquivel, J. C., Rodrguez-Herrera, R., Carrillo-Inungaray,
M. L., Lpez, L. I., Nevrez-Moorilln, G. V., et al. (2015). Total phenolic content,
in vitro antioxidant activity and chemical composition of plant extracts from
semiarid Mexican region. Asian Pacific Journal of Tropical Biomedcine, 8, 104111.