Amaranth Seed Oil Composition

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Chapter
Amaranth Seed Oil Composition
ParisaNasirpour-Tabrizi, SodeifAzadmard-Damirchi,
JavadHesari and ZahraPiravi-Vanak
Abstract
In this chapter, amaranth seed oil composition will be presented. The main
component of this oil is triacylglycerols (TAGs). TAGs are composed of fatty acids,
which have an important effect on oil stability, application, and nutritional proper-
ties. POL, PLL, POO, OLL, and LOO are the predominant TAGs in the amaranth
seed oil. Linoleic acid (C18:2), oleic acid (C18:1), and palmitic acid (C16:0) are the
predominant fatty acids present in the amaranth oil. Minor components of this oil
are squalene, sterols, tocopherols, carotenoids, phospholipids, etc. Growth condi-
tions of amaranth and extraction conditions can influence oil composition, which
will be discussed in this chapter as well. Oil stability and quality parameters will be
also discussed. The stability of this oil during different conditions of storage will be
a part of this chapter.
Keywords: triacylglycerol, fatty acid, squalene, tocopherol, sterol
. Introduction
Grain amaranth is considered as a gluten-free pseudocereal, which is a non-grass
but cereal-like grain (true cereals are classified as grasses). It is suitable to be used as
the celiac disease patient diet as it contains no gluten [1]. Among more than 60 spe-
cies, the grain of Amaranthus caudatus, Amaranthus hypochondriacus, Amaranthus
cruentus, Amaranthus hybridus, and Amaranthus mantegazzianus can be used as
flour in some industries, such as bakery and confectionery. However, species of
Amaranthus retroflexus, Amaranthus viridis, and Amaranthus spinosus are not safe to
be consumed [2].
The amaranth grain is mainly composed of about 61.3–76.5% carbohydrate
(mostly starch), 13.1–21.5% crude protein, 5.6–10.9% crude fat, 2.7–5% crude
fiber, and 2.5–4.4% ash [3]. Proteins and lipids are two nutritiously important
macromolecules of the amaranth grain. The content and even the quality of these
two macronutrients are different from those with cereals. The amaranth grain has
higher protein content in comparison to cereals. Lysine, which is the limiting amino
acid in cereals, is found in higher amounts in amaranth grain. The high protein
content of the amaranth grain is also evident from its high essential amino acid
index (EAAI=90.4%), which makes it comparable with egg protein [4].
In addition to protein content and special amino acid profile, amaranth grain
usually contains 5–8% fat, which is important from the nutritional aspect [5].
However, spinosus and tenuifolius species can contain oil content as much as 17 and
19.3%, respectively. The fat content of the amaranth grain is dependent on the spe-
cies, cultivars, and also accessions [6].

Nutritional Value of Amaranth

The fat content of amaranth grain is two to three times higher than cereals [7].
The oil is usually extracted from the grain by the solvent extraction method with the
help of a non-polar organic solvent in a Soxhlet apparatus [8]. Supercritical carbon
dioxide can be used as an alternative to traditional organic solvents for the extrac-
tion of the oil (supercritical fluid extraction method) [9, 10]. In the accelerated
solvent extraction method, high pressure and temperature (even above the boiling
point of the organic solvent) are used [6]. The oil yield with the Soxhlet method
(62.1–75.7%) and accelerated solvent extraction method (65.1–78.1%) is almost
similar; however, the latter is faster and uses lower organic solvent. The supercriti-
cal fluid extraction method has the lowest oil yield among the three methods
(54.6–61.1%) [8].
Lipid fraction is mainly composed of triacylglycerols (TAGs) as the major
component (around 80%) and other minor compounds, such as squalene, sterols,
tocopherols, carotenoids, phospholipids, etc. [11]. Lipid fraction can also be divided
into two groups: free lipids and bonded lipids. TAGs are the major free lipids, while
phospholipids (up to 10.2% of total lipids) and glycolipids (6.4% of total lipid frac-
tion) comprise the main part of the bounded lipids [11].
. Triacylglycerol profile
TAGs are the major component of the amaranth oil, comprising 78–82% of the
lipid fraction [11, 12]. Di- and monoacylglycerols comprise 5.1–6.5 and 3–3.5% of
lipid fraction, respectively [11]. They are composed of fatty acids. Although the
oxidative stability and the nutritional value of the oil are determined by the fatty
acid profile, the functionality of oil is affected by the type and amount of TAGs
[13]. The predominant structures in the amaranth oil are diunsaturated TAGs (UUS;
43.4–50.2%) and triunsaturated TAGs (UUU; 33–35.7%) [13].
The major TAG composition of Amaranthus cruentus is presented in Table .
POL, PLL, POO, OLL, and LOO are dominant TAGs in the amaranth oil with
carbon number ranging between 50 and 54 [7, 11, 13]. According to the TAG profile,
Reference no. [] Reference no. []Reference no. []
LLL 45.94 Not reported
OLL 12.1 10.97a2.4
PLL 13.8 14.48b16.7b
LOO 11.8 10.95c2.6
POL 20d16.69 2 5.4
PPL 7.5 7.01 22.6
OOO 7.9 4.82e3.6
POO 12.5f11.8g16.7
M, myristic acid; P, palmitic acid; Po, palmitoleic acid; S, stearic acid; O, oleic acid; L, linoleic acid;
Ln, linolenic acid.
aOLL+OOLn
bPLL+PLnO
cLOO+PoOO
dPOL+SLL
eOOO+MSO
fPOO+SOL
gPOO+PSL.
Table 1.
Major triacylglycerol composition of the oil from Amaranthus cruentus.


Amaranth Seed Oil Composition
DOI: http://dx.doi.org/10.5772/intechopen.91381
amaranth oil is similar to corn and cottonseed oils [7, 14]. Like other vegetable oils,
unsaturated fatty acids generally occupy the sn-2 position in the TAG structure of
the amaranth grain oil. Linoleic acid and oleic acid are the two predominant fatty
acids occupying the sn-2 position in the TAG structure of the amaranth grain oil,
with percentages of 61.3 and 35.5, respectively, resembling cereals and also cot-
tonseed and sesame seed oils [7]. Germination of the grain causes a decrease in TAG
content as a result of increasing the lipase activity. Heat treatment of the grain, such
as popping and cooking, decreases the TAG content [11].
. Fatty acid composition
The fatty acid composition of the oil gives information about oxidative stability
and nutritional quality. Table  presents the fatty acid profile of some species of
Amaranthus grain. Investigation on 104 genotypes from 30 species of Amaranthus
grain revealed that palmitic acid, oleic acid, and linoleic acid were predominant
in the oil with average percentages of 21.3, 28.2, and 46.5, respectively. Other fatty
acids such as stearic and linolenic are also present in the oil, but in minor amounts
[15]. The oil is highly unsaturated, containing more than 70% unsaturated fatty
acids. The ratio of saturated to unsaturated fatty acids ranges between 0.26 and
0.32 [16]. The fatty acid profile of the amaranth oil is similar to that of cottonseed,
buckwheat, and corn oils [13, 14].
. Squalene
Squalene is a triterpene (C30H50) with six double bonds at carbon numbers
2, 6, 10, 14, 18, and 22, which is present in the unsaponifiable fraction of the oil
(Figure ). It is an intermediate molecule for the biosynthesis of phytosterols and
cholesterol [22]. The main sources of squalene are whale and shark liver oil (40–
86%). However, due to the concerns about the extinction of these marine animals,
attempts are made to replace the animal source of squalene with a plant one [23].
Vegetable oils can be used as dietary sources of squalene. There is about 0.5%
squalene in olive oil; around 0.03% in corn, hazelnut, and peanut oils; and 0.01%
in grape seed and soybean oils [24]. The deodorizer distillates of oils such as olive
oil, soybean oil, and palm fatty acids have higher amounts of squalene, containing
10–30, 1.8–3.5, and 0.2–1.3%, respectively [25].
Amaranth grain is another natural plant source of squalene. Although amaranth
grain has lower oil content compared to the other oil-containing seeds, its oil
fraction is a rich source of squalene [26] (Table ). The high content of squalene in
C C: C: C: Source
A. cruentus 15.8–27 Tr-4.2 20.3–38.9 33.6–47 [7, 13, 15–19]
A. caudatus 12.3–20.5 2.2–4.7 23.8–32.9 35.6–49.8 [11, 18, 20]
A. hypochondriacus 17.9–24 0.9–3.7 16.3–33.7 38.9–52.5 [13, 15, 16, 18]
A. hybridus 18.6–22 1.3–4.4 18.7–26.3 47.4–55.9 [12, 15, 16, 18]
A. tricolor 19.5–24.3 1–3.6 25.9–27.5 46.4–51.5 [15, 16, 21]
A. dubius 15.7–25.9 0.7–4.1 14.8–30.5 46.9–53.5 [15, 18, 21]
Tr, trace.
Table 2.
Fatty acid composition of Amaranthus species grain oil.

Nutritional Value of Amaranth

the amaranth grain oil makes it a unique component, which can be used to recover
squalene. Although the direct derivation of squalene from amaranth seed is not
economically affordable, the recovery of squalene from amaranth oil as a coproduct
of starch production is advantageous [26]. An extensive study on 104 genotypes
from 30 species of Amaranthus grain revealed the squalene concentration in the oil
fraction was trace, 7.3% with an average of 4.2% [15]. The total content of squalene
is dependent on the method of oil extraction. It has been demonstrated that the
oil extracted with supercritical CO2 had the highest squalene concentration (about
7%), followed by oil extracted by chloroform: methanol (2: 1v/v; 6%) and cold-
pressed oil (5.7%) [27]. However, in another investigation, it has been shown that
squalene yield is the highest by accelerated solvent extraction method (4.4–4.7%),
followed by Soxhlet (3.8–4.2%) and supercritical fluid extraction (3.3–3.8%) meth-
ods, respectively [8]. It should be mentioned that heat treatments such as cooking
and popping the seeds cause an increase in the squalene concentration in the lipid
fraction [11].
Figure 1.
Structure of squalene.
Amaranthus species  Squalene Reference
A. cruentus 6.56 [7]
4.9 [11]
5.74–6.95 [27]
2.26–5.94 [17]
4.2–5.44 [16]
3.32–4.93 [15]
9.16 [13]
6.96 [14]
5.29–6.25 [28]
A. hypochondriacus 4.74–6.98 [15]
3.62–5.01 [16]
9.96 [13]
6.05–7.12 [28]
A. hybridus 5.23 [16]
2.26–7.3 [15]
A. caudatus 0.67–8.19 [20]
4.8 [11]
A. tricolor 4.73–5.75 [15]
6.14 [16]
A. dubius 2.72–5.63 [15]
Table 3.
Squalene content of different species of Amaranthus grain oil.


Amaranth Seed Oil Composition
DOI: http://dx.doi.org/10.5772/intechopen.91381
. Phytosterols
Plant sterols (phytosterols) are minor components of the vegetable oils, which
comprise a large proportion of unsaponifiable fraction. They contribute to oxidative
stability and extended shelf-life and have serum cholesterol-lowering properties
[29, 30]. Phytosterols are found as 4-desmethysterols, 4-monomethylsterols, and
4, 4′-dimethylsterols. They can also be classified as free and esterified forms [31].
It has been reported that a large proportion of the phytosterols in amaranth oil are
in esterified form and only low amounts are present in the free form (about 20%)
[7]. However, in most of the vegetable oils, such as soybean, sesame, olive, cotton-
seed, safflower, palm and coconut oils, free sterols comprise the predominant form
(54–85%) [32].
Total phytosterol content of the amaranth oil is between 1931 and 2762mg/100g
oil [7, 21, 27, 33]. This level of phytosterol in amaranth oil is much higher than
values established by Codex Alimentarius for most of common vegetable oils,
such as coconut oil (40–120mg/100g), cottonseed oil (270–640mg/100g),
flaxseed oil (230–690mg/100g), palm oil (30–70mg/100g), low-erucic acid
A. cruentus A.
dubius
A.
tricolor
III III IV VVI
Cholesterol Tr 0.01 0.01 — — — — —
24-Methylene
cholesterol
0.3 0.42 0.25 1.64 1.54 1.41 — —
Campesterol 1.6 0.76 11.83 1.96 1.96 2.61 1.57
Stigmasterol 0.9 0.77 0 .44 1.28 1.08 1.49 20.09 13.7
Δ7-Ergostenol —23.8 25.3 — — — — —
α-Spinasterol —34.2a26.3a44.94b53.24b56.31b— —
Sitostanol Tr 0.25 0.18 1.18 1.35 1.09 — —
Δ7-Campesterol 24.8 — — — — — 31.19 24.35
Clerosterol 42 — — — — — 1.58 3.71
Sitosterol 1.3 — — — — — 2 1.74
Δ5-Avenasterol 21.68 2.34 0.79 0.74 0.35 24.27 30.76
Δ5,24-Stigmastadienol Tr 1.89 2.26 1.92 2.04 1.45 13.66 10.73
Δ7-Stigmastenol 15.2 22.2 24.4 15.02 14.4 8 11.74 0.69 1.52
Δ7-Avenasterol 11.9 13.4 14.9 8.56 7.27 8.09 0.1 5 6.11
Δ7-Ergosterol — — — 17.29 16.32 16.12 — —
Cycloartenol 1.63 — — 2.26 0 0 — —
Citrostadienol 1.3 — — 3.3 0 0 — —
Total sterol
(mg/100g)
2460 2730 2590 2490 1931 2140 2488.7 2762
Reference [7] [33] [33] [27] [27] [27] [21] [21]
I, hexane extracted oil; II, crude oil extracted by hexane at –°C under atmospheric pressure; III, refined
amaranth oil; IV, oil extracted by supercritical CO under atm and °C; V, cold press oil; VI, solvent extracted
oil by chloroform: methanol (: v/v).
aα-Spinasterol + sitosterol + chondrillasterol.
bα-Spinasterol + sitosterol.
Table 4.
Phytosterol composition of different Amaranthus species.

Nutritional Value of Amaranth

rapeseed oil (450–1130mg/100g), safflower oil (210–460mg/100g), sesame
oil (450–1900mg/100g), soybean oil (180–450mg/100g), and sunflower oil
(240–500mg/100g) [34, 35]. However, wheat germ oil (4240mg/100g) and rice
bran oil (1050–3100mg/100g) have total phytosterol content higher than amaranth
oil [34, 36].
The phytosterol composition of the different Amaranthus species is presented
in Table . The predominant phytosterol in the Amaranthus cruentus seed oil is
the mixture of α-spinasterol and sitosterol [19, 21, 27]. Δ7-Sterols, that is, Δ7-
stigmastenol and Δ7-avenasterol and in some cases Δ7-ergosterol and Δ7-ergostenol,
are also present in considerable amounts in Amaranthus cruentus seed oil [7, 27, 33].
However, Δ7-campesterol and Δ5-avenasterol are the major phytosterols of
Amaranthus dubius and Amaranthus tricolor species. They also contain stigmasterol
and Δ5,24-stigmastadienol in considerable concentrations [21].
. Tocopherols and tocotrienols
Tocopherols and tocotrienols (i.e., tocols) are a part of unsaponifiable fraction,
which are forms of vitamin E and act as natural antioxidants in the vegetable oils.
Tocotrienols are structurally similar to the tocopherols, except that tocotrienols
have three double bonds within their phytol chains [37]. They have a chromanol
ring attached to a phytol chain. Each of tocopherols and tocotrienols is divided into
four subclasses, α-, β-, γ-, and δ- forms, which differ from each other as to the num-
ber of methyl groups on the chromanol ring [38]. The structure of eight homologs
of tocopherols and tocotrienols is presented in Figure .
Tocopherols comprise the majority of the tocols in most of the common oils.
However, tocotrienols are predominant in palm, rice bran, grape seed, and barely
oils [39, 40]. It has been reported that amaranth seed has small or negligible
amounts of tocotrienols [7, 18]. However, there are also reports that amaranth seed
oil has tocotrienol content higher than some vegetable oils, such as soybean oil,
peanut oil, and olive oil [21, 41].
γ-Tocopherol is the dominant tocol in most edible oils such as corn, soybean,
rapeseed, sesame seed, and flaxseed oils. While α-tocopherol is the most abundant
tocol in some vegetable oils such as safflower, sunflower, and olive oils [40]. Total
and individual content of tocol homologs depends on the amaranth species, variet-
ies, variation in analytical and extraction methods, and also growing location and
cultivation conditions [18, 42]. The total tocol content of 21 amaranth accessions
has been reported to be 31.5–78.3mg/kg seed (wet basis), with an average of
49.4mg/kg seed (wet basis) [18].
The study on the effect of dosages of fertilization with macronutrients on the
tocopherol profile of two varieties of Amaranthus cruentus seeds revealed that the
total tocopherol content was 48.6–79.9mg/kg (dry matter) [42]. Applying vari-
ous extraction methods, the determined contents of tocopherol homologs of the
commercial and wild Amaranthus caudatus seed were 12.5–47.84 (mg/kg seed)
α-tocopherol, 19.55–61.56 (mg/kg seed) β-tocopherol, 0.6–4.99 (mg/kg seed)
γ-tocopherol, and 2.1–48.79 (mg/kg seed) δ-tocopherol [20]. Depending on the
supercritical CO2 extraction parameters, the tocopherol homologs of amaranth seed
have s been reported as follows: 2.37–9.79 (mg/kg seed) α-tocopherol, 82.42–211.8
(mg/kg seed) β-tocopherol, 12.36–57.07 (mg/kg seed) γ-tocopherol, and 14.89–
38.59 (mg/kg seed) δ-tocopherol [43]. The tocopherol composition of n-hexane
extracted amaranth grain oil is presented in Table . It has been reported that the
total tocopherol content of n-hexane extracted amaranth oil is between 656.8 and
2588mg/kg oil [7, 21, 33].


Amaranth Seed Oil Composition
DOI: http://dx.doi.org/10.5772/intechopen.91381
. Carotenoids
Carotenoids are essential photosensitizers, which have an important role in plant
photosynthesis. They are also considered as provitamin A and possess antioxidative
properties [44]. The two carotenoids lutein (3.55–4.44mg/kg seeds) and zea-
xanthin (trace to 0.32mg/kg seeds) have been detected in amaranth seeds, lutein
being the predominant one. β-Carotene, the most known carotenoid, has not been
detected in amaranth seeds [45].
Figure 2.
Structure of different forms of tocopherols and tocotrienols.
α-T β-T γ-T δ-T Total tocopherols Source
A. tricolor 74.2 1 5 7. 9 1 7. 4 4 07. 2 656.8 [21]
A. dubius 135 245.7 22.3 376.4 7 79. 5 [21]
A. cruentus 248 546 — 8 802 [7]
A. cruentus (crude oil) 392 299 1187 710 2588 [33]
A. cruentus (refined oil) 232 225 728 603 1788 [33]
α-T, α-tocopherol; β-T, β-tocopherol; γ-T, γ-tocopherol; δ-T, δ-tocopherol.
Table 5.
Tocopherol concentration (mg/kg oil) of n-hexane extracted oils from different species of amaranth grain.

Nutritional Value of Amaranth

. Phospholipids
Phospholipids are essential polar lipid materials that have an important role in
biological membranes. TAGs are the major components of the nonpolar fraction
of the lipid. However, phospholipids are the main compounds of the polar fraction
of the lipids, which are considered as bound lipids. The phospholipid content of
the amaranth grain oil has been reported to be in the range of 9.1–10.2% of total
lipids [11].
. Oxidative stability
Concerning the high concentration of squalene and tocopherols, the amaranth
oil is expected to have good oxidative stability. Oxidative stability of amaranth oil
was determined by monitoring the peroxide value at 60°C for 30days. It has been
reported that amaranth oil had good oxidative stability, even better than the oxida-
tive stability of sunflower oil [11]. However, direct investigation of the stability of
crude amaranth oil obtained opposite results. It has been reported that although
amaranth oil contains high concentrations of squalene and tocopherols, which are
strong antioxidants, it did not have good oxidative stability [46].
. Conclusion
Amaranth grain contains 5–8% oil, which is mainly comprised of triacylglyc-
erols (78–82%). The oil also contains important minor phytochemicals, such as
squalene (up to 10%), phytosterols (2–3%), tocopherols, carotenoids, and phos-
pholipids (up to 10%). The high content of tocopherols and squalene, which act as
antioxidants, provides high oxidative stability for amaranth oil. The unique compo-
sition of amaranth seed oil makes it a useful ingredient in the food, pharmaceutical,
and cosmetic industries.
Conflict of interest
The authors declare no conflict of interest.


Amaranth Seed Oil Composition
DOI: http://dx.doi.org/10.5772/intechopen.91381
Author details
ParisaNasirpour-Tabrizi1, SodeifAzadmard-Damirchi1,2*, JavadHesari1
and ZahraPiravi-Vanak3
1 Department of Food Science and Technology, Faculty of Agriculture, University
of Tabriz, Tabriz, Iran
2 Food and Drug Safety Research Center, Health Management and Safety
Promotion Research Institute, Tabriz University of Medical Sciences, Tabriz, Iran
3 Food Technology and Agricultural Products Research Center, Standard Research
Institute (SRI), Karaj, Iran
*Address all correspondence to: sodeifazadmard@yahoo.com;
s-azadmard@tabrizu.ac.ir
© 2020 The Author(s). Licensee IntechOpen. This chapter is distributed under the terms
of the Creative Commons Attribution License (http://creativecommons.org/licenses/
by/3.0), which permits unrestricted use, distribution, and reproduction in any medium,
provided the original work is properly cited.

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