Research Signpost 37/661 (2), Fort P.O. Trivandrum-695 023 Kerala, India Plant Lipids Science, Technology, Nutritional Value and Benefits to Human Health, 2015: 119-145 ISBN: 978-81-308-0557-3 Editors: Grażyna Budryn and Dorota Żyżelewicz 2.6. Composition and functional properties of lipid components from selected cereal grains Justyna Rosicka-Kaczmarek, Karolina Miśkiewicz, Ewa Nebesny and Bartłomiej Makowski Institute of Chemical Food Technology, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, Stefanowskiego 4/10 St., 90-924 Lodz, Poland Abstract. Literature overview regarding the quantity and quality of various lipid fractions from cereal grains was conducted. Informations covered in this review will help to explain the functional properties of cereal lipids and their impact on technological processes during food production as well as will help to evaluate the influence of cereal lipids on the nutritional value of food products. Review regards mostly wheat grain, as it consists the main raw material in bakery. Furthermore oat and barley are covered, due to the fact that these are the cereals which are often used as a basic raw material in enriched bakery products as well as other food products with additional functional properties, resulting from rich composition of lipid fraction therein. Correspondence/Reprint request: Dr. Justyna Rosicka-Kaczmarek, Institute of Chemical Food Technology, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, Stefanowskiego 4/10 St., 90-924 Lodz, Poland. E-mail: [email protected]
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Research Signpost
37/661 (2), Fort P.O.
Trivandrum-695 023
Kerala, India
Plant Lipids Science, Technology, Nutritional Value and Benefits to Human Health, 2015: 119-145
ISBN: 978-81-308-0557-3 Editors: Grażyna Budryn and Dorota Żyżelewicz
2.6. Composition and functional properties
of lipid components from selected
cereal grains
Justyna Rosicka-Kaczmarek, Karolina Miśkiewicz, Ewa Nebesny and Bartłomiej Makowski
Institute of Chemical Food Technology, Faculty of Biotechnology and Food Sciences, Lodz University of Technology, Stefanowskiego 4/10 St., 90-924 Lodz, Poland
Abstract. Literature overview regarding the quantity and quality of various lipid fractions from cereal grains was conducted. Informations covered in this review will help to explain the functional properties of cereal lipids and their impact on technological processes during food production as well as will help to evaluate the influence of cereal lipids on the nutritional value of food products. Review regards mostly wheat grain, as it consists the main raw material in bakery. Furthermore oat and barley are covered, due to the fact that these are the cereals which are often used as a basic raw material in enriched bakery products as well as other food products with additional functional properties, resulting from rich composition of lipid fraction therein.
Correspondence/Reprint request: Dr. Justyna Rosicka-Kaczmarek, Institute of Chemical Food Technology,
Faculty of Biotechnology and Food Sciences, Lodz University of Technology, Stefanowskiego 4/10 St., 90-924
Composition and functional properties of lipid components from selected cereal grains 129
Table 3. Fatty acids composition of flour free lipids of Polish spring and winter
wheat varieties [33].
Variety Fatty acids content[%]
C16:0 C16:1 C18:0 C18:1 C18:2 C18:3 Others
Spring
varieties
Zebra 19.1 0.02 0.68 13.5 63.0 3.38 0.34
Jasna 18.9 0.02 0.57 14.1 62.2 3.72 0.48
Olimpia 19.8 0.04 0.64 13.7 62.8 2.81 0.27
Koksa 20.0 0.02 0.68 14.2 62.0 2.72 0.46
Opatka 19.6 0.01 0.67 15.1 62.8 1.80 0.04
Winter
varieties
Zyta 19.4 0.04 0.69 11.5 63.4 4.74 0.21
Korweta 19.6 0.05 0.54 11.2 63.3 4.97 0.38
Finezja 19.8 0.01 0.48 11.2 63.4 4.59 0.54
Tonacja 19.3 0.02 0.50 11.7 64.2 4.05 0.24
Mewa 19.4 0.01 0.49 11.8 63.5 4.28 0.50
Slawa 20.7 0.01 0.47 11.3 63.2 3.80 0.63
[35]. Free glycolipids occurred in the amount of 57-140 mg in 100 g of grain and 43-107 mg in 100 g of flour. Non-polar fractions dominated in the lipid composition and their ratio was 77-84% in grain and 68-77% in flour. A high content of non-polar lipids in kernels proves their full maturity, as immature cereal grain is characterized by the prevalence of structural lipids, mainly phospholipids, accompanied by a small amount of glycolipids [35]. The wheat cultivated in Australia, United Kingdom and Greece
contained a higher amount of glycolipids than varieties cultivated in the
United States. However it can be explained by the difficulty to compare
results obtained by different researchers due to different analytical methods,
for example different solvent usage (the use of chloroform allows to obtain
higher extraction yield of lipids than ether extraction) [36].
The FNL/FPoL ratio in the composition of free lipids of the investigated Polish wheat varieties varied between 3.22 and 5.14, while its variability in flours was lower and fluctuated from 1.75 to 3.32 [35]. Exemplary values of this index ranged from 6.3 to 11.3 for HRS wheat cultivated in the United States in the years 1971-1976 [36]. The content of free lipids in grain and flour from wheat grown in Poland is typical for that kind of cereal. In their composition occurs, however, relatively few favorable glycolipids, e.g. approximately 2-fold lower than in wheat cultivated in United States [35]. It was found that both the content of free glycolipids and total content of free polar fraction of grain may be predicted on the basis of the color measurement of kernels surface [35]. The content of bound lipid fraction was lower than that of free lipids: 3.0-4.5-fold in grain and 1.9-3.2-fold in flour, and was dominated by
Justyna Rosicka-Kaczmarek et al. 130
phospholipids (Table 4). Their content varied from 397 to 537 mg in 100 g of grain and from 307 to 490 mg in 100 g of flour [35]. In flours of 4 soft wheat varieties cultivated in Canada, the bound lipid content accounted for 531-753 mg/100 g, while in flours of 22 durum wheat varieties it ranged from 548 to 798 mg/100 g [37].
The influence of lipids on baking properties of wheat flour
Current knowledge of the role of lipids in wheat grain is ambiguous,
especially in the area of various lipid compounds interactions. Possible
knowledge of the quantity and composition of lipid fraction in wheat flour
may be considered as a great quality marker, which will help to select
optimal technological parameters with aim to receive the best product
quality.
The influence of individual lipid groups on baking quality of flour is
quite diverse. A positive effect of polar lipids and a negative effect of
non-polar lipids, especially free fatty acids, was proven [3]. Free
cis-unsaturated fatty acids (linoleic and oleic acids), which are the most abundant
lipid compounds in wheat lipid fraction, decrease the bakery properties of flour
Table 4. Free and bound lipids of Polish winter wheat grain and extraction flours
and sterols [54]. As literature data suggest the most abundant lipid fraction in
oat grain in triacylglycerols with a high content of unsaturated fatty acids.
Other present in oat lipid fractions are mono- and diacylglycerols, which are
present in smaller quantities, and which are formed as a result of
triacylglycerideshydrolysis by a lipase enzyme. Glycolipids and phospholipids
Table 5. Lipid content in dehulled oat grain and its individual constituents,
depending on solvent used [53].
Grain section
Lipid content [% d.b.]
High-lipid variety Low-lipid variety
Ether extracts Butanol-water
extracts
Ether
extracts
Butanol-water
extracts
Dehulled grain 8.0 1.6 5.5 1.4
Hull 2.3 0.6 2.0 0.6
Bran 9.5 1.2 6.4 1.3
Starchy endosperm 6.8 1.0 5.2 1.0
Scutellum 20.6 2.8 20.4 4.2
Germ 12.6 3.3 10.6 4.1 Specific composition of lipid fractions
Table 6. Percentage of various fractions of lipids in whole grain of dehulled oat and
its individual sections [56].
Lipid fraction
Lipid fraction content [%]*
Dehulled
grain
Individual grain sections
Bran Endosperm Scutellum Germ
Triacyloglycerols 41 39 41 50 58
1,3-diacyloglycerols 2 2 2 1 2
1,2-diacyloglycerols 1 1 1 2 2
Freefattyacids 5 3 3 2 2
Sterols 1 1 1 1 1
Sterol glycosides 1 1 1 1 1
Monogalactosyldiacylglycerols 4 4 5 - -
Digalactosyldiacylglycerols 7 9 8 - -
Phosphatidylethanolamine 2 3 2 1 1
Lysophosphatidylethanolamine 1 2 2 - -
Phosphatidylcholine 5 4 4 3 3
Lysophosphatidylcholine 2 3 3 - -
Otherfractions (calculated) 28 28 27 39 30 *Percentage in relation to overall lipid content
Justyna Rosicka-Kaczmarek et al. 134
consist 6.9-7.6% and 3.2-6.1% of an overall content of lipids in dehulled oat,
respectively. In glycolipid group of compounds mainly mono- and
digalactosyldiacylglycerols are present (they consist over 60% of overall
glycolipids). Among phospholipid phosphatidylcholine is the most abundant
(29.9%). According to De la Roche et al. [55] high-lipid oat varieties are
characterized by higher content of triacylglycerols (ca. 80%) and lower
phospholipid content (ca. 6%), compared to low-lipid varieties.
Fatty acids compositions
Oat lipids contain fatty acids with a chemical compositions beneficial from both technological and nutritional point of view [57]. Oat fat is rich in unsaturated fatty acids, which constitute 80% of all acids present in oat [58]. Essential unsaturated fatty acids consist around 40% of all raw fat, which in oat flakes stands for 2.5-3.0% of its overall weight. Consumption of 100 g of oat flakes covers ca. 30% of daily recommended intake of linoleic acid [15]. Essential fatty acids are required for proper development of young organisms and maintaining good state of health. Beside structural function of essential unsaturated fatty acids they also play an important role in many biochemical transformations as well they regulate physiological functions of human organisms (i.e. through prostaglandins and other biologically active compounds synthesis) [59]. According to research of many authors [60,61,62], in oat lipids most abundant fatty acids are: myristic (0.1-4.9%), palmitic (13-26%), stearic (1-3%), oleic (22-47%), linoleic (25-52%) and linolenic acid (1-3%), and they consist over 95% of all fatty acids present in oat lipids. Few studies indicate that also other fatty acids can be found in oat lipids: lauric, palmitoleic, arachidic (<0.1%) [63] and nervonic acid [64]. In cereal grain lipids, fatty acids are present mostly in ester form, in such fractions as: triacylglycerols, phospholipids and sterols. In table 7 fatty acid composition in polar and non-polar lipid fractions
from dehulled oat are placed. Showed data indicate to significant variations
of palmitic (16:0) and oleic acid (18:1ω9) in three lipid fractions such as
triacylglycerols, phospholipids and glycolipids. Triacylglycerol fraction is
characterized by smaller palmitic acid quantity, comparing to polar lipid
fractions. In polar lipid fractions (both glycolipids and phospholipids),
palmitic acid percentage in higher and oleic acid lower than in non-polar
lipid fraction. As literature data state [55, 66] an increase of lipid content in
oat grain cause a decrease of palmitic acid quantity with a simultaneous
increase of oleic acid concentration.
In table 8 the concentrations of fatty acids in lipids deriving from
dehulled oat grain and its individual sections are presented [53]. According to
Composition and functional properties of lipid components from selected cereal grains 135
Table 7. Fatty acid composition in main fractions of lipids from dehulled oat [65].
Lipid fraction
Fatty acids [%]
Myristic
acid
(14:0)
Palmitic
acid
(16:0)
Stearic
acid
(18:0)
Oleic
acid
(18:1ω9)
Linoleic
acid
(18:2ω6)
Linolenic
acid
(18:3ω3)
Triacylglycerols 1.5 14.8 2.2 43.3 35.0 2.0
Glycolipids 4.3 22.1 4.4 25.1 36.2 4.0
Phospholipids 2.2 28.1 4.2 21.3 38.1 2.8
Table 8. Fatty acid composition in lipids from dehulled oat grain and its individual
sections [53].
Fatty acids [%]
Myristic
acid
(14:0)
Palmitic
acid
(16:0)
Stearic
acid
(18:0)
Oleic
acid
(18:1ω9)
Linoleic
acid
(18:2ω6)
Linolenic
acid
(18:3ω3)
Ether extracts
Dehulled oat grain 0.4 18.8 2.2 39.4 37.9 1.3
Bran 0.4 18.1 1.9 38.4 39.6 1.6
Starchy endosperm 0.6 18.9 2.3 37.4 39.4 1.4
Scutellum 0.6 21.1 1.2 34.5 39.7 2.8
Germ 0.9 21.6 1.9 28.8 42.5 4.1
Butanol-water extracts
Dehulled oat grain 0.9 25.7 2.0 28.8 41.0 1.4
Bran 1.6 25.7 1.6 27.2 42.2 1.4
Starchy endosperm 0.6 27.3 2.4 28.4 39.7 1.3
data collected in table 8 it can be observed that arrangement of fatty acids in
dehulled oat grain and its individual sections depends on the solvent used for
lipid extraction. In case of lipids extracted with the use of diethyl ether
(ether extracts) the composition and concentrations of fatty acids both in
bran and endosperm are similar to these of dehulled oat grain. In lipids
extracted with the use of butanol-water solvent only myristic acid is
unevenly distributed among starchy endosperm (0.6%) and bran (1.6%).
Presented data indicate also that the percentage of other fatty acids in bran
and starchy endosperm is comparable with dehulled oat grain.
Oat starch lipids
Oat starch possesses unique physical, chemical and structural properties,
which is why it is noticeably different from other starch varieties. They vary in
granule size, lipid content, rheological properties, small retrogradation tendency
Justyna Rosicka-Kaczmarek et al. 136
and are unique due to the occurrence of “intermediate fraction”, which is a starch
type with properties combining both amylose and amylopectin [67]. Lipids in oat
starch, depending of oat variety, are present in amounts from 1.1 to 2.5%, which
an average value of 1.3% [68]. These compounds are accumulated during the
synthesis of starch granule and they form complexes with amylose by
penetration of the hydrophobic insides of amylose helix [69, 70]. The presence
of lipids significantly decreases the swelling ability and water solubility of starch
as well as delays and inhibits the gelatinization process. They also determine gel
viscosity and inhibit gel formation [71].
Results of research done by Hartunian, Sowa and White [70] point to
significant differences in lipid content in starches from high- and low-lipid
oat varieties. High-lipid oat varieties are characterized by higher lipid
content, on average on a level of 2.5%, than low-lipid oat varieties – lipid
content amounting 2.1%. In oat starch lipids both polar and non-polar lipids
can be found, however non-polar lipids consist a much smaller group.
Literature data [72] show that oat starch lipids contain
lysophosphatidylcholine (51.6%), lysophosphatidylethanolamine (5.1%) and
free fatty acids (7.7%). It can be observed that lysophosphatidylcholine is the
most abundant fraction of lipids in oat starch. Oat starch lipid fraction is also
characterized by the presence of high amounts of palmitic (46.2%) and
linoleic acids (42.1%). Different fatty acids are present on smaller quantities
Oat grain lipids are often accompanied by substances which are immune
to alkaline saponification. They are named as “unsaponifiable fraction of
lipids”. Following compounds belong to this fraction: sterols, tocopherols,
carotenoids. The main compound of unsaponifiable fraction of lipids in oat are
sterols. In whole oat grain the most abundant sterol is β-sitosterol, which
constitute about 69% of all sterols. Additionally, beside β-sitosterol, in oat
grain the following sterol compounds can be found: 5-avenasterol and 7-
avenasterol, which constitute 21% and 13.5%, respectively [73]. Oat grain as
well oil extracted from this grain is characterized also by the presence of
tocopherols (α- and β-tocopherol) and tocotrienols (α-tocotrienol) [74, 75]. In
oat lipids, compounds with strong antioxidant properties were found. They
include polyphenols, among which hydroxybenzoic and hydroxycinnamic
acids can be distinguished. Activity of these compounds is similar to this of
synthetic antioxidants, i.e. butylhydroxytoluene or propyl gallat [76]. They
have the ability to reduce peroxides and hydroxides as well as inactivate free
radicals, breaking propagation phase in a chain reaction. Oat lipid antioxidant
compounds possess also bacteriostatic and pharmacological activity,
improving heart health, having a positive effect on circulatory system,
preventing chronic inflammations [60] and neoplastic diseases [77]. The
Composition and functional properties of lipid components from selected cereal grains 137
negative effect of their presence is a decrease of protein assimilation [78].
Compounds with antioxidant properties in oat grain, beside Vitamin E, include
also polyphenol compounds: phenolic acids, their esters and amides,
alkylphenols, flavonoids and avenanthramides [79]. Avenanthramides due to
their thermostability are not affected by technological processes.
Lipid barley grains
Barley grains contain lipids such as: phospholipids, glycolipids, fatty acids, acylglycerols and smaller amounts of sterols, terpenes and carotenoids. In barley grain lipid compounds can be found mostly in germ and aleurone layer [80, 81]. During the formation of barley grain endosperm, mostly structural lipids can be observed - phospholipids with smaller quantities of glycolipids. Non-polar lipid fraction during this stage of grain development contains mostly free fatty acids and small quantities of mono-, di- and triacylglycerols. During grain maturation the concentration of triacylglycerols increases and amounts of mono- and diacylglycerols as well as free fatty acids decreases. In fully mature grain triacylglycerols consist 54% of overall lipid content [82]. As literature data state [83, 84] the quantity of polar lipids (structural lipids), non-polar lipids (storage lipids) and starch lipids in barley grain increases from 24
th day after pollination. After 42 days after pollination and
during further maturation a decrease of lipid fraction content takes place.
Content and distribution of lipids
Lipid content in barley grain is very diverse and varies from 1.9% to 4.6%. According to data presented by Newman and Newman [85] barley
varieties with lipid content of even 7% can be found. For two-row and six-row barley lipid content varies between 2.1-3.7% and 1.9-4.6%, respectively [86, 87]. In hulled and naked barley varieties lipid content is also diverse and ranges between 2.1-3.1% and 2.1-3.7%, respectively. Furthermore barley varieties with high amylose content is characterized by higher lipid content than varieties with high amylopectin content, as well as varieties with similar
levels of those two starch fractions. Although lipid concentrations in different barley varieties in often quite diverse its distribution in individual sections of grain is relatively even [88, 89]. According to information presented in table 9 it can be observed that the biggest lipid concentration is in the germ of barley grain (19.6%). In hull, endosperm and bran lipid content does not exceed 3%. Bran and endosperm constitute 87% of grain weight so they can be recognized as the main lipid source in the grain.
Justyna Rosicka-Kaczmarek et al. 138
Table 9. Lipid content in barley grain and its individual constituents [90].
Barley grain/individual
constituents Lipid content [%]
Grain 3.2
Hull 2.4
Bran and endosperm 2.8
Germ 19.6
Specific composition of lipid fractions
Among barley lipids non-polar lipid fraction constitutes on average 67-78% of all lipids, glycolipids consist 8-13% and phospholipids – 14-21% [91]. Non-polar lipids are the main lipid fraction in barley, so an increase of overall lipid content can be associated with an increase of this fraction [92]. From non-polar lipids triacylglycerols are the main fraction (62%). It consists mainly from unsaturated fatty acids. Mono- and diacylglycerols (ca. 7%), sterol glycosides (ca. 4%), sterols (3%) and free fatty acids can also be found in barley grain [93]. In polar lipid fraction glycolipids and phospholipids can distinguished. Glycolipids consist from monogalactosyldiacylglycerols (27-34%) and digalactosyldiacylglycerols (22-39%) and phospholipids fraction is mostly build from phosphatidylcholine (52%), phosphatidylethanolamine (10%) and phosphatidylinositol (3%) [93]. Literature data [94] indicate that non-polar lipid fraction is present in bigger quantities in all grain section that polar lipids. Furthermore non-polar lipids quantity is similar in all grain sections. Glycolipid and phospholipid concentrations in individual sections of barley grain is quite diverse. Glycolipid content in the germ is usually on a level of 6%, but in endosperm, hull and bran its concentration rises 2-3-fold. Phospholipids are most abundant in the bran (23.1%), and are present in smaller amounts in germ, endosperm and hull, which amount to 17.8% and 5.9%, respectively.
Fatty acids compositions
Barley lipids are a great source of fatty acids, which are valuable from a
nutritional point of view [85, 82]. Among saturated fatty acids the most
abundant one is the palmitic acid (16:0), which can be found in barley in
amounts ranging from 17 to 28%. Other saturated fatty acids are: stearic
(18:0) (0.6-2.0%), and myristic acids(14:0) (below 1%). Unsaturated fatty
acids of barley consist of 52-59% linoleic (18:2, n-6), 10-23% oleic (18:1, n-
9) and 4-8% linolenic acids (18:3, n-3).
Composition and functional properties of lipid components from selected cereal grains 139
Table 10. Fatty acids profile in main fractions of barley lipids [95].
In table 10 it can be observed that among both polar and non-polar lipids
palmitic and linoleic acids are the most abundant. These acids are present
mostly in polar lipid fraction.
Barley starch lipids
Barley starch contain around 1% of lipids. Barley starch lipids contain both polar and non-polar lipids, however polar lipids are present in much bigger concentrations. As literature data indicate [96] barley starch lipids are a rich source of lysophosphatidylcholine (62.5%). This fraction of barley starch lipids is rich in palmitic (44.3%) and linoleic acids (45.6%). Other fatty acids, such as: myristic, oleic and linolenic are present in aforementioned fraction in concentrations of 0.5%, 3.8% and 4.1%, respectively [97]. Lipid content in oat is 3-5-fold higher than in other cereals. Cereal lipids consist of mono- and polyene fatty acids. Polyene acids, which have the properties of essential unsaturated fatty acids, have to be provided in diet due to the fact that they are vital for proper organism development and functioning. Essential fatty acids possess the role of prostaglandin precursors, which are also called “tissue hormones”. They have numerous functions in human organisms, e.g.: regulation of circulatory system functions, secretion of digestive juices and platelet aggregation. Lipids are also carriers of biologically active compounds, such as vitamins A, D, E and K. In described cereal lipids,palmitic, oleic and linoleic acids are present in the biggest quantities (40-50%). Due to the good quality and quantity of lipid fraction in cereals, they as well as their products can be successfully used for functional food production [98].
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