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1) INTRODUCTION:
Oil seed crops are important sources of energy for human consumption and also
provide raw material for a wide range of industrial products. Earlier animal products
such as lard, beef tallow, butter characterized by saturated fats were major sources of
fat supply. Since a number of nutritional and medical studies indicated strong
relationship between high levels of saturated fats and cholesterol, and incidence of
Coronary Heart Disease (CHD), there was a major shift in consumption from animal
fats to vegetable oils. The Institute of Shortenings and Edible Oils (ISEO) has reported
that there was a shift from two-thirds of the visible fat as animal fat to one-third in 1966
and to 95% of the visible fat as vegetable origin in 1992.
Since vegetable oils are predominantly composed of unsaturated fatty acids they
lack the characteristic stability, texture and flavour, imparted by saturated fats. So to
provide the same texture, flavour and stability, oils were partially hydrogenated, which
created a new issue: trans fatty acids. Elevated levels of trans fatty acids led to risk of
CHD. So genetic modification of oil seed crops through breeding and genetic
engineering, to produce oils with increased stability and flavour, without affecting their
characteristic nutritional value is considered as the best alternative.
The vegetable oils most commonly used in the trend towards “healthy” are
soybean, canola, sunflower, cottonseed, safflower, olive and peanut. About 54% of the
world oilseed production is soybean, 12% cotton seed, 11% rapeseed, 10% peanut, 9%
sunflower and 4% others. All these crops except rapeseed falls into oleic-linoleic group
(Swern, 1964). However in the development of canola from rapeseed , the erucic acid
was replaced by oleic placing canola within the oleic-linoleic group (Ronald, 1996).
Oleic and linoleic acids accounts for 70% of the world fatty acid supply (Khanna and
Singh, 1991) and known to lower blood cholesterol level preventing heart attacks, but
in terms of stability former dominates latter. Medium Chain (saturated) Fatty Acids
synthesized by wild genus Cuphea, that provides quick energy without raising
cholesterol level and α- linolenic acid produced by linseed, that imparts immunity in
human beings, are gaining importance in recent years. Also available are synthetically
structured fats, which contributes fewer calories and less fat.
The fats and oils industry has reacted to a rapidly changing nutritional
awareness of the effect of fats in the diet. Now consumers have moved from buying oils
“off the rack” to an industry which now offers “tailored oils” which have been coined
the term “designer fats and oils”.
The chapter covers in brief the chemistry, uses and biosynthesis of fats to
provide an understanding on the need for designing oil and basic principles involved in
it. Also various approaches for designing oil have been discussed with detailed
elaboration of crop wise breeding and genetic engineering approaches.
One system of naming USFA is to indicate the position of first double bond
counting from the methyl end. The terminal carbon atom is called omega carbon
atom. Fatty acids having their first double bond after carbon 3 (counting from and
including omega carbon) are called Omega 3 Fatty Acids (α-linolenic acid). Likewise
fatty acids with first double bond at sixth carbon atom are called Omega 6 Fatty
Acids (linoleic acid). These omega fatty acids (Fig: 1) are popularly called as
“immunonutrients”.
5) Designing Oil:
Oils or fats can be designed by the following three methods:
1) Chemical and physical processes.
2) Breeding and genetic engineering.
3) Synthetically structured fats.
5.1) Chemical and Physical Processes (Hegenbart, 1991):
5.1.1) Blending of Oils:
Different oil types can be blended to achieve functional changes but the possible
modification is limited and using a single type of oil may be desirable in certain
products.
5.1.2) Hydrogenation:
This method is used to convert liquid oils to solid fats, which are used in
shortenings and margarines. It is a chemical process of adding hydrogen atoms to fatty
acid chains by reacting oil with hydrogen in the presence of a catalyst (nickel). This
results in saturation and conversion of double bonds from cis to trans configuration
(trans fatty acid). Both these effects straighten out the molecules so they can lie closer
together and become solid rather than liquid.
5.1.3) Fractionation:
This is the process by which oil may be separated into its different TG portions
based on their individual melting points. The oil is held at a predetermined temperature
and the solids present are filtered out or are separated in some way. The synthetic
MCTs are manufactured from caprylic and capric acids obtained by fractionating
coconut and palm-kernel oils.
5.1.4) Rearranging:
This process modifies oil properties by exchanging fatty acids on TG molecules.
The procedure is called interesterification if the fatty acids simply switch positions on
the molecule and transterification if the fatty acids actually change TGs. This is often
done in fats designed for confections or margarines. Interesterification also can be
directed in such a way as to produce a solid fat from oil without hydrogenation.
5.2) Breeding and genetic engineering:
The usage of oil depends on its fatty acid profile. The fatty acid profile in turn depends
upon the activity of fatty acid biosynthetic enzymes, which is ultimately decided by the
genes encoding these enzymes. So breeding for an desirable oil composition involves
concentration of these genes to enhance the level of require fatty acid in the cultivar.
Conventional breeding approaches utilize either the natural genetic variation or
generated variation (mutation) to develop cultivars possessing novel traits through
selection or hybridization. Molecular breeding approaches hasten the process of
conventional breeding and reduce the time needed to develop new varieties. Through
molecular breeding approaches, creation of novel genetic variation (somaclonal
variation), breaking sexual crossability barriers (embryo rescue, protoplast fusion),
rapid generation of homozygous lines (doubled haploids) and precise selection for
desirable traits (molecular markers) can be achieved. Thus classical and molecular
breeding approaches in combination offers a wide spectrum of methods for efficiently
designing oil with desired fatty acid composition. However further adjustments will not
be realized satisfactorily without the assistance of genetic engineering (Friedt and
Wilfried). Combination of these methods have led to drastic modification of fatty acid
profile of various oilseed crops (Table: 2) which has been discussed crop wise.
Acyl-CoA synthetase
Oleoyl-CoA
KAS and LPAAT are the key enzymes in erucic acid synthesis of which the
former is characterized well. Earlier to brassica the gene (FAE 1) encoding KAS has
been isolated in Arabdiopsis. From B. napus Barret et al (1998) isolated two sequences,
CE7 and CE8 homologus to Arabdiopsis FAE 1 gene and found tight linkage of one of
the FAE 1 genes to E1 locus. Fourmann et al. (1998) designed PCR primers
corresponding to FAE 1 gene and amplified two B. napus genes Bn-FAE 1 and Bn-
FAE 2 corresponding to its parental species B. rapa (B. campestris) and B. oleraceae
respectively. Also they reported co-segregation of these genes with E1 and E2 loci
respectively. These genes had 98%, 86%, 84% and 58% nucleotide similarity with FAE
1 genes from B. napus, B. juncea, Arabdiopsis thaliana and Simmondsia chinensis
respectively. The FAE 1 genes from low and high erucic acid lines differ at 13
positions at amino acid sequence level, mainly localized in the central part of protein
sequence (Das et al. 2002). This altered amino acid sequence in variant β-Ketoacyl-
ACP Synthase proteins due to mutated FAE 1 gene leading to lack of acyl-CoA
elongation activity is responsible for low level of erucic acid in brassica seed oil.
Since erucic acid alleles are additive in nature, theoretical expectation of erucic
acid yield through conventional breeding is only 66-67%. This is because erucic acid
occupies only sn-1 and sn-3 positions of the glycerol molecule (Appelqvist, 1971).
However through genetic engineering it might be possible to increase the levels of
erucic acid up to 80% by incorporating erucic acid in the sn-2 position also (Katavic et
al. 2000). Lassner et al. (1995) through transgenic experiments demonstrated that erucic
acid could be positioned in sn-2 indicating the feasibility of altering stereochemical
composition of brassica seed oils. Expression of Arabdiopsis FAE-1 gene and yeast
SLC-1 gene in high erucic acid cultivar Hero resulted in increased proportion of erucic
acid in transgenic Hero lines (Katavic et al. 2001; Taylor et al. 2002).
High oleic canola (> 86%) has been produced using seed specific inhibition of
microsomal oleate desaturase and microsomal linoleate desaturase gene expression,
either through co-suppression or antisense technology. Co-suppression has been used in
combination with mutation treatments to produce modified fatty acid profiles (Debonte
and Hitz, 1996). Cargill’s Clear Valley 75 is a high oleic (75%) cultivar (Scarth and
McVetty). High laurate canola is the world’s first transgenic oilseed crop in commercial
production. The high laurate trait was the result of insertion of the acyl-ACP TE,
isolated from Umbellularia california (Californian bay).
5.2.2) Soybean:
Soybean (Glycine max) tops among all oilseed crops with 54% of world oilseed
production. Besides oil, soybean seeds contain high amount of protein (42-45%). Seed
oil of soybean consists largely of unsaturated fatty acids predominating in linoleic acid
(50-51%) followed by oleic (28-29%) and linolenic acids (6-7%). It also has significant
amount of palmitic acid (9-10%). The high content of linoleic acid makes soya oil
suitable for edible purposes. However, the oil gets oxidized readily leading to off type
flavour and poor keeping quality due to high amount of linolenic acid. So oil from
soybean cultivars with <1% linolenic acid, which will have improved oxidative
stability, reducing the formation of undesirable flavour compounds is considered
desirable. Soybean oil with elevated palmitate content may be useful for producing
solid fat (for baked products) at room temperature without hydrogenation. Also oils rich
in oleic acid that have improved flavour and nutritional value is preferred. So designing
of soya oil is primarily targeted towards low linolenic followed by high oleic and
palmitic types.
Genetics of three major fatty acids of soybean oil viz., palmitic, oleic and
linolenic have been studied well. The inheritance of oil content is influenced by
maternal effects (Brim et al. 1968) and governed by additive genes (Mc Kendry et al.
1985). Correlation among individual fatty acids and fatty acids with oil content, protein
content and seed size have been reported by several authors (Zhang, 1991; Liu et al.
1995; Nian et al. 1996; Maestri et al. 1998; Stolzfus et al. 2000; Kwon and Shin, 2002).
Oil and protein content are negatively correlated traits, however oleic acid is positively
correlated with crude protein content. Linoleic and linolenic acids are positively
correlated with each other and negatively associated with oleic acid. The association of
palmitic acid is positive with linoleic and linolenic acids and negative with oleic acid.
Seed size is positively correlated with oleic and stearic acids and negatively correlated
with linoleic and linolenic acids. So in breeding programmes selection for larger seeds
will increase oleic and decrease linolenic acid content in seed oil.
M11 and M23 (Rahman et al. 1994) are high oleic acid mutants of soybean
derived from cultivar Bay via treatement with X-rays. Oleic acid alleles of Bay, M11
and M23 are designated as Ol, ola, and ol respectively (Takagi and Rahman, 1996;
Rahman et al. 1996). The genotypes of Bay, M11 and M23 are OlOl, olaola, olol
respectively with average oleic acid content 27.8%, 30.8% and 48.6% of the total fatty
acids respectively. Ol allele for low oleic acid in Bay is partially dominant to the allele
ol in M23 and completely dominant to the allele ola in M11. Maternal effects influence
oleic acid inheritance and there is complete inverse relationship between oleic and
linoleic acid contents in both the mutants which indicates that the mutant alleles ol and
ola may also control the linoleic acid content by blocking the synthesis of this acid at the
step of oleic acid desaturation. The linolenic acid locus designated as fan, and fanxa
locus is responsible for low linolenic acid content (Rahman et al. 2001). Ol and fanxa
are independently inherited and combination of these two loci resulted in a germplasm
line DHL with high oleic and low linolenic acid content.
Two cDNA sequences FAD 2-1 and FAD 2-2 encoding microsomal -6 fatty
acid desaturase have been isolated and characterized in soybean (Heppard et al. 1996).
The FAD 2-1 gene is strongly expressed in developing seeds whereas the FAD 2-2
gene is constitutively expressed and the former plays major role in controlling
conversion of oleic to linoleic acid in storage lipids during seed development. So down
regulation of FAD 2-1 will elevate oleic acid content in seed oil. RFLP analysis of
Bay, M11 and M23 using microsomal -6 fatty acid desaturase cDNAs as probe
resulted in identification of a band (4.6 kb) present in Bay and M11, and absent in M23
(Kinoshita et al. 1998). The band fitted with the expected F2 ratio 1:2:1 and their
intensities were completely consistent with oleic acid content indicating that high oleic
acid in M23 is due to some nucleotide modification of the ol locus encoding for an
isoenzyme of microsomal -6 fatty acid desaturase.
Through mutation breeding low linolenate lines (A5, A6), low palmitate line
(A18), high palmitate line (A19) and high oleate lines (M11 and M23) are developed.
Soybean cultivars with high oleic acid (Bay) and low linoleic acid (Murayutaka) have
been bred. Also genetically engineered high oleic acid soybean cultivars are available.
High oleic soybean oil showed greater oxidative stability than other high oleic oils,
including sunflower, canola and corn (Ronald, 1996).
5.2.3) Sunflower:
Sunflower oil is valued as premium oil in world market because of its high
content of linoleic acid (67%) associated with low linolenic acid content (0.5%).
However sunflower oil with high oleic acid is preferred due to its oxidative stability.
The development of sunflower with high oleic acid content was reported by
Soladatov (1976). A single, partially domonint gene designated as Ol, controls the high
oleic acid trait in sunflower. Miller et al. (1987) confirmed this, who further reported a
second gene, ml. The presence of recessive gene ml in homozygous condition along
with gene Ol, results in high oleic acid content. Pervenets is a high oleic acid cultivar
developed through mutation breeding (Miller and Vick, 1984).
The relative proportions of oleic and linoleic acids in sunflower oil are under
both genetic and environmental control. Several investigators have reported that there is
inverse correlation between prevailing temperature during growth period and linoleic
acid content; and the opposite is true for oleic acid (Kinman and Earle, 1964; Canvin,
1965; Kawanabe, 1979; Downes and Tonnet, 1982). A variety under constant 10◦C
produced about 80% linoleic acid while at 26.5◦C the linoleic acid content was dropped
to nearly 25%, and this was accompanied by simultaneous rise in oleic acid content
(Canvin, 1965). Temperature stable high oleic acid strain (86%) was developed by
treatment of cultivar Peredovik with chemical mutagens (Prudy, 1985; 1986).
However the sunflower industry had difficulty in maintaining very high oleic
acid level and elected to commercialize, a mid oleic acid (60%) oil composition
(Downey). ARS, USA in co-operation with private industries have released new class
of sunflower called “NuSun” having mid oleic composition (Johnson, 1998).
5.2.4) Linseed:
Linseed or Flax (Linum usitatissimum) has traditionally been utilized as a source
of industrial oil, for use in the production of paints, varnishes, inks and linoleum. The
high level of linolenic acid in the oil (45-65%) imparts rapid drying property in such
products. Since the demand for industrial quality linseed oil is declining due to
synthetic substitutes and markets for vegetable oil is expanding, efforts are on to
develop edible quality linseed oil. The presence of high linolenic acid in linseed oil
causes rancidity and renders it unsuitable for edible purpose. So to convert linseed in to
premium edible oil linolenic acid would have to be reduced considerably to a maximum
of 3%.
In contrary high linolenic acid in linseed has valued it as a nutritionally
desirable crop. Linseed is the richest plant source of (alpha) linolenic acid, an omega 3
fatty acid and also contains average content (18-20%) of linoleic acid (omega 6 fatty
acid). Encapsulated linseed oil is available commercially. Edible linseed oil with
desirable nutritional and keeping quality can be obtained by developing cultivars with
fatty acid profile fitting the recommended linoleic: α-linolenic acid ratio (5:1 to 10:1)
balanced with oxidative resistant oleic acid.
Extensive surveys of Linum usitatissimum germplasm collection revealed that
variety mean for linolenic acid content varied only between 45% to 65% (Zimmerman
and Klosterman, 1959; Green and Marshal, 1981) indicating mutation breeding to be a
promising approach rather than hybridization and selection to reduce linolenic acid
content (Green and Marshal, 1984). Two mutant lines M 1589 and M 1722 were
developed following EMS mutagenesis of cultivar Glenelg. The linolenic acid content
of these mutant lines constituted approximately 29% compared with 43% in Glenelg
(Green and Marshal, 1984). Further crossing these two mutant lines led to development
of a mutant genotype having less than 2% linolenic acid (Green, 1986a). The virtual
elimination of linolenic acid (<2%) from the seed lipids is accompanied by an
equivalent increase in the content of linoleic acid (>46%), the proportions of other fatty
acids remaining unchanged. These changes indicated that the mutation block the final
desaturation of linoleic to linolenic acid (Green and Marshal, 1984; Green, 1986a).
Studies on linolenic acid inheritance in mutant lines M 1589 and M1722
revealed that both lines are homozygous for a single gene mutation that reduce linolenic
acid content and these mutations are in different unlinked genes, exhibiting additive
(co-dominant) gene action (Green, 1986b). The mutant locus in M 1589 and M 1722
are designated as Ln1 and Ln2 respectively. Varieties producing edible linseed oil
called “Linola” (Dribnenki and Green, 1995; Dribnenki et al. 1996; Dribnenki et al.
1999) are now commercially grown and consumed in Canada, United States, Australia
and several European countries (Table: 3).
5.2.6) Sesame:
The seed oil of sesame (Sesamum indicum) contains mainly four fatty acids viz.,
palmitic, stearic, oleic and linoleic acids. Sesame oil is unique in containing several
lignan antioxidants as well as some tocopherols. The lignans, sesamin and sesamolin
and their derivatives, sesamol and sesaminol, and their related compounds prevent the
oxidation of sesame oil contributing to the characteristic stability and extended shelf
life.
Oleic and linoleic acids constitute around 85% of oil composition and their
inheritance is controlled by single gene (Brar and Ahuja, 1979). The high oleic acid
allele (Ol) is dominant over low oleic acid allele (ol). Variation for fatty acid content
was induced by gamma rays (Lee et al., 1985) and by sodium azide (Kang, 1994).
These efforts resulted in release of Seodun in 1997 in South Korea, which has high
oleic acid content.
5.2.7) Groundnut:
Groundnut (Arachis hypogea) oil is composed of 80% unsaturated fatty acids
and unique in containing LCFAs, arachidic and behenic acids. These LCFAs are useful
in emulsification and stabilization of products like peanut butter, but their implications
in heart disease is a matter of concern (Kritchevsky et al. 1971). So far not much efforts
for fatty acid modification has been done in this crop.
The Virginia botanical types generally have higher oleic acid content and lower
linoleic acid content than Spanish or Valencia types. Crosses among these types
indicated that sufficient variability for fatty acid could be generated by recombination
of genes. A favourable feature for breeding is that fatty acid composition is determined
by growing embryo and few additive genes are involved in determination of oleic and
linoleic acid ratio (Khan et al. 1974).
5.2.8) Cuphea:
The genus Cuphea belongs to family Lythraceae (Graham, 1988; Singh, 2001)
and is largest in the family having more than 260 species of which C. lanceolata, C.
viscosissima and C. procumbens are promising ones. Cuphea seed oil is diverse in fatty
acid composition ranging from C8 – C18, predominating in MCFA (C8 – C12) (Earle et
al. 1960; Miller et al. 1964). There is no known genus in plant kingdom with such a
diverse fatty acid composition (Anonymous, 1985; Graham, 1989; Knapp, 1993a). So
the researchers can almost tailor-select the oil composition as per need of the society.
Caprylic and capric acids, which have potential nutritional applications, are
either derived from petrochemicals (non-renewable and dwindling source) or by
fractionating coconut and palm-kernel oil (costly source). The use of capric and
caprylic acids in human diet is severely restricted due to limited availability (Knapp,
1993a). Lauric acid that has industrial importance is currently derived from coconut and
palm kernel oil. Coconut and oil palm are perennial sources and also have relatively
less lauric acid content (50%) than Cuphea (60%) (Anonymous, 1985; Singh et al.
1998). The fatty acid composition of Cuphea in comparison with coconut and oil palm
is presented in table: 5.
The lauric acid content of Cuphea makes them potential substitute for coconut
and oil palm and the caprylic and capric acid contents suggest that they could
eventually supplement or replace petrochemicals. However Cuphea is yet to be
commercialized due to hindrance of wild characters such as seed shattering and seed
dormancy (Hirsinger and Röbbelen, 1980; Anonymous, 1985; Knapp, 1993a; Pandey et
al. 2000).
6) Conclusion:
With the advent of breeding and biotechnology approaches the native fatty acid
profile of major oilseed crops particularly brassica, soybean and sunflower have been
modified to desirable extent. All oils have a place, and individual points of identity, any
of which may be usable for certain functionalities. The fatty acids, which seem to be
undesirable today, may assume importance in the future. So designing oil is a continous
process, and it is a long-term commitment to work with consumers to develop oils with
certain fatty acid profile for specific purposes, and with certain nutritional properties.
So the nutritionist, breeders and biotechnologist, should have a long-term view and
integrated approach to provide oil with required quality at any point of time.
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