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Division of Genetics and Plant Breeding National Botanical Research Institute, Lucknow. 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. 2) THE CHEMISTRY OF FATS: Fats or lipids are esters of two molecules i.e. glycerol and fatty acids. Glycerol is a sweet viscous colourless liquid. Structurally it has two primary and one secondary alcohols. Depending upon the number of fatty acids attached to glycerol, mono- (1 fatty acid), di- (2 fatty acids), and tri-glycerides (3 fatty acids) are formed. Most fat in our bodies and in the food we eat is in the form of triglycerides (TGs). The word “fat” is ordinarily used to refer to TGs that are solid or, more correctly semi solid at ordinary temperatures, whereas the word “oil” is used for TGs that are liquid under the same conditions. 2.1) Fatty acid: Fatty acid is a hydrocarbon chain with a methyl group (CH3) at one end and carboxyl group (COOH) at the other end. The three fatty acids in a TG may all be alike or may be different. The composition of fatty acids in the fat or oil determines their physical properties and nutritional qualities. So designing oil or fats involves manipulation of fatty acids to achieve the desired quality suited for specific purpose. 2.2) Classification of Fatty Acids: Generally fatty acids are classified into Saturated Fatty Acids (SFA) and Unsaturated Fatty Acids (USFA) based on bonding between carbon atoms (Table: 1). In

SFA the carbons are connected to each other only by single bond. They are not a single family of fats, but comprises three sub groups depending on chain length (Kabara, 2000): a) Short Chain Fatty Acids (SCFA) – C2:0 to C6:0. b) Medium Chain Fatty Acids (MCFA) – C8:0 to C12:0. c) Long Chain Fatty Acids (LCFA) – C14:0 to C24:0. Table: 1 Classification and Sources of Some Important Fatty Acids. Common Name Abbreviation Fatty Acid Famil y Saturated Fatty Acids Caprylic C8:0 Capric C10:0 Lauric C12:0 Myristic C14:0 Palmitic C16:0 Stearic C18:0 Arachidic C20:0 Behenic C22:0 Unsaturated Fatty Acids Oleic C18:1 Linoleic C18:2 Cuphea Cuphea Cuphea, Coconut, Oilpalm, Californian Bay Cuphea, Coconut Milk, Animal fat, Cuphea, Oil palm Cuphea, Milk, Animal fat Ground nut Ground nut n-9 n-6 * Sunflower, Safflower, Sesame, Olive, Oil palm, Corn, Groundnut, Cottonseed. Linseed, Marine oils Borage, Evening Primrose, Black Currant Brassica Groundnut Major Sources

α-Linolenic C18:3 n-3 γ-Linolenic C18:3 n-6 Erucic C22:1 n-9 Arachidonic C20:4 n-6 * Oleic and linoleic acids share common sources.

USFA have double bonds between carbon atoms. They are called unsaturated because they could hold more hydrogen atoms than they do. Based on number of double bonds they are grouped in to two: a) Monounsaturated Fatty Acid (MUFA): They have one double bond in the form of two carbon atoms double bonded to each other and therefore lack two hydrogen atoms.

b) Polyunsaturated Fatty Acid (PUFA): They have two or more pairs of double bond and therefore lack four or more hydrogen atoms. paints.Omega Fatty Acids. 3. They also have the highest caloric density of any foodstuff. 3. One system of naming USFA is to indicate the position of first double bond counting from the methyl end. chemicals. Fig: 1 . 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). as well as in products such as margarine and salad oils. technical products and biofuels.2) Non caloric functions: . baking and frying purposes.1) Caloric and related functions: Fats are important source of energy in the diets. The daily recommended intake of dietary fat is 15-35% of total calories required (Anonymous. Likewise fatty acids with first double bond at sixth carbon atom are called Omega 6 Fatty Acids (linoleic acid). coatings and resins. furnishing about 9 calories of energy per gram. since they are consumed in a relatively water-free condition whereas proteins and carbohydrates often occur with large quantities of water. These omega fatty acids (Fig: 1) are popularly called as “immunonutrients”. soaps and detergents. 1994). The terminal carbon atom is called omega carbon atom. In industries it is used in manufacture of pharmaceutical products. The oil is commonly used in human consumption for cooking. as compared with about 4 calories each furnished by proteins and carbohydrates. 3) Nutritional and Non-nutritional Functions of Fatty Acids: About 90% of world’s oil production is used for edible purposes and remaining is used for industrial purposes.

2) They are needed for the conversion of carotene to Vitamin A.linolenic acid compete for the same enzymes and have different biological roles. and then imported into chylomicrons. D.1) They act as carriers for important fat soluble vitamins A.linolenic acid (omega 3 fatty acid) which are to be obtained from external source. 1987).linoleic acid (Omega 6 fatty acid) and α. Omega 3 and omega 6 fatty acids help lower cholesterol and blood TGs and prevent clot in arteries. breast cancer and colon cancer are reduced when MCTs are used as primary dietary lipid source (Babayan. MCTs provide quick energy similar to glucose but with twice the caloric value (8. 1996). LCTs are hydrolyzed. sticky platelets and lowered immune function. 1994). It can also protect body against high blood pressure. which enter the lymphatic system. heart attacks and thrombones. Also research has indicated that heart disease. MCTs bypass the lymphatic system. 3) They are important constituents of cells and cell membranes and serve as precursors to certain harmones and acts as metabolic regulators of vital processes. Babayan. the ratio of linoleic and αlinolenic acid should be between 5:1 and 10:1. then re-esterified to triglycerides. 4) Humans can’t synthesize two of the fatty acids essential for health. where they are oxidized for energy and are not likely to be stored in adipose tissue (Ronald. (Anonymous. Bach and Babayan. which are transported via the portal vein directly to liver. water retention. inflammation. . which may result in strokes. The recommended intake in the diet is. for mineral absorption and host of other processes. They can benefit weight conscious individuals because they supply energy while not contributing to fatty acid deposits. They are metabolized differently than Long Chain triglcerides (LCT). The dietary lipids are the only source to mitigate the essential fatty acids deficiency. in particular for brain development and visual activity (Anonymous. Since linoleic acid and α. the balance between them in the diet is of considerable importance. 1982.3 calories/ gram). They are also especially important for normal fetal and infant growth and development. 1981. 1994) 5) Medium chain triglycerides (MCT) are a class of dietary lipids containing fatty acids ranging from C6 to C12. E and K. They are hydrolyzed to MCFA.

1955).6) They have impact on the functioning of the cardiovascular Non-Nutritional Functions of Edible Fats and oils: Major use of edible oil is in cooking where it is an efficient heat transfer medium and imparts flavour and palatability to foods. eliminating the risk of CHD. cholesterol and incidence of CHD. respectively than that of oleic acid (Carlson. All cooking oils are vegetable products.1) Shelf Life: The double bonds in the USFA are more prone to oxidation and polymerization. Lands. The non-nutritional uses of edible fats and oils are influenced by various physical properties as follows: 3. 3. 3. PUFA less than 10% of calories and MUFA 10-15% of calories in our diet (Ronald. Increased serum concentration of low-density lipoprotein (LDL) cholesterol is a major risk factor for cardio vascular disease while the concentration of serum high-density lipoprotein (HDL) cholesterol is inversely related to incidence of CHD.3. 1996). 1995. So SFA should make up less than 10% of calories. Another major SFA. In contrast due to lack of double bonds the SFA have more oxidative stability and thus increased shelf. The MUFA (oleic acid) and PUFA (linoleic and α. 2002) The SFAs – lauric. The amount of SFA is positively and amount of MUFA and PUFA are inversely associated with the risk of cardio vascular diseases. A wealth of nutritional and medical studies indicated strong relationship between dietary fats. which leads to rancidity and results in spoilage of edible fats and oil. 1997). stearic acid produces very little change in serum cholesterol concentration and is apparently neutral in its effect on cholesterol. (Reimenschneider. Large quantities of fats are used in the production of baked goods. Also high serum TGs concentration increases the risk of coronary heart disease (Kratz et al. 1995. They increase LDL/HDL ratio leading to incidence of CHD.2) Melting Point: .linolenic acid) reduce the LDL/HDL ratio in serum. Horrobin. They are also used in products such as margarines and shortenings. Oxidation of linoleate and linolenate is approximately 10 and 25 times higher. myristic and palmitic acids and trans-unsaturated fatty acids are cholesterol raising fatty acids.

The double bonds are rigid and introduce a kink in the molecule. 4) SYNTHESIS OF FATTY ACIDS: Fatty acid biosynthesis in plants is intracellularly compartmentalized and regulated in a tissue and development specific manner. This compound undergoes a cycle of reduction. fatty acid synthase to form a five carbon compound. darkened colour and altered flavour. Denovo fatty acid biosynthesis occurs predominantly in plastids. therefore liquid and animal fats tend to be saturated. It is more problem in catering operations where heating is intermittent and oils are used for long period. which needs crystalline structure to maintain semi-solid consistency. and in shortenings. 3. the precursor of fatty acid biosynthesis is converted to malonyl Co-A (three carbon compound) catalyzed by acetyl-CoA carboxylase. 3. In homes where oils are normally used for much shorter periods of time and discarded after being used once or twice. The length of fatty acids and their position on the glycerol backbone determine the type of crystals formed. dehydration and reduction reactions to form saturated acyl groups having four carbons.3. Generally plant fats tend to be unsaturated. which needs creamier structure.3) Crystal Formation: Types of crystals formed by fats are important in maragarine. Also melting point is influenced by chain length. the fatty acids undergo hydrolysis which results in a poor quality oil with a reduced smoke point.3. Oils rich in polyunsaturates have lower stability and can’t be reused. stability problems play a lesser role. This saturated acyl groups becomes the .4) Stability while cooking: Due to high temperature while cooking and moisture present in foods. therefore solid at room temperature. This prevents the fatty acids from packing close together and as a result unsaturated fatty acids have a lower melting point than do saturated fats. The acetyl Co-A and malonyl Co-A undergoes condensation catalyzed by condensing enzyme. Acetyl Co-A (two carbon compound). The free fatty acids produced in plastids travel to endoplasmic reticulum to get synthesized to TGs. longer chain length tends to promote a higher melting point than shorter ones.

5) Designing Oil: Oils or fats can be designed by the following three methods: 1) Chemical and physical processes. the fatty acid chain is extended by two carbon atoms. stearyol-ACP desaturase introduces a double bond converting C18:0 –ACP (saturated) to C18:1 –ACP (unsaturated).2) Hydrogenation: This method is used to convert liquid oils to solid fats. the number of carbon atoms in the chain is almost always an even number. With each passage through the cycle.substrate in another condensation with malonyl group and enters into second cycle of reactions. 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). 3) Synthetically structured fats. Since fatty acids are synthesized from fragments containing two carbons. In MCFAs producing plants such as Cuphea TE cleaves the bonds in medium chain acyl-ACPs making them free. The growing acyl groups are covalently attached via a thioester bond to the acyl carrier protein (ACP). This results in saturation and conversion of double bonds from cis to trans configuration . which are used in shortenings and margarines. The free fatty acids then cross the plastid envelope and be re-esterified to Acyl-CoA moeties and eventually be utilized as substrate for the synthesis of glycerol lipids including TGs. 2) Breeding and genetic engineering.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. which is cleaved by acyl-ACP thioesterase to release free fatty acids at the level of C16:0 or C18:0 or C18:1. 5. 5. 1991): 5.1. When the growing acyl-chain reaches the length of C18:0 –ACP.1.1) Chemical and Physical Processes (Hegenbart.

5. creation of novel genetic variation (somaclonal variation).3) Fractionation: This is the process by which oil may be separated into its different TG portions based on their individual melting points. rapid generation of homozygous lines (doubled haploids) and precise selection for desirable traits (molecular markers) can be achieved. Both these effects straighten out the molecules so they can lie closer together and become solid rather than liquid. which is ultimately decided by the genes encoding these enzymes. Interesterification also can be directed in such a way as to produce a solid fat from oil without hydrogenation.1.2) Breeding and genetic engineering: The usage of oil depends on its fatty acid profile. Conventional breeding approaches utilize either the natural genetic variation or generated variation (mutation) to develop cultivars possessing novel traits through selection or hybridization. 5. Molecular breeding approaches hasten the process of conventional breeding and reduce the time needed to develop new varieties. Through molecular breeding approaches. This is often done in fats designed for confections or margarines. 5. However further adjustments will not be realized satisfactorily without the assistance of genetic engineering (Friedt and . So breeding for an desirable oil composition involves concentration of these genes to enhance the level of require fatty acid in the cultivar. breaking sexual crossability barriers (embryo rescue.1. The synthetic MCTs are manufactured from caprylic and capric acids obtained by fractionating coconut and palm-kernel oils.4) Rearranging: This process modifies oil properties by exchanging fatty acids on TG molecules. protoplast fusion).(trans fatty acid). The procedure is called interesterification if the fatty acids simply switch positions on the molecule and transterification if the fatty acids actually change TGs. Thus classical and molecular breeding approaches in combination offers a wide spectrum of methods for efficiently designing oil with desired fatty acid composition. The oil is held at a predetermined temperature and the solids present are filtered out or are separated in some way. The fatty acid profile in turn depends upon the activity of fatty acid biosynthetic enzymes.

12:0 14:0 16:0 18:0 18:1 18:2 18:3 20:1 22:1 Others n-9 n-6 n-3 n-9 n-9 37 4 18 3 4 4 3 23 4 1 2 2 1 2 1 11 60 61 33 34 84 12 21 28 12 15 5 9 10 3 7 4 3 8 1 1 1 52 1 4 1 1 3 4 2 - - 11 10 17 8 7 4 5 3 28 4 23 23 17 20 85 54 60 55 35 1 8 2 8 7 2 - - 2 1 - - 6 4 4 18. Oil type/seed Origin/method variety Rapeseed High-erucic Traditional acid rapeseed Double-low / Spontaneous Canola mutant Low-linolenic Mutagenesis Canola Laurate Genetic Canola engineering High myristate Genetic /palmitate engineering High-oleic Mutagenesis / Canola transgenic Soybean Conventional Traditional Low Mutagenesis linolenate High palmitate Mutagenesis High stearate Mutagenesis High oleate Genetic engineering Sunflower Conventional Traditional High oleic Mutagenesis / transgenic Linseed Conventional Traditional Low linolenic Mutagenesis 5.5 2. 1991) supplying more than 12.2. Table: 2 .1) Rapeseed and Mustard Rapeseed and mustard are important brassica oil crops.0 4 16 71.0 6.5% of global edible oil (Röbbelen.5 4 78. 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.0 - - - .9% of world’s vegetable oil production (Mc Calla and Carter.5 16.5 19.5 11.5 71 0. 1987).5 - - - - - - 6. belonging to family Crucifereae and accounting for 13.Fatty acid profiles of traditional and modified oilseed crops.5 4.5 53.Wilfried).

B. 1964) partially dominant gene (Davik and Heneen. napus. E2 and E3. B. In B. The feeding experiments on animals during 1950’s revealed that reducing erucic acid to less than 2% could significantly enhance nutritional value of oil. Extensive studies on nature and number of genes controlling erucic acid synthesis has been made by several workers. campestris and e. juncea (Indian or Brown Mustard) and B. Krzymanski and Downey (1969) reported a fifth allele and designated five alleles as e. Also brassica is bred for low linolenic and high oleic types to increase their nutritive value and shelf life. 1996). juncea (AABB) and B.Ec and Ed contributing <1%. campestris. juncea (Khanna and Singh. 12%. Eb. nigra genomes has been reported (Krik and Oram. E1. 15%. Ea and Ed alleles were identified for B. B. B. napus. campestris high erucic acid content is controlled by a single (Dorrel and Downey. campestris and B. juncea two erucic acid loci. napus (AACC) are digenomic natural amphidiploids evolved by crossing among diploid species with AA. 1981) and the four alleles acting in a additive manner were designated as E0.5% erucic acid respectively. campestris var sarson (Sarson) are the major sources of edible oil in India. napus is controlled by four alleles (digenic) acting in additive manner. one each from B. Ea. campestris was previously the most dominant species but later replaced by B.Three most important species that accounts for 95% of world’s rapeseed and mustard oil production are B. 1991). B. incorporated by B. nigra and B. 10%. In contrast high erucic acid cultivars are regaining interest in industrial contexts. Eb. The brassica seed oil is characterized by presence of LCFA: eicosenoic and erucic acids. 20% and 20% erucic acid respectively. The oil was extensively used for edible purpose until the myocardial damage in rats due to erucic acid was demonstrated. napus due to its higher yield potential and improved oil and meal quality. campestris and B. This led to the development of low erucic acid variety now known as canola. BB and CC genomes. In an effort to assign erucic acid genes to individual genomes Liu and Guan (1997) studied the . The e. Harvey and Downey (1964) reported that erucic acid inheritance in B. oleraceae genome. each contributing 0%. and Ec alleles were identified for B. 30% and 3. oleraceae respectivelty. Ea and Ed are truly allelic and present on B. In B.

mid-oleic oil (65-75%). These genotypes were used in hybridization programmes either to transfer low erucic acid trait to existing brassica cultivars or to develop new cultivars with low or zero erucic acid content.. Kizakinonatane. 1996) and a second gene is linked to the second locus L2 (Barret et al.. zero or low erucic acid oil (<2%) and high erucic acid oil (60-80%) are available. Two of the QTLs for oil content showed a close association in location of the two erucic acid genes.1999) and SCAR (Ho et al. Molecular markers such as RAPD (Rajcan et al. Designing of brassica oil began with the identification of low erucic acid genotypes in brassica germplasms by plant breeders.. 1999). napus which revealed that A and B genomes each carry a pair of genes controlling seed erucic acid content. Castor. Sterling. napus cultivar Oro. Now several cultivars with zero erucic acid (Hanna. high oleic oil (>75%). juncea and B. Ericka. Conversely high erucic acid cultivars (Millenni UM 03. campestris and B. Brassica genotypes and cultivars with high/low saturated fatty acid oil.) are also available. etc. Venus. 1999) for linolenic acid are available. Neptune. Similarly studies on fatty acid profile of resynthesized B.napus from their progenitors B.napus and genes controlling erucic acid synthesis were mapped (Teutonic and Osborn.) and low erucic acid (Cyclone.interspecific progenies between B. 2002). Ecke et al (1995) mapped erucic acid genes to two linkage groups on the RFLP map and also mapped three Quantitative Trait Loci (QTL) for seed oil content on three different linkage groups. oleraceae indicated equal contribution of AA and CC genomes (Rahman.5%). Asukanonatane. Plant breeding and genetic engineering approaches have resulted in drastic modification of fatty acid composition of brassica seed oil. indicating a direct effect of the erucic acid genes on the oil content. A desaturase gene fad3 is linked to L1 (Jourdren et al. Genetic studies using “Stellar” a low linolenic acid cultivar demonstrated that two major genes L1 and L2 control low linolenic acid content. A linkage map of Restriction Fragment Length Polymorphism (RFLP) was constructed for B. 1994). etc.) are available. The low linolenic acid trait was produced by seed mutagenesis of the B. low linolenic oil (<3. etc. Sunrise. Millenni UM 02. which led to isolation of a mutation line M11 with an altered C18:2/ .

Comparison of doubled haploid breeding with conventional breeding revealed that best conventionally produced line gave an erucic acid yield of only 10. Doubled haploids (DH) obtained through microspore culture have been extensively used for fatty acid modification in brassica.8 – 60. napus (Heath and Earle. 1988). rapa var oleifera to resynthesize B. Stellar a B.7 dt/ha in comparison with 11. et al. The oleate at sn-2 position of PE is then desaturated to linoleate and . Either oleate can be elongated to erucic acid by fatty acid elongase or enter the phospholipid by lysophosphatidyl ethanolamine acyltransferase (LPAAT) which acylates the sn-2 hydroxyl group of lysophosphatidyl ethanolamine (LPE) to form phosphatidylethanolamine (PE). oleraceae var botrytis and B. one cotyledon can be dissected for determination of fatty acid composition and remaining part of the embryo can be cultured to give a regenerated plant. napus cultivar with low linolenic acid (3%) was developed in a backcrossing programme of M11 with cultivar Regent (Scarth et al. Oleate that is transported from ACP track (chloroplast) to the CoA track (endoplasmic reticulum) by catalytic action of β-Ketoacyl-ACP Synthases (KAS) is at the branch point in the erucic acid metabolism. napus. 1992). Cegielska et al.C18:3 ratio (Rakow. to produce low saturate germplasm for further cultivar development (Scarth and McVetty). rapa lines with reduced saturated fat levels have been developed through microspore mutagenesis and this variation can be introduced in to B. (1999) developed 9 DH lines with high erucic acid content ranging from 56. At this stage. a precursor of triacylglycerol. The correlation between cotyledons and the seeds produced by regenerated plants for erucic acid content (Albrecht. Protoplast fusion of zero erucic acid cultivar Hanna with Lesquerella fendleri followed by crossing with High Erucic Acid Rape line (Schröder et al. napus at cotyledonary stage contains large amount of storage lipids. equal or similair in fatty acid composition to those found in seeds of homozygous donor plants. 1999) and protoplast fusion of B. 2000) was found to be significant.4%.9 dt/ha of the first generation DH line (Listl. Microspore derived embryoids of B. 1995) and oleic acid content (Möllers et al. So selection for desired fatty acid composition can be made at cotyledonary stage itself. 1993). DH B. 1995) have resulted in high erucic acid types.

campestris) and B. napus genes Bn-FAE 1 and BnFAE 2 corresponding to its parental species B. B.linolenate by desaturase (Fig: 2). Fourmann et al. These genes had 98%. CE7 and CE8 homologus to Arabdiopsis FAE 1 gene and found tight linkage of one of the FAE 1 genes to E1 locus. Fig: 2 . The FAE 1 genes from low and high erucic acid lines differ at 13 positions at amino acid sequence level. Manipulating the levels of the enzymes KAS and LPAAT can control the accumulation of erucic acid in seed lipids. Elongase Acetate → → → 16:0-ACP → 18:0 -ACP → 18:1-ACP ↓ Thioesterase Plastid stroma (ACP track) Oleic acid Acyl-CoA synthetase Oleoyl-CoA → PE-18:1 → PE-18:2 Acyltransferase δ -12 desaturase Endoplasmic Reticulum Adapted from Rajashekaran.Biosynthesis of oleate and its desaturation . rapa (B. 84% and 58% nucleotide similarity with FAE 1 genes from B. Arabdiopsis thaliana and Simmondsia chinensis respectively. Alternatively erucic acid content can be increased by reducing the levels of LPAAT through antisense expression and there by increasing the availability of oleate for elongation reaction (Rajashekaran). 86%. brassica and groundnut systems. From B. napus. Genes encoding LPAAT has been isolated from yeast (SLC1-1). LPE → 18:3 δ -15 desturase 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. Over expression of LPAAT in transgenic plants reduce the availability of oleate for the formation of erucic acid and there by redirecting the pathway towards PUFA synthesis. oleraceae respectively. napus Barret et al (1998) isolated two sequences. Also they reported co-segregation of these genes with E1 and E2 loci respectively. juncea. (1998) designed PCR primers corresponding to FAE 1 gene and amplified two B. mainly localized in the central part of protein .

2002). Since erucic acid alleles are additive in nature. 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. soybean seeds contain high amount of protein (42-45%).2. However. 2002). 1996). theoretical expectation of erucic acid yield through conventional breeding is only 66-67%. It also has significant amount of palmitic acid (9-10%). 1971). the oil gets oxidized readily leading to off type flavour and poor keeping quality due to high amount of linolenic acid.sequence (Das et al. The high content of linoleic acid makes soya oil suitable for edible purposes.2) Soybean: Soybean (Glycine max) tops among all oilseed crops with 54% of world oilseed production. Cargill’s Clear Valley 75 is a high oleic (75%) cultivar (Scarth and McVetty). either through co-suppression or antisense technology. This is because erucic acid occupies only sn-1 and sn-3 positions of the glycerol molecule (Appelqvist. isolated from Umbellularia california (Californian bay). Lassner et al. High oleic canola (> 86%) has been produced using seed specific inhibition of microsomal oleate desaturase and microsomal linoleate desaturase gene expression. 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%). Co-suppression has been used in combination with mutation treatments to produce modified fatty acid profiles (Debonte and Hitz. 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. The high laurate trait was the result of insertion of the acyl-ACP TE. Taylor et al. High laurate canola is the world’s first transgenic oilseed crop in commercial production. 2000). Besides oil. So oil from soybean cultivars with <1% linolenic acid. This altered amino acid sequence in variant β-KetoacylACP 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. 2001. which will have improved oxidative . (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. 5.

Seed size is positively correlated with oleic and stearic acids and negatively correlated with linoleic and linolenic acids. 2001). Kwon and Shin. Nian et al. The linolenic acid locus designated as fan. Maestri et al. protein content and seed size have been reported by several authors (Zhang. 1968) and governed by additive genes (Mc Kendry et al.6% of the total fatty acids respectively. olaola. ola. Liu et al. Genetics of three major fatty acids of soybean oil viz. 1996. 1998. and ol respectively (Takagi and Rahman. The genotypes of Bay. 1985). Linoleic and linolenic acids are positively correlated with each other and negatively associated with oleic acid.. 30. Ol and fanxa . 1991. however oleic acid is positively correlated with crude protein content.stability.8% and 48. palmitic. 2002). Stolzfus et al. Rahman et al. olol respectively with average oleic acid content 27. So designing of soya oil is primarily targeted towards low linolenic followed by high oleic and palmitic types. 2000. The association of palmitic acid is positive with linoleic and linolenic acids and negative with oleic acid. Oleic acid alleles of Bay. 1994) are high oleic acid mutants of soybean derived from cultivar Bay via treatement with X-rays. M11 and M23 are designated as Ol. 1996. Oil and protein content are negatively correlated traits. oleic and linolenic have been studied well. reducing the formation of undesirable flavour compounds is considered desirable. 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. 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. So in breeding programmes selection for larger seeds will increase oleic and decrease linolenic acid content in seed oil. M11 and M23 are OlOl. and fanxa locus is responsible for low linolenic acid content (Rahman et al.8%. 1995. Also oils rich in oleic acid that have improved flavour and nutritional value is preferred. Correlation among individual fatty acids and fatty acids with oil content. Soybean oil with elevated palmitate content may be useful for producing solid fat (for baked products) at room temperature without hydrogenation. M11 and M23 (Rahman et al. The inheritance of oil content is influenced by maternal effects (Brim et al. 1996).

1996). 1984). Miller et al. High oleic soybean oil showed greater oxidative stability than other high oleic oils. partially domonint gene designated as Ol. 1996).2. 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. high palmitate line (A19) and high oleate lines (M11 and M23) are developed. low palmitate line (A18).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. Soybean cultivars with high oleic acid (Bay) and low linoleic acid (Murayutaka) have been bred. The development of sunflower with high oleic acid content was reported by Soladatov (1976).are independently inherited and combination of these two loci resulted in a germplasm line DHL with high oleic and low linolenic acid content. including sunflower. M11 and M23 using microsomal -6 fatty acid desaturase cDNAs as probe resulted in identification of a band (4. RFLP analysis of Bay. Pervenets is a high oleic acid cultivar developed through mutation breeding (Miller and Vick.6 kb) present in Bay and M11. 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. ml. Also genetically engineered high oleic acid soybean cultivars are available. canola and corn (Ronald. 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. who further reported a second gene. A single. 1998). However sunflower oil with high oleic acid is preferred due to its oxidative stability. The presence of recessive gene ml in homozygous condition along with gene Ol. 5. (1987) confirmed this.5%). and absent in M23 (Kinoshita et al. Through mutation breeding low linolenate lines (A5. So down regulation of FAD 2-1 will elevate oleic acid content in seed oil. . controls the high oleic acid trait in sunflower. A6). results in high oleic acid content.

1965. A variety under constant 10◦C produced about 80% linoleic acid while at 26. The presence of high linolenic acid in linseed oil causes rancidity and renders it unsuitable for edible purpose. for use in the production of paints.5◦C the linoleic acid content was dropped to nearly 25%. 1998). Downes and Tonnet. The high level of linolenic acid in the oil (45-65%) imparts rapid drying property in such products. However the sunflower industry had difficulty in maintaining very high oleic acid level and elected to commercialize. varnishes. USA in co-operation with private industries have released new class of sunflower called “NuSun” having mid oleic composition (Johnson. 1985. 1964. Encapsulated linseed oil is available commercially. 1982). ARS. 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. a mid oleic acid (60%) oil composition (Downey). Several investigators have reported that there is inverse correlation between prevailing temperature during growth period and linoleic acid content. Canvin.The relative proportions of oleic and linoleic acids in sunflower oil are under both genetic and environmental control. 1986). Kawanabe.2. Temperature stable high oleic acid strain (86%) was developed by treatment of cultivar Peredovik with chemical mutagens (Prudy. 1979. Since the demand for industrial quality linseed oil is declining due to synthetic substitutes and markets for vegetable oil is expanding. an omega 3 fatty acid and also contains average content (18-20%) of linoleic acid (omega 6 fatty acid). Linseed is the richest plant source of (alpha) linolenic acid. . In contrary high linolenic acid in linseed has valued it as a nutritionally desirable crop. and the opposite is true for oleic acid (Kinman and Earle. 1965). 5. inks and linoleum. So to convert linseed in to premium edible oil linolenic acid would have to be reduced considerably to a maximum of 3%. efforts are on to develop edible quality linseed oil.4) Linseed: Linseed or Flax (Linum usitatissimum) has traditionally been utilized as a source of industrial oil. and this was accompanied by simultaneous rise in oleic acid content (Canvin.

The linolenic acid content of these mutant lines constituted approximately 29% compared with 43% in Glenelg (Green and Marshal. 1986b). Further crossing these two mutant lines led to development of a mutant genotype having less than 2% linolenic acid (Green.13 14 – 39 14 . The virtual elimination of linolenic acid (<2%) from the seed lipids is accompanied by an equivalent increase in the content of linoleic acid (>46%). 1999) are now commercially grown and consumed in Canada. the proportions of other fatty acids remaining unchanged. 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. Two mutant lines M 1589 and M 1722 were developed following EMS mutagenesis of cultivar Glenelg. 1984). 1996. Dribnenki et al.85 Linola 6 4 10 16 16 72 2 74 . Australia and several European countries (Table: 3). 1986a). The mutant locus in M 1589 and M 1722 are designated as Ln1 and Ln2 respectively. 1984). exhibiting additive (co-dominant) gene action (Green. 1959. 1981) indicating mutation breeding to be a promising approach rather than hybridization and selection to reduce linolenic acid content (Green and Marshal. Green. United States. Fatty Acid Profile Palmitic Stearic Total Saturates Oleic Total Monounsaturates Linoleic α-linolenic Total Polyunsaturates Flax 4–9 2–4 6 . Green and Marshal. 1986a).39 7 – 19 35 – 66 42 . 1995. Table: 3 – Fatty acid profile of linola in comparison with flax. Dribnenki et al. Varieties producing edible linseed oil called “Linola” (Dribnenki and Green. These changes indicated that the mutation block the final desaturation of linoleic to linolenic acid (Green and Marshal. 1984.Extensive surveys of Linum usitatissimum germplasm collection revealed that variety mean for linolenic acid content varied only between 45% to 65% (Zimmerman and Klosterman.

1989). linoleic and stearic acids designated as olol. 2002). Variants with high stearic (4-11%). Safflower is one of the best examples of variability for fatty acid composition of seed oil. Oil Type Genotype Fatty Acid Content in Safflower Oil (% range) C16:0 C18:0 C18:1 C18:2 Palmitic Very High Linoleic OlOl lili StSt High Linoleic OlOl LiLi StSt High Oleic olol LiLi StSt Intermediate Oleic ol’ol’ LiLi StSt High Stearic OlOl LiLi stst Adapted from Muralidharan et al. High linoleic/ low oleic acid allele is dominant over high oleic/ low linoleic acid allele indicating single allele control of oleic to linoleic acid conversion. An interesting fact in this crop is that high or low oleic acid lines are stable to temperature changes but the intermediate ones are affected indicating that different alleles respond differently to temperature variations. 2002. Table: 4 . lili and stst respectively are major recessive genes at different loci (Table: 4).2.5. Increase in stearic acid is accompanied by decrease in oleic or linoleic acid or both. The three genes that control production of oleic. high oleic (>80%) and high linoleic acid concentration (>85%) have been identified and are currently available as varieties (Muralidharan et al.Genetics of fatty acid content of different oil types in safflower.6) Sesame: .5) Safflower: Like sunflower. 3-5 6-8 5-6 5-6 5-6 Stearic 1-2 2-3 1-2 1-2 4-11 Oleic 5-7 16-20 75-80 41-53 13-15 Linoleic 87-88 71-75 14-18 39-52 69-72 5.2. safflower (Carathamus tinctorius) oil is predominant in linoleic acid (70-80%) with low linolenic acid content. It is the first oil seed crop in which individual gene control of oleic and linoleic acid was demonstrated due to efforts of Furehally (reported by Knowles.

The Virginia botanical types generally have higher oleic acid content and lower linoleic acid content than Spanish or Valencia types. Variation for fatty acid content was induced by gamma rays (Lee et al.. Singh. but their implications in heart disease is a matter of concern (Kritchevsky et al. 1979). Cuphea seed oil is diverse in fatty acid composition ranging from C8 – C18. Sesame oil is unique in containing several lignan antioxidants as well as some tocopherols. sesamin and sesamolin and their derivatives.2. Oleic and linoleic acids constitute around 85% of oil composition and their inheritance is controlled by single gene (Brar and Ahuja.. procumbens are promising ones. which has high oleic acid content. 1971). These LCFAs are useful in emulsification and stabilization of products like peanut butter. C.The seed oil of sesame (Sesamum indicum) contains mainly four fatty acids viz. lanceolata. sesamol and sesaminol. 1994).8) Cuphea: The genus Cuphea belongs to family Lythraceae (Graham. So far not much efforts for fatty acid modification has been done in this crop. Crosses among these types indicated that sufficient variability for fatty acid could be generated by recombination of genes. The high oleic acid allele (Ol) is dominant over low oleic acid allele (ol).7) Groundnut: Groundnut (Arachis hypogea) oil is composed of 80% unsaturated fatty acids and unique in containing LCFAs. predominating in MCFA (C8 – C12) (Earle et . The lignans. 1985) and by sodium azide (Kang. 5. and their related compounds prevent the oxidation of sesame oil contributing to the characteristic stability and extended shelf life. 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. viscosissima and C. 1988. 2001) and is largest in the family having more than 260 species of which C. 1974). palmitic. oleic and linoleic acids. stearic. 5.2. These efforts resulted in release of Seodun in 1997 in South Korea. arachidic and behenic acids.

1985. procumbens 1. Table: 5 – Fatty acid composition of Cuphea in comparison with other sources. Knapp. wrightii 29. There is no known genus in plant kingdom with such a diverse fatty acid composition (Anonymous.5 4 50 14 28.3 3. procumbens are caprylic and capric acid rich. which have potential nutritional applications. laminuligera 17.3 1. are either derived from petrochemicals (non-renewable and dwindling source) or by fractionating coconut and palm-kernel oil (costly source). Caprylic and capric acids. viscosissima. Graham.0 0.4 53.4 9 C.1 2.1 62.1 11. 1960. koehneana 0. C.1 75. The use of capric and caprylic acids in human diet is severely restricted due to limited availability (Knapp. 1993a).3 1. 1985. Coconut and oil palm are perennial sources and also have relatively less lauric acid content (50%) than Cuphea (60%) (Anonymous. 1989.2 95. Lauric and myristic acids are minor constituents of . 1993a). Miller et al.1 C. So the researchers can almost tailor-select the oil composition as per need of the society.9 5. Singh et al.1 1. viscosissima 9.6 9. 1993a.3 11. lanceolata 87.3 3. 1964).5 (Kernel Oil) C. 2000). Knapp.5 3. lanceolata and C. 1985. 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.5 2.5 10. 1998). However Cuphea is yet to be commercialized due to hindrance of wild characters such as seed shattering and seed dormancy (Hirsinger and Röbbelen. SOURCES DISTRIBUTION (% OF TOTAL FATTY ACIDS) C8:0 C10:0 C12:0 C14:0 Others Coconut 8 7 48 18 19 Oil Palm 3. The fatty acid composition of Cuphea in comparison with coconut and oil palm is presented in table: 5.2 C. Pandey et al.6 C.7 91.8 The seed oil of C. Lauric acid that has industrial importance is currently derived from coconut and palm kernel oil.6 C. These species are nearly domesticated and could supply natural MCTs with minimal processing. 1980.0 1.

a capric acid rich species Fat B gene family of atleast four members was identified (Topfer et al. engineering existing oilseed crops for MCFA synthesis has been considered as commercially viable alternative. Several transgenic . 1999). Since wild characters have hindered commercialization of Cuphea. Knowledge of biosynthetic and catabolic enzymes regulating the composition and levels of these unusual fatty acids is very much essential for engineering seed oil biosynthesis. 1993b and Tagliani et al. Similarly two cDNAs from C. Cp Fat B1 strongly prefers C8:0-ACP whereas Cp Fat B2 strongly prefers C14:0-ACP and the latter is kinetically superior over former resulting in predominance of C14:0 in C. Based on sequence homology they are classified into two families.these species. 1996a). wrightii (Cw Fat B1 and Cw Fat B2) have been isolated (Dehesh et al. Cp Fat B1 and Cp Fat B2 have been isolated from C. lanceolata. Two TE cDNAs. 1996b). CPR-2. viscosissima line PI-534911 (Knapp. The inheritance pattern of these mutant lines was studied by Knapp et al. These lines are homozygous for mutations induced by EMS and are near isogenic lines of the wild type C. In C. CPR-7 and CLM-1 (Knapp. 1995). 1995). paulistris that accumulates 64% myristate and 20% caprylate (Dehesh et al. 1993b. 1991. that prefers C18:1-ACP and saturated acyl-ACPs as substrates respectively. Tagliani et al. and CPR-4 and CLM-1 are non allelic mutations. 2001). hookeriana (Ch Fat B1-3 and Ch Fat A) and C. (1997) and they reported that CPR-1 and CPR-2 are allelic mutations affecting the cpr (capric acid) locus. Fat A and Fat B. thioesterases (TE). 1993b. 1995). Tagliani et al. So the spectrum of oils produced by these species has been increased by several induced fatty acid mutants (Knapp and Tagliani. Knapp. VS-320 an F3 line developed by crossing CPR-1 and CLM-1 produces oil with elevated levels of medium and short chain TGs that may be a potential substitute for diesel fuel (Geller et al. CPR-4. Cuphea has served as a model organism and key enzymes. CPR-6. Among these are several C. CPR-5 is an allele of cpr locus or locus tightly linked to cpr. viscosissima mutant lines with decreased capric acid – CPR-1. β-Ketoacyl-ACP Synthases (KAS) and acyl transferases are best characterized. 1995). paulistris seed oil (Dehesh. TE is the important enzyme that converts the composition of TGs from the common LCTs to unusual MCTs.

The knowledge gained will certainly pave way for engineering MCFA biosynthesis in traditional oil seed crops like canola increasing availability of MCFAs in the world oil market. Two approaches have been taken: 1) Attaching planned ratios of long-chain (LC) saturated fatty acids with very low caloric density and shorter-chain (SC) fatty acids with slightly lower caloric density than LC fatty acids (caprenin. wrightii KASA (Slabaugh et al. 2001). Since the first method results in a triglyceride found in nature the regulatory route is simple whereas for second one it is more complex. salatrim) to glycerol back bone or 2) Attaching fatty acids to a non-glycerol backbone in such a manner that the molecule is poorly absorbed in the body (olestra). capric and behenic acid. 5. The presence of encoded product of KASA. a 46 kD polypeptide. 1998). 1998). 5.3) Synthetically Structured Fats: Synthetically structured fats are designed to look and act like fats. condensing enzymes (KAS) could also influence the fatty acid chain length.1) Glycerol Back Bone: The first product commercialized under this grouping was Caprenin. The first reported breakthrough in obtaining a condensing enzyme with altered substrate specificity was the cloning of the C. Behenic acid is only partially absorbed by the body. 1996).experiments in Arabdiopsis and canola revealed the discrepancy in fatty acid profile and quantity of MCFAs between transgenic plants and native plants (Dehesh. 2001). hookeriana (Dehesh et al. resulting in a total caloric density for caprenin of 5 kcal/gram. a reducedcalorie designer fat consisting of three fatty acids: capryllic. Another KAS cDNA has been cloned from C. Expression of this KAS in canola together with Cp Fat B1 or Ch Fat B2 resulted in increase of the total levels of MCFAs in transgenic pool upto 30% and also the proportions of C8:0 and C10:0 relative to the transgenic plants expressing TE alone was altered dramatically (Dehesh. Caprenin was commercialized by Procter & . and the medium-chain fatty acids have lower caloric densities than longer-chain fatty acids. correlates strongly with the synthesis of MCFAs in different species of Cuphea. This indicated that apart from TEs. but they contribute fewer calories and less fat (Ronald.3.

and it has physical properties comparable to conventional fats. The complexity of the molecule inhibits the activity of digestive enzymes required to break it down. salatrim contributes a total of 5 kcal/gram. may assume importance in the future. S. Unfortunately. Due to the lower caloric density of stearic acid and the short-chain fatty acids.Gamble as a cocoa butter replacer and was launched in two products. The fatty acids. So the nutritionist. C. Therefore. 7) References: 1) Albrecht. . resulting in its withdrawal from the market. All oils have a place. breeders and biotechnologist. should have a long-term view and integrated approach to provide oil with required quality at any point of time. Breed. which seem to be undesirable today. the product has difficult tempering characteristics and appeared to increase the serum cholesterol slightly. soybean and sunflower have been modified to desirable extent.. Pl.2) Sucrose Backbone: Olestra is synthesized from sucrose and vegetable oil (cottonseed or soybean).. and with certain nutritional properties. and Röbbelen. Salatrim. and individual points of identity. any of which may be usable for certain functionalities. contributing no fat or calories to foods. 6) Conclusion: With the advent of breeding and biotechnology approaches the native fatty acid profile of major oilseed crops particularly brassica. is another family of restructured fats developed by Nabisco Foods.3. So designing oil is a continous process. olestra passes through the body undigested. 114(3) : 210-214. The product has been commercialized but it is unfortunate that it may cause abdominal cramps and loose stools and inhibits the absorption of some vitamins and other nutrients. Möllers. and it is a long-term commitment to work with consumers to develop oils with certain fatty acid profile for specific purposes. Safety studies revealed that the molecule has no effect on serum cholesterol and on absorption of fat-soluble vitamins. 1995. 5. G — Selection in vitro for erucic-acid content in segregating populations of microspore-derived embryoids of Brassica napus.

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