LIPIDS FOOD SCIENCE AND TECHNOLOGY BS NUTRITION AND DIETETICS 1 ST SEMESTER 1 Department of Botany G.S.S.C Peshawar.
LIPI D S Definition Structure Properties Sources Functions & Uses Classification FATTY ACIDS Introduction Classification Physical Properties Chemical Properties FATS & OILS Introduction Properties Classification WAXES Introduction beeswax
LIPIDS INTRODUCTION lipids are a group of naturally occurring substances characterized by their insolubility in water and solubility in some organic solvent. They occur widely in the plant and animal kingdom in the form of oils and fats respectively.The basic structure of lipids is comprised of carbon,hydrogen,oxygen . The lipid fat content of food is the major determinant of the energy density of diets. Fats are essential for the human body, comprising about one-sixth of our body weight. They are integral components of cells and tissues throughout the body. Vital organs such as the brain, heart, and liver are protected by fat deposits.
LIPID STRUCTURE Lipids are the polymers of fatty acids and that contain a long, non-polar hydrocarbon chain in which the tail is hydrophobic in nature and with the small polar head of molecule carboxyl group or containing oxygen , which is hydrophilic in nature.
LIPIDS Lipids are the structural and functional building blocks of the living cells and they are made up of hydrocarbons with highly reduced form of carbon. Or Lipids are the substances of animal or plant origin and comprise of (a). fixed oils , (b). fats , (c). waxes and their derivatives . Examples of Lipid :- Fats, oils, waxes ,certain vitamins (such as A, D, E and K), hormones and most of the call membrane that is not made up of protein.
LIPIDS Composition - Lipids encompass all fats and related compounds, derived from the Greek word " lipos " meaning fat . - Similar to carbohydrates, lipids contain carbon, hydrogen, and oxygen, with some containing phosphorus and nitrogen. - Lipids have fewer oxygen atoms compared to carbohydrates, resulting in more energy release (about 2.25 times) per gram during oxidation. - Body fat constitutes 15-20% of body weight in healthy non-obese men and 18-25% in healthy non-obese women. - Sedentary lifestyles and aging can lead to increased body fat if physical activity levels decline. - Lipids are widely distributed in nature and soluble in organic solvents like ether, chloroform, and benzene. - Important groups of lipid compounds include fatty acids, fats and oils, phospholipids, sterols, and lipoproteins.
PROPERTIES OF LIPIDS Lipids are oily greasy, non-polar molecules , stored in the adipose tissue of body. They are a heterogeneous group of compounds , mainly composed of hydrocarbon chains. They are energy rich organic molecules , which provide energy for different life processes. Insoluble in water but soluble in organic solvents . Hydrophobic or amphiphilic compounds. Fixed oils and fat float in water since their specific gravity less than one. Produce permanent stain on the paper. Fixed oil and fat are nonvolatile and can’t be distilled without their decomposition. They are significant in biological systems as they form a mechanical barrier dividing a cell from external environment known as the cell membrane.
SOURCES OF LIPIDS Found in all living organisms including humans , plants and animals . Lipids exists in tissues in many forms. Simple lipids are often part of large aggregates in storage tissues, such as oil bodies or adipose tissue. In plants lipids are stored in the form of triglycerides . The most known is jojoba , which stores its seed lipid as a liquid wax . In oilseeds (sunflowers, linseed) the cotyledons of the embryo are the major sites of lipid accumulation. Endosperm of the bean, coriander or carrot, is the main site of lipid accumulation. In tobacco, both embryo and endosperm tissues store lipids. Hu man tissues c o n tai n i n g fats Jojoba seeds oil Linseed oil Sunflower oil Coriander seeds oil -Tobacco plants and seed-
FUNCTIONS & USES OF LIPIDS Lipids are important source of metabolic energy (ATP ) so they are the most energy rich of all the nutrients which provide energy for different life processes . They form the structural components of the cell membranes. They serve as the biological carriers for the absorption of fat soluble vitamins A,D, E and K. Lipids are also act as lubricants for the passage of food. Maintenance of temperature . In the base of oil injections . In edible/food oils . In antiseptic preparations ( Tea tree oil is often used in diluted form as a topical antiseptic for minor cuts, wounds, and skin infections) . In the treatment of rickets . In varnishes and paint industries . In cosmetics . Also possesses antibacterial properties .
CLASSIFICATION OF LIPIDS
LIPIDS Classification of Lipids
LIPIDS Simple Lipids Simple Lipids are esters of fatty acids with alcohols. The hydrolysis of a simple lipid may be expressed as Simple lipid + H2O hydrolysis fatty acids + alcohol Simple Lipids can be sub-divided into: 01. Fats and Oil 02. Waxes
FATS & OILS If a substance is liquid at 15-16.5 C it is called Fixed oil and solid or semisolid at the above this temperature , it is called Fat. For example lard, fish oil, ghee, olive oil etc. They are made from two kinds of molecules : Glycerol (a type of alcohol) and various straight chained monocarboxylic acids known as fatty acids . The fatty acids of natural fats have 4-24C atoms (and any even numbers). These fatty acids may be saturated, monosaturated, polysaturated or cyclic unsaturated. Fats and oils are commonly called triglycerides or triacylglycerol . Fats normally saturated fatty acid esters and fixed oils mostly composed of unsaturated fatty acid esters .
LIPIDS(FATS) Fats and Oil Esters of fatty acids with glycerol. Solid at room temperature. Some are liquid at room temperature, and are known as oils. Physical state depends upon the nature of fatty acids. Fats are rich in saturated fatty acids. Oils are rich in unsaturated fatty acids . If the hydrolysis of a simple lipid yields three fatty acids and glycerol, the simple lipid is called a fat or an oil
Fats Esters of fatty acids with glycerol . Solid at room temperature longer chains saturated(only C-C) eg . animal fat, butter Fats are solid triglycerides Oil Esters of fatty acids with glycerol Oil are liquid at room temperature, and are known as oils. Oils are rich in unsaturated fatty(C=C) acids . eg . many vegetable oils, (olive, sunflower) Oils are liquid triglycerides
Slide Title 18 Department of Botany G.S.S.C Peshawar.
LIPIDS(FATS) b.Waxes Esters of fatty acids with (usually long chain) with alcohols other than glycerol. These alcohols may be aliphatic or alicyclic.Cetyl alcohol is most common found in waxes. Waxes are used in the preparation of candles, lubricants,cosmetics,ointments , polishes etc .
Properties of Fats & Oils Fixed oils are thick, viscous, yellow-colored liquids with a characteristic Odour. They are non- volatile and cannot be distilled. They do have food value and can be saponified. They turn rancid on storage due to free acidity. Fixed oils and fats are insoluble in water and ethyl alcohol , but soluble in organic solvents like chloroform, ether and benzene etc. Fats and oils are esters of glycerols and fatty acids . The oils and fats also contain various quantities such as vitamins, sterols, antioxidants, phospholipids, pigments and traces of hydrocarbons, and ketones , responsible for specific odours and flavors of these oils. Physiologically, they are emollients and demulcents. Fats are mostly obtain from animal sources and solids at room temperature , oils are mostly obtain from plant sources and liquids at room temperature . There are notable exceptions , such as cocoa butter , which is a solid vegetable oil , and cod liver oil , which is a liquid animal fat.
Classification of Oils & Fats An oil that hardens to a tough, solid film after a period of exposure to air, contains more than 50% of polysaturated acids, a key component of oil paint & varnishes. For example, linseed oil, hemp, walnut oils etc. An oil which partially hardens when it exposed to air and contains 20-50% of polysaturated acids. For ex ampl e , c a st or oil, mustard oil, sesame oil. An oil that does not harden when it exposed to air and contains less than 20% of polysaturated acids. And use in food, skincare products and to condition pliable materials such as leather boots. For example, olive oil, almond oil, peanut oil etc. E x ampl es of fats include peanut, cocoa butter and coconut oil etc. Fats – Bone tallow. Oils – Cod liver oil, shark liver oil and whale oil etc. Fats – Lard , mutton- tallow and butter suet etc. Oils – Lard oil, neat foot oil etc.
Compound Lipids
Compound Lipids Compound lipids are class of Lipids C hemically Esters of Fatty acids with Alcohols attached with Additional groups.
A dditional Groups in Compound Lipids may be either of these: Phosphoric acid Nitrogenous Base Carbohydrate moieties Proteins Sulfate groups
COMPOUND LIPIDS Esters of fatty acids with various alcohols along with an additional group. Others Glycerphospholipids - Phosphatidyl choline - Phosphatidyl ethanolamine - Phosphatidyl serine - Phosphatidyl inositol - Cardiolipin - Plasmalogens Sphingophospholipids Cerebrosides Gangliosides Globosides Lipoproteins Aminolipids Phospholipids Glycolipids
3 Main Compound Lipids These are further divided into Phospholipids Glycolipids Lipoproteins
PHOSPHOLIPIDS Phospholipids are compound containing fatty acids and glycerol in addition to a phosphoric acid , nitrogen bases and other substituents. They are present in large amounts in nerve tissue, brain, liver, kidney, pancreas and heart . Phospholipids look like triglycerides, but contain a phosphate attached to glycerol in place of one fatty acid. For example, lecithin, a phospholipid contains choline-phosphate attached to one hydroxyl of the glycerol molecule. They are further classified into, Glycerophospholipids Sphingolipids .
PHOSPHOLIPIDS FUNCTIONS They are powerful emulsifying agents and are essential for the digestion and absorption of fats Emulsifiers like phospholipids prevent separation of oil and water in food. Lecithin ( phosphatidylcholine ) found in egg yolk, honey, and mustard, is a popular food emulsifier . Mayonnaise exemplifies lecithin's ability to blend vinegar and oil, creating a stable, spreadable condiment. Emulsifiers enhance the appearance of food by preventing separation and ensuring uniformity. They also increase the freshness of sauces and creams. Vital for maintaining texture, consistency, and flavor in various food products. Enable the creation of appealing and convenient food items for consumers . Phospholipids help to carry lipid particles across the cell membrane in the blood stream
Exogenous And Endogenous Sources Of Phospholipids
Two Types of Phospholipids are : Glycerophospholipids: Glycerol containing Phospholipids Sphingophospholipids: Sphingosine/ Sphingol containing Phospholipids.
GLYCEROL FATTY ACID FATTY ACID P HEAD GROUP PHOSPHOLIPIDS Glycerophospholipids Sphingophospholipids
Depending upon Nitrogenous and Non Nitrogenous moiety attached. Examples of 7 Glycerophospholipids are: Phosphatidic Acid (Simplest PL) Phosphatidyl Choline (Lecithin) Phosphatidyl Ethanolamine (Cephalin) Phosphatidyl Serine (Cephalin ) Phosphatidyl Inositol / Lipositol Phospatid al Ethanolamine / Plasmalogen DiPhosphatidyl Glycerol / Cardiolipin
Phosphatidic acid is a simplest Glycerophospholipid Phosphatidic acid serve as a precursor for biosynthesis of other Glycerophospholipids Phosphatidyl Choline ( Lecithin ) is most commonest and abundant Glycerophospholipid in body. Phosphatidyl Choline is commonly called as Lecithin . Derived from word ‘ Lecithos ’ meaning Egg Yolk . This phospholipid is composed of a choline head group and glycerophosphoric acid, with a variety of fatty acids. Usually, one is a saturated fatty acid and the other is an unsaturated fatty acid .
They are widely in nature various oil seeds like soyabeans and the yeasts are important source from plants. They lecithins are required for the normal transport & utilization of other lipids, especially in the liver . Recently,egg lecithin has been used in the treatment of accuired immunp deficiency syndrome(AIDS).
They are widely in nature various oil seeds like soyabeans and the yeasts are important source from plants. They lecithins are required for the normal transport & utilization of other lipids, especially in the liver .
It plays a key role in cell cycle signaling , specifically in relation to apoptosis. Phosphatidylserine plays a role in blood coagulation (clotting). Phosphatidylserine coming from plants and phosphatidylserine coming from animals differ in fatty acid composition. https:// perfectketo.com/phosphatidylserine /
Cardiolipin Diphosphatidylglycerol It consist of two molecules of phosphotidic acid held by an additional glycerol through phosphate group Function : Plays a key role in apoptosis. An important component of inner mitochondrial membrane.
SphingoPhospholipids/ Sphingophosphatides
Sphingophospholipids
Sphingolipids , the fourth large class of membrane lipids, also have a polar head group and two nonpolar tails. but unlike glycerophospholipids they contain no glycerol. Sphingolipids are composed of one molecule of the long-chain amino alcohol. sphingosine (also called 4-sphingenine) or one of its derivatives, one molecule of a long-chain fatty acid, and a polar head group that is joined by a glycosidic linkage in some cases and a phosphodiester in other
Sphingomyelin is an example of Sphingophospholipid .
Sphingosine is linked with a Fatty acid by an amide linkage to form Ceramide . Ceramide is then linked to Phosphoric acid and Choline to form Sphingomyelin.
When a fatty acid is attached in amide linkage to the NH 2 on C-2, the resulting compound is a ceramide . Ceramide is the structural parent of all Sphingolipids .
SPHING FATTY ACID O SINE CARBOHYDRATE Glycolipids/ glycosphingolipids
Glycolipids/glycosphingolipids Essential components of all membranes in the body. greatest amounts in nerve tissue Functions regulation of cellular interactions, growth, and development CEREBROSIDES GLOBOSIDES GANGLIOSIDES SULFATIDES
Cerebrosides ceramide monosaccharides -simplest neutral glycosphingolipids Galactocerebroside ,which are most common in the neuronal cell membranes of the brain & have a Beta –D- galactose head group. Glucocerebroside - serves primarily as an intermediate in the synthesis and degradation of the more complex glycosphingolipids. cerebrosides are found predominantly in the brain and peripheral nervous tissue, with high concentrations in the myelin sheath
Globosides Globosides are glycosphingolipids with two or more sugars, usually D-glucose, D-galactose, or N-acetyl-D-galactosamine. Cerebrosides and globosides are sometimes called neutral glycolipids . As they have no charge at pH 7. Functions: It serves as an intermdiate in biosynthesis of gangliosides It is responsible for the anitgenicity of blood groups A and B .
Gangliosides are the most complex glycosphingolipids. They are ceramides with attached oligosaccharides that include at least one sialic acid residue. found primarily in the ganglion cells of the central nervous system, particularly at the nerve endings. Gangliosides
Gangliosides are primarily components of cell-surface membranes and constitute a significant fraction (6%) of brain lipids. Gangliosides have considerable physiological and medical significance. Their complex carbohydrate head groups, which extend beyond the surfaces of cell membranes, act as specific receptors for certain pituitary glycoprotein hormones that regulate a number of important physiological functions. Gangliosides are also receptors for certain bacterial protein toxins such as cholera toxin.
cerebrosides that contain sulfated galactosyl residues negatively charged at physiologic pH found predominantly in nerve tissue and kidney Sulfatides
Derived Lipids FATTY ACIDS Fatty acids are the main building blocks of fats including fats, phospholipids, glycolipids, cholesterol, waxes etc . These are the water insoluble long chain hydrocarbons . Fatty acids have a methyl group (CH3) at one end and a carboxyl group (COOH) at the other end with a chain of carbon and hydrogen atoms in the middle -are straight chain organic acids. -usually contain even number of carbon atoms -can be saturated (contain one bond) or unsaturated ( contain one or more double bonds ) About twenty fatty acids are found in foods and body tissues. The fatty acids have three important spects , chain length, saturation and essential fatty acids.
Length of Hydrocarbon Chain of Fatty Acids: Short chain fatty acids : 4 to 6 carbon atoms.Found in milk, fat, vinegar, and coconut Medium chain fatty acids : 8 to 12 carbon atoms. Long chain fatty acids: 14 to 18 carbon atoms. Found in most vegetable oils and animal fats Extra-long-chain fatty acids : More than 20 carbon atoms. Found in fish oils
CLASSIFICATION OF FATTY ACIDS Fatty Acids Fatty acids are classifieds according to the no. of carbon atoms & presence or absence of double bond. Mon o s a tu r at ed Fatty Acids Unsaturated Fatty Acids Polysaturated Fatty Acids Saturated Fatty Acids SATURATED FATTY ACIDS These are the fatty acids which contain only single bonds . Examples:- Palmitic acid , stearic acid etc.
Saturated fatty acid H as a single bond between its carbon atoms, thus the molecule is saturated with hydrogen . Stearic acid is an example of a saturated fatty acid . – triglyceride containing 3 saturated fatty acids , such as animal fats ( butter, lard) & tropical oils ( palm, coconut) 2. Appear solid at room temperature
Unsaturated fatty acids have one or more double bonds in their molecule and are thus not saturated with hydrogen. Further monounsaturated fatty acids (MUFA) have only one double bond in the molecules.
Polyunsaturated fat- triglycerides containing a high % of fatty acids with >2 double bonds; i.e. corn, safflower , soybean, sunflower oils and fish; 3 . Appear liquid at room temperature
Essential Fatty Acids Must be supplied by the diet Linoleic acid Linolenic acid Can be used to make other fatty acids Lipids: Chemistry and Nutritional Significance 5/16/2024 9:27 AM 64
Non-essential Fatty Acids From dietary point of view, saturated FAs are synthesized by human body , no need to provide as external source & not so essential as unsaturated FAs, so they are called non-essential fatty acids .
Fatty Acids Omega 3 , 6 and 9(PUFA) The methyl end of the fatty acid molecule is called the omega end. If the first double bond in the Fatty acid is in the third carbon atom from the methyl end, it is called omega-3 fatty acid ; They are also found in fatty fish and shellfish as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Salmon, anchovies, herring, sardines, Pacific oysters, trout, Atlantic mackerel, and Pacific mackerel are high in EPA and DHA and lower in mercury if it is in the sixth carbon from the methyl end, it is called omega-6- fatty acid and when it is in the ninth carbon, it is called omega-9 fatty acid. Copyright 2005 Wadsworth Group, a division of Thomson Learning
Copyright 2005 Wadsworth Group, a division of Thomson Learning Omega-3 and Omega-6 Fatty Acids Compared
Copyright 2005 Wadsworth Group, a division of Thomson Learning
Copyright 2005 Wadsworth Group, a division of Thomson Learning
Copyright 2005 Wadsworth Group, a division of Thomson Learning
Comparing Butter & Margarine Labels
Copyright 2005 Wadsworth Group, a division of Thomson Learning
FATTY ACIDS Hydrogenated – addition of hydrogen to unsaturated fat 1. Makes it more “solid” or firm 2. Effects stability and protects against oxidation; more “shelf- stable” 3. Widely used by food industry in margarine, shortening, peanut butter, baked goods & snack food
Copyright 2005 Wadsworth Group, a division of Thomson Learning Hydrogenation
Hydrogenation Cis vs. trans -fatty acids In nature, most double bonds are cis meaning that the hydrogens next to the double bonds are on the same side of the carbon chain When a fat is partially hydrogenated, some of the double bonds change from cis to trans
Copyright 2005 Wadsworth Group, a division of Thomson Learning Cis - and Trans -Fatty Acids Compared
Cholesterol - a steroidal alcohol (atherosclerosis!) High – red meat, egg yolks, dairy products Low – egg whites, yoghurt None ! – fruits, veggies, vegetable oils
Cholesterol is Absolutely Essential ! The average male (80kg/170lb) contains ~220gm About : 50% in cell membranes 40% converted to bile acids to ‘emulsify/ transport’ lipids (liver> gall bladder> intestines) some converted to hormones (testosterone, estrogens, cortisone) in 80kg male (~ gms ) blood 16 muscle 45 brain 50 adipose tissue 45 skin 18 liver 8 heart/kidney, etc. 8 adrenal glands 2 alimentary tract 7
Cell Membrane Structure (lipid bilayer)
Cholesterol Transport in vivo Cholesterol is insoluble in water, hence to transport it through the bloodstream, our bodies wrap it in a sheath of proteins and varying amounts of triglycerides to form lipoproteins. High Density Lipoproteins (HDL’s) transport excess cholesterol to the liver for disposal “good cholesterol” LDL’s (Low Density Lipoproteins) and VLDL’s tend to deposit cholesterol on arterial walls “bad cholesterol”
Structural features: HDL vs LDL HDL contains unsaturated cis Fatty acids LDL contains more saturated and trans fatty acids Both contain apolipoproteins and phospholipids which are oriented with hydrophobic part on inside and outer hydrophilic edges exposed
Cholesterol in gallstones Bile : used in fat digestion Contains water, cholesterol, bile salts , proteins and bilirubin (waste product) If bile contains too much cholesterol, it can harden into gallstones Extraction of cholesterol from gallstones (removed by surgery) is a common lab experiment! Size can range from grains of sand up to golf ball!
Source of bile acid Produced in liver Stored and concentrated in the gallbladder Secreted into small intestine If gallstone blocks exit duct, then gallbladder may need to be removed Fat digestion becomes more difficult, but not impossible
Gallstones
Health Effects of Saturated Fats, Trans Fats, and Cholesterol Lipids: Chemistry and Nutritional Significance Current American diet Excessive amounts of solid fats Blood lipid profile Heart disease Elevated LDL cholesterol a risk factor Saturated fats increase LDL cholesterol, promote blood clotting Dietary choices Trans fats – increase LDL cholesterol Dietary cholesterol 5/16/2024 9:27 AM 86
Fat Links to Cancer and Obesity Lipids: Chemistry and Nutritional Significance Cancer Dietary fat and cancer risk Differs for various types of cancer Promotion rather than initiation of cancer Obesity Cutting fat from diet reduces kcalories Dietary recommendations 5/16/2024 9:27 AM 87
Recommended Intakes of Saturated Fat, Trans Fat, and Cholesterol Lipids: Chemistry and Nutritional Significance DRI and Dietary Guidelines 20 to 35 percent of daily energy from fat Less than 10 percent of daily intake from saturated fat As little trans fat as possible Less than 300 mg cholesterol Avoid getting too little fat Recommendation: one teaspoon of fat with every meal 5/16/2024 9:27 AM 88
Health Effects of Monounsaturated and Polyunsaturated Fats Heart disease Replace saturated fats with unsaturated fats Regular consumption of omega- 3 fatty acids Suppresses inflammation Cancer Omega- 3 fatty acids from food Supplements Lipids: Chemistry and Nutritional Significance 5/16/2024 9:27 AM 89
Replacing Saturated Fat with Unsaturated Fat Lipids: Chemistry and Nutritional Significance Portion sizes have been adjusted so that each of these foods provides approximately 100 kcalories. Notice that for a similar number of kcalories and grams of fat, the second choices offer less saturated fat and more unsaturated fat. Replace these foods… Saturated Fat (g) Unsaturated Fat (g) Total Fat (g) Butter (1 tbs) 7 4 11 Bacon (2 slices) 3 6 9 Potato chips (10 chips) 2 5 7 Cheese (1 slice) 4 4 8 Steak (1'/2 0z) 2 3 5 Totals 18 22 40 …with these foods Saturated Fat (g) Unsaturated Fat (g) Total Fat (g) Olive oil (1 tbs) 2 9 11 Sunflower seeds (2 tbs) 1 7 8 Mixed nuts (2 tbs) 1 8 9 Avocado (6 slices) 2 8 10 Salmon (2 oz) 1 3 4 Totals 7 35 42 5/16/2024 9:27 AM 90
Recommended Intakes of Mono- and Polyunsaturated Fats Lipids: Chemistry and Nutritional Significance 20 to 35 percent of kcalories from fat Includes essential fatty acids AI have been established DRI Linoleic acid: 5-10% of daily energy Linolenic acid: 0.6- 1.2% of daily energy 5/16/2024 9:27 AM 91
Cutting Fat Cuts kCalories and Saturated Fat Lipids: Chemistry and Nutritional Significance 5/16/2024 9:27 AM 92
High- Fat Foods and Heart Health Lipids: Chemistry and Nutritional Significance Olive oil Benefits for heart health Replace saturated fats Nuts LDL cholesterol Fat composition Benefits for heart health Cautious advice for dietary inclusion 5/16/2024 9:27 AM 93
Fish Lipids: Chemistry and Nutritional Significance Omega- 3 fatty acids Benefits for heart health Environmental contaminants Farm raised versus wild Dietary recommendations 5/16/2024 9:27 AM 94
Two Meals Compared Lipids: Chemistry and Nutritional Significance 5/16/2024 9:27 AM 95