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Lipid Chemistry by Dr Anurag Yadav

The document discusses lipid chemistry, covering the definition, functions, classification, and significance of lipids in biological systems. It explains various types of lipids, such as simple lipids, complex lipids, and derived lipids, along with their roles in health and disease. Additionally, it highlights the clinical implications of lipids in conditions like obesity, cardiovascular diseases, and diabetes mellitus.

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LIPID CHEMISTRY MNR MEDICAL COLLEGE & HOSPITAL Dr Anurag Yadav MBBS, MD Assistant Professor Department of Biochemistry Instagram page –biochem365 Email: dranurag.y.m@gmail.com
Constituents of diet • Carbohydrates • Lipids • Proteins • Vitamins • Minerals • water
Lipid Chemistry • Why do we need to study lipid chemistry • Definition • Functions • classification
Give some examples for Lipids • Fats • Fatty acids • Cholesterol • Waxes • Phospholipids • Glycoproteins • Lipoproteins
What are Lipids? are a heterogeneous group of compounds, which are relatively insoluble in water and soluble in nonpolar solvents such as ether and chloroform. examples
Why do we need to study lipid chemistry
Clinical implication • Excessive fat deposits cause Obesity. • Truncal obesity is a risk factor for heart attack
Clinical implication • Abnormality in cholesterol and lipoprotein metabolism leads to the atherosclerosis and cardiovascular diseases.
Clinical implication • In diabetes mellitus, the metabolism of fatty acids and lipoproteins are deranged, leading to the ketosis.
Functions of Lipids 1) Structural components of cell membranes (phospholipids, cholesterol) 2) Storage form of energy (triglycerides).
3) Provides insulation against changes in external temperature. 4) Give shape and contour to the body. 5) Protect internal organs by providing a cushioning effect
6) Acts as surfactant, prevents lung collapse. 7) They act as metabolic regulators (Steroid hormones & Prostaglandinds- local hormones) 8) Helps in absorption of fat soluble vitamins in food.
9) Acts as electrical insulators – helps in propogation of nerve 10) Lipids gives taste and palatability to food.
Cell membrane Energy Insulation Shape Protects organs Surfactant Metabolic regulators Fat soluble vitamins Tasty food
Occurrence of Lipids? • Widely distributed in plants and animals. • Plants: nuts, seeds and oils • The Nervous system of Animals: cholesterol, phospholipids and glycolipids • Blood: contains lipoproteins 15
Occurrence of Lipids? • Fat depots (large amount of fats): – Subcutaneous tissues – Mesenteric tissues – Fatty tissues around the kidney – Yellow bone marrow • Food sources: – Milk, Egg, Meat, Liver – Fish oils, nuts, seeds and oils 16
Following diseases are associated with abnormal chemistry or metabolism of lipids- Obesity Atherosclerosis Diabetes Mellitus Hyperlipoproteinemia Fatty liver Lipid storage diseases Dr Anurag Yadav, 5/27/2021
Classification of Lipids Based on chemical composition classified into 3 groups. 1. Simple lipids: 2. Complex lipids: 3. Precursor and derived lipids:
Classification
CLASSIFICATION OF LIPIDS.
Classification of Lipids 1. Simple lipids: Esters of fatty acids with various alcohols. They don’t contain additional group. Simple lipids = FA + Alcohol 2. Complex lipids: Esters of fatty acids with alcohol and containing additional group. Complex lipids = FA + alcohol + Additional gp 3. Precursor and derived lipids: are derived from simple and complex lipids by their hydrolysis.
Examples for simple lipids • Fats • waxes
Examples for complex lipids • Phospholipids • Glycolipids • Sulfolipids • Lipoproteins etc.
Examples for Precursor and derived lipids • fatty acids, • glycerol and other alcohols, • Sterols and steroid hormones, • ketone bodies, • hydrocarbons, and • lipid-soluble vitamins.
1.Simple lipids • Esters of fatty acids with various alcohols. They don’t contain additional group. Simple lipids = FA + Alcohol Depending on type of alcohol present simple lipids are further classified into • a. Fats are esters of fatty acids with glycerol. Fats = FA + Glycerol • b. Waxes are esters of fatty acids with high molecular weight monohydric alcohol. FA + higher molecular monohydric alcohol
(a). FATS • Fats are esters of fatty acids with glycerol. Fats = FA + Glycerol Examples: Mono Acyl Glycerol = FA + Glycerol Di Acyl Glycerol = 2 FA + Glycerol Tri Acyl Glycerol = 3 FA + Glycerol
Tri acyl glycerol Glycerol 3 R-COOH 3 Fatty acids
Tri Acyl Glycerol There are 2 types based on type of FA present (i) simple Tri acyl glycerol (ii) mixed Tri acyl glycerol (i) simple Triglycerides: in which the three fatty acid radicals are of the same kind. Eg: Tristearin, triolein, tripalmitin, etc.
(ii) mixed Triglycerides in which the fatty acid radicals are of more than one kind. example, distearo-olein (two radicals of stearic and one of oleic acid), dioleo-palmitin ( two of oleic and one of palmitic), or stearo-oleo-palmitin (one radical each of stearic, oleic, and palmitic acids) etc.
Functions of Tri acyl glycerol 1. Major dietary constituent - high energy (calorific) value – 9kcal - natural fats provide essential fatty acids and fat soluble vitamins. 2. Major energy reserve of the body 3. Thermal insulator – Fats in the subcutaneous tissues and around certain organs. 4. Electrical insulator – Fats allow rapid propagation of depolarization waves along myelinated nerves.
b. Waxes • Esters of fatty acids with monohydric long chain alcohols. Waxes = FA + higher molecular monohydric alcohol Example cetyl palmitate (Palmitic acid + cetyl alcohol) myricyl palmitate (Palmitic acid +myricyl alcohol) In animals, waxes act as lubricants for skin and as a protective coating.
LIPIDS SIMPLE LIPIDS COMPLEX LIPIDS PRECURSOR AND DERIVED LIPIDS (FA + ALCOHOL) FATS WAXES (FA + GLYCEROL) (FA + HIGH MOL. WEIGHT ALCOHOL) MAG DAG TAG CETYL PALMITATE MYRICYL PALMITATE (FA + ALCOHOL+ ADD. GP) (HYDROLYTIC PRODUCT OF SIMPLE AND COMPLEX LIPIDS)
LIPIDS SIMPLE COMPOUND PHOSPHOLIPIDS NON-PHOSPHOLIPIDS DERIVED OTHERS
2. Complex lipids Complex lipids = FA + Alcohol + Additional gp Depending on the type of additional group present they are further classified into i. Phospholipids (phosphate as additional gp) ii. Glycolipids ( carbohydrate as additional gp) iii. Sulfolipids ( sulfate as additional gp) iv. Lipoprotein (lipids+proteins) are also included in this group.
Phospholipids • Phospholipids contain, in addition to fatty acids and an alcohol, a phosphoric acid residue. • They invariably carry a nitrogenous base (choline, ethanolamine, serine etc). PL = FA + Alcohol + Phosphoric acid+ NB Based on type of alcohol there are 2 types. i. Glycerophospholipids contain glycerol as alcohol ii. Sphingophospholipids (sphingomyelins) contain sphingosine as alcohol
PHOSPHO LIPIDS NITROGEN CONTAINING GLYCEROPHOSPHO LIPIDS LECITHIN CEPHALIN NON NITROGEN GLYCERPHOSPHO LIPIDS PHOSPHATIDYL INOSITOL PHOSPHATIDYL GLYCEROL DIPHOSPHATIDYL GLYCEROL PLASMALOGENS CHOLINE PLASMALOGEN ETHANOLAMINE PLASMALOGEN PHOSPHO SPHINOSIDES SPINGOMYELIN
Glycerophospholipids Glycero PL = 2FA + Glycerol + Phosphate + NB PHOSPHATIDIC ACID Examples (1) Phosphatidylcholine (Lecithin), (2) phosphatidylethanolamine (Cephalin), (3) phosphatidylserine, (4) phosphatidylinositol,and (5) Diphosphatidylglycerol (cardiolipin)
GLYCEROL + + + 2 FATTY ACID PHOSPHORIC ACID NITROGENOUS BASE PHOSPHATIDIC ACID -NITROGENOUS BASE CHOLINE + PHOSPHATIDIC ACID PHOSPHATIDIC ACID PHOSPHATIDIC ACID PHOSPHATIDIC ACID + + + + ETHANOLAMINE SERINE INOSITOL PHOSPHATIDYL GLYCEROL 1.PHOSPHATIDYLCHOLINE 2.PHOSPHATIDYLETHANOLAMINE 3. PHOSPHATIDYLSERINE 4.PHOSPHATIDYLINOSITOL = = = = = 5.DIPHOSPHATIDYL GLYCEROL (CARDIULIPIN) GLYCEROPHOSPHOLIPID EXAMPLES
Examples for glycerophosphplipids (contd) Lysophospholipids are glycerophospholipids containing only one fatty acid radical. Lyso PL = FA + Glycerol + Phosphate + NB lysophosphatidic acid eg, (6) Lysophosphatidylcholine (lysolecithin) (7) Lysophosphatidylethanolamine (lysolecithin)
GLYCEROL + + + FATTY ACID PHOSPHORIC ACID NITROGENOUS BASE LYSOPHOSPHATIDIC ACID --NITROGENOUS BASE HO
Examples for glycerophosphplipids (contd) • (9). Plasmalogens (Ether Glycerophospholipids) • resemble phosphatidylethanolamine but • possess an unsaturated alcohol on the -1 carbon by an ether link. • In some instances, choline, serine, or inositol may be substituted for ethanolamine. • Eg: platelet activating factor
GLYCEROL + + + FATTY ACID PHOSPHORIC ACID E PLASMALOGEN ETHANOLAMINE UNSATURATED ALCOHOL
ii. Sphingophospholipids (sphingomyelins) Are phospholipids containing sphingosine as alcohol. SphingoPL = Sphingosine+FA+Phosphate+choline ceramide
Functions of phospholipids 1. Main lipid constituents of plasma membrane. Phosphatidyl choline is the major PL of plasma membrane. • Phosphatidylethanolamine and phosphatidylserine are also found in cell membranes. • Amphipathic nature, has a hydrophilic head (phosphate + NB) and a long, hydrophobic tail (fatty acids or derivatives )
INTRA CELLULAR EXTRA CELLULAR PLASMA MEMBRANE 2 LAYERS OF PHOSPHOLIPIDS
Functions of phospholipids (contd) 2. Dipalmitoyl lecithin is a very effective surface-active agent ( surfactant). • It prevents adherenceof the inner surfaces of the lungs due to surface tension. • Its absence from the lungs of premature infants causes respiratory distress syndrome.
Functions of phospholipids (contd) 3. Phosphatidylserine plays a role in apoptosis (programmed cell death). 4. Phosphatidylinositol 4,5-bisphosphate (PIP2) helps in signal transduction. • It is present in cell membrane. • Upon stimulation by a hormone (oxitocin, TRH etc) , it is cleaved into diacylglycerol and inositol trisphosphate, both of which act as internal signals or second messengers.
5. Cardiolipin is a major lipid of mitochondrial membrane and is required for mitochondrial function. 6. Platelet activating factor (PAF – Plasmalogen) helps in aggregation of platelets. 7. Sphingomyelin is an important component of myeline sheath of nerve fibers.
COMPLEX LIPIDS PHOSPHOLIPIDS GLYCOLIPIDS LIPOPROTEINS (FA + ALCOHOL+ PHOS + NB) GLYCEROPL SPHINGOMYELINS (FA + GLYCEROL + PHOS + NB) (FA + SPHINGOSINE + PHOS + CHOLINE) PHOSPHATIDYLCHOLINE PHOSPHATIDYLETHANOLAMINE PHOSPHATIDYLSERINE AG DAG TAG LYSOPHOSPHATIDYLCHOLINE LYSOPHOSPHATIDYLETHANOLAMINE (FA + ALCOHOL+ CARBOH) (LPIDS + PROTEINS) PLATELET ACTIVATING FACTOR
NON PHOSPHORYLATED LIPIDS GLYCOLIPIDS CEREBROSIDES GLOBOSIDES GANGLIOSIDES SULPHOLIPIDS SULPHATED CEREBROSIDES GLOBOSIDES GANGLIOSIDES
ii. Glycolipids (Glycosphingolipids) • Are complex lipids containing carbohydrate as additional group. • Contain sphingosine, fattyacid and carbohydrate Glycolipids = Sphingosine+FA+Carbohydrate ceramide
• Depending on the type of carbohydrate present glycolipids are classified into 1. Cerebrosides (ceramide+ monosaccharide) 2. Sulfatides (ceramide+ sulfated galactose) 3. Globosides (ceramide+ oligosaccharide) 4. Gangliosides (ceramide+ oligosaccharide+ sialic acid)
1. Cerebroside are glycolipids containing monosaccharides (Glucose/Galactose) as carbohydrate group. Examples 1. Glucocerebroside (ceramide+ glucose) Found in the plasma membranes of cells in nonneural tissues. 2. Galactocerebroside (ceramide+ galactose) found in the plasma membranes of brain and other nervous tissue.
GLUCOCEREBROSIDE
GALACTOCEREBROSIDE
2. Sulfatides • Contain sulfated galactose as carbohydrate group. Sulfatides = ceramide+ sulfated galactose Present in high amounts in myelin sheath.
3.Globosides • are glycosphingolipids with two or more sugars (oligosaccharide). • usually contains D-glucose,D-galactose, or N- acetyl-D-galactosamine. Globosides = ceramide+ oligosaccharide
GLOBOSIDE
4. Gangliosides • have oligosaccharide and one or more residues of “sialic acid” (N-acetylneuraminic acid) as carbohydrate part. Gangliosides = ceramide+ oligosaccharide+ sialic acid. • D-glucose; D-galactose; N-acetyl-D-galactosamine; N-acetylneuraminic acid (sialic acid). Examples Monosialoganglioside (GM) Disialoganglioside (GD) Trisialoganglioside (GT)
GANGLIOSIDE (GM)
COMPLEX LIPIDS PHOSPHOLIPIDS GLYCOLIPIDS LIPOPROTEINS CEREBROSIDE GANGLIOSIDE (FA + SPHINGOSINE + MONOSACC) (FA + SPHINGOSINE + OLIGOSACC + SIALIC ACID) EG: GLUCOCEREBROSIDE GALACTOCEREBROSIDE (FA + SPHINGOSINE+ CARBOH) MONOSIALOGANGLIOSIDE DISIALOGANGLIOSIDE TRISIALOGANGLIOSIDE (FA + SPHINGOSINE + SULFATED GAL) (FA + SPHINGOSINE + OLIGOSACC) SULFATIDE GLOBOSIDE
Functions of Glycolipids • present in the outer leaflet of plasma membrane of every tissue of the body particularly in nervous tissue such as brain (cell surface carbohydrates). • where they act as points of recognition (receptor) for - extracellular molecules or - surfaces of neighbouring cells.
LIPIDS SIMPLE TAG WAX COMPOUND PHOSPHOLIPIDS NON-PHOSPHOLIPIDS DERIVED FATTY ACIDS STEROIDS PROSTAGLANDINS OTHERS LIPOPROTEINS
LIPOPROTEINS • Are Lipid Protein complexes. Lipoprotein = Lipids + Proteins • Lipid part is made up of • triacylglycerols , • phospholipids , • cholesterol , and • cholesteryl esters • The protein moiety of a lipoprotein is known as an apolipoprotein or apoprotein,
Lipoprotein = Lipids Proteins + triacylglycerols , phospholipids , cholesterol , and cholesteryl esters apolipoprotein Apo A, Apo B-48, Apo B-100 Apo CI,CII,CIII Apo D Apo E
LIPOPROTEIN MOLECULE
Classification of lipoproteins 2 types • (A) based on density : 4 Classes: (1) chylomicrons, <0.95 (2) very low density lipoproteins (VLDL), 0.95 – 1.006 (3) low-density lipoproteins (LDL) 1.006 – 1.063, and (4) high-density lipoproteins (HDL) 1.063 – 1.21
(B) Based on electrophoretic mobility: 4 classes 1. α lipoprotein (HDL) 2. β lipoprotein (LDL) 3. Preβ lipoprotein (VLDL) 4. Chylomicrons
DENSITY LIPID (MAJOR) APOLIPOPROTEIN CHYLOMICRONS <0.95 TAG Apo A, B-48, C,E VLDL 0.95 – 1.006 TAG Apo B-100, C,E LDL 1.006 – 1.063 CHOL, PL Apo B-100 HDL 1.063 – 1.21 CHOL, PL Apo A, C, D, E
Functions of lipoproteins (carriers of lipids in plasma) 1. Chylomicrons : transport dietary triacylglycerol from intestine to the extrahepatic tissues. 2. VLDL transports of endogenous triacylglycerol from liver to the extrahepatic tissues. 3. LDL transports cholesterol from liver to the extrahepatic tissues. 4. HDL transport cholesterol from the extrahepatic tissues to liver.
3. Precursors and derived lipids Are derived from simple and complex lipids by their hydrolysis. Other related compounds are also included in this group.
Examples for precursors and derived lipids • fatty acids, • glycerol and other alcohols, • Sterols and steroid hormones, • ketone bodies, • hydrocarbons, and • lipid-soluble vitamins
• Fatty acids - classification • Essential fatty acids and their functions • Eicosanoids and their functions • Cholesterol and its functions and reactions • Characteristics of fats
Fatty acids Are aliphatic carboxylic acids derived from hydrolysis of natural fats. General formula is R- COOH Where R is hydrocarbon chain
Examples (saturated FA) • Acetic ---------- 2 ------ CH3COOH • Propionic ----- 3 ------ CH3CH2COOH • Butyric -------- 4 ------- CH3(CH2)2COOH • Valeric --------- 5 ------- CH3(CH2)3COOH • Caproic -------- 6 ------- CH3(CH2)4COOH • Capric ----------10 ------- CH3(CH2)8COOH • Lauric ---------12 ------- CH3(CH2)10COOH • Myristic ------- 14 ------- CH3(CH2)12COOH • Palmitic ------- 16 • Stearic --------- 18
NUMBERING OF CARBON ATOMS
ω9
FATTY ACIDS - NOMENCLATURE Common name Systematic name Formula C2:0 Acetic acid Ethanoic acid CH3COOH C3:0 Propionic acid Propanoic acid CH3CH2COOH C4:0 Butyric acid Butanoic acid CH3(CH2)2COOH C14:0 Myristic acid Tetradecanoic acid CH3(CH2)12COOH C16:0 Palmitic acid Hexadecanoic acid CH3(CH2)14COOH C18:0 Stearic acid Octadecanoic acid CH3(CH2)16COOH C24:0 Lignoceric acid Tetracosanoic acid CH3(CH2)22COOH
UNSATURATED FATTY ACIDS - NOMENCLATURE Common name Formula C16:1(Δ9) ω7 Palmitoleic acid CH3(CH2)5CH=CH(CH2)7COOH C18:1(Δ9) ω9 Oleic acid CH3(CH2)7CH=CH(CH2)7COOH C18:2(Δ9,12) ω6 Linoleic acid CH3(CH2)4CH=CH CH2CH=CH(CH2)7COOH C18:3(Δ9,12,15) ω3 Linolenic acid CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH C20:4(Δ5,8,11,14) ω6 Arachidoni c acid CH3(CH2)4CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)3COOH C20:5(Δ5,5,11,14,17) ω3 Timnodoni c acid CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH 2)3COOH
Classification of fatty acids • Based on A. Total number of carbon atoms 1. Even chain (containing even number of C atom) Examples: acetic acid, butyric acid, palmitic acid stearic acid etc 1. Odd chain (containing even number of C atom) Examples: propionic acid, valeric acid etc
Classification of fatty acids (contd) B. Based on Chain length 1. Short chain (containing 2 to 6 C atoms) Examples: acetic acid, propionic acid, butyric acid, valeric acid etc. 2. Medium chain (containing 8 to 14 C atoms) Examples: capric acid, lauric acid, myristic acid etc 3. Long chain (containing 16 to 22 C atoms) Examples: palmitic stearic, arachidic,oleic acid etc. 4. Very long chain (containing more than 24 C atoms) Examples: nervonic acid, cerebronic acid etc
C. Depending on nature of hydrocarbon chain 4 types 1. saturated (containing no double bonds) FA. Examples: 2. unsaturated (containing one or more double bonds) FA. They are further classified into (a) Mono unsaturated fatty acids – contain one double bond. Examples: Classification of fatty acids (contd)
Classification of fatty acids(contd) (b) Poly unsaturated fatty acids(PUFA): contain two or more double bonds. Based on number of double bonds present they are divided into i. Dienoic fatty acids: contain two double bonds. Example: linoleic acid ii. Trienoic fatty acids: contain three double bonds. Example: linolenic acid iii. Tetraenoic fatty acids: contain four double bonds. Example: arachidonic acid. iv. Pentaenoic fatty acids: contain five double bonds. Example: timnodonic acid
Classification of fatty acids(contd) 3. Branched chain fatty acids Example: isovaleric acid, isobutyric acid, tuberculostearic acid etc. 4. Hydroxy fatty acids Example: cerebronic acid, ricinoleic acid etc.
Essential fatty acids (EFA) • Are fatty acids which cannot be synthesized by the body and have to be supplied in the diet. • They are • Linoleic acid • Linolenic acid • Arachidonic acid (can be synthesized from other EFA)
Functions of essential fatty acids (PUFA) 1. Arachidonic acid is the precursor of prostaglandins. 2. EFAs are constituents of phospholipids present in plasma membrane. 3. EFAs help to decrease plasma cholesterol level. 4. (Fatty acids are major source of energy). 5. Deficiency causes skin lesions (phrynoderma)
Cholesterol • Is a derived lipid. • Contains cyclopentanoperhydrophenanthrene ring. • Chemically known as 3- OH Δ5 cholestiene
Functions of cholesterol 1. It is an amphipathic molecule, constituent of plasma membrane and membranes of cellular organelles 2. Helps to maintain permeability and fluidity of plasma membrane 3. Required for the synthesis of 3 biologically important group of compounds (i). Steroid hormones: Aldosterone, cortisol, testosterone, estrogen, progesterone.
Functions of cholesterol (contd) (ii). Bile acids: cholic acid, chenodeoxy cholic acid – primary deoxy cholic acid, lithocholic acid – secondary (iii) vitamin D
Reactions of cholesterol 1. Esterification Cholesterol + fatty acid cholesteryl ester 2. Liebermann – Burchard reaction Chloroform solutions of Cholesterol when treated with concentrated sulfuric acid and acetic anhydride develop red, blue and green color due to the formation of sulfonic acid and cholestapolyenes.
EICOSANOIDS Are biologically important 20 C compounds formed from arachidonic acid. • Prostaglandins(PG) and prostacyclins (PGI) have the substituted cyclopentane ring at the centre , • thromboxanes (TX) have the cyclopentane ring interrupted with an oxygen atom (oxane ring), • leukotrienes (LT)and lipoxins (LX) (presence of three or four conjugated double bonds respectively) Physiologically, they are considered to act as local hormones
Prostaglandins Are 20 C unsaturated compounds carrying substituted cyclopentane ring. Types (based on substituted group): PGD, PGE, PGF,PGG, PGH Each class is further divided based on number of double bonds. Examples: PGD1,PGD2,PGD3
PGE2
Functions of eicosanoids • PGD2 is a potent sleep-promoting substance. • PGE and PGF stimulate uterine contraction. So, they are used to induce labor and to terminate pregnancy. • PGE is a vasodilator. • PGF is vasoconstrictor. • PGD and PGE are proinflammatory agents.
Functions of eicosanoids (contd) • Prostacyclins (PGI2 ) are potent inhibitors of platelet aggregation. • Thromboxanes cause vasoconstriction and platelet aggregation. • Leukotrienes cause bronchoconstriction and are potent proinflammatory agents
Characterization of fats 1. Saponification number 2. Iodine number 3. Reichter messl number 4. rancidity
• Saponification number: is defined as th mg of KOH required to saponify 1g of fat. • Each fatty acid residue in the fat uses one molecule of KOH for being saponified • It is inversely proportional to molecular weight of fatty acids present in the fat. • Example 1. Human fat --- 194-198 2. Butter ----------210 – 230 3. Coconut oil ----253 -262
TRI ACYL GLYCEROL + KOH GLYCEROL + 3R-COOK SOAP Saponification reaction (breakdown)
Riechert messel number (value) is defined as the number of ml of 0.1N NaOH necessary to neutralise the volatile water soluble fatty acids in 5g of fats. It is a measure of water soluble volatile fatty acids present in the fat.
Iodine number: is defined as number of g of iodine taken up by 100g of fat. Iodine is absorbed only at the double bonds of unsaturated fatty acid residues of fats. It is directly proportional to the degree of unsaturation of fatty acids present in the fat. Example: Butter ------------- 28 Sunflower oil --- 130
Rancidity: Objectionable taste and odour of fat on standing exposed to light, moisture and air. Rancidity results from 1. Formation of aldehydes and peroxides due to oxidation of unsaturated fatty acids – Oxidative rancidity. 2. Microbial decomposition of free fatty acids (produced by the action of lipases) to ketones – Hydrolytic rancidity.
Dr Anurag Yadav MBBS, MD Assistant Professor Department of Biochemistry Instagram page –biochem365 Email: dranurag.y.m@gmail.com

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Lipid Chemistry by Dr Anurag Yadav

  • 1.
    LIPID CHEMISTRY MNR MEDICALCOLLEGE & HOSPITAL Dr Anurag Yadav MBBS, MD Assistant Professor Department of Biochemistry Instagram page –biochem365 Email: dranurag.y.m@gmail.com
  • 2.
    Constituents of diet •Carbohydrates • Lipids • Proteins • Vitamins • Minerals • water
  • 3.
    Lipid Chemistry • Whydo we need to study lipid chemistry • Definition • Functions • classification
  • 4.
    Give some examplesfor Lipids • Fats • Fatty acids • Cholesterol • Waxes • Phospholipids • Glycoproteins • Lipoproteins
  • 5.
    What are Lipids? area heterogeneous group of compounds, which are relatively insoluble in water and soluble in nonpolar solvents such as ether and chloroform. examples
  • 6.
    Why do weneed to study lipid chemistry
  • 7.
    Clinical implication • Excessivefat deposits cause Obesity. • Truncal obesity is a risk factor for heart attack
  • 8.
    Clinical implication • Abnormalityin cholesterol and lipoprotein metabolism leads to the atherosclerosis and cardiovascular diseases.
  • 9.
    Clinical implication • Indiabetes mellitus, the metabolism of fatty acids and lipoproteins are deranged, leading to the ketosis.
  • 10.
    Functions of Lipids 1)Structural components of cell membranes (phospholipids, cholesterol) 2) Storage form of energy (triglycerides).
  • 11.
    3) Provides insulationagainst changes in external temperature. 4) Give shape and contour to the body. 5) Protect internal organs by providing a cushioning effect
  • 12.
    6) Acts assurfactant, prevents lung collapse. 7) They act as metabolic regulators (Steroid hormones & Prostaglandinds- local hormones) 8) Helps in absorption of fat soluble vitamins in food.
  • 13.
    9) Acts aselectrical insulators – helps in propogation of nerve 10) Lipids gives taste and palatability to food.
  • 14.
  • 15.
    Occurrence of Lipids? •Widely distributed in plants and animals. • Plants: nuts, seeds and oils • The Nervous system of Animals: cholesterol, phospholipids and glycolipids • Blood: contains lipoproteins 15
  • 16.
    Occurrence of Lipids? •Fat depots (large amount of fats): – Subcutaneous tissues – Mesenteric tissues – Fatty tissues around the kidney – Yellow bone marrow • Food sources: – Milk, Egg, Meat, Liver – Fish oils, nuts, seeds and oils 16
  • 17.
    Following diseases areassociated with abnormal chemistry or metabolism of lipids- Obesity Atherosclerosis Diabetes Mellitus Hyperlipoproteinemia Fatty liver Lipid storage diseases Dr Anurag Yadav, 5/27/2021
  • 18.
    Classification of Lipids Basedon chemical composition classified into 3 groups. 1. Simple lipids: 2. Complex lipids: 3. Precursor and derived lipids:
  • 19.
  • 20.
  • 21.
    Classification of Lipids 1.Simple lipids: Esters of fatty acids with various alcohols. They don’t contain additional group. Simple lipids = FA + Alcohol 2. Complex lipids: Esters of fatty acids with alcohol and containing additional group. Complex lipids = FA + alcohol + Additional gp 3. Precursor and derived lipids: are derived from simple and complex lipids by their hydrolysis.
  • 22.
    Examples for simplelipids • Fats • waxes
  • 23.
    Examples for complexlipids • Phospholipids • Glycolipids • Sulfolipids • Lipoproteins etc.
  • 24.
    Examples for Precursorand derived lipids • fatty acids, • glycerol and other alcohols, • Sterols and steroid hormones, • ketone bodies, • hydrocarbons, and • lipid-soluble vitamins.
  • 26.
    1.Simple lipids • Estersof fatty acids with various alcohols. They don’t contain additional group. Simple lipids = FA + Alcohol Depending on type of alcohol present simple lipids are further classified into • a. Fats are esters of fatty acids with glycerol. Fats = FA + Glycerol • b. Waxes are esters of fatty acids with high molecular weight monohydric alcohol. FA + higher molecular monohydric alcohol
  • 27.
    (a). FATS • Fatsare esters of fatty acids with glycerol. Fats = FA + Glycerol Examples: Mono Acyl Glycerol = FA + Glycerol Di Acyl Glycerol = 2 FA + Glycerol Tri Acyl Glycerol = 3 FA + Glycerol
  • 28.
    Tri acyl glycerol Glycerol 3R-COOH 3 Fatty acids
  • 30.
    Tri Acyl Glycerol Thereare 2 types based on type of FA present (i) simple Tri acyl glycerol (ii) mixed Tri acyl glycerol (i) simple Triglycerides: in which the three fatty acid radicals are of the same kind. Eg: Tristearin, triolein, tripalmitin, etc.
  • 31.
    (ii) mixed Triglyceridesin which the fatty acid radicals are of more than one kind. example, distearo-olein (two radicals of stearic and one of oleic acid), dioleo-palmitin ( two of oleic and one of palmitic), or stearo-oleo-palmitin (one radical each of stearic, oleic, and palmitic acids) etc.
  • 32.
    Functions of Triacyl glycerol 1. Major dietary constituent - high energy (calorific) value – 9kcal - natural fats provide essential fatty acids and fat soluble vitamins. 2. Major energy reserve of the body 3. Thermal insulator – Fats in the subcutaneous tissues and around certain organs. 4. Electrical insulator – Fats allow rapid propagation of depolarization waves along myelinated nerves.
  • 33.
    b. Waxes • Estersof fatty acids with monohydric long chain alcohols. Waxes = FA + higher molecular monohydric alcohol Example cetyl palmitate (Palmitic acid + cetyl alcohol) myricyl palmitate (Palmitic acid +myricyl alcohol) In animals, waxes act as lubricants for skin and as a protective coating.
  • 34.
    LIPIDS SIMPLE LIPIDS COMPLEX LIPIDS PRECURSOR AND DERIVED LIPIDS (FA+ ALCOHOL) FATS WAXES (FA + GLYCEROL) (FA + HIGH MOL. WEIGHT ALCOHOL) MAG DAG TAG CETYL PALMITATE MYRICYL PALMITATE (FA + ALCOHOL+ ADD. GP) (HYDROLYTIC PRODUCT OF SIMPLE AND COMPLEX LIPIDS)
  • 35.
  • 36.
    2. Complex lipids Complexlipids = FA + Alcohol + Additional gp Depending on the type of additional group present they are further classified into i. Phospholipids (phosphate as additional gp) ii. Glycolipids ( carbohydrate as additional gp) iii. Sulfolipids ( sulfate as additional gp) iv. Lipoprotein (lipids+proteins) are also included in this group.
  • 37.
    Phospholipids • Phospholipids contain,in addition to fatty acids and an alcohol, a phosphoric acid residue. • They invariably carry a nitrogenous base (choline, ethanolamine, serine etc). PL = FA + Alcohol + Phosphoric acid+ NB Based on type of alcohol there are 2 types. i. Glycerophospholipids contain glycerol as alcohol ii. Sphingophospholipids (sphingomyelins) contain sphingosine as alcohol
  • 39.
    PHOSPHO LIPIDS NITROGEN CONTAINING GLYCEROPHOSPHO LIPIDS LECITHIN CEPHALIN NON NITROGEN GLYCERPHOSPHO LIPIDS PHOSPHATIDYL INOSITOL PHOSPHATIDYLGLYCEROL DIPHOSPHATIDYL GLYCEROL PLASMALOGENS CHOLINE PLASMALOGEN ETHANOLAMINE PLASMALOGEN PHOSPHO SPHINOSIDES SPINGOMYELIN
  • 40.
    Glycerophospholipids Glycero PL =2FA + Glycerol + Phosphate + NB PHOSPHATIDIC ACID Examples (1) Phosphatidylcholine (Lecithin), (2) phosphatidylethanolamine (Cephalin), (3) phosphatidylserine, (4) phosphatidylinositol,and (5) Diphosphatidylglycerol (cardiolipin)
  • 41.
    GLYCEROL + ++ 2 FATTY ACID PHOSPHORIC ACID NITROGENOUS BASE PHOSPHATIDIC ACID -NITROGENOUS BASE CHOLINE + PHOSPHATIDIC ACID PHOSPHATIDIC ACID PHOSPHATIDIC ACID PHOSPHATIDIC ACID + + + + ETHANOLAMINE SERINE INOSITOL PHOSPHATIDYL GLYCEROL 1.PHOSPHATIDYLCHOLINE 2.PHOSPHATIDYLETHANOLAMINE 3. PHOSPHATIDYLSERINE 4.PHOSPHATIDYLINOSITOL = = = = = 5.DIPHOSPHATIDYL GLYCEROL (CARDIULIPIN) GLYCEROPHOSPHOLIPID EXAMPLES
  • 42.
    Examples for glycerophosphplipids (contd) Lysophospholipidsare glycerophospholipids containing only one fatty acid radical. Lyso PL = FA + Glycerol + Phosphate + NB lysophosphatidic acid eg, (6) Lysophosphatidylcholine (lysolecithin) (7) Lysophosphatidylethanolamine (lysolecithin)
  • 43.
    GLYCEROL + ++ FATTY ACID PHOSPHORIC ACID NITROGENOUS BASE LYSOPHOSPHATIDIC ACID --NITROGENOUS BASE HO
  • 44.
    Examples for glycerophosphplipids (contd) •(9). Plasmalogens (Ether Glycerophospholipids) • resemble phosphatidylethanolamine but • possess an unsaturated alcohol on the -1 carbon by an ether link. • In some instances, choline, serine, or inositol may be substituted for ethanolamine. • Eg: platelet activating factor
  • 45.
    GLYCEROL + ++ FATTY ACID PHOSPHORIC ACID E PLASMALOGEN ETHANOLAMINE UNSATURATED ALCOHOL
  • 46.
    ii. Sphingophospholipids (sphingomyelins) Are phospholipidscontaining sphingosine as alcohol. SphingoPL = Sphingosine+FA+Phosphate+choline ceramide
  • 49.
    Functions of phospholipids 1.Main lipid constituents of plasma membrane. Phosphatidyl choline is the major PL of plasma membrane. • Phosphatidylethanolamine and phosphatidylserine are also found in cell membranes. • Amphipathic nature, has a hydrophilic head (phosphate + NB) and a long, hydrophobic tail (fatty acids or derivatives )
  • 50.
    INTRA CELLULAR EXTRACELLULAR PLASMA MEMBRANE 2 LAYERS OF PHOSPHOLIPIDS
  • 51.
    Functions of phospholipids(contd) 2. Dipalmitoyl lecithin is a very effective surface-active agent ( surfactant). • It prevents adherenceof the inner surfaces of the lungs due to surface tension. • Its absence from the lungs of premature infants causes respiratory distress syndrome.
  • 52.
    Functions of phospholipids(contd) 3. Phosphatidylserine plays a role in apoptosis (programmed cell death). 4. Phosphatidylinositol 4,5-bisphosphate (PIP2) helps in signal transduction. • It is present in cell membrane. • Upon stimulation by a hormone (oxitocin, TRH etc) , it is cleaved into diacylglycerol and inositol trisphosphate, both of which act as internal signals or second messengers.
  • 53.
    5. Cardiolipin isa major lipid of mitochondrial membrane and is required for mitochondrial function. 6. Platelet activating factor (PAF – Plasmalogen) helps in aggregation of platelets. 7. Sphingomyelin is an important component of myeline sheath of nerve fibers.
  • 54.
    COMPLEX LIPIDS PHOSPHOLIPIDS GLYCOLIPIDSLIPOPROTEINS (FA + ALCOHOL+ PHOS + NB) GLYCEROPL SPHINGOMYELINS (FA + GLYCEROL + PHOS + NB) (FA + SPHINGOSINE + PHOS + CHOLINE) PHOSPHATIDYLCHOLINE PHOSPHATIDYLETHANOLAMINE PHOSPHATIDYLSERINE AG DAG TAG LYSOPHOSPHATIDYLCHOLINE LYSOPHOSPHATIDYLETHANOLAMINE (FA + ALCOHOL+ CARBOH) (LPIDS + PROTEINS) PLATELET ACTIVATING FACTOR
  • 55.
  • 56.
    ii. Glycolipids (Glycosphingolipids) •Are complex lipids containing carbohydrate as additional group. • Contain sphingosine, fattyacid and carbohydrate Glycolipids = Sphingosine+FA+Carbohydrate ceramide
  • 59.
    • Depending onthe type of carbohydrate present glycolipids are classified into 1. Cerebrosides (ceramide+ monosaccharide) 2. Sulfatides (ceramide+ sulfated galactose) 3. Globosides (ceramide+ oligosaccharide) 4. Gangliosides (ceramide+ oligosaccharide+ sialic acid)
  • 60.
    1. Cerebroside are glycolipidscontaining monosaccharides (Glucose/Galactose) as carbohydrate group. Examples 1. Glucocerebroside (ceramide+ glucose) Found in the plasma membranes of cells in nonneural tissues. 2. Galactocerebroside (ceramide+ galactose) found in the plasma membranes of brain and other nervous tissue.
  • 61.
  • 62.
  • 63.
    2. Sulfatides • Containsulfated galactose as carbohydrate group. Sulfatides = ceramide+ sulfated galactose Present in high amounts in myelin sheath.
  • 65.
    3.Globosides • are glycosphingolipidswith two or more sugars (oligosaccharide). • usually contains D-glucose,D-galactose, or N- acetyl-D-galactosamine. Globosides = ceramide+ oligosaccharide
  • 66.
  • 67.
    4. Gangliosides • haveoligosaccharide and one or more residues of “sialic acid” (N-acetylneuraminic acid) as carbohydrate part. Gangliosides = ceramide+ oligosaccharide+ sialic acid. • D-glucose; D-galactose; N-acetyl-D-galactosamine; N-acetylneuraminic acid (sialic acid). Examples Monosialoganglioside (GM) Disialoganglioside (GD) Trisialoganglioside (GT)
  • 69.
  • 70.
    COMPLEX LIPIDS PHOSPHOLIPIDS GLYCOLIPIDSLIPOPROTEINS CEREBROSIDE GANGLIOSIDE (FA + SPHINGOSINE + MONOSACC) (FA + SPHINGOSINE + OLIGOSACC + SIALIC ACID) EG: GLUCOCEREBROSIDE GALACTOCEREBROSIDE (FA + SPHINGOSINE+ CARBOH) MONOSIALOGANGLIOSIDE DISIALOGANGLIOSIDE TRISIALOGANGLIOSIDE (FA + SPHINGOSINE + SULFATED GAL) (FA + SPHINGOSINE + OLIGOSACC) SULFATIDE GLOBOSIDE
  • 71.
    Functions of Glycolipids •present in the outer leaflet of plasma membrane of every tissue of the body particularly in nervous tissue such as brain (cell surface carbohydrates). • where they act as points of recognition (receptor) for - extracellular molecules or - surfaces of neighbouring cells.
  • 72.
  • 74.
    LIPOPROTEINS • Are LipidProtein complexes. Lipoprotein = Lipids + Proteins • Lipid part is made up of • triacylglycerols , • phospholipids , • cholesterol , and • cholesteryl esters • The protein moiety of a lipoprotein is known as an apolipoprotein or apoprotein,
  • 75.
    Lipoprotein = LipidsProteins + triacylglycerols , phospholipids , cholesterol , and cholesteryl esters apolipoprotein Apo A, Apo B-48, Apo B-100 Apo CI,CII,CIII Apo D Apo E
  • 76.
  • 77.
    Classification of lipoproteins 2types • (A) based on density : 4 Classes: (1) chylomicrons, <0.95 (2) very low density lipoproteins (VLDL), 0.95 – 1.006 (3) low-density lipoproteins (LDL) 1.006 – 1.063, and (4) high-density lipoproteins (HDL) 1.063 – 1.21
  • 78.
    (B) Based onelectrophoretic mobility: 4 classes 1. α lipoprotein (HDL) 2. β lipoprotein (LDL) 3. Preβ lipoprotein (VLDL) 4. Chylomicrons
  • 79.
    DENSITY LIPID (MAJOR)APOLIPOPROTEIN CHYLOMICRONS <0.95 TAG Apo A, B-48, C,E VLDL 0.95 – 1.006 TAG Apo B-100, C,E LDL 1.006 – 1.063 CHOL, PL Apo B-100 HDL 1.063 – 1.21 CHOL, PL Apo A, C, D, E
  • 80.
    Functions of lipoproteins (carriersof lipids in plasma) 1. Chylomicrons : transport dietary triacylglycerol from intestine to the extrahepatic tissues. 2. VLDL transports of endogenous triacylglycerol from liver to the extrahepatic tissues. 3. LDL transports cholesterol from liver to the extrahepatic tissues. 4. HDL transport cholesterol from the extrahepatic tissues to liver.
  • 81.
    3. Precursors andderived lipids Are derived from simple and complex lipids by their hydrolysis. Other related compounds are also included in this group.
  • 82.
    Examples for precursorsand derived lipids • fatty acids, • glycerol and other alcohols, • Sterols and steroid hormones, • ketone bodies, • hydrocarbons, and • lipid-soluble vitamins
  • 83.
    • Fatty acids- classification • Essential fatty acids and their functions • Eicosanoids and their functions • Cholesterol and its functions and reactions • Characteristics of fats
  • 84.
    Fatty acids Are aliphaticcarboxylic acids derived from hydrolysis of natural fats. General formula is R- COOH Where R is hydrocarbon chain
  • 85.
    Examples (saturated FA) •Acetic ---------- 2 ------ CH3COOH • Propionic ----- 3 ------ CH3CH2COOH • Butyric -------- 4 ------- CH3(CH2)2COOH • Valeric --------- 5 ------- CH3(CH2)3COOH • Caproic -------- 6 ------- CH3(CH2)4COOH • Capric ----------10 ------- CH3(CH2)8COOH • Lauric ---------12 ------- CH3(CH2)10COOH • Myristic ------- 14 ------- CH3(CH2)12COOH • Palmitic ------- 16 • Stearic --------- 18
  • 86.
  • 87.
  • 88.
    FATTY ACIDS -NOMENCLATURE Common name Systematic name Formula C2:0 Acetic acid Ethanoic acid CH3COOH C3:0 Propionic acid Propanoic acid CH3CH2COOH C4:0 Butyric acid Butanoic acid CH3(CH2)2COOH C14:0 Myristic acid Tetradecanoic acid CH3(CH2)12COOH C16:0 Palmitic acid Hexadecanoic acid CH3(CH2)14COOH C18:0 Stearic acid Octadecanoic acid CH3(CH2)16COOH C24:0 Lignoceric acid Tetracosanoic acid CH3(CH2)22COOH
  • 89.
    UNSATURATED FATTY ACIDS- NOMENCLATURE Common name Formula C16:1(Δ9) ω7 Palmitoleic acid CH3(CH2)5CH=CH(CH2)7COOH C18:1(Δ9) ω9 Oleic acid CH3(CH2)7CH=CH(CH2)7COOH C18:2(Δ9,12) ω6 Linoleic acid CH3(CH2)4CH=CH CH2CH=CH(CH2)7COOH C18:3(Δ9,12,15) ω3 Linolenic acid CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH C20:4(Δ5,8,11,14) ω6 Arachidoni c acid CH3(CH2)4CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)3COOH C20:5(Δ5,5,11,14,17) ω3 Timnodoni c acid CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH 2)3COOH
  • 90.
    Classification of fattyacids • Based on A. Total number of carbon atoms 1. Even chain (containing even number of C atom) Examples: acetic acid, butyric acid, palmitic acid stearic acid etc 1. Odd chain (containing even number of C atom) Examples: propionic acid, valeric acid etc
  • 91.
    Classification of fattyacids (contd) B. Based on Chain length 1. Short chain (containing 2 to 6 C atoms) Examples: acetic acid, propionic acid, butyric acid, valeric acid etc. 2. Medium chain (containing 8 to 14 C atoms) Examples: capric acid, lauric acid, myristic acid etc 3. Long chain (containing 16 to 22 C atoms) Examples: palmitic stearic, arachidic,oleic acid etc. 4. Very long chain (containing more than 24 C atoms) Examples: nervonic acid, cerebronic acid etc
  • 92.
    C. Depending onnature of hydrocarbon chain 4 types 1. saturated (containing no double bonds) FA. Examples: 2. unsaturated (containing one or more double bonds) FA. They are further classified into (a) Mono unsaturated fatty acids – contain one double bond. Examples: Classification of fatty acids (contd)
  • 93.
    Classification of fattyacids(contd) (b) Poly unsaturated fatty acids(PUFA): contain two or more double bonds. Based on number of double bonds present they are divided into i. Dienoic fatty acids: contain two double bonds. Example: linoleic acid ii. Trienoic fatty acids: contain three double bonds. Example: linolenic acid iii. Tetraenoic fatty acids: contain four double bonds. Example: arachidonic acid. iv. Pentaenoic fatty acids: contain five double bonds. Example: timnodonic acid
  • 94.
    Classification of fattyacids(contd) 3. Branched chain fatty acids Example: isovaleric acid, isobutyric acid, tuberculostearic acid etc. 4. Hydroxy fatty acids Example: cerebronic acid, ricinoleic acid etc.
  • 95.
    Essential fatty acids(EFA) • Are fatty acids which cannot be synthesized by the body and have to be supplied in the diet. • They are • Linoleic acid • Linolenic acid • Arachidonic acid (can be synthesized from other EFA)
  • 96.
    Functions of essentialfatty acids (PUFA) 1. Arachidonic acid is the precursor of prostaglandins. 2. EFAs are constituents of phospholipids present in plasma membrane. 3. EFAs help to decrease plasma cholesterol level. 4. (Fatty acids are major source of energy). 5. Deficiency causes skin lesions (phrynoderma)
  • 97.
    Cholesterol • Is aderived lipid. • Contains cyclopentanoperhydrophenanthrene ring. • Chemically known as 3- OH Δ5 cholestiene
  • 99.
    Functions of cholesterol 1.It is an amphipathic molecule, constituent of plasma membrane and membranes of cellular organelles 2. Helps to maintain permeability and fluidity of plasma membrane 3. Required for the synthesis of 3 biologically important group of compounds (i). Steroid hormones: Aldosterone, cortisol, testosterone, estrogen, progesterone.
  • 100.
    Functions of cholesterol(contd) (ii). Bile acids: cholic acid, chenodeoxy cholic acid – primary deoxy cholic acid, lithocholic acid – secondary (iii) vitamin D
  • 101.
    Reactions of cholesterol 1.Esterification Cholesterol + fatty acid cholesteryl ester 2. Liebermann – Burchard reaction Chloroform solutions of Cholesterol when treated with concentrated sulfuric acid and acetic anhydride develop red, blue and green color due to the formation of sulfonic acid and cholestapolyenes.
  • 102.
    EICOSANOIDS Are biologically important20 C compounds formed from arachidonic acid. • Prostaglandins(PG) and prostacyclins (PGI) have the substituted cyclopentane ring at the centre , • thromboxanes (TX) have the cyclopentane ring interrupted with an oxygen atom (oxane ring), • leukotrienes (LT)and lipoxins (LX) (presence of three or four conjugated double bonds respectively) Physiologically, they are considered to act as local hormones
  • 103.
    Prostaglandins Are 20 Cunsaturated compounds carrying substituted cyclopentane ring. Types (based on substituted group): PGD, PGE, PGF,PGG, PGH Each class is further divided based on number of double bonds. Examples: PGD1,PGD2,PGD3
  • 104.
  • 105.
    Functions of eicosanoids •PGD2 is a potent sleep-promoting substance. • PGE and PGF stimulate uterine contraction. So, they are used to induce labor and to terminate pregnancy. • PGE is a vasodilator. • PGF is vasoconstrictor. • PGD and PGE are proinflammatory agents.
  • 106.
    Functions of eicosanoids(contd) • Prostacyclins (PGI2 ) are potent inhibitors of platelet aggregation. • Thromboxanes cause vasoconstriction and platelet aggregation. • Leukotrienes cause bronchoconstriction and are potent proinflammatory agents
  • 107.
    Characterization of fats 1.Saponification number 2. Iodine number 3. Reichter messl number 4. rancidity
  • 108.
    • Saponification number:is defined as th mg of KOH required to saponify 1g of fat. • Each fatty acid residue in the fat uses one molecule of KOH for being saponified • It is inversely proportional to molecular weight of fatty acids present in the fat. • Example 1. Human fat --- 194-198 2. Butter ----------210 – 230 3. Coconut oil ----253 -262
  • 109.
    TRI ACYL GLYCEROL +KOH GLYCEROL + 3R-COOK SOAP Saponification reaction (breakdown)
  • 110.
    Riechert messel number(value) is defined as the number of ml of 0.1N NaOH necessary to neutralise the volatile water soluble fatty acids in 5g of fats. It is a measure of water soluble volatile fatty acids present in the fat.
  • 111.
    Iodine number: isdefined as number of g of iodine taken up by 100g of fat. Iodine is absorbed only at the double bonds of unsaturated fatty acid residues of fats. It is directly proportional to the degree of unsaturation of fatty acids present in the fat. Example: Butter ------------- 28 Sunflower oil --- 130
  • 112.
    Rancidity: Objectionable taste andodour of fat on standing exposed to light, moisture and air. Rancidity results from 1. Formation of aldehydes and peroxides due to oxidation of unsaturated fatty acids – Oxidative rancidity. 2. Microbial decomposition of free fatty acids (produced by the action of lipases) to ketones – Hydrolytic rancidity.
  • 113.
    Dr Anurag Yadav MBBS,MD Assistant Professor Department of Biochemistry Instagram page –biochem365 Email: dranurag.y.m@gmail.com