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OUTLINE
INTRODUCTION TO LIPIDS
consists of fixed oils, fats, and waxes esters of long chain fatty acids and alcohols, or of closely related derivatives fats and fixed oils are obtained for either plants (olive oil, peanut oil) or animals (lard) Their primary function is food (energy) storage Fixed oils and fats differs only as to melting point Acts as fuel in the body caloric value: 9 Kcals/gm Deposits of fats underneath the skin = exert insulation effects The mesenteric fat around organs (kidney) = padding and protecting internal organs Building materials (cholesterol -> hormone synthesis
LIPIDS LIPIDS
MID^22 PHARMACOGNOSY AND PLANT CHEMISTRY LEC
Introduction to Lipids Biosynthesis Importance Tests of Lipids Methods of Extraction Classes of Lipids based on their ability to absorb oxygen Classification of Fixed oils
- Saturated
- Monounsaturated
- Polyunsaturated Fats Fatty acids Waxed Prostaglandins BIOLOGICAL SIGNIFICANCE OF FATS
LIPIDS
Generally semi-solid or solid at ordinary temperature. Exception: Cod liver oil, which remains liquid. Typically liquid at normal room temperature. Exception: Cocoa butter, which is solid. Fatty or Fixed Oils: Fats
LIPIDS BIOSYNTHESIS
liquid except theobroma cacao
LIPIDS LIPIDS
MID^22 PHARMACOGNOSY AND PLANT CHEMISTRY LEC
emollient vehicle for IM injection cathartic soap production energy
USES OF LIPIDS
FATS FIXED OIL WAX
fatty acid + glycerol fatty acid + glycerol fatty acid + high molecular weight monohydric alcohol solid except cod liver oil solid, semi-solid animals (^) plants both saturated unsaturated both energy storage energy storage protection enzyme: malonyl CoA
Common name Systematic name Formula Common source Oleic Cis 9-octadecenoic C17H33COOH plant and animal fats Elaidic Trans 9-Octadecenoic C17H33COOH animal fats
TANNINS TANNINS
MID^22 PHARMACOGNOSY AND PLANT CHEMISTRY LEC
UNSATURATED FATTY ACIDS
3-octanoic acid 3,6-octanoic acid 8:2 (∆ 3,6)
CLASSIFICATION OF FATTY ACIDS PRESENT AS GLYCERIDES IN FOOD FATS
Omega 9 Omega 6 A. Monoethenoic Acids Common name Systematic name Formula Common source Linoleic 9,12-Octadecadienoic C17H31COOH peanut, linseed, and cottonseed oils B. Diethenoic Acids Common name Systematic name Formula Common source Linolenic 9,12,15-Octadecatrienoic C17H29COOH linseed and other seed oils Eleostearic 9,11,13-Octadecatrienoic C17H29COOH peanut seed fats C. Triethenoid Acids Omega 3 Common name Systematic name Formula Common source Moroctic 4,8,12,15-Octadecatetraenoic^ C17H27COOH fish oils Arachidoic 5,8,11,14-Eicosatetraenoic C19H31COOH traces in animal fats D. Tetraethenoid Acids
IMPORTANCE OF LIPIDS
PROPERTIES OF LIPIDS
LIPIDS LIPIDS
MID^22 PHARMACOGNOSY AND PLANT CHEMISTRY LEC
Polyunsaturated Fatty Acid Two or more double bonds Members EFA Essential Fatty Acid
- Linolenic acid (Omega 3 FA) : FISH
- Linoleic acid (Omega 6 FA) : PLANTS Richest source of PUFA:
- Vegetable oils (Corn, sunflower, cottonseed oils) Omega 6
PUFA
EFA - OMEGA 3 AND 6 FATS
Omega: position of the 1st double bond from the methyl group Omega 3 FA: first point of unsaturation - 3rd carbon Omega 6 FA: first point of unsaturation- 6th carbon great significance on human nutrition and health issues Omega 3: heart, brain, metabolism Omega 6: energy energy storage signaling molecule structural component of cell membrane Physical greasy lighter than water insoluble in water soluble in inorganic solvents Chemical non polar, hydrophobic HYDROLYSIS - triglycerides yield glycerol and fatty acids ESTERIFICATION - glycerol + 3 fatty acids = triglycerides RANCIDITY
- initial products of oxidation: . aldehydes and ketones
- final products of oxidation: . acid (RCOOH)
CLASSIFICATION OF FIXED OILS
expression or extraction from the seed kernels of the coconut palm Scientific name: Cocos nucifera Family: Arecaceae Coconut oil yields quality soaps and shampoos MIXTURE OF TRIACYLGLYCEROLS : 80 to 85% of the acids are saturated. FEATURES: Highest saponification value Lowest iodine value among the common fixed oils Semisolid at 20°C MAJOR FATTY ACIDS: Lauric Myristic Also contains acyl glycerols of caprylic (8:0) and capric (10:0) acids from freshly part (mesocarp) Scientific name: Elaeis guineensis Family: Arecaceae ORIGIN: Elaeis- derived from the Greek word elaion meaning oil Guineensis- indicates its origin Guinea Coast of Africa USES: mostly used as shortening, margarine and frying fat. Used in soap and candle manufacture FEATURES: Consists of mixture of triacylglycerol whose component acids are almost equal proportions of saturated and unsaturated fatty acids. one of the world’s most widely consumed edible oils, next to soybean oil
LIPIDS LIPIDS
MID^22 PHARMACOGNOSY AND PLANT CHEMISTRY LEC
SATURATED FIXED OILS
Coconut Oil because of its low molecular weight acids give the oil a high saponification value Palm Oil
LIPIDSLIPIDS
MID^22 PHARMACOGNOSY AND PLANT CHEMISTRY LEC
from palm kernels after separation, drying and cracking of the shell of the nut. Scientific name: Elaeis guineensis Family: Arecaceae A hard oil and closely resembles coconut oil with which it is easily interchangeable USES: cooking oil margarine shortening formulations, confectionary and baking products in the preparation of ice cream and mayonnaise. FEATURES: Composed mostly of saturated fatty acids solid at ambient temperatures Palm Kernel Oil
SATURATED FIXED OILS
LIPIDSLIPIDS
MID^22 PHARMACOGNOSY AND PLANT CHEMISTRY LEC
MONOUNSATURATED FIXED OILS
ripe fruit Scientific name: Olea europea Family: Oleaceae GRADES OF PURITY: Virgin oil - gently pressing the peeled pulp with greater pressure
First Class or First Grade oil - pressed from crushed pulp with less pressure
Second Grade of edible oil is pressed from crushed pulp with greater pressure. --> Hand- picked olives are used, and
. the oil is obtained promptly. . before decomposition produces. . fatty acids. --> Finally, the pulp, mixed with hot.. . water, is pressed again Olive Oil aka Sweet Oil Technical oil: or the pulp is extracted with Carbon Disulfide to obtain “Sulfur” Olive oil of inferior quality. -->The fallen, decomposed or refused . leaves that are allowed to ferment . furnish a low grade “tournant oil”. . which contains large amounts of.. . free fatty acids. FATTY ACIDS (SLOP HAM) Stearic acid Linoleic acid Oleic acid Palmitic acid Hexadecanois acid Arachidic acid Myristic acid USES: pharmaceutic aid setting retardant for dental cements preparation of soaps, plasters and liniments demulcent emollient laxative nutrient salad oil
LIPIDSLIPIDS
MID^22 PHARMACOGNOSY AND PLANT CHEMISTRY LEC
MONOUNSATURATED FIXED OILS
Scientific name: Arachis hypogaea Family: Fabaceae USES: solvent for intramuscular injections PEANUT OIL CAKE - the residue following expression of the fixed oil, is valuable livestock food FEATURES: contain about 45% fixed oil, 20% protein and thiamine; highly nutritious used as food, both whole and when ground into paste (PEANUT BUTTER) arachis oil colorless liquid or a yellowish liquid with a slightly nutlike odor and a bland taste. resembles olive oil Used as food oil Peanut Scientific name: Brassica campestris, Brassica juncea, Brassica napus Family: Brassicaceae Oil obtained from these varieties is termed canola oil CANOLA OIL: CANada Oil Low Acid Oil USES Refined canola oil has bland taste and resist clouding at refrigeration temperature; therefore it is extensively used as salad oil Used as shortenings, margarines frying oil FEATURES: Consist of triacylglycerols that are rich in unsaturated fatty acids contained up to 50% erucic acid Rapeseed oil
LIPIDSLIPIDS
MID^22 PHARMACOGNOSY AND PLANT CHEMISTRY LEC
POLYUNSATURATED FIXED OILS
Scientific name: Gossypium hirsutum Family: Malvaceae USES: Used as a solvent for a number of injections. A considerable quantity is hydrogenated and used to make substitutes for lard. A large amount is also used in the manufacture of soaps. FATTY ACIDS:
- Linoleic acid (45%)
- Oleic acid (30%)
- Palmitic acid ( 20%)
- Myristic acid ( 3%)
- Stearic acid (1%)
- Arachidic acid (1% ) COTTONSEED CAKE Contains about 0.6% of a toxic principle, GOSSYPOL which occurs in secretory cavities in all parts of the plants. It is present in cold-pressed oil and can beremoved by treatment with alkalies. Cottonseed oil Scientific name: Sesamum indicum Family: Pedaliaceae The seeds are small, flattened, oval orovate, smooth and shiny, and whitish, yellow or reddish brown. Their taste is sweet and oily. They contain 45-55% of fixed oil, 22% of proteins (aleurone), and 4% of mucilage. The seeds are nutritious and form an important form in India. Used as poppy seeds on breads and rolls SESAME OIL/TEEL OIL or BENNE OIL Sesamum seed or Sesame seed The oil is pale yellow, oily liquid, almost odorless and bland tasting. The excellent stability of the oil is due to the phenolic constituent sesamol, which is produced by hydrolysis of sesamolin - lignan present in the unsaponifiable fraction of the oil.
Scientific name: Sesamum indicum Family: Pedaliaceae FATTY ACIDS: (OLPS)
- Oleic acid (43%)
- Linoleic acid (43%)
- Palmitic (9%)
- Stearic acid (4%) USES Used as solvent for intramuscular injections. It has nutritive, laxative, demulcent, and emollient properties. SESAMOLIN, contained in the unsaponifiable fraction of the oil, is an effective synergist for pyrethrum insecticides
LIPIDS LIPIDS
MID^22 PHARMACOGNOSY AND PLANT CHEMISTRY LEC
POLYUNSATURATED FIXED OILS
Sesamum seed or sesame seed SESAME OIL/TEEL OIL or BENNE OIL Sweet almond and bitter almond consist of the ripe seeds Scientific name: Prunus amygdalus Family: Rosaceae Both bitter and sweet almonds are expressed for their fixed oil (45 to 50%) Sweet almonds are extensively used as food but bitter almonds are not suitable for this purpose. ALMOND OIL, EXPRESSED ALMOND OIL, OR SWEET ALMOND OIL Almond oil fixed oil obtained by expression from the kernels of varieties of Prunus amygdalus. FATTY ACIDS PRESENT:
Oleic acid (77%)
Linoleic acid (17%)
Palmitic acid (5%)
Myristic acid (1%) USES emollient ingredient in cosmetics
Scientific name: Carthamus tinctorius Family: Asteraceae FATTY ACIDS
- Linoleic acid 75%
- Oleic acid 18%
- Saturated fatty acids about 6% USES high-calorie dietary supplement
LIPIDS LIPIDS
MID^22 PHARMACOGNOSY AND PLANT CHEMISTRY LEC
POLYUNSATURATED FIXED OILS
Safflower oil dried ripe seed Scientific name: Linum usitatissimum Family: Linaceae yellow liquid having a distinct odor and disagreeable taste. When exposed to air it gradually thickens and darkens in color FATTY ACIDS
- 52% Linolenic acid
- 15% Linoleic acid
- 19% oleic acid
- 7% stearic acid
- 6 % palmitic acid Linseed oil aka Flaxseed oil Scientific name: Helianthus annuus Family: Asteraceae FATTY ACIDS
- Linoleic acid 66%
- Oleic acid 23% USES alternative to corn oil and safflower oil for culinary purposes. Sunflower oil
fresh liver Scientific name: Gadus morhua Family: Gadidae It is a thin, oily liquid that has distinctive, slightly fishy but not rancid odor and a fishy taste. Medicinal grade cod liver oil must contain, not less than 255 ug ( units) of vitamin D USES Sources of Vitamin A and D Topical emollient
LIPIDS LIPIDS
MID^22 PHARMACOGNOSY AND PLANT CHEMISTRY LEC
POLYUNSATURATED FIXED OILS
COD Liver oil Ethiodized oil is an Iodine addition product of the Ethyl ester of the fatty acids of poppy seed oil. It contains not less than 35.2% and not more than 38.9% of organically combined iodine. It decomposes when exposed to air and sunlight, becoming dark brown in color. Ethiodized oil is packaged in sterile form. USES: diagnostic aid in hysterosalpingography and lymphography. Ethiodized oil injection
FATS
It is refined, bleached, hydrogenated, and deodorized vegetable stearin and consists mainly of the triglycerides of stearic and palmitic acids. It is a fine, white powder at room temperature and melts between 61 to 66C to give a pale yellow, oily liquid. USES: tablet lubricant
LIPIDS LIPIDS
MID^22 PHARMACOGNOSY AND PLANT CHEMISTRY LEC
Hydrogenated Vegetable oil The chief constituents are cholesterol and isocholesterol. Lanolin also contains the esters of lanopalmitic, lanoceric, carnaubic, oleic, myristic and other fatty acids. USES:
- Cosmetics
- Rust proof coatings and lubricants Raw material in the cholecalciferol production
As a water absorbable ointment base
but can cause allergenic reactions to hypersensitive persons Lanolin Scientific name: Ovies aries Family: Bovidae It contains between 25 to 30% of water and therefore is commonly called hydrous wool fat. A yellowish white, ointment like mass that has a slight characteristic odor. When heated on a steam bath, it separates at first into 2 layers. Continued heating with frequent stirring drives off the water that makes up the lower layer.
ANHYDROUS LANOLIN
It contains not more than 0.25% of water. After lanolin, has been purified and bleached, it is dehydrated. Anhydrous lanolin is usually referred as wool fat USES: Used as water absorbable ointment base
FATTY ACIDS
LIPIDS LIPIDS
MID^22 PHARMACOGNOSY AND PLANT CHEMISTRY LEC
This are usually obtained by hydrolysis of fats and oils. Stearic acid These are hard, white or faintly yellow solids or powders insoluble in water USES: emulsion adjunct and tablet lubricant SALTS: USES: Calcium stearate Magnesium stearate Zinc stearate Sodium stearate Aluminum monostearate Glyceryl monostearate Propylene glycol monostearate tablet lubricants dusting powders emulsifying, stiffening agent suspending agent emulsifying agent emulsifying agent Isopropyl Myristate and Isopropyl Palmitate mixtures consisting of the esters of isopropyl alcohol and saturated high molecular weight fatty acids. The respective semisynthetic products contain not less than 90% of the designated esters. USES: ingredients in topical ointment and creams. • ADVANTAGES: They offer some advantage over vegetable oils, including freedom from oxidation and rancidity and a less oleaginous (greasy) character. In addition, they lack the hypersensitization potential encountered with lanolin. Oleic acid Obtained from edible fats and fixed oils by product in the production of stearic acid Consists chiefly of cis-9-octadecenoic acid Pale yellow oily liquid It is practically insoluble in water but is miscible with alcohol It gradually absorbs oxygen and darkens when exposed to air An emulsion adjunct
