OTHER COMPOUNDS OF LIPIDS

DR. REYNAN D. NADERA

ASSOCIATE PROFESSOR IV
 LIPIDS NOT CONTAINING GLYCEROL
1. SPHINGOLIPIDS – IMPORTANT COMPONENTS OF PLANTS AND ANIMAL CELL.
- PRESENT IN LARGE AMOUNTS IN BRAIN AND NERVE TISSUES.
D4 SPHINGENINE (SPHINGOSINE) (SPHINGANINE) (DIHYDROSPHINGOSINE) – THE
BUILDING BLOCK OF ALL SPHINGOLIPIDS
a. CEPHALINS – PHOSPHOLIPIDS IN WHICH THE NITROGEN IS IN THE FORM OF A PRIMARY
AMINO GROUP ( ETHANOLAMINE OR SERINE).
Occurrence: brain, spinal cord, soy beans
Properties:
1. The same solubilities as the lecithins with one exceptions.
they are insoluble in either ethyl or methyl alcohol.
2. Strongly acidic.
 LIPIDS NOT CONTAINING GLYCEROL
PHYSIOLOGICAL IMPORTANCE
1. INITIATE THE PROCESS OF BLOOD COAGULATIONS.
2. IMPORTANT CONSTITUENT OF BRAIN AND LUNG PHOSPHOLIPIDS.
B. SPHINGOMYELINS – PHOSPHOLIPIDS WHICH CONSIST OF ACID AMIDES OF SPHINGOSINE
WITH FATTY ACIDS IN ESTER LINKAGE WITH PHOSPHORYL-CHOLINE.
OCCURRENCE: BRAIN, LIVER, KIDNEY ANG EGG YOLK.
PROPERTIES:
a. WHITE CRYSTALLINE, NON HYGROSCOPIC SUBSTANCES.
b. RELATIVELY STABLE TO LIGHT AND AIR.
c. BECOMES HYDRATED AND EMULSIFIED IN WATER.
d. INSOLUBLE IN ETHER AND COLD ALCOHOL,
 LIPIDS CONTAINING GLYCEROL
PHYSIOLOGICAL IMPORTANCE
1. IMPORTANT CONSTITUENT OF THE BRAIN AND NERVE TISSUES, SPLEEN AND LUNGS.
2. LIPIDS OF THE BLOOD.
1.LECITHINS – PHOSPHORIC ESTERS OF DIGLYCERIDES AND CHOLINE
OCCURRENCE: LIVER, BRAIN, NERVOUS TISSUE EGG YOLK.
PROPERTIES:
2.ON HYDROLYSIS, IT FORMS GLYCEROL, FATTY ACIDS, PHOSPHORIC ACID AND NITROGENOUS BASE CHOLINE.
3.FORMS COLLOIDAL SOLUTIONS WITH WATER.
4.FORMS A WATER SOLUBLE COMPOUND WITH BILE SALTS
5.FORMS COMP0LEXES WITH PROTEIN CALLED LECITHOPROTEINS.
6.SPLIT BY ENZYMES LIPASE AND LECITHINASE.
 LIPIDS CONTAINING GLYCEROL
6. TRANSLUSCENT, PARAFFIN-LIKE, COLORLESS SOLIDS WHICH QUICKLY TURN YELLOW ON
EXPOSURE TO AIR AND FINALLY BECOMES OPAQUE BROWN.
7. SOLUBLE IN MAY FAT SOLVENT INCLUDING ETHER, CHLOROFORM, BENZENE AND HOT
ALCOHOL. THEY ARE NOT SOLUBLE IN ACETONE.
8. WHEN HEATED WITH DEHYDRATING AGENTS, THEY YIELD ACROLEIN.
9. SAPONIFIED BY ALKALIES TO PRODUCE GLYCEROL, SOAPS, CHOLINE AND PHOSPHATES.
PHYSIOLOGICAL IMPORTANCE;
1.ASSIST IN REGULATING THE PERMEABILITY OF THE CELL MEMBRANE.
2.MAINTAINS PROTOPLASMIC STRUCTURE
3.FORMS COORDINATE COMPLEXES WITH PROTEINS AND IN THE FORM OF LECITHOPROTEINS
PLAY IMPORTANT PHYSIOLOGICAL ROLES.
4.INTERMEDIATE STAGE IN THE METABOLISM OF FATTY ACIDS.
LIPIDS CONTAINING GLYCEROL

BETA LECITHINS ALPHA LECITHINS

 LIPIDS NOT CONTAINING GLYCEROL
2. GLYCOLIPIDS – THE LIPIDS WITH CARBOHYDRATES ATTACHED BY A GLYCOSIDIC, MAINLY
OCCUR IN THE CELL MEMBRANE.
A. CEREBROSIDES – GLYCOLIPIDS/GALACTOSIDES, GALACTOLIPIDS, D-GALACTOSE AND C24
ACID. IT CONTAIN NITROGEN BUT NO PHOSPHORUS.
PROPERTIES:
- WHITE AND MORE OR LESS WAX LIKE.
- INSOLUBLE IN ETHER, SOLUBLE IN ACETONE, HOT ALCOHOL BENZENE
AND CHLOROFORM.
- HYDROLYZED BY BOILING ACIDS
- RESISTANT TO ACTION BY ALKALIS
- NO SPLIT BY ANY ENZYMES.
 LIPIDS NOT CONTAINING GLYCEROL
PHYSIOLOGICAL IMPORTANCE
1. IMPORTANT CONSTITUENT OF THE MEDULLARY SHEATH OF NERVES IN BRAIN TISSUE PARTICULARLY IN WHITE
MATER OF THE BRAIN, SPLEEN, KIDNEY, LIVER, BLOOD CORPUSCLES, LUNGS, ADRENALS AND RETINA OF THE EYE.
B. GANGLIOSIDES OR ACIDIC GLYCOSPHINGOLIPIDS – HAVE POLAR HEAD THAT ARE OLIGOSACCHARIDES WITH
ONE OR MORE RESIDUE OF SIALIC ACID. IT IS FOUND IN GANGLION CELLS. COMPOSED OF ONE MOLECULE EACH
OF STEARIC ACID, SPHINGOSINE, NEURAMINIC ACID AND 3 MOLECULES OF MONOSACCHARIDES. NORMALLY THE
SUGAR IS GALACTOSE, PATHOLOGICALLY IT MAY BE GLUCOSE.
PHYSIOLOGICAL IMPORTANCE
-ATTENDANT IN NERVE ENDINGS
-FUNCTION IN THE TRANSMISSION OF NERVE IMPULSES ACROSS
THE SYNAPSE.
 LIPIDS NOT CONTAINING GLYCEROL
C. WAXES – ARE ESTER OF HIGHER FATTY ACIDS WITH MONO OR SOMETIMES DI HYDROXY SATURATED
LONG CHAIN MONOHYDRIC FATTY ALCOHOLS OR STEROLS.
OCCURRENCE:
- BEESWAX: IN HONEYCOMB
- SPERMACETTI: IN THE SKULL OF CERTAIN WHALES AND DOLPHINS
- CHINESE WAX: IN CUTICLE OF LEAVES
- CARNAUBA WAX: IN THE CUTICLE OF LEAVES
- CHOLESTERYL PALMITATE: IN BLOOD PLASMA
- LANOLIN: WOOL WAX
 LIPIDS NOT CONTAINING GLYCEROL
PROPERTIES
- INSOLUBLE IN WATER BUT SOLUBLE IN FAT SOLVENTS.
- NOT SO EASILY HYDROLYZED AS THE FATS AND ARE NOT DIGESTED BY THE FAT-
SPLITTING ENZYMES, THEREFORE NO NUTRITIONAL VALUE.
PHYSIOLOGICAL IMPORTANCE
-IT SERVES AS A PROTECTIVE AGENT ON THE SURFACES OF PLANTS AND ANIMALS.
-IT PROTECT FRUITS FROM EXCESSIVE LOSS OF MOISTURE.
USES:
- INGREDIENTS OF SHOE POLISH, VARNISHES, CANDLES
 NOT SAPONIFIABLE LIPIDS
1. TERPENES – POLYMERS OF ISOPRENE UNITS (5 CARBONS) JOINED HEAD TO TAIL. ISOPRENE
UNITS BY INGENIOUS CONSIDERATION GIVE RISE TO RUBBER, STEROIDS AND CAROTENOIDS.
2. STEROIDS – (STEROLS) ARE HYDROXYL DERIVATIVES OF
CYCLOPENTANOPERHYDROPHENANTRENE NUCLEUS.
- HAVE AN OXYGENATED SUBSTITUENT ON C-3 WHICH IS SHARED BY ALMOST ALL
NATURALLY OCCURRING STEROIDS.
- HERE ARE ANGULAR METHYL GROUPS AT C-10 AND C-13 AND
- THERE IS AN ALIPATHIC SUBSTITUENT AT C-17.
 SOME BIOLOGICALLY IMPORTANT STEROIDS
1. CHOLESTEROL – PRESENCE OF Β – OH AT C-3 DOUBLE BONDS AT 5,6 POSITION.
- SYNTHESIZED MAINLY AT THE LIVER AND THE MOST ABUNDANT STEROIDS IN THE HUMAN BODY.
- PERCEIVED AS BAD INSPITE OF ITS ESSENTIAL ROLE IN BIOLOGICAL PROCESSES.
OCCURRENCE: CONSTITUENT OF ANIMAL CELL. THE CORPUS LUTEUM AND THE ADRENAL CORTEX
ARE PARTICULARLY RICH IN THIS LIPIDS.
- PRESENCE IN THE PLASMA MEMBRANE AND LIPOPROTEINS OF BLOOD.
- MAJOR CONSTITUENT OF GALLSTONES.
- IT IS PRESENT IN NERVOUS TISSUE
- ALL ANIMALS CAN SYNTHESIZE CHOLESTEROL FROM OTHER DIETARY FACTORS.
- ALSO FOUND IN BILE AND EGG YOLK.
- PRECURSOR OF MANY OTHER STEROIDS IN ANIMAL TISSUE INCLUDING BILE ACIDS,
ANDROGENS, ESTROGEN AND THE ADRENOCORTICAL HORMONES.
 SOME BIOLOGICALLY IMPORTANT STEROIDS
PROPERTIES:
a. MELTS AT 150 °C, INSOLUBLE IN WATER, SOLUBLE IN MANY FAT SOLVENTS SUCH AS
ETHER, CHLOROFORM, BENZENE AND HOT ALCOHOL.
b. CANNOT BE SAPONIFIED.
c. CRYSTALLIZES FROM FAT SOLVENTS IN COLORLESS RHOMBIC PLATES WITH ONE OR
MORE CHARACTERISTIC NOTCHES IN THE CORNER.
d. IT WILL TAKE UP TWO HALOGEN ATOMS.
e. IT FORMS AN INSOLUBLE PRECIPITATE WITH DIGITONIN. THIS REACTION IS USED IN
THE QUANTITATIVE DETERMINATION OF CHOLESTEROL.
f. IT INHIBITS THE REACTION OF SAPONINS.
 SOME BIOLOGICALLY IMPORTANT STEROIDS
PROPERTIES:
a. MELTS AT 150 °C, INSOLUBLE IN WATER, SOLUBLE IN MANY FAT SOLVENTS SUCH AS
ETHER, CHLOROFORM, BENZENE AND HOT ALCOHOL.
b. CANNOT BE SAPONIFIED.
c. CRYSTALLIZES FROM FAT SOLVENTS IN COLORLESS RHOMBIC PLATES WITH ONE OR
MORE CHARACTERISTIC NOTCHES IN THE CORNER.
d. IT WILL TAKE UP TWO HALOGEN ATOMS.
e. IT FORMS AN INSOLUBLE PRECIPITATE WITH DIGITONIN. THIS REACTION IS USED IN
THE QUANTITATIVE DETERMINATION OF CHOLESTEROL.
f. IT INHIBITS THE REACTION OF SAPONINS.
 SOME BIOLOGICALLY IMPORTANT STEROIDS
PREPARATION: CHOLESTEROL IS EXTRACTED WITH ETHER FROM BRAIN TISSUE OR FROM
GALLSTONES.
COLOR REACTIONS:
A. SALKOWSKI REACTIONS – A SOLUTION OF THE STEROLS IN CHLOROFORM IS SHAKEN
WITH CONC. SULFURIC ACID. A CHERRY RED COLOR APPEARS IN BOTH LAYERS.
B. LIEBERMANN-BURCHARD TEST – THE STEROL IS TREATED WITH CHLOROFORM,
ACETIC ANHYDRIDE AND CONC. SULFURIC ACID PRODUCING A LILAC COLOR
TURNING BLUE AND FINALLY AN EMERALD GREEN COLOR.
C. STEINLE-KEBLENBERG REACTION – A CLEAR PURPLE SOLUTION CHANGING TO
COBALT BLUE ON EXPOSURE TO LIGHT OF STEROL IN CHLOROFORM SOLUTION ON
TREATING WITH ANTIMONY PENTACHLORIDE.
 SOME BIOLOGICALLY IMPORTANT STEROIDS
LIPOPROTEIN – LIPID PROTEIN COMPLEXES.
a. CHYLOMICRONS
B. VERY LOW DENSITY LIPOPROTEINS (VLDC)
C. INTERMEDIATE DENSITY LIPOPROTEIN (IDL)
D. LOW DENSITY LIPOPROTEIN (LDL)
E. HIGH DENSITY LIPOPROTEIN (HDL)
Recommended levels of blood HDL and LDL- cholesterol
Type of Patient LDL- cholesterol (mg/dL) HDL- cholesterol (mg/dL0

Coronary patients < 100 > 35

Middle-aged individuals with no <130 > 35

coronary disease.
 SOME BIOLOGICALLY IMPORTANT STEROIDS
IMPORTANCE OF CHOLESTEROL
a. IN THE BLOOD, IT TRANSPORT FATTY ACIDS IN THE FORM OF CHOLESTEROL ESTERS.
b. IN THE NERVE TISSUES, IT SERVES AS AN INSULATOR BY FORMING A PART OF THE
MYELIN SHEATH.
c. IT MAINTAINS THE NORMAL PERMEABILITY OF THE CELL WALL.
2. 7-DEHYDROCHOLESTEROL – POSSES A CONJUGATED PAIR OF DOUBLE BONDS BETWEEN
5, 6, AND 7, 8.
OCCURRENCE :
DERIVED FROM OXIDATION OF CHOLESTEROL, FOUND UNDERNEATH THE SKIN.
COLOR REACTION: SAME AS CHOLESTEROL
 SOME BIOLOGICALLY IMPORTANT STEROIDS
IMPORTANCE
WHEN THE SKIN IS IRRADIATED WITH ULTRAVIOLET LIGHT, THE STEROL IS CONVERTED
TO ONE OF THE VIT. D CALLED “PRO-VITAMINS. THIS EXPLAIN THE VALUE OF SUNSHINE IN
PREVENTING RICKETS.
3. BILE ACIDS (24 CARBONS)
a. THEY HAVE A SIDE CHAIN AT C-17 WHICH IS 5 CARBON ATOMS LONG ENDING IN A
COOH GROUP.
b. BECAUSE OF THE PRESENCE OF EXTRA OH AND COOH GROUPS IN THE SIDE CHAIN.
THEY ARE GOOD EMULSIFIERS AND AID IN THE ABSORPTION AND DIGESTION OF LIPIDS
IN THE INTESTINE.
 SOME BIOLOGICALLY IMPORTANT STEROIDS
4. ADRENOCORTICAL HORMONES OR CORTICOSTEROIDS (21 AND 22 CARBON ATOMS)
CORTISOL/HYDROCORTISONE./ 17 HYDROCORTICOSTERONE.
a. ISOLATED FROM THE ADRENAL CORTEX, AND ARE CONSIDERED CHOLESTEROL
DERIVATIVES.
b. HELP REGULATE THE METABOLISM OF ELECTROLYTES, PROTEIN AND CARBOHYDRATES
c. HAVE ANTI INFLAMMATORY AND ANTI IMMUNE EFFECTS.
5. ANDROGENS AND ESTROGENS (SEX HORMONES) ( 18 AND 19 CARBON ATOMS)
ANABOLIC STEROIDS – ARTIFICIALLY SYNTHESIZED DERIVATIVES OF THE MALE SEX
HORMONES ,IT STIMULATES SPECIFIC ANABOLIC PROCESSES INCLUDING MUSCLE
PRODUCTION, ABUSED BY ATHLETES TRYING TO IMPROVE THEIR PERFORMANCE.
 SOME BIOLOGICALLY IMPORTANT STEROIDS
ESTROGEN- WITH AROMATIC RING, THE OH AT C-3 IS PHENOLIC, HENCE ESTROGEN BEHAVE
LIKE WEAK ACIDS. IT IS EXTRACTABLE FROM BENZENE SOLUTION WITH AQUEOUS
ALKALI.
Β- ESTRADIOL THE ESTROGEN SECRETED FROM THE OVARY.
IMPORTANCE:
A. IT HELPS DEVELOP AND MAINTAIN BOTH THE REPRODUCTIVE SYSTEM AND FEMALE
CHARACTERISTICS SUCH AS BREAST AND PUBIC HAIR.
B. CONTRIBUTES TO COGNITIVE HEALTH
C. BONE HEALTH
D. INVOLVE IN THE FUNCTION OF CARDIOVASCULAR SYSTEM.
 SOME BIOLOGICALLY IMPORTANT STEROIDS
6. PROSTAGLANDINS/EICOSANOIDS – EXHIBIT A VARIETY OF POTENT BIOLOGICAL
ACTIVITIES OF A HORMONAL OR REGULATORY IN NATURE.
OCCURRENCE : FORM AT THE SITE OF TISSUE DAMAGE OR INFECTION THAT ARE
INVOLVED IN DEALING WITH INJURY AND ILLNESS.
PROSTANOIC ACID – THE PARENT COMPOUND OF ALL PROSTAGLANDINS (PG). IT IS A 20
–CARBON CARBOXYLIC ACID CONSISTING OF A CYCLOPENTANE UNIT AND 2 ALIPHATIC SIDE
CHAINS.
IMPORTANCE:
A. CONTROL PROCESSES SUCH AS INFLAMMATION, BLOOD FLOW, FORMATION OF
BLOOD CLOTS.
 SOME BIOLOGICALLY IMPORTANT STEROIDS
7. SQUALAMINE – ISOLATED FROM DOG SHARK AND ARE IS CLASSIFIED AS AN ANTIBIOTIC. IT KILLS A BROAD
RANGE OF MICROORGANISMS, INCLUDING CANDIDA, A FUNGUS THAT COMMONLY INFECTS
INDIVIDUALS WITH SUPPRESSED IMMUNE SYSTEMS.
IMPORTANCE:
A. USE/TREATMENT IN OVARIAN CANCER, LUNG CANCER AND MACULAR DEGENERATION.