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Chemistry of phospholipids
DR ROHINI C SANE
PROFESSOR
DEPARTMENT OF BIOCHEMISTRY
DR D Y PATIL MEDICAL COLLEGE
EBENE
CLASSIFICATION OF PHOSPHOLIPIDS
• FATTY ACIDS +ALCOHOL+NITRGEN BASE+ PHOSPHARIC ACID
• I GLYCEROPHOSPHOLIPIDS ----OR PHOSP...
GLYCEROPHOSPHOLIPIDS
• GLYCEROPHOSPHOLIPIDS---MAJOR LIPID IN BIOLOGICAL
MEMBRANE
• GLYCEROL -3-P IS esterified at C1& C2.
...
GLYCEROPHOSPHOLIPIDS
TYPE 2 –LECITHIN—PHOSPOTIDYL CHOLINE
FATTY ACID +GLYCEROL )CHOLINE
• MOST ABUNDANT GROUP OF PHOSPHOLI...
GLYCEROPHOSPHOLIPIDS
TYPE III CEPHALIN ---(PHOSPHOTIDYL ETHANOLAMINE)
FATTY ACIDS +GLYCEROL +PHOSPHARIC ACID -ETHANOLAMINE...
GLYCEROPHOSPHOLIPIDS
TYPE V PHOSPHTIDYL SERINE /PHOSPHOTIDYL THREONINE
• FATTY ACIDS +GLYCEROL +PHOSPHARIC ACID+SERINE
• F...
GLYCEROPHOSPHOLIPIDS
CARDIOLIPINS
FATTY ACIDS +2 GLYCEROL +2PHOSPHARIC ACID(LINKED THROUGH P
GROUP )
ISOLATED FROM HEART M...
FUNCTIONS OF PHOSPHOLIPIDS
1. Along with structural component of membrane regulate membrane
permeability
2. ( lecithin /ce...
FUNCTIONS OF PHOSPHOLIPIDS
9. REVERSE CHOLESTEROL TRANSPORT
• Eg LDL carrier of endogenous Cholesterol (LIVER TO PERIFERAL...
Phospholipids—Glycolipids /Sphingolipid
1) fatty acid + glycerol+ nitrogen base + p >>>Glycerophospholipid
2) fatty acid +...
LIPID STORAGE DISEASE
• LYSOSOMAL STORAGE DEFECT
• INHERITED DISORDERS ( GENETIC DISEASE)
• ACCUMULATION OF COMPLEX LIPIDS...
LIPID STORAGE DISEASE
•
• GAUCHER”S DISEASE
• GLUCOCERBROSIDES----------------------GLUCOSE + CERAMIDE
• (GLU –CER) BETA G...
LIPID STORAGE DISEASE
• KRABB”S DISEASE
• BETA GALACTOSIDASE
• GALACTOCERBROSIDES--------------------------GALACTOSE + CER...
LIPID STORAGE DISEASE
• Niemann”s Pick”s Disease
• sphingomylinase
• Sphingomylin ----------------------- - choline p+ cer...
LIPID STORAGE DISEASE
• Faber”s disease
• Ceramidase
• Ceramide --------------------fatty acid + sphingosine
• Symptoms
• ...
LIPID STORAGE DISEASE
• GANGLIOSIDES -----COMPLEX GLYCOSPHINGOLIPIDS FOUND IN
GANGLIONS.
• THEY CONTAIN ONE OR MORE MOLECU...
LIPID STORAGE DISEASE
DISEASE DEFECTIVE ENZYME STORAGE COMPOUND SYMPTOMS
NIEMANN”S
PICK
SPHINGOMYLINASE SPHINGOMYELINS ENL...
LIPID STORAGE DISEASE
DISEASE DEFECTIVE ENZYME STORAGE COMPOUND SYMPTOMS
KRABB”S
DISEASE
BETA
GALACTOSIDASE
GALACTOCEREBRO...
LIPID STORAGE DISEASE
DISEASE DEFECTIVE ENZYME STORAGE COMPOUND SYMPTOMS
FABRY”S ALPHA
GALACTOSIDASE
CERAMIDE TRIHEXOSIDE ...
Tay Sach disease: Inheritance
It is inherited as an autosomal recessive traits, with
a predilection in the Ashkenazi Jewis...
Diagnosis of Tay-Sach disease
• is usually suspected in an infant with neurologic features and a cherry-red spot.
• Enzyma...
LIPOSOMES --NANO DRUG DELIVERY SYSTEM
LIPOSOMES
• SELECTIVE FUSION OF LIPOSOMES WITH TARGET CELLS –
CONTROLLING DRUG DELIVERY TO SPECIFIC CELLS –CANCER
TREATMEN...
Detergents
I NATURAL a. Bile Salts &bile acids
Emulsification of fat in GIT
II SYNTHETIC
A. Anionic –SODIUM DODECYL SULPHA...
•
•
Chemistry of Phospholipids
Chemistry of Phospholipids
Chemistry of Phospholipids
Chemistry of Phospholipids
Chemistry of Phospholipids
Chemistry of Phospholipids
Chemistry of Phospholipids
Chemistry of Phospholipids
Chemistry of Phospholipids
Chemistry of Phospholipids
Chemistry of Phospholipids
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Chemistry of Phospholipids

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Chemistry of Phospholipids

  1. 1. Chemistry of phospholipids DR ROHINI C SANE PROFESSOR DEPARTMENT OF BIOCHEMISTRY DR D Y PATIL MEDICAL COLLEGE EBENE
  2. 2. CLASSIFICATION OF PHOSPHOLIPIDS • FATTY ACIDS +ALCOHOL+NITRGEN BASE+ PHOSPHARIC ACID • I GLYCEROPHOSPHOLIPIDS ----OR PHOSPHOGLYCERIDE---GLYCEROL /ALCOHOL • II SPHINGOPHOSPHOLIPIDS----SPHINGOMYELINS----ALCOHOL – SPHINGOSINE
  3. 3. GLYCEROPHOSPHOLIPIDS • GLYCEROPHOSPHOLIPIDS---MAJOR LIPID IN BIOLOGICAL MEMBRANE • GLYCEROL -3-P IS esterified at C1& C2. • C1---SATURATED FATTY ACID • C2 ---UNSATURATED FATTY ACID • TYPE –1—PHOSPHATIDIC ACID • INTERMEDIADE IN SYNTHESIS OF TRIGLYCEROL & PHOSPHOLIPIDS
  4. 4. GLYCEROPHOSPHOLIPIDS TYPE 2 –LECITHIN—PHOSPOTIDYL CHOLINE FATTY ACID +GLYCEROL )CHOLINE • MOST ABUNDANT GROUP OF PHOSPHOLIPID IN CELL MEMBRANE • PHOSPHATIDIC ACID + CHOLINE • STORAGE OF BODY”CHOLINE (DONAR OF METHYL GROU IN METHYLATION REACTIONS ) • CHOLINE –ACETYL CHOLINE NERVE IMPULSE TRANSMISSION • LYSOLECITHIN –REMOVAL OF FATTY ACIDS FROM C1 OR C2 OF LECTHIN DIPALMITOL LECITHIN –MAINTAIN SURFACE TENSION—ADHERENCE OF INNER SURFACE OF LUNGS DEFICIENCY –RESPIRATORY DISTRESS SYNDROME IN INFANTS
  5. 5. GLYCEROPHOSPHOLIPIDS TYPE III CEPHALIN ---(PHOSPHOTIDYL ETHANOLAMINE) FATTY ACIDS +GLYCEROL +PHOSPHARIC ACID -ETHANOLAMINE(NITROGEN BASE ) • CLOTTING FACTOR III THROMBOPLASTIN –CEPHALIN • FUNCTION HELPS IN CLOTTING OF BLOOD TYPE IV PHOSPHOTIDYL INOSITOL FATTY ACIDS +GLYCEROL +PHOSPHARIC ACID—INOSITOL SECONDARY MESSENGER FOR OXYTOCIN,VASSOPRESSIN
  6. 6. GLYCEROPHOSPHOLIPIDS TYPE V PHOSPHTIDYL SERINE /PHOSPHOTIDYL THREONINE • FATTY ACIDS +GLYCEROL +PHOSPHARIC ACID+SERINE • FATTY ACIDS +GLYCEROL +PHOSPHARIC ACID+ THREONINE • FOUND IN MOST TISSUES TYPE VI PLASMALOGENS • FATTY ACIDS LINKED WITH ETHER LINKAGE (NOT ESTER LINKAGE ) FUNCTIONS • MYELIN SHEETH FORMATION • CARDIAC MUSCLES • PLATELET AGGREGATION
  7. 7. GLYCEROPHOSPHOLIPIDS CARDIOLIPINS FATTY ACIDS +2 GLYCEROL +2PHOSPHARIC ACID(LINKED THROUGH P GROUP ) ISOLATED FROM HEART MUSCLES PRESENT IN INNER MITOCHONDRIAL MEMBRANE ANTIGENIC PROPERTIES
  8. 8. FUNCTIONS OF PHOSPHOLIPIDS 1. Along with structural component of membrane regulate membrane permeability 2. ( lecithin /cephalin /cardiolipin )—present in electron transport chain –assist in cell respiration 3. Amphipathic nature – combine with polar & nonpolar compounds 4 .absorption of fat from intestine 5.lipoprotein synthesis---lipid transport (LDL/VLDL/HDL) 6.PREVENT FATTY LIVER—REGARDED AS LIPOTROPIC FACTORS 7.SYNTHESIS OF PROSTAGLANDINS /PROSTCYCLINS /THROMBOXANES PHOSPHOLIPIDSARACHIDONIC ACIDS-EICOSANOIDS
  9. 9. FUNCTIONS OF PHOSPHOLIPIDS 9. REVERSE CHOLESTEROL TRANSPORT • Eg LDL carrier of endogenous Cholesterol (LIVER TO PERIFERAL TISSUE) • VLDL carrier of endogenous TRIGLYCEROL (LIVER TO PERIFERAL TISSUE) 10.SURFACTANT –(LOWERING SURFACE TENSION )—eg –Dipalmitoyl phosphatidyl choline –lung surfactant –deficiency respiratory distress syndrome 11.Singnal transmission across the membrane 12.Component of bile –emulsification of fat
  10. 10. Phospholipids—Glycolipids /Sphingolipid 1) fatty acid + glycerol+ nitrogen base + p >>>Glycerophospholipid 2) fatty acid + spingol /sphingosine>>ceramide 3) fatty acid + sphingosine+ Nitrogen base > sphingophospholipids Ceramide 4) fatty acids + sphingosine + carbohydrate *>>>Glycolipids Ceramide + galactose *>>>> Ceramide+ glucose *>>>> 5) fatty acid + sphingosine + glucose+ ( galactose ---n acetylgalactosamine—galactose )+ NANA ( N ACETYL neuaminic acid ) Ceramide +glucose + galactose ---n acetylgalactosamine— galactose )+NANA …………. Gangliosides
  11. 11. LIPID STORAGE DISEASE • LYSOSOMAL STORAGE DEFECT • INHERITED DISORDERS ( GENETIC DISEASE) • ACCUMULATION OF COMPLEX LIPIDS----- SPHINGOLIPID/SPHINOMYELINS)
  12. 12. LIPID STORAGE DISEASE • • GAUCHER”S DISEASE • GLUCOCERBROSIDES----------------------GLUCOSE + CERAMIDE • (GLU –CER) BETA GLUCOSIDASE • SYMPTOMS • ENLARGEMENT OF LIVER SPLEEN • OSTEOPOROSIS • PIGMATION OF SKIN • ANAEMIA • MENTAL RETARDATION • FATAL
  13. 13. LIPID STORAGE DISEASE • KRABB”S DISEASE • BETA GALACTOSIDASE • GALACTOCERBROSIDES--------------------------GALACTOSE + CERAMIDES • (GAL-CER) • Absence of myelin in nervous tissue • Mental retardation • Convulsions • Blindness • Deafness • Fatal in early life •
  14. 14. LIPID STORAGE DISEASE • Niemann”s Pick”s Disease • sphingomylinase • Sphingomylin ----------------------- - choline p+ ceramide • (choline-p-cer) • Accumulation of sphingomyelins in liver & spleen----- enlargement • Mental retardation • Death early childhood
  15. 15. LIPID STORAGE DISEASE • Faber”s disease • Ceramidase • Ceramide --------------------fatty acid + sphingosine • Symptoms • Skeletal deformation • Subcutaneous nodules • Dermatitis • Mental redardation • Fatal in early life
  16. 16. LIPID STORAGE DISEASE • GANGLIOSIDES -----COMPLEX GLYCOSPHINGOLIPIDS FOUND IN GANGLIONS. • THEY CONTAIN ONE OR MORE MOLECULES OF NANA (N acetyl neuraminic acid) BOUND TO CERAMIDE OLIGO SACCHARRIDES. • DEFECT IN DEGRDTION OF GANGLIOSIDES CAUSES GANGLIOSIDOSIS---- • TAY SACH” S DISEASE
  17. 17. LIPID STORAGE DISEASE DISEASE DEFECTIVE ENZYME STORAGE COMPOUND SYMPTOMS NIEMANN”S PICK SPHINGOMYLINASE SPHINGOMYELINS ENLARGED LIVER & SPLEEN MENTAL RETARDATION FABERS CERAMIDASE CERAMIDE PAINFUL JOINTS AND DEFORMED JOINTS GAUCHER”S Β GLUCOSIDASE GLUCOCEREBROSIDE ENLARGED LIVER & SPLEEN MENTAL RETARDATION, OSTEOPOROSIS
  18. 18. LIPID STORAGE DISEASE DISEASE DEFECTIVE ENZYME STORAGE COMPOUND SYMPTOMS KRABB”S DISEASE BETA GALACTOSIDASE GALACTOCEREBROSIDE ENLARGED LIVER & SPLEEN, ABSENCE OF MYELIN FORMATION MENTAL RETARDATION TAY SACH”S DISEASE Hexosaminidase Ganglioside GM2 BLINDNESS PAINFUL JOINTS AND DEFORMED JOINTS ENLARGED LIVER & SPLEEN MENTAL RETARDATION, DEATH 2-3 YRS
  19. 19. LIPID STORAGE DISEASE DISEASE DEFECTIVE ENZYME STORAGE COMPOUND SYMPTOMS FABRY”S ALPHA GALACTOSIDASE CERAMIDE TRIHEXOSIDE RENAL FAILURE ,SKIN RASH ,PAIN IN LOWER EXTREMITIS
  20. 20. Tay Sach disease: Inheritance It is inherited as an autosomal recessive traits, with a predilection in the Ashkenazi Jewish population, where the carrier frequency is about 1/25.
  21. 21. Diagnosis of Tay-Sach disease • is usually suspected in an infant with neurologic features and a cherry-red spot. • Enzymatic Assays-Definitive diagnosis is by determination of the level of ß-hexosaminidase A in isolated blood leukocytes. • Fine needle Aspiration Cytology of brain tissue – can show the degree of neuronal degeneration. FNAC has a great potential for diagnosis and follow-up of Tay-Sachs disease • Prenatal screening-Future at-risk pregnancies for both disorders can be monitored by prenatal diagnosis by amniocentesis or chorionic villous sampling. • Carrier screening- Identification of carriers within families is also possible by ß- hexosaminidase A and B determination.
  22. 22. LIPOSOMES --NANO DRUG DELIVERY SYSTEM
  23. 23. LIPOSOMES • SELECTIVE FUSION OF LIPOSOMES WITH TARGET CELLS – CONTROLLING DRUG DELIVERY TO SPECIFIC CELLS –CANCER TREATMENT • REDUCE SIDE EFFECTS OF TOXIC DRUGS • IMPROVE PHARMOCOKINETIC &PHARMACODYMICS OF DRUGS
  24. 24. Detergents I NATURAL a. Bile Salts &bile acids Emulsification of fat in GIT II SYNTHETIC A. Anionic –SODIUM DODECYL SULPHATE (USED IN ELECTROPHORESIS ANALYSIS ) PROTEIN +SDS = SOLUBILIZATION OF PROTEINS(SO4 IMPARS NEGATIVE CHARGE ) --- IMPARTS NEGATIVE CHARGE B.CATIONIC ---CETYL TRIMETHYL AMMONIUM BROMIDE (CTAB) ANTIBACTERIAL AGENTS (HAND WASH CREAMS ) DESTROYING BACTERIAL MEMBRANE PROTEIN CARRY POSITIVE CHARGE.
  25. 25. • •

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