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Complex lipids
• Classification
• Structure & function of phospholipids &
glycolipids
12-10-2011
Classification
Phospholipids Glycolipids Lipoproteins Sulfolipids
Complex lipids
Phospholipids
• Complex lipids
• Containing phosphoric acid, in addition to fatty
acids, nitrogenous base and alcohol
Classification
Phospholipids
Glycerophospholipids Sphingophospholipids
Micelles are spherical
structures that have a
nonpolar, hydrophobic
environment in the
core, and a polar,
aqueous environment
on the surface. The bile
salt-lipid complexes
formed in the small
intestine are micelles.
Glycerophospholipids
• Membrane lipids
• Alcohol is glycerol
Glycerophospholipids
Phosphatidyl choline (Lecithin)
• Most abundant phospholipids in cell membrane
• Storage form of body’s choline
• Widely distributed in animals in liver, brain, nerve
tissues, sperm & egg-yolk, having both meatabolic &
structural functions
• On hydrolysis: glycerol, fatty acids, phosphoric acid,
nitrogenous base choline.
Properties of lecithin
Physical properties :
• when purified it is a waxy, white substance,
becomes brown when exposed to air
• Soluble in ordinary fat
• hygroscopic
Chemical properties
Lecithin
H2O
Phosphatidic acid + Choline
1. When aqueous solution of lecithins are shake with sulphuric
acid, choline is split off, forming phosphatidic acid
Phosphatidic acid Glycerophosphoric acid +
2 Fatty acids
H2O
2.
Dipalmitoyl Lecithin
• Important phosphatidylcholine found in lungs
• Acts as a surfectant & lower the surface tension in
lung alveoli
• Absence of DPL, in premature fetus, produces
collapse of lung alveoli, which produces
Respiratory distress syndrome
Phospholipase
Lecithin
Phospholipase A2
Lysolecithin + fatty acid
Phospholipase A1
Acyl glycerophosphorylcholine
+ fatty acid
Phospholipase C
Phospholipase D
1,2 diacyl glycerol + phosphoryl choline
Phosphatidic acid + Choline
Lecithin
Lecithin
Lecithin
Cephalin
• Ethanolamine is the nitrogenous base
• They occur with lecithin, particularly rich in brain
& nervous tissue
Phosphatidyl inositol
• Phosphatidic acid is esterified to inositol
• Important component of cell membrane
• Plays vital role in the mediation of hormone
action
• Inositol as a constituent of phospholipids was
first discovered in acid fast bacilli, later in brain
& nervous tissue
Phosphatidyl serine
• Cephalin like phospholipid
• Contains amino acid serine in place of
ethanolamine
• Found in brain, nervous tissue & blood
Plasmalogens
• When a fatty acid is attached by an ether linkage at C1 of glycerol in
glycerophospholipid, the resultant compound is plasmalogen
• Unsaturated fatty acid occurs at C1
Cardiolipin
• Isolated from heart muscle
• Consists of two molecules of phosphatidic acid held
by an additional glycerol through phosphate groups
• Important component of inner mitochondrial
membrane
• It is only phosphoglyceride that possesses antigenic
properties
Sphingophospholipids
• Found in brain & nervous tissue, small amount in other tissues
• Does not contain glycerol
• In place of glycerol, it contains an 18 carbon unsaturated
amino alcohol called sphingosine (sphingol)
• On hydrolysis: sphingomyelin yields: one molecules of fatty
acid, phosphoric acid, 1 complex unsaturated amino alcohol
sphingosine
• Sphingosine is attached by an amide linkage to a fatty acid to
produce ceramide
Example: Sphingomyelins
Function of phospholipids
• Structural components of membranes and regulate
membrane permeability
• Role in enzyme action e.g. mitochondrial enzyme
system involved in oxidative phosphorylation
• Role in transport of lipids from intestines
• Role in lipid absorption in intestine
• Role in electron transport
Cont…
• Lipotropic action of lecithin
• Membrane phospholipids as source of arachidonic acid
• Role in blood coagulation
• Insulation: phospholipids of myelin sheath provide the
insulation around the nerve
• Cofactor e.g. lipoptotein lipase, triacylglycerol lipase
• Phosphatidylinositol are involved in signal transmission
across membranes
Glycolipids
1. Cerebrosides (Glycosphingosides)
2. Gangliosides
3. Sulfolipids
Cerebrosides (glycosphingosides)
• Occur large amounts in the white matter of brain & in the
myelin sheaths of nerve
• Structure: no glycerol, no phosphoric acid & no nitrogenous
base. Thus, cerabrosides on hydrolysis yields:
- a sugar, usually galactose but sometimes glucose
- a high mol. Weight fatty acid
- alcohol, sphingosine or dihydrosphingosine
• Contain a ceramide (sphingosine attached to fatty acid) &
one or more sugars
Cont..
• Ceramide + Glucose : Glucocerebroside
• Ceramide + Galactose: Galactocerebroside
Types of cerebrosides:
1. Kerasin
2. Cerebron
3. Nervon
4. Oxynervon
• Function: Nerve conduction in myelin sheath
Clinical aspect of cerebrosides
Gaucher’s disease:
• Inherited disorder of cerebrosides metabolism
• Autosomal recessive
• Enzyme defect: deficiency of beta
glucocerebrosidase
Gangliosides
• Highest concentration found in gray matter of the brain
• Formed when ceramide oligo-sachharides have at least
one molecules of NANA (N-acetyl neuraminic acid, also
called sialic acid) attached to them
• Ceramide-Glucose-Galactose-NANA
• Types of gangliosides: more than 30 types have been
isolated
• Four important types: GM-1, GM-2, GM-3 & GD-3
Function: can serve as specific membrane binding sites
(receptor sites) for circulating hormones
Clinical aspect
1. Tay-Sach’s disease (GM2 Gangliosidosis)
• Enzyme defect: deficiency of hexosaminidase A
2. GM1 Gangliosidosis
• Due to deficiency of beta galactosidase
Sulfolipids
• Formed when sulfate groups are attached to
ceramide oligosaccharides
• Important component of membranes of nervous
tissue
• Failure in degradation of these compounds results
in accumulation of these complex in CNS, result
in lipid storage diseases
Clinical aspect
1. Metachromatic Leukodystrophy
• Enzyme deficiency: sulfatase
2. Fabry’s disease
• Enzyme deficiency: alpha galactosidase
3. Krabbe’s disease
• Enzyme deficiency: galactocerebrosidase

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compound lipids.ppt

  • 1. Complex lipids • Classification • Structure & function of phospholipids & glycolipids 12-10-2011
  • 3. Phospholipids • Complex lipids • Containing phosphoric acid, in addition to fatty acids, nitrogenous base and alcohol Classification Phospholipids Glycerophospholipids Sphingophospholipids
  • 4. Micelles are spherical structures that have a nonpolar, hydrophobic environment in the core, and a polar, aqueous environment on the surface. The bile salt-lipid complexes formed in the small intestine are micelles.
  • 6.
  • 8. Phosphatidyl choline (Lecithin) • Most abundant phospholipids in cell membrane • Storage form of body’s choline • Widely distributed in animals in liver, brain, nerve tissues, sperm & egg-yolk, having both meatabolic & structural functions • On hydrolysis: glycerol, fatty acids, phosphoric acid, nitrogenous base choline.
  • 9. Properties of lecithin Physical properties : • when purified it is a waxy, white substance, becomes brown when exposed to air • Soluble in ordinary fat • hygroscopic
  • 10. Chemical properties Lecithin H2O Phosphatidic acid + Choline 1. When aqueous solution of lecithins are shake with sulphuric acid, choline is split off, forming phosphatidic acid Phosphatidic acid Glycerophosphoric acid + 2 Fatty acids H2O 2.
  • 11. Dipalmitoyl Lecithin • Important phosphatidylcholine found in lungs • Acts as a surfectant & lower the surface tension in lung alveoli • Absence of DPL, in premature fetus, produces collapse of lung alveoli, which produces Respiratory distress syndrome
  • 12. Phospholipase Lecithin Phospholipase A2 Lysolecithin + fatty acid Phospholipase A1 Acyl glycerophosphorylcholine + fatty acid Phospholipase C Phospholipase D 1,2 diacyl glycerol + phosphoryl choline Phosphatidic acid + Choline Lecithin Lecithin Lecithin
  • 13. Cephalin • Ethanolamine is the nitrogenous base • They occur with lecithin, particularly rich in brain & nervous tissue
  • 14. Phosphatidyl inositol • Phosphatidic acid is esterified to inositol • Important component of cell membrane • Plays vital role in the mediation of hormone action • Inositol as a constituent of phospholipids was first discovered in acid fast bacilli, later in brain & nervous tissue
  • 15. Phosphatidyl serine • Cephalin like phospholipid • Contains amino acid serine in place of ethanolamine • Found in brain, nervous tissue & blood
  • 16. Plasmalogens • When a fatty acid is attached by an ether linkage at C1 of glycerol in glycerophospholipid, the resultant compound is plasmalogen • Unsaturated fatty acid occurs at C1
  • 17. Cardiolipin • Isolated from heart muscle • Consists of two molecules of phosphatidic acid held by an additional glycerol through phosphate groups • Important component of inner mitochondrial membrane • It is only phosphoglyceride that possesses antigenic properties
  • 18. Sphingophospholipids • Found in brain & nervous tissue, small amount in other tissues • Does not contain glycerol • In place of glycerol, it contains an 18 carbon unsaturated amino alcohol called sphingosine (sphingol) • On hydrolysis: sphingomyelin yields: one molecules of fatty acid, phosphoric acid, 1 complex unsaturated amino alcohol sphingosine • Sphingosine is attached by an amide linkage to a fatty acid to produce ceramide Example: Sphingomyelins
  • 19.
  • 20. Function of phospholipids • Structural components of membranes and regulate membrane permeability • Role in enzyme action e.g. mitochondrial enzyme system involved in oxidative phosphorylation • Role in transport of lipids from intestines • Role in lipid absorption in intestine • Role in electron transport
  • 21. Cont… • Lipotropic action of lecithin • Membrane phospholipids as source of arachidonic acid • Role in blood coagulation • Insulation: phospholipids of myelin sheath provide the insulation around the nerve • Cofactor e.g. lipoptotein lipase, triacylglycerol lipase • Phosphatidylinositol are involved in signal transmission across membranes
  • 23. Cerebrosides (glycosphingosides) • Occur large amounts in the white matter of brain & in the myelin sheaths of nerve • Structure: no glycerol, no phosphoric acid & no nitrogenous base. Thus, cerabrosides on hydrolysis yields: - a sugar, usually galactose but sometimes glucose - a high mol. Weight fatty acid - alcohol, sphingosine or dihydrosphingosine • Contain a ceramide (sphingosine attached to fatty acid) & one or more sugars
  • 24. Cont.. • Ceramide + Glucose : Glucocerebroside • Ceramide + Galactose: Galactocerebroside Types of cerebrosides: 1. Kerasin 2. Cerebron 3. Nervon 4. Oxynervon • Function: Nerve conduction in myelin sheath
  • 25. Clinical aspect of cerebrosides Gaucher’s disease: • Inherited disorder of cerebrosides metabolism • Autosomal recessive • Enzyme defect: deficiency of beta glucocerebrosidase
  • 26. Gangliosides • Highest concentration found in gray matter of the brain • Formed when ceramide oligo-sachharides have at least one molecules of NANA (N-acetyl neuraminic acid, also called sialic acid) attached to them • Ceramide-Glucose-Galactose-NANA • Types of gangliosides: more than 30 types have been isolated • Four important types: GM-1, GM-2, GM-3 & GD-3
  • 27. Function: can serve as specific membrane binding sites (receptor sites) for circulating hormones Clinical aspect 1. Tay-Sach’s disease (GM2 Gangliosidosis) • Enzyme defect: deficiency of hexosaminidase A 2. GM1 Gangliosidosis • Due to deficiency of beta galactosidase
  • 28. Sulfolipids • Formed when sulfate groups are attached to ceramide oligosaccharides • Important component of membranes of nervous tissue • Failure in degradation of these compounds results in accumulation of these complex in CNS, result in lipid storage diseases
  • 29. Clinical aspect 1. Metachromatic Leukodystrophy • Enzyme deficiency: sulfatase 2. Fabry’s disease • Enzyme deficiency: alpha galactosidase 3. Krabbe’s disease • Enzyme deficiency: galactocerebrosidase