Lipids

Lipids of Physiologic Significance

 BIOMEDICAL IMPORTANCE
• The lipids
• The common property
– insoluble in water
– soluble in nonpolar solvents
• They are important dietary constituents
– high energy value
– fat-soluble vitamins
– essential fatty acids
• Fat is stored in adipose tissue
 BIOMEDICAL IMPORTANCE
• Thermal insulator
• electrical insulators
• cellular constituents
– Membranes
• Transport
– Lipoproteins
• Lipid biochemistry is necessary
– obesity, diabetes mellitus, atherosclerosis,
polyunsaturated fatty acids in nutrition and health
 Classification
• Simple lipids
– Esters of fatty acids with various alcohols
• Complex lipids
– groups in addition to an alcohol and a fatty acid
– Phospholipids
• Glycerophospholipids
• Sphingophospholipids
– Glycolipids
– Other complex lipids
• Sulfolipids and aminolipids
• Lipoproteins
 Classification
• Precursor and derived lipids

• Neutral lipids
– acylglycerols (glycerides),cholesterol, and
cholesteryl esters
 Free fatty
• Free fatty acids
– Saturated
• -anoic
– Unsaturated
• -enoic
• 1,2,3,…
• α, β, γ ,… ω or n carbons
• Δ
Saturated fatty acids
 Unsaturated Fatty Acids
• Monounsaturated
• Polyunsaturated
• Eicosanoids
– eicosa- (20-carbon) polyenoic fatty acids
• Prostanoids
– Prostaglandins(PGs)
– Prostacyclins (PGIs)
– Thromboxanes (TXs)
• Leukotrienes (LTs)
• Lipoxins (LXs)
 Prostaglandins
• The number of double bonds
– PG1, PG2, PG3
• Different substituent groups (on ring)
– A, B,C,etc
 The leukotrienes and
lipoxins
• Lipoxygenase pathway
• three or four conjugated double bonds
• Leukotrienes cause bronchoconstriction as
well as being potent proinflammatory agents
and play a part in asthma
 Unsaturated Fatty Acids
• Geometric isomerism
– Cis
• on the same side
– Trans
• if on opposite sides
• as a by-product of the saturation of fatty acids
• ingestion of ruminant fat
• Significance
– Molecular packing in membranes
Unsaturated fatty acids of physiologic and nutritional significance
Structure of some unsaturated fatty acids
 Physical and Physiologic Properties
of Fatty Acids
• Chain Length and Degree of Unsaturation
– even-numbered-carbon fatty acids
– The melting points
 TRIACYLGLYCEROLS (TRIGLYCERIDES)

• THE MAIN STORAGE FORMS OF FATTY ACIDS

• Mono- and diacylglycerols
 PHOSPHOLIPIDS
• MAIN LIPID CONSTITUENTS OF MEMBRANES
• derivatives of phosphatidic acid

• Phosphatidylcholines (Lecithins)
• the most abundant phospholipids of the cell
membrane
• represent a large proportion of the body’s
store of choline
 PHOSPHOLIPIDS
• Surfactant
– Dipalmitoyl lecithin
• respiratory distress syndrome
• Phosphatidylethanolamine (cephalin)
• Phosphatidylserine
• Phosphatidylinositol
• Cardiolipin
• Lysophospholipids
 Phospholipids
• Plasmalogens
Sphingomyelins
 GLYCOLIPIDS
• GLYCOSPHINGOLIPIDS
– NERVE TISSUES
– CELL MEMBRANE
• Galactosylceramide
– Sulfatide
• Sulfogalactosylceramide
• Glucosylceramide
– Glycosphingolipid of extraneural tissues
• Simple glycosphingolipids
• Complex glycosphingolipids
– Gangliosides
• Sialic acid
• The simplest ganglioside found in tissues is GM3
• Functions
– Receptor, …
 STEROIDS
• Cholesterol
– Atherosclerosis
– As Precursor

• Sterol
– Has one or more hydroxyl
groups and no carbonyl or
carboxyl groups
• Stereoisomers
– “Chair” or a “boat” form
– The rings can be either cis or trans
– β bonds
• above the plane of the rings
– α bonds
• bonds attaching groups below
an all-trans configuration between adjacent rings
a cis configuration between rings A and B
 Cholesterol
• Cholesteryl ester
 Ergosterol
• Precursor of Vitamin D
 Polyprenoids
• Synthesized from five-carbon isoprene units
• Include
– Ubiquinone
– Dolichol
– Vitamins
• A, D, E, and K, and β-carotene (provitamin A)
 LIPID PEROXIDATION
• A SOURCE OF FREE RADICALS
– Lipids exposed to oxygen
– deterioration of foods (rancidity)
– damage to tissues
• Cancer, inflammatory diseases, atherosclerosis, and aging
– Peroxide formation from fatty acids containing
methylene-interrupted double bonds
– Antioxidants
• Vitamin E, Beta-carotene
• Urate and vitamin C
 AMPHIPATHIC LIPIDS
• Form
– Membranes, Micelles, Liposomes, & Emulsions
• Contain polar groups
– Fatty acids, phospholipids, sphingolipids, bile salts,
and, to a lesser extent, cholesterol
• Part of the molecule is hydrophobic, and part
is hydrophilic
• Micelles
– When a critical concentration of these lipids is
present in an aqueous medium
– Facilitating absorption of lipids
• Liposomes
– Formed by sonicating an amphipathic lipid in an
aqueous medium
– as carriers of drugs
• Emulsions
– Much larger particles
 Waxes
• Serve as
– Energy Stores and Water Repellents
• Esters of long-chain (C14 to C36) saturated and
unsaturated fatty acids with long-chain (C16 to
C30) alcohols
• Their melting points (60 to 100 °C) are
generally higher than those of triacylglycerols
• Triacontanoylpalmitate, the major component
of beeswax