Name: Hussein Ammar Mohsen

University of Baghdad: Khwarazmi College of Engineering

Department: Automated Manufacturing Engineering

Lipids
• Are heterogeneous group of compounds
(fats, oils, steroids, waxes and related
compounds), that are related more by
their physical than by their chemical
properties.
• Common properties
▫ (1)Relatively insoluble in water
▫ (2) Soluble in non-polar solvents
Properties of Lipids
• Greasy to touch, leaves a permanent oily stain on
paper;
• Lighter than water
• Soluble in organic solvent, insoluble in water
• When pure, colorless with bland odor and taste
• Yellow color in fat is due to carotene
(provitamin A)
• When heated strongly, undergoes decomposition
forming acrid flammable vapors and when
ignited, they burn with a sooty flame.
LIPIDS
• Important dietary constituents
▫ High energy value
▫ Contains fat-soluble vitamins and essential fatty
acids
▫ Essential Fatty Acids (EFA’s)
🞄 Are necessary fats that humans cannot synthesize,
and must be obtained through diet.
🞄 Are long-chain polyunsaturated fatty acids derived
from linolenic, linoleic, and oleic acids
 Biomedical Importance
• Fat stored in adipose tissue serves as thermal
insulator in the subcutaneous tissues and
around certain organs;
• Nonpolar lipids act as electrical insulator,
allowing rapid propagation of depolarization
waves along myelinated nerves;
• Lipoproteins occur in both cell membrane and
mitochondria, and also serve to transport lipid
in the blood.
Major Roles of
Biological Lipids
• They serve as structural components of
biological membranes;
• They provide energy reserves, predominantly
in the form of triacylglycerols;
• Both lipids and lipid derivatives serve as
vitamins and hormones; and
• Lipophilic bile acids aid in lipid
solubilization.
 IMPORTANCE OF LIPID
BIOCHEMISTRY
• Obesity, Diabetes mellitus,
Atherosclerosis
• Role of various polyunsaturated fatty
acids in nutrition and health
 Classification of Lipids
• Simple lipid
▫ Ester of fatty acid and __
▫ Fats/fixed oil - ester of fatty acid and
🞄 Triglycerides - esters of three molecules of fatty acids
plus one molecule of glycerol
🞄 Found in adipose tissue, butterfat, lard, suet, fish
oils, olive oil, corn oil
▫ Waxes - ester of fatty acid and __
🞄 beeswax, head oil of sperm whale, cerumen,
carnauba oil, and lanolin
 Classification of Lipids
• Compound Lipid
▫ Esters of fatty acid, alcohol and another
compound.
▫ A. PHOSPHOLIPIDS
🞄 Fatty acid and alcohol plus a
residue;
🞄 Frequently have nitrogen-containing bases
and other substituents
(glycerophospholipids, the alcohol is
; sphingophospholipids, the
alcohol is ).
Classification of Lipids
▫ B. GLYCOLIPIDS
🞄 Glycosphingolipids
🞄 fatty acid and sphingosine plus
carbohydrate.

▫ C. OTHER COMPLEX LIPIDS

🞄 sulfolipids and aminolipids
🞄 lipoproteins
Derived Lipid – product of simple
and compound lipid upon hydrolysis.
• Fatty acids • Glycerol
▫ occur in plant and • Steroids
animal foods • Other alcohols
▫ also exhibit in complex • Fatty aldehydes
forms with other • Ketone bodies
substances
▫ obtained from • Hydrocarbons, Lipid-
hydrolysis of fats soluble vitamins
▫ usually contains an • Hormones
even number of carbon * Acylglycerols, cholesterol, and
atoms and are straight cholesteryl ester are
chain derivatives uncharged, so are termed
NEUTRAL LIPIDS
 Fatty Acids
• Are aliphatic carboxylic acids
• Occur mainly as esters of natural fats and oils
but do occur in the unesterified form as free fatty
acids ( transport form found in the plasma)
• In natural fats, they are usually straight-chain
derivatives containing an even number of carbon
atoms.
🞄 SATURATED – no double bonds
🞄 UNSATURATED – containing one or more double
bonds
 Fatty Acids
• Saturated fatty acids: CnH2nO2
• Unsaturated fatty acids: CnH2n - (2x #db) O2
Structure of Fatty Acids
Structure of Fatty Acids
Structure of Fatty Acids
 Geometric isomerism in
unsaturated fatty acid
• cis
▫ The acyl chain are on
the same side of the
bond
▫ Oleic acid
• trans
▫ The acyl chain is on the
opposite side
▫ Elaidic acid
 NOMENCLATURE
• Named after the corresponding hydrocarbons
with the same number and arrangement of
carbon atoms, with-oic being substituted for the
final –e :
▫ –anoic – saturated acid ends (e.g.,octanoic acid)
▫ –enoic – unsaturated acids with double bonds
(e.g., octadecenoic acid)
• C atoms are numbered from the carboxyl C as C-
1
 NOMENCLATURE
• Adjacent to carboxyl C as 2, 3 and 4 are also
known as , , and  carbons, respectively
• Terminal methyl C is known as  or n-carbon
•  is used conventionally to indicate the number
and position of the double bond, eg., 9, double
bond between C-9 and C-10
 SATURATED FATTY ACIDS
COMMON # OF C
NAME ATOMS

Acetic 2 Major end product of carbohydrate

fermentation by rumen organism
Butyric 4 ⚫ Incertain fats in small amounts (butter)
⚫ End product of carbohydrate fermentation
Valeric 5
by rumen organisms
Caproic 6

Lauric 12 Spermaceti, cinnamon, palm kernel, coconut

oils, laurels, butter

Myristic 14 Nutmeg, palm kernel, coconut oils, myrtles,

butter
Palmitic 16 Common in all animal and plant
Stearic 18
UNSATURATED FATTY ACIDS
• MONOUNSATURATED (Monoethenoid,
monoenoic) acids containing double bond
• POLYUNSATURATED (polyethenoid, polyenoic)
acids containing two or more double bonds
• EICOSANOIDS
▫ Derived from eicosa (20 carbon) polyenoic fatty acids
▫ Arachidonic acid is the major precursors
🞄 Prostanoids
🞄 Leukotrienes (LTs )
🞄 Lipoxins (LXs)
 PROSTANOIDS
• Are part of a family of biologically active lipids
derived from the twenty-carbon essential fatty
acids or eicosanoids;
• Relates to the products of the cyclooxygenase
pathway
• Prostanoic acid as the central structural element
• Three main groups
▫ Prostaglandins (PGs)
▫ Prostacyclins (PGIs)
▫ Thromboxanes (TXs)
 PROSTAglandins
• Acts as local hormones
• Synthesized from eicosanoic polyunsaturated
fatty acids (arachidonic acid) to form
cyclopentane ring
• PG1, PG2, and PG3– numbers are based on the
double bonds in the side chain
• The letter component identifies the functional
groups of the cyclopentane ring
▫ PGE – keto group in 9 position
▫ PGF – hydroxyl group in 9 position
 THROMBOXANES
• Cyclopentane ring
interrupted with an
oxygen atom;
• The two major
thromboxanes are
thromboxane A2 and
thromboxane B2
• Its role is in clot formation
(thrombosis)
LEUKOTRIENES and LIPOXINS
• Formed via the lipooxygenase pathway
• Has three (leukotrienes) to four (lipoxins)
conjugated double bonds
• Leukotrienes - a proinflammatory agents and
causes bronchoconstriction, thus play a part in
asthma
▫ Common leukotriene inhibitors
🞄 Zyflo – Zileuton
🞄 Accolate – Zarfirlukast
🞄 Singulair - Montelukast
 PHYSICAL and PHYSIOLOGIC
PROPERTIES OF FATTY ACIDS
• MELTING POINT of even numbered carbon fatty
acids;
▫ increases with chain length
▫ decreases according to unsaturation
• TRIACYLGLYCEROL containing three saturated
fatty acids of 12 C or more is solid at body
temperature
▫ 18:2 fatty residues are liquid at body temperature to
below 0°C
• MEMBRANE LIPIDS – must be fluid at all
environmental conditions
▫ More unsaturated than storage lipids
 TRIACYLGLYCEROLS
(TRIGLYCERIDES)
• Main storage forms of fatty acids
• They are formed by esterification of glycerol with
three fatty acids
• Depending on the content of unsaturated fatty
acids, triglycerides can be solids (fats) or liquids
(oils)
▫ Oils have highly unsaturated fatty acid chains and
are liquid at room temperature
• Main lipid constituents
of membrane
• Derivatives of
phosphatidic acid
• Phosphate is esterified
with the –OH of a
suitable alcohol
• Phosphatidic acid –
intermediate in the
synthesis of
triacylglycerols
PHOSPHATIDYLCHOLINE
(Lecithin)
• Phosphoacylglycerol
containing choline
• Most abundant phospholipids
of the cell membrane and
represent a large proportion of
the body’s store of choline
• CHOLINE – important in
nervous transmission, as
acetylcholine, and as a store of
labile methyl group
 DIPALMITOYL LECITHIN
• Major constituent of the surfactant preventing
adherence, due to surface tension, of the inner
surfaces of the lungs.
• Absence from the lungs of premature infants
causes respiratory distress syndrome
 PHOSPHATIDYLETHANOLAMINE
(Cephalin)
• Ethanolamine replaces choline
• A lipid found in biological
membranes
• Cephalin is found particularly
in nervous tissue such as the
white matter of brain, nerves,
neural tissue, and in spinal
cord
• Cephalin is the principal
phospholipid in bacteria.
 PHOSPHATIDYLSERINE
• Serine replaces choline
• Found in most tissues
• US-FDA “qualified claim”
states that;
▫ "Consumption of
phosphatidylserine may
reduce the risk of dementia
in the elderly" and;
▫ "Consumption of
phosphatidylserine may
reduce the risk of cognitive
dysfunction in the elderly".
PHOSPHATIDYLINOSITOL

• Precursor of second messenger

• Inositol is present as stereoisomer, myoinositol
• Phosphatidylinositol 4,5-biphosphate important
constituent of the cell membrane phospholipids
and cleaved into diacylglycerol and inositol
triphosphate (internal signals or second
messenger)
 CARDIOLIPIN
• bisphosphatidyl glycerol
• Is an important component of the inner
mitochondrial membrane, where it constitutes
about 20% of the total lipid
• It serves as an insulator and stabilizes the
activity of protein complexes important to the
electron transport chain
 LYSOPHOSPHOLIPIDS
• Are intermediates in the metabolism of
phosphoglycerols
• Important in the metabolism and
interconversions of phospholipids
(lysophosphatidylcholine)
• Found in oxidized lipoproteins and can
promote atheroschlerosis
 PLASMALOGENS
• 10% of the phospholipids
of the brain and muscle
• Resemble
phosphatidylethanolamine
(ether linked)
• Alkyl radical is an
unsaturated alcohol
• Choline, serine or inositol
---- may be substituted for
ethanolamine
 SPHINGOMYELINS
• Found in large quantities in brain and nerve
tissues
• Yields fatty acid, phosphoric acid, choline, and
a complex amino alcohol, sphingosine

SPHINGOSINE
(the atoms in red are derived from glycerol)
 CERAMIDE
• Sphingosine plus amino acid
• Structure found in glycosphingolipids

"n" indicates any fatty acid

may be N-acetylated at this
position
 GLYCOLIPIDS
(GLYCOSPHINGOLIPIDS)
• Distributed in every tissue of the body
▫ Nervous tissues (brain)
▫ Plasma membrane – cell surface carbohydrates
• Glycosphingolipids
▫ Major glycolipids in animal tissues
▫ Ceramide + sugar
• GALACTOSYLCERAMIDE
▫ Major sphingolipid of brain & other nervous
tissue, C24 fatty acids
 GLYCOLIPIDS
(GLYCOSPHINGOLIPIDS)
• GANGLIOSIDES
▫ Are complex glycosphingolipids derived from
glucosylceramide that contain in addition one or
more molecules of a sialic acid
• NEURAMINIC ACID – principal sialic acid
found in human tissues.
• GM3 – contains ceramide, one molecule of
glucose, one molecule of galactose and one
molecule of NeuAc
▫ The simplest gangliosides in tissues
 STEROIDS

Phenanthrene
rings

Cyclopentane ring

• This nucleus, partially or completely

hydrogenated, is generally substituted by
methyl groups at C10 and C13.
• A chemical group (ketone, hydroxyl...) or an
alkyl side-chain may also be present at C17
 47

Steroids
•The carbon skeleton
of steroids is bent to
form 4 fused rings
Cholesterol

Cholesterol is
the “base Estrogen
steroid” from Testosterone

which your body

produces other
steroids
Estrogen & testosterone are also steroids
 CHOLESTEROL
• Associated with atherosclerosis & heart disease
• Biochemical significance
▫ Precursor of bile acids, adrenocortical hormones, sex
hormones, Vit. D, cardiac glycosides, sitosterols and
alkaloids
• Major constituent of the plasma membrane and of
plasma lipoproteins
• Cholesteryl ester
▫ – OH at 3 position is esterified with long chain fatty
acid
▫ Occurs in animals but not in bacteria
 ERGOSTEROL
• Precursor of vitamin D2
• Occurs in plants and yeast
• It is turned into viosterol by UV light, and is then
converted into ergocalciferol (a form of Vitamin
D)
• Acquires antirachitic properties when irradiated
with UV light
• A component of fungal cell membranes, serving
the same function that cholesterol serves in
animal cells
 POLYPRENOIDS
• Not steroids, but synthesized like cholesterol
• UBIQUINONE- participates in respiratory chain
in mitochondrion
• DOLICHOL - takes part in glycoprotein
synthesis by transferring carbohydrate residues
to asparagine residues of polypeptide
• ISOPRENOID – rubber, camphor, fat soluble-
Vit A, D, E & K and -carotene (provitamin A)
 LIPID PEROXIDATION

• Lipids exposed to oxygen (Auto-oxidation)

• A chain reaction providing a continuous supply
of free radicals
• Effects of peroxidation include:
▫ deterioration of food (rancidity)
▫ damage of tissue (cancer, inflammation,
atheroschlerosis and aging) caused by free radicals
containing methylene-interrupted double bonds
 PEROXIDATION
• Catalyzed in vivo by heme compounds and
by lipoxygenases (platelets and
leukocytes)
• Other products of auto-oxidation (or
enzymatic oxidation) of physiologic
importance include;
▫ Oxysterols – formed from cholesterol
▫ Isoprostanes - prostanoids
 ANTIOXIDANTS
• Control and reduce lipid peroxidation
• Antioxidants for food are propyl gallate,
BHA, BHT
• Naturally occuring antioxidants include;
▫ Vitamin E (tocopherol) is lipid soluble
▫ Vitamin C and urate are water soluble
▫ Beta-carotene
 CLASSES OF ANTIOXIDANTS

🞄 i. Preventive antioxidants – reduce the rate of

chain initiation
▫ Catalases and Peroxidases
▫ - gluthathione peroxidase (reacts with ROOH)
▫ Selenium
▫ EDTA, DTPA (Chelators of metal ions)
🞄 ii. Chain-breaking antioxidants – interfere with
chain propagation
▫ Superoxide dismutase – trap superoxide free radicals
▫ Urate
▫ Vitamin E – lipid phase trap ROO radicals
 AMPHIPHATIC LIPIDS
• Contain predominantly nonpolar groups plus a
polar group
• Molecule is partly hydrophobic and hydrophilic
• Include fatty acids, phospholipids,
sphingolipids, bile salts, and cholesterol
• Oriented at oil:water interfaces with the polar
group in water phase and the nonpolar group in
the oil phase
• Basic structure of biologic membranes (bilayer)
 AMPHIPHATIC LIPIDS
• MICELLES
▫ Formed when critical concentration
of amphiphatic lipids is present in
aqueous medium
• LIPOSOMES
▫ Formed by sonicating an
amphiphatic lipid in an aqueous
medium
▫ Useful as carriers of drugs in
circulation, targeted to specific
organs, eg, in cancer therapy
▫ Also used for gene transfer into
vascular cells
▫ Carriers for topical and
transdermal delivery of drugs and
cosmetics
 Body’s main
fuel reserve

Source of
fatty acid
2

1
Acetoacetate and 3-
hydroxybutyrate – important
fuels in prolonged fasting
 Triacylglycerols
(fats)
Steroids

Esterification
Lipolysis

Steroidogenesis
Fatty acids

Lipogenesis
Β-oxidation
Cholesterol
Carbohydrates Cholesterologenesis
Acetyl CoA
Amino acids Ketogenesis
CO2
Ketone bodies
Citric acid
cycle