Biochemistry

Lipids
Family of Lipids
Lipids
 Lipids: family of biochemicals that are soluble
in non-polar organic solvents
(hexane,ether,benzene) but not in water.
 Classes:
 Waxes: fatty acid + a long-chain alcohol
 Triglycerides (fats & oils): glycerol + 3 fatty acids
 Phospholipids: glycerol + 2 fatty acids + phosphate + amino
alcohol
 Glycolipids: glycerol or spinogosine + fatty acid +
monosaccharide
 Steroids: 3 cyclohexanes + 1 cyclopentane fused together
CLASSIFICATION
 Based on biochemical function:
 1. Energy-storage lipids (triacylglycerols)
 2. Membrane lipids (phospholipids,
sphingoglycolipids, and cholesterol)
 3. Emulsification lipids (bile acids)
 4. Messenger lipids (steroid hormones and
eicosanoids)
 5. Protective-coating lipids (biological waxes)
CLASSIFICATION
 Based upon whether or not saponification
occurs when lipid is placed in basic
aqueous solution:
 1. Saponifiable lipids (triacylglycerols,
phospholipids, sphingoglycolipids, and
biological waxes)
 2. Nonsaponifiable lipids (cholesterol,
steroid hormones, bile acids, and
eicosanoids)
ENERGY STORAGE LIPIDS
 Triacylglycerol/Triglycerides – a lipid
formed by esterification of three fatty acids
to a glycerol molecule.
 Concentrated in adipocytes (cells)
 Adipose tissues – under the skin, abdominal
cavity, mammary glands, various organs
 Glycerol + 3 fatty acids
Fatty Acids
 Fatty acids: monocarboxylic acids
 Form fats and oils (usually have an even
number of carbons)
 Saturated fatty acid: all single bonds
 Unsaturated fatty acid: at least 1 double
bond (monounsaturated)
 Polyunsaturated: two or more double bonds
 Most double bonds are cis- bonds that cause a bend in
the chain
Fatty Acids
 Short-chain fatty acids: C4 and C6
 Medium-chain fatty acids: C8 and
C10
 Long-chain fatty acids: C12 and C24
Saturated Fatty Acids (BAD)
 2C – acetic acid (water soluble)
 4C – butyric acid (water soluble)
 6C – caproic acid
 8C – caprylic acid
 10C – capric acid
 12C – lauric acid
 14C – myristic acid
 16C – palmitic acid (most abundant in humans)
 18C – stearic acid
 20C – arachidic acid
 HCO2H FORMIC ACID L. FORMICA “ANT”

 CH3CO2H ACETIC ACID L. ACETUM “VINEGAR”

 CH3CH2CO2H PROPIONIC ACID GR. PROTO “FIRST”; PION “FAT”

 CH3(CH2)2CO2H BUTYRIC ACID L. BUTYRUM “BUTTER”

 CH3(CH2)3CO2H VALERIC ACID L. VALERE “TO BE STRONG”

 CH3(CH2)4CO2H CAPROIC ACID L. CAPER “GOAT“

 CH3(CH2)5CO2H ENANTHIC G. OINANTH “VINE BLOSSOM“

 CH3(CH2)6CO2H CAPRYLIC ACID L. CAPER “GOAT“

 CH3(CH2)7CO2H PELARGONIC PELARGONIUM PLANT

 CH3(CH2)8CO2H CAPRIC ACID L. CAPER “GOAT“

Monounsaturated Fatty Acids (GOOD)
 Palmitoleic acid (16:1 9)
 Oleic acid (18:1 9)

Polyunsaturated Fatty Acids (BOTH)

 Linoleic acid (18:2 9,12) 6 (essential)
 Linolenic acid (18:3 9,12,15) 3 (essential)
 Arachidonic acid (20:4 5,8,11,14) 6
 EPA (eicosapentaenoic) (20:5 5,8,11,14,17) 3
 DHA (docosahexaenoic) (22:6 4,7,10,13,16,19) 3
Linolenic acid (18:3 9,12,15) 3
Linoleic acid (18:2 9,12) 6

COOH

COOH
Fatty Acids
Fatty Acids
 Properties
 Saturated fatty acids are solid at room
temperature and have a high melting point
 Unsaturated fatty acids are liquid at room
temperature and have a low melting point
Fatty Acids
Fatty Acids with Starch
Fatty Acids in the Human body
 Essential fatty acids: polyunsaturated fatty
acids that the body can not make
 Important: linoleic and linolenic acids
 Lack of in infants cause skin dermatitis
 Arachidonic acid is converted into
prostaglandins which serve as local
chemical messengers
Fats and Oils
Fats and Oils
Fats and Oils

 Fats: more saturated fatty acids; solid at

room temperature (cod liver oil)
 Oils: more unsaturated fatty acids; liquid at
room temperature (theobroma oil)
Fats and Oils
Fats and Oils
 Properties:
 Hydrogenation (adding H2)
 Converts a double bond to a single bond
 Changes liquid oil to a soft semisolid fat
 Oxidation to carboxylic acid
 Fat/oil becomes “rancid” with a disagreeable odor
 Some oils have antioxidants to slow oxidation
 Refrigeration in an air-tight container slows oxidation
 Microorganisms oxidize body oils during exercise
Hydrogenation of Oils
Fats and Oils
 Properties continued:
 Saponification (basic) with heat and strong base
produces a glycerol and fatty acid salts
 Hydrolysis (acid)
 Requires a strong acid catalyst or lipase enzyme
 Produces 1 glycerol + 3 fatty acids
Hydrolysis of Fats and Oils

• The basic hydrolysis of fat and oils produces soap

(this reaction is known as saponification).
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7
MEMBRANE LIPIDS
Phospholipids
Sphingoglycolipids
Cholesterol
 The Cell Membrane

Polar Head
Phospholipid
Nonpolar Tail

Phospholipids join a bilayer

to form a cell membrane.
The Cell Membrane

Glycolipid

Phospholipids join a bilayer

to form a cell membrane.
Phospholipids
alcohol + phosphate + fatty acid

1. Glycerophospholipid: glycerol + 2 fatty

acids + phosphate/alcohol
 Lecithins and cephalins abundant in brain &
nerve tissue, egg yolks, wheat germ, and yeast
 Forms cell membranes
Phospholipids
2. Sphingophospholipid: sphingosine + 1
fatty acid + phosphate/ alcohol
 A phospholipid with sphingosine instead of the
glycerol
 Important in the myelin sheath that surrounds
most nerve fibers
Phospholipid
Phospholipid
Sphingoglycolipids
sphingosine + fatty acid + carbohydrates
Cerebrosides – contain a single
monosaccharide unit (glucose/galactose).
Present in brain and myelin sheath of nerves.
Gangliosides – branched chain of 7
monosaccharides. Present in brain and
myelin sheath of nerves.
Cholesterol
Steroids – a lipid whose structure is based
on a fused-ring system that involves three 6-
membered rings and one 5-membered ring.

cyclopentanoperhydrophenanthrene ring
egg yolks and organ meats
Steroids
Cholesterol
 Cholesterol
 Synthesized in the liver
 Gives strength to cell membranes
 In myelin sheath, bile salts, vitamin D produced
by the skin
 Excess in body leads to gall stones and plaque
in the arteries
Family of Lipids
 EMULSIFICATION
LIPIDS
Bile acids
Bile Acids
 Bile acids – cholesterol derivative that functions as a
lipid-emulsifying agent in the aqueous environment of
the digestive tract.
 Synthesized from cholesterol in the liver
 Stored in gallbladder
 Sent to the digestive tract to emulsify fats during digestion
 Promotes absorption of cholesterol in the digestive tract
 TYPES:
1. Cholic acid
2. 12- Deoxycholic acid
3. 7- Deoxycholic acid
 MESSENGER
LIPIDS
Steroidhormones
Eicosanoids
Steroid Hormones
 Hormone – biochemical substance,
produced by a ductless gland, that
has a messenger function. Serves as
communication between various
tissues.
 Steroid hormone – hormone that is
a cholesterol derivative
 Two types: Sex hormones and Adrenocorticoid
hormones
Steroid Hormones
 Sex Hormones
1. Estrogens (Estradiol) – female sex
hormone
2. Androgens (Testosterone) – male sex
hormones
3. Progestins (Progesterone) – pregnancy
hormones
 Anabolic steroid, derivative of testosterone
 Prevents breakdown of worn out muscle cells
 Has dangerous side effects
Steroid Hormones
 Adrenocorticoid Hormones

1. Mineralocorticoids – control the

balance of Na+ and K+ ions in cells and
body fluids
2. Glucocorticoids – control glucose
metabolism and counteract inflammation
Eicosanoids
 Eicosanoids – an oxygenated C20-
fatty acid derivative that functions as
messenger lipid
 Eikos – “twenty”
 Arachidonic acid (20:4 fatty acid)
 3 Types: Prostaglandins,
Thromboxanes, Leukotrienes
Eicosanoids
 Prostaglandins
 Raising body temperature
 Inhibiting the secretion of gastric juices
 Increasing the secretion of a protective mucus
layer into the stomach
 Relaxing and contracting smooth muscle
 Intensifying pain
 Enhancing inflammation responses
Prostaglandins
Eicosanoids
 Thromboxanes
 Promote the formation of blood clots

 Leukotrienes (leukocytes)
 Inflammatory and hypersensitivity (allergy)
responses
PROTECTIVE-COATING
LIPIDS
Biological waxes
Biological Waxes
 Biological Waxes – lipid that is a
monoester of a long-chain fatty acid
and a long-chain alcohol
Long chain fatty acid + Long chain alcohol

 Protects hair and skin to keep it pliable and

lubricated
 Animal fur/feathers – water repellant
Biological Waxes
 Examples
 Carnauba Wax from palm tree (automobile wax,
boat wax, floor wax, shoe wax)
 Lanolin from sheep wool (used in
creams/ointments to enhance retention of water)
 Candles
A Lipoprotein
Lipids in the Body
 Lipoproteins
 Water insoluble lipids must be delivered to all parts of the
body by the water-based blood
 Body packages lipids in membrane with proteins to make
the lipids water soluble
 Types: VLDL, LDL, HDL, chylomicrons
 HDL on the way to the liver is “good cholesterol”
 LDL on way to the cells is prone to deposit in blood
vessels
 Enzyme in blood capillaries releases lipids from the
protein carrier
The End