Lipids

Part 1: Lipid Characteristics

• Lipid = a compound that is insoluble in water,
but soluble in an organic solvent (e.g., ether,
benzene, acetone, chloroform)
• “lipid” is synonymous with “fat”, but also
includes phospholipids, sterols, etc.
• chemical structure: glycerol + fatty acids
Lipid Molecule
 Nutritional Uses of Lipids
• We already know that lipids are concentrated sources of
energy (9.45 kcal/g)

• other functions:

• 1) provide means whereby fat-soluble nutrients (e.g.,

sterols, vitamins) can be absorbed by the body
• 2) structural element of cell, subcellular components
• 3) components of hormones and precursors for
prostaglandin synthesis
 Lipid Classes
• simple: FA’s esterified with glycerol
• compound: same as simple, but with other compounds also
attached
• phospholipids: fats containing phosphoric acid and nitrogen
(lecithin)
• glycolipids: FA’s compounded with CHO, but no N
• derived lipids: substances from the above derived by
hydrolysis
• sterols: large molecular wt. alcohols found in nature and
combined w/FA’s (e.g., cholesterol)
 Saturated vs. Unsaturated Fatty Acids

• saturated: the SFA’s of a lipid have no double bonds

between carbons in chain
• polyunsaturated: more than one double bond in the
chain
• most common polyunsaturated fats contain the
polyunsaturated fatty acids (PUFAs) oleic, linoleic and
linolenic acid
• unsaturated fats have lower melting points
• stearic (SFA) melts at 70oC, oleic (PUFA) at 26oC
 Fatty Acids Commonly Found in Lipids

Sat. Fatty Acids Formula Melting Point (oC)

Butyric C4H8O2 Liquid
Palmitic C16H22O2 63
Stearic C18H36O2 70
Unsat. Fatty Acids Formula Melting Point (oC)
Oleic C18H34O2 Liquid
Linoleic C18H32O2 Liquid
Linolenic C18H30O2 Liquid
 Saturated vs. Unsaturated Fats
• saturated fats tightly packed, clog arteries as atherosclerosis

• because of double bonds, polyunsaturated fats do not pack

well -- like building a wall with bricks (sat.) vs. irregular-
shaped objects (unsat.)

• plant fats are much higher in PUFA’s than animal fats

Saturated vs. Unsaturated FA’s Plant vs.
Animal Fat
corn soy tallow lard
Sat. FA’s
Myristic 3
Palmitic 7.0 8.5 27 32.2
Stearic 2.4 3.5 21 7.8

Unsat. FA’s
Oleic 45.6 17 40 48
Linoleic 45.0 54.4 2 11
Linolenic 7.1 0.5 0.6
Arachid.
 Lipid Digestion/Absorption
• Fats serve a structural function in cells, as sources of
energy, and insulation
• the poor water solubility of lipids presents a problem for
digestion: substrates are not easily accessible to digestive
enzymes
• even if hydrolyzed, the products tend to aggregate to
larger complexes that make poor contact with the cell
surface and aren’t easily absorbed
• to overcome these problems, changes in the physical
state of lipids are connected to chemical changes during
digestion and absorption
 Lipid Digestion/Absorption
Five different phases:
 hydrolysis of triglycerides (TG) to free fatty acids (FFA) and
monoacylglycerols
 solubilization of FFA and monoacylglycerols by detergents
(bile acids) and transportation from the intestinal lumen
toward the cell surface
 uptake of FFA and monoacylglycerols into the cell and
resynthesis to triglyceride
 packaging of TG’s into chylomicrons
 exocytosis of chylomicrons into lymph
 Enzymes Involved in Digestion of Lipids

• lingual lipase: provides a stable interface with

aqueous environment of stomach
• pancreatic lipase: major enzyme affecting
triglyceride hydrolysis
• colipase: protein anchoring lipase to the lipid
• lipid esterase: secreted by pancreas, acts on
cholestrol esters, activated by bile
• phospholipases: cleave phospholipids, activated by
trypsin
 What about Bile???
• These are biological detergents synthesized by the liver and
secreted into the intestine
• they form the spherical structures (micelles) assisting in
absorption
• hydrophobic portion (tails of FA) are located to the inside of the
micelle, with heads (hydrophillic portion) to the outside
• they move lipids from the intestinal lumen to the cell surface
• absorption is by diffusion (complete for FA and monoglycerides,
less for others)
 Factors Affecting Absorption of Lipids

• amount of fat consumed (fat=digestion=absorption)

• age of subject ( age =  digestion)
• emulsifying agents ( digestion =  absorption)
• chain length of FA’s (> 18C =  digestibility)
• degree of saturation of FA ( sat =  digestibility)
• overheating and autooxidation (rancidification (rot) at double
bond)
• optimal dietary calcium = optimal FA absorption (high Ca = 
absorption)
 Lipid Metabolism/Absorption

• short chain FA’s are absorbed and enter the portal vein
to the liver
• those FA’s with more than 10 carbons are resynthesized
by the liver to triglycerides
• they are then converted into chylomicrons and pass to
the lymphatic system
• some FA’s entering the liver are oxidized for energy,
others stored
• blood lipids: 45% P-lipids, 35% triglycerides, 15%
cholestrol esters, 5% free FA’s
 Lipid
Digestion/Abs
orption
 Lipid
Digestion/Abs
orption
 Characteristics of Fat Storage

• Most of the body’s energy stores are

triglycerides
• storage is in adipose, source is dietary or
anabolism (synthesis) from COH or AA
carbon skeletons
• remember obesity?
• adipose can remove FA’s from the blood
and enzymes can put them back
 Fatty Acid Nomenclature
• Nomenclature reflects location of double bonds
• also used are common names (e.g., oleic, stearic,
palmitic)
• linoleic is also known as 18:2 n-6
• this means the FA is 18 carbons in length, has 2
double bonds, the first of which is on the 6th
carbon
• arachidonic = 20:4 n-6
What’s in a Name??

Fatty Acid Nomenclature

 Essential Fatty Acids
• Only recently determined as essential (1930)
• body can synthesize cholesterol, phospholipids
• research: same as AA’s but via addition (EFA’s
added improved growth, NEFA’s didn’t)
• requirement determined by depleting fat reserves
of subject animal: difficult
 Essential Fatty Acids (fish)
• Most NEAA found in marine food webs
• Essential fatty acids (to date):
– linoleic (18:2 n-6; terrestrials; fish - not really)
– linolenic (18:3 n-3; terrestrials; fish)
– arachidonic (20:4 n-6; marine maybe)
– eicosopentaenoic acid (20:5 n-3, marine)
– docosohexaenoic (22:6 n-3, marine)
• Why? Because elongation beyond 18 carbons is very difficult
in marine fish (lack pathways)
• actual EFA requirement is a matter of whether the fish is
FW/SW or WW/CW
 Essential Fatty Acids (most animals)

• salmonids need n-3 FA’s for membrane flexibility

in cold water (why does this work?)
• trout can elongate and desaturate n-3 FA’s
• Linoleic acid (18:2 n-6) is the most essential
• addition of arachidonic is also helpful in deficient
diets, but can be synthesized from linoleic
(maybe sparing effect)
• EFA’s, like EAA’s, must be dietary
 Essential Fatty Acids
LINOLEIC CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH
18:2 n-6
LINOLENIC CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH
18:3 n-3
EICOSOPENTAENOIC ACID
CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)3COOH
20:5 n-3
DOCOSOHEXAENOIC ACID - YOU CAN DO THIS ONE!
Lipids as Crustacean Energy Sources

• Largely, n-6 FA’s (linoleic) used for energy

• as temperature drops, requirement for
monounsaturated and PUFA’s increases
• change in temperature = change in diet
• cold water species = increased dietary HUFA’s
• maturation animals: increased requirement for 20:4
n-6, 20:5 n-3 and 22:6 n-3 for proper spawning