Unit 4- LIPIDS

Group 3 BSMT-2D: De Asis, Ben Josef; Domingo, Marianne

Lorraine; Esquivel Christine; Garino, Sofia May; Gongora, Erica
Mae

WHAT ARE THE LIPIDS?

A

broad range of organic compounds

that dissolve easily in organic solvents,
but range in their solubility in water.
Hydrophobic water-fearing
Lipophilic fat-loving
lipid is synonymous with fat, but
also includes phospholipids, sterols,
etc.
chemical structure: glycerol + fatty
acids

Lipid Molecule

SOURCES OF LIPIDS
Oils

and Fats

Most oils come from plants and are

largely unsaturated, although certain
plant oils, such as palm and coconut,
are highly saturated. Fats, on the other
hand, tend to come from animals and
have more saturated fatty acids.

SOURCES OF LIPIDS
Waxes,

Cholesterol and Steroids

Wax sources include bees, plants such as

jojoba (Simmondsia chinensis) and
carnauba palm (Copernicia cerifera),
and sheep, whose wool contains the wax
lanolin.
Cholesterol comes from animal tissue,
found in cell membranes and as a parent
compound for a variety of steroid
hormones.

PROPERTIES OF LIPIDS
Hydrophobic
Hydrolysis
Hydrogenation
Halogenation
Saponification
Oxidation
Rancidity

(Oxidative and hydrolytic)

FUNCTIONS OF LIPIDS
Excellent

energy reserves
Structure of cell membranes
Organ padding
Body thermal insulation
Essential fatty acids (EFA)
Hormone synthesis
Fat soluble vitamin absorption

FUNCTIONS OF LIPIDS
Concentrated

sources of energy (9.45

kcal/g)
Provide means whereby fat-soluble
nutrients (e.g., sterols, vitamins) can
be absorbed by the body
Structural element of cell, subcellular
components
Components of hormones and
precursors for prostaglandin synthesis

CLASSIFICATION OF
LIPIDS

CLASSIFICATION OF LIPIDS
SIMPLE LIPIDS
Fatty Acids
Triglycerides
Waxes
COMPOUND LIPIDS
Phospholipids
DERIVED LIPIDS
Sterols

SIMPLE LIPIDS: FATTY ACIDS

Key

building blocks for lipids

Chains of carbon atoms with a
carboxyl group at one end, and a
methyl group at the other
May be free or attached to
another compound
Determines the characteristics of
the fat

SIMPLE LIPIDS: FATTY ACIDS

CHAIN LENGTH
Short chain = less than 6 carbons
Medium chain = 6-10 carbons
Long chain = 12 or more carbons
The shorter the carbon chain, the
more liquid the fatty acid is

SIMPLE LIPIDS: FATTY ACIDS

SATURATION
SATURATED

FATTY ACID =If all

the carbon atoms in the chain are
joined with single bonds, and the
remaining bonds are attached to
hydrogen

SIMPLE LIPIDS: FATTY ACIDS

SATURATION
UNSATURATED

FATTY ACID = If
adjoining carbons are joined by double
bonds.

SIMPLE LIPIDS: FATTY ACIDS

UNSATURATED
One double bond =
monounsaturated fatty acid
Two or more double bonds = polyunsaturated fatty acid

SIMPLE LIPIDS: FATTY ACIDS

Long-chain

saturated fatty acids stack

tightly and form solids at room
temperature
Monounsaturated and polyunsaturated
fatty acids dont stack compactly and
are liquid at room temperature
Short-chain saturated fatty acids are
also liquid at room temperature
Figure 5.6

SIMPLE LIPIDS: FATTY ACIDS

TWO TYPES OF BOND FORMATION:
CIS - hydrogens on the carbons joined
by a double bond are on the same side
= the carbon chain is bent
TRANS hydrogens on the carbons
joined by a double bond are on the
opposite side = the carbon chain is
straighter

SIMPLE LIPIDS: FATTY ACIDS

Omega-3

Fatty Acid double bond

at carbon 3
Omega-6 Fatty Acid double bond
at carbon 6
Omega-9 Fatty Acid double bond
at carbon 9
*count

carbons from the methyl

(omega) end

Omega 3

Omega 6

Omega 9

SIMPLE LIPIDS: FATTY ACIDS

NOMENCLATURE
Alpha and Omega

SIMPLE LIPIDS: FATTY ACIDS

Nonessential

Fatty Acids our

body can make certain fatty acids so
they are not required in the diet
Essential Fatty Acids our bodies
cannot make C-C double bonds
before the 9th carbon from the
methyl end, so we must get these
fatty acids from our diet
EFAS = omega-6 linoleic acid &
omega-3 alpha-linolenic acid

FATTY ACIDS
Omega-3: Alpha-Linolenic Acid
(ALA), Eicosapentaenoic Acid
(EPA), Docosahexaenoic Acid
(DHA)

Omega-6:

Linoleic Acid,
Arachidonic Acid

Sources of Omega3 Fatty Acids

Flaxseed,

soybean oil,
walnuts, some leafy dark
green vegetables (ALA)
Fatty fish: salmon, tuna, and
mackerel, fish oils (EPA and
DHA)

Sources of Omega6 Fatty Acids

Seeds,

nuts, common
vegetable oils: corn,
safflower, cottonseed,
sunflower seed, peanut
(linoleic acid)
Meat (arachidonic acid)

SIMPLE LIPIDS: FATTY ACIDS

EICOSANOIDS
A small percentage of fatty
acids become eicosanoids
They contain 20 or more
carbons and are important in the
inflammatory process, blood
vessel dilation and constriction,
and blood clotting.

EICOSANOIDS

Omega-6s
Linoleic acid is converted to
arachidonic acid and
eicosanoids are formed.
Overall effect: constricting
blood vessels, promoting
inflammation and blood
clotting

EICOSANOIDS
Omega-3s
Alpha-linolenic acid is converted
to eicosapentanoic acid (EPA)
and docosahexanoic acid (DHA)
and eicosanoids are formed
Overall effect: dilating blood
vessels, discouraging blood
clotting, and reducing
inflammation

SIMPLE LIPIDS:TRIGLYCERIDES
STRUCTURE
Triglyceride - three fatty acids
attached to a glycerol backbone
Diglyceride two fatty acids
+glycerol
Monoglyceride one fatty acid
+glycerol

Fatty Acids

Triglyceride

TRIGLYCERIDES
FUNCTIONS
Major lipid in the body and diet
Stored fat provides about 60% of
the bodys resting energy needs
compactly!
Insulation and protection
Carrier of fat-soluble compounds
Sensory qualities flavor and
texture

COMPOUND LIPIDS:
PHOSPHOLIPIDS
Contain

a glycerol bonded to two fatty

acids
The phosphate group is hydrophilic
while the fatty acids groups are
lipophilic
Because of this structure, phospholipids
are ideal emulsifiers, and the perfect
structure for cell membranes

Functions
Cell Membranes
Phosholipids are the major component of
cell membranes
Fatty acids, choline, as well as other
substances are bound in the phospholipid
layer
Lipid Transport
In the stomach
In the intestine
In the bloodstream, and the lymphatic
system

Channel

Hydrophilic
Hydrophobic
Hydrophilic

Protein

Functions
Emulsifiers
Lecithins are used by the food
industry to:
Combine foods that wouldnt normally
mix
Increase dispersion and reduce fat
separation
Increase shelf-life, prolong flavor
release, and prevent such products as
gum from sticking to teeth

Phospholipids in Foods
A

typical diet contains only about 2

grams per day
Lecithin (phosphatidylcholine) is
the major phospholipid and is
found in:
Liver, egg yolk, soybeans, peanuts,
legumes, spinach, and wheat germ
Usually

lost during food processing

DERIVED LIPIDS: STEROLS

Sterols

are hydrocarbons with a

multiple ring structure
They are hydrophobic and lipophilic
Contain no fatty acids
Cholesterol is the best-known sterol,
found only in animal products

CHOLESTEROL: Functions
Major

component of cell membranes

(especially abundant in nerve and
brain tissue)
Precursor molecule: Example - Vitamin
D and estrogen are synthesized from
cholesterol
Important in the synthesis of bile acids

CHOLESTEROL: Synthesis
The

liver manufactures most of the

cholesterol in our bodies
The intestine and all cells contribute a
small amount
Overall, the body produces about
1000 mg per day
Serum cholesterol levels are
homeostatically controlled (set-point)

FAT SOLUBLE VITAMINS

What are Vitamins?
Vitamins are essential micronutrients your
body needs in small amounts for various roles
throughout the human body. Vitamins are
divided into two groups: water-soluble (Bcomplex vitamins and C vitamins) and fatsoluble vitamins (A, D, E and K). Unlike watersoluble vitamins that need regular replacement
in the body, fat-soluble vitamins are stored in
the liver and fatty tissues, and are eliminated
much more slowly than watersoluble vitamins.

VITAMIN
A
(Retinol)

D
(Calciferol)

OCCURRENCE
Cod-liver oil, liver, kidney,
milk products, butter, yolk,
as provitamine A in carrots

Helping the eyes adjust to light

changes.

Cod-liver oil, liver, milk,

yolk, butter, sea fish,
herring, champignons,
avocado

It works by increasing the

amount of calcium absorbed
from the small intestine, helping
to form and maintain bones.

E
Stabilization of the immune
(Tocopherole) system, anti-inflammatory,
cell replacement,
protection from radicals,
modulates cholesterol level
and hormone household,
important for blood
vessels, muscles and
reproduction organs
K
(Phyllochinon
e

FUNCTION

Necessary for formation of

the blood clotting factors

Benefits the body by acting as

an antioxidant, and protecting
vitamins A and C, red blood
cells, and essential fatty acids
from destruction.

is naturally produced by the

bacteria in the intestines, and
plays an essential role in normal
blood clotting, promoting bone
health, and helping to produce
proteins for blood, bones, and

PROSTAGLANDIN
-any of various oxygenated
unsaturated cyclic fatty acids of
animals that are formed chiefly by the
action of cyclooxygenase on
arachidonic acid and perform a variety
of hormonelike actions (as in
controlling blood pressure or smooth
muscle contraction)

STRUCTURE OF
PROSTAGLANDIN

Prostaglandins are unsaturated

carboxylic acids, consisting of of a 20
carbon skeleton that also contains
a five member ring and are based
upon the fatty acid, arachidonic
acid. There are a variety of structures
one, two, or three double bonds. On
the five member ring there may also
be double bonds, a ketone, or alcohol
groups. A typical structure is on the
left graphic.

FUNCTIONS OF
PROSTAGLANDIN
There are a variety of physiological effects including:
1.

2.

Activation of the inflammatory response,

production of pain, and fever. When tissues are
damaged, white blood cells flood to the site to try
to minimize tissue destruction. Prostaglandins are
produced as a result.
Blood clots form when a blood vessel is damaged.
A type of prostaglandin called thromboxane
stimulates constriction and clotting of platelets.
Conversely, PGI2, is produced to have the
opposite effect on the walls of blood vessels
where clots should not be forming.

FUNCTIONS OF
PROSTAGLANDIN

3. Certain prostaglandins are involved with the

induction of labor and other reproductive
processes. PGE2 causes uterine contractions
and has been used to induce labor.
4. Prostaglandins are involved in several other
organs such as the gastrointestinal tract
(inhibit acid synthesis and increase secretion
of protective mucus), increase blood flow in
kidneys, and leukotriens promote
constriction of bronchi associated with
asthma.

DIGESTION, ABSORPTION,
TRANSPORT

DIGESTION
Mouth:

chewing, lingual lipase, and

dietary phospholipids
Stomach: gastric lipase
Small Intestine: CCK = bile, Secretin
= pancreatic juice (pancreatic lipase)
Micelles: tiny emulsified fat packets
that can enter intestinal cells
(enterocytes)

ABSORPTION
Most

fat absorption takes place in the

duodenum or jejunum micelles carry
monoglycerides and free fatty acids to the
brush border where they diffuse into
enterocytes
Bilesaltsareabsorbedintheileum(enterohepatic
circulation)
Once in the enterocytes, monoglycerides
and free fatty acids are reformed into
triglycerides
The triglycerides, cholesterol, phospholipids,
and protein carriers form LIPOPROTEIN

ABSORPTION
Oncetheselipoproteinsleavethecell,theybecome

CHYLOMICRONSandenterthelymphsystem
MCTs, short-chain fatty acids and glycerol
are absorbed directly into bloodstream.
They do not enter the lymph system.
Cholesterol and other sterols are poorly
absorbed. Overall, about 50% of dietary
cholesterol is absorbed.
Dietary fat increases cholesterol absorption
Fiber (especially soluble fiber) and
phytosterols decrease cholesterol absorption

TRANSPORTATION
Chylomicrons:
Largest & Least Dense of the lipoproteins
Transport diet derived lipids (triglycerides)
from the intestine, through the lymph, to
the blood and the rest of the body.
As chylomicrons pass through bloodstream,
body cells remove lipids from them.
Liver cells remove the remnants of the
chylomicrons from the blood and
reassembles them into new triglycerides.

TRANSPORTATION
Chylomicrons:
The liver is the most active site of
lipid synthesis; it uses fatty acids to
make cholesterol, other fatty acids,
triglycerides from carbohydrate,
protein and alcohol. The new lipids are
combined with a protein carrier and
are transported to other parts of the
body.

TRANSPORATION
VLDL: Very Low Density Lipoprotein
Made in the liver
Transports mainly triglyceride (about 50%),
some cholesterol, and phospholipid.
VLDL travel through the body and cells
remove triglyceride from them.
As they lose triglyceride, the proportion of
cholesterol increases and they become
more dense; they become a low-density
lipoprotein (LDL).

TRANSPORTATION
LDL: Low Density Lipoprotein
Composed primarily of cholesterol (about 50%)
They circulate throughout the body and release
triglyceride, cholesterol and phospholipid to body
cells.
Body cells collect the lipids and use them to make
cell membranes, hormones or store them for later
use.
Liver removes LDL from circulation
Often termed Bad Cholesterol because a high
level of this lipoproteinis linked to heart disease.

TRANSPORTATION
HDL: High Density Lipoprotein
Transports cholesterol from the cells
back to the liver for recycling or
disposal
Often termed Good Cholesterol
because a high level of HDL is linked to
a lower risk of heart disease.

TRANSPORTATION
NOTE:

Lipoproteins with a low proteinto-lipid ratio have a low

density; those with a high
protein-to-lipid ratio have a
high density

LIPID METABOLISM

LIPID METABOLISM
The

hydrophobic and highly reduced structure of

triglycerols allows them to serve as a compact and
rich source of energy (e.g., in average U.S. diet,
30 40% of calories are provided by fat). The
metabolism of lipids include the degradation and
synthesis and regulation of these processes. A
major emphasis is placed on the role of the central
metabolite in lipid metabolism: acetyl-CoA.
Lipid metabolism is closely connected to the
metabolism of carbohydrates which may be
converted to fats.

LIPID METABOLISM: CATABOLIC

PATHWAY
Catabolism

refers to chemical reactions that

result in the breakdown of more complex
organic molecules into simpler substances.
Catabolic reactions usually release energy
that is used to drive chemical reactions.
The energy of catabolic reactions is used to
drive anabolic reactions.

BETA OXIDATION OF FATTY

ACIDS

Fatty Acid Oxidation

Initial Step: Requires an ATP to synthesize acetyl CoA with the fatty acid.

-oxidation of fatty acids

substrate: acyl-CoA
product: n acetyl-CoA, n NADH + H+, n FADH2
function: gain of energy from fatty acids
subcelullar location: matrix of mitochondria
organ location: liver, skeletal muscles and other
tissues with expection to CNS
regulatory enzyme: carnitine acyltransferase I

LIPID METABOLISM: ANABOLIC

PATHWAY
Anabolism

refers to chemical reactions in which

simpler substances are combined to form more
complex molecules. Anabolic reactions usually
require energy.

Anabolic reactions build new molecules and/or

store energy.

LIPOGENESIS

Fatty acid may be converted to triacylglycerol,

degradated to generate energy, or utilized in
membrane synthesis
When serum glucose level is high after meal,
insulin promotes triacylglycerol synthesis by
facilitating the transport of glucose into
adipocytes - LIPOGENESIS

MEDICAL IMPLICATIONS

HYPERLIPIDEMIA
Hyperlipidemia is a heterogeneous group of
disorders characterized by an excess of lipids in
the bloodstream. These lipids include
cholesterol, cholesterol esters, phospholipids,
and triglycerides. Lipids are transported in the
blood as large 'lipoproteins
Hyperlipidemia is a major, modifiable risk factor
for atherosclerosis and cardiovascular disease,
including coronary heart disease; this is true
both of disorders involving
hypercholesterolemia and hypertriglyceridemia.

LIPOPROTEINS
Lipoproteins are divided into five major
classes, based on density:
chylomicrons, very low-density
lipoproteins (VLDL), intermediatedensity lipoproteins (IDL), low-density
lipoproteins (LDL), and high-density
lipoproteins (HDL). Most triglyceride is
transported in chylomicrons or VLDL,
and most cholesterol is carried in LDL
and HDL

TYPES OF HYPERLIPIDEMIA
Primary hyperlipidemias are probably
genetically based, but the genetic defects
are known for only a minority of patients
Secondary hyperlipidemia may result
from diseases such as diabetes, thyroid
disease, renal disorders, liver disorders,
and Cushing's syndrome, as well as
obesity, alcohol consumption, estrogen
administration, and other drug-associated
changes in lipid metabolism

Causes of hyperlipdemia

Extra Hepatic Obstruction

2. Biliary Cirrhosis
3. Diabetes Mellitus
4. Hypothyroidism
5. Alcohol
6. Nephrotic Syndrome
7. Obesity
8. High Dose Thiazide Diuretic
9. Exogenous sex hormone
10. Steroids
1.

Heart Disease
More

than 58 million Americans have

at least one form of CVD stroke,
hypertension, or coronary heart
disease
1 in 9 women, and 1 in 6 men aged
45-64 years of age have some form of
heart disease
Myocardial Infarction (heart attack) is
the leading cause of death in American
men and women

coronary heart disease

Atherosclerosis
A

slow, progressive disease that begins in

childhood and takes decades to advance.
Basically, plaque (lipid deposits and other
substances) forms in response to injuries on the
artery wall
Plaque can eventually completely occlude the
artery leading to MI
Injury can be caused by: hypercholesterolemia,
oxidized LDL, hypertension, smoking, diabetes,
homocysteine, and diets high in saturated fat

Prevention of Lipid Disorder

Reduce fat
Cut

down on high fat foods

E.g. butter, margarine, oil,
mayonnaise

Consume small amounts of

unsaturated fats
Do

not eliminate fat completely

since it is high in calories

Prevention of Lipid Disorder

Limit added sugar and alcohol
Added

sugar and alcohol are empty

calories

Watch portions of all food

fat

free calorie-free

Drink at least 8 glasses of water

everyday
Water

filling

is calorie-free, refreshing, and

Prevention of Lipid Disorder

Increase intake of vegetables,
fruits, and whole grains
Loaded

with fiber
Contain high amounts of vitamins,
minerals, and phytonutrients

Include low-fat protein-rich food

with every meal
E.g.

tofu, beans, eggs, and fish

Prevention of Lipid Disorder

Slow down when eating
Too

fast eating will exceed

calorie needs before realizing
we are full

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