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Lipids

PH 161 Biochemistry
Group 2
Prof. Palaruan

Objectives
By the end of the class, you should be able:
I. To enumerate the characteristics of Lipids
II. To explain the basic structure of Lipids
III. To classify Lipids based on their structure
IV. To enumerate some of the biomedical
importances of Lipids
V. To explain the process of Lipid digestion

Chemistry: Definition
Lipids are a class of chemically diverse molecules
that are generally non-polar!

Chemistry: Definition
Lipids are usually any fatty acid
and its derivatives, or any
substance biosynthetically or
functionally related to them.

Chemistry: Definition
In general, they are for storage (fatty acids and oils),
for use as structural components of biological
membranes (phospholipids and steroids), and as
enzyme cofactors, electron carriers and pigments
among others.

Chemistry: Characteristics
Lipids are generally insoluble in water, and hence,
nonpolar like hydrocarbons.
There are some lipids that exhibit amphipathicity,
meaning part of the molecule is hydrophobic and
another, hydrophilic.
Examples: Bile salts, phospholipids, sphingolipids,
fatty acids, and some cholesterols

Chemistry: Characteristics
These amphipathic molecules tend to self orient in
oil:water interfaces.

Chemistry: Characteristics
When a critical concentration of amphipathic lipids is
present in an aqueous medium, they tend to form
micelles.

Chemistry: Characteristics
Lipids are important dietary constituents as they have
high energy value.
1g of fat = 9 kcal
1g of protein = 4 kcal

Chemistry: Characteristics
In the body.

Chemistry: Characteristics
As used in transport

Structure
Lipids generally have both polar and non
polar ends (although predominantly polar).
For each classification of lipid, theres a
specific structure.

Structure
FATTY ACIDS
-are the precursors to more complex lipids
-consist of a carboxylic acid and a long unbranched
hydrocarbon chain
-may be saturated (no double bond C=C present) or
unsaturated (double bonds are present)

Structure
a. Saturated Fatty Acids

Structure
b. Unsaturated Fatty Acids
- may be mono or poly

Structure
b. Unsaturated Fatty Acids
-may also be cis or trans

Structure
WAXES
-esters with long hydrocarbon chains on both ends

Structure
PHOSPHOLIPIDS
-contains a hydrophobic tail and hydrophilic
head
-glycerol esterified with two fatty acids and
one phosphate group
-hydrophilic: glycerol, phosphate and choline
hydrophobic: the remainder of the molecule

Structure
PHOSPHOLIPIDS

Structure
PHOSPHOLIPIDS

Structure
STEROIDS
-exhibits a ring of three adjacent cyclohexanes and a
single cyclopentane

Structure
TRIACYLGLYCERIDES
-fatty acid triesters of glycerol

Structure
GLYCOLIPID
-sugar-containing lipid

Structure
PROSTAGLANDINS
-cyclic fatty acid compounds
-always contain 20 carbons, and a 5-member ring

Precursors to Lipids
Molecules from where lipids are formed
Namely the ff:
Fatty acids
Glycerol
Hydrocarbons

Precursors to Lipids
a. Fatty acids
building blocks
composed of C, H, O
arranged in chains
carrying terminal
carboxyl (-COOH)
which gives the acidic
properties of the
molecule

b. Glycerol
Glycerol (or Glycerine)
is a simple polyol with
three hydroxyl (-OH)
groups.
It serves as the
backbone of the
triglycerides or fats.

Precursors to Lipids
c. Hydrocarbons
an organic
compound
consisting entirely
of hydrogen and
carbon
alkanes, alkenes,
alkynes

Classifications
1. Simple Lipids
fatty acid esters with alcohols
do not carry any other substances
Examples are:
Fats/Trigycerols
Waxes

1.1 Triglycerols
also known as triacylglycerides/triglycerides or
triacylglycerols, more commonly known as fats
esters of fatty acids with the alcohol glycerol
usually solid (fats) in room temperature
liquid state of fats (at higher temperature) is
termed as oil

1.1 Triglycerols
stored as fat
droplets in
specialized
vertebrate fat cells
called adipocyte
most abundant
lipids in nature

1.1 Triglycerols
stored in seeds/plant cells
Triacylglycerides are either simple (three fatty
acid radicals are identical or similar) or mixed
(three fatty acids are different)
many natural fats found in foods are complex
mixtures of simple and mixed triacylglycerols

1.1 Triglycerols
A.

Saturated Fats (no double bond)


animal in origin
solid at room temperature
called saturated because of Hydrogen

1.1 Triglycerols
B. Unsaturated Fats (with double
bonds)
Plant oils
Lower cholesterol layer
two categories
MUFA (monosaturated fatty acid--1 double bond only)
PUFA (polysaturated fatty acid--numerous double bonds)
PUFA is healthier

1.2 Waxes
Are esters of long-chain fatty acids
with long-chain monohydroxy
alcohols having higher molecular
weight
in solid phase
generally higher melting point than
triacylglycerols
water repellant, with a firm
consistency
used in manufacture of lotions,
ointments, and polishes
(shoewaxing)

Classifications
2. Complex Lipids
esters of fatty acids containing groups in addition to fatty acids
and an alcohol, a phosphoric acid residue
usually have nitrogen-containing bases and other constituents

!4 Pics One Word!

2.1 Phospholipids
Glycerophospholipid
- form from phosphatidic
acid by esterification of the
phosphoric acid residue
- amphipathic: polar head
and nonpolar tails
- found in membranes (cell
membranes): structural
component

Sphingophospholipid
- form from ceramides by
double esterification of
phosphoric acid: to the
primary alcohol group of
sphingosine
- abundant in brain and
nervous tissue:
sphingomyelin (key
component of the myelin
that surrounds the axons)

2.2 Glycolipids
- contain a sugar residue (may be mono-, di- or oligosaccharide); no
phosphate group
- found in the blood as they act as receptors at the surface of the red
blood cell

Glyceroglycolipid
- glycerol backbone
- cerebroside
(galactocerebroside): found
primarily in the brain and
peripheral nervous tissues

Sphingoglycolipid
- glycosphingolipid
- sphingosine backbone
- found at the outer face of
plasma membranes

Tay-Sachs Disease
-

occurs when harmful quantities of a


sphingoglycolipids accumulate in the
nerve cells of the brain

2.3 Lipoprotein
- contains both proteins and lipids
- enzymes, transporters, structural proteins, antigens, adhesins
and toxins
- High density (HDL) and low density (LDL) lipoproteins: enable
fats to be carried in the blood stream
-

High levels of lipoproteins (LDL) can increase the ri


heart disease: atherosclerosis (stroke and heart attack)

Classifications
3. Derived Lipids
Derived Lipids are derived from simple and
compound lipids via hydrolysis
Namely the ff:
Steroids and hormones
Fatty aldehydes
Ketone Bodies
Lipid Soluble vitamins and micronutrients

!4 Pics One Word!

Derived Lipids
a. Steroids and some hormones
Steroids are flat molecules with four interlocking
rings with no fatty acid tail. One of the important
steroids of the body is cholesterol.
Hormones such as sex hormones testosterone,
estrogen and progesterone are also classified
under steroids.
Vitamin D is also a steroid.

How do Anabolic Steroids


work?
Anabolic-androgenic steroids promote growth of
muscles. Once ingested or injected, steroids travel in
the bloodstream to the skeletal muscles where they
bind with androgen receptors. They react with the
DNA of the cells and stimulate protein synthesis
which leads to increase in cell size or muscle
hypertrophy.
***Warning: There are side-effects!

Derived Lipids
b. Fatty aldehydes
Aldehydes with fatty aliphatic 8 or more
carbon membered chain attached.

Derived Lipids
c. Ketone Bodies
Three water-soluble
molecules produced
by the liver when the
glucose level of body
is low in level (ie.
during low food
intake) as sources of
energy.

Acetone

Acetoacetic
acid
Betahydroxybutyr
ic acid

Excess Ketone Bodies


Ketosis
Presence of ketone bodies in
the blood
Ketonuria
Presence of ketone bodies
Ketone bodies are toxic and acidic.
Some can be expelled through
urination.
Acetone on the other hand can be
released out of the body via
respiration (your breath will smell
fruity)

Derived Lipids
d. Lipid-soluble vitamins
and micronutrients
Vitamins are essential
micronutrients needed
by the body is small
amount for proper
functioning. Some of
the fat soluble
vitamins are A, D, E, K
usually stored in liver
and adipocytes

Homeostatic Imbalance:
LDL
Low Density Lipoprotein
Bad cholesterol
Excess of LDL may lead to stroke, heart
attack and high blood pressure

Functions
1. STORAGE LIPIDS
Triacylglycerols or fats
provide stored energy
Adipocytes in vertebrates
Oils in plant seed

Functions
1. STORAGE LIPIDS
Why triacylglycerols as fuel instead of polysaccharides?
They produce more than 2x energy (from oxidation):
9 calories per gram, whereas protein and carbohydrate contain
only 4 calories per gram
Carbohydrates = ready source of energy, but fats = easier
and lighter to carry around because they are unhydrated unlike
carbohydrates

Functions
2. LIPIDS AS INSULATORS
Thermal Insulation Subcutaneous tissue: layer of fat
just below your skin helps keep
internal body temperature regular
despite the external temperature

E.g. Seals, walruses, penguins and other


warm-blooded polar animals, humans

Functions
2. LIPIDS AS INSULATORS
Electrical Insulation - Nonpolar lipids in
myelinated nerves

Functions
3. SOURCE OF FAT-SOLUBLE VITAMINS

Functions
3. SOURCE OF FAT-SOLUBLE VITAMINS
Vitamin A - furnishes the visual pigment of the vertebrate eye
and is a regulator of gene expression during epithelial cell
growth
Vitamin D - precursor to a hormone that regulates calcium
metabolism
Vitamin E - protects the membrane lipids from oxidative
damage
Vitamin K - essential in the blood-clotting process

Functions
4. PROTECTION
Layers of fat surround vital organs to protect them
from injury (Visceral Fat)
Waxes found on animal feathers, in human ears and
even on the leaves of plants function mainly in
protection

Functions
5. STRUCTURAL LIPIDS
Phospholipids are important component of cell membrane
structure (membrane permeability)
Sphingolipids at cell surfaces are sites of biological
recognition.
e.g. Glycosphingolipids as determinants of blood
groups O, A, B
Cholesterol, the major sterol in animals, is both a
structural component of membranes and precursor to a
wide variety of steroids.

The oligosaccaride head


groups of the
glycosphingolipids
determine if the blood
group is O, A, or B.

Functions
6. LIPIDS AS SIGNALS
Cellular metabolic regulators - Control of the bodys homeostasis
Steroid Hormones: estrogen, progesterone, cortisol, aldosterone

Functions
6. LIPIDS AS SIGNALS
Prostaglandins, Thromboxanes, Leukotrienes
Platelet-activating factor: released by basophils
and stimulates platelet aggregation and the
release of serotonin (a vasoconstrictor) from
platelets.

Spermaceti Organ
A. Spermaceti Organ of sperm whales 1. 90% of head
weight is spermaceti organ 2. blubbery mass
containing up to 4 tons of spermaceti oil triacylglycerol + waxes mixture - lots of unsaturated
fatty acids - liquid at normal body temp but solidifies
at lower temps 3. buoyancy of whale changes to
match surrounding waters when diving for food B.
Inheritable Human Diseases 1. Hydrolytic enzymes in
lysosomes break down lipids 2. When enzyme has a
defect, partial breakdown products accumulate in
tissues and cause serious damage

Biomedical Importance
Inheritable Human Diseases
1. Hydrolytic enzymes in lysosomes break down
lipids 2. When enzyme has a defect, partial
breakdown products accumulate in tissues and cause
serious damage

!4 Pics One Word!

Lipid Digestion
Major lipids in our diet are triacylglycerols and to a
lesser extent phospholipids.
The fat-soluble vitamins are absorbed dissolved in
the lipid micelles, but this is impaired on a very low
fat diet

Lipid Digestion
Hydrolysis of Triacylglycerols via gastric &
lingual lipases to aid emulsification
(Triacylglycerol -> Diacylglycerol + fatty acids)

Pancreatic Lipase is secreted into the


small intestine, aided by colipase

(Diacylglycerol -> monoacylglycerol + fatty acids)

Hydrolysis of monoacylglycerol

(only 25% of ingested triacylglycerol is completely


hydrolyzed into glycerol & fatty acids)

Bile salts enable emulsification of the


products of lipid digestion into micelles
and liposomes

Lipid Digestion
absorbed into
the intestinal
epithelium,
mainly of the
jejunum

All long-chain
fatty acids
absorbed are
converted back
to
triacylglycerol
in the mucosal
cells

Triacylglycerol
and other
products of lipid
digestion are then
secreted as
chylomicrons into
the lymphatics
and then enter
the bloodstream
via the thoracic
duct.

Lipid Digestion

THANK
YOU FOR
LISTENING!

References
http://www.ext.colostate.edu/pubs/foodnut/09315.html
http://biology.tutorvista.com/biomolecules/lipids.html
http://catalog.flatworldknowledge.com/bookhub/reader/2547?e=gob-ch17_s02
Hallare, A. Student Handbook in General Zoology
Harpers Illustrated Biochemistry
http://www.nutriology.com/GLmetab.html
http://courses.washington.edu/conj/membrane/lipids.htm
http://courses.washington.edu/conj/membrane/lipoprotein.htm
http://www.ext.colostate.edu/pubs/foodnut/09315.html
http://lipidlibrary.aocs.org/Lipids/whatlip/index.htm
Murray, R. et al. (2003). Harpers Illustrated Biochemistry, 26th Edition. USA: McGraw-Hill Companies, Inc.
NCS, Pearson. Lipids. (2015). Retrieved 11 August 2015 from http://biology.tutorvista.com/biomolecules/lipids.
html
http://www.phschool.com/science/biology_place/biocoach/bioprop/lipids.html
Lehninger Principles of Biochemistry
http://www.livescience.com/3349-steroids-work.html