Lipid Chemistry must avoid fatty foods because it is considered to be calorie densed,

BIOCHEM A Dolores V. Viliran, M.D., DPAFP
Lipids are substances that are water insoluble, polar and non polar,
hydrophilic and hydrophobic. They are amphipahtic in nature. The
structure of the different lipids is different from one another but
they are mainly related because of their insolubility in water.
• Lipids: a heterogeneous class of naturally occurring organic
compounds classified together on the basis of common
solubility properties
high energy content but if you are sedentary, the tendency of these
carbohydrates is to store the excess energy as triglycerides, stored in
adipocytes. The adipocytes hypertrophy (increase in number) &
hyperplasia (increase in size) when there is excess triglycerides.
From the adipose tissue you can derive energy by mobilizing
triglyceride. It is called Free Fatty Acid mobilization. From the stored
triglyceride in the adipose tissue and then fatty acid will be oxidized
into C02 and H20 leading to generation and production of ATP.
Triglyceride is the major storage of carbohydrates.

The structure of triglyceride from cholesterol is very different because

cholesterol is cyclic,it is a ring form while triglyceride and phospholipid
is linear. All of them are related based on their insolubility in water
but soluble in aprotic organic solvents that are non polar including
diethyl ether, chloroform, methylene chloride, and acetone.

Lipids are amphiphatic in nature, meaning it has both polar and non
polar substance. Lipids classified as amphiphatic are lipids found in cell
membrane. One importance of lipids is being part of the cell
membrane. The different amphiphatic lipids are; phospholipids,
sphingolipids and free cholesterol. That makes the cholesterol
important because it is part of the cell membrane, the free
cholesterol.
The back bone of triglyceride is Glycerol, a sugar alcohol from a
Lipids include: carbon sugar, glyceraldehydes. For you to store fats, you need
carbohydrates. If you intake excess carbohydrates, you will increase
 Open chain forms weight as it will be deposited in your adipose tissues as fats because
 They are linear. there is a way to convert carbohydrates to fats. Triglyceride is
 Also includes fatty acids, triacylyglycerol, sphingolipids, composed of 3 fatty acids attached to glycerol. The precursor for fatty
phosphoacylglycerol & glycolipids. acid synthesis is Acetyl CoA which can be derived from glucose,
 We have also lipid soluble vitamins, the Vitamins ADEK. protein and fatty acids. If in excess intake, it will be converted as
 Lipids also include eicosanods such as prostaglandins, Acetyl CoA and later will be converted to Fatty Acids.
leukotrienes, and thromboxanes.

 Cyclic forms
 cholesterol, steroid hormones, and bile acids
 From cholesterol we can derive steroid hormones e.g.
estrogen for female and testosterone for male.
 Cholesterol is very important because of you are
hypocholesterolemic, you will have a deficiency of these
hormones.
 We can also derive bile acids from cholesterol which is
important for emulsification of fats to enhance digestion
and absorption of fats.
 High levels of cholesterol are bad because it predisposes to
atherosclerosis.

Energy source: 9 calories per gram

Adipose (TAG) → Fatty acids → CO2 + H2O + ATP
Major component of cell membrane
 Phosphoglycerides
 Sphingolipids
 Cholesterol

Another important function of cholesterol will be the major energy

source. It is also called the “spare tire” or reserve. The first source of
energy is carbohydrates, glucose, starch & glycogen. If you lack
glucose, your body will start to use fats as a source of energy. A gram
of fats can yield 9 calories per gram. If you’re already an obese, you

1|Hazel A. Perilla,RN
Phospholipids are termed as Phospholipids because it contains There are fats that are water insoluble. Transport proteins are
Phosphate. It is the major component of the membranes. It is also a needed to transport fats in the blood. Transport proteins are
component of Arachidonic Acid which will be converted to lipoproteins such as HDL, LDL, VLDL and Chylomicrons.
Eicosanoids. Inositol Triphosphate is derived from Phosphatidyl
inositol and this is considered as a second messenger similar with
diglyceride. It is important in cell to cell communication.

The components of the cell membrane are: phospholipids,

sphingolipids and free cholesterol.

Vit D can be derived from cholesterol. It is stored in the skin,

7 dehydro cholesterol. We need sunlight for it to be activated.

Bile Salt is also ampiphatic and it increases the surface area of fats
for digestion and absorption, Emulsification.
Liver is responsible for the bile production. If you have aproblem in
liver, you will have a problem in bile production and you will have a
problem in digestion and absorption of fats.

The main mechanism of action of steroid hormones is at the level of

DNA molecule. DNA contains gene so they play a role in gene
expression.
The effect of Thromboxane is thrombus formation, platelet
aggregation. In contrast Prostacyclin prevents platelet aggregation.
Prostaglandin is the major substance for inflammation.
This is a structure of a fatty acid made up of RCOOH. It has a
carboxylic group. The R group is a hydrocarbon chain. Hydrocarbon
chain is composed of Carbon and Hydrogen. 3 Hydrogen can be
found at the end of the chain while 2 H can be found at the middle.

Vitamin A is for vision, D is for calcium metabolim, E is for antioxidant

and vit K is for blood coagulation.

There are three types of Ketones; Acetone, for diabetic patients,

their breath is fruity acetone breath. Acetoacetic acid & beta
hydroxybutyric acid. You produce ketones whenever you oxidize fats.
Ketoacidosis will result if you use fats as energy.

Bile that is produced in the liver and stored in the gallbladder is

released into the Intestines for fat emulsification. Gallbladder is used
for the concentration and storage of bile. Complication of
cholecystectomy is diluted bile. If you eat fatty foods after
undergoing cholecystectomy, you may experience diarrhea &
steatorrhea due to not enough bile concentration.

Bile salts are used to emulsify fats forming mixed micelles. Once you
have the mixed micelle. This will be acted upon by the Lipase enzyme
Fatty acids can be classified based on the number of their carbons;
coming from Pancreas, Pancreatic Lipase. The digested products will
short, medium & long. Among the 3 classification of fatty acids, the
assemble as a micelle and will be absorbed in the intestinal mucosa.
long chain fatty acids need bile for digestion. If you have a problem in
Emulsification is dispersing large fat globules into smaller globules.
bile your diet must be modified by preventing Long chain fatty acids.
Smaller fat globules will have greater surface area and more enzymes
can interact with emulsified fats.
LIPID CLASSES
 FATTY ACID DERIVATIVES The R group is also called Alkyl chain & Hydrocarbon. This is
composed of C & H. It is non polar because it doesn’t contain
TRIACYLGLYCEROLS (TAG)
Oxygen, therefore it is water insoluble. The R group will be
WAX ESTERS considered as non polar while carboxylic group is considered as
PHOSPHOLIPIDS
polar. Fatty acid is also considered ampiphatic. Fatty acid has a pKa
of around 4.2. Blood pH is 7.4 therefore it is higher than the pKa of
SPHINGOLIPIDS Fatty acids. The state of fatty acid in the blood is Negative, anion in
ISOPRENOIDS the blood. Carboxylic is uncharged when the pH is 7.4 because the
o terpenes pKa is 4.2, it will ionized so you have now a carboxylic anion,
o steroids
negatively charged. So for example, the fatty acid is Palmitic ( 16 C
LIPOPROTEINS

2|Hazel A. Perilla,RN
 atoms) if it is uncharged it is Palmitic acid but if it is (-) charged, it is
Palmitate.Note; (-) charged Fatty acid ends with –ate.
Palmitic : R-COOH ( uncharged )
Palmitate: RCOO-+H+ ( - ) uncharged

pKa means logarithm of acid dissociation constant. The lesser

thae value of pka the stronger the acid is.
Fatty Acids (Cont’d)
Length of fatty acid plays a role in its chemical character
• Usually contain even numbers of carbons (can contain
odd, depending on how they are biosynthesized)
• FA that contain C=C, are unsaturated: If contain only C-
C bonds, they are saturated
This is a structure of a saturated fatty acid, Palmitic acid with 16 C
atoms. Stearic acid is higher by 2 C atoms.
R end: carboxyl group – water soluble
Middle: alkyl group/ hydrocarbon chain – non water soluble, oil
soluble
L end: methyl end- last C atom on the left, oil soluble
Names and Chemical Descriptions of some common Fatty
acids

Naturally occurring fatty acids are even numbers. There is no odd

number in fatty acid classification. The length of fatty acids plays a
role in chemical character. It contains even numbers of C atoms but
sometimes it also has odd number.

Unsaturated Fatty acid : contain double bond Another way to name the fatty acid is using the omega. Fatty acids
Saturated Fatty acids: w/o double bond. that contain Omega-3 are α Linolenic Acid, EPA & DHA.

Naturally occurring saturated fatty acids contain single bond. Take

note, the melting temperature depends on the length of C atom, the
longer the C chain fatty acid , the higher the melting point needed
e.g. Arachidic 20 C atoms has a melting point of 77’C.

Fatty Acids (Cont’d)

• In most unsaturated fatty acids, the cis isomer
predominates; the trans isomer is rare

• Unsaturated fatty acids have lower melting points than

their saturated counterparts; the greater the degree of
unsaturation, the lower the melting point
Rule: The more double bond or greater degree of saturation, the
lower the melting point e.g. Arahicidonic acid with 4 double bonds has
the lowest melting point because it has the most number of double
bond.
Oleic, Linoleic and Linolenic contain 18 C atoms but they differ in the
number of double bond. Oleic contains 1 double bond, Linoleic
contains 2 while Linolenic (longest word among the 3) contains 3
double bonds.
The temperature of saturated is higher compared to unsaturated
because of the regular nature of chains, no double bond. If these fatty
acids combine together they will be packed in close parallel alignment
and that requires higher temperature to melt for the FA to be
separated.
• Unsaturated fatty acids have at least one C = C double bond
in the chains.
– In contrast, unsaturated fatty acids are all liquid at
room temperature because the cis double bonds
interrupt the packing of the chains. Thus less
energy is required to melt them. The greater the
degree of unsaturation, the lower the melting
point because there will be spaces in between. The
more double bond, the lower will be the melting
point.

3|Hazel A. Perilla,RN
 There are 2 basis for designation of double bonds:

Oleic acid contains double bond, with kink that makes space so the a. delta system – wherein you start counting from the right,
fatty acids will be mixed with one another. carboxylate as C1. From carboxylate start counting until you reach the
Monounsaturated FA (MUMA): one double bond double bond.
Polunsaturated FA (PUFA): one or more double bond
b. omega system – start counting from the last carbon on the left,
Oleic acid is classified as monounsaturated while the rest; linoleic α omega end, methyl carbon.
linolenic & arachidonic acid are considered as polyunsaturated FA.
Stearic & palmitic acid are classified as monounsaturated FA. C 1 = carboxylate
C 2 = -carbon
Q: Which among the fatty acids has the highest melting temperature? C 3 = -carbon
A. Linoleic acid C 4 = ¥ carbon
B. Linolenic acid Last carbon = -omega carbon methyl group
C. oleic acid
D.palmitic acid (because it is saturated) Note: learn how to count the double bonds using delta & omega
system. 27:45
Q: Which among the fatty acids has the lowest melting temperature?
A. Linoleic acid
B. Linolenic acid (because it contains the highest # of double bonds)
C. oleic acid
D.palmitic acid

Q: Which among the fatty acids has the highest melting temperature?
A. Lauric acid
B. stearic acid (because it has the longest alkyl chain)
C. oleic acid
D.palmitic acid

e.g. Oleic acid 18 C atoms is omega 9 ; delta 9

CIS & TRANS Isomerism/ configuration

α Linolenic is more of plants & vegetable. Fish oil, omega 3 is rich in CIS – both methyl and carboxyl on the SAME side.
EPA & DHA. TRANS – methyl and carboxyl group in the OPPOSITE side.

4|Hazel A. Perilla,RN
CIS and TRANS ISOMERISM
• Occurrence
Cis double bonds
• in humans, other animals, plants and bacteria
Production of Essential fatty acid
Trans double bonds derivatives
- Catalytic hydrogenation of vegetable oils
- Margarine, cookies, candies, fried foods

 ↑ double bonds= ↓ melting point

-Liquid at room temperature
 ↓ double bonds= ↑ melting point
-Solid at room temperature

Trans fatty acids are bad for our health. They are implicated for
atherosclerosis. Trans fat in layman’s term is hydrogenated vegetable
oil. If it’s hydrogenated in the process, you produce trans fat. In
doughnut manufacturers, they use Lard as hydrogenated vegetable
oil.

From the Linoleic we can produce the other omega 6 FA such as GLA,
DGLA & Arachidonic acid because we have the enzymes elongase,
delta 5 desaturase & delta 6 desaturase. Similar from Omega 3, we
can derive EPA & DHA from αLinolenic acid but we can label these as
conditionally essential because during rapid growth such as in
pregnancy, it is necessary for the fetus to have supplements of EPA &
DHA but for adults supplements are not really needed as long as we
have the source, αLinolenic acid. The true essential fatty acid is
Linoleic acid.

Dietary sources and tissue distribution of the

major n-3 PUFA
Essential FA are FA that can’t be produced in the body so it must be
Major Members Tissue distribution in mammala Dietary sources
supplemented from diet. Two essential FA are Linoleic & αLinolenic of Series

acid. These are essential because we don’t have enzymes that can Alpha- Minor component of tissues Vegetable oils
introduce double bond beyond C 9 e.g. delta 15. The enzymes that we linolenic (soy,canola,linseed,
lack are delta 12 & delta 15 desaturase. Both linoleic and linolenic Rapeseed) and leafy
vegetables
contains double bond at C12. In addition, linolenic has double bond at
C 15. To produce the linoleic acid we need delta 12 desaturase. To EPA Minor component of tissues Fish and shellfish
produce α linolenic acid we need delta 12 & 15 desaturase.
DHA Major component of Fish and shellfish
membrane phospholipids in
EPA & DHA are conditionally essential but they are nonessential FA retinal photoreceptors,
even though they have double bonds beyond C9 because EPA (20 C cerebral gray matter, testes
and sperm
atom), DHA (22 C atoms), GLA(18), DGLA(20) can be derived from two
essential FA because we have these enzyme elongase that can add C
atom and we have desaturase that can form double bond.

5|Hazel A. Perilla,RN
 Montelukast controls the Lipooxygenase enzyme thus decreasing the
ARACHIDONIC ACID action of Leukotrienes which is responsible for inflammation and
 A 20 – carbon Omega 6 Fatty acid with 4 double bonds. bronchoconstriction.
 AA can be converted to Eicosanoids ( substances containing ESSENTIAL FATTY ACIDS
20 C atoms) • Omega 6 FA : Linoleic acid
 Eicosanoids are essential for inflammation, clotting, and  Pro-inflammatory
immune response.  Arachidonic acid leads to the production of the
 prostaglandins inflammatory cascade, prostaglandins and
 thromboxanes leukotrienes of the even-series (PGE2, LTE2, etc.)
 lipoxins and leukotrienes  It produces the even series of prostaglandin &
leukotrienes.
PROSTAGLANDINS
 Prostaglandins: a family of compounds that have the 20- • Omega 3 FA : alpha linolenic acid
carbon skeleton of prostanoic acid  Anti-inflammatory: Prostaglandins of the one and
 First detected in seminal fluid from prostate gland three series (PGE1 and PGE3) and less
 The metabolic precursor is arachidonic acid (20 carbon inflammatory leukotrienes.
atoms: 4 double bonds)  Fish oil is also used as anti-inflammatory agent.
 We have different prostaglandins. PGE1, PGE2 etc.  Eicosanoids produced are odd number series
depending on the position of double bonds.
• Since they compete for the same enzymes, the more omega-
LEUKOTRIENES 6 FA we ingest, enzyme will be chanelled to omega 6 and
 Compounds also derived from arachidonic acid you produce a lot of pro-inflammatory,the less we are able
 Found in white blood cells (leukocytes) to utilize the beneficial influences of the omega-3 FA.
 Consists of 3 conjugated double bonds
 An important property is constriction of smooth muscles, • Humans still require both omega-6 and omega-3 fats, but
especially in the lungs responsible for bronchoconstriction. the optimal ratio is considered to be 2:1
 Bronchoconstriction is seen in Asthma. To control the attack
of asthma,give a drug that prevents Leukotrienes.

Biological Actions of Selected Eicosanoid

Molecules
ARACHIDONIC ACID Olive oil
LIPOOXYGENASE CYCLOOXYGENASE  High in antioxidants e.g. tocopherol, hydroxytyrosol and
oleuropein and in sterols which help reduce LDL and
Leukotrienes PGH2
PGI TxA2 increase HDL
Anti-platelet aggregation Platelet aggregation  May also possess some NSAID-like activity
Vasodilatation Vasoconstriction
 Extra virgin ( or “first-press”) olive oil has been shown to
have more health benefits than refined olive oil
PGE2 PGF2α  A small study shows that extra virgin olive oil, but not
Smooth muscle contraction Smooth muscle contraction regular olive oil reduced (LTB4) and thromboxanes (TXB2) in
Vasodilatation Vasoconstriction
human subjects.
 If you fry the polyunsaturated acid, it will just be oxidized so
Bronchoconstrictions better use olive oil as salad dressing.
Inflammations Vasoconstriction
Capillary Permeability
Omega 3 FA
 Fish(remember S.M.A.S.H: salmon, mackerel, anchovies,
sardines and herring) are high in omega-3 FA: EPA/DHA
There are two enzymes in the conversion of Arachidonic acid to (anti-inflammatory)
Leukotrienes and Prostaglandin. In the left pathway, Lipooxygenase  The salmon must be mercury free because the longer the
enzyme converts AA to Leukotrienes while in the right side, salmon is in the sea, the longer is its exposure to mercury.
Cyclooxygenase enzyme converts AA to Prostaglandin, Thromboxane  Omega-3 FA increase production of nitric oxide (vasodilating
& Prostacyclin. agent) by 43%- promotes arterial relaxation
 Sildenafil (viagra) contains nitric oxide.
THROMBOXANE – found in thrombocytes. Essential for platelet  Omega-3 fats (EPA/DHA) lower PGE2,thromboxane A2, LTB4
aggregation & vasoconstriction and increase anti-inflammatory PGI3, LTB5.
PROSTACYCLIN – antiplatelet & vasodilatation
PROSTAGLANDIN – involved in smooth muscle contraction. This is the
reason why we experience pain during menstruation (dysmenorrhea is
the painful contraction of the uterus.) To relieve the pain, treat with
NSAIDS whose action is to inhibit cyclooxygenase enzyme so the AA
will not be converted to Prostaglandin inhibiting the pain.

6|Hazel A. Perilla,RN
 TRIGLYCERIDES
 In humans
 The main storage form of energy for lipids.  Hydrolyzed by lipase to glycerol + FFA. Enzymatic
 An ester of glycerol with three fatty acids Hydrolysis (in vivo)
 It contains three fatty acids.  In industry
 Excess intake of carbohydrates will be converted to fatty  Hydrolyzed by NaOH(alkaline solution) to create
acids and it will be esterified with glycerol (sugar alcohol) glycerol + water-soluble soaps, Saponification or
 The acylglycerols are esters of fatty acids bound to the sugar Alkaline hydrolysis (in vitro).
alcohol glycerol  In animals
 If a triglyceride has more saturated FA attached to glycerol,  Major storage and transport form of FA
it is solid at room temperature such as animal fats.  Insulation in low temperatures
 If it contains more of unsaturated FA, it is liquid at room  Makes fur and feathers water-repellent
temperature such as vegetable oil.  In plants
 They are also called neutral fats, because the carboxyl  Energy reserve in fruits and seeds
groups of the fatty acids are bound in ester linkage and can  natural soaps are prepared by boiling triglycerides (animal
no longer function as acids therefore it will not be ionized fats or vegetable oils) with NaOH in a reaction called
saponification (Latin, sapo, soap)
and will not become anion. The fatty acid moiety in lipid
esters is known as an acyl group.
 TAG mixtures are referred to as fats or oils
 Fats= which are solid at room temperature, contain a large
proportion of saturated fatty acids
 Oils = are liquid at room temperature because of their
relatively high unsaturated fatty acid content

Triacyglycerides: All three OH groups of Glycerol are Esterified

Mono or Diglycerides: Only one or two OH groups of Glycerol are
esterified by Fatty Acids.

Triglycerides when acted upon by NaOH( sodium hydroxide) it will be

converted to Sodium the process is Alkaline Hydrolysis or
Saponification,in vitro. On the other side, when triglycerides are acted
upon by Lipase enzyme, it will be ionized and the process used is
enzymatic hydrolysis, in vivo.

Soaps are used to remove dirt. Soap molecules have the non polar
alkyl chain interacting with non polar hydrophobic tail reacting with
Fig. 8-2, p. 195
one another while the hydrophilic head, the carboxyl with sodium
interacts with water to remove the dirt forming a micelle.

Waxes
 A complex mixture of esters of long-chain carboxylic acids
and alcohols.
 It is harder than fats.
 Main significance is to act as protective coatings for plants
and animals making leaves shiny
 Waxes are complex mixtures of nonpolar lipids
 Well-known examples of waxes include carnauba wax,
produced by the leaves of the Brazilian wax palm, and
beeswax

7|Hazel A. Perilla,RN
 •The predominant constituent of carnauba wax is
the wax ester myricyl cerotate. Triacontanoyl
palmitate is one of several important wax esters
in beeswax
 Waxes also contain hydrocarbons, alcohols, fatty acids,
aldehydes and sterols (steroid alcohols).
COMPLEX LIPIDS
 Aside from glycerol and fatty acid, there will be an additional
group e.g. phospholipids, glycosphingolipids
SCEMATIC DIAGRAM OF SIMPLE AND COMPLEX LIPIDS
 Phospholipids contain Phosphate
 Glycolipids contain sugar
SIMPLE AND COMPLEX LIPIDS
COMPLEX
SIMPLE
PHOSPHOLIPIDS
PHOSPHOGLYCERIDES SPHINGOLIPIDS
FA FA
SPHINGOSINE
GLYCEROL
FA
PO4 ALCOHOL
PO4
ALCOHOL
 When one alcohol group of glycerol is esterified by a
phosphoric acid rather than by a carboxylic acid,
phosphatidic acid produced
 Phosphoacylglycerols (phosphoglycerides) are the second
most abundant group of naturally occurring lipids, and they
are found in plant and animal membranes
 Phosphoglycerides are composed of 2 fatty acids, also has a
glycerol backbone, phosphate group and alcohol.
 Phosphoglyceride molecules are classified according to
which alcohol becomes esterified to the phosphate group:
 Phosphatidylcholine (PC or Lecithin)
 the alcohol is choline
 phosphatidylethanoalmine (PE)
 ethanolamime
 Phosphatidylserine (PS)
 serine
 diphosphatidylglycerol (dPG/ cardiolipin)
 phosphatidylyglycerol
 phosphatidylinositol (PI)
 Inositol
 There are two types of Phospholipids:
 Glycerophospholipids (phosphoglycerides)
 Sphingolipids( sphingomyelins)
 In glycerophospholipids, the alcohol backbone is
glycerol
 In Sphingolipds, the alcohol backbone is
sphingosine. Sphingosine + FA = Ceramide
 Phosphatidic acid (glycerophosphoglyceride) is considered
as the parent compound composed of glycerol, FA &
phosphate without the alcohol.
8|Hazel A. Perilla,RN
 A derivative of phosphatidylinositol, namely phosphatidyl-
4,5-bisphosphate (PIP2), is found in only small amounts in
plasma membranes.
 PIP2 is now recognized as an important component of a
second messenger system
 The most common fatty acids in the phosphoglycerides have
between 16 and 20 carbons
 Saturated fatty acids usually occur at C-1 of glycerol
 The fatty acid substituent at C-2 is usually unsaturated
 To make a special phsopholipid, alcohol must be linked.
GLYCOLIPIDS
In a phosphatidylglycerol/cardiolipin : 2 phosphate, 3 glycerol & 4 FA
If you remove 1 FA, that phospholipid becomes a lysophospholipid.
Lyso means one.
Biological importance of Phospholipids
 Lecithin or phosphatidylcholines or surfactants or surface-
acting agents
 To increase pulmonary compliance
 Compliance is the ability of lungs and
thorax to expand.
 To prevent atelectasis (collapse of the lung) at the
end of expiration
 play an essential role in reducing surface tension in
lung alveoli
 Respiratory distress syndrome (RDS) or Hyaline
membrane disease of the newborn, which is
common in premature infants, results from a lack
of this surfactant in the lung. Normal term is 38-42
weeks.
 Decreased Pulmonary Compliance is usually seen
in this disease where alveoli (in the Lungs) are
collapse due to strong surface tension secondary
to reduced or absence of surfactants- usually fatal.
 To predict the likelihood of RDS in high-risk
pregnancies, obstetricians commonly perform
amniocentesis for laboratory determination of the
ratio of phosphatidylcholine (lecithin) to
sphingomyelin in the amniotic fluid (L/S ratio)
 The higher the L/S ratio, the more surfactant is
present to allow the lung to expand normally.
 Normal L/S ratio is 2:1, 2 Lecithin:1 sphingomyelin
 Treatment for RDS born babies, may give Lecithin
surfactant by endotracheal nebulization.
 If the baby is still inside the womb, mother will be
given steroids to stimulate the maturation of fetal
lung.
  Serologic test for syphilis, the Venereal Disease Research
Laboratory (VDRL) test, utilizes cardiolipin, a diphosphatidyl
glycerol as the antigen
 They can serve to cement lipids to membranes and
lipoproteins to the polar proteins and carbohydrates. It is a  With repeating 5-carbon units (isoprene)
form of attachment with other macro molecule.  Types: terpenes and steroids

TERPENES
Monoterpenes 2 isoprene units
 Geraniol in oil of geranium
 Ceramide is the parent compound of sphingolipids which is Sesquiterpenes 3 isoprene units
a combination of sphingosine & FA.  Farnesene in oil of citronella
Diterpenes 4 isoprene units
 Phytol, a plant alcohol
 Squalene, in shark liver oil
Triterpenes 6 isoprene units
 Olive oil and yeast
Tetraterpenes 8 isoprene units
 Carotenoids (precursor of Vit A)
Polyterpenes bet. 3,000 and 6,000 units
 Natural rubber

Note* their difference is on the number of isoprene units but they are
the same with 5 –carbon units.

 Several important biomolecules are composed of

 There are four general classes of Sphingolipids:
a. Sphingomyelin b. Globosides
c. Cerebrosides d. Gangliosides
CERAMIDES
 consist of a fatty acid bound to sphingosine
 In humans, ceramides function principally as intermediates
in the synthesis of other sphingolipids
SPHINGOMYELIN
 By joining phosphoalcohol choline phosphate or
ethanolamine phosphate to ceramide, one generates the
sphingomyelin.
 Important components of the myelin sheath surrounding
the fastest conducting fiber for nerve conduction or neural
transmission in the central nervous system.
CEREBROSIDES
 They consist of a hexose sugar monosaccharide, such as
glucose or galactose, bound to a ceramide.
 These ceramide-monosaccharides are also part of the
myelin sheath.
GLOBOSIDES
 Oligosaccharide attached to ceramide
 Take part in the ABO incompatibility, the A antigen & the B
antigen
GANGLIOSIDES
 Consist of ceramide bound to an oligosaccharide that
contains an acidic sugar such as N-acetylneuraminic acid or
sialic cid.
SULFATIDES
 Are sulfated cerebrosides, or cerebroside-sulfate esters.
nonterpene components attached to isoprenoid groups
(often referred to as prenyl or isoprenyl groups)
 Examples of these biomolecules, referred to as mixed
terpenoids, include vitamin E ( α-tocopherol), ubiquinone,
vitamin K and some cytokinins ( plant hormones)
STEROIDS
 The third major class of lipids is the steroids, which are
compounds containing this ring or cyclic system
 Complex derivatives of triterpenes
 All with 4 fused rings
 Distinguished by placement of C-C double bonds and other
substituents (hydroxyl, carboxyl, alkyl)
 CYCLOPENTANOPERHYDRO-PHENANTHRENE is called the
steroid nucleus or the ABCD ring. There are three fused
cyclohexane rings (A, B ,C) connected in the same way as in
phenanthrene and joined to a cyclopentene ring (D).
 They are found in all eukaryotes and a small number of
bacteria.
 Cholesterol is mainly animal in origin. If you have
hypercholesterolemia, avoid red meats such as
chicken,pork, beef eat fruits and vegetables.
 80% of cholesterol in our body are produced endogenously
while 20% is from the diet.
 Cholesterol, an important molecule in animals, is an
example of the steroids. In addition to being an essential
component in animal cell membranes, cholesterol is a
precursor in the biosynthesis of all steroid hormones,
vitamin D, and bile salts
SEX HORMONES
• Androgens: male sex hormones
 synthesized in the testes
 responsible for the development of male
secondary sex characteristics
 Testosterone

9|Hazel A. Perilla,RN
 • Estrogens: female sex hormones  Females also have testosterone because there’s a way to
 synthesized in the ovaries convert cholesterol to testosterone but only in small
 responsible for the development of female amounts
secondary sex characteristics and control of the  The peripheral source of Estrogen is the adipose tissues.
menstrual cycle  Obese people experience less symptoms of menopause; hot
Animal Steroids flashes, irritability because you still have the extra source of
estrogen and obese people are known to have longer life
CH3
CH3 span.
C D
A B  Obesity paradox- when you reach 50, reserve your fats so
HO
CHOLESTEROL FREE CHOLESTEROL that you still have an extra source of estrogen.
OH OH OH
CH3 CH3 CH3
CH3 CH3 CH3
O
ANDROGENS
HO O
 This Steroid is produced in the adrenal cortex and the testes
O
TESTOSTERONE ESTROGEN PROGESTERONE FREE CHOLESTEROL  Having19 carbon atoms (Carbons 18 and 19 are in methyl
groups)
 Testosterone is one of the more potent androgen
The difference between free cholesterol & cholesteryl ester:  Dehydroepiandrosterone (DHA), unlike testosterone, is a 17-
ketosteroid
 Free cholesterol  Testosterone is the main hormone for sex libido/ sexual
 has this –OH group at C3 urge.
 amphiphatic cholesterol
 The OH group is polar region while the rest is non Animal Steroids
polar.
 If this will be attached to FA that makes it non
CH3
polar CH3 C D

 It is the cholesterol found in the cell membrane A B

HO
CHOLESTEROL FREE CHOLESTEROL

 Cholesteryl ester OH OH OH

 the –OH is esterified with FA.

CH3 CH3 CH3 O
CH3 CH3 CH3

 Purely non polar HO O

O
TESTOSTERONE ESTROGEN PROGESTERONE

Animal steroids have the same structure but differ only in side chain,
either longer or shorter. Thru side chain cleavage, cholesterol can be
converted to other steroid hormones.

PROGESTERONE
 Synthesized in the corpus luteum, has 21 carbons, as do the
adrenocortical steroids such as corticosterone and cortisol
 Corpus Luteum matures in egg cell,ovary
Cholesterol 27 C atoms  Male has no progesterone
Testosterone 19 C atoms  Progesterone has an acetyl group joined at carbon 17
Estradiol (estrogen) 18 C atoms
Progesterone 21 C atoms BILE ACID
 It is the end product of cholesterol degradation.
These hormones are produced thru a reaction known as side chain  It is secreted into the bile to emulsify dietary fats
cleavage SCC, just cut the side chains and it will be converted to  The major bile acid is Cholic acid
different steroid hormones.
The adrenal cortex which is located at the top of each kidney also
Only foods of animal origin contain cholesterol. Consequently, grians, produces hormones. The Cortisol hormone which is produced by
vegetables,legumes & fruits provide no cholesterol. Eggs contain high glucocorticoids increases the blood glucose. Another hormone is
amounts of cholesterol. Recommended eggs per week must be 3-4 Aldosterone produced by Mineralocorticoid is responsible for water
eggs only. and Na retention. The AldehydeKeto group is possible for the
glucocorticoid effect and mineralocorticoid effect.
ESTROGEN= “OVARIAN STEROID”
 Contain 18 carbon atoms (Carbon 18 is found in a methyl
group)
 Unlike other steroids, the A ring of the steroid nucleus of
estrogen is aromatic.
 Estradiol has OH groups attached to carbons 3 and.17.

10 | H a z e l A . P e r i l l a , R N
  After a fatty meal, the blood appears milky due to the high
concentration of chylomicrons
 Heparin, an anticoagulant, also helps to clear chylomicrons
from the blood, perhaps by stimulating lipoprotein lipase.
Lipoproteins are transport proteins. The major non polar lipids in our
body are cholesteryl ester and Triglyceride. Because they are non
VLDL
polar they are insoluble in the blood so they need Lipoproteins for
 Contains a lot of triglyceride. It is smaller than chylomicron.
them to be transported from one organ to another organ. Lipid must
 It is produced in the liver and it is responsible for
bind to proteins to make them water soluble for transport in the
endogenous transport.
blood. For free fatty acids, its transport protein is Albumin.
 It is also called pre β Ipoprotein because of its
electrophoretic mobility.
Two laboratory techniques are used to separate lipoproteins from one
another:
LDL
 It contains more of cholesterol. It is responsible for the
Ultracentrifugation
transport of cholesterol from the liver to the different
 Separates them according to their differing densities,
tissues.
Chylomicron, HDL, LDL ,VLDL
 If you have a lot of LDL that stays in the blood for a long
 Chylomicron is the least dense, lightest lipoprotein
time, it will be oxidized then it will be deposted to tunica
Electrophoresis
intima of the arteries causing atherosclerosis. “ Bad
 separates them on a basis of their varying
cholesterol”
 There’s a movement of molecule because of net charges
 The migration of LDL is similar with β globulin so that’t the
reason why LDL is called β Lipoprotein.
Chylomicron contains mainly of Triglyceride. Triglyceride is also called
“neutral fats”. Since it is neutral fats, it contains triacylglycerol which
HDL
has no net charge, no movement for chylomicron, VLDL, LDL & HDL
 It contains more of cholesterol. It has the highest content of
contains protein so they can migrate. The migration of LDL is similar
protein. Since it has the highest content of protein, it is the
with β globulin so that’t the reason why LDL is called β Lipoprotein.
heaviest lipoprotein but it is smallest.
HDL migration is similar with α globulin. Another name for HDL is
 It acts as a scavenger removing excess cholesterol from the
αLipoprotein. Another name for VLDL is pre β Lipoprotein.
tissues back to the liver then it is converted to bile acid. “
Good cholesterol”
Lipoprotein lipase hydrolyzes triglycerides bound in lipoproteins such
as chylomicrons and VLDL, yielding monoglycerides and free fatty
BIOLOGICAL MEMBRANE
acids.
It is composed of a bilipid layer. It contains a hydrophobic non polar
tail & a hydrophilic polar head. It is responsibke for the semi
permeability of the cell membrane so not all substances can pass
because of the bilipid layer.

The presence of cholesterol is a characteristic of animal rather than

plant membranes. Animal membranes are less fluid than plant
membranes. The presence of saturated fatty acid in the membrane
makes it less permeable more rigid but in the presence of unsaturated
fatty acid that makes the membrane more permeable especially if the
This is the structure of Lipoprotein.
unsaturation is –cis because the kink increases the fluidity of the cell
Outer core is composed of Polar surface envelope amphiphatic lipids
membrane.
such as phospholipids, free cholesterol & apolipoproteins. The
charged and polar residues on the surface of a lipoprotein enable it to
dissolve in blood.
Inner core is composed of Non polar lipids, Neural Lipid core such as
Cholesteryl ester & Triglyceride. The inner part is color yellow because
it contains fats.

All these lipoproteins will differ based on their content. If it has more
of triglyceride, it is either Chylomicron or VLDL. If it contains more of
cholesteryl ester it is more of HDL & LDL.
The polar head includes glycerol, phosphate & alcohol. The 2 fatty
acids are the non polar lipid. If it is saturated, it is straight while
CHYLOMICRON
unsaturated FA has a kink. Lipid-soluble substances (i.e. O2, CO2,
 It contains triglyceride, less protein. Since it has more of fats,
steroid hormones) readily cross the cell membrane
in the ultracentrifugation, it floats.
 It is produced in the intestines and it is responsible for
Amphipathic Lipid
exogenous transport of triglycerides.
Hydrophilic: “water-loving” polar head group
 It is the lightest but the biggest lipoprotein.
Hydrophobic: “water-hating” non-polar tails

11 | H a z e l A . P e r i l l a , R N
  Chain reaction producing continuous supply of free radicals
What makes up the cell membrane? that initiate peroxidation are; Initiation, Propagation &
Termination.
 Malondialdehyde is the one measured for Lipid
Lipids Proteins Carbohydrates
peroxidation. It is a sign that you are producing free radicals.
 If there is a high intake of polyunsaturated FA, you must also
have an intake of Vit E because it is a good antioxidant.

CLASSES OF ANTIOXIDANTS

 Preventive antioxidants
 Reduce the rate of chain initiation
The polar region of free cholesterol is the OH group attached to C3.  Examples: Catalase, Chelators of metal ions;
That‘s the only polar region in cholesterol while the rest, ABCD ring is DTPA(diethylenetriaminepentaacetate),EDTA(ethylene
non polar. Unsaturated FA increases the membrane fluidity. Higer diaminetetraacetate)
temperature increases the fluidity & permeability of the membrane.  Chelation process is the removal of excess iron because
iron participates in Lipid peroxidation.
COMPOSITION OF DIETARY FATS
 Chain-breaking antioxidants
• Mixture or fatty acid derivatives
 Interfere with chain propagation
 Examples: Phenols, Aromatic amines, Vit E , C,
• Fats from animals have more saturated fats than from
plants glutathione
• Saturated FA ↑ HDL, ↑ LDL
 In vivo, superoxide dismutase which acts on aqueous
• Mono-UFA ↑ HDL, ↓ LDL
phase to trap superoxide free radicals (O-o)
 Peroxidation is also catalyzed by heme compounds and
• PUFA maintains HDL, ↓ LDL
by lipooxygenases found in platelets and leukocytes
• Trans FA ↓ HDL, ↑ LDL

Oleic acid is cis double bond on the same side while Elaidic acid is AMPHIPHATIC LIPIDS
trans double bond on the opposite side. Oleic acid increases the  Oriented at oil-water interface with polar at water phase,
permeability of the membrane because cis unsaturation increases the non-polar at oil phase
permeability.
a. Biologic membrane - lipid bilayer
Olive oil monounsaturated b. Micelles -polar lipids in an aqueous solution or medium
Beef monounsaturated, high in c. Liposomes - lipid bilayer forming a vesicle by sonicating an
saturated amphipathic lipid. It serves as carrier of anti-cancer drugs because
Milk saturated there are anti cancer drugs that are hydrophilic so it can be delivered
Corn Oil polyunsaturated to target cell by enclosing it into Liposomes.
Palm Oil Palmitic acid; contains Oleic d. Receptors - tissue-specific antibodies
Soybean, Safflower & Sunflower oil polyunsaturated e. Emulsions - larger particles, formed by non-polar lipids in an
aqueous medium stabilized by emulsifying agents such as polar lipids
(lecithin)
The Truth about Fats
Micelle & water emulsion the inner part is Hydrophobic compared to a
• All fats are not bad fats
• Impt. roles in human body,sorrounding every cell in the Liposome the inner part is Hydrophilic. Liposome is derived from
human body,involved in proper development of the CNS, phospholipids such as soya beans, egg yolk.
energy production and storage, oxygen transport and
regulation of inflammation
• 3 types of fats: -end-
– Saturated fats – solid at room temp. Lard,beef fat,butter,and
Coconut have high saturated fat percentages( 41,44,66,92%
respectively). Inc. cholesterol and CVD
– Monounsaturated fats- liquid at room temp.,olive oil,
nuts,avocado,sunflower oil
– Polyunsaturated fats – greatest nutritional benefits, but on the
other hand, make these fats more susceptible to rancidity and
chemical conversion to unhealthy fats.

LIPID PEROXIDATION

 Polyunsaturated FA increases HDL & LDL but unfortunately

Lipid peroxidation is prone to Lipid peroxidation.
 Peroxidation- exposure of lipids to O2
 Causes deterioration of food (rancidity) & may cause tissue
damage leading to cancer, inflammatory diseases,
atherosclerosis, aging, etc. because it generates free radicals

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