CHAPTER 21

Fats

Special Topics in Bioactive Natural products Class

Teacher : Dr. Cheng Ta-Chih

Presented by
Soni Andriawan
M10522023

1 Chapter 1 Author : T.O. Elufioye and S. Badal 12/9/2018

 Chapter Outline
21.1 Introduction 21.4 Nutraceutical Applications
21.2 Classification of Lipids 21.4.1 Fish Oils
21.2.1 Fatty Acids—Components 21.4.2 Bird Oils
of Acylglycerols 21.5 Pharmaceutical Applications
21.2.2 Cholesterol 428 21.5.1 Phospholipids
21.2.3 Vitamin D 428 21.6 Fats and Health
21.3 Extraction of Animal Fats 21.6.1 Saturated Fats
21.3.1 Rendering 21.6.2 Long-Chain PU Fatty
21.3.2 Oil Refining Acids
21.3.3 Extraction of Marine Oils 21.7 Conclusion

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 6.1 Background
1. Fats, small molecules present within living tissue, are comprised
mainly of glycerol esters of fatty acids, triacylglycerols (TAGs)
being the predominant components.
2. Fats are commonly described based on their source,
Example:
a) Fish oil,
b) bird oil,
c) and pork fat (lard),
d) and belong to the general class of compounds called lipids, which
may be classified based on their composition, origin, and nature.
3. Lipids encompass a diverse range of compounds that are generally
nonpolar or water-insoluble, and are derived from living organisms.

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 6.1 Background
3. Lipids include:
a) glycerides (such as mono-, di-, and TAGs),
b) phospholipids,
c) prostaglandins,
d) steroids,
e) carotenoids,
f) and waxes.
Similar to carbohydrates and proteins, fats represent a
significant proportion of the constitution of living
organisms.

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 6.1 Background
5. Lipids are present in all organs of animals and are also
present as depositions in various places within organisms.
Larger amounts of fats are associated
a) connective tissue,
b) adipose tissue,
c) bone marrow,
d) brain,
e) liver,
f) and about the kidneys.
Fat, in addition to protein, is a major component of whole
milk powder.

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 21.2 CLASSIFICATION OF LIPIDS
There are various classifications of lipids that exist in
living tissue.
According to Bloor in 1920, lipids are divided into three groups:
1. Simple lipids (comprised of fats and waxes),
2. Compound lipids (inclusive of phospholipids and glycolipids),
3. and derived lipids (inclusive of fatty acids, glycerol, and sterols,
with cholesterol, bile acids, and vitamin D being examples of
animal sterols).

Simple lipids are further divided into neutral fats or

acylglycerols and waxes. The term neutral fats is generally used to
describe fatty acid esters of glycerol.

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 21.2 CLASSIFICATION OF LIPIDS
21.2.1 Fatty Acids—Components of Acylglycerols
1. Fatty acids may be termed, short, medium, long, or very
long-chained based on the number of carbons (2-4, 6-10,
12-18, and 20-24 carbon atoms, respectively).
2. Naturally occurring fatty acids generally have an even number of
carbons arranged in a straight chain with most having 14-24
carbons present.
3. Fatty acids may also be described as saturated (having no carbon-
carbon double bonds) or unsaturated.
a. One C=C double bond are called monounsaturated (MU),
b. possessing two or more being described as polyunsaturated
(PU).

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 21.2 CLASSIFICATION OF LIPIDS
21.2.1 Fatty Acids—Components of Acylglycerols

Double bonds in fatty acids naturally

occur in the cis-configuration and are
separated by a methylene (i.e., CH2)
group.

Trans fats such as conjugated

linoleic acids (CLA) found in
ruminant fats.
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 21.2 CLASSIFICATION OF LIPIDS
21.2.1 Fatty Acids—Components of Acylglycerols

Trans fats are uncommon in nature, with the

exception of ruminant fat (including cows and sheep),
which contains vaccenic acid as the main trans fatty
acid, produced as a result of incomplete
biohydrogenation of linoleic and linolenic acids by
microorganisms in the rumen.

Trans fatty acids from industrial sources are

known to lower high-density lipoprotein
cholesterol (HDL-C), raise low-density
lipoprotein cholesterol (LDL-C), and increase
the risk of coronary heart disease (CHD).

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 21.2 CLASSIFICATION OF LIPIDS
21.2.1 Fatty Acids—Components of Acylglycerols
The major trans fat in partially hydrogenated
vegetable oil products is elaidic acid, whereas trans
isomers of C20:1, 20:2, 22:1, and 22:2 are found in
partially hydrogenated products from marine origin.

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 21.2 CLASSIFICATION OF LIPIDS
21.2.1 Fatty Acids—Components of Acylglycerols
Although the effects of trans fatty acids from natural
sources are less clear, some research suggest that all
trans fats have a similar effect on plasma cholesterol
levels.

Saturated fatty acids

(SFAs)
• Having 10 or more
carbon atoms
• Dominant feature in
animal fats than plant
oils, with unsaturated
fats being more
prominent in plant oils.
Chapter 1
11
Unsaturated fatty acids
• less than 10 carbon
atoms,
• Long-chain omega-3
fatty acids are
characteristically found
in large amounts in fish
oils compared to fats
from terrestrial animals.
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 21.2 CLASSIFICATION OF LIPIDS
21.2 Fatty Acids

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 21.2 CLASSIFICATION OF LIPIDS
21.2.1 Fatty Acids—Components of Acylglycerols

Phospholipids
1. The most abundant type of lipid
constituents in cell membranes,
2. their chief role involving
structural integrity of the
membrane bilayer.

3. The phosphate is then linked to a simple, polar organic

molecule.
4. The majority of phospholipids are comprised of a
diacylglycerol, a phosphate group, and a simple organic
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 21.2 CLASSIFICATION OF LIPIDS
21.2.1 Fatty Acids—Components of Acylglycerols
Phospholipids

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 21.2 CLASSIFICATION OF LIPIDS
21.2.1 Fatty Acids—Components of Acylglycerols
Phosphatidylcholine (PC) (include into Phospholipids)
1. often referred to as lecithin,
2. is the most abundant class of lipids in animal cell membranes,
accounting for nearly half of the total.
3. PC is the main plasma phospholipid and an important component
of lipoproteins, especially HDL.
4. PC is the biosynthetic precursor of phosphatidic acid,
lysophosphatidylcholine platelet-activating factor, and
phosphatidylserine.
5. Source: soy and egg yolk

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 21.2 CLASSIFICATION OF LIPIDS
21.2 Fatty Acids

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 21.2 CLASSIFICATION OF LIPIDS
21.2.2 Cholesterol
1. Is the most dominant sterol in animal fats and oils, being present
in vegetable oils in negligible amounts,
2. Has a number of important biological roles and is required for
human life and health.
3. Water insolubility, cholesterol has to be combined with water-
soluble proteins in order to be transported in the body, thereby
forming lipoproteins.
4. These lipoproteins (e.g., HDL and LDL) have been associated
with much controversy as it relates to their relationship with
cardiac health.

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 21.2 CLASSIFICATION OF LIPIDS
21.2.2 Cholesterol
5. Effects
a) Negative effect
1) High levels of cholesterol in the blood can lead to the development
of atherosclerosis, and has been associated with a myriad of health
problems.
“For this reason, cholesterol is considered “bad” by the masses.”
b) Positive effect
1) Include modulation of membrane fluidity and permeability,
2) Maintenance of the structural integrity of membranes,
3) Development and functioning of central nervous system,
4) sperm development, and embryonic development.
5) Additionally, it is a precursor in the biosynthesis of vitamin D,
steroid hormones, and bile acids.

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 21.2 CLASSIFICATION OF LIPIDS
21.2.3 Vitamin D
The fat-soluble vitamin D (cholecalciferol) is known mostly
for its role in calcium and phosphorus metabolism, and, by extension,
bone development and the prevention of rickets.

Sources:
 Humans and other animals naturally produce this vitamin (from
cholesterol) in their skin upon exposure to sunlight.
 It may also be obtained from the diet (only small amounts are
naturally present in most foods) or dietary supplements.
1. salmon,
2. sardines, and herring,
3. beef,
4. eggs,
5. and fortified foods, such as cereal and milk.
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 21.3 EXTRACTION OF ANIMAL FATS
Over the last decade the total production of oils
and fats has grown

50%

>5%

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 21.3 EXTRACTION OF ANIMAL FATS
Oil application:
1. used for human consumption,
2. the major applications being for fuel, animal feed, soap,
oleochemicals, and pet food.

 There are many types of animal fats, the most commonly used
for culinary purposes being pork lard.
 The only animal fat that has significant application for the
promotion or maintenance of health is fish oils.
1) Menhaden, for their oil and
2) anchovy, fishmeal.
3) capelin,
4) sardines,
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1 and jack mackerel 12/9/2018
 21.3 EXTRACTION OF ANIMAL FATS
Oil Extraction Steps:
1. Rendering
Depending on the physical state of the animal fat
to be extracted (dried or wet), dry or wet rendering is
applied, respectively.
a. wet rendering
1) crushed and minced
2) heat at 70-90 C.
3) fat is obtained by separation of the liquid phase via a
decanter, which utilizes centrifugal force.
4) The solid phase is drained, pressed, and dried.
b. dry rendering (without heating)

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 21.3 EXTRACTION OF ANIMAL FATS
Oil Extraction Steps:
2. Oil Refining
a) Extracted crude food oils are a complex mixture
containing several classes of compounds including
1) glycerides,
2) free fatty acids,
3) sterols,
4) phospholipids,
5) pigments, and at times, toxic substances.
b) Oil refining is therefore required to remove impurities
to produce edible oils.

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 21.3 EXTRACTION OF ANIMAL FATS
Oil Extraction Steps:
2. Oil Refining (Processing)
a) Degumming (via addition of water)
Remove phospholipids and other substances such as
resins from the oil.
b) Neutralization (This results in a decrease in oil acidity.)
Removes free fatty acids, which form insoluble soaps
and are removed with the water fraction.
c) Washing with water
Removes remaining soaps and residual caustic, in
addition to oxidation products and trace metals.

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 21.3 EXTRACTION OF ANIMAL FATS
Oil Extraction Steps:
2. Oil Refining (Processing)
d) Bleaching
Removes pigments that cause undesirable colors or
promotes oxidation.Neutralization (This results in a
decrease in oil acidity.)
e) Winterization (This yields oils with a greater percentage
of PUFAs),
Involves storing the oils at low temperatures, which
results in the crystallization of waxes and the more
saturated TAGs, which have higher melting points.

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 21.3 EXTRACTION OF ANIMAL FATS
Oil Extraction Steps:
2. Oil Refining (Processing)
f) Deodorization, the finishing step, effects the removal of
g) volatile compounds with objectionable odors. This step
is particularly important in crude fish oils, in order to
reduce the fishy odor and improve sensory quality.

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 21.3 EXTRACTION OF ANIMAL FATS
Oil Extraction Steps:
3. Extraction of Marine Oils
The majority of fish oils are obtained from the flesh or body
of the fish, with menhaden being the major source.

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 21.3 EXTRACTION OF ANIMAL FATS
Oil Extraction Steps:
3. Extraction of Marine Oils (Addition process)
Various methodologies are currently employed for
producing highly purified omega-3 fatty acids, such as
1) Various physical,
2) chemical, and enzymic methods are utilized
3) And include urea adduction, chromatography, rapid
solidification

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 21.4 NUTRACEUTICAL APPLICATIONS
1. Function:
a) promote health,
b) prevent disease,
c) and are considered as semimedicinal.
2. Various nutraceuticals are available commercially.
3. Benefically:
a) to the heart,
b) also referred to as cardioprotective nutraceuticals, include omega-3
fatty acids, vitamins, minerals, antioxidants, and dietary fibers.
4. Their mode of action
Serve as biochemical metabolites, directly intervening in intermediary
lipid metabolism, or regulating proteins of the vascular system

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 21.4 NUTRACEUTICAL APPLICATIONS

Fish oil Bird oil

• Omega-3 fish oil is • possesses potent anti-

considered as a nutraceutical, inflammatory activity and has
• exhibiting anti-inflammatory been utilized in the
activity, treatment of various
• protection from age-related inflammatory conditions such
macular degeneration (a as mucositis, inflammatory
common eye ailment), bowel syndrome, and
auricular inflammation.
• and hypocholesterolemic
activity. • has significant
hypocholesterolemic and
antiatherosclerotic activities
Bird oil: In the USA, the emu, ostrich, and rhea
Chapter 1
Fish oil: tuna, sardine, mackerel, herring, anchovy, menhaden,
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cod, or salmon
 21.5 PHARMACEUTICAL APPLICATIONS
21.5.1 Phospholipidspromote health
The application of phospholipids in pharmaceuticals is
linked mainly to their powerful emulsifying properties.
1. Enhanced permeability of drug through the dermis
2. Delivery of large and diverse drugs, e.g., peptides and
proteins
3. Safe composition
4. Approved for cosmetic and pharmaceutical applications
5. Low-risk profile
6. Toxicological properties of phospholipids have been well
documented
7. High market attraction

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 21.5 PHARMACEUTICAL APPLICATIONS
21.5.1 Phospholipidspromote health

1. Liposomes: used as therapeutic tools in tumor targeting, topical applications, genetic vaccination
2. Ethosomes: provide enhanced delivery through the skin
3. Phytosomes: contain active ingredient surrounded by the phospholipid producing better absorption
of herbal products
4. Transferosomes: transdermal drug carriers
5. Long circulating liposomes: modification of liposomes with lipids to increase circulation time
6. Nanocochelates: consist of at least 75% soy-based phospholipid and a multivalent cation
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 21.6 FATS AND HEALTH
Compared with other food groups, the relationship that exists
between fats and health is probably one of the most controversial.
 This section will summarize the currently held views on the effect of
selected types of fats on health.
Example case:
1. High levels of omega-3 fatty acids are known to have a protective effect
against a number of degenerative diseases, including cardiovascular
disease and diabetes.
2. Almost 80% of deaths due to noncommunicable diseases (NCD) occur in
low- and middle-income countries
3. More than 58 million Americans have at least one form of cardiovascular
disease—stroke, hypertension, or CHD.
4. One in nine women, and one in six men aged 4564 have some form of
heart disease.

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 21.6 FATS AND HEALTH
21.6.1 Saturated Fats
In fact : Although much association has been made about the negative effect of
high dietary SFAs on cardiovascular health, the scientific evidence of
this is lacking.
Effect : (Positive)
1. Many of the shorter-chain fatty acids found in milk fat and coconut
oil have positive effects on health.
2. They provide 10% less calories compared to long-chain fatty acids
(i.e., 8.3 vs 9 cal/gram), are more rapidly absorbed and burned as
fuel, are stored in fat deposits to a much lesser extent than long-
chain fatty acids, and enhance thermogenesis.
3. they are oxidized by the liver to ketone bodies, which serve as an
alternative energy source.
4. The shorter-chain SFAs in milk (C4C12) are rapidly metabolized for
energy in infants.
5. Lauric acid is effective in preventing tooth decay and plaque buildup

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 21.6 FATS AND HEALTH
21.6.1 Saturated Fats
In fact : Although much association has been made about the negative
effect of high dietary SFAs on cardiovascular health, the
scientific evidence of this is lacking.
Effect : (Negative)
1. Fifty percent of the cholesterol-elevating effect of myristic acid
is actually due to its effect on HDL-C.
2. The medium-chain SFAs in coconut oil and butterfat (milk)
increase total serum cholesterol, but their positive effects on
HDL-C are protective in many ways.
3. they are oxidized by the liver to ketone bodies, which serve as
an alternative energy source.

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 21.6 FATS AND HEALTH
21.6.2 Long-Chain PU Fatty Acids
PU fatty acids are generally considered to be good for health,
1. playing vital roles in the prevention of cardiovascular complications,
2. osteoarthritis,
3. diabetes,
4. hypertension
5. and autoimmune diseases.
Omega-3 and omega-6 PUFA
1. Increased interest in the potential beneficial health effects, particularly of
omega-3 fatty acids,
2. Omega-3 PUFAs are important for the prevention of cardiovascular
disease and the control of LDL cholesterol.

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 21.6 FATS AND HEALTH
21.6.2 Long-Chain PU Fatty Acids
Omega-3 (especially EPA and DHA)
1. Omega-3 fats protect against blood clots, irregular heartbeats, and
high blood pressure.
2. They are associated with proper mental function, growth, and
development, as well as other beneficial properties such as
antiinflammatory, hypolipidemic, antithrombotic, and vasodilatory
properties.
3. EPA and DHA are both commonly found in marine oils (fish oils,
egg oil, squid oils, krill oil).

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 21.7 CONCLUSION
1. Fats—the small and intriguing biomolecules—will continue to be the
subject of wide and varied research for a long time to come.
2. Their important place in the nutraceutical and pharmaceutical arenas is
well established. So what is the conclusion of the matter as far as the
relationship between fats and health is concerned? It is this: fats are a
requirement for health, and inappropriately balanced consumption of the
various types of fats may, on the other hand, be detrimental to health.
3. The topic remains a controversy. Much has been reported about the
health benefits of PUFAs. However, clear distinctions should be made in
discussing PUFAs, as n-3 and n-6 PUFAs have different effects on health,
though both are necessary for the promotion of health. The crucial thing
is the maintenance of diets comprised of an appropriate balance of fats in
appropriate quantities, and for those foods to be prepared using methods
that minimize fat degradation
4. One must bear in mind also that “one size does not fit all,” when it comes
to the composition and amounts of fats in the diet are considered, as
variables such as age, metabolic rate, health status, and physical activity
result in different requirements for different sets of people.

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