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Acknowledgements

My sincere thanks to Dr.T.Madujit for conducting this course and providing us an opportunity to
search about a current topic which is interesting and knowledge based. His guidance to make this
manuscript a success is immense. And I take this as an opportunity to thank all who guided and
helped to prepare this article. The scientists all around the world who have done researches and
reviews earlier in this field also receive my humble salutations.
Abstract
Lipid is an ester which is made out of glycerol and fatty acid/s. These fatty acids can be saturated
or unsaturated ones. The unsaturated ones can be divided into monounsaturated fatty acids
(MUFA) and polyunsaturated fatty acids (PUFA) and have several nomenclatures according to
the number of carbon atoms in the chain, number of double bonds between carbon atoms and
their position from methyl end or carboxylic end.

The unsaturated fatty acids believed to be having lots of health benefits. Some benefits have been
proven but some not yet or evidences are inconclusive. In this article our main consideration is
focused on PUFA. Many dietary sources are discussed where PUFA are available in considerable
amounts. These sources can be classified as plant originated such as vegetable oils (e.g. maize,
sunflower, safflower and soybean oils) and animal meat, fish (e.g. mackerel, herring, salmon, tuna,
sardines) egg, milk. Basically these dietary sources contain n-3 or n-6 PUFA. Essential fatty
acids are Linoleic acid Alpha-linolenic acid and some of these provide the essential fatty acids
(EFA) for human.

Types of dietary sources and their consumption levels are discussed. The major roles of lipids
can be classified energy storage, energy providing, structural and metabolic functions and these
are elaborated. Health benefits of fatty acids are considered mainly. They can be acting against
some diseases and thought to have beneficial effects against diseases which have been and yet to
be proven are considered here. Diseases considered are coronary heart diseases (CHD),
atherosclerosis, thrombogenesis and fibrinolysis, blood pressure, cancer, diabetes, skin diseases
(such as atopic eczema and psoriasis), and immune disorders.
Introduction
Fatty acids are a component of lipids and made out of hydrocarbon chain. They can be classified
as saturated and unsaturated. This classification is according to the availability of C=C bonds and
their position in the chain of fatty acids. Unsaturation can be by a single C=C or many and
accordingly mono and poly unsaturated fatty acids are defined. Several categories of these fatty
acids are available and their nomenclature is going to be discussed. They can be named omega
(ω) or n and delta (∆) types. There are mainly omega 3,6 and 9 fatty acids.

The dietary sources and PUFA levels they contain are to be discussed. Dietary sources could be
plant or animal sources such as vegetable oils (e.g. maize, sunflower, safflower and soybean oils)
and animal meat, fish (e.g. mackerel, herring, salmon, tuna, sardines) egg, milk. EPA and DHA are
essential n-3 PUFA and they are available basically in the fish based foods. Composition in some
fish oils, intakes of EPA and DHA and percentage contribution from food groups by dietary
habit are to be discussed.

Major roles of PUFA are discussed they can be classified into energy storage, energy providing,
structural and metabolic roles.

They Dietary intake levels of some of these sources are found. Health benefits such as decreasing
or controlling some hazardous diseases are to be discussed some benefits have been proven but
some not yet or evidences are inconclusive. Diseases considered are coronary heart diseases
(CHD), atherosclerosis, thrombogenesis and fibrinolysis, blood pressure, cancer, diabetes, skin
diseases (such as atopic eczema and psoriasis), and immune disorders. Some may have fewer
amounts of references to discuss as the researches still in progress.
Types of poly unsaturated fatty acids (PUFA)
A fatty acid is made up of hydrocarbon chain of varying chain length with a methyl group one
end and carboxylic group at the other end. Number of carbons could vary from 2 to 30.
Commonly they have 12 to 22.The most number of fatty acids have straight chains of an even
number of carbon atoms.

If the carbon chain contain double bond/s those fatty acids are considered as unsaturated fatty
acids: and a fatty acid containing two or more double bonds is called poly unsaturated fatty acids
(PUFA). Most unsaturated fatty acids contain cis configuration rather than trans configuration
double bonds (these are mainly occurring in ruminant fats such as cow’s milk, in plant lipids and
in some seed oils). Normally PUFA are separated by a single methylene group are called as
divinylmethane pattern (7). In some PUFA, the double bonds are not seperated by a methylene (-
CH2-) group, but they are conjugated (-C-C=C-C=C-C- conjugated double bonds) (8) and some
unusual ones having polymethylene-interrupted or widely seperated polyenes (or non-methylene-
interrupted fatty acids). (-C=C-C-C-C-C=C-)

Saturated and unsaturated fatty acids both have systematic or chemical names and trivial names.
Systematic name derived from the number of carbon atoms in the acyl chain, the number of
double bonds, the position of the double bond which has been found by counting the carbonyl
carbon as carbon 1 and their configuration (Cis or Trans).A suffix enoic denotes that the fatty
acid is an unsaturated one and at the end of the chain there is a carboxylic group.

Short hand method relies upon identifying the number of carbon atoms in the chain, the number
of double bonds and the position of the double bond closest to the methyl carbon. Other than
these, they are often described with a common or trivial name.

Numbering could be started from the carbonyl carbon end (delta (∆) end) or methyl carbon
(omega (ω) or n terminal). If the numbering has been started from the latter, position of the first
double bond from the methyl end is given with the term omega (ω) or n.

If the first C=C is present at the 3rd, 6th or 9th carbon from the omega terminal the fatty acid is
called as omega-3 (ω-3), omega-6 (ω-6) and omega-9 (ω-9) respectively.

Human subjects cannot synthesize the simplest n-6 and n-3 PUFA. They are Linoleic acid (18:
2n-6) and Alpha-linolenic acid (18: 3n-3). So these are defined as essential fatty acids.
Table1.1: Omega-3 fatty acids (59)

Short hand
Trivial name Chemical name/ systematic name
notation

(16:3n-3) all-cis 7,10,13-hexadecatrienoic acid

Alpha-linolenic acid (ALA) (18:3n-3) all-cis-9,12,15-octadecatrienoic acid

all-cis-6,9,12,15,-octadecatetraenoic
Stearidonic acid (STD) (18:4n-3)
acid

Eicosatrienoic acid (ETE) (20:3n-3) all-cis-11,14,17-eicosatrienoic acid

all-cis-8,11,14,17-eicosatetraenoic
Eicosatetraenoic acid (ETA) 20:4 (n-3)
acid

all-cis-5,8,11,14,17-eicosapentaenoic
Eicosapentaenoic acid (EPA) (20:5n-3)
acid

Docosapentaenoic acid (DPA, all-cis-7,10,13,16,19-


(22:5n-3)
Clupanodonic acid) docosapentaenoic acid

all-cis-4,7,10,13,16,19-
Docosahexaenoic acid (DHA) (22:6n-3)
docosahexaenoic acid

all-cis-9,12,15,18,21-
Tetracosapentaenoic acid (24:5n-3)
tetracosapentaenoic acid

all-cis-6,9,12,15,18,21-
Tetracosahexaenoic acid (Nisinic acid) (24:6n-3)
tetracosahexaenoic acid
Table 1.2: Omega-6 fatty acids (59)

Short hand
Trivial name Chemical name/ systematic name
notation

Linoleic acid (18:2n-6) all-cis-9,12-octadecadienoic acid

γ-linolenic acid (GLA) (18:3n-6) all-cis-6,9,12-octadecatrienoic acid

Eicosadienoic acid (20:2n-6) all-cis-11,14-eicosadienoic acid

Dihomo-γ -linolenic acid (DGLA) (20:3n-6) all-cis-8,11,14-eicosatrienoic acid

Arachidonic acid (AA) (20:4n-6) all-cis-5,8,11,14-eicosatetraenoic acid

Docosadienoic acid (22:2n-6) all-cis-13,16-docosadienoic acid

Adrenic acid (22:4n-6) all-cis-7,10,13,16-docosatetraenoic acid

Docosapentaenoic acid (Osbond all-cis-4,7,10,13,16-docosapentaenoic


(22:5n-6)
acid) acid

Table 1.3: Omega-9 fatty acids, mono- and poly unsaturated (59)
Trivial name Short hand notation Chemical name/ systematic name

Oleic acid (18:1n-9) cis-9-octadecenoic acid

Eicosenoic acid (20:1n-9) cis-11-eicosenoic acid

Mead acid (20:3n-9) all-cis-5,8,11-eicosatrienoic acid

Erucic acid (22:1n-9) cis-13-docosenoic acid

Nervonic acid (24:1n-9) cis-15-tetracosenoic acid

Dietary sources of poly unsaturated fatty acids:


Fatty acids in fats, oils and food stuffs are mainly esterified to glycerol as tri acyl glycerides
(TAG), phospholipids, glycolipids and other lipids. Important dietary sources of the linoleic acid
include vegetable oils (e.g. maize, sunflower, safflower and soybean oils) and products made
from those oils (e.g. margarines). Oils like soybean, some nuts, flaxseeds and flaxseed (linseed)
oil also contain alpha-linolenic acid. Some seed oils contain moderate to high proportions of
relatively unusual fatty acids (e.g. γ-linolenic acid (18:3n-6) in borage (starflower) and evening
primrose

Meat is an important source of the very long chain (VLC) n-6 fatty acid, arachidonic acid (20:4n-
6). Fish can be classified into lean fish that store lipid as TAG in the liver (e.g. cod) or fatty/oily
fish that store lipid as TAG in the flesh (e.g. mackerel, herring, salmon, tuna, sardines). The oil
collected from fatty fish flesh or lean fish livers are termed ‘fish oil’ and it is rich in VLC n-3
PUFA EPA and DHA (8).

Terrestrial animals such as ruminants, pigs and poultry are also act as dietary sources. Adipose
tissues of poultry and pigs contain mainly saturated and mono unsaturated fatty acids (MUFA) if
they are given with low fat, cereal based diets as the fatty acids has to be synthesized from
carbohydrates. Inclusion of vegetable oils (soy bean oil) in the diet will increase the linoleic acid
in them (1).

In Ruminants 90% of the unsaturated fatty acids are hydrogenated by bacteria and other micro
organisms before they reach the adipose tissue and it contain less amount of PUFA than MUFA .
So inclusion of fat supplements such as safflower oil will help to produce more fat in them as
normal feed leads them to produce fat from carbohydrates.(1)

High amounts of medium and short chain fatty acids and small amounts of PUFA are available in
ruminant milk. Proportions of unsaturated to saturated fatty acids in cow’s milk change
according to the season. Milk collected in the winter season consists of more unsaturated milk
(2)
.Phospholipid in the eggs contain significant amount of PUFA (3).

Fish could be separated as lean fish (e.g. cod) and fatty fish (e.g. mackerel, herring), as they store
fats as triacylglycerols in the liver and in the flesh respectively. The fish oils are normally rich in
PUFA of n-3 category even though some types mainly have MUFA. Composition depends on
the season, diet and the variety of species (4).

Table 2.1 PUFA composition in some fish oils


Fatty Herring Menhaden Cod liver Trout liver
acid(g/100g total
fatty acids)

18:2 n-6 1 2 2 3
20:4 n-6 trace 2 1 1
20:5 n-3 3 14 6 16
22:6 n-3 3 10 27 7
(Adapted from Gunstone et al., 1986)

Table 2.2. Intakes of EPA and DHA and percentage contribution from food groups
by
dietary habit (groups contributing ‡ 5% to intake of either EPA or DHA)

EPA DHA
All Veg Meat Fish All Veg Meat Fish
n 7056 108 996 5952 7366 170 938 6258
Intake (g/d) 0.09 0.01 0.02 0.11 0.13 0.001 0.01 0.15
Dairy 2 20.5 10.7 1.7 0 0 0 0
Eggs 0.3 4.8 1.8 0.3 0.1 11.8 1 0.1
White fish 3.6 0 0 3.7 6.2 0 0 6.2
Fatty fish 59.6 0 0 61.1 63.2 0 0 64
Fish
Products&dishes 14.8 0 0 15.2 17.5 0 0 17.7
All fish 81.4 0 0 83.5 88.8 0 0 89.8
Meats 6.1 0 42.7 5.3 7.3 0 92.6 6.3
Spreading fats 6.4 50.7 36.8 5.6 0 0 0 0
Soups and sauces 0.8 16.4 2.4 0.7 1 88.2 6.3 0.9
Veg, vegetarians; meat, meat-eaters; fish, fish-
eaters.
Adapted from Welch AA et al.,(2001)

EPA and are essential n-3 PUFA and they are available basically in the fish based foods. The
table above shows, for vegetarians the main sources of EPA and DHA were spreading fats, dairy
and soups and sauces whereas for meat-eaters the main sources were meats and spreading fats.
As expected, for fish-eaters the fatty fish supplied the majority of dietary EPA and DHA.

Although total intake of EPA and DHA in the diet of vegetarians and meat-eaters was only 0.7–
18% of that of fish-eaters, non-fish sources are probably important in the diets of vegetarians and
meat-eaters(6).

There are large differences in fat intake among countries with average intakes among adults
varying from < 20 g/d in some developing countries to > 100g/d in some developed countries.
The mix of fatty acids consumed also varies in accordance with the fatty acid compositions of
the fats and oils used in food preparation and of the food stuff eaten. Average fat consumption
has changed over time and continues. In many developing countries fat intake is increasing,
while in developed countries fat intake has tended to decline (10).

Seed oils are the energy storage for many plants. Their fatty acid composition differs and mainly
consists of saturated and mono unsaturated fatty acids. Linoleic acid is available in maize
(50g/100g total fatty acids), sunflower oil (52 g/100g total fatty acids) and soybean (52 g/100g
total fatty acids) in relatively higher amount than other seed types (1).

Some more seeds such as oil of linseed contain 24.1% Linoleic acid and 47.4% Linolenic acid
as PUFA. Traditionally, linseed has been grown for its oil, which is used in the manufacture of
paints, varnishes and linoleum, because of its drying and hardening properties when exposed to
the air and sunlight. But the breeders have also produced linseed varieties that give oils with fatty
acid profiles for culinary uses. This is because these “linola” types, containing a high proportion
of linoleic acid and a low proportion of linolenic acid (5).

Other sources are the structural lipids present in the plant and animal cell membranes contain
phospholipids and glycolipids. It contains higher amount of PUFA than storage lipids in animals,
with the exception of fish oils. In muscle and offal fats have a higher proportion of arachidonic
acid (1). Plant leaves have linoleic, alpha linolenic, and arachidonic acid. Out of these alpha
linolenic is the most important and green vegetables are a good source of it (1).

Major roles of PUFA:


The major roles of lipids can be classified energy storage, energy providing, structural and
metabolic functions.

Fatty acids have many diverse functions in cells: their principal roles are as energy sources,
essential fatty acids can be converted in the body as non- essential fatty acids (11,45).

They have important structural roles in maintaining the fluidity, permeability and conformation
of membranes. For example, the myelin sheath of nerves and the rods of the retina have
specialized functions and highly specific lipid compositions (46).

In the membranes they play an important role in metabolic control via the inositol lipid cycle
which is involved in cell responses to a range of hormones, neurotransmitters and local growth
factors. The dominant species of phosphatidyl inositol (Ptdlns) in the plasma membrane contains
arachidonic acid as well as stearic acid (18:0) (47).

In membranes PUFA also play a critical role in metabolic control as precursors of the
eicosanoids( which are a complex group of highly biologically active, often short-lived
compounds with 20 carbon atoms produced by cells to act in their immediate environment),
particularly the prostanoids and the leukotrienes which are formed via the cyclo-oxygenase and
lipoxygenase pathways. The spectrum of eicosanoids produced can be influenced by the
unsaturated fatty acid composition of the diet (48).

In the early development of a child PUFA is vital. The supply of long chain PUFA, arachidonic
acid and DHA, to the fetus is crucial for normal development. Neural development, retinal
function, cognitive and learning ability and the vascular system could all be adversely affected if
the supply is inadequate (49, 50).

The most active period of cell division and organogenesis is in the first weeks of pregnancy (51). It
is important that the EFA intake during the preconception period satisfies the quantitative and
qualitative need for a fat store to guarantee energy and EFA provision in preparation for the early
part of pregnancy when appetite may be affected (52).

The premature and low birth weight infant has an increased risk of neuro-developmental
handicap (53). This may be due to a deficiency of long chain EFA whilst the infant is in utero(54).
The premature infant is specifically denied the high input of long chain EFA selectively provided
by the placenta during the fetal brain’s rapid period of growth in the last trimester of pregnancy.

In human milk, longer chain derivatives of linoleic and alpha linolenic acid (i.e. arachidonic acid
and DHA) account for about 1% of the total fatty acids. The provision of the equivalent amount
of linoleic acid and alpha linolenic acid in infant milk formulae is probably not an adequate
substitute. Infant milk formulae which provide the main nutrient intake of infants should supply
DHA, and possibly arachidonic acid, in the same concentration as human milk (52).

Health benefits:
Against coronary heart diseases (CHD):

Results are fairly contradictorily spread.

Fairly small intake of fish is protective against is protective against CHD death (12-14). For people
who had myocardial infarction, fish consumption has reduced the death rate butt surprisingly
more non- fatal heart attacks (15).

There is little evidence of an association between consumption of MUFA and CHD risk.
Partial replacement of saturated fatty acids by n-6 PUFA may reduce the risk of a CHD event,
but has not been shown to reduce risk from all causes.

Against plasma lipids:

Experimental studies have shown that when MUFA or PUFA replace C12-C16 saturated fatty
acids in the diet, they lead to a reduction of total and LDL cholesterol in the plasma (18). More
consistent effects are found with n-6 PUFA than with n-3 PUFA. Intakes of linoleic acid greater
than 12% of dietary energy also lead to a reduction in HDL cholesterol concentrations and are
therefore not advised (16-17).

Dietary intake of EPA and DHA lead to a marked reduction in plasma TAG and VLDL
cholesterol concentrations if they are consumed in amounts greater than 2-3g/day (18-19). HDL
cholesterol concentrations are increased but may be decreased by much higher intakes of n-3
PUFA (more than 10g/day) (16).

Against atherosclerosis also called “hardening of the arteries”:

A reduction in plasma total and LDL cholesterol concentrations and an increase in plasma HDL
cholesterol and apoprotein A1 lead to decreased atherosclerosis in animals and in human(20).
Experimental atherosclerosis is most strongly influenced by the saturated fatty acid content of
the diet. Substitution of saturated fatty acids by MUFA and n-6 PUFA will usually reduce
experimental atherosclerosis (21).

Dietary EPA and DHA inhibit the development of atherosclerosis in dogs, pigs and primates by
mechanisms independent of plasma cholesterol concentrations (22-24). It is not certain whether n-3
PUFA can inhibit atherosclerosis in man but fish oils may be of some benefit in preventing
restenosis following angioplasty (25).

Against thrombogenesis and fibrinolysis:

Changes in the dietary unsaturated fatty acids cause changes in the fatty acid composition of
phospholipids of platelet membranes and changes in the subsequent eicosanoid spectrum.

Dietary induced enrichment of platelet membranes with n-3 PUFA reduces the responsiveness ex
vivo of platelets to the aggregating agents such as collagen, ADP and thrombin (26). The shift in
thromboxane metabolism towards TXA3 formation at the expense of the more strongly pro-
thrombotic TXA2, formed from n-6 PUFA, might be one of the factors responsible for
thereduced tendency of platelets to aggregate(55). Large oral doses of n-3 PUFA also appear to
prolong the bleeding time and reduce platelet adhesiveness (27).
Against blood pressure:

Fish oils induce a small reduction in blood pressure provided they are given in daily doses
supplying about 3g or more of the n-3 PUFA. The reduction is more evident in those with mild
to moderate hypertension than in normotensive people (28).

The mechanism for the reduction in blood pressure is unknown. One possible mechanism may be
a restoration of the normal release of endothelium- derived relaxing factor (EDRF) in endothelial
cells which have been damaged by atherosclerosis or injured by exposure to high blood pressure
(29)
.

PUFA of the n-6 series do not have any demonstrable effect on blood pressure when consumed
in normal amounts (30).

Against cancer:

The evidences for human cancer are inconclusive and scanty. The evidence of animal models
suggests that n-3 PUFA inhibit but n-6 PUFA are a necessary extra pre-requisite for the
promotion and maintenance tumor growth (31-33).

Against diabetes:

Fatty acids of the n-6 series lower total and LDL cholesterol; fatty acids of the n-3 series have
less consistent effects (34, 35).

Unsaturated fatty acids of the n-6 series have no consistent effects on carbohydrate metabolism
in diabetes (34), but the long chain n-3 fatty acids tend to cause impaired glycaemic control in
non-insulin dependent diabetic subjects.

Preliminary data suggest a possible beneficial effect of dietary enrichment with unsaturated n-3
fatty acids on some microvascular complications of diabetes (36, 37).

Against skin diseases:

Human skin is functionally highly dependent on unsaturated fatty acids which not only
contribute to the integrity and barrier function of the skin (38) but also act as a source of mediators
that are important in inflammatory skin diseases. Sebum also contains essential fatty acids which
may play role in hair growth (39).

Supplementation with fish oil or with EPA causes a modest clinical benefit in psoriasis, probably
via effects on eicosanoid biosynthesis (40, 41)

Evening primrose seed oil, which contains GLA, produces a symptomatic improvement for
atopic eczema but does not change the underlying disease state (42).
Against immune disorders:

The immune system is extremely complex and it has many interactions with non- specific
inflammation. While many immunopathological mechanisms have been clarified, there is still
much uncertainty about their role in acute and chronic disorders of unknown aetiology. This is
also true of those situations in which immune mechanisms are clearly operating (43).

The increased consumption of n-3 fatty acids such as EPA and DHA favors the production of
prostaglandins of the 3 series and leukotrienes of the 5 series. The overall effect is to reduce the
efficiency of granulocyte mobilization (44).

Certain PUFA supplements have become popular for the treatment of rheumatoid arthritis,
multiple sclerosis, asthma and lupus. The proven clinical benefit of such measures is modest and
the long-term benefits and disadvantages need further evaluation. The observed changes in cell
membrane lipid composition and leukotriene spectrum may not necessarily account for any
clinical improvement (56-58).

Conclusion:

PUFA is available in some dietary sources and their levels vary depending on the food.
Consumption of these foods is not a sole source of n-3 or n-6 PUFA as these foods contain other
fatty acids too. Consuming these foods and direct consumption through capsules can produce
many beneficial effects basically against many diseases. For some diseases the maximum and
minimum intake levels has to be assessed.

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