Part 2

Bioactive
Compounds
in Functional Foods
1
Outline

• Lipids
• Essential Fatty acids / PUFA
• Conjugated linoleic acid
• Lecithin and Choline

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Lipids
• Lipids are organic compounds not soluble in
water but organic solvent
• They are the major macronutrient in human diet
and some are classified to have enhance human
health.
• Triacylglycerol (TAG) is the principle component
of dietary fats and oil. It is the major lipid in
human diet.

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Lipids
• Other lipids substances include:
• Phospholipid : a class of lipids that are a major
component of all cell membranes.
• Glycolipids: substances found in plant tissues that
have a sugar-derived unit replacing one of the fatty
acids.
• Sphingolipids: derivatives of sphingosine, which is
made from palmitic acid and the amino acid serine.
These compounds are important components of brain
tissue.
• Waxes 4
• Steroids (cholesterol and phytosterols).
TAG
• Chemically fats and oils are esters of fatty acids and glycerol.
• Three fatty acids esterified with three hydroxyl groups (OH)
groups of glycerol

+ 3 H2O

Glycerol Fatty acids Ester bond 5

Triacylglycerol
TAG
• Many of the fatty acids derive from TAG can be synthesis in
human body, but not all.
• The fatty acids that cannot synthesis by human body are
known as essential fatty acids (EFAs).
• EFAs are Polyunsaturated fatty acids (PUFA) that have >1
double bond within first seven carbon atoms of the
hydrocarbon chain, counting from the methyl end.
• Due to the inability of human body to insert double bonds
between the first few carbon atoms, human is unable to
synthesis EFAs.

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Fatty acids
Fatty acids are carboxylic acids with hydrocarbon chains of 4-36 carbons
Name Carbon Unsaturation Common
number symbol
Short chain Butyric acid 4 0 C 4:0
FA (4-10
carbons) Capric acid 10 0 C 10:0

Medium Lauric acid 12 0 C 12:0

chain FA (12- Saturated
14 carbons) Myristic acid 14 0 C 14:0 fatty acids

Long chain Palmitic acid 16 0 C 16:0

FA (>14
carbons) Stearic acid 18 0 C 18:0

Oleic acid 18 1 C 18:1

Linoleic acid 18 2 C 18:2 Unsaturated

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fatty acids
Linolenic acid 18 3 C 18:3
EFAs
• EFAs are divided into two major groups:
• Omega-3 (ω3 or n-3) fatty acids
• food source include fatty fish, marine oil
• Omega-6 (ω6 or n-6) fatty acids
• Food source include plant oils (sunflower oil, corn oil, safflower oil)

* The notation ω and n are commonly use interchangable.

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Nomenclature of EFAs
• α-linolenic acid (18:3, ω3) has 18 carbons
and three double bonds in the structure,
with the first double bond located
between C3 and C4 (calculated from the
methyl end).
• Linoleic acid (18:2, ω6) has 18 carbons
and two doubles bonds in the structure,
with the first double bond located
between C6 and C7

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 Metabolic
pathway of
n-3 and n-6.

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Β-oxidation

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Metabolism of n-3 and n-6.
• Linoleic acids (18:2, n-6) is the parent compound for the n-6
series; and α-linolenic acid (18:3, n-3) is the parent compound
of the n-3 series.
• Human body is able to synthesis the other five members of
each series from their parent compounds.
• However, mammals has no ability to convert from n-3 to n-6,
vice verses.
• A dietary supply of any member of the series will enable the
body to synthesis the subsequent fatty acids of the series.

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Metabolism of n-3 and n-6 (cont)

• ∆-6 desaturase, is the first enzyme on the

pathway. It is the slowest of all five in its
metabolism rate, and thus rate-limiting.
• The enzyme activity of ∆-6 desaturase is
inhibited by high concentration of end product
(end product inhibition).
• Because ∆-6 desaturase is a common enzyme on
both n-3 and n-6 pathway, the high level of
either parent compound could suppress the
metabolism of the other one. Therefore the
ratio of n-6 to n-3 is very important. 14
Metabolism of n-3 and n-6 (cont)

• The idea ratio of n-6:n-3 is at 4-5 : 1.

• Modern diet is high in n-6, but lack of n-3.
The ratio was over 10:1, and perhaps
exceeding 30 in some instances.
• High intake of n-6 will limit the metabolism of
n-3 into DHA and EPA, despite the availability
of n-3.

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Functions of EFA
• n-3, EPA and DHA, are important for brain, visual and
neurological development.
• DHA is the final product in the metabolism of n-3 EFA in
human body. It is also readily available in food such as fish
(fish liver oil and fish body oil) and marine algae.
• DHA is the major component of grey matter in the in the
brain. It is important for the development of brain, retina and
eye functions.

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EFA and eicosanoids
production
• Eicosanoids are short-duration regulatory molecules that exert
their effects very close to their site of production and then
rapidly inactivated.
• They are sometimes call locally acting hormones that regulate
cells that produce them.
• There are three categories of eicosanoids:
• Thromboxanes
• Leukotriences
• Prostaglandins
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EFA and eicosanoids production
(cont)

• Eicosanoids regulate secretory processes, inflammatory and

immune responses, reproduction function, cardiovascular and
respiratory functions.
• Arachidonic acid is the precursor for potent eicosanoids; while
dihomo-γ-linolenic and eicosapentaenoic acid (EPA) produce less
potent eicosanoids.

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Deficiency of n-3 and n-6
• Overt symptom of deficiency is rare. This is because
• The requirement to prevent overt deficiency is very small.
• A healthy adult has substantial stores of EFA in body fat
• It is difficult to entirely omitted EFA from the diet. The EFA are
found in a variety of food.
• Overt deficiency symptoms can be observed in Total parenteral
nutrition (TPN) patients with no EFA in their feeding.
• During the deficiency of n-3 and n-6, the body replace them
with n-9 fatty acids (oleic acid), which is not an EFA.

TPN: a method of feeding that bypasses the gastrointestinal tract. Fluids are
given into a vein to provide most of the nutrients the body needs. The method is
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used when a person cannot or should not receive feedings or fluids by mouth.
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 Conjugated Linoleic Acid (CLA)
• CLA is a collective term used to describe the mixture of positional and
geometric isomers of linoleic acid with conjugated double bonds.
• Isomers are substances that have the same chemical formula, but different
in 3-dimensional arrangement of atoms.
• The two bioactive CLA are
• Cis-9, trans-11 CLA
• Trans-10, cis-12 CLA

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CLA production
• The CLA are produced in the ruminant (cattle and sheep)
stomach by the bacteria that able to isomerized the dietary
linoleic acid. Human lumen does not has this ability.
• Meat and dairy products from the ruminant animals are good
source of CLA.
• CLA content in meat and dairy vary, depending on the diet of
the animal. Animal gaze on pasture have more CLA than the
grain/commercial fed animals.
• CLA is not an essential nutrient. The use of CLA nutraceuticals
is debatable.

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CLA supplementation
• CLA is a natural component in human diet and has been in
human food for centuries.
• The pharmacology dose of CLA is at 250 mg/day.
• However it is hardly achievable in normal diet. High intake of
dairy and meat for CLA in not recommended due to their high
saturated fat content.
• The use of high dosage of CLA over a relatively short period of
time does not cause serious effects; however the chronic
effect of CLA supplementation is unknown.

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Potential health benefits of CLA
• Anti-mutagenic in bacteria.
• Reduce the chemical induction of tumors at various site in rats
and mice.
• Reduce plasma cholesterol and plasma TAG concentration in
rabbits.
• Modulate the inflammation response in animal
• Reduce body fat content and increase lean body mass in animal.

*Most studies focuses on animals at large dosage of CLA. There is

lack of concrete evidence on the use of CLA for human health
benefits.
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Lecithin and choline
• Lecithin is commonly extracted from soybean oil or egg yolk.
• Lecithin is a permitted food additive used for its emulsifying
properties (eg. Milk powder, margarine, low-fat spread).
• Lecithin is a mixture of phospholipids containing
• Phosphatidyl choline (PC) ( major phospholipids)
• Phosphatidyl inositol (PI)
• Phosphatidyl ethanolamine (PE)
• Phosphatidyl serine (PS)
• Some scientist used the terms Lecithin and PC
interchangeably.
• Choline is the component found in PC. Choline is present in
many foods (eg. nuts, eggs, liver, meat, cauliflower lettuce). 25
 Phosphatidyl choline (PC)
Glycerol backbone
2 fatty acids

Generally a PC contain a choline head group, with glycerophosphoric

acid and two fatty acids of any type.
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Functions of lecithin and
choline
• The major function of choline supplement include:
• A component of acetylcholine (nerve transmitter)
• A component of cell membranes and plasma
lipoproteins (for fat transportation in human body)
• Act as methyl donor
• Choline is not an essential nutrient. It can be synthesized
endogenously.
• Human choline deficiency is rare.

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Deficiency of lecithin and choline
• Study on non-ruminant animal induced choline deficiency
shows adverse consequences in the kidney, liver, pancreas.
The animals also show growth and memory disorder.
• Humans fed with choline deficient diet for 3 weeks developed
biochemical indication of choline deficiency.
• Patients on total parenteral nutrition reported fatty infiltration
of the liver and liver damage due to choline deficiency.

• Fatty infiltration of the liver is a condition of abnormal

deposition of fat in the liver.

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Inconclusive Research Findings
in lecithin and choline
• Alzheimer's disease has low activity of enzymes
that synthesizes acetylcholine.
• Lecithin and choline maybe beneficial to
dementia and Alzheimer’s disease treatment.
• However some studies found no evidence of
any beneficial effect of lecithin in Alzheimer's or
disease or other form of dementia.

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Inconclusive Research Findings
in lecithin and choline
• Large doses of lecithin may lower serum cholesterol, but
in properly controlled trial PC did not have independent
effects on serum cholesterol.
• Previous study which found significant effect of lecithin
on serum cholesterol was deem to reported faults in the
analysis, or the presence of PUFA in the preparation of
lecithin.
• At this point, the evidence for any beneficial effects from
lecithin and choline supplements is very weak or non-
existent (G.P Webb, 2011).
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