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NAHEP Component-2 Project “Investments In ICAR Leadership In Agricultural Higher Education”

Division of Computer Applications
ICAR-Indian Agricultural Statistics Research Institute
 Course Details

Course Name Nutraceuticals and Functional Foods

Lesson 2 Antioxidants: Types, Chemical Makeup And

Mechanism Of Action Against Free Radicals

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judgement. Statement of fact and opinions expressed are those of the presenter individually and are not the opinion or
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1
Created by

Name Role University

Lala Lajpat Rai University of

SHALINI ARORA Content Creator
Veterinary and Animal Sciences, Hisar

ATANU JANA Course Reviewer Anand Agricultural University, Anand

2
 Introduction

• Antioxidants are the substances that, when present in the

food inhibit, and prevent oxidation (of lipid) and quality
deterioration of food.

• It lowers the risk related to the occurrence of

degenerative diseases that may arise due to oxidative
stress.
 Introduction
• Several antioxidants are present naturally in the plants and
animals viz.,
– lecithin in egg
– isoflavones in soybean
– Catechins in green tea
– Butyrophilin in buttermilk
– Vitamin C & E in fruit, vegetable oils
– Enzymes like catalase (CAT), superoxide dismutase(SOD),
and various peroxidases

• Use of antioxidants prevents cellular damage (i.e. unwanted

inflammatory responses) caused by the presence of free
radicals.
 List of oxidants and free radicals
Oxidants Free radicals
Hydrogen peroxide (H2O2) Hydroxyl (OH•)

Ozone (O3) Superoxide (O2•ˉ)

Singlet oxygen (1O2) Nitric oxide (NO•)
Hypochlorous acid (HOCl) Nitrogen dioxide (NO2•)

Nitrous acid (HNO2 ) Peroxyl (ROO•)

Peroxynitrite (ONOOˉ) Lipid peroxyl (LOO•)
Dinitrogen trioxide (N2O3)

Lipid peroxide (LOOH)

 Nutrient possessing antioxidative
activity present in foods
Food Antioxidative
nutrient
Acorn squash, Apricots, cantaloupe, peaches Beta carotene
pumpkin, winter squash, Bell peppers, Sweet
potatoes, Broccoli, greens, spinach, carrots
Citrus fruits, Berries, Grapefruit, Mango, papaya, Vitamin C
watermelon, Sweet potatoes, Bell peppers, Broccoli,
greens, spinach, Tomatoes (canned)
Apples, Beans, Tea - black or green Catechins
Wheat germ, whole grains, nuts, nut butter, oils, Vitamin E
seeds
Beets, Berries Anthocyanins
Berries Catechins
Type of antioxidant present in foods
Food Antioxidant
Broccoli, greens, spinach, Corn, Egg Lutein
(especially in yolks)
Egg plant Anthocyanins
Grapefruit, pink Tomatoes (canned) Lycopene
Watermelon
Grapes, red wine Anthocyanins (red and
purple grapes),
Resveratrol
Milk, Egg Vitamin A
Oatmeal, Wheat germ, whole grains, Selenium
salmon, tuna, seafood, Garlic and onions
Brown rice, Chicken, Egg
 Antioxidant categories
• Antioxidants are categorized as endogenous and exogenous.
• The human biological systems themselves develop the
antioxidant enzymes and molecules viz., ‘endogenous
antioxidants’; the ‘exogenous antioxidants’ are derived from the
diet.
Endogenous antioxidants Exogenous antioxidant
GSH peroxidase (GPX) Vitamin C
Catalase (CAT) Tocopherols
Superoxide dismutase (SOD) Flavonoids
GSH Carotenoids
Albumin Lipoic acid and Selenium
Types of Action performed Actual compounds
antioxidants
Primary Terminates free radical Tocopherols, tertiary
antioxidants chain reaction amines, flavonoids,
phenolic compounds
Oxygen React with oxygen and Ascorbic acid and its
scavengers eliminates it derivatives
Secondary Breaks down lipid Sulphur compounds,
antioxidants peroxides into stable Seleno-compounds
products
Enzymic Removes highly Catalase, Glutathione
antioxidants oxidative species peroxidase, Superoxide
dismutase
Chelating agents Chelates metallic ions Phytic acid, citric acid
such as copper and
iron
 Types of Antioxidants

• The primary antioxidant functions either by neutralizing

the free radicals or donating the hydrogen atoms by a
single electron transfer (ET) mechanism.

• Antioxidants can be classified into two major types based

on their source, i.e.,
(a) Natural
(b) Synthetic
 Classification of antioxidant based on source
Source Type Example
Enzymatic- Superoxide dismutase
Natural Primary Catalase
Glutathione peroxidase
Secondary Glutathione reductase
Non-enzymatic Minerals - Se, Cu, Mn, Zn
Vitamins-A, C, E
Carotenoids- β-carotene, lycopene, lutein, zeaxanthin
Polyphenols – flavonoids, polyphenols, curcumin,
gingerol
Protein (hydrolysed casein) and non-protein
antioxidants
Synthetic Butylated Hydroxy Anisole (BHA), Butylated
Hydroxy Toluene (BHT), Propyl Gallate (PG) and
Tertiary-Butyl Hydroquinone (TBHQ).
Chemical structures of natural
antioxidants

Vitamin A Vitamin E

Vitamin C
Chemical structures of synthetic
antioxidants
Mechanism of action of antioxidant
Initiation
• R:H + O::O + Initiator → R• + HOO•
• R• + O::O → ROO•
• ROO• + R:H → ROOH + R•

Propagation
R- Alkyl radical
• RO:OH → RO• + HO•
H- Hydrogen
• R::R + •OH → R:R-O•
• R• + R• → R:R OH- hydroxyl radical
• R• + ROO• → ROOR RO-Alkoxyl radical
• ROO• + ROO• → ROOR + O2 ROO- Peroxyl Radical
• ROO• + AH → ROOH + A• ROOH-Organic
• RO8 + AH → ROH + A • (Brewer, 2011) peroxide, etc.
Termination
• ROO• + A• → ROOA.
• RO • + A • → ROA
• RO • + RH → ROOH + R •
 Preventive measures to curb
oxidative reactions
• The rate at which the initiated chain reaction is prevented or
reduced by the application of antioxidant.
– BHA has a maximum permissible concentration of 25
mg/kg in dried potatoes and 1000 mg/kg in essential oils;
– PG can be used in fried food, canned food, and other
applications; the maximum allowed concentration is 100
mg/kg (of total fat) (European Food Safety Authority, 2011)
• Antioxidant further stabilizes the oxidation caused by
transition metal ions such as copper and iron, thus preventing
oxidation
 Mechanism of action to inhibit
oxidative reaction
• If the initiation step in the formation of free radicals is stopped
by antioxidant, the chain propagation step stop. If the chemical
compound disturbs the free radical chain's propagation step,
such compound can delay the start or slow down the rate of
lipid oxidation.
• The metal chelating agents, singlet oxygen inhibitors and
peroxide stabilizers can be used to delay the initiation of free
radical formation.
• The donation of hydrogen from the antioxidants and the metal
chelating agents can minimize the propagation of free radical
chain reaction.
 Biochemical functions of
antioxidants

• -carotene is used to prevent skin disease and it is useful during

loss of vision.
• Ascorbic acid (Vitamin C) combat free radicals and prevent skin
ageing. Consumption of vitamin C in diet (RDA of 90 mg/day for
adult men; 75 mg/day for adult women) stops the formation of
skin sagging, skin spots, wrinkles.
• Ascorbic acid also protects lungs, central nervous system from
free radical damage and DNA from the attack of free radicals .
Biochemical functions of antioxidants
• Vitamin E prevents or delays the chronic diseases including
Alzheimer’s, osteoarthritis, related with the free radicals .
• The anti-inflammatory agent α-tocopherol protects the skin
damage caused by sun rays.
• Glutathione helps in detoxifying the body from heavy metals,
solvents, pesticides, etc.
• Lycopene removes harmful carcinogens from the body thus
controlling cancers.
• Flavonoids play a wide variety of roles in protecting human
health.This is attributed to their anti-oxidative, anti-
inflammatory and anti-carcinogenic properties.
 Glossary

• Oxidation: It is a chemical reaction wherein the electrons are transferred from

one molecule, atom or ion to the oxidizing agents

• Free radicals: These are reactive chemical species wherein the atom’s
outermost shell contains one or more unpaired electrons that are highly
reactive and starts the chain reactions
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