Physiological Function of Vitamins and their chemistry vitamin A and b complex, vitamin C, E, and cyanocobalamin

1. VITAMINS
Presented By:-
Subham Kumar Vishwakarma
M.Pharma-I
Pharmaceutical Chemistry
SUBJECT- CHEMISTRY OF NATURAL PRODUCT

2. Vitamin
Any of a group of organic
compounds which are essential
for normal growth and
nutrition and are required in
small quantities in the diet
because they cannot be
synthesized by the body.
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3. Physiological Function of
Vitamins
 They build up the resistance of the body against diseases.
 Prevent and cure various diseases caused by deficiency.
 Help the digestion and utilization of mineral salts and
Carbohydrates in the body.
 Stimulate and give strength to digestive and nervous
system.
 Help health protection.
 Help maintenance of proper health and normal growth.

4. Chemistry and physiological
significance of vitamins
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5. Vitamin A(Retinol)
 Vitamin A, a fat soluble vitamin.
 Vitamin involved in immune function, vision,
reproduction.
 Vitamin A & Cboth are important for the immune system.
 Vitamin A is a pale yellow primary alcohol derived from
carotene. It include Retinol (alcoholic form)- One of the
most active usable form , Retinal (aldehyde form) and
Retinoic acid ( acidic form)
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6.  Vision-
1. Generates pigments for the retina
2. Maintains surface lining of eyes
 Bone growth
 Reproduction
 Cell division and differentiation
 Healthy Skin
 Regulate Immune System
 Found in animal and plant sources
 Animal Sources –
 Eggs
 Meat
 Cheese
 Milk
 Liver
 Kidney
 Cod
 Halibut fish oil
Plant Sources –
1. Carrots
2. Sweet Potatoes
3. Pink Grapefruit
4. Apricots
5. Broccoli
6. Spinach
7. Pumpkin

7. Chemistry of vitaminA
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 Vitamin A (Retinol) is a cyclic polyenealcohol which
resembles the structure of Diterpenoid.
 The structre of vitamin A constitute of a β-ionone ring.
 Vitamin A consist 2 isoprene unit (C10H16)
 four conjugated double bonds in the side chain of vitaminA.
 They are in trans arrangement.
 Synthetic retinol is a trans isomer.
 β- ionone ring and conjugated double bonds are essential for
the biological activity of vitaminA.

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9. β–Carotene (Provitamin-A)
• Precursor of vit-A is β–carotene
• Beta carotene has 1/6th activity of Vitamin

10. Physiological significance of
vitaminA
 Vitamin A is best known of its role in the
physiological functions of vision.
 Vitamin A participates in numerous other physiological
functions, it ensures the normal proliferation of epithelial
cells, the development of teeth and bones.
 Vitamin A deficiency(VAD) is a lack of vitaminA in
blood and tissues.
 Vitamin A deficiency its early stages causesthe so-
called night blindness, a vision problem at twilight or
in poor light.
 Vitamin A is essential for producingrhodopsin, the
photosensitive substance of the retina.
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11.  The deficiency of vitamin A can cause further more dry eye,
ataxia, conjunctivitis, corneal ulcers, skin lesions, disorders of
the epithelia (bronchi, respiratory tracts, salivary glands), bone
formation and nervous system abnormalities, and increased
susceptibility to diseases.
 Vitamin A in overdose can lead to bone disorders,
gingivitis, and finally the loss of vision.
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Rhodopsin
Trans-Retinal Trans-Retinol
Dehydrogenase
(Activation of Rod/Cones)
[Retinal + opsin(protein)]
inactive
Cis-Retinal Cis-Retinol
Dehydrogenase
isomerase
Eyes In Liver

12. Vitamin B1 (Thiamin)
 Thiamine is one member of water-
soluble Vitamin B-complex and is
in the thermolabile fraction.
 Vitamin B1, thiamin, or thiamine
enables the body to use
carbohydrates as energy.
 It is essential for glucose
metabolism, and it plays a key
role in nerve, muscle, and heart
function(antineuritic).
 Vitamin B1 is a water- soluble
vitamin, as are all vitamins of the
B complex.
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13. Chemistry of Vitamin B1
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14.  Thiamine or vitamin B1 named as the "thio-vitamine"
("sulfur-containing vitamin") is a water-soluble of the B
complex.
 It is water soluble vitamin.
 It is anti beriberi vitamin.
 It has specific coenzyme Thiamine pyrophosphate (TPP)
which is mostly associated with carbohydrates
metabolism.
 Thiamine contain pyrimidine ring Thiazole ring held by
methylene bridge.
 Thiamine is only natural compound which having
thiazole ring.
 Alcohol group of thiamine esterified with phosphate
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15. Physiological significance of
vitamin B1
 The active from of vitamin B1 in the body is thiamin
pyrophosphate (TPP) which along with lipoic acid acts as a
prosthetic group for carboxylases.
 Thiamine pyrophosphate is formed by the esterification of
alcoholic group of thiamine with phosphate.
 TPP transferase catalyzes the transfer of pyrophosphate group
from ATPtothiamine.
 Citric acid cycle and synthesis of acetylcholine thus affecting the
neurotransmitter transmission.
 Transketolation reaction and decarboxylation of α-ketoglutaric
acid to succinic acid.
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16. 13 (TPP)

17. +
+ CO
2
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18. Vitamin B2 (Riboflavin)
 Riboflavin is a Vitamin B.
 It can be found in certain foods such
as milk, meat, eggs, nuts, enriched
flour, and green vegetables.
 Riboflavin is necessary for growth
and for the production of red
blood cells.
 Riboflavin also plays an important
role in how our bodies gets energy
from carbohydrates, fats, and
proteins.
 Vitamin B2 is closely related to the
yellow water-soluble pigments
known as Flavines (isoalloxazines),
and since it was first isolated from
milk, Vitamin B2 is also known as
Lactoflavin.
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19. Chemistry of vitamin B2
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20.  The structure of riboflavin consists of 6,7- dimethyl- isoalloxazine
( heterocyclic three ring system – benzene and pteridine ring ) to
which a sugar alcohol called ribitoyal group is attached at 9th
position.
 It is water soluble vitamin.
 It aids in the metabolism your fats, carbohydrates, protein and
ketone bodies.
 It is also important for energy metabolism (ATP
production in mitochondria )
 Flavin mononucleotide (FMN) and Flavin adenine
dinucleotide (FAD)
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21. physiological significance of vitamin
B2
 Riboflavin is the component of two flavin enzymes
The flavin mononucleotide (FMN)
The flavin adenine dinucleotide (FAD)
 Both these flavin enzymes take part in various oxidation-reduction
reactions.
 The oxidized flavines are yellow in colour while upon reduction (
one hydrogen atom at 1 and other at 10 positions acquisition
occurs) and they become colourless.
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22. The reaction can also proceed in the reverse
direction.
Hydrogen addition
occurs in 2 steps
-
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25.  Both the coenzymes function with a group of proteins
known as the flavoproteins.
 These flavoproteins due to their diverse nature can act as
oxidases, dehydrogenases, hydroxylases ,oxidative
decorboxylases.
 Riboflavin or vitamin B2 is an essential nutrient in human
nutrition and plays a key role in the production of energy.
 Vitamin B2 is needed to process amino acids and fats, activate
and folic acid, and help convert carbohydrates into the fuel the
body runs on.
 Vitamin B2 is an intermediary the transfer of electrons in the
cellular oxidation-reduction reactions which generate energy from
protein, carbohydrate and fat.
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26. Vitamin B12 / Cyanocobalamin
 Vitamin B12 does a lot of things for
your body.
 It helps make your DNA and your red
blood cells.
 B12 is the most chemically complex of
all the vitamins
 Vitamin B12 is the only naturally
occurring organic compound which
contains cobalt (35%).
 It is water soluble, deep red, tasteless,
crystalline compound.
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27. Chemistry of vitamin B12
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28.  There are many closely related compounds having B12 activity.
All are cobalamins and contain in their molecules a portion called
corrin ring which to a large extent resembles the tetrapyrrole ring
structure of porphyrins.
 A single cobalt atom having one positive charge is present in the
center of this ring. The Co atom is attached to all the four N atoms
of corrin ring in the same way as Fe++ is attached to 5,6,
dimethylbenzimidazole ribose which is attached to the side chain
on ring IV through Phosphate and aminopropanol.
 The positive charge on Co atom is balanced by one of the several
groups which give rise to more than one type of vitamin B12.
These different types of vitamin B12 are given below along with
their characteristic groups attached to the Co atom
 B12 : Cyanocobalamin: It has CN. It is the commonly used form of
the vitamin B12
 B12 -a : hydroxocobalamin: It has OH. It is claimed to be retained
in the body
 B12 -b : aquocobalamin: It has H2O
 B12 -c: nitrocobalamin: It has NO2
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29. 1. Supports Energy
Vitamin B12 plays a key role in how your bod creates energy. It
keeps your cells fed, happy, and healthy. Without it, your cells get
hungry and you feel weak, tired, and like you’re dragging all the
time. The nutrient releases energy into the cell and provides you
with the appropriate balance you need for thinking and moving
throughout your day.
2. Protects the Heart
Your heart and entire cardiovascular system needs B12. One of its
jobs is to remove a dangerous protein called homocysteine from the
blood. If homocysteine is allowed to roam through blood, it
damages your arteries leading
to inflammation and heart disease. Get enough B12 and you’ll
keep homocysteine levels down and your heart happy.
Physiological significance of vitamin
B12

30. 3. Your Bones Need It
Studies have found patients with osteoporosis have higher levels
of homocysteine and low levels of B12 than people with strong,
healthy bones.Could B12 be a viable adjunct to future
osteoporosis approache. If you suffer from osteoporosis or similar
bone issues, speak to your doctor about getting your vitamin B12
levels tested.
4. Prevents Nerve Damage
Your nerves have a protective covering to keep them safe from
toxins and free radicals in your blood.
Without these coverings, called myelin sheaths, exposed nerves
get damaged and may even die. These dead nerves disrupt
signals to and from the brain and may play a role in nerve-
related conditions. Vitamin B12 supports the way your body
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31. Vitamin C
 Vitamin C is a water
soluble vitamin.
 The use of vitamin C
in megadoses to cure
everything from
common cold to
cancer.
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32. Chemistry of vitamin C
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33. Chemistry of vitamin C
 It is water soluble and is easily destroyed by heat, alkali and
storage.
 In the process of cooking, 70% of vitamin Cis lost.
 The structural formula of ascorbic acid closely resembles that of
carbohydrates.
 It has strong reducing property.
 It’s a heterocyclic furan-2-one detivative.
 Ascorbic acid is a hexose derivative and closely
resembles monosaccharide’s in structure.
 vitamin C exists in two forms
L-ascorbic acid (reduces form)
L- Dehydro ascorbic acid (oxidized form)
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34. oxidizedform reduces form
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35.  Ascorbic acid performs numerous physiological functions in
the human body:
 the synthesis of collagen, and neuro-transmitters
 the synthesis and catabolism of tyrosine
 the metabolism of microsome.
 Ascorbic acid is well known for its antioxidant activity,
acting as a reducing agent to reverse oxidation in liquids.
 Vitamin C is a natural antihistamine. It both prevents
histamine release and increases the detoxification of
histamine.
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Physiological significance of vitamin C

36. The synthesis and catabolism of tyrosine
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38. Vitamin E
 Vitamin E is a
vitamin
that dissolves in fat.
 It is found in many
foods including
vegetable oils, meat,
poultry, eggs, fruits,
vegetables, and wheat
germ oil.
 It is also available as
a supplement.
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39. Chemistry of vitamin E
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40.  Vitamin E is the name given to a group of tocopherols and
tocotrienols.
 About four tocopherols (vitmin E vitamers) have been identified alpha,
beta, gama, delta.
 Alpha- tochopherols is the most active.
 The tochopherols are the derivatives of 6- hydroxy chromane (tocol)
ring with isoprenoid (3units) side chain.
 The antioxidant property is due to chromane ring.
 There are four main forms of tocopherols.
 They are
 α-tocopherol : 5,7,8 trimethyl tocol
 β-tocopherol : 5,8 dimethyl tocol
 γ -tocopherol :7,8 dimethyl tocol
 δ-tocopherol : 8 methyl tocopherol
 α-tocopherol is most active and predominant form of vitamin E .
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 Tocotrienols : There are four related vitamin E
compounds called α, β, γ and δ tocotrienols.

43. Physiological significance of
vitamin E
 Vitamin E plays an important role as an antioxidant and
protect the body cells from the damage caused by free
radicals.
 These free radicals are highly reactive and distructive
compounds formed as a result of oxidative deteriorational
(metabolism) of polyunsaturated fats.
 Factors contributing for free radical genaration in the body
include smoking and exposure to Uv-radiations.
 Tocopherols (Vitamin E) are equipped to perform a unique
function. They can interrupt free radical chain reactions by
capturing the free radical; this imparts to them their antioxidant
properties.
 The free hydroxyl group on the aromatic ring is responsible for the
antioxidant properties. The hydrogen from this group is donated to
the free radical, resulting in a relatively stable free radical form of
the vitamin.
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45. Vitamin B9 (Folic acid)
 A synthetic form of folic acid is used in
dietary supplements.
 Folic acid the acts by helping body
produce and maintain new cells.
 In particular, red blood cell formation is
dependent upon adequate levels of this
vitamin.
 Folic acid deficiency is a known cause of
anemia in both adults and children.
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46. Chemistry of B9
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47.  The word folic acid is derived from latin word
Folium means leaf & it is also isolated from the
leafy vegetable spinach.
 Folic acid mainly consists of three
components
 Pteridine ring
 PABA (p-amino benzoic acid) )
 Glutamic acid residue (1 to 7 residues)
 Hence it is known as Pteroyl-glutamic acid
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48. Physiological significance of B9
 Folic acid in the form of tetrahydrofolic acid is
biologically active as a co-enzyme, with the
following metabolic functions:
1. Transfer of specific C1 units (methyl and formyl
groups), which are important for cell growth, cell
division and cell differentiation in the metabolism of
proteins and of DNA and RNA.
2. Together with vitamin B12, it converts
homocysteine into methionine.
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51. Vitamin B3 (Niacin)
 Having enough
niacin, or vitamin
B3, in the body is
important for
general good
health.
 As a treatment,
higher amounts
of niacin can
improve cholesterol
levels and lower
cardiovascular risks.
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52. Chemistry of B3
 The coenzymes of Niacin (NAD+ & NADP+)
can be synthesized by the essential amino acid
tryptophan.
 The term "Niacin" is used for Nicotinic acid.
 The amide form of Niacin is known as
niacinamide or nicotinamide.
 The conversion of Niacin to niacinamide takes
place in the kidney, brain slices and liver slices.
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54. Physiological significance of B3
 Vitamin B3 (niacin) is important for the body
because it helps to: Convert food into glucose,
used to produce energy. Produce
macromolecules, including fatty acids and
cholesterol.
 Niacin is a B vitamin that helps activate over
200 enzymes, the majority of which regulate the
breakdown of carbohydrates, fats and proteins,
which the body then uses for energy and for
keeping the nervous system, digestive system,
skin, hair and eyes healthy.
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