Chemistry of natural product

1. VITAMINS
Name: Zofina I. Patel
M-pharm Sem-1
Subject: Chemistry in natural
products
Guided under: Mr. STEPHEN
AVARVU

2. Definition of 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. Chemistry and
physiological significance
of vitamins
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4. Vitamin A (Retinol)
 Vitamin A, a fat
soluble vitamin.
 Vitamin involved in
immune function,
vision,
reproduction.
 Vitamin A & C both
are important for
the immune
system.
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5. Chemistry of vitamin A
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6.  Vitamin A (Retinol) is a cyclic polyene alcohol
which resembles the structure of Diterpenoid.
 The structre of vitamin A constiture of a β- ionone
ring.
 four conjugated double bonds in the side chain of
vitamin A.
 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 vitamin A.
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7. Physiological significance of
vitamin A
 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 vitamin A
in blood and tissues.
 Vitamin A deficiency its early stages causes the
so-called night blindness, a vision problem at
twilight or in poor light.
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8.  Vitamin A is essential for producing rhodopsin,
the photosensitive substance of the retina.
 The deficiency of vitamin A can cause
furthermore 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
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9. Vitamin B1 (Thiamin)
 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.
 Vitamin B1 is a water-
soluble vitamin, as are
all vitamins of the B
complex.
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10. Chemistry of vitamin B1
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11.  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.
 In 1936 williams and his associates determines the
structure of Thiamine.
 Thiamine contain pyrimidine ring Thiazole ring held by
methylene bridge.
 Thiamine is onlynatural compound which having
thiazole ring.
 Alcohol group of thiamine esterified with phosphate
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12. 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 ATP to thiamine.
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14.  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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15. +
+ CO2
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16. Vitamin B2 (Riboflavin)
 Riboflavin is a B vitamin.
 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.
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17. Chemistry of vitamin B2
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18.  The structure of riboflavin consists of 6,7-
dimethyl- isoalloxazine ( heterocyclic three ring
system ) 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 your energy
metabolism
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19. Physiological significance of
vitamin B2
 Riboflavin is the component of two flavin
enzymes
 The flavin mononucleotide (FMN)
 The flavin adenine dinucleotide
 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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20. The reaction can also proceed in the reverse
direction.
Hydrogen addition
occurs in 2 steps
-
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23.  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.
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24.  Under some conditions, vitamin B2 can act as
an antioxidant.
 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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25. Vitamin B12
 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
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26. Chemistry of vitamin B12
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27.  Vitamin B12 is the only naturally occurring
organic compound which contains cobalt
(35%).
 It is water soluble, deep red, tasteless,
crystalline compound with a molecular weight
of 1355 and is hence stable at neutral pH but
not at alkaline pH.
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28.  The salient features of the structure of Vitamin B12 are given
below:
1. 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.
2. 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.
3. 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
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29.  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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30. Physiological significance of
vitamin B12
 1. Supports Energy
Vitamin B12 plays a key role in how your body 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.
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31.  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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32.  5. Protects Brain Health
Researchers have noted Alzheimer’s patients have much
lower levels of B12 than those of a similar age who have
sharp, clear memory. In the same way B12 helps protect
nerve cells, it helps protect the myelin sheaths of brain cells
that are often lacking in Alzheimer’s patients. Some research
suggests that cobalamin deficiency may cause a type of
dementia in elderly patients that is in fact reversible with the
right nutritional intervention.
 6. Keeps You Looking and Feeling Young
Aging happens when your cells begin to wear and tear, and
they age faster when your DNA doesn’t replicate correctly.
Many factors can affect DNA replication, like free radicals,
toxins in the blood, high blood sugar, and high levels of
omega-6 fats in your diet. B12 supports DNA health, thereby
keeping your cells younger. And when your cells are young,
you look and feel young too.
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33. 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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34. Chemistry of vitamin C
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35. 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 C is
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.
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36.  vitamin C exists in two forms
 L-ascorbic acid (reduces form)
 L-Dehydro ascorbic acid (oxidized form)
 oxidized form reduces form
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38. Physiological significance of
vitamin C
 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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39. The synthesis and catabolism of tyrosine
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41. 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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42. Chemistry of vitamin E
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44.  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.
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45.  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.

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49. 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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51. Vitamin B9 (Folic acid)
 A synthetic form
of folic acid is used in
dietary supplements.
 Folic acid the acts by
helping body produc
e 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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52. Chemistry of B9
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53.  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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54. 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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57. 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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58. 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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60. 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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61. References
1. Feeding And Nutrition Of Companion And Hobby Animals ,János Tossenberger
(2011) , Kaposvar University
2. Vitamin B1 [Thiamine] Medicinal Chemistry By P. Ravisankar [ Source]
3. Vitaminb2[riboflavin] Medicinal Chemistry,by P.Ravisankar [Sources Of Vitamin
B2,chemistry Of Vitamin B2,physiological Importance,synthesis Of
Riboflavin,reactions, Vitamin B2 Deficiency Symptoms,functions,uses Of
Riboflavin.
4. By Dr. Edward Group Dc, Np, Dacbn, Dcbcn, Dabfm
Published On March 19, 2015, Last Updated On April 24, 2017
5. Michael B. Davies, John Austin, David A. Partridge: Vitamin C- Its Chemistry
And Biochemistry
6. Dr. P. Ravisankar M. Pharm., Ph.D
7. Ossama Motawae, Marketing Manager
8. Https://Www.Dsm.Com/Markets/Foodandbeverages/En_us/Products/.../Vitamin-
b3.Html
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