Pharmaceutical Chemistry – II (Biochemistry)

VITAMINS
Dr. Abida Latif
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INTRODUCTION
Definition:
These are the organic compounds essential for the proper functioning of body.
They’re required in small amount.

OR

Vitamins are heterogeneous group of naturally occurring essential organic

substituents of the diet which in minute amounts are required by the body for a variety
of essential metabolic functions.

Classification:
The vitamins are chiefly supplied by diet (fruits, vitamin supplements) through
some vitamins can be synthesized in the body itself in appreciable quantities. There
are two types of vitamins.

I. Fat Soluble Vitamins

II. Water Soluble Vitamins

Fat Soluble Vitamins:

 They’re soluble in fats. They’re absorbed by fat globules but that travel
through the small intestine and then into general blood circulation within the
body.
 They’re stored in liver and fat tissues.
 Their deficiency results in skin disease, born diseases, sterility and bleeding.
 Their deficiency requires a large dose of vitamin intake.
 They’re toxic, if taken in excess resulting in Hypervitaminosis.
 In order to maintain normal blood level of these one must know the required
daily allowance (RDA).
 They’re:

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 o Vitamin A (retinol) – helps in vision and growth
o Vitamin D (calciferol) – sunshine vitamin
o Vitamin E (Tocopherol) – anti-oxidant
o Vitamin K (blood coagulant)

Water Soluble Vitamins:

 They’re dissolved in water which means that these vitamins dissolve quickly in
body and they’re carried to body tissues but body can’t store them and excess
amount of water soluble vitamins simply pass through the urine.
 Their deficiency results in anemia and scurvy.
 Their deficiency requires regular intake of deficiency vitamin and lead to a
condition called hypovitaminosis.
 They are:
o Vitamin C (Ascorbic Acid)
o Niacin (Nicotinic acid)
o Pantothenic acid
o Lipoic acid
o Biotin (Vitamin H)
o Vitamin B complex
 Vitamin B1 (Thiamin)
 Vitamin B2 (Riboflavin)
 Vitamin B6 (Pyridoxine)
 Vitamin B12 (Cyanocobalamin)

Comparison of Two Major Types of Vitamins

FAT SOLUBLE WATER SOLUBLE
Solubility in fat Soluble Not soluble
Solubility in water Not soluble Soluble
Absorption Along with lipids, require Absorption is simple
bile salts
Carrier protein Present No carrier protein
Storage In liver No appreciable storage
Excretion Not excreted Excreted
Deficiency Manifests only when stores Manifests rapidly as there is
are depleted no storage
Toxicity Hypervitaminosis Hypovitaminosis
Treatment Single large doses Regular dietary intake
Major examples A, D, E, K B complex and C

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 FAT SOLUBLE VITAMINS
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VITAMIN ‘A’
Other Names:

 Retinol
 Growth Vitamin

Physical Properties:

 Vitamin A is quiet heat stable, but it is destroyed at high temperature in the

presence of O2 or air.
 Sunlight also promotes vitamin A decomposition.

Occurrence:

 It occurs only in nature i.e. in animal kingdom.

 It occurs in highest concentration in the liver oils of certain species of fish e.g.
halibut (richest source), shark and cod.
 It is also present in livers of other animals’ egg yolk, butter, cheese and whole
milk.

Chemistry:

 Vitamin with vitamin A activity is referred as retinols.

 Its oxidative products retinaldehyde (retinal or retinene) is also biologically active
compound.

Vitamin A: (All trans- retinol) C20H30O:

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Retinaldehyde C20H28O:
In retinaldehyde –CH2OH group is replaced by –CHO.

Retinoic Acid:

 In retinoic acid or vitamin A acid, -CH2OH group is replaced by –COOH.

 Poly-isoprenoid compounds are converted into β-ionone ring or Trimethyl
cytohexenyl ring system.

Vitamin A2:
In it, there is an extra double bond between C3 and C4. It is present in liver of
fresh water fish.

β-Carotene C40H56:
It is precursor or pro-vitamin of vitamin A i.e. β-carotene is 2 𝛽-isomer ring
connected by polyprenoid or hydrocarbon chain.

There are several isomer of vitamin A; the most important of these are β-cis
retinol found in many fish liver oils and 11-cis retinol which occur in retina.

Required Daily Amount:

 Vitamin A required amount for an adult man is about 5000 IU.

 Pregnancy and lactation increases its value up to 10-15000 IU.
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Provitamin:

 The colostrums is very high in vitamin A, but the cow’s milk and breast milk don’t
supply retinol to child.
 In plants, it occurs as its precursor, pro-vitamin A i.e. carotenes which are yellow-
red pigments found specially in carrots, yellow corn, sweet potato, peaches and
spinach.
 The carotenes don’t have vitamin A activity, but these are converted to vitamin A
in the liver.

Biological and Physiological Roles:

 Vitamin A helps in:

o Normal reproduction
o Vision (Intensive testing of vitamin A was used to determine its role in the
process of vision. In the rods of the retina is the visual pigment rhodopsin.
These cells react to light signals of small intensity, but they are not sensitive to
light. Active ingredient in the vision process is the oxidized form of retinol
(named retinal) or vitamin A aldehyde associated with protein opsin, together
giving rhodopsin that actis against night blindness and low vision)
o Glycoprotein synthesis
o MPS synthesis
o Mitochondrial membrane function
o Bone and teeth formation
o Gene expression and tissue differentiation
 Β-carotene is an anti-oxidant, hence prevents cancer.
o It appears that β-carotene has a role as an antioxidant, and therefore reduces the
incidence of various cancers. It was observed that the in people who consumed
insufficient amounts of vitamin A for long period the possibility of contracting
lung cancer is much higher than in those who consumed this vitamin in
sufficient quantities. This is particularly pronounced in smokers (with
insufficient intake of vitamin A). Various studies have shown that this does not
apply only to lung cancer, but cancer of the throat, bladder, stomach, colon and
prostate.
 Vitamin A has effect on:
o Epithelium
o Eye changes
o Changes in respiratory tract
o Changes in Skin
o Decreased taste sensation (hypogeusis)
 It helps to maintain immune system.
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Hypervitaminosis:

 Acute Hypervitaminosis (e.g. eating liver of polar bear) A can cause headache,
nausea, vomiting, seizures, vertigo, drowsiness and anorexia.
 Excessive intake of vitamin A can cause bone disease, because an increased
absorption of vitamin A can prevent calcium intake into bones, then calcium levels
(which are not absorbed by bones) in the blood increases. However, this disorder is
very rare in humans.

Hypovitaminosis:

 Vitamin A doesn’t occur in vegetable oils or their hydrogenated products;

ingestion of these products as the body only source of dietary fat is likely to result
in vitamin A deficiency.
 It can cause xerothalmia (blindness), Hypercalcemia and Excessive dryness of
skin.
 Vitamin A deficiency is associated with high levels of infectious diseases. This
deficiency allows infectious agents to effect the digestive tract and respiratory
system. Adding vitamin supplements could avoid this, and organism is more
resistant to infectious agents and reduces the possibility of diarrhea and other
symptoms.

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VITAMIN ‘D’
Other Names:

 Calciferol
 Anti-Richet Vitamin
 Sunshine vitamin

Introduction:

 It is a hormone which regulates calcium absorption and homeostasis.

 It is formed by the action of UV rays on natural precursor sterols present in skin.
 It promotes calcification of body structures.

Physical Properties:

 Pure vitamin D2 and D3 are white odorless crystals soluble in alcohol and
chloroform.
 It may be stabilized by dispersion in gelatin or similar protective coating.

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 It is stable for long periods in oil solution but quite unstable in presence of mineral
salts (tri-calcium phosphate) when compounded in tablet form.

Source:

 Cod liver and other fish liver oils (best source)

 Flesh of oily fish and egg yolk (good source)
 Milk (poor source)
 Ergot / vegetable (source of D2)
 Animal origin (source of vitamin D3)

Chemistry:
Its biological precursors (pro-vitamin) are:

 Ergosterol
 7-dehydrocholesterol

Provitamins are found both in plants and animal tissues.

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Biochemical and Physiological
Roles:

 In active form it acts as hormone i.e.

1, 25-dihydrocholaciferol (calcitriol)
and regulates calcium homeostasis.
 Both choleclciferol and ergocalciferol
are hydroxylated in liver at 25-position. A protein (D-binding protein) moves
vitamin D from skin or intestine to liver. It is also involved in transfer of 25-
hydroxylated derivative from liver to kidney. When the body demand of calcium is
high, the concentration of calcitriol increases in blood. This is mediated by
parathyroid hormone which stimulates the production of calcitriol in kidney while
increasing the activity of 1-hydroxylase.
 It promotes mineralization of body by increasing osteoblasts.
 It acts as co-enzyme for alkaline phosphatases.
 It promotes enameling of teeth and growth.

 Calcitriol increases the capacity of mucous cells of duodenum and jejunum for
absorption of calcium and phosphate.
 It also influences citric acid metabolism, yet not explained.

Required Daily Amount:

 Daily amount for children = 10μg (400 IU)

 Daily amount for adults = 5μg
 Daily amount for nursing mothers = 10μg

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Hypervitaminosis:

 Hypervitaminosis may result into loss of appetite, nausea, vomiting, intense thirst
and pleurae
 Effected children possess muscle wasting; calcification of soft tissues likes artery,
lungs and kidney.

Hypovitaminosis:

 Rickets in children that is characterized by deformation of bones i.e. bone bearing

bones bend.
 Osteomalacia in adults i.e. bones softness, bone ashes and pains. Patients are prone
to get fracture.

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VITAMIN ‘E’
Other Names:

 Anti-sterility vitamin
 Tocopherol

Introduction:

 It was first discovered in 1936.

 It has different degrees of anti-sterility factors.
 It possesses several anti-oxidant properties.
 It includes a group of eight compounds i.e.
α, β, γ, δ, ɛ1, ɛ2, ɠ1, ɠ2,
 Among these α, β, γ and δ are important.

Physical Properties:

 Greenish, yellow, odorless, viscous oily liquid

 Freely soluble in organic solvents and fixed oils

Sources:

 Tocopherols are abundantly present in wheat gram, rice grams, corn grams, other
seeds grams, lettuce, soya and cotton seed oils.
 There is evidence that some green leafy vegetables and rosehips contain more
vitamin E than wheat gram.

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Basic Structure:
Basic structure of tocopherols shows that:

 Chromane ring (tocol)

 Trimethyl tridecyl (saturated side hydrocarbon chain)

Following are some methyl substituted tocol derivatives

 α – Tocopherol → 5, 7, 8 – Trimethyl tocol

 β - Tocopherol → 5, 8 – Dimethyl tocol
 γ - Tocopherol → 7, 8 – Dimethyl tocol
 δ - Tocopherol → 8 – Methyl tocol

Chemistry:
1. α – Tocopherol or 5, 7, 8 – Trimethyl tocol (C29H50O2)

2. β – Tocopherol or 5, 8 – Dimethyl tocol (C28H48O2)

3. γ – Tocopherol or 7, 8 – Dimethyl tocol (C28H48O2)

4. δ – Tocopherol or 8 – Methyl tocol

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Biochemical and Physiological Roles:

 It is powerful anti-oxidant in cell membrane and plasma lipoproteins.

 Free radicals are continuously generated in living systems; products of oxidative
deterioration of polyunsaturated fat would attack bio-membranes. Vitamin E
converts free radicals into non-harmful forms.
 It protects RBCs from hemolysis by preventing the per-oxidant, if reaps the
structures and functional integrity of all cells.
 It slows down aging process which is due to cumulative effects of free radicals.
 It participates in nucleic acid metabolism because tocopherols are component of
cytochrome reductase which is segment of terminal respiratory chain.
 It also has a role in protein synthesis.
 It has been investigated to have an effect on other enzymes e.g. creatinine kinase
and liver xanthine oxidase.
 It has a role in Heam synthesis.
 It prevents hepatic necrosis.

Required Daily amount:

Required daily dose of vitamin E in different situations is as follows.

 Males = 10 mg / day
 Female = 8 mg / day
 Pregnancy = 10 mg / day
 Lactation = 12 mg / day

Hypervitaminosis:
It is observed only in large doses in animals cause reversible symptoms on:

 Skeletal muscle-weakness
 Gastrointestinal disorders
 Disturbance of reproductive functions

Hypovitaminosis:

 Human deficiency has not been reported yet.

 In volunteers, Vitamin E deficiency produced:
o Increase fragility of RBCs
o Muscular weakness
o Creatinine urea

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 VITAMIN ‘K’
Other Names:

 Anticoagulant Vitamin

Introduction:

 It is Well known for the important role it plays in blood clotting

 It is discovered as a result of investigation into the cause of a bleeding disorder
 The name vitamin K stands for Koagulation Vitamin given by a Dam (1929), a
Danish scientist, to a substance that prevented hemorrhagic tendency.

Properties:

 It is Heat Stable
 It is sensitive to light and oxidizing agents, X- rays, radiation, air pollution, aspirin,
mineral oil.
 In frozen food, activity of vitamin can be lost.

Sources:

 Natto (Fermented Soy)

 Spring Onions (Scallions)
 Brussels Sprouts
 Cabbage
 Dairy (fermented)
 Prunes
 Cucumbers
 Dried Basil
 Animal Tissues
 Normal flora of GIT forms Vit. K2 (gram +ve)

Chemistry:
All vitamins have a basic ring structures which
is 2-methyl-1,4-naphthoquinone.

Vitamin K1 (Naturally Occurring):

 Phylloquinone (C31H46O2)
 Oily liquid boils at 20 degree

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 2-methyl- 1,4 - naphthoquinone, with a 3-phytyl substituent
 The normal dietary source found in green vegetables
 Light sensitive – rapidly decomposes under action of UV rays

Vitamin K2 (Naturally Occurring)

 Menaquinones
 It is present in crystalline substance melts at 50 – 52 degree.
 It is synthesized by intestinal bacteria, with different lengths of side chain.
o Menaquinone – 4 (n = 4; C = 30)
o Menaquinone – 7 (n = 5; C = 35)

Vitamin K3 (C11H8O2)

 Doesn’t occur naturally

Vitamin K4

 Doesn’t occur naturally

 Menadiole diacetate

Vitamin K5

 Doesn’t occur naturally

 2-Methyl-4-amino-1-naphthol hydrochloride

Biochemical Effects:

 It helps in the formation of blood clotting factors II (prothrombin), VII, IX and X

by the liver.
 It is used to avoid risk of bleeding after a surgery, often supplements of vitamin K
are recommended.
 Vitamin K however does not form part of the structures of any of these
compounds, but by postranslational modification it brings changes in their
molecules.

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 It appears to have some role in ETC system because its structure is similar to
coenzyme Q.
 It is an essential component of photosynthetic process.
 It helps in preventing osteoporosis and bone fractures.
 Bile salts are needed for the absorption of vitamin K1 and K2 which enter the
blood by way of lymph; in the plasma these are carried in combination with
albumin. Vitamin K stored to the body tissues to a limited extent only.

Required Daily Amount:

 Males = 120 μg/day

 Females = 90 μg/day
 Lactation and Pregnancy = μg/day

Hypervitaminosis:

 Hypervitaminosis K is unique as the upper limit is less clear as is its

bioavailability.
 Toxicity has not been reported.

Deficiency:

 Average diets are usually not lacking in Vit. K and primary deficiency rose in
healthy adults.
 Conditions associated with deficiency of Vitamin K and lead to bleeding
tendencies are:
o Faulty absorption of Vitamin K due to lack of bile as occur in obstructive
jaundice and biliary fistula.
o Diarrheal diseases e.g. sprue, celiac disease and ulcerative colitis interfere
with absorption of vitamin K.
o Administration of multiple broad spectrum antibiotics. These kill the
normal flora of the intestine and stop synthesis of vitamin K.
o Administration of drugs having anti-vitamin K activity.

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 o Patients of uremia, those on parenteral nutrition and those with recent surgery
are also likely to suffer from vitamin K deficiency.
 In newborn babies especially premature ones. Vitamin K doesn’t easily pass
through placental barrier. Breast milk is deficient in this vitamin and the
newborn’s liver doesn’t function well due to immaturity. This result in
hypoprothrombinemia of the newborn who may suffer from intracranial bleeding
as well as bleeding from the skin or GIT. In selected cases, vitamin K is given to
the mother before childbirth or to the baby immediately after birth to prevent
bleeding in the newborn.

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FAT SOLUBLE VITAMINS

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VITAMIN ‘B1’
Other Names:

 Thiamine
 Thiamin
 Aneurine
 Anti-neuritic
 Anti-beriberi factor

Properties:

 It is a white, crystalline compound.

 It is soluble in water.
 It is slowly destroyed by moist heat.
 It is not destroyed if cooking temperature is not much above 1000C.
 It has yeast like odor.

Chemistry:
It has a pyrimidines and a thiazole part in its molecule which are linked by a
methylene bridge.

Sources:

 Richest source includes:

o Dried yeast (3.6 mg/100g)

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 o Rice polishing (2/3 mg)
o Bran, oil seeds
o Wheat gram (1.5 – 2.5 mg)
o Whole cereals (0.4 – 0.1 mg)
o Meat (0.3 – 0.4 mg)
 Poor sources include legumes, beef, liver, nuts, white eggs, fish and vegetable

Note:

 Total conc. Of thiamine in body of an adult is in range of 20 – 25 mg.

 White flour, polished rice and white breakfast cereals are very deficient because
milling causes the loss of a large amount of this vitamin.
 Milk is also deficient of this vitamin.

Physiological Roles:

 The co-enzyme form of thiamine is Thiamine pyrophosphate (TPP). It is used in

oxidative Decarboxylation of alpha-ketoacids e.g. pyruvate decarboxylase.
 It is a component of the pyruvate dehydrogenase (an enzyme) that catalyzes the
breakdown of pyruvate to acetyl Co-A and CO2.
 Biochemical requires TPP in the oxidative Decarboxylation of α-ketoglutarate to
succinyl Co-A and CO2.
 Other groups of enzymes that use TPP as co-enzyme are transketolases in the
hexosemonophosphate shunt pathway of glucose.
 Thiamine diphosphate is the co-enzyme for 3 multi-enzymes that catalyzes
oxidative Decarboxylation reaction in carbohydrate metabolism.
 The main role of thiamine is in carbohydrate metabolism so the requirement of
vitamin B1 is increased along with higher intake of carbohydrate.
 It has central role in energy yielding metabolisms.
 In patients on parenteral nutrition, who receives all those calories in the form of
glucose than thiamine requirement are quite high.
 Thiamine triphosphate has a role in nerve conduction; activates; a chloride channel
in nerve membrane.

Required Daily Amount:

RDA for thiamine is 1 – 1.5 mg/day.

Deficiency Manifestation:
Thiamine deficiency results in server neuromuscular syndrome such as Beriberi
which may be classified into many types.

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 Dry beriberi:
o Chronic diseases in adults in which polyneuropathy occurs is not known
 Wet beriberi:
o It is acute disease in which cardiac failure is of high output type, retention of
Na+ and water leading to edema are the principal signs.
 Acute beriberi

The deficiency of thiamine can be seen in first year of life and is marked by
CVS abnormalities (infantile beriberi)

 Other forms of B1 deficient which are seen clinically are alcoholic polyneuritis
with motor and sensory defects in chronic alcoholics. Alcohol utilization needs
large doses of thiamine, at the same time alcoholics take less nutritive food leading
to its deficiency.

The signs and symptoms of beriberi are:

 Loss of strength
 Paralysis
 Fatigue
 Headache
 Nervousness
 Dizziness
 Loss of appetite
 Lactic acidosis

The reason for regional difference in the clinical picture of beriberi is not
known.

Hypervitaminosis:
Hypervitaminosis has not been reported yet.

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VITAMIN ‘B2’
Other Names:

 Riboflavin

Physical Properties:

 It is an orange yellow crystalline compound.

 It is soluble in water to a limited degree.
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 It is heat stable.
 It is sensitive to light forming lumiflavin
which has a methyl group in place of D-
Ribityl group.
 On reduction, a colorless inactive compound
called leuko-riboflavin results.
 Its watery solution exhibits yellow-green
fluorescence.

Chemistry:

 Chemically, it contains d-Ribitol (ribose

alcohol) attached to heterocyclic present
chemistry.
 Structurally, it is dimethylisoalloxazine or simply it is called as 7,8-dimethyl–10–
(1’ Ribityl) isoalloxazine.

Dietary Source:

 Richest sources include liver, dried yeast, egg, whole milk and milk powder.
 Good sources are fish, whole cereals, legumes, green leafy vegetables, fruits and
most root vegetables.
 Pasteurization of milk results in an appreciable loss of this vitamin.

Required Daily Amount:

A daily dietary intake of about 1.1 – 1.7 mg and increased quantity needed
during pregnancy and lactation.

Biochemical Functions:

 This vitamin occurs as free riboflavin or as constituent of flavoproteins which act

as enzymes called flavoenzymes.
 Riboflavin forms two co-enzymes i.e. riboflavin monophosphate usually called as
Flavin mononucleotide (FMN) and Flavin adenine dinucleotide (FDA).
 FMN is the co-enzyme of cytochrome-C reductase and L-aminoacid
dehydrogenase etc.
 The formation of FMN and FAD is increased by the thyroid hormone and adrenal
steroids. The enzymes containing riboflavin are called flavoproteins. These
enzymes catalyze redox reactions.
 FAD is the co-enzyme for xanthine oxidase, liver aldehyde oxidase and acyl-CoA
dehydrogenase.

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 Riboflavin + ATP → FMN + ADP
FMN + ATP → FAD + PPi
 Flavin co-enzymes are electron carriers in oxidoreductase reactions.
 B2 is absorbed from the upper GIT by the specific transport mechanism in which it
is first converted to FMN by the enzyme flavokinase. This process is activated by
the thyroid hormones and is depressed by drugs. When taken in physiologically
needed amounts, only 9% appears in urine, but urine excretion increases with a
greater intake. It is synthesized by bacteria in the colon, but that is not absorbed.

Deficiency:
No specific deficiency disease is caused by riboflavin deficiency. Its deficiency
is widespread but not fatal. Following are some symptoms of features that can be seen.

 Inflammation of lips
 Eyes disturbance
 Neuropathy
 Bone marrow shows erythroid hypoplasia
 Dermatitis of trunk
 Inflammation of tongue with atrophy

Toxicity:
Toxicity of vitamin B2 has not been reported yet but large doses result in light
yellow decolorisation of urine.
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Vitamin ‘B3’
Other Names:

 Vitamin PP
 Bionic
 Nicotinic acid

Physical Properties:

 This is a colorless translucent, water-soluble solid.

 It is odorless and has sour taste.

Dietary Sources:

 Best sources include liver and kidney.

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 Good source of vitamin B3 includes meat, fish, eggs, milk and peanut.

RDA:

 RDA for niacin for women and men are 11 mg/day and 12 mg/day, respectively.
 RDA for pregnancy is 18 mg/day.
 RDA for lactation is 17 mg/day.

Chemistry:
Niacin is the generic term for nicotinic acid (pyridine – 3- carboxylic acid) and
its amide derivative nicotinamide that also exhibits vitamin activity of nicotinic acid
and to which nicotinic acid is converted.

(Nicotinamide) (Nicotinic acid)

Biochemical Roles:

 It is a part of two co-enzymes NAD+ and NADP+, whose vital roles are co-
enzymes in biological oxidation.
 Both NAD+ and NADP+ are involved in DNA repair and calcium mobilization.

Deficiency:
Deficiency of vitamin B3 causes pellagra which is characterized by rough skin
(mainly in areas where maize is main diet and good quality protein is low) and can
affect skin, GIT and nervous system.

Hypervitaminosis:
Hypervitaminosis has not been reported yet.

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VITAMIN ‘B5’
Other Names:

 Pantothenic acid

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Physical Properties:

 It is a viscous yellow liquid.

 It is stable to moist heat but is destroyed by dry heat.
 It is commercially available as sodium and calcium salts.

Dietary Sources:

 It is widely spread and occurs specially in liver, kidney, eggs, milk, peas,
cauliflowers, cabbage, potatoes and tomatoes.
 Major food sources of vitamin B5 are dried mushroom, dried egg yolk and
sunflower seeds.

Chemistry:
The intestinal E. coli synthesize it, which may be absorbed. This vitamin is
very unstable. Pantothenic acid is an amide between pantothenic acid and β-alanine.

Required Daily amount:

 RDA for this vitamin is 3 – 5 mg/day.

 During pregnancy and lactation, this amount is increased up to 6 – 7 mg/day.

Biochemical Functions:

 Pantothenic acid is first changed in the body to 4-phosphopantotheine by

phosphorylation and linkage to thioethanoalamine which forms a part of molecule
of co-enzyme A (CoA-SH).
 Coenzyme A is concerned with the metabolism of lipids, proteins, and
carbohydrates and takes part in many physiological reactions e.g.
o Formation of acetyl CoA
o Formation of succinyl CoA
o In oxidation of fatty acid
o Utilization of acetoacetic acid
o Synthesis of cholesterol
o And many other biochemical reactions
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 It also occurs in molecule of acyl carrier protein (ACP) which takes part in
biosynthesis of fatty acids.
 Folic acid and biotin seem to be needed for the utilization of this vitamin.
 It takes part in the post-translational modification of proteins, e.g. N-terminal
acetylation, acetylation of internal amino acids and fatty acid Acylation.

Hypervitaminosis:
Toxicity for pantothenic acid has not been reported yet.

Deficiency:
Its deficiency is rare. But the extreme deficiency can cause:

 Irritability, restlessness, disturbed sleep rhythm and excessive fatigue

 Gastrointestinal disturbances
 The response of the adrenal cortex to ACTH is diminished
 Burning feet syndrome

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‘VITAMIN B6’
Other Names:

 Pyridoxine

Physical Properties:

 It is water soluble and heat stable.

 It is basic in nature.
 It is a colorless crystalline substance.
 It is sensitive to heat, UV rays and alkalies.
 It is convertible to its aldehyde and amino form.

Dietary Sources:

 Rich sources of vitamin B6 are dried yeast, egg yolk, meat, rice polishing, fish,
milk, whole grains, cabbage, legumes, seed oils and in green leafy vegetables.
 It is present in all food groups.

Chemistry:

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 Chemically, it is 4,5-di(hydroxymethyl)-3-hydroxy-2-methylpyridine. The
aldehyde and amine form of the vitamin are Pyridoxal and Pyridoxamine. These
all forms have same level of vitamin activity and are inter-convertible.

(Pyridoxine) (Pyridoxal) (Pyridoxamine)

 Pyridoxal and Pyridoxamine occur at nature in form of phosphates and acts as

coenzymes.

(Pyridoxal phosphate) (Pyridoxamine phosphate)

Required Daily Amount:

 RDA of this vitamin is 1-2 mg/day.

 During pregnancy and lactation, it is increased up to 2.5 mg/day.

Biochemical Functions:

 Active form of pyridoxine is Pyridoxal phosphate (PLP) which acts as coenzyme

for many reactions on amino acid metabolism (more than 600 types of reaction in
body).
Pyridoxal + ATP → Pyridoxal phosphate
 PLP in part of enzymes catalyze transmainases in trans-amination reaction.
 All Decarboxylation reactions of amino acids require PLP as co-enzyme e.g.
Glutamic acid → γ-Aminobutyric acid (GABA) + CO2
GABA is inhibitory neurotransmitter. Its deficiency can cause epilepsy in children.
 PLP plays an important role in Methionine and cysteine metabolism. Hence in
deficiency of B6, hemocystein level in blood is increased and kevel of

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 hemocystein is corrected with myocardial infarction and therefore B6 is used in
clinical practice to prevent cardiac diseases.
 Alanine synthase is also PLP dependent enzyme. This is rate limiting step in heme
biosynthesis. So anemia is common.
 Conversion of glycine to serine by serine hydroxymethyl transferase is also PLP
dependent.
 It helps in entry of K+ ion and amino acid into the cell against the concentration
gradient.
 It is involved in the biosynthesis of arachidonic acid from linolic acid and also has
role in steroid metabolism.
 Vitamin B6 is a cofactor of the molecule of glycogen phosphorylase and makes
this enzyme stable.
 PLP is a coenzyme for threonine aldolase that catalyzes the reaction.
Threonine → Glycein+ Acetaldehyde
 It takes part in the formation of niacin from tryptophan.

Deficiency:
Symptoms of the deficiency appear:

 After prolonged deficiency

 In young adults
 In pregnant women

Symptoms are:

 Erythropoiesis, skin and nervous system disorders

 Anemia
 Young infant shows digestive troubles and convulsions
 CVS diseases, inflammatory diseases and certain cancers

Hypervitaminosis:
Toxicity of vitamin B6 has not been reported yet. But it can cause severe
neuropathy.

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VITAMIN ‘B7’
Other Names:

 Biotin

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 Vitamin H
 Co-enzyme R

Physical Properties:

 Biotin has long colorless needle-like crystals.

 It is only slightly soluble in water and is heat stable.
 It is a monocarboxylic acid.

Dietary Sources:
Biotin is synthesized by intestinal bacteria, but there is a lack of good quality
studies about how much biotin they provide.

 Brewer's yeast
 Soybeans
 Beef liver
 Butter
 Split peas
 Sunflower seeds
 Green peas/lentils
 Peanuts/walnuts
 Pecans
 Eggs
 Raw egg whites contain a protein (avidin) that blocks the absorption of biotin, so
people who regularly consume a large number of eggs may become biotin-
deficient.
 Biotin is also available in dietary supplements, as an ingredient in multi-vit/min
products or as a biotin-containing supplement with health benefit claims.

Chemistry:
Chemically it is 5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thienol[3,4-di]imidazole-
4-yl]pentanoic acid.

Daily Dietary Intake:

 For women and men over age 18 the Adequate Intake (AI) is set at 40μg/day.
 RDA for pregnancy is 40μg/day, for lactation it is 45μg/day.
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 For children ages 1–17 years the AIs increase with age from 20 to 35μg/day.

Biochemical Roles:
Biotin acts as a coenzyme for the enzymes for the enzymes called carboxylases
that catalyze reactions involving a fixing of CO2 which is first taken up by this
vitamin.
The following reactions (carboxylations) need biotin as a coenzyme.
 Conversion of acetyl CoA to melonyl CoA; this is the first step in the cytoplasmic
biosynthesis of fatty acid.
 Conversion of Pyruvic acid to oxaloacetic acid (pyruvic carboxylase)
 Carboxylation of propionyl-CoA to D-methylmelonyl-CoA
 Conversion of β-methylcrotonyl-CoA (an intermediate of leucine catabolism) to β-
methylglutaconyl-CoA; the latter is changed to HMG-CoA

Deficiency:
Deficiency of biotin is rarely seen clinically but can be produced
experimentally by feeding to volunteers a large amount of raw egg white. The
symptoms may include:

 Perioral dermatitis
 Conjunctivitis
 Alopecia
 Ataxia
 Late development of nervous system in children
 Organic aciduria

Toxicity:
Toxicity has not been reported yet.

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VITAMIN ‘B9’
Other Names:

 Folate
 Folic Acid

Introduction:

 It is a water soluble vitamin.

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 It is named because of it occurrence in foliage of plants.

Chemistry:
Chemically, it is pteroylglutamic acid.

Physical Properties:

 It is a yellow crystalline substance.

 It is slightly soluble in water.
 It is heat stable in neutral or alkaline medium but not in acidic medium.

Occurrence:

 It is widely spread in nature.

 Chief dietary sources include liver, kidney, beef, and wheat and cauliflower.
 It is also synthesized by intestinal bacteria but not in significant amount.
 It is mainly stored in liver.

RDA:

 Its required daily amount is 300-400μg.

 In pregnancy and lactation, this amount becomes 500-600μg/day.

Biochemical Roles:

 Folic acid (F.A) is not active as such. For activation, it is reduced to dihydrofolic
acid (DHFA) and then to tetrahydro folic acid (THFA). Ascorbic acid appears to
be essential for the conversion of FA to THFA.
𝑁𝐴𝐷𝑃𝐻 +𝐻 + 𝑁𝐴𝐷𝑃𝐻 +𝐻 +
𝐹𝐴 𝐷𝐻𝐹𝐴 𝑇𝐻𝐹𝐴
−𝑁𝐴𝐷𝑃+ −𝑁𝐴𝐷𝑃+
 THFA gives rise to several folic acid coenzymes because it can act as a carrier of
various one-carbon groups (i.e. formyl, methyl, methenyl).
 It carries out a large number of reactions in tissue cells.
 It forms purines, thymine and Methionine.

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 Folic acid in the form of folate is used to treat anemia caused by folic acid
deficiency.
 Folate is necessary for maintaining pregnancy.
 It reduces the chances of heart diseases and cancer.
 Folic acid is used for memory loss, Alzheimer’s disease, age-related hearing loss,
reducing signs of aging, osteoporosis, nerve pain and muscle pain.
 Folate is necessary for production and Maintaince of new cells, for DNA and RNA
synthesis.
 It often works in combination with other B vitamins.

Deficiency:

 Deficiency can be caused by unhealthy diets.

 Folate deficiency may lead to glossitis, diarrhea, depression, confusion anemia,
fetal neural defects and brain defects (during pregnancy).
 Other symptoms may include fatigue, hair loss, grey hair, poor growth and swollen
tongue.

Hypervitaminosis:
The risk of toxicity from folic acid is low, because it is water-soluble vitamin
and it is removed from body regularly.

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VITAMIN ‘C’
Other Names:

 Ascorbic Acid (L-ascorbic acid)

 D-isomer of ascorbic acid is biologically inactive

Physical Properties:

 It is water soluble, white crystalline substance.

 It is odorless, and destroyed by heat, exposure to air, alkalies and oxidation.
 It has sour taste.

Occurrence:

 This is synthesized in-vivo from glucose.

 Guava, citrus fruits and tomatoes are best sources of vitamin C.
 Fresh fruits and vegetables are good source of vitamin C.

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 Other sources are green pepper, onion, spinach, cabbage, turnips, melons and
potatoes.
 Animal tissues are not a good source of this vitamin.
 Milk is deficient in it.

Chemistry: (C6H8O)

Ascorbic acid can undergo oxidation from dehydroascorbic acid and after
addition of water in resulting product 2, 3-Diketogluconic acid is produced. The
oxidation and reduction activity of ascorbic acid is very important for body, while 2,
3-Diketogluconic acid has no vitamin C activity.

Biochemical Roles:

 It is involved in conversion of proline present in pro-collagen to hydroxy proline.

It is important for triple helix required structure for normal tissue.
 It acts as anti-oxidant and along with other anti-oxidants e.g. β-carotene and
vitamin E to prevent body from toxic oxidation products.
 It is present in large amounts in glandular tissue especially adrenal cortex and
corpus lutem and is involved in production and synthesis of steroid hormones.
 It helps in reducing Fe3+ to Fe2+ and helps in the intestinal adsorption of iron and
its utilization.
 It is involved in degradation of tyrosine to homogentisic acid and of the lalter to
meleyl acetoacetic acid.
 It takes part in processing of certain polypeptide hormones e.g. ADH and Oxytocin
etc.

Required Daily Amount:

 RDA of ascorbic acid is 45 – 75 mg/day.

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 During lactation and pregnancy, it is increased up to 80 – 120 mg/day.

Deficiency:
Deficiency of ascorbic acid can cause scurvy which is characterized by:

 Anemia, weak erection

 Skin hemorrhages
 Arresting of osteoblastic function at growing ends of long bones
 Slow healing of wounds
 Edema and fever

Hypervitaminosis:
Toxicity for ascorbic acid has not been reported yet.

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“Stop Doubting Yourself, Work Hard and

Make it happen”

Best of Luck!

Muhammad Muneeb
D16M137