Fat soluble Vitamins - By Dr. P. Ravisankar.

FAT SOLUBLE VITAMINS
B.VIJAY KUMAR
Dr. PANCHUMARTHY RAVI SANKAR
M. pharm., Ph.D.
VIGNAN PHARMACY COLLAGE
VADLAMUDI, GUNTUR (DT) A.P 1
Vignan Pharmacy College, Vadlamudi,
Guntur
10/9/2015

VITAMINS
INTRODUCTION
 A vitamin is an organic compound required as a nutrient in tiny amounts
for the maintenance and growth of an living organism.
 Vitamins deficiency may lead to certain specific diseases or symptoms
which can be cured by the administration of that specific vitamin only.
 The term vitamin was first discovered by Funk.
 Funk coined the term "vitamine" a combination word from vita and
amine, meaning amine of life.
 At the time they were considered to be amines that are vital for the life.
 After researchers began to suspect that not all "vitamines" had an amine
component (particularly vitamine A).
 How ever it was later found that not all vitamins contains “nitrogen” or
amines.
 In 1920, Drummond proposed that the final "e" be dropped. That’s why
in the word Vitamines “e” is removed and called vitamins.
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CLASSIFICATION
VITAMINS
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Based on solubility in oil Based on solubility in water
Fat soluble vitamins Water soluble vitamins
Vitamin -A Vitamin-D Vitamin-E Vitamin-K
Vitamin-D2 Vitamin-D3 Vitamin-K1 Vitamin-K3
B-complex vitamins Non B-complex
vitamine
Ex: Vitamin-C
Based on type of source
Thermo labile Thermostable
Vitamin-B2 Vitamin-B3 Vitamin-B6 Vitamin-B12 Niacin Folic acid Biotin
Based on Stability
Ex:Vitamin-B1
Retinol Tocopherol
Ergocalciferol Cholecalciferol
Ascorbic acid
Thiamine
Riboflavin Pantothenic acid Pyridoxine Cyanacobalamine Vit-H
Nicotinamide Nicotinic acid
Vitamin-K1 - (Phytonadione) Folic acid -(Pteroylglutamic acid)
Vitamin-K3 - (Menadione) (Niacinamide)-

BASIC STRUCTURAL MOIETY OF FAT SOLUBLE
VITAMINS
FAT SOLUBLE VITAMINS BASIC STRUCTURAL MOIETY
Vitamin - A Diterpenoid
Vitamin – D Steroidal moiety
Vitamin - E
Chromane ring system with
isoprenoid side chain.
Vitamin- K Napthaquinone derivative.
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VITAMIN
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CHEMICAL NATURE AND PROPERTIES OF
VITAMIN-A
Natural form A1 （Retinol）
A2 （3-dehydro-retinol ）
Active form Retinol, Retinal, Retinoic acid
Pro-vitamin A β-carotene
Storage Liver, Adipose tissue of the body
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CH2OH
CHO
COOH
RETINOL
RETINAL(Vitamin A aldehyde)
RETINOIC ACID
STRUCTURES OF VITAMIN-A
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Vitamin A, D, E, K
FAT SOLUBLE VITAMINS
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Fat soluble vitamins
1. Vitamins A, D, E and K are the fat-soluble vitamins.
2. These vitamins are soluble mainly in lipids or oil. So called
as fat soluble vitamins.
3. Excessive use of fat soluble vitamins may lead to their
accumulation in the body (hypervitaminosis) due to
delayed elimination rate. This accumulation of vitamins
results in toxic effects.
4. Fat soluble vitamin tend to be stored in fatty tissues
(adipose tissue) of the body and in the liver.
5. They are eliminated slowly from the body because of their
lipophilic character.
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Vitamin-A
Vitamin-A is a family of fat-soluble Retinoids:
Retinol, Retinal, Retinoic Acid
Retinol Retinal Retinoic Acid
 Animal foods
 Stored in Body
 Function:
Reproduction
 Found in plants
 Retinal = Vision
 Retinoic = Regulates growth
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Beta-carotene
Dark leafy green vegetables,
spinach, broccoli.
Deep orange veggies
Carrots, pumpkin, squash,
sweet potato.
Deep orange fruits
Apricots, cantaloupe.
VITAMIN-A SOURCES
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SOURCE OF VITAMIN-A
 Beta-carotene
 Dark leafy green vegetables, spinach, broccoli
 Deep orange veggies Carrots, pumpkin, squash, sweet potato
 Deep orange fruits, Apricots, cantalo
 Milk, butter, cheese, cream, eggs, liver
 Lycopene
 Tomatoes, papaya, water melon.
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 Retinol

 Retinol
 Fortified milk, butter cheese,
cream
 Fortified margarine
 Eggs
 Liver
 Tomatoes
 Papaya
 Watermelon,
VITAMIN-A SOURCES
 Lycopene
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FUNCTIONS OF VITAMIN-A
(RETINOIDS)
Growth and Development
Embryonic development
Epithelial cells and mucus production in lungs,
trachea, skin, GI tract
Immune Function
Maintains the epithelium
Increased infections w/vitamin-A deficiency
Dermatology
Topical and oral medications
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VITAMIN A DEFICIENCY -
REPRODUCTION
1. In females:
 Increased abortions
 Neonates born dead/weak
 Deformed young: no eyeballs
 Hydrocephalus
2. In males:
 Keratinization of testicular
epithelium
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VITAMIN-A DISEASES
 Deficiencies:
– Night blindness
– Xerophthalmia (permanent blindness)
– Follicular hyperkeratosis
– Impaired growth
– Increased infections
– Increased transmission of maternal/fetal HIV
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Vitamin A Toxicity
There are three syndromes of vitamin A toxicity:
• Acute Toxicity (very rare)
– occurs in adults when >200 mg are ingested
– symptoms include nausea, vomiting, vertigo, and blurry
vision.
• Chronic Toxicity (rare)
– occurs with long-term ingestion of doses higher than 10
times the RDA.
– symptoms include problems talking, hair loss,
hyperlipidemia, hepatotoxicity, bone and muscle pain,
and vision problems.
– In postmenopausal women, it has been associated with
increased fracture risk.
E.A. DENNIS 2010 ©
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Vitamin A Toxicity
• Teratogenic Effects:
– Synthetic retinoids can be used to treat severe
dermatological conditions including severe psoriasis
and acne vulgaris.
– Synthetic retinoids, like acitretin, cause spontaneous
abortions and severe life-threatening congenital
malformations.
• Women treated with retinoids must not get pregnant at
the time of treatment or become pregnant for up to 3
years after treatment.
• Patients receiving treatment with retinoids must not give
blood for up to three years after treatment.
– The presence of these drugs in plasma can be
demonstrated for up to several years after a person
stops taking them. It could be disastrous if an
unsuspecting pregnant woman received one in a
transfusion, hence the ban.
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USES OF VITAMIN-A
1. Vitamin-A is mainly used in the treatment of
treatment of deficiency of Vitamin-A.
2. It is also used in the treatment of
- Dermatological disease and lesions.
- Xerophthalmia.
- Cold, warts, corns and calluses( skin infections
- Acne
- Hyperkeratosis of arms.
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VITAMIN-D
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VITAMIN-D
• Vitamin D = calciferol
• Vitamin D2 = ergocalciferol
Completely synthetic form produced by the irradiation of
the plant steroid ergosterol
Plant source – cannot be used by birds
• Vitamin D3 = cholecalciferol
Produced photochemically by the action of sunlight or
ultraviolet light from the precursor sterol
7-dehydrocholesterol
Animal source – required by birds
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• Infact Vitamin-D1 is containing molecular compound of lumisterol and D2
in 1:1 ratio.
Lumisterol
Vitamin-D1= Lumisterol + Vitamin D2 (calciferol)
( 1 : 1 ) Ratio.
VITAMIN-D1
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Important structures of vitamin D
Ergocalciferol
Cholecalciferol
Vitamin D5
C2H5
Sitocalciferol
Cisergocalciferol

Vitamin D - Cholecalciferol
• Vitamin D is a cholesterol-like
molecule
• Important to bone and calcium
regulation
– Acts more like a steroid
hormone rather than a enzyme
cofactor
E.A. DENNIS 2010 ©7-dehydrocholesterol
• Cholecalciferol (D3) has two sources:
– Diet
• plants have ergocalciferol (D2), which
easily becomes D3
• animal flesh has ready-made D3
– Sunlight (UV)
• Converts 7-dehydrocholesterol into
D3 in the skin
synthesis in skin
Cholecalciferol
Diet
Ergocalciferol
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Table 2: Recommended Dietary Allowances (RDAs) for Vitamin D [1]
Age Male Female Pregnancy Lactation
0–12 months* 400 IU
(10 mcg)
400 IU
(10 mcg)
1–13 years 600 IU
(15 mcg)
600 IU
(15 mcg)
14–18 years 600 IU
(15 mcg)
600 IU
(15 mcg)
600 IU
(15 mcg)
600 IU
(15 mcg)
19–50 years 600 IU
(15 mcg)
600 IU
(15 mcg)
600 IU
(15 mcg)
600 IU
(15 mcg)
51–70 years 600 IU
(15 mcg)
600 IU
(15 mcg)
>70 years 800 IU
(20 mcg)
800 IU
(20 mcg)
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• Fortified
– Milk
– Margarine
– Butter
– Cereal
• Veal, Beef
• Egg yolk
• Fatty fish (salmon, sardines, herring)
VITAMIN-D SOURCES
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• The Sunshine Vitamin
– Approximately 90% of
Vitamin D requirement
obtained from sun
– UV light from sun hits
skin, triggers synthesis
– Activated in liver and
kidneys
VITAMIN-D
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VITAMIN-D DEFICIENCY
• Young animals
– Rickets
• Failure of bones to grow properly
• Results in “bowed” legs or knock-knees, outward bowed
chest and knobs on ribs
• Older animals
– Osteomalacia: Adult form of rickets
• Softening of bones, bending of spine, and bowing of legs
– Osteoporosis (porous bones):
• Vitamin D plays a major role along with calcium
• Loss of vitamin D activity with advancing age
• Associated with fractures  very serious for geriatrics
 Poultry
• Decreased egg production & hatchability
• Thin-shelled eggs
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VITAMIN-D TOXICITY
• Calcification of soft tissue
– Lungs, heart, blood vessels
– Hardening of arteries (calcification)
• Hypocalcaemia
– Normal is ~ 10 mg/dl
– Excess blood calcium leads to stone formation in kidneys
• Lack of appetite
• Excessive thirst and urination
• Chicks: 4 X 106 IU/kg diet (3 to 5x required levels)
• Pigs: 0.25 X 106 IU/d for 30 days
• Infants: 3 X 103 (10x required levels)
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Uses of vitamin D
• Vitamin D is more than just a vitamin: it is also a hormone. Research in the last few
years suggests that Vitamin D – traditionally considered a “bone vitamin.
• Vitamin D is sufficient enough in the treatment of hopoparathyroidism and in
vitamin D deficiency diseases like reckets, osteomalacia.
• It has a role in preventing infections like.
• heart diseases and
• diabetes mellitus.
• The sunshine vitamin vitamin D is used in the treatment of breast and colon
cancers.
• Treatment of psoriasis (chronic skin disease where scaly patches can be seen on
elbows, knees, scalp, etc.,
• and autoimmune diseases such as multiple sclerosis,insulin dependent diabetes
mellitus are decreased by vitamin D intake.
• and rheumatoid arthritis.
• In parallel with this explosion of research, there is a change in the
recommendations for optimum intake of this vitamin-hormone.
• vitamin D is a central player in calcium and bone metabolism. 31
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VITAMIN-E
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* Infact vitamin E is the antisterility factor
which is necessary for fertility of the male and
the birth process of the female and therefore it
is also called tocopherols
* Tokos(Greek) means = for child birth….
phero = to bear
ol = alcohol.
* It is very essential for the birth process in
female
and fertility in males and at the same time
the compound reacts like an alcohol
VITAMIN-E
*This are mainly 8 compounds,
4-tocopherols
4-tocotrienols
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Vitamin E
Alpha-tocopherol most active form in body.
Synthetic form in supplements only ½ as
active.
Position of methyl
groups on aromatic ring
Tocopherol structure Tocotrienol structure
5,7,8 trimethyltocol) alpha-Tocopherol (α) alpha-Tocotrienol
5,8 diemthyltocol) beta-Tocopherol (β) beta-Tocotrienol
7,8 dimethyltocol) Gamma tocopherol (γ) Gamma-Tocotirenol
8 mono methyl tocol Delta-tocopherol (δ) Delta-tocotrienol34
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sources
• Dietary sources and supplements
• The following foods are rich in
vitamin E.
. Seeds and seed oils, like
sunflower and safflower.
• nuts and nut oils, like
almonds
• green leafy vegetables, like
spinach, turnip.
• tomatos
• mangoes
• asparagus
• papayas
• pumpkin
• sweet potato
• blue crab
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Vitamin E - Functions
• Stabilize reactions or
situations that typically
produce free radicals
– Nucleic acid and protein
metabolism
– Mitochondrial metabolism
– Supplementation may
increase antibody
production
– When supplemented prior
to slaughter, helps maintain
meat quality (shelf life,
color) 37
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Vitamin E - Deficiency
• Rare – typically associated with fat malabsorption or
excessive intake of polyunsaturated fatty acids
(PUFAs)
– Erythrocyte hemolysis and hemolytic anemia
• Red blood cell breaks open and spill the contents, perhaps due to
PUFA oxidation
• Observed among newborns of several species
• Vitamin E treatment resolves hemolytic anemia
– Prolonged deficiency causes neuromuscular dysfunction;
affects the spinal cord and the retina
• Degeneration of nerve cells (poultry)
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Vitamin E - Deficiency
• Reproductive failure
– Embryonic degeneration
– Ovarian failure
– Testes degeneration
– Fetal resorption
• Derangement of cell permeability
– Liver, brain, kidney, or blood capillaries
– Brain necrosis (crazy chick disease)
• Muscular lesions
– White muscle disease (calves, lamb)
– Mulberry disease (pigs)
– Stiff lamb disease (skeletal muscle degeneration)
• Failure to growth, unthriftiness
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Side effects/adverse effects.
• Taking vitamin E supplements for up to 4 months at doses of 530 mg
or 800 IU (35 times the current RDA) had no negative side-effect on
general health,
• body weight,
• levels of body proteins,
• lipid levels,
• liver or kidney function
• thyroid hormones
• amount or kinds of blood cells
• and bleeding time over doses may cause Nausea,vomitng,diarrhoea.
• vitamin E products in excess of 1200 IU daily may interfere with absorption and metabolism
of vitamins A and K. But one can get benefits with much lower levels of vitamin.
• individuals who are vitamin K(people who are on blood thinners) deficient should not take
alpha-tocopherol supplements without close medical supervision because of the increased
risk of hemorrhage.
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Physiological role/importance of vitamin E
• Vitamin E plays an important role as an antioxident 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
deterioration(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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VITAMIN K
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*Vitamin K is a fat-soluble vitamin that plays
*Vitamin K is known as the clotting vitamin .
* They are 2-methyl-1,4-naphthoquinone
*Vitamin K exists in both natural and
*The natural forms of vitamin K include
*while synthetic froms are vitamin
an important role in blood clotting
derivative
forms.
K1(phylloquinone and
K2 (menaquinone from the purified fish meal,
K4(menadiol sodium phosphate
K3(menadione
*Vitamin K1 is also called phylloquinones, is
*The second basic type, called menaquinones,
is made by bacteria in the large intestine
made by plants.
is made by bacteria in the large intestine .
VITAMIN K
synthetic
*Vitamin K (K from "Koagulations-Vitamin”.(clotting of blood)in German
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Fat-soluble vitamin:K1 (Phylloquinone) K2 (Menaquinone)
Synthesized by:
• Vegetable and plants.
Synthesized by:
• Bacterial flora of the gut
• Minor source
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• Bacterial synthesis
in GI tract
• Leafy green
vegetables
• Cruciferous
vegetables
• Liver
• Milk
Vitamin K Sources
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• Vitamin K1 produced by plants and algae
– Broccoli, kale, chard; plant oils like canola and
soybean
• Hydrogenated soybean oil has ineffective K
• Vitamin K2 produced by bacteria in gut
– Food Sources: fermented soybean (Natto);
dairy products, egg yolk
Vitamin K Sources
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What are current public health recommendations for vitamin K?
Adequate Intake (AI) for Vitamin K
Life Stage Age
Males
(mcg/day)
Females
(mcg/day)
Infants 0-6 months 2.0 2.0
Infants 7-12 months 2.5 2.5
Children 1-3 years 30 30
Adolescents 14-18 years 75 75
Adults
19 years and
older
120 90
Pregnancy
18 years and
younger
- 75
Pregnancy
19 years and
older
- 90
Breast-feeding
18 years and
younger
- 75
Breast-feeding
19 years and
older
- 90
Recommended Daily Intake
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• Chief functions in the body
– Synthesis of blood-clotting proteins and
bone proteins that regulate blood calcium
Vitamin K
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• Synthesis of bone proteins that regulate
blood calcium; prevent bone loss
• Integration of calcium into bones
• Prevent calcium deposition in blood
vessels (vascular calcification)
• Maintain blood vessel elasticity
Vitamin K: Other Functions
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Metabolic Functions of Vitamin K1
Vitamin K1 Promotes Blood Clotting
Involved in synthesizing 4 blood-clotting factors!
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TOXIC & DEFICIENCY OF VITMIN K
• No known adverse Toxicity
• If on anticoagulant medications should keep vitamin K
intake consistent! Changes in intake can increase or
decrease drug effectiveness.
• Deficiency
• Heart Disease and Vitamin K deficiency go hand in hand!
• Deficiency severe enough to affect blood clotting is
extremely rare.
TOXIC EFFECT
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Fat soluble Vitamins - By Dr. P. Ravisankar.

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