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Fat soluble Vitamins - By Dr. P. Ravisankar.

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Dr. P. Ravisankar M. Pharm., Ph.D.
Vitamin A
Vitamin D
Vitamin E
Vitamin K
Definition
Introduction
Classification
Structures,Functions,Deficiency,Diseases,Toxicity and uses.

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Fat soluble Vitamins - By Dr. P. Ravisankar.

  1. 1. 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
  2. 2. 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. 2 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  3. 3. CLASSIFICATION VITAMINS 10/9/2015 Vignan Pharmacy College, Vadlamudi, Guntur 3 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)-
  4. 4. 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. 10/9/2015 Vignan Pharmacy College, Vadlamudi, Guntur 4
  5. 5. VITAMIN 5 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  6. 6. 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 10/9/2015 Vignan Pharmacy College, Vadlamudi, Guntur 6
  7. 7. CH2OH CHO COOH RETINOL RETINAL(Vitamin A aldehyde) RETINOIC ACID STRUCTURES OF VITAMIN-A 7 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  8. 8. Vitamin A, D, E, K FAT SOLUBLE VITAMINS 8 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  9. 9. 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. 9 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  10. 10. 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 10 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  11. 11. Beta-carotene Dark leafy green vegetables, spinach, broccoli. Deep orange veggies Carrots, pumpkin, squash, sweet potato. Deep orange fruits Apricots, cantaloupe. VITAMIN-A SOURCES 11 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  12. 12. 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. 10/9/2015 Vignan Pharmacy College, Vadlamudi, Guntur 12  Retinol
  13. 13.  Retinol  Fortified milk, butter cheese, cream  Fortified margarine  Eggs  Liver  Tomatoes  Papaya  Watermelon, VITAMIN-A SOURCES  Lycopene 13 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  14. 14. 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 14 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  15. 15. 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 15 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  16. 16. VITAMIN-A DISEASES  Deficiencies: – Night blindness – Xerophthalmia (permanent blindness) – Follicular hyperkeratosis – Impaired growth – Increased infections – Increased transmission of maternal/fetal HIV 16 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  17. 17. 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 © 17 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  18. 18. 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. 18 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  19. 19. 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. 19 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  20. 20. VITAMIN-D 20 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  21. 21. 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 21 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  22. 22. • 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 22 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  23. 23. Important structures of vitamin D Ergocalciferol Cholecalciferol Vitamin D5 C2H5 Sitocalciferol Cisergocalciferol
  24. 24. 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 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  25. 25. 25 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  26. 26. 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) 26 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  27. 27. • Fortified – Milk – Margarine – Butter – Cereal • Veal, Beef • Egg yolk • Fatty fish (salmon, sardines, herring) VITAMIN-D SOURCES 27 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  28. 28. • 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 28 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  29. 29. 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 29 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  30. 30. 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) 30 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  31. 31. 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 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  32. 32. VITAMIN-E 32 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  33. 33. * 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 33 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  34. 34. 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 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  35. 35. 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 35 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  36. 36. 36 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  37. 37. 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 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  38. 38. 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) 38 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  39. 39. 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 39 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  40. 40. 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. 40 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  41. 41. 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. 41 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  42. 42. VITAMIN K 42 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  43. 43. *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 43 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  44. 44. Fat-soluble vitamin:K1 (Phylloquinone) K2 (Menaquinone) Synthesized by: • Vegetable and plants. Synthesized by: • Bacterial flora of the gut • Minor source 44 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  45. 45. • Bacterial synthesis in GI tract • Leafy green vegetables • Cruciferous vegetables • Liver • Milk Vitamin K Sources 45 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  46. 46. • 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 46 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  47. 47. 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 Children 4-8 years 55 55 Children 9-13 years 60 60 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 47 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  48. 48. • Chief functions in the body – Synthesis of blood-clotting proteins and bone proteins that regulate blood calcium Vitamin K 48 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  49. 49. • 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 49 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  50. 50. Metabolic Functions of Vitamin K1 Vitamin K1 Promotes Blood Clotting Involved in synthesizing 4 blood-clotting factors! 50 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  51. 51. 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 51 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015
  52. 52. 52 Vignan Pharmacy College, Vadlamudi, Guntur 10/9/2015

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