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VITAMIN E (MEDICINAL CHEMISTRY) BY P.RAVI SANKAR. [INTRODUCTION,STRUCTURES OF TOCOPHEROLS,CHEMISTRY OF VITAMIN E,RECOMMENDED DAILY INTAKE,DIETARY SOURCES ANS SUPPLEMENTS, PHYSIOLOGICAL ROLE RO IMPORTANCE,USES OF VITAMIN E, SIDE EFFECTS/ADVERSE EFFECTS, V

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VITAMIN E (MEDICINAL CHEMISTRY) BY P.RAVI SANKAR. [INTRODUCTION,STRUCTURES OF TOCOPHEROLS,CHEMISTRY OF VITAMIN E,RECOMMENDED DAILY INTAKE,DIETARY SOURCES ANS SUPPLEMENTS, PHYSIOLOGICAL ROLE RO IMPORTANCE,USES OF VITAMIN E, SIDE EFFECTS/ADVERSE EFFECTS, V

VITAMIN E (MEDICINAL CHEMISTRY) BY P.RAVI SANKAR. [INTRODUCTION,STRUCTURES OF TOCOPHEROLS,CHEMISTRY OF VITAMIN E,RECOMMENDED DAILY INTAKE,DIETARY SOURCES ANS SUPPLEMENTS, PHYSIOLOGICAL ROLE RO IMPORTANCE,USES OF VITAMIN E, SIDE EFFECTS/ADVERSE EFFECTS, VITAMIN E PREPARATIONS

VITAMIN E (MEDICINAL CHEMISTRY) BY P.RAVI SANKAR. [INTRODUCTION,STRUCTURES OF TOCOPHEROLS,CHEMISTRY OF VITAMIN E,RECOMMENDED DAILY INTAKE,DIETARY SOURCES ANS SUPPLEMENTS, PHYSIOLOGICAL ROLE RO IMPORTANCE,USES OF VITAMIN E, SIDE EFFECTS/ADVERSE EFFECTS, VITAMIN E PREPARATIONS

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VITAMIN E (MEDICINAL CHEMISTRY) BY P.RAVI SANKAR. [INTRODUCTION,STRUCTURES OF TOCOPHEROLS,CHEMISTRY OF VITAMIN E,RECOMMENDED DAILY INTAKE,DIETARY SOURCES ANS SUPPLEMENTS, PHYSIOLOGICAL ROLE RO IMPORTANCE,USES OF VITAMIN E, SIDE EFFECTS/ADVERSE EFFECTS, V

  1. 1. (tocopherols) VITAMIN Prof. Ravisankar Vignan Pharmacy college Valdlamudi Guntur Dist. Andhra Pradesh India. banuman35@gmail.com 00919059994000
  2. 2.  In the year 1922,Herbert M.Evans reported the existence of vitaminE. 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 because the word …. 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. . The vitamin E represents a group of eight compounds which are collectively called tocopherols. Out of 8, α-tocopherol is most active.β andγ- tocopherols possess half the activity of the α-isomer. the tocopherols (4-forms and tocotrienols 4-forms Both structures are similar except the tocotrienol structure has double bonds on the isoprenoid units. There are many derivatives of these structures due to the different substituents
  3. 3. TOCOPHEROL TOCOTRIENOL 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-tocotrienol (occurs wheat germ oil) (occurs wheat germ oil) (cotton seed oil) 1 2 3 4 5 6 7 8 11 21 31 41 51 61 71 81 91 101 111 121 Tocopherols are 6-Hydroxy chroman Isoprenoid side chain at C2 The difering factor between tocopherols is the substitutions On c5,c7,and c8 (3 W)
  4. 4.  CHEMISTRY OF VITAMIN E (TOCOPHEROLS)  Vitamin E refers to a family of eight molecules having a chromanol ring (chroman ring with an alcoholic hydroxyl group) and a 12-carbon aliphatic side chain containing two methyl groups in the middle and two more methyl groups at the end.  For the four tocopherols the side chain is saturated, whereas for the four tocotrienols the side chain contains three double-bonds, all of which adjoin a methyl group.  The four tocopherols and the four tocotrienols have an alpha, beta, gamma and delta form — named on the basis of the number and position of the methyl groups on the chromanol ring.  The alpha form has three methyl groups, the beta & gamma forms have two methyl groups and the delta for has only one methyl group. 12 2 Middle methyl groups 2 methyl groups At the end6 12 Carbon side chain
  5. 5.  Tocotrienols (found in high concentrations in palm oil) are many times more potent as anti-oxidant than are tocopherols, but they are poorly assimilated by digestion, are poorly distributed to tissues in blood and are rapidly metabolized and eliminated from the body.  But tocotrienols are well- absorbed by the skin and thus are well suited for use as a Vitamin E cream.  TOCOTRIENOLS
  6. 6.  Recommended daily intake  The Food and Nutrition Board at the Institute of Medicine report the following dietary reference intakes for vitamin E.  Infants  0 to 6 months: 4 mg/day  7 to 12 months: 5 mg/day  Children  1 to 3 years: 6 mg/day  4 to 8 years: 7 mg/day  9 to 13 years: 11 mg/day  14 years and adults: 15 mg/day
  7. 7.  Dietary sources and supplements  The following foods are rich in vitamin E.  fortified cereals  seeds and seed oils, like sunflower and safflower.  nuts and nut oils, like almonds  green leafy vegetables, like spinach, turnip.  tomato products  pumpkin  sweet potato  blue crab  rockfish  mangoes  asparagus  broccoli  papayas The Avocado - Rich in Vitamin E Hight amount found In livers of hourse And cattle. Small amounts Found in the muscles Of heart,kidney, Placenta,egg etc,.
  8. 8. Wheat germ oil. Sunflower seeds, cooked spinach, almonds, safflower oil,cottonseed oil,soybean. and hazelnuts. 1 Tbsp. wheat germ oil = 20 mg 1/4 cup sunflower seeds = 12 mg 1 cup cooked spinach = 7 mg 1 ounce almonds (23 nuts) = 7 mg 1 Tbsp. safflower oil = 5 mg 1 ounce hazelnuts (21 nuts) = 4 mg mustard greens, turnip greens, chard, sunflower seeds, almonds,,, parsley, kale, papaya, olives, bell pepper, brussel sprouts, kiwifruit, tomato, blueberries, and broccoli. Vitamin E can be found in foods such as cooking oil, fish oil, multi-grain cereal, apricots, pumpkins, mustard and poutry,olives.
  9. 9.  You can get vitamin E from 4 main groups:  Vegetable oils. Corn, canola, sunflower, sesame, cottonseed, peanut, rice bran, and palm oils.  Nuts - almonds, walnuts, peanuts, pistachios and hazelnuts.  Oil seeds, legumes and grains. Corn, lentils, wheat, rice, northern beans, chickpeas,Barley grass and oats.  Wheat germ oil Extracted from the germ of wheat, Wheat germ oil has been used since the '20s as a vitamin E supplement. It offers a good combination of tocopherols plus tocotrienols. . Wheat germ oil is great sources of natural vitamin E.
  10. 10.  Uses of vitamin E  Vitamin E is also particularly vital in treating many skin problems and diseases such as psoriasis.  As for the treatment of scars, although many people have experienced and claimed that vitamin E lotions help soften the appearance of acne and surgical scars  . They have nevertheless, help preventing skin damage and cancer due to its sun protection quality and its powerful antioxidant properties.  There was a 40% reduced risk of coronary artery disease for those who took vitamin E supplements compared to those who did not.  Many types of cancer are believed to result from oxidative damage to DNA caused by free radicals. Antioxidants - such as vitamin E - help protect against the damaging effects of free radicals, which may contribute to the development of chronic diseases such as cancer. Vitamin E also may block the formation of nitrosamines, which are carcinogens formed in the stomach from nitrites consumed in the diet. Vitamin E may also protect against the development of cancers by enhancing immune function.
  11. 11.  Prostate cancer: some evidence associates higher intake of vitamin E with a decreased incidence of prostate cancer.  The study showed that pre-menopausal women with a family history of breast cancer who consumed the highest quantity of vitamin E enjoyed a 43% reduction in breast cancer  A potent antioxidant, Vitamin E is useful for a range of topical applications, including treating burns,  reducing wrinkles,  healing irritations,  and protecting against sun damage.  Many physicians, surgeons, and wound technicians use and recommend vitamin E to help reduce scarring from surgery or injury.  Vitamin E is also a popular treatment for post-pregnancy stretch marks, which is supported by a number of studies.  The formation of amyloid plaques in the brain is one of the hallmarks of Alzheimer's disease.
  12. 12. vitamin E can help prevent chronic age-related illnesses, including heart disease and Alzheimer’s.  Vitamin E supports many of the body’s daily functions such as protecting red blood cells and maintaining the immune system.  It may also safeguard skin from harmful ultraviolet rays.  Vitamin E, an antioxidant that protects the skin from free radicals. The top layer (epidermis) protecting the skin from harsh weather and reducing the dryness that causes ashy skin. Vitamin E brings a lot of health benefits for the body and is particularly important especially for our skins, hearts, muscles and red blood cells.  In addition, Vitamin E also protects our cell membranes as well as keeping our blood circulations and nerves healthy.  In actual, one of the major benefits of Vitamin E is protecting Vitamin A from the damage of free radicals which are substances that are known to damage body cells and cause cancer.  Vitamin E works to defends the body against tissue damage. As it also protects the body’s red blood cells, it can ward of the possible development of anemia.  Other benefits of Vitamin E include helping to control blood pressure and lowering blood sugar.
  13. 13. 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.
  14. 14.  Genarally the free radicals attack the cell membrane, proteins, and DNA causing severe health problums such as cancer and cardivascular diseases. Vitamin E readily reacts with these free radicals and transforms them into less reactive and non harmful forms. Vitamin E providers the stability and intergrity of cellular membranes and imparts protection from various pulmonary diseases, cardiovascular diseases,neuronal diseases,dermal diseases and other chronic diseases. vitamin E aids in proper blood clotting and skeletal and cardiac muscles. It also useful in ---- Regulating cellular metabolism in the body including protein synthesis muscles. Provides vitamin C form oxidation. production of red blood cells. Stabilization of fats and amino acids. Metabolism of nucleic aids and steroids.
  15. 15.  The Importance Of Vitamin E  Vitamin E is also important to the health of our skins and nails.  . When Vitamin E is added to skin lotions, it carries the effect of anti- aging to the skin. It can reduce the appearance of lines and wrinkles thereby making the skin looks younger.  Vitamin E is also particularly vital in treating many skin problems and diseases such as psoriasis.  As for the treatment of scars, although many people have experienced and claimed that vitamin E lotions help soften the appearance of acne and surgical scars, recent research studies have shown otherwise.  In fact, They have nevertheless, help preventing skin damage and cancer due to its sun protection quality and its powerful antioxidant properties.  vitamin E supports a healthy circulatory and cardiovascular system, aids in proper blood clotting, improves wound healing, is necessary for tissue repair, promotes healthy hair and skin and can in effect slow the aging process.  As the "master antioxidant," vitamin E fights the harmful free radicals which increase the risk of chronic disease and accelerate aging. It is an essential component of every wellness and anti-aging program
  16. 16.  Rich in vitamin E, can help the protect your brain from Alzheimer’s, according to a new study.  a role in immune function  DNA repair,  the formation of red blood cells  and vitamin K absorption.  Getting rid of black heads.  Getting rid of acne.  Getting Rid of Dandruff.  Getting rid of stretch marks.  Vitamin E keeps your skin smooth.  Vitamin E is used as a component of multivitamin preparation.  Vitamin E helpful in the prevention of caronary heart disease by limiting the oxidation of LDL cholesterol (bad cholesterol)  Development of age related muscular degenaration (AMD)  Vitamin E is helpful in protecting the retina from glaucomatous damage.  Vitmin E +Vitamin C = is used as a prophylactic in Alzeimer’s disease.  Genarally tocopherols are widely used in cosmetic and food industry as an inexpensive preservative.
  17. 17.  Vitamin E is a powerful anti-aging agent because it could reverse age- related declines in immune function. Here is the list of conditions and diseases that Vitamin E can help in: Heart disease, angina, cancer, multiple sclerosis, diabetes, Alzheimer’s disease, cataracts, emphysema, high cholesterol, fibrocystic breast condition intermittent claudication, infertility, impotence, genital herpes, bedsores, leg cramps, muscle soreness, phlebitis, menopausal discomforts, HIV, osteoarthritis, and chronic inflammatory diseases such as lupus and rheumatoid arthritis.  Regarding sex, Vitamin E plays an important role in the production of sex hormones. It protects them from oxidation and degradation. Low vitamin E levels can cause a decline in the formation of key sex hormones and enzymes responsible for sperm production and ovarian health.  Vitamin E also shows a protective effect on sperm cell membranes. Supplementation with Vitamin E can also aid in improving sperm motility.
  18. 18.  The decline in sexual libido for women can sometimes be attributed to the drop in levels of the sex hormones estrogen and progesterone. Several studies have shown that Vitamin E possesses estrogenic, androgenic and progesterone-like properties which can help in combating this hormonal change. Thus, this vitamin can assist in easing hormonal imbalances, hot flashes, low libido and even combating vaginal changes. Regarding sex, Vitamin E plays an important role in the production of sex hormones. It protects them from oxidation and degradation .  Vitamin E, long thought of as the “sex vitamin,” is also an antioxidant. When erect, the penis is engorged with blood that carries vital oxygen. Vitamin E protects this oxygen-rich blood from becoming filled with free radicals, in addition to helping the heart during sex. Since it is almost impossible to get enough vitamin E from food, Gittleman advises supplementing at least 400 IU each day, as well as eating such foods as wheat germ, nuts, seeds and flaxseed oil.  . These free-radical fighters, (antioxidants) which include vitamins A, C and E, help protect and promote your sexual organs by reversing a low sex drive.
  19. 19.  What is the difference between natural vitaminE and synthetic vitamin E?  Regarding the right form of Vitamin E to take, researchers said that Natural Vitamin E (d-alpha tocopherol) is better than the synthetic ones (dl-alpha tocopherol) because they are known to be retained in our body two times better than the latter  In one word, the difference is: availability. Natural vitamin E has roughly twice the availability of synthetic vitamin E.  Here is the difference: The d-alpha-tocopherol in our food, the natural form, is a single entity, in other words all the molecules are identical. By contrast, the synthetic dl-alpha-tocopherol is a mixture of 8 different molecular entities, known in the chemical jargon as "stereoisomers". Of these 8, only 1 is identical to the natural form. The other 7 do not exist in nature.  Synthetic dl-alpha-tocopherol is not harmful. But its value to your body is only 1/2 of the natural.  Read the label - it's the only way to tell if you are getting natural or synthetic. Natural will say "d-alpha-tocopherol", synthetic will say "dl- alpha-tocopherol.
  20. 20.  Researchers are fairly certain that oxidative modification of LDL- cholesterol ("bad" cholesterol) promotes blockages in coronary arteries which may lead to atherosclerosis and heart attacks.  Vitamin E may help prevent or delay coronary heart disease by limiting the oxidation of LDL-cholesterol
  21. 21. 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.
  22. 22. Physico-chemical properties of vitamin E  Colour : pale yellow  State: oil  Solubility: soluble in fats and organic solvents. hence it is stored in the adipose tissue of the body. stability : It is thermostable and chemostable compound. Hence acids and basis by the process of hydrogenation or high temparature up to 1800 C. Long exposure to UV- Radiation and oxidising agents can distroy vitamin E.
  23. 23. Vitamin E preparations Vitamin E preparations are are available in single form(alpha tocopherol) or with one or more other additivies.  Commercially available vitamin E preparations(vitamin E range of 95% to 100% of the labelled amount.  Evion(merck) ------ 200mg,400mg,600mg soft gelatin capsules.  E-cap ------- 200mg,400mg capsules.  Edge --------400 IU of gelatin capsules.  Tocofer----- 200mg,400mg capsules.  Monovitin--- 100 IU,200 IU,400 IU capsules.

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