vitamins and its chemistry

Physiological Function of Vitamins and their chemistry
vitamin A and b complex, vitamin C, E, and cyanocobalamin

1. VITAMINS P resented By :- Subham Kumar Vishwakarma M.Pharma-I Pharmaceutical Chemistry SUBJECT- CHEMISTRY OF NATURAL PRODUCT

2. V itamin Any of a group of organic compounds which are essential for normal growth and nutrition and are required in small quantities in the diet because they cannot be synthesized by the body. 2

3. Physiological Function of Vitamins They build up the resistance of the body against diseases. Prevent and cure various diseases caused by deficiency. Help the digestion and utilization of mineral salts and Carbohydrates in the body. Stimulate and give strength to digestive and nervous system. Help health protection. Help maintenance of proper health and normal growth.

4. Chemistry and physiological significance of vitamins 3

5. Vitamin A (Retinol) Vitamin A, a fat soluble vitamin. Vitamin involved in immune function, vision, reproduction. Vitamin A & C both are important for the immune system. Vitamin A is a pale yellow primary alcohol derived from carotene. It include Retinol (alcoholic form)- One of the most active usable form , Retinal (aldehyde form) and Retinoic acid ( acidic form) 4

6. Vision- Generates pigments for the retina Maintains surface lining of eyes Bone growth Reproduction Cell division and differentiation Healthy Skin Regulate Immune System Found in animal and plant sources Animal Sources – Eggs Meat Cheese Milk Liver Kidney Cod Halibut fish oil Plant Sources – Carrots Sweet Potatoes Pink Grapefruit Apricots Broccoli Spinach Pumpkin

7. Chemistry of vitamin A 5 Vitamin A (Retinol) is a cyclic polyene alcohol which resembles the structure of Diterpenoid. The structre of vitamin A constitu te of a β- ionone ring. Vitamin A consist 2 isoprene unit (C10H16) four conjugated double bonds in the side chain of vitamin A. They are in trans arrangement. Synthetic retinol is a trans isomer. β- ionone ring and conjugated double bonds are essential for the biological activity of vitamin A.

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9. β –Carotene (Provitamin-A) Precursor of vit-A is β –carotene Beta carotene has 1/6 th activity of Vitamin

10. Physiological significance of vitamin A Vitamin A is best known of its role in the physiological functions of vision. Vitamin A participates in numerous other physiological functions, it ensures the normal proliferation of epithelial cells, the development of teeth and bones. Vitamin A deficiency ( VAD ) is a lack of vitamin A in blood and tissues. Vitamin A deficiency its early stages causes the so- called night blindness, a vision problem at twilight or in poor light. Vitamin A is essential for producing rhodopsin, the photosensitive substance of the retina. 7

11. The deficiency of vitamin A can cause further more dry eye, ataxia, conjunctivitis, corneal ulcers, skin lesions, disorders of the epithelia (bronchi, respiratory tracts, salivary glands), bone formation and nervous system abnormalities, and increased susceptibility to diseases. Vitamin A in overdose can lead to bone disorders, gingivitis, and finally the loss of vision. 8 Rhodopsin Trans-Retinal h ν (Light) Trans-Retinol Dehydrogenase (Activation of Rod/Cones) [Retinal + opsin(protein)] inactive Cis-Retinal Cis-Retinol Dehydrogenase isomerase Eyes In Liver

12. Vitamin B1 (Thiamin) Thiamine is one member of water-soluble Vitamin B-complex and is in the thermolabile fraction. Vitamin B1 , thiamin, or thiamine enables the body to use carbohydrates as energy. It is essential for glucose metabolism, and it plays a key role in nerve, muscle, and heart function ( antineuritic ) . Vitamin B1 is a water- soluble vitamin, as are all vitamins of the B complex. 9

13. Chemistry of V itamin B1 10

14. Thiamine or vitamin B1 named as the "thio-vitamine" ("sulfur-containing vitamin") is a water-soluble of the B complex. It is water soluble vitamin. It is anti beriberi vitamin. It has specific coenzyme Thiamine pyrophosphate (TPP) which is mostly associated with carbohydrates metabolism. Thiamine contain pyrimidine ring Thiazole ring held by methylene bridge. Thiamine is only natural compound which having thiazole ring. Alcohol group of thiamine esterified with phosphate 11

15. Physiological significance of vitamin B1 The active from of vitamin B1 in the body is thiamin pyrophosphate (TPP) which along with lipoic acid acts as a prosthetic group for carboxylases. Thiamine pyrophosphate is formed by the esterification of alcoholic group of thiamine with phosphate. TPP transferase catalyzes the transfer of pyrophosphate group from ATP to thiamine. Citric acid cycle and synthesis of acetylcholine thus affecting the neurotransmitter transmission. Transketolation reaction and decarboxylation of α- ketoglutaric acid to succinic acid. 12

16. 13 (TPP)

17. + + CO 2 15

18. Vitamin B2 (Riboflavin) Riboflavin is a V itamin B . It can be found in certain foods such as milk, meat, eggs, nuts, enriched flour, and green vegetables. Riboflavin is necessary for growth and for the production of red blood cells. Riboflavin also plays an important role in how our bodies gets energy from carbohydrates, fats, and proteins. Vitamin B2 is closely related to the yellow water-soluble pigments known as Flavines ( isoalloxazines ), and since it was first isolated from milk, Vitamin B2 is also known as Lactoflavin. 16

19. Chemistry of vitamin B2 17

20. The structure of riboflavin consists of 6,7- dimethyl- isoalloxazine ( heterocyclic three ring system – benzene and pteridine ring ) to which a sugar alcohol called ribitoyal group is attached at 9 th position. It is water soluble vitamin. It aids in the metabolism your fats, carbohydrates, protein and ketone bodies. It is also important for energy metabolism (ATP production in mitochondria ) F lavin mononucleotide ( FMN) and F lavin adenine dinucleotide ( FAD) 18

21. physiological significance of vitamin B2 Riboflavin is the component of two flavin enzymes The flavin mononucleotide (FMN) The flavin adenine dinucleotide (FAD) Both these flavin enzymes take part in various oxidation-reduction reactions. The oxidized flavines are yellow in colour while upon reduction ( one hydrogen atom at 1 and other at 10 positions acquisition occurs) and they become colourless. 19

22. The reaction can also proceed in the revers e direction. Hydrogen addition occurs in 2 steps - 20

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25. Both the coenzymes function with a group of proteins known as the flavoproteins. These flavoproteins due to their diverse nature can act as oxidases, dehydrogenases, hydroxylases ,oxidative decorboxylases. Riboflavin or vitamin B2 is an essential nutrient in human nutrition and plays a key role in the production of energy. Vitamin B2 is needed to process amino acids and fats, activate and folic acid, and help convert carbohydrates into the fuel the body runs on. Vitamin B2 is an intermediary the transfer of electrons in the cellular oxidation-reduction reactions which generate energy from protein, carbohydrate and fat. 23

26. Vitamin B12 / Cyanocobalamin Vitamin B 12 does a lot of things for your body. It helps make your DNA and your red blood cells. B 12 is the most chemically complex of all the vitamins Vitamin B 12 is the only naturally occurring organic compound which contains cobalt (35%). It is water soluble, deep red, tasteless, crystalline compound. 25

27. Chemistry of vitamin B12 26

28. There are many closely related compounds having B12 activity. All are cobalamins and contain in their molecules a portion called corrin ring which to a large extent resembles the tetrapyrrole ring structure of porphyrins. A single cobalt atom having one positive charge is present in the center of this ring. The Co atom is attached to all the four N atoms of corrin ring in the same way as Fe++ is attached to 5,6, dimethylbenzimidazole ribose which is attached to the side chain on ring IV through Phosphate and aminopropanol. The positive charge on Co atom is balanced by one of the several groups which give rise to more than one type of vitamin B12. These different types of vitamin B12 are given below along with their characteristic groups attached to the Co atom B 12 : Cyanocobalamin: It has CN. It is the commonly used form of the vitamin B12 B 12 -a : hydroxocobalamin: It has OH. It is claimed to be retained in the body B 12 -b : aquocobalamin : It has H 2 O B 12 -c: nitrocobalamin : It has NO 2 28

29. 1. Supports Energy Vitamin B12 plays a key role in how your bod creates energy . It keeps your cells fed, happy, and healthy. Wi thout it, your cells get hungry and you feel weak, tired, and like you’re dragging all the time. The nutrient releases energy into the cell and provides you with the appropriate balance you need for thinking and moving throughout your day. 2. Protects the Heart Your heart and entire cardiovascular system needs B12. One of its jobs is to remove a dangerous protein called homocysteine from the blood. If homocysteine is allowed to roam through blood, it damages your arteries leading to inflammation and heart disease. Get enough B12 and you’ll keep homocysteine levels down and your heart happy. Physiological significance of vitamin B12

30. 3. Your Bones Need It Studies have found patients with osteoporosis have higher levels of homocysteine and low levels of B12 than people with strong, healthy bones.Could B12 be a viable adjunct to future osteoporosis approache. If you suffer from osteoporosis or similar bone issues, speak to your doctor about getting your vitamin B12 levels tested. 4. Prevents Nerve Damage Your nerves have a protective covering to keep them safe from toxins and free radicals in your blood. Without these coverings, called myelin sheaths, exposed nerves get damaged and may even die. These dead nerves disrupt signals to and from the brain and may play a role in nerve-related conditions. Vitamin B12 supports the way your body 31

31. Vitamin C Vitamin C is a water soluble vitamin. The use of vitamin C in megadoses to cure everything from common cold to cancer. 33

32. Chemistry of vitamin C 34

33. Chemistry of vitamin C It is water soluble and is easily destroyed by heat, alkali and storage. In the process of cooking, 70% of vitamin C is lost. The structural formula of ascorbic acid closely resembles that of carbohydrates. It has strong reducing property. It’s a heterocyclic furan-2-one detivative. Ascorbic acid is a hexose derivative and closely resembles monosaccharide’s in structure. vitamin C exists in two forms L-ascorbic acid (reduces form) L- Dehydro ascorbic acid (oxidized form) 35

34.  oxidized form reduces form 36

35. Ascorbic acid performs numerous physiological functions in the human body: the synthesis of collagen, and neuro-transmitters the synthesis and catabolism of tyrosine the metabolism of microsome. Ascorbic acid is well known for its antioxidant activity, acting as a reducing agent to reverse oxidation in liquids. Vitamin C is a natural antihistamine. It both prevents histamine release and increases the detoxification of histamine. 38 Physiological significance of vitamin C

36. The synthesis and catabolism of tyrosine 39

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38. Vitamin E Vitamin E is a vitamin that dissolves in fat. It is found in many foods including vegetable oils, meat, poultry, eggs, fruits, vegetables, and wheat germ oil. It is also available as a supplement. 41

39. Chemistry of vitamin E 42

40. Vitamin E is the name given to a group of tocopherols and tocotrienols. About four tocopherols (vitmin E vitamers) have been identified alpha, beta, gama, delta. Alpha- tochopherols is the most active. The tochopherols are the derivatives of 6- hydroxy chromane (tocol) ring with isoprenoid (3units) side chain. The antioxidant property is due to chromane ring. There are four main forms of tocopherols. They are α- tocopherol : 5,7,8 trimethyl tocol β- tocopherol : 5,8 dimethyl tocol γ - tocopherol :7,8 dimethyl tocol δ- tocopherol : 8 methyl tocopherol α- tocopherol is most active and predominant form of vitamin E . 44

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42. 47 Tocotrienols : There are four related vitamin E compounds called α, β, γ and δ tocotrienols.

43. Physiological significance of vitamin E Vitamin E plays an important role as an antioxidant and protect the body cells from the damage caused by free radicals. These free radicals are highly reactive and distructive compounds formed as a result of oxidative deteriorational (metabolism) of polyunsaturated fats. Factors contributing for free radical genaration in the body include smoking and exposure to Uv-radiations. Tocopherols (Vitamin E) are equipped to perform a unique function. They can interrupt free radical chain reactions by capturing the free radical; this imparts to them their antioxidant properties. The free hydroxyl group on the aromatic ring is responsible for the antioxidant properties. The hydrogen from this group is donated to the free radical, resulting in a relatively stable free radical form of the vitamin. 49

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45. Vitamin B9 (Folic acid) A synthetic form of folic acid is used in dietary supplements. Folic acid the acts by helping body produce and maintain new cells . In particular, red blood cell formation is dependent upon adequate levels of this vitamin. Folic acid deficiency is a known cause of anemia in both adults and children. 51

46. Chemistry of B9 52

47. The word folic acid is derived from latin word Folium means leaf & it is also isolated from the leafy vegetable spinach. Folic acid mainly consists of three components Pteridine ring PABA (p-amino benzoic acid) ) Glutamic acid residue (1 to 7 residues) Hence it is known as Pteroyl-glutamic acid 53

48. Physiological significance of B9 Folic acid in the form of tetrahydrofolic acid is biologically active as a co-enzyme, with the following metabolic functions: Transfer of specific C1 units (methyl and formyl groups), which are important for cell growth, cell division and cell differentiation in the metabolism of proteins and of DNA and RNA. Together with vitamin B12, it converts homocysteine into methionine. 54

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51. Vitamin B3 (Niacin) Having enough niacin , or vitamin B3, in the body is important for general good health. As a treatment, higher amounts of niacin can improve cholesterol levels and lower cardiovascular risks. 57

52. Chemistry of B3 The coenzymes of Niacin (NAD+ & NADP+) can be synthesized by the essential amino acid tryptophan. The term "Niacin" is used for Nicotinic acid. The amide form of Niacin is known as niacinamide or nicotinamide. The conversion of Niacin to niacinamide takes place in the kidney, brain slices and liver slices. 58

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54. Physiological significance of B3 Vitamin B3 ( niacin ) is important for the body because it helps to: Convert food into glucose, used to produce energy. Produce macromolecules, including fatty acids and cholesterol. Niacin is a B vitamin that helps activate over 200 enzymes, the majority of which regulate the breakdown of carbohydrates, fats and proteins, which the body then uses for energy and for keeping the nervous system, digestive system, skin, hair and eyes healthy. 60

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