Chemistry and physiological significance of Vitamins

Chemistry of natural product

1. Vitamins Name: Zofina I. Patel M-pharm Sem-1 Subject: Chemistry in natural products Guided under: Mr. STEPHEN AVARVU

2. Definition of vitamin 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. Chemistry and physiological significance of vitamins 3

4. 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. 4

5. Chemistry of vitamin A 5

6. Vitamin A (Retinol) is a cyclic polyene alcohol which resembles the structure of Diterpenoid . The structre of vitamin A constiture of a β - ionone ring. 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. 6

7. 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. 7

8. Vitamin A is essential for producing rhodopsin , the photosensitive substance of the retina. The deficiency of vitamin A can cause furthermore 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 teeth. 8

9. Vitamin B1 ( Thiamin ) 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. Vitamin  B1  is a water-soluble vitamin, as are all vitamins of the B complex. 9

10. Chemistry of vitamin B1 10

11. 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. In 1936 williams and his associates determines the structure of Thiamine. Thiamine contain pyrimidine ring Thiazole ring held by methylene bridge. Thiamine is onlynatural compound which having thiazole ring. Alcohol group of thiamine esterified with phosphate and form coenzyme TPP. 11

12. 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. 12

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14. Citric acid cycle and synthesis of acetylcholine thus affecting the neurotransmitter transmission. Transketolation reaction and decarboxylation of α - ketoglutaric acid to succinic acid. 14

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16. Vitamin B2 (Riboflavin) Riboflavin is a B  vitamin . 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. 16

17. Chemistry of vitamin B2 17

18. The structure of riboflavin consists of 6,7- dimethyl - isoalloxazine ( heterocyclic three ring system ) 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 your energy metabolism 18

19. Physiological significance of vitamin B2 Riboflavin is the component of two flavin enzymes The flavin mononucleotide (FMN) The flavin adenine dinucleotide 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

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

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23. 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. 23

24. Under some conditions, vitamin B2 can act as an antioxidant. Vitamin B2 is an intermediary the transfer of electrons in the cellular oxidation-reduction reactions which generate energy from protein, carbohydrate and fat. 24

25. Vitamin B12 Vitamin B12 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 25

26. Chemistry of vitamin B12 26

27. Vitamin B12 is the only naturally occurring organic compound which contains cobalt (35%). It is water soluble, deep red, tasteless, crystalline compound with a molecular weight of 1355 and is hence stable at neutral pH but not at alkaline pH. 27

28. The salient features of the structure of Vitamin B12 are given below: 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 28

29. B12: Cyanocobalamin : It has CN. It is the commonly used form of the vitamin B12 B12-a : hydroxocobalamin : It has OH. It is claimed to be retained in the body B12-b : aquocobalamin : It has H 2 O B12-c: nitrocobalamin : It has NO 2 29

30. Physiological significance of vitamin B12 1. Supports Energy Vitamin B12 plays a key role in how your body  creates energy . It keeps your cells fed, happy, and healthy. Without 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. 30

31. 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 replenishes this protective covering. 31

32. 5. Protects Brain Health Researchers have noted  Alzheimer’s  patients have much lower levels of B12 than those of a similar age who have sharp, clear memory. In the same way B12 helps protect nerve cells, it helps protect the myelin sheaths of brain cells that are often lacking in Alzheimer’s patients. Some research suggests that cobalamin deficiency may cause a type of dementia in elderly patients that is in fact reversible with the right nutritional intervention. 6. Keeps You Looking and Feeling Young Aging happens when your cells begin to wear and tear, and they age faster when your DNA doesn’t replicate correctly. Many factors can affect DNA replication, like  free radicals , toxins in the blood, high blood sugar, and high levels of omega-6 fats in your diet. B12 supports DNA health, thereby keeping your cells younger. And when your cells are young, you look and feel young too. 32

33. 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

34. Chemistry of vitamin C 34

35. 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. 35

36. vitamin C exists in two forms L-ascorbic acid (reduces form) L- Dehydro ascorbic acid (oxidized form) oxidized form reduces form 36

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38. Physiological significance of vitamin C 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

39. T he synthesis and catabolism of tyrosine 39

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41. 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

42. Chemistry of vitamin E 42

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44. 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. 44

45. 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 . 45

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

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49. 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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51. 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

52. Chemistry of B9 52

53. 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

54. 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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57. 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

58. 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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60. 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

61. References Feeding And Nutrition Of Companion And Hobby Animals , János Tossenberger (2011) , Kaposvar University Vitamin B1 [Thiamine] Medicinal Chemistry By P. Ravisankar [ Source] Vitaminb2[riboflavin] Medicinal Chemistry,by P.Ravisankar [Sources Of Vitamin B2,chemistry Of Vitamin B2,physiological Importance,synthesis Of Riboflavin,reactions , Vitamin B2 Deficiency Symptoms,functions,uses Of Riboflavin. By Dr. Edward Group Dc, Np , Dacbn , Dcbcn , Dabfm   Published On March 19, 2015, Last Updated On April 24, 2017 Michael B. Davies, John Austin, David A. Partridge: Vitamin C- Its Chemistry And Biochemistry Dr. P. Ravisankar M. Pharm., Ph.D Ossama Motawae , Marketing Manager Https://Www.Dsm.Com/Markets/Foodandbeverages/En_us/Products/.../Vitamin-b3.Html 61

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