Chemistry of Natural Products

(CHEM-479)

Online Lectures (Vitamins-D+E+K)

Dr Abdul Rauf Raza

(Associate Professor)
Department of Chemistry
University of Sargodha, Sargodha
 Classification of Vitamin-D

1. Vitamin D1 (Ergocalciferol 1, Lamisterol 2 in 1:1)

2. Vitamin D2 (Ergocalciferol 1)
3. Vitamin D3 (Cholecalciferol 3)
4. Vitamin D4 (22-Dihydroergocalciferol 4)
5. Vitamin D5 (Sitocalciferol 4)
 Vitamin-D

H H
HO HO
Vitamin D1 (Lamisterol) 1 Vitamin D2 (Ergocalciferol) 2

22

H H
HO HO
Vitamin D3 (Cholecalciferol) 3 Vitamin D4 (22-Dihydroergocalciferol) 4

3
 Vitamin-D

H H
7
HO HO
7-Dehydro-beta-sitosterol 6 Vitamin D5 (Sitocalciferol) 5

Function
•Regulated the Ca2+ and P levels in blood
•Promotes bone formation and mineralization
•Affects immune system by promoting phagocytosis
(Anti-tumor activity)
• Deficiency causes rickets in children osteomalacia in
adults 4
 Biosynthesis of Vitamin-D3
Phytosteroids

Liver
H
Dehydrogenase
H H H H
HO 7
HO
Cholesterol 1 7-Dehydrocholesterol 2

Retro-electrocyclization
(295-297 nm)
con-rotation

H7
[1,7]-Sigmatropic shift 1
H H
HO HO 3
Vitamin D3 (Cholecalciferol) 4

5
 Mechanism of biosynthesis
Anti-clockwise

H H
con

HO HO 3
2

H 7
1

HO HO 4
3

6
 Vitamin-E

O
R

O
2
R = H, alpha-tocopherol
R = Ac, alpha-tocopheryl acetate

HO

O
2
Trocotrienol
7
 Role of Vitamin-E
•Anti-oxidant (prevents cancer)
•Prevents cataracts
•Repairs DNA

X-H
O O
X H

O R O R

Resonanace stabalized
free radical

8
 RDA of Vitamin-E

Source Amount Vit-E (mg) % RDA

1 Wheat germ oil 1 TS 20.3 135

2 Roasted almond 1 Oz 7.4 49

3 Sunflower oil 1 TS 6.0 40

4 Hazelnut/peanut oil 1 TS 6.0 40

9
 Vitamin-K
O O

3 n

O O
Vitamin-K1 (Phylloquinone) Vitamin-K2 (Menaquinone)
Produced by animals Produced by bactaeria in intestine

Vitamin-K = Koagulation (German word) = Coagulation, Precipitation

RDA = 120 microg / day

10
 Mechanism of action

X
O OX
R R

O O
Vitamin-K1 or K2 Resonanace stabalized
free radical

11