24.Vitamini 1

25
Vitamini Prof.dr Danica Agbaba

description

Farmaceutska hemija

Transcript of 24.Vitamini 1

Page 1: 24.Vitamini 1

Vitamini

Prof.dr Danica Agbaba

Page 2: 24.Vitamini 1

Vitamini

HO

H HHO

H H

hν hν

Ergosterol

Lumisterol2

HO

H

H

HO

H

HO

6

∆hν

Ergosterol

ErgokalciferolTahisterol2

Pre-ergokalciferol

Page 3: 24.Vitamini 1

Vitamini

C CH CH2

CH3

H2C

2-metil-1,4-butadien

H C CH6

Hemiterpen

H3C CH3

CH3

1

2

3

4

5

6

H3C CH3

CH3

1

2

3

4

5

6

β-jononα-jonon

2,6,6-trimetil-1-cikloheksen

C40-tetraterpen

C20-diterpen

Page 4: 24.Vitamini 1

Vitamini

CH3CH3

CH3CH3

1

23

4

5 61

2

3

4

5

6

7

8

9

10

11

12

13

14

15

16

17

18

β-karoten

Dioksigenaza

Peroksidaza

CH3CH3 O

C

CH3CH3

2

3

4

5

6

7

8

9O

H

12

CH2OH

CH3CH3

2

3

4

5

6

7

8

9

1

Retinal

dehidrogenaza

3,4-dehidroretinol-A2

Retinol

Retinal

A1

Page 5: 24.Vitamini 1

Retinol, Akseroftol

CH2OH

CH3CH3

CH3

2

3

4

5

6

7

8

9

1

H3C CH3

1'

2'

3'

4'

5'

6'

12

34

5

6 7

8

910

1112

1314

15

All-trans-A1

3,7-dimetil-9(2',6',6'-trimetil-1-cikloheksenil)-2,4,6,8-(nonatetraen)-1-ol

4-cis (Z) ili

11-cis (Z)C

CH3 O

HRetinal

COOH

CH3

Retinolna kiselina

Z-cis

Tretinoin

Page 6: 24.Vitamini 1

Etretinat

COOC2H5

CH3CH3CH3

H3C

CH3H3CO

Page 7: 24.Vitamini 1

CH3

CH3

HH

H

CH3

CH3

H3C CH3

CH3

H

H

H

5α- androstan

H

HH

5α-holestan

Page 8: 24.Vitamini 1

ProvitaminiH3C

CH3

CH3

CH3

CH3

CH3

HO

H

H

A B

C D

18

19

20

2122

2324 25

Ergosterol

(3β, 22E)-ergosta-5,7,22-trien-3-ol

UV

CH

H3C

CH3

CH3

CH3

CH3

H

H

CH2

HO 1

23

4

5

10

19

6 7

89

11

12

17

25

Ergokalciferol-D2

3β, 5Z,7E,22E

Page 9: 24.Vitamini 1

CH3

CH3

H3C

H

CH3

CH3

H

H

H

H

C27-Holestan

CH3

CH3

H3C CH3

CH3

HO

17

18

19

20

21 22

23

24

25

26

27

H

H

Holesterol

3β-holest-5-en-3-olC27-Holestan

3β-holest-5-en-3-ol

CH3

CH3

H3C CH3

CH3

HO

17

18

19

20

21 22

23

24

25

26

27

7-dehidroholesterol

Provitamin-D3

Page 10: 24.Vitamini 1

CH3

CH3

H3C CH3

CH3

HO

9

107-dehidroholesterol

UVSeco 9,10

Ergokalciferol-D2

5Z,7E-izomerHolekalciferol-D3

CH3

H3C CH3

CH3

HO

CH2

CH3

12

34

56

7

89

10

1911

12

13

14 15

1617

18 25

Page 11: 24.Vitamini 1

CH3

CH3

CH3

CH2

H3C

45

67

89

10

11

12

13

14 15

16

171825

CH3

CH3

CH3

CH2

H3C

4 5

67

89

11

12

13

14 15

16

171825

OH

HO1

23

10

5Z,7E-9,10-seko-holesta-5,7,10 (19)-trien-3β-ol

Holekalciferol-D3

HO1

23

4 510

OH

Page 12: 24.Vitamini 1

Sintetski analozi D2 i D3

CH3

H

H3C

H

OH

OH

HO

CH2

12

34

56

7

89

10

11 1213

14 15

16

17

18

19

HO6

Calcipotrien

1α-OH-D2-doksekalciferol

19-Nor-1α-25-dihidroksi D2-paricalcitol

Page 13: 24.Vitamini 1

O

1

2

3

+

OH

H

Hroman

OCH3

R

HO

2

3

45

6

7

8

*

Tokol

R=terpenski st

Page 14: 24.Vitamini 1

Vitamini E-tokoferoli

Opšta formula

R-fitil (diterpen)

CH3

OCH3

R

R

HO

R

R

*

2

3

45

6

87

1

O

HO

CH3

CH3

H3C

CH3

CH3 CH3 CH3

CH3

1

21

2

3 5 7 9 11

4 6 8 10 12*

α-Tokoferol (2R,4R,8R)

2,5,7,8-tetrametil-2-(4,8,12-trimetiltridecil)-hroman-6-ol

Page 15: 24.Vitamini 1

O CH3

R

R

HO

R

R

1

2

3

456

7

8

*

-2H

+2H

O

O CH3

OH

R

R

R

R

Hinon-inaktivan

Page 16: 24.Vitamini 1

Vitamini K

O

O

CH3

R

12

3

2' 4' 6' 8' 10' 12' 14'

15'

16'

* *R=

K1-

1' 3' 5' 7' 9' 11' 13 15'

17'CH3 CH3

H HFitil-

2'E, 7'R, 11'R

K2- n=4 (30)n=5 (35)

n

Page 17: 24.Vitamini 1

Vitamini K

Prirodni

I

II

K1-Filohinon-u zelenim delovima biljaka

K2-Menahinoni-crevna floraII

III

K2-Menahinoni-crevna flora

Sintetski

Resorpcija-pasivni transport prednost

Page 18: 24.Vitamini 1

Sintetski vitamini K

O

CH3

O

P ONa

ONa

O

K4

OCOCH3

CH3

OCOCH3

K5

PO ONa

ONa

OCOCH3

CH3

NH2..

HCl

OHNH2

CH3

NH2 2HCl

Page 19: 24.Vitamini 1

Sintetski vitamini K

O

CH3

O

CH3

OSO2Na

OO

Page 20: 24.Vitamini 1

OH

CH3

R

OH

O

CH3

R

O

O

VitaminKH Vitamin K-2,3 epoksid

Vitamin K

CO2 + O2

Protrombin

Faktor koagulacije

VII, IX, X

+ cofactor

O

CH3

R

O

VitaminKH2

2,3-hinon

reduktaza

Vitamin K

Vitamin K-2,3 epoksid

Vit K-2,3

epoksid reduktaza

Kumarini Kumarini

Page 21: 24.Vitamini 1

O O

Antikoagulansi

O O

OH

1

2

3

45

6

7

8

Kumarin=benzo-2-piron≡

2H ili 2α-Hromen

18

4-hidroksikumarin

Page 22: 24.Vitamini 1

Antikoagulansi

Dikumarol

OO

OH

CH2

OO

OH

Dikumarol

OO

OH

CH

OO

OHC

O OC2H5

Etilbiskumacetat

Page 23: 24.Vitamini 1

Monokumarini

O

C

CH3

OH

O

O

1

23

4

5

6

7

*

O

C

CH3

OH

O

O

*

NO2

O O

Varfarin Acenokumarol

O

CH3

OH

O

*

Fenprokumon

Page 24: 24.Vitamini 1

Indandioni

O

O

H

R

1

2

3

O

O

H

R

1

2

3

O

R Fenindion

R OCH3 Anisindion

Page 25: 24.Vitamini 1

R

O

O

CH3

O

CH3

H

Vit. K koagulans

O

R

O

O

H

12

3

O

O

H

R

O

Antagonisti vitamina K

R

OH

R

OH

CH3

OH

O

R

OH

O1

2

3

O

OH

R