PGS,TS.

NGUYEN PHC NHUAN

Chng VI - VITAMIN
1. I CNG 2. DANH PHAP & PHN LO I

BI GI NG SINH HA H C
PH N I SINH HA H C TNH Chng VI- VITAMIN

TP.H

CH MINH-2008

M C TIU
1. 2. nh ngha . Cong thc cau tao va chc nang sinh hoc, ac biet la vai tro tham gia trong coenzyme c a cac vitamin hoa tan trong n c (cac vitamin nhom B ). 3. Cong th c c u t o va chc nang sinh hoc cua cac vitamin hoa tan trong ch t beo : vit.A , D , E , K

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I CNG

Vitamin = vita - s s ng + amine nhm amine nh ng ch t ch a nhm amine c n cho s s ng. Sau ny pht hi n nhi u vitamin khng ch a nhm amine, nhng do thi quen nn v n s d ng t ny. Vitamin l nh ng ch t dinh d ng v cng c n thi t, khng th thi u cho m i qu trnh sinh tr ng, pht tri n c a sinh v t, nhng chng ch c n v i m t s l ng v cng nh b so v i cc ch t dinh d ng khc.
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VAI TR SINH H C Vitamin tham gia trong thnh ph n coenzyme, th c hi n ch c nng xc tc cc ph n ng sinh ha h c trong m i ho t ng s ng c a sinh v t. Ch c nng ny thu c v nhm vitamin tan trong n c (vitamin nhm B) Vitamin tr c ti p tham gia cc qu trnh trao ch t. i

2. DANH PHP V PHN LO I

C 3 cch g i tn vitamin Theo ch ci Latin (vitamin A, B, C )

Theo danh php ha h c : Vitamin A = retinol Theo tn b nh m vitamin ch ng l i : Vitamin A = retinol = vitamin ch ng b nh kh gic m c m t.
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PHN LO I
Phn lo i vitamin d a vo tnh ha tan c a chng
Vitamin
Hoa tan trong nc Hoa tan trong dau Vitamin A (retinol, -caroten) Vitamin D (cholecalciferol) Vitamin K (phylloquinone, menaquinone) Vitamin E (tocopherol) Tao mau Folic acid Vitamin B12 Loai khac Pyridoxine (vitamin B6) Pyridoxal Pyridoxamine
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2.1. CC VITAMIN HA TAN TRONG N C

Ngoai nhom B Ascorbic acid (vitamin C)

Nhom B-complex

Phong thch nang lng Thiamine (vitamin B1) Riboflavin (vitamin B2) Niacin (vitamin B3) Biotin Pantothenic acid

M ts c tnh c n lu : - Ngo i tr vitamin B12, t t c u c t ng h p th c v t. u khng - Ngo i tr vitamin B12, t t c c d tr (B12 d tr gan). - Ngo i tr vitamin C, t t c u tham gia trong thnh ph n coenzyme
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2.2. CC VITAMIN HA TAN TRONG D U

Cc c tnh chung : Cc vitamin ny l cc phn t k n c v khng phn c c, chng u c c u t o t cc n v isopren 5 C : CH2 = CH C = CH2 CH3 c h p thu cng v i ch t bo; c d tr gan (A,D,K) v m m (E); V n chuy n trong mu b ng cch k t h p v i lipoprotein; o th i theo con ng c a m t ho c theo phn. D th a m t l ng l n vitamin A, D c th gy c.
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CC VITAMIN TAN TRONG N CV COENZYME Vitamin

Thiamine (B1)

Coenzyme
Thiamine PyroPhosphate (TPP)

Enzyme
Decarboxylase kh nhm COOH c a -ketoacid Dehydrogenase p/ ng oxid ha-kh Dehydrogenase p/ ng oxid ha-kh

Riboflavin (B2) Flavin MonoNucleotide (FMN) Flavin Adenine Dinucleotide (FAD) Nicotinic acid Nicotinamide Adenine (niacin) Dinucleotide (NAD+) Nicotinamide Adenine Dinucleotide Phosphate (NADP+) Pantotenic Coenzyme A (CoA.SH) acid (B5)

Acyltransferase chuy n giao nhm 10 acyl

Vitamin
Pyridoxin (B6)

Coenzyme
Pyridoxal phosphate

Enzyme
Transaminase chuy n giao nhm amin NH2 Decarboxylase c a AA Carboxylase Chuy n giao CO2 Carbontransferase Chuy n giao nhm monocarbon (-CH3; CH4; HCOOH ..) Methyltransferase Chuy n giao nhm methyl T/G ph n ng hydroxyl ha
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CC VITAMIN TAN TRONG D U

Vitamin Vitamin A Vitamin D Vitamin E D ng h at ng Vai tr S c t th gic; nh h ng n s s/s T/gia chuy n ha Ca & P Ch t ch ng oxid ha t nhin, b o v mng t bo, nh h ng sinh s n Carboxyl ha glutamic acid c a prothrombin - y u t 12 ng mu

Biotin (H) Folic acid

Adenosine pirophosphate biotin Tetrahydrofolic acid (THF, FH4)

Retinol, Retinal, Retinoic acid 1,25-Dihydroxycholecalciferol -Tocopherol

Cobalamin (B12) Acid ascorbic (C)

Deoxyadenosylcobalamin; Methylcobalamin

Vitamin K

Hydroquinone

CC VITAMIN HA TAN TRONG N C

(1) VITAMIN B1 (THIAMINE) B n trong mi tr ng acid. C th khng d tr B1, d th a : th i theo n c ti u khng c.

Ch c nng : d ng thiamine piro phosphate (TPP) l CoE c a decarboxylase kh nhm carboxyl c a cc ketoacid, c bi t l pyruvate. i m ho t ng c a vng thiazole.
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C2
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Thi u B1 : ph thng (b nh beri-beri); nh h ng th n kinh ngo i bin, ng tiu ha v h th ng tu n hon tim. Acetyl choline Acetate + Choline vitamin B1 c s d ng trong i u tr vim th n kinh Tri u ch ng thi u vitamin B1 : bi ng n, suy nh c, i ng lo ng cho ng b i li t, hn m. Ngu n : c nhi u trong cm g o.
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NH2 C N CH 3 C N C CH CH2 + N

H C S _ O C CH 3 C CH2 CH2 O P O O O _ P O O _

Viamin B1 c ch

Hnh 6-5 : Vitamin B1, Thiaminpirophosphate

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(2) VITAMIN B2 - RIBOFLAVIN

5 10 9 1

B n v i nhi t, khng b n v i nh sng, d b oxid ha b i O2 khng kh. C mu vng do nhn isoalloxozin (d ng oxid ha). L t/p CoE c a flavoprotein (FP) : FMN & FAD, v n chuy n 2H. V tr ho t ng N1 v N10. B nh tch khi thi u B2 : n t l mi, khe mi ng, da trc v y, ko mng d . Ngu n : s a, gan, cc s n ph m ln men c a vi khu n y m kh.
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O H C CH 3 CH 3 C C C H C C N CH 2 HCOH HCOH HCOH CH 2 O _ O P O O N C C N C NH C O

C H3 C H3 C C

O H C C C H C N C H2 HCOH HCOH HCOH C H2 O _ O _ O P O P O C H2 H H OH O H OH O N HC N H C C O N C C N C NH C O

(3) VITAMIN PP NIACIN, NIACINAMID (B3) PP : Pellagra Preventive : ch ng vim da s n si. Thi u : l i , tiu ch y, vim d dy ( ch : l i en-black tangue). c t ng h p t tryptophan. 60 mg Trp 1 mg niacin. Kh u ph n nhi u b p, thi u th t s a d d n t i thi u vitamin PP. Ch c nng : l t/p c a 2 CoE : NAD+ v NADP+ c a dehydrogenase, v/c 2H.
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NH2
C N CH N

FMN

FAD

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O C _ O O P OCH2 O H H O OH OH NH2 N N N
O P OH N

NH2
_ O

NH2

N + H H

OCH2 O H H H

N +

H OH OH NH2 N N

N O P OH H H OH OH
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OCH2 O H H

N OCH2 O H H OH O HO P O H

H OH

NAD+

NADP+

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(4) VITAMIN B6 - PYRIDOXINE Trong t nhin t n t i

H H C OH HO H2C
(4) (3) (2) (1) (5) (6)

3 d ng.
H H C NH2
CH2OH

H C=O HOCH2OH

H C O CH2OH HO H2C

OH -CH2O P=O OH HOH3C-

CH2-NH2

OH

-CH2O P=O OH N

HO H2C

H3CN

B Pyridoxine (A), Pyridoxal (B) v Pyridoxamine (C)

N

Pyridoxal phosphate

Pyridoxamine phosphate

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 D n xu t pyridoxal phosphate l coenzyme c a aminotransferase, chuy n giao nhm amine NH2; L nhm ngo i c a decarboxylase c a cc AA : tyrosine, arginine, glutamic acid. L coenzyme c a deaminase kh nhm NH2 c a serine v threonine. Tham gia trong s bi n d ng c a Trp. T/g chuy n nhm CH3 t Met sang Ser t/h Cys.

Thi u B6 thi u mu (giai o n t ng h p heme). Tham gia bi n d ng trong m no : Glutamic acid -Amino byturic acid ki m sot ng c a t bo th n kinh - CO2
Decarboxylase (pyridoxal phosphate)

ho t

Vitamin B6 nh h ng t i s tch t AA trong t bo.

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(5) PANTHOTENIC ACID (VIT.B5) L n u tin c phn l p t n m men. CoA.SH CoA.SH

Pirophosphate

C trong t t c cc m, cc h t cn nguyn v , rau xanh, VSV. Panthotenic acid = Pantoic acid + alanine CoA = Adenosine-3-P + P P + Panthotenic acid + Thioethylamine CoA.SH = acid bo lin k t v i CoA qua nhm SH, acid bo c ho t ha tham gia vo cc qu trnh chuy n ha : oxy ho ho c t ng h p.
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Adenosine-3- monophosphate R-C = O

A.pantoic -alanine

OA.panthothenic

O SH -O-C-R

Thioethylamine SH

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NH2 Adenine Pantothenic acid H CH3 Pirophosphate O

-

(6) BIOTIN (VITAMIN H)

N
9

5' CH2

N O H H
3'

SH CH2 CH2 NH C CH2 CH2 NH C C C CH2 O P O P O O O OH CH3 O O

H OH
-

1'

O O=P-O

ORibose-3'-phosphate

Coenzyme A

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C nhi u trong lng tr ng, gan, s a. Trong lng tr ng c ch t avidin lin k t ch t ch v i biotin ngn c n s h p thu chng khng n tr ng s ng. VK ng ru t cung c p ph n l n nhu c u v biotin. L CoE c a carboxylase lin k t v i ph n apoenzyme qua nhm NH2 c a Lys. Tham gia qa trnh t/h acid bo (q/t malonyl ha cc acetyl.CoA); t ng h p nhn purine N u s d ng nhi u khng sinh, sulfamide gi t ch t vi khu n c l i trong ng ru t s d n t i30 thi u biotin.

(7) VITAMIN B12 (COBANAMIN)

Nguyn t N ho t ng

BIOTIN

Phn t

CO2

NH lysine c a apoenzyme

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Trong phn t c ch a cobalt (Co), c t ng h p b i VSV, khng c trong th c v t, d tr trong gan. pH 4-7 b n v i nhi t, pH > 9 d b ph h y. L y u t ch ng b nh thi u mu. ng vai tr nh m t CoE methylcobalamide methyl ha homocysteine t o thnh Met; t/g ng phn ha L-methylmalonyl.CoA thnh succinyl.CoA B12 ho t tc peptidyl synthetase trong qa trnh t ng h p protein. 32

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(8) FOLIC ACID C trong rau xanh, ng c c nguyn h t, trong gan. Thi u acid folic d n t i thi u mu do s t ng h p DNA trong h ng c u b gi m st (th ng g p ph n mang thai, ng i nghi n r u). Khng c ho t l c enzyme, d ng c ho t tnh sinh h c l tetrahydrofolic acid (THF, FH4), tham gia v n chuy n, trao i 1C : -CH3 ; -CH2 ; -CH= ; -CHO t ng h p amino acid, g c purine, pyrimidine. Phn t folate c 2 v tr ti p nh n c bi t N5 34 v N10.

N
5

N
10
Glutamic acid

Pteroylglutamic acid = FOLIC ACID

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(9) VITANIN C (Ascorbic acid) C ng , th c v t, c t ng h p t glucose. C nhi u trong q a c mi : cam, chanh. Tham gia t ng h p collagen; Tham gia h th ng oxid ha-kh cng v i glutathion, h th ng cytochrome. Ch ng stress. O= C

CC VITAMIN HA TAN TRONG D U

O= C HO-C HO-C O H- C HO- C-H CH2OH Ascorbic acid

O=C O=C O H- C HO- C-H CH2OH Dehydroascorbic acid

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(10) VITAMIN A (Retinol) T vitamin A : ch cc h p ch t c ho t tnh sinh h c c a retinol (ngo i tr nhm carotenoid : licopen v caroten). L alcohol 20 C v i cc on v isopren. Vitamin A1- retinal; vitamin A2 3-dehydroretinal). Vit. A c trong gan, tr ng, s a. Th c vat c -carotene, l ti n vit.A, khi vo ng tiu ha chng c -carotenase phn c t t o thnh 2 p/t vit.A.
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VAI TR SINH H C
11-cis retinal + Opsin
C ng C ng AS th p AS cao

(11) VITAMIN D
Rhodopsin Vit.D2 : Ergocalciferol (th c v t) Vit.D3 : Cholecalciferol ( ng v t). D3 25 OH-D3 v 1,25 diOH-D3 : T/g chuyen hoa Ca & P, duy tr Ca huy t : tng h p thu Ca ru t, h n ch th i Ca qua th n, huy ng Ca t xng khi c n. Thi u vit.D : ci xng tr em : t o mng collagen nhng khng khong ha xng x p, m m, cong. Ng i l n : long xng, d b gy. C kh nng d tr gan v bi n d ng ch m ch p. Dng vit.D li u cao : m t ngon mi ng, bu n nn, kht, Ca huy t tng tch t Ca ng m ch, th n.

l s c t th gic, c t bo hnh que c a m t. - Retinoic acid : tc ng lm pht tri n, phn ha t/b bi u m. - Thi u vit.A : m t ngon mi ng v cc n t v gic b s ng ha; xng pht tri n ch m, khng cn b ng v i s pht tri n c a h th n kinh nh h ng h th n kinh trung ng. - Retinol, retinal nh h ng n s sinh s n : gip s c, ngn h thai con ci. sinh tinh trng con - Qa d vit.A hypervitaminosis A : da s n, ng a, sng 41 gan, tng p l c h p s .

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C H3
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CH3

C H3 C H3 H 2C H 3C

C H3
22 23

C H3

H -C -C H =C H -C H -C H H 3C C H3
8 3

C H3 C H3

H -C -C H =C H -C H -C H

(12) VITAMIN E (Tocopherol) L ch t ch ng oxy ha t nhin b o v t bo; c tc d ng i v i h th ng sinh d c : ch ng s peroxid ha cc phospholipid mng t bo, b o v cc bo quan. Thi u vit.E : - T n h i sinh s n; - nh h ng ch c nng sinh l mng t bo; - Thoi ha c (teo c), c tr ng; - Gia c m : vim no, ph no, xu t huy t.
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8 3

HO

5 6

HO

5 6

E rgo s terol C H3 C H3 H -C -C H 2 -C H 2 -C H 2 -C H H 3C CH3 CH3

8 3

E rgo c alc ife rol (V it.D 2 ) C H3 C H3 H -C -C H 2 -C H 2 -C H 2 -C H H 3C C H3 H 2C

8 3 5 6 7

HO

5 6

HO

7 - Dehydroc h ole s terol

Cho lec alc ifero l (V it. D 3)

Vitamin D2 v D3

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CH3 H3C
7 8

O
1 3

CH3

CH3

CH3

CH3

CH2-CH2-CH2-CH-CH -CH2-CH2-CH-CH -CH2-CH2-CH-CH 2 2

HO

CH3

-Tocopherol

Vitamin E bao g m 8 tocopherol t nhin, trong -tocopherol c ho t tnh cao nh t. Vit.E l ch t t c nh t trong s vitamin tan trong d u, ng i ta khng quan st th y hi n t ng ng c no v i li u 300 mg/ngy .

(13) VITAMIN K Tham gia s t ng h p prothrombin trong c ch ng mu (ch ng ch y mu, c m mu). Cc d ng vitamin K : Th c v t : phylloquinone K1 VSV ng ru t : menaquinone K2 D ng t/h p dng trong i u tr : menadione - K3. C nhi u trong b p c i, bng c i, gan, lng tr ng. S d ng li u cao, ko di s d n t i thi u mu, vng da tr em, do nh h ng c h i c a vit.E ln vch h ng c u.
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VI T BI T NG H P
O CH 3 CH 3 CH 3 CH 3 CH 2 -CH=C-(CH 2)3 -CH-(CH 2)3 -CH-(CH 2)3 -CH-CH 3 CH3 O Phylloquinone (Vit.K 1) O

M i sinh vin t lm bi t ng h p theo b ng g i sau y :

CH3 (CH 2 -CH=C-CH 2 ) 6 H CH3

CH3 O Menadione (Vit.K 3)

O Menaquinone (Vit.K 2)

Vitamin K
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HA H C V TC D NG CHNH C A CC VITAMIN
Ten Cau tao hoa hoc Coenzyme Enzyme Vai tro sinh hoc Benh do thieu vitamin - Phu thung; - Viem than kinh Cac dang che pham -Vien nen, - Thuoc chch

Vit.B1 (Thia mine, aneuri n)

Thiamin pirophosphate (TPP)

Decarbo xylase cua ketoacid

-Trao oi nang lng; - Chong benh te phu

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