Chng 13VITAMIN V MT S CHT DINH DNGVitaminCc cht dinh dng (t hc)

ThS. on Thanh Hiu BM Ha dc H Y Dc Thi Nguyn

MC TIU HC TPNu c nh ngha, vai tr sinh hc ca vitamin, tnh cht chung ca mi nhm vitamin.Trnh by c ngun cung cp, tn gc, ch phm dc dng, hot tnh sinh hc, ch nh ca mi vitamin.Gii thch c cc tnh cht l ha (ng dng trong pha ch, nh tnh, nh lng) da vo cu trc ha hc ca mi vitamin.

VITAMINi cngVitamin tan trong ncVitamin tan trong du

1. I CNGnh ngha vitaminNgun cung cp vitaminNhu cu hng ngy v vitaminVai tr sinh hc ca vitamin

nh ngha vitaminL nhng hp cht hu c c cu trc khc nhauHu ht c th ngi v ng vt khng t tng hp cC th cn vi lng rt nh so vi khu phn n hng ngy duy tr cc qu trnh chuyn ha m bo s sinh trng v hot ng bnh thng ca c th

Vitamine = vita + amineVita = s sngAmine: hp cht c cha amin (N)Nhiu cht khng cha amin vitamin

Cu trc ha hc ca vitaminHp cht hu c, c cha nit (amincc vitamin nhm B, H) hoc khngThiamin hydroclorid (B1)Riboflavin (B2)Ergocalciferol (D2)Acid ascorbic (C)

Ngun cung cp vitaminThc vt: xem ti liung vt: xem ti liuT tng hp: vitamin D, PP, C

Nhu cu hng ngy v vitaminNhu cu hng ngy v vitamin khi b sung di dng thuc (theo US-RDA ca US-FDA)

Vitamin (n v)< 4 tui> 4 tui, ngi lnPNCT, CCBB1 (mg)0,71,51,7B12 (mg)368C (mg)406060E (IU)103030A (IU)250050008000

Vai tr sinh hc ca vitaminKhng sinh nng lng, khng l thnh phn cu trc ca c thDuy tr s bn vng ca cu trc m:A: duy tr s bn vng ca cc biu mC: tham gia tng hp colagen, cc proteoglycan v cc hp phn hu c trong t chc xng, rng, mng trong mao mch

Vai tr sinh hc ca vitaminDuy tr hot ng chc nng ca cc c quanA: tng cng s nhy cm vi nh sng yu ca vng mc mtB1: tng dn truyn thn kinhL coenzym tham gia cc chu trnh chuyn ha, trao i chtB1: coenzym tham gia chuyn ha glucid, acid aminB3: coenzym tham gia chuyn ha lipid, acid amin

Vai tr sinh hc ca vitaminThiu vitamin bnh:B1: mt mi, chn n, au vim a dy thn kinh (Beri-beri)A: sng ha biu b da, nim mc, kh mt, qung g,Nguyn nhn gy thiu: xem ti liuTha vitamin (tan trong du) bnh;A: vim da trc vy, lon th, D: v c ha t chc xng

2. VITAMIN TAN TRONG NCc im chungCc dc cht

2.1. c im chungTan tt trong nc (tr B2)Hp thu trc tip qua thnh rut vo mu, khng cn cht nh haKhi tha c lc qua cu thn v thi tr qua nc tiu khng tch ly t gy cKhng bn vi nhit, m, nh sng, oxy khng kh, tc nhn acid, kim,.. d xy ra tnh trng thiu, nn b sung hng ngy di dng thuc

2.2. Cc vitamin tan trong nc

Tn thng giTn gc Tn thng giTn gcB1ThiaminB2RiboflavinB3 (PP)Niacin (acid nicotinic, nicotinamid)B5Acid pantothenicB6Pyridoxin (pyridoxol, pyridoxal, pyridoxamin)B9Acid folicB12Cyanocobalamin, hydroxocobalaminCAcid ascorbic

Thiamin (vitamin B1) Ngun thin nhin: cm go, men bia, u tng, hoa qu, tht, gan, trng, sa, Ch phm dc dng: thiamin hydroclorid, thiamin nitrat.Tn KH: 3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methylthiazoli chlorid hydrochlorid (nitrat).NO3-

Thiamin (vitamin B1)Cu trc ha hc: c nhng nhm chc no?Cc tnh cht vt l, ha hc? ng dng trong pha ch, nh tnh, nh lng, bo qun?NO3-

Thiamin (vitamin B1)Dn xut pyrimidin tnh base yu:=> Dng dc dng monohydroclorid, nitrat tan/ ncTo ta vi TT chung ca alcaloid TTo ta vi acid silicovolframic L (PP cn) => L bng o acid MT khan (2 TM :1 HClO4)NO3-

Thiamin (vitamin B1)N4/ thiazoli km bn, d b thy phn m vng (thun nghch, km oxy ha) pH kim, trung tnh:Dng dc dng monohydroclorid, nitrat DD nc c pH acid bn hnK3[Fe(CN)6]/OH- thiocrom (mu vng, hunh quang xanh/ UV) T, L (PP o hunh quang)Bo qun trnh MT kimNO3-

Thiamin (vitamin B1)2 d vng thm:=> Hp th UV T, L2-hydroxyethyl:=> Ether ha hoc ester ha thiamin pyrophosphat coenzym/ chuyn ha glucidNO3-

Thiamin (vitamin B1)Acid kt hp:Cl- + AgNO3 TNO3- + FeSO4/H2SO4[Fe(NO)2]SO4 mu nuC phn t:=> o ph IR, nhit nng chyNO3-

Thiamin (vitamin B1)Hot tnh sinh hc:L coenzym tham gia chuyn ha glucid (di dng thiamin pyrophosphat tham gia chu trnh Krebs v con ng pentose phosphat)Tng dn truyn thn kinhThiu l lot, t ph (Beri-beri), vim a dy thn kinh (t tay chn, yu c), trm cm, gim tr nh,

Thiamin (vitamin B1)Ch nh:iu tr bnh vim a dy thn kinh, bnh Beri-beriB sung khi c th thiu vitamin B1 (ph n c thai, lao ng nng, ang dng thuc khng sinh,..)Dng bo ch:Vin nn 5mg 500mgDung dch tim 100 mg/mlCc dng phi hp (vi B6, B12,)

Riboflavin (vitamin B2) Ngun TN: sa, trng, pho mt, rau xanh, gan, thn, ng cc, bnh m, men bia,..Ch phm DD: riboflavin (lactoflavin), riboflavin natri phosphatTn KH: 7,8-Dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridin-2,4(3H,10H)-dion

Riboflavin (vitamin B2)Cu trc ha hc: c nhng nhm chc no?Cc tnh cht vt l, ha hc? ng dng trong pha ch, nh tnh, nh lng, bo qun?

Riboflavin (vitamin B2)Ribose Benzopteridin-2,4-dionC phn t

Tnh cht do ribose/vit.B2Poly alcol (-OH):P mu vi H2SO4To ester vi acid a chc mui Na tan/H2O3C*:2S,3S,4R)[a]D20=-110 n-1300

Tnh cht do benzopteridin-2,4-dionH dy ni i lun phin di:bt mu vng, DD hunh quang xanh-vngHp th tt UV-VISD b kh ha (thun nghch):To leucoflavin khng muXc tc cc P oxy ha kh/ c thAmid -NH-CO-

Tnh cht ca c phn t o t0nc, T, th TK bng SKLMRiboflavin:Khng tan trong CHCl3Mu vngHunh quang xanh-vng

Lumiflavin:Tan trong CHCl3Mu vngHunh quangOH-, ASLumicrom:Tan trong CHCl3Mu vngKhng hunh quangH+, TT, ASKhng c hot tnh

Sn phm phn hy bi nh sngLumiflavin LumicromRIBOFLAVIN

Riboflavin (vitamin B2)Hot tnh sinh hc:L coenzym tham gia xc tc oxy ha chuyn ha glucid, acid amin (di dng riboflavin phosphat)Cn thit cho hot ha pyridoxin (B6), tng hp niacin (PP), duy tr s nguyn vn ca hng cuThiu au hng, vim gc ming, vim li, vim da tit b nhn, thiu mu, c th thy tinh,

Riboflavin (vitamin B2)Ch nh:Phng v iu tr bnh do thiu riboflavinDng bo ch:Vin nn 5mg 150mgDung dch tim 0,1%; dung dch nh mt 0,1%; 0,01% (riboflavin natri phosphat)Cc dng thuc phi hp (vi cc vitamin nhm B, C)

Pyridoxin (vitamin B6)

R=Tn-CH2OHPyridoxol-CHOPyridoxal-CH2NH2Pyridoxamin

S chuyn ha cc vitamin B6

Pyridoxin hydrocloridOH-phenol:Tnh acidTnh khPhn ng th vo C6Nhn pyridin: tnh base, UV (+)-CH2OH(C5): ester ha pyridoxal phosphat-CH2OH (C4): to phc vi acid boric B(OH)3 phn bit vi pyridoxal, pyridoxamin

Cobalamin (vitamin B12)CN-:Cyanocobalamin.Nu thay CN- bng OH hydroxocobalaminH dy ni i lun phin di:Mu ti.UV-VIS (+) vi 3 lmax

Acid ascorbic (vitamin C)Tnh acid(pKa,4=4,2)UV (+)Tnh kh mnh - D b oxy ha (thun nghch hoc bt TN)

Cc ch phm dc dng ca vitamin CNatri ascorbatAscorbyl palmitat

3. VITAMIN TAN TRONG DUc im chungCc dc cht

3.1. c im chungTan trong du, khng tan trong nc Hp thu cng lipid, cn acid mt lm cht nh haKhi tha khng c thi tr ht qua thn tch ly gan, m m gy cTng i bn vi nhit. Khng bn di tc dng ca nh sng t xy ra tnh trng thiu, khng cn b sung hng ngy di dng thuc

3.2. Cc vitamin tan trong du

Tn thng giTn gc ARetinolD (D2 D7)Ergocalciferol (D2)Cholecalciferol (D3)

ETocoferol (D- hoc DL-)K (K1-K7)Menadion (K3)Phytomenadion (K1)

Vitamin A v cc cht lin quanVitamin A = cc hp cht c hot tnh sinh hc tng t retinolVitamin A1 = all-trans-retinolVitamin A2 = (all-trans)-3-dehydroretinolCc retinoid = retinol v cc dn cht, cc cht chuyn ha nh retinal, cc acid retinoic (tretinoin, isotretinoin, etretinat), b-carotenb-Caroten = tin vitamin A

Vitamin A v cc cht lin quanAll-trans-retinol (vitamin A1)All-trans-3-dehydro-retinol (vitamin A2)-CHO: retinal

Vitamin A v cc cht lin quanTretinoinb-caroten

Vitamin A dc dng

R-TnR-Tn-HRetinol-CO-CH3Retinol acetat-CO-C2H5Retinol propionat-CO-C15H13Retinol palmitat

Tnh cht l - ha ca retinol

Tnh cht l - ha ca retinolDo h dy ni i lun phin di kt thc bng OH-alcol quyt nh:Tinh th mu vng, tan trong duHp th UV-VISD b oxy haTo anhydro vitamin A mt hot tnhD b ester haTo sn phm c mu vi HClO4, SbCl3 (mu xanh)

Hot tnh sinh hc ca vitamin ATng cng s nhy cm vi nh sng yu ca vng mc mtCn thit cho s pht trin v phn chia t bo cc t chc biu mCn thit cho s pht trin ca xng, s sinh sn, s pht trin ca bo thaiThiu Tha

Hot tnh sinh hc ca vitamin AThiu qung g, kh, lot gic mc, kt mc; tng sng ha; tng p lc no ty, trn dch no; tr em d mc bnh nhim trng, si, bnh ng h hp, tiu chy,...Tha tng p lc ni s, chng mt, chng nhn i; tr em b li thp, co git, vim da trc vy.(tha caroten vng da)

Hot tnh sinh hc ca vitamin ATng cng s nhy cm vi nh sng yu ca vng mc mtCn thit cho s pht trin v phn chia t bo cc t chc biu mCn thit cho s pht trin ca xng, s sinh sn, s pht trin ca bo thaiTng chc nng min dch, ngn nga ung th.Thiu Tha

Ch nh chungPhng v iu tr cc bnh do thiu vitamin A nh

Cc retinoic acid: iu tr trng c, vy nn

Vitamin ETocol (tocoferol)Tocotrienol

Cc tocoferolTocol (tocoferol)

TocoferolR5R7R8 a--CH3-CH3-CH3b--CH3-H-CH3g--H-CH3-CH3d--H-H-CH3

Cc tocotrienolTocotrienol

TocoferolR5R7R8 a--CH3-CH3-CH3b--CH3-H-CH3g--H-CH3-CH3d--H-H-CH3

Tnh cht ca tocoferol-OH phenol:Tnh kh mnhTnh acidP th (R5/R7=-H)Nhn croman:UV (+)3C*:(D), (DL)

Tnh cht ca OH phenolD b oxy ha bo qun.Dng dc dng ester bn hn vi tc nhn oxy ha dng lm cht chng oxy ha (cho vit. A,)Phn ng mu vi HNO3 hoc Fe3+ v hp cht cha NL = PP o ceriP th - to phm mu azo

Alpha-tocoferol (vitamin E)All-rac-alpha-tocoferolRRR-alpha-tocoferol

Vitamin E dc dng(dl)-alpha-tocoferol(d)-alpha-tocoferol(dl)-alpha-tocoferyl acetat(d)-alpha-tocoferyl acetat(dl)-alpha-tocoferyl hydrogen succinat(d)-alpha-tocoferyl hydrogen succinat

Hot tnh sinh hc ca vitamin ECht chng oxy ha: bo v s bn vng ca mng t bo, hng cu (do phn ng vi cc gc t do, bo v cc acid bo cha bo ha nhiu dy ni i)Cn thit cho chc nng sinh sn Thiu chy mu tan huyt, vt thng kh lnh, x va ng mch, ; d xy thai, v sinh; vim vng mc,..Tha tiu chy, nn, vim da tip xc,

Dng bo chVin nn, vin nang, vin nhai, dung dch ungVin nang, kem bi ngoi da

*De thi chuyen tu b1, c, d*Amin: b1,2,3,6,9,12, H (biotin)Khng c N: C,A,D,E,K*Thi b1, b2, pp, c, a, d, e***Xem pka trong GGs*Xem pka trong GGs*Xem pka trong GGs*Thc cht: no3+h2so4d no, no ket hop voi fe2+ tha fe(no)2+ mu nu tiLam trong ong nghiem nhu tai lieu vong mau nau o mat phan cachNeu lam tren mat kinh dong ho vong mau nau quanh tinh the feso4*The Krebs cycle (also called the citric acid cycle and the tricarboxylic acid cycle) is very important in extracting energy from fuel molecules. TPP is the coenzyme for alpha-ketoacid dehydrogenases which catalyze two reactions of the Krebs cycle. The oxidative decarboxylation of pyruvate to acetyl CoA; The oxidative decarboxylation of alpha-ketoglutarate to succinyl CoA The pentose phosphate pathway harvests energy from fuel molecules and stores it in the form of NADPH. NADPH (reduced nicotinamide adenine dinucleotide phosphate) is an important electron donor in reductive biosynthesis. The pentose phosphate pathway also produces 5-carbon sugars such as ribose which is used in the synthesis of DNA and RNA. TPP is the coenzyme for the enzyme transketolase. Transketolase transfers a 2-carbon unit from an alpha-ketose (a sugar with a carbonyl group at position 2) to an aldose. In the reaction below a 2-carbon unit from the 5-carbon alpha-ketose xylulose 5-phosphate is transferred to the 4-carbon aldose erythrose 4-phosphate to make the 6 carbon alpha-ketose fructose 6-phosphate. Glyceraldehyde 3-phosphate results from the 3-carbon fragment that is cleaved from xylulose 5-phosphate. Note that fructose 6-phosphate and glyceraldehyde 3-phosphate (the products of the forward reaction) are an alpha-ketose and an aldose and that the reaction is reversible Neurological Function of TPPIt is evident from the neurological disorders caused by thiamine deficiency that this vitamin plays a vital role in nerve function. It is unclear, however, just what that role is. Thiamine is found in both the nerves and brain. The concentration of thiamine in the brain seems to be resistant to changes dietary concentration. Electrical or chemical (e.g., acetylcholine) stimulation of nerves results in the release of thiamine monophosphate and free thiamine into the medium with accompanying decrease of cellular thiamine pyrophosphate and thiamine triphosphate. This observation suggest that thiamine has a role in the nervous system independent of its coenzyme roles. One theory is that thiamine triphosphate is involved with nerve impulses via the Na+ and K+ gradient. | Theo Ha sinh 2, t 68 (DHDHN 2002):Bnh thiu vit B1: TPP l coE ca cc phc hp enzym kh carboxyl oxy ha pyruvat v alpha cetoglutarat, khi thiu VitB1, s thoi ha pyruvat b gim hoc ngng tr dn n ng pyr trong mu, do t bo lm vo tnh trng i nng lng ging nh trong bnh i tho ng ri lon chc nng thn, tim,,,, trao i nc.****Riboflavin = ribose + flavon (mu vng = flavonoid).Gii thch phn ng kh ha nhn 4H: do C=O ht e- hai ni i trong vng ngho e-Amid: de b TP/OH.H. toTo mui tan voi kim, to mui kt ta vi KL nng hoc KL mu*V CTHH chung cua b6Trong thuc te, ch yu dng pyridoxol HCl*V so o chuyen hoa giua cac chat qua cac enzym oxidase, phosphatase, transaminase,.*Giai thich hieu ung dien tu do OH phenol o 3 vi tri 6 phan ung the tao pham mau nito voi diazoni*Giai thich hieu ung hut e OH 4 co H linh dong*Ve CTHH va neu hoat tinh cua cac chat lien quan xem ky tai lieuChu y tretinoic acid (vitamin A acid), caroten*V cthh ca cac retinoid*Beta caroten: doi xung, cc chat khac; thay doi vi tri noi doi hoac mo 1 vong cyclohexanCaroten, crytoxanthin co nhieu trong rua qua, se chuyen hoa thanh retinal.*Mau gi*Hoat tinh d>l, trong tu nhien d, da phan lap duoc 8 chat co hoat tinh vit E . tong hop dl hoac d*All-rac=dl; rrr=d