MC LC I. NH NGHA, NGUN GC, CU TRC, PHN LOI 1.1. nh ngha 1.2. Ngun gc 1.3. Cu trc 1.4.

Phn loi 1.4.1 Eucoflavonoid 1.4.2. Isoflavonoid 1,4.3. Neoflavonoid II. TNH CHT 2.1. Eucoflavonoid 2.1.1. Flavon, Flavonol 2.1.2. Flavanon, Flavanol 2.1.3. chalcon 2.1.4. Anthocyanidin, Antocyanin 2.2. Isoflavonoid III. CC PHNG PHP NH TNH V NH LNG 3.1. nh tnh 3.2. nh lng IV. CC PHNG PHP CHIT SUT V TNG HP FLAVONOID 4.1. Chit sut 4.2. Tng hp V. VAI TR CA FLAVONOID TRONG CY 5.1. Cc phn ng sinh ho 5.2. Vai tr c ch v kch thch sinh trng 5.3. Vai tr to mu sc 5.4. Vai tr bo v cy VI. NG DNG 6.1. Tc dng sinh hc 6.2. ng dng Trong y hc

LI NI U Ngy nay, x hi cng pht trin nhu cu v cht dinh dng cng cao, mu sc trong thc phm cng c ci thin nhm tng gi tr cm quan cho thc phm. Cht mu l mt trong cc yu t quan trng nhm mc ch . Mt trong cc cht to mu tiu biu la Flavonoid, Flavonoid l mt trong cc nhm hp cht polyphenol thng gp trong thc vt. phn ln cc cht flavonoid c mu vng ( flavonoid bt ngun t flavus c ngha l mu vng). Tuy nhin, mt s c mu xanh, , tm, mt s khc khng mu nhng cng thuc flavonoid. Cc flavonoit l mt trong nhng nhm hp cht phong ph v a dng vo bc nht trong thin nhin, c mt khng nhng ch trong nhng thc vt bc cao m cn trong mt s thc vt bc thp, thm ch cn c c trong cc loi to. Hn mt na rau qu thng dng c cha flavonoit, chng cng l cc thnh phn hay gp trong dc liu c ngun gc thc vt. Cho n nay, flavonoid vn l lp cht c cc nh ho hc cc hp cht thin nhin quan tm nghin cu. C khong trn 11000 hp cht flavonoit c bit v cu trc. Flavonoid khng nhng c gi tr v mt cm quan m c khai thc, s dng trong nhiu lnh vc: Thc phm, m phm v c ngha c bit quan trng trong y dc hc. Flavonoit c ng dng trong y hc iu tr mt s bnh nh: vim nhim, d ng, lot d dy v hnh t trng, gip c th iu ho cc qu trnh chuyn ho, chng lo ho, lm bn thnh mch mu, v gim lng cholesterol trong muVi cc nh ho sinh th cho rng flavonoit l mt cht chng oxi ho l tng. Hin nay nhiu flavonoit c phn lp t thc vt c ng dng thnh cc ch phm c tr bnh v s dng trong bo qun thc phm, c th gii cng nhn l mt trong nhng lp cht thin nhin c tc dng lm chm qu trnh lo ho v t bin ca cc t bo trong c th

I.NH NGHA, NGUN GC, CU TRC, PHN LOI 1.1. nh ngha Flavonoid l mt nhm hp cht t nhin ln thng gp trong thc vt, phn ln c mu vng. V cu trc ho hc, flavonoid c khung c bn kiu C6C3C6 (2 vng benzen A v B ni vi nhau qua mt mch 3 carbon) v c chia lm nhiu nhm khc nhau, y khng gii thiu v cu to ca tng nhm. Hu ht flavonoid l cc cht phenolic. 1.2. Ngun gc Cng ging vitamin C, cc flavonoid c khm ph bi cc nh sinh ho ni ting nht ca th k XX: Albert Szent-Gyorgyi (1893 1986). ng nhn gii nobel nm 1937 vi nhng khm ph quan trng v c tnh ca vitmin C v flavonoid.

1.3. Cu trc Flavonoids l mt chui polyphenolic gm 15 nguyn t carbon v hai vng benzen lin kt bi mt ng thng c 3 carbon

Khung trn, c th c m t h thng nh C6C3C6 Cu trc ho hc ca flavonoids da trn c s l mt khung 15C vi mt Chromanne vng thm B th hai v tr 2, 3, hay 4

Flavonoid gm 2 vng thm v mt vng pyran Vng thm bn tri gi l vng A Vng thm bn phi gi l vng B Vng trung gian cha nguyn t oxy gi l vng pyran

1.4. Phn loi Flavonoid c cu trc mch C6C3C6,u c 2 vng thm. Tu thuc vo cu to ca mch C trong b khung C6C3C6, flavonoid c phn thnh cc nhm sau: + Eucoflavonoid: Flavon, flavonol, flavanon, flavanol, chalcon, antocyanin, anthocyanidin + Isoflavonoid: isolavon, isoflavanon, rotenoid + Neoflavonoid: calophylloid 1.4.1. Eucoflavonoid

Flavon (= Flav-2-en-4-on)

Flavonol (= 3-Hydroxy-4-oxoflav-2-en)

Flavon rt ph bin trong thc vt: Thng, hong cm (r), M (l).Cy anh tho, cy la apirenin v luteolin.

Flavanon (= Flavan-4-on)

Flavanol (= Flavan-3-ol)

Chalcon c ch yu mt s cy h cc Asteraceac tp trung nhiu nht v cy, g li (keo, bch n, d, u tng, trinh n hong cung, dng x) . Khng tm thy ng vt

chalcon

anthocyanin

anthocyanidin

1.4.2. Isoflavonoid

isoflavan

isoflavonoid

1.4.3. Neoflavonoid

neoflavan

Neoflavonoid

calophylloid

Phn t ca cc hp cht cc phn nhm trn u c 2 vng thm, mang nhm hyroxyl vi s lng v v tr khc nhau, tu thuc tng cht. Cc hp cht ny c cu trc mch C6C3C6 ,nhng khung cu ni C3 gia 2 nhn th khc nhau tu thuc tng loi hp cht. Mch cu ni c th l mch h (chalcon), mt vng n (flavanon), hoc vng c ni i (flavon, flavonol). 2.1.1. Flavon, Flavonol - L hp cht phn cc nn tan trong nc, t tan trong dung mi hu c - H t giy c nh dch chit trn ming l ammoniac cho mu vng sng - Acid sunfuaric nh ln cc dn cht flavon, flavonol cho mu vng m - Dung dch SbCl5/CCl4 :mu vng m 2.1.2. Flavanon, flavanol + Cc TNH CHT Flavonoid to c phc vi cc ion kim loi m chnh cc ion kim loi ny l xc tc ca nhiu phn ng oxy ho. Do tng phn nhm ca flsvonoid c cu to ring, chng va c tnh cht chung va c nhng khc bit v tnh cht vt l v ho hc. Trong thc vt cc hp cht trn thng tn ti di dng hn hp ca cc dn sut, vi t l khc nhau, tu thuc ngun gc thc vt. 2.1. Eucoflavonoiddn xut flavan-3,4-diol u khng mu, c tnh quang hot. + Flavanon, flavanol l cc cht khng mu, nhng khi tc dng vi dung dch acid v c th c mu + D b oxi ho v trng hp ho nn vic phn lp cht tinh khit gp kh khn.

2.1.3. Chalcon + Km bn trong mi trng kim + Tc dng vi dung dch FeCl3: cho kt ta xanh thm hoc xanh nht tu theo s lng nhm hydroxyl trong phn t + D tan trong nc nng, ru, to dung dch khng mu, khng tan trong cc dung mi khng phn cc hoc t phn cc nh benzen hoc Chloroform. + Di tc dng ca H+ hoc OH-, chalcon c th chuyn sang flavanon + Khi to lin kt glycosid phn ng ni vo v tr 4, mt s 2 thnh ru. 2.1.4. Anthocyanidin, antocyanin + Anthocyanidin c tnh base mnh to thnh mui bn vi acid v c. + Chng to dung dch mu trong acid v mu xanh da tri trong mi trng kim. + dng base t do, anthocyanidin l cht ng phn vi flavanon. + L dn xut ca flavon m nhm carbonyl b kh + Cc dn xut flavan-3,4-diol u khng mu, c tnh quang hot + Khng mu, nhng khi tc dng vi dung dch acid v c th c mu + D b oxi ho v trng hp ho nn vic phn lp cht tinh khit gp kh khn + Anthocyanidin thng tn ti di dng glycozit, gi l anthocyanin + Mt vi hp cht kiu anthocyanidin

OH OH HO O OH OH melacacidin OH

OH OH HO O OH OH ( ) leucorobinetinidin
2.2. Isoflavonoid (isoflavon, isoflavanon, rotenoid) Isoflavonoids tt c khng c mu sc. N c to thnh t axetat theo c ch ng vng vi phenylalamine, cinnamate dn xut c st nhp vo vng B v C2,3, v-4 ca d vng. III. CC PHNG PHP NH TNH V NH LNG 3.1. nh tnh +Flavonoid l mt nhm hp cht t nhin ln thng gp trong thc vt, phn ln c mu vng. + Cc cht thuc nhm leuco-anthocyanidin do khng c ni i lin hip gia vng B vi nhm carbonyl nn khng mu. +Cc dn xut anthocyanidin th mu thay i tu theo pH ca mi trng + Hi amoniac : Vt flavonoid cho mu vng. C th quan st nh sng thng hoc di n t ngoi (bc sng 366nm) trc v sau khi h amoniac. + Thuc th Benedic : Ho tan nng 173g natri citrat v 117g natri carbonat trong 700 ml nc, lc nu cn. Ho tan 17,3g ng II sulfat trong 100 ml nc.Trn ln 2 dung dch trn, khuy u. ngui hn hp ri thm nc va 1000 ml. Cc flanon v flavonol s cho vt mu vng trn nn l nht vi thuc th ny + St III clorid 3% trong ethanol: Tu theo s lng v v tr ca nhm OH phenol m cho mu lc, xanh hoc nu. + Thuc th acid boric acid oxalic: Gm 15 ml dung dich acid boric 10% v 5ml dung dich acid oxalic 10%.Sau khi phun sy bn mng 120 C trong 10 15 pht, cc flavon v flavonol pht quang mu lc hay vng lc. + Thuc th Diazo: Cc dn cht flavonoid c nhm OH v tr 7 c th kt hp vi mui diazoni to thnh cht mu azoic mu vng cam n . + Thuc th nhm clorid: To phc mu vi flavonoid bn mng sau khi phun dung dch AlCl3 1% trong methanol c sy 1200 C trong 5 pht, quan st vt nh sng thng hay di n t ngoi, bc sng 366nm.

OH

+ Mui ca kim loi khc: nh dung dich nc bo ho ch axetat cho mu vng vi flavon, mu cam vi flavonol. + Thuc th acid sulfuric 80%: c tc dng kh nc chuyn leucoanthocyan thnh anthocyan c mu . + Thuc th NP/PEG: Phun dung dch Difenylboryloxyethylamin 1% trong methanol, sau phun tip dung dch PEG 4000 5% trong cn soi di n UV366 nm.

3.2. nh lng Tu vo tng loi Flavonoid m ta c phng php nh lng c th khc nhau. V d: a. Flavon hoc flavonol + Phng php cn: ng dng khi nguyn liu giu c flavon hoc flavonol v dch cht t tp cht. + o mu: bng phn ng cyanidin, phn ng kt hp vi mui diazoni, to phc mu vi AlCl3, Mui titan, chrom + Phng php o ph t ngoi. b. Chalcon * Phng php phn tch HPLC (sc k lng cao p). Vi pha ng l dung dch acetonitrile v acid H3PO4 1% (phng php chun trong phn tch). * Phng php so mu: c nhiu phng php so mu khc. Phng php Folin ciocalteu: (hn hp mui phc polyphosphotungstate molydate). + Rt nhy i vi cht kh, trong mi trng kim nh th s b kh thnh sn phm phc molydenium tungsten c mu xanh. + Sau em o hp thu A (chalcon ch hp thu mch vng 300 400 nm). Phng php Prussian Blue: +Hn hp thuc th l FeCl3 v K3Fe(CN)6 b kh bi cc hp cht phenol v to thnh phc ferric (III) hexacyanoferrate (II) c mu xanh. + yn dung dch trong 15 pht, sau em o hp thu A.

 Phng php Diazotized + Da vo kh nng phn ng ghp i vi hp cht diazo trong mi trng acid to thnh hp cht c mu vng c trng. + Lc u, yn dung dch trong 1 gi, sau em o hp thu. Phng php Vanillin HCl: To thnh hp cht c mu . IV. CC PHNG PHP CHIT SUT V TNG HP FLAVONOID 4.1. Chit sut Nguyn liu c chit vi mehanol, bc hi methnol trong chn khng hay trn ni cch thu ti cn. Ho tan cn trong nc ri chit li bng ethylacetat. Bc hi dch chit ethyacetat trn cch thu ti cn. Ho tan cn trong methanol chm sc k hoc c th dng dch chit methanol ban u lm dung dch chm sc k. Khng c mt phng php chng no chit sut cc flavonoid v chng rt khc nhau v tan trong nc v trong cc dung mi hu c. VD: Vi cc cht anthocyanin thng km bn vng nht l cc acyl anthocyanin c acyl ho vi cc acid aliphatic do ngi ta thng chit bng methanol c mt ca cc acid yu nh acid acetic, acid citric, Cc dn cht flavon, flavonol c nhm OH t do v tr th 7 tan c trong dung dch kim long, da vo chit. chit cc dn cht dng glycoside, ngi ta phi loi cc cht thn du bng ether du ho sau chit bng nc nng hoc methanol hoc ethanol hay hn hp cloruafom v ethanol. Dch chit em lm m c di chn khng nhit thp (40-70 C). phn lp tng cht flavonoid, ngi ta dng phng php sc kh ct. * Cht hp ph Cht hp ph thng dng cho sc k cc flavonoid l silicagel G, bt polyamind, thng hot ho 1200 C trong 1 hoc 2 gi. Ngoi ra cn c th dng cc cht khc nh bt cenllulose, silicagel, magnesol, * Dung mi + i vi lp mng silicagel G Tch cc Aglycol : -Toluen Ethyl formiat acid formic (5:4:1) Tch flavon : - Benzen aceton (4:1), (9:1) - Benzen Ethyl acetat (3:1) - Ethyl acetat Methanol (4:1) Tch cc flavonoil:

- Ethyl acetat Methanol (8:2) - Benzen - pyridin acid fomic (36:9:5) Tch cc flavonoid glycosid: -Ethyl acetat acid fomic - nc (8:1:1) - Butanol Ethyl acetat Dimethyl formamid - Nc (10:6:3:2) - Ethyl acetat Ethyl acetat aceton acid fomic (15:2:2:1) - Clroform methanol (9:1) - Ethyl acetat Acid fomic Acid acetic khan - nc (100:11:11:27) + i vi lp mng bt polyamid Methanol - nc (8:1); (4:1) Ethanol - nc (3:2); (4:1) Ethyl acetat Methylethylceton acid formic - nc (5:3:1:1)

4.2. Tng hp

V. VAI TR CA FLAVONOID TRONG CY 5.1. Cc phn ng sinh ho + Cc nhm OH phenol ca flavonit c vai tr trong s ho tan ca cht v di chuyn d dng qua cc mng sinh l. + Mt s flavonoit c tc dng nh l cht chng oxi ho, bo v acid ascorbic trong cy. + Mt s c tc dng c ch cc enzym v cc cht c ca cy. 5.2. Vai tr c ch v kch thch sinh trng ca cy + Cc nhm OH c vai tr quyt nh vai tr c ch v kch thch sinh trng ca cy.

VD: Trong cy i cc flavonoit c cc nhm OH v tr 4 lm tng cng hot tnh ca enzim lm kch thch sinh trng, cn khi OH v tr 3 v 4 li c ch s sinh trng ca cy. + Flavonoit cn tham gia vo qu trnh h hp quang hp. 5.3. Vai tr to mu sc + To ra sc hp dn d ong bm n th phn gp phn cho cy tn ti v pht trin. + Trong vic to mu cc flavonon, flavonol, chalcon cho mu vng trong khi cc autoxyanin cho mu hng, , tm hoc xanh thm. 5.4 Vai tr bo v cy To v ng ng vt n c khng thch n cy. NG DNG Tc dng sinh hc Cc dn cht flavonoid c kh nng dp tt cc gc t do nh: HO- ROO+ Cc gc ny nu sinh ra cnh cc DNA s gy ra nhng nguy hi nh bin d, ung th, tng nhanh s lo ho. Khi a cc cht chng oxy ho nh Flavonoid vo c th bo v t bo th c th ngn nga cc nguy c x va ng mch, tai bin mch, lo ho,v kh nng chng oxy ho ca flavonoid cn mnh hn cc cht khc nh vitamin C, E, Selenium v km. Flavonoid to c phc vi cc ion kim loi nh cc phc: VI. 6.1.

M chnh cc ion kim loi ny l xc tc ca nhiu phn ng oxy ho. Tc dng chng c ca flavonoid lm gim thng tn gan, bo v c chc nng gan. Flavonoid th hin tc dng chng co tht nhng t chc c nhn (ti mt, ng dn mt, ph qun v mt s t chc khc). Trn b my tit niu, nhiu flavonoid thuc nhm flavon, flavanon, flavonol th hin tc dng thng tiu r rt. Tc dng chng lot ca flavanon v chalcon-glycoside ca r cam tho c ng dng cha au d dy.

V mt s cc tc dng khc.

6.2. ng dng trong y hc - Nhiu flavonoid c tc dng c ch h hp v s ti sinh sn i vi nhiu chng vi khun. Nhiu flavonoid c tc dng i vi mt s dng ung th (ung th vm hng) Nhiu flavonoid c tc dng nng cao tnh bn ca thnh mch mu c bit l cc flavonoid c nhm OH v tr 3,4. Rutin l cht tiu biu ca tc dng ny. Tc dng estrogen: Mt s flavonoid c tc dng gy sy thai ng vt. Nhiu flavonoit c tc dng chng d ng, chng co git, gim au . Flavonoid lm bn thnh mch, gim sc thm thu cc ng dng trong cha tr cc ri lon chc nng tnh hng cu quan thnh mch, gin hay suy yu tnh mch, tr, ri lon tun hon vng mc. Cht flavonoid t l cy chay gip bo qun m thn, c ch phn ng thi ghp thn; yu t bo v thn, hn ch tn thng t bo thn do thiu mu. -

Flavonoid c chit t l cy bch qu (Ginkgo biloba-thuc h Ginkgoaceae) cha cc cht dn cht ca Kaempferol, quercetin c tc dng ci thin c tun hon, c bit l tun hon no, lm tng tr nh, c tc dng tch cc trong cha bnh Alzheimer, ci thin chng lit dng.
-

Th nghim flavonoid chit xut t hoa kim ngn cng c tc dng lm gim cc ch s cholesterol ton phn, triglycerid v LDLC (hi cho tim) ng thi lm tng HDLC (li cho tim mch) trong huyt tng chut cng trng ung cholesterol thc nghim

Cc flavonoid cn c tc dng chng c, lm gim thng tn gan, bo v chc nng gan nh cynin, acid cafeic, chlorogenicc trong cy actiso (cynara scolymus L).

Bo the times of India dn li cc nh khoa hc cho bit, chnh hp cht flavonoid c trong c hnh vi c tnh chng oxy ho gip tiu dit cc phn t gc t do. C hnh c tc dng nga ung th (c bit l ung th d dy) huyt p cap v bnh tim, gip gim cholesterol v ngn nga chng x va ng mch, qua gip nga bnh tim.
-

Trong n hoa ho c cha flavonoid: rutin (rutosid) cao nht. Tc dng ca rutin (mt loi vitamin P) lm gim tnh thm ca mao mch, cng c sc bn thnh mch, hn ch hin tng suy gim tnh mch ngi cao tui.
-

- Cy thanh hao hoa vng cha cc hp cht flavonoid gm: quercetagetin, methyllether, tetramethylether v cc coumarin, cc dn cht polyacetylen.

Rt nhiu loi hoa cha cc flavonoid, polyphenol (nh hoa v i hoa cy dm bt) c tnh chng oxy ho, lm gim ri lon lipid mu, nguy c bnh tim mch.
-

Hesperidin v naringin l hai cht flavonoid c trong bi gip bo v tnh n hi ca mch mu no.
-

Nghin cu cho thy cc cht c trong chocolate c gi l flavonoid c th gip mch mu hot ng tri chy hn v c th gim nguy c bnh au tim. -

Mt nghin cu mi ca M c ng trn tp ch Journal of Agricultural and Food Chemistry khng nh rng cc cht flavonoid trong chanh c tnh nng ngn nga cc bnh thoi ho ca no.

Ngoi ra, flavonoid cn c trong mt s loi nh: cam qut, v v ht nho, u nnh .
-

KT LUN Flavonoids l mt nhm sc t thc vt c vai tr rt ln trong vic to ra mu sc ca nhiu loi hoa qu. Nhng nhin cu gn y cho thy flavonoid rt c ch trong cng vic iu tr v ngn nga nhiu tnh trng bnh l ca c th. Ngy nay chng ta cng bit nhiu loi thc phm, nc tri cy tho mc v mt ong c nhng tc ng dc l do chng c lin quan trc tip n thnh phn flavonoid. Flavonoid l mt nhm cc cht c gi l nhng ngi th sa cha sinh ha ca thin nhin nh vo kh nng sa cha cc phn ng c th chng li cc hp cht khc trong cc d ng nguyn, virus v cc cht sinh ung. Nh vy chng c c tnh khng vim, khng d ng, chng vius v ung th. Hn na,flavonoid l mt cht chng oxy ha mnh gip c th chng li cc tn thng do s oxy ha v cc gc t do mt cch hu hiu. Nh vy flavonoid cn c tc dng bo v h tim mch, gim nguy c t vong do cc bnh l tim mch nh thiu mu c tim, au tht ngc, nhi mu c tim, x va ng mch,... nh kh nng chng s oxy ha khng hon ton cholesterol (cng ging nh cc cht chng oxy ha khc nh vitamin C, E,). Ngc li nu lng flavonoid cung cp hng ngy gim i, nguy c cc bnh l ny tng ln r rt. Kh nng chng oxy ha ca flavonoid cn mnh hn cc cht khc nh vitamin C, E, selenium v km. Mi mt loi Flavonoit u mang li nhng li ch ring, nhng chng thng hot ng h tr nhau v ph tc dng thng chng cho ln nhau. Ngy nay c khong trn 11000 hp cht flavonoid c bit v cu trc. Flavonoid c khai thc s dng trong nhiu lnh vc: Thc phm, m phm v c bit ng vai tr quan trng trong y dc hc.

LI CM N

Vi lng knh trng v bit n su sc, em xin chn thnh cm n Thy Gio Phm Hu Chnh, giao ti, tn tnh hng dn v to mi iu kin cho em hon thnh ti ny. Em xin by t lng bit n ti cc thy, c gio ging dy ti b mn Ha Hc cng cc thy c gio truyn t cho em trong nhng nm qua. D em rt c gng, tuy nhin chc chn em c nhiu sai st, mong thy,c gio thng cm v gp thm cho em. Cui cng ti xin chn thnh cm n cc thnh vin trong gia nh, tp th lp VHVL Ha K2 gip ti v vt cht cng nh tinh thn trong sut qu trnh hc tp ti trng v trong qu trnh hon thnh ti. Em xin chn thnh cm n!

TI LIU THAM KHO Ho sinh cng nghip L Ngc T Ho hc cc hp cht thin nhin Bo The Times of India Tp ch Journal of Agricultural and Food Chemistry http://www suckhoe360.com http://www suckhoecongdong.com