NHM SV:NHM SV:NGUYN TH VN ANHNGUYN TH VN ANHNG TH IMNG TH IMTRN DUY KHANGTRN DUY KHANGDNG NGC PHCDNG NGC PHCNGUYN VN TNGUYN VN TNGUYN THNH DIPNGUYN THNH DIP

GVHD:

NGUYN VN HNG

NI DUNG CHI TIT1. Khi nim alkaloid1. Khi nim alkaloid

3. Phn loi alkaloid3. Phn loi alkaloid

4. Tnh cht ca alkaloid4. Tnh cht ca alkaloid

5. Chit xut v phn tch5. Chit xut v phn tch

7. Mt s hp cht alkaloid tiu biu7. Mt s hp cht alkaloid tiu biu

6. Thuc th alkaloid6. Thuc th alkaloid

2. Ngun ca alkaloid2. Ngun ca alkaloid

1.Khi nim v alkaloid1.Khi nim v alkaloidAlkaloid l nhng hp cht hu c c cha d vng nit, c tnh baz.

Thng gp trong nhiu loi thc vt v i khi cn tm thy trong mt vi loi ng vt.

c bit, alkaloid c hot tnh sinh l rt cao i vi c th con ngi v ng vt, nht l i vi h thn kinh. Vi mt lng nh c alkaloid l cht c gy cht ngi nhng li c khi n l thn dc tr bnh c hiu.

2. Ngun ca alkaloid2. Ngun ca alkaloidAlkaloid l hp cht c cha nit ngun gc thc vt. c s dng rng ri bo ch thuc (cafein, cocain, ephedrin...).

Hm lng Alkaloid c th t ti 10% trong cc loi rau qu thng dng nh khoai ty, ch, c ph.

Khoai ty sn sinh nhiu loi Alkaloid, trong nguy him nht l solamin v chaconin. Di tc ng ca nm mc, vi khun, nh sng... cc cht Alkaloid c hnh thnh v tch t trong c khoai.

Mm khoai ty l ni cha nhiu nht loi c cht ny (gp 100 ln c).

Trong ch, c ph v cacao c cha hp cht methylxathin, c xp vo h Alkaloid, gm thophylin, caffein v thobromin. Nhng cht ny u l cc cht kch thch h thn kinh trung ng v nh hng n tr nh.

V khoai ty cng cha hm lng Alkaloid nhiu gp 20 ln so vi c. hy cn thn vi nhng c khoai ty c v xanh; cht dip lc ny c hnh thnh do nh sng mnh chiu vo, i km l cc loi Alkaloid c hi.

Vi ngi bnh thng, mt tch c ph hay mt thanh chocolate cng lm mt cn bng axdrelanin, nonaxdrenalin v remin (nhng hormone tuyn thng thn tit ra iu tit nhp tim, huyt p...).

Phytat l cc loi mui ca calci phytic, thng kt hp calci trong thc n bi tit ra ngoi c th.

Cht phytat c trong la m, go, u tng rt dn calci trong c th ngi n. Ch, c ph, ca cao cha nhiu hp cht methylxathin d nh hng n tr nh.

Hm lng phytat trong ng cc khong t 2-5gr/kg. Khi c th ngi nhn 1g phytat th n lp tc mt i 1g canxi. iu ny rt bt li cho sc kho, c bit l tr em v ph n c thai.

Mt liu 5g acid oxalic c th gy t vong cho mt ngi ln nng 70kg.

Ngoi phytat, trong mt s loi rau qu cn cha nhiu axit oxalic- cng l mt cht chng canxi. Loi acid ny thng c kh, me...

Nguy hi hn, loi acid ny cn tc dng vi canxi, to thnh oxalat khng tan- mt nguyn nhn gy bnh si thn.

L, hoa, qu v r cy vi voi c cha axit Xyanhydric.

Nm 1969 J.M.Goweley v cng s pht hin mt s alkaloid c nhn pyrolizidinn v lasiocarpine c c tnh cao i vi gan v gy hu hoi t chc gan au bng, a chy, xut huyt lan t v c th gy ung th.

Mt s alkaloid gi l indixin.

3. Phn loi alkaloid3. Phn loi alkaloidCc alkaloid thng thng c phn loi theo c trng phn t chung ca chng, da trn kiu trao i cht c s dng to ra phn t.Khi khng bit nhiu v tng hp sinh hc ca cc alkaloid, th chng c gp nhm theo tn gi ca cc hp cht bit @ V d: do cc cu trc phn t xut hin trong sn phm cui cng; nn cc alkaloid thuc phin i khi cn gi l cc "phenanthren"), hay theo nhm ng/thc vt m t ngi ta chit xut ra cc alkaloid

Khi ngi ta bit nhiu hn v mt alkaloid c th no , th vic gp nhm c thay i phn nh cc kin thc mi, thng thng ly theo tn gi ca amin quan trng v mt sinh hc v ni bt nht trong tin trnh tng hp.Cc nhm alkaloid hin nay bao gm:

@ Nhm pyridin: piperin, coniin, trigonellin, arecaidin, guvacin, pilocarpin, cytisin, nicotin, spartein, pelletierin.

@Nhm pyrrolidin: hygrin, cuscohygrin, nicotin

@Nhm tropan: atropin, cocain, ecgonin, scopolamin .

@Nhm isoquinolin: Cc alkaloid gc thuc phin nh : morphin, codein, thebain, papaverin, narcotin, sanguinarin, narcein, hydrastin, berberin.

@ Nhm quinolin: quinin, quinidin, dihydroquinin, dihydroquinidin, strychnin, brucin, veratrin, cevadin.

@Nhm phenethylamin: mescalin, ephedrin, dopamin, amphetamin.

@Nhm indol: * Cc tryptamin: DMT, N-metyltryptamin, psilocybin, serotonin. * Cc ergolin: Cc ancaloit t ng cc/c nh ergin, ergotamin, axt lysergic v.v

* Cc beta-cacbolin: harmin, harmalin, yohimbin, reserpin, emetin.

* Cc alkaloid t chi Ba gc (Rauwolfia): reserpin.

@ Nhm purin: * Cc xanthin: caffein, theobromin, theophyllin.

* Cc alkaloid aconit: aconitin

*Cc steroit: solanin, samandari (cc hp cht amoni bc bn): muscarin, cholin, neurin.

@ Nhm terpenoit:

@Cc alkaloid t da cn (chi Vinca) v cc h hng ca n

* Vinblastin, vincristin.

Chng l cc cht chng ung th v lin kt cc nh trng (dime) tubulin t do, v th ph v cn bng gia trng hp (polyme ha) v phn trng hp vi qun, to ra s km hm cc t bo trong pha gia ca qu trnh phn bo.

4. Tnh cht ca cc alkaloid4. Tnh cht ca cc alkaloida/ Tnh cht vt l:

Phn t lng: khong 100-900

Cc alkaloid khng cha cc nguyn t xy trong cu trc thng thng l cht lng iu kin nhit phng (v d nicotin, spartein, coniin)

Cc alkaloid vi cc nguyn t xy trong cu trc ni chung l cc cht rn kt tinh iu kin nhit phng (v d: berberin)

Hu ht alkaloid base gn nh khng tan trong nc nhng tan trong cc dung mi hu c nh CHCl3, eter, cc alcol dy carbon ngn.

Mt s alkaloid do c thm nhm phn cc nh OH, nn tan c mt phn trong nc hoc trong kim ( Morphin, Cephalin).

Ngc li vi base, cc mui alkaloid ni chung tan c trong nc v alcol, hu nh khng tan trong dung mi hu c.

C mt s ngoi l nh Ephedrin, Colchixin, Ecgovonin cc base ca chng tan c trong nc, ng thi cng kh tan trong dung mi hu c, cn cc mui ca chng th ngc li.

Alkaloid c N bc 4 v N- oxid khc tan trong nc v trong kim, rt t tan trong dung mi hu c.

Cc mui ca chng c tan khc nhau ty thuc vo gc acid to ra chng.

4. Tnh cht ca cc alkaloid4. Tnh cht ca cc alkaloidb/ Tnh cht ha hc:

Alkaloid l cc base yu, do s c mt ca nguyn t .

Tnh kim ph thuc vo kh nng sn c ca cc cp in t n c trn nguyn t nit & v kiu khc (d) vng cng cc phn thay th.

a s lm xanh giy qu tm.

Vi acid thng to mui tan trong nc v kt tinh.

Tnh base gim dn theo th t mui amoni bc 4, amin bc 1, amin bc 2, amin bc 3.

Mui ca alkaloid rt bn, nhng chng b phn hy bi tia sng mt tri hoc tia t ngoi.Phn ng alkaloid c v ng v c tnh trin quang.

Chng to ta vi cc dung dch acid phosphotungstic, phosphomolipdic, picric

Ngoi tnh base, cc alkaloid c phn ng tng t nhau nh i vi mt thuc th, gi tn chung l cc thuc th alkaloid.

5. Chit xut v phn tch:5. Chit xut v phn tch:a/ Chit xut: C 2 cch loi tp

Sau tin hnh chit alkaloid bng mt trong 2 cch c bn sau,ty theo l tnh alkaloid d bay hi hay alkaloid n nh.

Ngm bt dc liu vi dung mi phn cc km nh eter du, eter trong vng vi gi n 1 ngy(trch ngui).

Chit lin tc vi eter du bng cch un hon lu, bt loi tp xong kh t nhin(trch nng).

Trng hp alkaloid d bay hi:

C trong cy trng thi mui.

Cy c phi kh v nghin nt thnh bt, cho cht kim phng thch alkaloid. Cht kim thng dng l vi, NH4OH, NaOH.

Sau chng ct li cun hi nc thu dc alkaloid.

Trng hp alkaloid ca base n nh:

Dng 2 phng php :

* Nu cy vi nc acid, alcol acid ha bng acid mnh. Trong iu kin ny alkaloid c chuyn sang dng mui ha tan trong nc hoc trong alcol long. Vic chn dung mi phi chn ph hp vi tnh phn cc ca alkaloid l trung bnh hay yu alkaloid tan tt vo pha .

Trng hp alkaloid ca base n nh:

Dng 2 phng php :

* Ch ha bt cy kh bi base mnh phng thch alkaloid .Dng NaOH, NH4OH, vi, MgOH,Na2CO3.

Lm kh dch chit p sut thp, chit bng dung mi thch hp ha tan alkaloid t do.

Mt s c tnh cn ch trong qu trnh chit:

* Trong cy alkaloid tn ti di dng mui ca cc acid hu c.

* Nhng mt s kt hp vi tanin, v vy i vi nguyn liu c nhiu tanin th nn dng dung mi c phn cc mnh hn.

* Hoc chit nng tch alkaloid ra khi tanin v ha tan vo dung mi.

Mt s c tnh cn ch trong qu trnh chit:

* Mt s alkaloid l ester nh Atropin, Cocain, Heliotrin, c th b thy phn trong qu trnh chit xut nn cn hn ch s dng nhit cao. * Ngc li mt s alkaloid tn ti di dng glycocid nh Solamaegin,solasonin, chit cc alkaloid ny cn c giai on thy phn * Nhn chung alkaloid l nhng cht tng i bn, nhng mt s t cht thuc dn xut indol rt d b phn hy do nh sng hoc tc nhn oxy ha kh

Nhn chung: Phn ly alkaloid trng thi tinh khit l mt vn kh khn lun lun trong qu trnh chit ngi ta thu c alkaloid. u tin phi tinh ch alkaloid bng cch kh ht tanin, resin, amino acid lm d chng. K , phn ly alkaloid bng cch ha tan trong dung mi thch hp hoc to kt tinh,to ta phn on. Cui cng , i vi cc phn oan 3,4 cht th s dng sc kh ct kt hp sc k lp mng, hoc sc kh trao i ion, tch ring chng ra .

5. Chit xut v phn tch:5. Chit xut v phn tch:b/ Phn tch:

* phn tch alkaloid phi qua quy trnh sau:

Lc ly dung dch mui,kim ha ly ancaloit hon ton khi mui.

Nghin nh nguyn liu thnh bt ri ngm vi dung dch HCl1%(hoc bng dung dch xa) chuyn ha hon ton ancaloit thnh mui clohidrat d tan.

Ct cun hi nc hoc chit bng dung mi hu c nh clorofom,benzen

Xc nh cu trc cc alkaloid th hot tinh sinh hc,em sn phm th nghim,ng dung.

Chy sc k hoc sc k bn mng iu ch...phn lp ring tng alkaloid.

*Sn phm thu c thng l hn hp nhiu alkaloid, hin nay ngi ta thng dng cc phng php sc k khc nhau (sc k ct, sc k bn mng, . . .) tch ring cc alkcaloid ra khi hn hp.

6. Thuc th alkaloid6. Thuc th alkaloidC 2 loi:

* Loi th nht :cho kt ta rt t tan,c nhy ln, dng tm alkaloid dng vt.

. Dung dch HgCl2

. Thuc th iodur

. Dung dch vi acid c trng lng phn t cao* Loi th hai:

. Dung dch acid picric bo ha trong nc

. Dung dch acid stibic bo ha trong nc

. Dung dch acid picrolonic bo ha trong nc

7. Mt s hp cht alkaloid tiu 7. Mt s hp cht alkaloid tiu biubiu

1.Nicotin:Cu to:

N trong cy thuc l di dng mui kt hp vi axit limonic. Trong l cy thuc l hm lng nicotin khong 10 - 16% thuc l v 16% thuc lo. Nicotin l cht lng nh du, khng mu, si 247 C, n nu li nhanh chng trong khng kh do b oxy ha, n d bay hi c mi thuc l, d tan trong c, dung dch c tnh baz mnh. Nicotin l mt alkaloid rt c, ch c vi mg cng gy nhc u, i ma, vi lng ln hn n km hm hot ng ca h thn kinh, lm ngng h hp, t lit hot ng ca tim, do khng nn ht thuc l.

Nicotin qua phi ri vo mu, c tc dng lm dy thnh ng mch, gy hp ng mch, hp mch vnh, dn ti hp van tim.

Mt khc nicotin cn lm ng mu trong mch mu, dn ti nhi mu c tim cp v c th dn ti t vong.Hm lng nicotin trong mu cng nhiu th s kch thch nhp p ca tim cng nhanh nn d dng gy nn bnh tng huyt p. Nicotin l mt cht d gy nghin, khi ht thuc l th mt lng nicotin vo mu, nu thiu n s gy kh chu, gy thm mun ht thuc l.

S tng hp nicotin t ornicothin:

2/cocain:

Cu to:

Cocain l alkaloid c trong l cy coca mc Nam M.

Cocain l cht kt tinh c tinh th hnh lng tr, c nhit nng chy l 98 C, kh tan trong nc, d tan trong ru v ete.

Cocain l thuc t tng phn rt mnh, l thuc gy m mnh, song l thuc c gy mt nhc, suy nhc c th, trong mt s trng hp th c th thay cocain bng novocain.

3/ Morphin:

Cu to:

Morphin l mt cht kt tinh c nhit nng chy l 230 C (ng thi phn hu), t tan trong nc, kt tinh ngm mt phn t nc, tan trong kim v c nhm phenol, morphin va c tnh baz, va c tnh axit yu (lng tnh).

L th thuc rt c gi tr trong y hc: lm gim au, thuc ng.

Morphin d gy nghin, nu lm dng th l cht ma ty cc k nguy him.

Gi tr qu gi ca morphin l tc dng gim au theo kiu tiu cm gic au, tc dng ln trung tm xc nh ca bn cu no: s tc ng ln trung tm ny l cc k qu bu v vi liu lng nh lm gim au m khng lm xo trn thc. Ngay nhng liu lng rt nh cng c tc dng n trung tm th, tn s th b gim xung, s h thp ca nhp th tc khc c tng ln cho n khi ph b cc cn ho tc khc.

Nu lng morphin ln s c hi, lm ngi cht do tnh trng t lit trung tm th.

Chng nghin codein l t hn, y li th cho n trong liu php c a ra. Tc dng gim au v tnh yn r rng l t hn nhiu so vi morphin. Codein c th tc dng kch thch (tnh b dng) ca cc dc liu khc c tng ln. Cng nh tc dng cha ho ca codein yu hn morphin nhiu nhng n c nhiu ci tt hn nh tnh cht khng b quen dn v khng b nghin.

Morphin c axetyl ha vi anhydrit axetic to thnh heroin.

Cc cng thc cu to ca cc hp cht isoquinolin:

4/ Quinin :

Cu to:

Cng vi nhiu alkaloid khc c cha trong v cy quinquina thng mc vng nhit i .Quinin l cht rn, tnc 1770C .

N c th kt tinh vi ba phn t nc v c tnc 570C, d tan trong etanol v ete.

Cc dung dch quinin c tnh baz v c v ng.Quinin c dng trong y hc di dng mui clohirat hoc sunfat. N l mt loi thuc tt chng bnh st rt v h st. Vi liu lng ln, quinin l cht c.

5/ Nhm phenethylamin

Ephedrin:

iu tr triu chng sung huyt mi, thng i km vi cm lnh, vim mi d ng, vim mi, vim xoang.

phng hay iu tr h huyt p trong gy t ty sng

6/ Indol Cu to:

Tinh th hnh l khng mu Tan trong nc, etanol, ete v dung dch amoniac; bay hi cng vi hi nc; mi kh chu.

7/aconitin (nhm terpenoit)Cu to:

Aconitin l mt ancaloit cc c c ngun gc t cc loi u N l mt cht c thn kinh c kh nng m cc knh ion Na+ nhy cm TTX tim v cc c quan khc, v n c s dng to ra cc m hnh lon nhp tim.Aconitin c cng thc ha hc C34H47NO11, v d ha tan trong cloroform hay benzen Aconitin c th b thy phn thnh benzoylaconin v aconin.

8/ Nhm Purin Caffein

Caffein, cn c gi l trimethylxanthine

L mt xanthine alkaloid c th tm thy c trong cc loi ht c ph, trong ch, ht cola, qu guarana v (mt lng nh) trong ht ca cao.