DC LIU CHA

ALCALOID

NI DUNG

NH NGHA
CU TRC HA HC PHN LOI
TNH CHT L HA
PHNG PHP CHIT XUT
PHNG PHP KIM NGHIM
DC LIU CHA ALCALOID

KHI NIM V ALCALOID

Sertuner (c, 1783-1841)
1806, chit t Thuc phin 1 cht c tnh kim
v gy ng mnh, t tn l Morphin.
1810, Gomes, v cy Canhkina, tn l
Cinchonino
1817, Caventou v Pelletier (Php) tch emetin
t ipeca v
1818, tch strychnin v brucin t ht m tin.
1819, Meissner ngh xp cc cht c tnh
kim ly t thc vt thnh mt nhm ring,
c tn l alcaloid.
nh ngha: alcaloid l nhng hp cht hu c,
c cha nit, c phn ng kim v ly ra t
thc vt.

DANH PHP

Cc alcaloid thng c cu to phc tp nn khng gi theo danh

php v gi theo tn ring.

Tn ca alcaloid lun c ui in v xut pht t:

Tn chi hoc tn loi cy + in (v d: Papaverin t Papaver

somniferum; Palmatin t Jatrorrhiza palmata; Cocain t
Erythroxylum coca).

Da vo tc dng sinh hc ca alcaloid: Emetin do t s = gy

nn; Morphin t morpheus = gy ng.

C th t tn ngi + in: Pelletirin t Pelletier; Nicotin t J. Nicot.

Nhng alcaloid ph tm ra sau, thm tip u ng, hoc bin i v

ng chnh: v d nh in thnh idin, -anin, -alin).

PHN B TRONG THIN NHIN

Alcaloid ph bin trong thc vt, 6000 alcaloid t 5000 loi, hu ht

thc vt bc cao (15-10% tng s loi cy).
H Trc o 800 alcaloid, H Thuc phin 400 alcaloid, H Cam
chanh gn 400 alcaloid, H u 350 alcaloid H hnh, h C, h
Tit d, h C ph, h M tin, h Hong dng, h Cc, h Thu
du ..
H Rannunculaceae, Berberidaceae, Papaveraceae, Buxaceae,
Cactaceae c ti 50% loi cha alcaloid.
Nm c alcaloid trong nm ca kho mch,
ng vt, alcaloid nhm samandarin/tuyn da ca loi k nhng;
bufotenin t nha cc.

PHN B TRONG THIN NHIN

Trong cy, alcaloid thng tp trung mt s b phn nht nh. V

d nh alcaloid
ht M tin, c ph, ti c;
qu nh t, h tiu, thuc phin;
l nh Belladon, coca, thuc l, ch;
hoa nh C c dc;
thn nh Ma hong;
v thn nh Canhkina, mc hoa trng, hong b;
r nh ba gc, lu;
c nh u, bnh vi, Bch b.

PHN B TRONG THIN NHIN

Rt t khi trong cy ch c 1 alcaloid duy nht m l mt hn hp

alcaloid, trong alcaloid no hm lng cao gi l alcaloid
chnh, cn alcaloid khc c hm lng thp hn gi l alcaloid
ph.

Nhng alcaloid ca cng mt cy thng c cu to tng t

nhau, chng c chung mt nhn c bn. V d nh cc cht tropin,
hyoscyamin, atropin trong l Belladon u c trong h C;
Isopelletierin v Methylisopelletierin c trong v r lu c chung
nhn piperidin.

PHN B TRONG THIN NHIN

Cc alcaloid trong cng mt h thc vt thng c cu to rt gn

nhau. V d nh alcaloid trong cc cy h C nh Atropa belladonna
L., Hyoscyamus niger L., Datura metel L., Datura stramonium L.,
Datura tatula L. u c chung nhn tropan.

C khi trong cng 1 h nhng cu trc ha hc li rt khc nhau. V

d mt s cy trong h c ph nh cy cf c cafein (nhn purin),
cy canhkina (nhn quinolin).

C alcaloid gp nhiu h khc nhau nh Berberin c trong cy

Hong lin (h Hong lin), c trong cy Hong b (h Cam chanh),
c trong cy vng ng (h Tit d) v c trong cc loi Berberis
spp. (h Berberidaceae).

PHN B TRONG THIN NHIN

Hm lng alcaloid trong cy rt thp. Mt dc liu cha t 1

3% alcaloid c coi l kh cao.

Tr mt vi trng hp c bit nh alcaloid trong v cy Canhkina

(6 10%), alcaloid trong nha thuc phin (20 30%).

Trong cy alcaloid t khi tn ti dng t do (dng alcaloid base) m

dng mui ca cc acid hu c nh citrat, tactat, malat, oxalat,
acetat (i khi ca acid v c) tan trong dch t bo.

Mt s alcaloid kt hp vi tanin, hoc kt hp vi acid c bit ca

cy v d acid meconic trong thuc phin, acid tropic trong mt s
cy h C, acid aconitic trong cy u.

Cinchona spp. Rubiaceae

R1
MeO

R2

Alcaloid nhn quinolin

Quinine

Quinidine

R1

OH

R2

OH

Antimalarial

Antifibrillant

Papaver somniferum, Papavaceae

Alcaloid nhn isoquinolin

RO

H
NCH3

HO

Morphine

Codeine

CH3

Antalgic

Antalgic, antitussive

Catharanthus roseus (L). G.Don f. Apocynaceae

OH
N
N

N
H
H3COOC

OH

MeO

N
R H

OCOCH3
COOCH3

Nhn indol

Vinblastine

CH3

Vincristine

CHO

Vinorelbine = 5-noranhydrovinblastine

Leukaemia, testicular, kidney,

bladder, ovarian cancers,
Hodgkindisease
Acute lymphoblastic leukaemia
Lung and breast cancer

S TO THNH ALCALOID
TRONG CY ACID AMIN

Dc liu cha alcaloid khng c nhn d vng (Ma hong, t, Ti c,

ch mu)
Dc liu cha alcaloid c nhn pyridin v piperidin (H tiu, Lu, Cau,
Lobeli, Thuc l)
Dc liu cha alcaloid c nhn tropan (Benladon, C c dc,
Coca).
Dc liu cha alcaloid c nhn quinolin (Canhkina).
Dc liu cha alcaloid nhn isoquinolin (Ipeca, Thuc phin, Bnh vi,
Hong lin, Vng ng, Vng nem, Sen).
Dc liu cha alcaloid c nhn Indol (m tin, L ngn, Ca kha
mch, Ba gc, Da cn)
Dc liu cha alcaloid nhn purin (Ch, C ph).
Dc liu cha alcaloid c cu trc steroid (Mc hoa trng, C l x).
Dc liu cha alcaloid c cu trc diterpen ( u)

Quinolizidin

Lysin

N
H2N

H2N

COOH

Tropan

Omithin
H2N

H2N

COOH
COOH

Tyrosin

Isoquinolin
N

NH2
HO
H2C

COOH

NH2

Indol
N
H

H
C

Tryptophan
N
H

TNH CHT CHUNG CA ALCALOID

1. L tnh
Th cht
Th rn, cng thc cu to c C, H, N v O nh Morphin (C17H19NO3), Codein (C18H21NO3),
Strychnin, quinin ..
Th lng, CTCT khng c oxi nh Coniin (C8H17N), Nicotin (C10H14N2), spartein (C15H26N2)
tuy nhin c 1 vi alcaloid khng c oxi vn th rn nh sempecvirin (C 19H16N2)
Mi v
Khng mi, c v ng mt s t c v cay (piperin)
Mu sc
Khng mu, tr mt s c mu vng nh Berberin, palmatin
tan
Alcaloid base khng tan trong nc, d tan trong cc dung mi hu c nh MeOH, EtOH,
Ether, CHCl3,
Alcaloid dng mui tan trong nc v khng tan trong dung mi hu c
Nng sut quay cc
Phn ln alcaloid c kh nng quay cc v c C bt i. Mt s alcaloid l hn hp ng
phn t tuyn v hu tuyn (racemic).
C 2 dng ng phn D v L th alcaloid dng L c tc dng sinh hc mnh hn dng D.

TNH CHT CHUNG CA ALCALOID

2. Ha tnh

Tnh base yu (ngoi l c cht c tnh base mnh Nicotin; khng

c phn ng kim Theobromin, ricinin, colchicin; phn ng acid
yu arecaidin, guvacin).

Do tnh base yu nn c th gii phng alcaloid ra khi mui bng

kim trung bnh v kim mnh (NH4OH, NaOH, Na2CO3..).

Tc dng vi acid cho mui tng ng.

Alcaloid kt hp vi kim loi nng to phc

Alcaloid cho phn ng vi TT gi l TT chung, c chia lm 2 loi:

TT to ta v TT to mu.

TNH CHT CHUNG CA ALCALOID

2. Ha tnh
- Thuc th to ta
- TT Mayer (K2HgI4): ta mu trng
- TT Bouchardat (Iodo-Iodid): ta mu nu
- TT Dragendorff (KBiI4): ta vng cam n .

Phn ng to ta rt nhy.
- TT to mu
-

Acid sulfuric m c

Acid nitric m c

Acid sulfonitric (TT Edrdmann)

CHIT XUT, TINH CH V PHN LP

Nguyn tc chit xut: da vo tnh cht ca alcaloid

- tnh base yu
- tn ti trong cy dng mui

2 phng php chnh

1. Chit xut bng dung mi hu c trong mi trng kim
2. Chit bng dung dch acid long trong cn hoc nc

Dc liu
(alcaloid mui
acid hu c)

Dch chit DMHC

1. Thm m dc liu bng kim

(NH4OH, NaOH, Na2CO3 )
2. Chit bng dung mi hu c
khng fn cc (CHCl3, ether,
hn hp CHCl3 v ether). Chit
bng bnh Soxhlet, Kumagava.

(alcaloid base)

Dch chit acid

(alcaloid mui)

Dch chit DMHC

Chit vi dung dch acid long (2

5%) nh HCl, H2SO4,
CH3COOH
1. Kim ha bng kim pH = 9 10
2. Chit bng dung mi hu c khng
phn cc

(alcaloid base)
ALCALOID TH
Dung mi thu hi

Ct thu hi dung mi

(alcaloid base)

Dc liu
(alcaloid mui
acid hu c)

Dch chit acid

(alcaloid mui)

1. Chit bng acid long pha

trong nc hoc cn
2. Lc dch chit v ct thu hi
dung mi cn

1. Ra dch chit bng ether

loi tp
2. Kim ha pH = 9 10
3. Chit bng DMHC khng
phn cc

Dch chit DMHC

(alcaloid base)
ALCALOID TH
Dung mi thu hi

Ct thu hi dung mi

(alcaloid base)

TINH CH V PHN LP

Phng php trao i ion

Phng php sc k ct

Phng php sc k iu ch

NH TNH V NH LNG

nh tnh: da vo 2 loi thuc th chung ca alcaloid, TT to ta

v TT to mu.

nh lng:
- Phng php cn
- Phng php trung ha
- Phng php so mu (v d nh lng alcaloid v canhkina bng
TT Reinecker to ta mu, ha tan ta trong aceton).

CU TO HA HC V PHN LOI

Alcaloid khng c nhn d vng

Alcaloid c nhn d vng (12 nhm)

Alcaloid c nhn sterol

Alcaloid c cu trc terpen