DC LIU CHA ANTHRANOID

MC TIU HC TP
C IM CU TRC 3 NHM ANTHRANOID PHNG PHP KIM NGHIM :

- NH TNH,
- NH LNG PHNG PHP CHIT XUT ANTHRANOID TC DNG SINH HC V CNG DNG CC DC LIU CHA ANTHRANOID

KHI NIM CHUNG : ANTHRANOID

Hp cht anthranoid nm trong nhm hydroxyquinon
O O O O

1 6 5 4
O

8 2 3
O

8 1 2 3 7 6 5
O

1 2 3

7 6 5
O

10

p-quinon

o-quinon

naphtoquinon

anthraquinon

Quinon l hp cht cha oxi, thng l cc dn cht thm b oxi ha, t cc hp cht phenol tng ng. Anthraquinon hay anthranoid : dn cht 9,10-anthracendion

PHN NHM : ANTHRANOID

ANTHRANOID

NHM
PHM NHUM

NHM
NHUN TY

NHM
DIMER

Phn nhm da vo cu trc ha hc, tc dng sinh hc, taxonomy ..

1- NHM PHM NHUM

C mu cam n ta Cu trc : 2 nhm OH v tr v Thng gp trong mt s chi h C ph (Rubia, Coprosma )
O O OH OH O OH OH

8 7 6 5
O

1 2 3

10

4
O O OH

anthraquinon

Alizarin (1,2-dihydroxyanthraquinon)

Purpurin (1,2,4-trihydroxyanthraquinon)

1 - NHM PHM NHUM

Acid carminic ( dng mui nhm l carmin) : mu (bo ch, m phm), chit t loi su Dactylopius coccus sng trn nhiu loi xng rng thuc chi Opuntia h Xng rng.
Acid kermesic : cht mu cho bi loi su Kermococcus ilicus
OH Glc O CH3 COOH

HO OH O

OH

Acid carminic l C-glycosid

Acid kermesic : khng c C-glycosid

Cnh kin sn phm ca su Lacifer lacca to ra trn cnh mt s cy ch nh u chiu Cajamus indicus Spreng; cy Ficus religiosa L.). TPHH ch yu l nha (75%) ch shellac nh bng (verni) g Sn phm ph mu sm l acid laccaic A, B, C v D.

2 - NHM NHUN TY
Cu trc : 2 nhm OH v tr 1 v 8

v tr C3 : CH3, CH2OH, CHO v COOH : nhm oxymethyl

Thng gp cc dn cht ca C3 trong cng mt loi nh i hong, cht cht, tho quyt minh.
O OH O OH

8 7 6 5
O

1 2 3

Chrysophanol Aloe emodin

R O

R = CH3 R = CH2OH R = COOH

10

Rhein

anthraquinon

2 - NHM NHUN TY
- Dn cht anthranoid c th tn ti trong thc vt di dng oxy ha (anthraquinon) hoc dng kh (anthron, anthranol)
O O OH

+ H2 - H2
H O H

Anthraquinon

Anthron

Anthranol

- Dng kh c tc dng x mnh nhng gy au bng. - Nn mt s dc liu cha Anthranoid phi 1 nm sau khi thu hi mi s dng chuyn dng kh thnh dng oxi ha.

3 - NHM DIMER
- Dn cht anthranoid dimer do 2 phn t dng anthron b oxy ha ri trng hp to dianthron.

- Khi to dimer nu 2 na phn t ging nhau gi homodianthron (sennosid

A, B), khc nhau gi l heterodianthron (sennosid C, rheidin A)
OH O OH OH O OH

H3C H H

OH

H3C

OH

OH H H3C H OH H3C

OH OH

OH

OH

2 phn t emodin anthron

Diemodin anthron

PHN B TRONG THIN NHIN

Anthranoid c phn b trong khong 30 h thc vt, ch yu l cy hai l mm. Cc h thng gp l Caesalpiniaceae, Rhamnaceae, Rubiaceae v Polygonaceae.

Trong cy 1 l mm rt him, ch c 2 cy c bit cho n nay l Aloe spp. v Hemerocallis aurantiaca.

C trong nm v a y. Trong ng vt th gp trong cc loi su nh Coccus cacti (Dactylopius coccus), Kermococcus ilicus, Lacifer lacca.

TNH CHT V NH TNH

Tnh cht l - ha

Sc k
Quang ph nh lng
- Phng php cn
- Phng php so mu - Phng php th tch

Chit xut

TNH CHT L HA
Dn cht anthraquinon u c mu t vng, vng cam n .
D thng hoa nh tnh bng vi thng hoa anthraquinon trn lam knh. Dng glycosid tan trong nc, dng t do (aglycon) tan trong dung mi hu c. Dn cht oxyanthraquinon (c 1 nhm OH v tr ) cho mu vi Mg(CH3COO)2/EtOH, V d : 1,2-dihydroxy cho mu tm

1,4-dihydroxy cho mu ta
1,6 v 1,8-dihydroxy cho mu cam.

TNH CHT L HA
Dn cht nhm nhun ty (1,8-dihydroxyanthraquinon) -

Phn ng Brntraeger
Trong dung dch kim to phenolat c mu , di UV cho hunh quang tm hoc nu.

SC K
Chun b dch chit

- chit bng MeOH (dng t do v glycosid)

- thu phn bng acid (H2SO4 25%), chit bng CHCl3 (dng oxy ha)

H dung mi khai trin: EtOAc MeOH H2O (100 : 17 : 13)

Thuc th pht hin: KOH/EtOH (nh sng thng v UV) hoc Mg(CH3COO)2/EtOH

CHIT XUT
Chit dng glycosid dng cn EtOH, MeOH hoc hn

hp cn - nc.
Chit dng aglycon, thy phn bng acid sau chit bng ether hoc chloroform. Chit dng oxi ha phi chuyn anthranoid dng kh sang dng oxi ha. Ch : Anthranoid tn ti trong t nhin dng t do (aglycon); dng ton phn (aglycon v glycosid).

NH LNG
1. 2. Phng php cn (D Lin x p dng nh lng nhm oxymethylanthraquinon trong i hong, ) Phng php so mu: da trn phn ng mu Borntraeger = Phng php Auterhoff. ng cong chun c xy dng vi cht chun istizin (1,8-dihydroanthraquinon) hay acid

chrysophanic, dung dch cobalt chlorid.

3. Phng php th tch: dng KOH 0,1N tc dng vi dn cht anthraquinon sau chun kim d bng HCl 0,1N (phng php ny t dng v thiu chnh xc)

TC DNG DC L V CNG DNG

Dn cht anthranoid d ha tan trong nc, khng hp

thu v khng b thy phn rut non. rut gi,

anthraquinon b kh thnh dng anthron v anthranol c tc dng ty x (liu thp, liu cao).

Dn cht anthranoid c tc dng thng mt.

Dn cht anthranoid c tc dng kch thch min dch, chng ung th
O OH CH2OH OH

Doxorubicine

OH

O-daunosamine

DC LIU CHA ANTHRANOID

1. Dc liu cha anthranoid thuc chi Cassia (Phan t dip (Sen); Tho quyt minh; Ct kh mung; Mung tru; mi) Dc liu cha anthranoid thuc h Rau rm Polygonaceae (i hong; Ct kh c; H th , Cht cht) Nhu

2.

3.

4.

L hi

DC LIU CHA ANTHRANOID THUC CHI CASSIA Nu tn cc dc liu cha anthranoid thuc chi Cassia

- Tn khoa hc
- B phn dng - Thnh phn ha hc chnh - Hm lng - Cng dng

Tn khoa hc

B phn dng

Thnh phn ha hc

Cng dng

Phan t dip

C. angustifolia l C. acutifolia

Anthranoid t do (t) Anthranoid glycosid (dimer): sennosid

Nhun ty

Tho quyt minh

Ct kh mung Mung tru

C. tora

ht

Chrysophanol. Physcion, emodin

Physcion, emodin Cht nhy

au mt, gii nhit

Nhun, gip tiu ha, to bn Nhun ty, hc lo

C. occidentalis C. alata

ht

L cht Chrysophanol, aloe emodin, rhein, emodin

mi

C. grandis

Cm qu

Rhein, sennosid A v Kch thch tiu B ho, au lng

DC LIU CHA ANTHRANOID THUC CHI CASSIA Phan t dip

c im thc vt: ch c 2 loi C. acutifolia v C. angustifolia. 2 loi ny khc nhau s i l cht v c im l cht. Thnh phn ha hc: ngoi cc anthranoid dng t do nh rhein, aloe emodin (chim t l t) th anthraglycosid chim ch yu: sennosid A v B. - dn cht flavonoid, cht nha (tc dng ph: au bng).

DC LIU CHA ANTHRANOID THUC H RAU RM 1. 2. 3. 4. i hong Rheum palmatum L., R. tanguticum, R.

officinale, thn r
Ct kh c Poligonum cuspidatum, r H th (ch : H th trng) Polygonum multiflorum, r c Cht cht Rumex spp, nh R. wallichii, R. crispus

NHU
Morinda citrifolia L., Rubiaceae

c im thc vt: cy g nh. L mc i, l km gn trn, nguyn hay ch 2-3 thy nh. Hoa mu trng, hnh u nch l. Qu hnh trng, l qu kp do nhiu qu dnh li vi nhau. Rut qu c lp cm mm n c. Cy c trng nhiu min trung v min nam. B phn dng: R, qu v l
Thnh phn ha hc: anthranoid (dn cht c nhm th OH, OCH3 v CH3 C1, 2 v 3)

NHU
Cng dng Cao huyt p (r), Nhun trng, d tiu ha (qu) Cha vt thng, mn nht, chng ln so, cha st (l). - Nc ung NONI c tc dng tng cng min dch, phng chng ung th.

DC LIU CHA ANTHRANOID CHI MORINDA

Morinda officinalis Ba kch

Morinda citrifolia Nhu

Morinda umbellata Dy t

L HI = NHA M
Aloe ferox v Aloe vera, h L hi Asphodelaceae.

c im thc vt:
Cy sng nhiu nm, thn c th ha g. Phn trn mang l. L hnh mi mc dy,mng nc, c nhiu cht nhy. Khi ra hoa, trc hoa nh ln gia b l, mang chm hoa mu hoc vng. B phn dng: nha l hi v gel l l hi. Thnh phn ha hc: Nha l hi: anthranoid (barbaloin: 1,8dihydroxyanthraquinon, C3=CH2OH, aglycon (anthron ca aloe emodin), glycosid dng C-glycosid, C10=-D-glucose, 15 30%)

L HI = NHA M
Gel l l hi: cht nhy

Cng dng:
- Nha l hi: liu nh l thuc b tiu ha, kch thch nh nim mc rut, tc dng thng mt. - Liu trung bnh c tc dng nhun, - Liu cao c tc dng ty x. - Gel l l hi (cao l l hi) dng trong m phm lm kem chng nng, thuc m lnh so,