Phn 2

DC LIU
CHA ANTHRANOID
1.

i hong

4.

Mung tru

2.

Nhu

5.

Tho quyt minh

3.

Phan t dip

6.

L hi

THAM KHO :
1- H th

2-Cht cht 3-Ba kch 4-ct kh c

1

I HONG

NOI DUNG

1. nh danh thc vat & dc lieu

2. Mo ta thc vat, bo phan dung

3. Thanh phan hoa hoc chnh
Anthranoid
Tannin
4. Chiet xuat
5. nh tnh
6. nh lng
Theo DVN II

Theo DVN III

7. Tac dung sinh hoc Cong dung

1. NH DANH
ai hoang gom nhieu loai thuoc chi Rheum, ho Polygonaceae

DTQ quy nh 3 loai

DVN III quy nh dung

- R. palmatum L.

- R. palmatum L.

- R. officinale Baillon

- R. officinale Baillon

- R. tanguticum Maxim ex Balf.

- R. palmatum officinale

palmatum : hnh ban tay

officinale : dc dung
4

2. MO TA
Cay: than thao, ln (2 m)
La: la ln (30 cm), moc thanh cum t than re, cuong dai,
co be cha (Polygonaceae), mep la xe thuy chan vt sau
(R. palmatum sau hn R. officinale), mat di noi gan o

tm nhat.
Than re: rat phat trien (bo phan dung)

Hoa: ngon, thng moc thanh chum

Qua: co 3 canh
5

PHAN BO
- Trung quoc, chau Au

- Viet Nam con phai nhap

THU HAI
- Thu than re t cay tren 3 tuoi
- Cat bo re con

- Thai phien phan than re

- Bao quan 1 nam mi dung
7

BO PHAN DUNG
Rhizoma Rhei
Than re a cao vo, say kho cua cac loai ai hoang
- Rheum palmatum L.

- Rheum officinale Baillon

- Rheum palmatum officinale, ho Polygonaceae

BO PHAN DUNG
Rhizoma Rhei

2. Manh mo mem

1. Manh ban

Soi bt

3. Si

5. Hat tinh bot

4. Calci oxalat
hnh cau gai

10

3. THANH PHAN HOA HOC

Chu yeu : anthranoid (3% - 5%) va tannin (10%, PC > PG)
@. Aglycon (anthraquinon)
- anthraquinon t do dang oxy hoa
- anthraquinon dimer dang kh

khoang 0.1 0.2%

@. Glycosid (anthraglycosid)

- glycosid dang oxy hoa

khoang 2 4%

- glycosid dang kh (anthron, anthranol)

- glycosid dang dimer
11

THANH PHAN HOA HOC

@. Anthraquinon t do dang oxy hoa
OH

OH
1

R6

R3
O

R6

R3

- Chrysophanol

Me

- Aloe emodin

- Rhein

CH2OH

- Emodin

OH

Me

- Physcion

OMe

Me

COOH

12

THANH PHAN HOA HOC

@. Glycosid vi aglycon dang oxy hoa hay dang kh

- chrysophanol

- Aloe emodin
- Rhein
- Emodin

OH gan glucose

- Physcion
@. Glycosid hoac aglycon dang dimer kh
- Rheidin A, B, C,
- Sennidin A, B, C,
- Palmidin A, B, C,
13

Cu tao cua cac dimer aglycones

Anthron 1

va Anthron 2

Tao thanh

Rhein

Rhein

Sennidin A va B

Aloe emodin

Rhein

Sennidin C

Emodin

Rhein

Rheidin A

Chrysophanol

Rhein

Rheidin B

Physcion

Rhein

Rheidin C

Aloe emodin

Emodin

Palmidin A

Aloe emodin

Chrysophanol

Palmidin B

Emodin

Chrysophanol

Palmidin C

14

Cau truc cac dimer anthrones

OH

OH

R6

R3

R6

R3

OH

OH

Cac dimer aglycon

15

Cau truc cac dimer glycosid.

glc

OH

COOR
COOH

glc

OH

Cac dimer glycosid

16

4. NH TNH
4.1. Phan ng Borntrager :
cua anthraquinon (t do va mi sinh)
cua chrysophanol (t do va mi sinh)

4.2. Phan ng tao chelat vi Mg acetat

4.3. Phan ng vi Pyridin MeOH

4.4. Th nghiem vi thang hoa (ket hp vi Borntrager)

4.5. nh tnh so sanh

4.6. nh tnh phan biet

17

5. NH TNH
4.5. nh tnh so sanh
- Chiet bang MeOH, co dch chiet en can

- Thuy phan bang HCl (BM 30 phut)

- Chiet anthraquinon bang ether, boc hi ether,
- Hoa cn / CHCl3, cham SKLM (silica gel F254)
- Khai trien 2 chieu vi 2 he dung moi

- Phat hien : UV 254 nm (so vi chuan)

18

5. NH TNH
4.6. nh tnh phan biet D Phap
Khi lan loai Rheum rhaponticum hay R. undulatum :
se co Rhaponticosid (xanh da tri sang / UV 365)
kiem tra bang SK G vi he BAW (4 : 1 : 5) / UV

C
T
hRf = 50 55

70

80

95

mau th T a b lan rhaponticosid

19

6. NH LNG
6.1. Phng phap Auterhoff (DVN II)
-Thuy phan trc tiep vi AcOH bang, va ether
- un soi 15 phut hoi lu (Sinh han nc rat lanh)
- e nguoi, tach lay ether .
- lac dch ether vi dd (NaOH + NH3)
- Tach lp kiem (mau o), un hoi lu 15
- o quang (550 nm) - So sanh vi dung dch giai mau CoCl2
- (A cua d.dch CoCl2 1% # A cua d.dch istizin 3,6 ppm)
ai hoang phai cha 2,5% anthranoid, tnh theo Istizin

20

6. NH LNG
6.2. Phng phap DVN III, 2002
- Chiet m (g) mau bang nc nong cach thuy.
- e nguoi, them Na bicarbonat, lac, loc lay dch
- Oxy hoa bang FeCl3 2% nong, thuy phan (HCl nong)
- Chiet aglycon bang ether, can ether + Mg acetat / MeOH
- o o hap thu A 515 nm (khong dung chuan)
- Ket qua c tnh trc tiep

X% = 64 A / 100m

ai hoang phai cha 2,2% anthranoid (tnh theo rhein)

Mun nh lng cac anthranoid acid ta lc dch chit ether
vi Na bicarbonat ;
21

7. TAC DUNG VA CONG DUNG

- Dang kh / dc lieu ti co tac dung kich ng can lu kho
- Hoat chat thc s (/ ai trang) : aglycon dang kh mi sinh
- C che : nhu ong c trn (ruot, t cung, bang quang ...)
- Tac ong sau khi uong : cham (nhuan, xo , tay)

- chuyen hoa : co qua sa, mt t qua gan, chu yeu : phan

Chu y:
- Khong dung : thai phu, ang hanh kinh, ang cho con bu, tr
- Ngi co nguy c ket soi oxalat, viem bang quang
- Dung lau : tao bon

- oi khi nc tieu va phan bi nhuom hong

22

- Cac vi khuan tai ruot gia cat

Sennoside A, B, C, D (8 O-glycosid) + (Sennidin)

- Sennidin b kh tiep rhein anthron + anthron khac

co tac dung nhuan tay.
- Sau khi uong khoang 8 h : co tac dung.
- Sau 24 h thai tr : ng tieu (30%), phan (20%)
- T 24 48 h

: lng thai ch con khoang 2%

- Tang thai : nc tieu, Natri va Kali

23

7. TAC DUNG SINH HOC

- Cac anthraquinon (Rhein, Emodin, Aloe emodin)

c che Bacillus subtilis, Staphylococcus aureus.

- Rieng Rhein (co COOH)

c che cac vi khuan yem kh chu yeu cua he tieu hoa

(nh c che c che chuoi ho hap te bao tai giai oan ty
the)
can tr chc nang kh cua NADH dehydrogenase)
-Emodin khang khoi u va chong di can cua te bao ung th
(2006)
-Lieu dung : 0,1g (Bo); 0,15g (nhuan); 0,5-2g (So)

24

MT VI BI THUC THNG DNG

Tr chng lipid huyt cao: dung con chiet xuat ai hoang , lam
thanh vien 0,25g,moi ngay uong luc sang sm 3 vien x 3 tuan, kt
qua tt; s bnh nhan tri glyceride va beta-lipoprotein cao t kt
qu 76%;
Tr chung trng v thc nhiet, tao bon :
ai hoang : 10 - 15g, Hau phac : 8g, Ch thc :8g, sac uong
Mang tieu : 10g ( hoa ung) neu bung chng;
Tr chan thng do te nga:
i hong, ng qui lng bng nhau tn bt mn,

10g x 2 ln/ngy, ung vi ru.

Tr bong gn, huyt au do t ng, trong ung ngoi xoa.
Tr xut huyt tiu ha trn: dng bt (vin hoc sir) i hong
mi ln ung 3g, ngy 3 ln ,kim tra phn m tnh hoc dng
tnh nh mi thi ung, Bnh qun thi gian cm mu l 2 ngy,

25

PHAN TA DIP

Cassia
angustifolia
(L hp)
26

1. M TA
Co 2 loai thng dung:
- Cassia angustifolia Vahl., Phan ta dip n
- Cassia acutifolia Del., Phan ta dip Ai cp
Cy: nho, cao n 1 m, moc thanh bui.
La: kep lng chim chn, loai C. acutifolia co t 4 5 i la
chet, C. angustifolia co 5 8 i, inh nhon.

Hoa: moc thanh chum nach la, canh mau vang, co 10 nhi,
co 3 nhi lep.
Qua: loai qua u det, cha 6 8 hat
27

1. C iM THC VT
Phan t :

Cassia angustifiolia Vahl.

(L hp)

Cassia acutifolia Del.

(L nhn)

Phan ta l hp

Phan ta l nhn

Ngun gc

Arab

Phi chu

Trng nhiu

Ai cp

di, hp

ngn, mp

nhiu hn

it hn

L, qua
S l cht

Vit Nam

+++

28

2. THNH PHN HOA HOC

@. Cac anthranoid dang t do (0,05 0,10%)
Rhein, aloe emodin, chrysophanol
@. Cac dimer anthranoid (2-3%):
Sennosid A, B = dirhein anthron

Sennosid C, D = rhein anthron + aloe emodin anthron

@. Cac flavonoid: kaempferol, isorhamnetin

@. Cht nha: gy au bung, tan trong cn va nc nong

nhng bi tua khi ngui. Do o cn ngui va loc loai
nha trc khi ung.
29

Glc

Glc

OH

OH

rhein
COOH

rhein
H

COOH

COOH

CH2OH

rhein
Glc

OH

aloe emodin
Glc

OH

Sennosid A, B

Sennosid C, D

(homo-dianthron)

(hetero-dianthron)

hot cht chnh

30

3. INH TNH
3.1. Phn ng Borntraeger (Anthranoid + kim mu )
3.2. Sc k lp mng
Dch chm: dch cn Phan t dip
H dung mi: n-propanol-EtOAc-nc (4:40:30)
Pht hin: phun HNO3 25%, sy 120 OC/10 pht, phun tip
dung dch KOH 5%/ cn 50 %. Kt qu phi cho 2 vt nu ta

ca sennosid B (Rf 0,1-0,2) v 2 vt sennosid A (0,3-0,35).

Tin hnh song song vi mu chun

31

SC K LP MNG

mu = dch chit cn nc

bn = silica gel F254

hdm = n-PrOH EA H2O (4 : 40 : 30)

sau khai trin :

- oxy ha vt

= HNO3 nng, sy kh

- hin mu vt

= KOH / ROH

so vi 05 vt chun
sennosid A, B, C, D v rhein glucosid

32

4. INH LNG
Phng phap D Phap 1972
- Chiet m (g) mau bang nc nong cach thuy.
- Acid hoa = HCl, lc vi CHCl3, loi CHCl3.
- e nguoi, them Na carbonat, lac, loc lay dch

- Oxy hoa bang FeCl3 10%, thuy phan (HCl nong)

- Chiet aglycon bang ether, can ether + KOH 1N
- o o hap thu A 500 nm
- o hp thu ca 1 dd chun 1,8-diOH anthraquinon
bit nng .

- Tnh kt qu, bit 1 mg 1,8-diOH anthraquinon ~ 1,797 mg

sennosid.
33

NH LNG

bt PTD

dch nc nng

+ vi git HCl, ra = Cf (loi chlorophyll + AQ + nha)

dch nc acid
Na2CO3,(pH 7-8) + (FeCl3 + HCl, )

dch thy phn + oxy ha

chit kit = Et2O

dch ether ln acid, mui

o Abs. 500 nm
// dd. chun Istizin

ra = H2O

dch ether

cn ether

KOH

mu

1 mg Istizin # 1,8 mg sennosid

34

TAC DUNG & CNG DUNG

Cng dung ch yu : nhun ty
Ung:

C tc dung sau 8 12 gi
(thut: tc dung nhanh hn)

C ch:

Kiu AQ (tng nhu ng c trn)

- kch thch tiu ha (1 2 gam l)

Chu y:

- nhun trng

(3 4 gam l)

- ty, x

(5 7 gam l)

Loi b cht nha

(gy au bung)

bng cch ra vi ru, lnh dch nc . . .

S dung:

L (ch yu); Qu (b ht); Sennosid A, B.

Chng chi nh: Kiu AQ

35

5. TC DNG V CNG DNG

Tac dung kch thch tiu hoa, nhun va ty tu theo liu
s dung.
- Liu gip tiu hoa: 1-2 g l
- Liu nhun: 3 4 g l

- Liu x: 5 7 g
Chng chi inh i vi ngi co thai, vim t cung, bang
quang.
Dang dung: thuc hm hoc thuc thut. Tuy nhin nn
ra cn hoc loc loai nha trc khi dung tranh au

bung.
36

Lc mu v ty c c th bng Tr PHAN T DIP

i vi nhng ngi b bnh gan nh vng da, x gan, p xe gan,
vim gan Hepatitis A,B,C,E hay ung th gan.. s c du hiu chn
n v khi xt nghim ch s men gan SGOT v SGPT (serum
glutamic oxaloacetic transaminase v serum glutamic pyruvic
transaminase) tng cao hn bnh thng gp 2-5 ln lm tiu hy
t bo gan.

Du hiu khi bnh khi no th ch s men gan gim. Tt c cc

bnh gan sau khi ung Phan T Dip vi liu cao 12g/ln, ngy
ung 2 ln, b Phan T Dip vo 1 ly nc si ngm 30 pht, hay
nu si cho thuc thm ra tr thnh nu hng m, ung ht 1 ln
mt ly, vn n ung bnh thng, khi i cu ra phn en lng tiu
chy, tip tc ung cho n khi i phn d dng v phn khng
lng nt na m tr li phn do, mu vng, th ngng.
Khi i th men gan SGOT, SGPT gim xung bnh thng th khi
bnh.
Ung phng bnh th liu 4g/ ngy c tc dng lc mu v gim
37
men gan.

MUNG TRU

38

1. M T
Tn khoa hoc: Cassia alata L. Fabaceae
Dang cy: nho; cao 1,5 m 3 m, thn g mm, d = 10-12 cm.
L: la kep lng chim chn, dai 30-40 cm, co t 8-14 i la
chet hnh trng, gc va inh la u trn.

Cum hoa: moc thanh bng dai 12-14 cm, rng 5-6 cm, mang
cac hoa mau vang sm.

Qua: loai qua u, dai 8-16 cm, c 2 canh sut theo chiu doc
cua qua, bn trong co 40-60 hat.

39

2. THNH PHN HO HOC

@. Trong la co cha cac dn cht anthranoid: chrysophanol,
aloe emodin, rhein, emodin.
@. Trong r co 2 dn cht anthraquinon c phn lp:
- 1,3,8-OH, 2 CH3-anthraquinon (1)

- 1,5-OH, 2-CH3, 8-OCH3, 3-O-glucosyl anthraquinon (2)

@. Kaempferol
OH

(1)

OH

OMe O

OH

CH3

CH3

OH

O-glc
OH

(2)

40

3. TC DNG V CNG DNG

La co tac dung nhun va ty tu theo liu s dung.
La cn dung cha hc lao bng cach gi nat ri xat vao
ni bi nm.

41

THO QUYT MINH

42

43

1. M T
Tn khoa hoc: Cassia tora L. Fabaceae
Cy: nho, cao 30-90 cm, moc hoang nhiu ni trong
nc.
L: kep, lng chim chn, gm 3-4 i la chet, la km
hnh si dai 1 cm. La chet hnh trng ngc.
Hoa: moc k la, mau vang, co t 1-3 chic.
Qua: loai qua u hnh tru, dai 12-14 cm, trong cha
vai chuc hat

44

2. B PHN DNG

B phn dung la hat gia

3. THNH PHN HO HOC

Hat cha chu yu la cht beo va anthranoid:
Chrysophanol

Aloe emodin

Physcion

Rhein

Emodin
Cac glycosid cua cac aglycon trn

45

3. THNH PHN HO HOC

Ngoai ra cn cha mt s dn cht khng thuc nhom
anthranoid nh:

Rubrofusarin

nor-rubrofusarin

Rubrofusarin 6-gentibiosid

toralacton

4. CNG DNG
ng y dung cha au mt o, mt m, chay nhiu
nc mt, quang ga.
Cn dung cha nhc u, mt ngu, giai nhit, b thn
Lu : khi s dung nn sao vang loai bt cht c
46

Aloe vera L.
Aloe ferox Mill.

Asphodelaceae
(Alloen = ng, ting Arab)

47

48

1. M T THC VT
Aloe vera L.

Aloe ferox Mill.

Thn cao

< 0.5 m

2 5 mt

Hoa

mu vng

mu

L c gai

mp

mp + di

C nhiu

Vit Nam

Nam Phi

Aloe vera L. var. chinensis (Haw.) Berger, Asphodelaceae

49

Aloe spp.
Chi Aloe 180 loi 04 loi dng lm thuc.
Trong 04 loi ny, c 02 loi thng dung
Aloe vera L. = A. vulgaris Lam.
= A. barbadensis Mill. = L hi Barbade
Aloe ferox Mill.
= Bitter Aloe = L hi x Cape
50

Aloe vera L.

Aloe ferox Mill.

51

52

Aloe vera

Aloe ferox

53

2. B PHN DNG
2.1. Dch c c t l = Nha L hi = ALOE
2.2. Gel ca l; Bt l (sau khi thu nha)

3. CCH THU HI - CH BiN

3.1. Thu hoch nha L hi

- Phng php th s
- Phng php hin i

3.2. Ch bin Bt l L hi
54

L HI

55

56

57

58

x l L hi

59

co ly gel

60

61

62

3. THNH PHN HA HC
3.1. Cc OMA
- aglycon

(aloe emodin; dch ti khng c)

- C-glycosid (barbaloin ** = aloin A + aloin B)

- glycosid hn tp (aloinosid)

3.2. Cc glycosid khc

- aloenin, aloesin
3.3. Carbohydrat (mono- v polysaccharid **)
- ng chu y l cc PS kiu gluco-mannan
3.4. Khong, vitamin, enzym, lignin, saponin, sterol,
amino acid, salicylic acid.
63

3. THNH PHN HA HC
OH

OH

OH

OH

CH2OH

CH2OH

aloe emodin
OH

glc

barbaloin **

OH

OH

OMe
OH

CH2O
H

glc

aloinosid

Rha

Me
H

glc

homonatalosid

64

4. NH TNH NHA L HI
4.1. Ph.ng Borntraeger (+ kim)

: anthranoid ni chung

4.2. Ph.ng Schouteten (+ Na borat): anthranoid dng kh

4.3. Ph.ng vi ddch Brom

4.4. Phn ng Klunger (+ ddch CuSO4)

Phn bit
2 loi L hi

4.5. Ph.ng vi acid periodic; acid nitric

65

4. NH TNH NHA L HI
4.2. Phn ng Schouteten
dch nc t

+ bt Na borat

nha L hi

pha long / nc

h.quang vng sng

(di UV 365 nm)

loi tp = bt Talc

4.3. Phn ng cng hp vi Brom

dch nc t
nha L hi

+ ddch Br2

ta mu vng
66

4. NH TNH NHA L HI
4.4. Phn ng Klunge (A. vera // A. ferox)
dch nc t

nha L hi

+ dd. CuSO4
NaCl / EtOH

mn bn (vera)
vng (ferox)

4.5. Phn ng vi HIO4 (A. vera // A. ferox)

dch nc t
nha L hi

+ HIO4 1%

bn (vera)
hng* (ferox)
* mt sau 1 h
67

4.6. Phn ng vi HNO3 (A. vera // A. ferox)

dch nc t

nha L hi

+ HNO3

nu (vera)
xanh vng (ferox)
(DVN III)

68

4. NH TNH NHA L HI
4.7. Sc ky (SKLM hay SKG)
Dung mi : phn cc (barbaloin >> aloe emodin)
Pht hin :
- phun, nhung d.dch Na borat hay KOH/cn
- soi UV 365 nm

4.8. Th tan : tan gn hon ton trong:

- trong ammoniac long (1 NH4OH/9 nc)
- trong cn 60%
69

5. NH LNG BARBALOIN
5.1. Phng php o quang trc tip ( 390 nm)
- kt hp SKG, so vi chun
- kt hp SKLM, so vi chun

5.2. Phng php o quang gin tip

- th.phn + oxy ha = FeCl3 + HCl 4N aloe emodin
- chit dch thy phn bng CCl4
- +NaOH 1N; dch kim em o quang 512 nm
- so vi dung dch chun Mg acetat 0.5% / MeOH
70

5. NH LNG BARBALOIN
5.3. Phng php DVN III (2002) p. 401

Lm m bt Nha L hi = MeOH

Chit bng nc nng (60 0C 30)

Oxy-ha + thy phn bng (FeCl3 + HCl ; BM 4 h)

Chit AQ bng Et2O

C cn, + d.dch Mg acetat 0.5% / MeOH

o Abs. 512 nm (// mu trng l MeOH)

Hm lng hydroxyanthracen (quy v barbaloin %)

quy nh : nha A. vera 28%; A. ferox 18%

71

6. TAC DUNG V CNG DUNG

6.1. Nha L hi (giu AQ)
- thng mt, tr tiu ha
- nhun, ty (kiu AQ : sung huyt, k thai . . .)
6.2. Gel l L hi (rt t AQ)
- khng khun, khng vim
- cha phng, mau lnh so
- m phm
6.3. Bt l L hi (X)
- nga v tr to bn

72

73

PHN LP ANTHRANOID
Bt r

Nhu

T R NHU

EtOH.H2O
Dch chit cn
c thu hi EtOH,

OMe

CHO

+ HCl long, Lc
3 OH

Lp ta
VLC, Si-gel /

damnacanthal

DCM

anthranoid
SKC, Si-gel /

OH
1

Benzen - DCM

CHO

3 OH

cc AQ

nor-damnacanthal
74

365

254

ND

ND

ND

365 + 254

75

TAC DUNG VA CONG DUNG

Nc sc r nhu cha au lng v cao

huyt p;
Qua c tc dng iu kinh, nhun trng,
cao huyt p;
L cha vt thng, mn nht, tr au
lng , cha l v cha st.
Xem video clip v tc dng ca cy Nhu

76