TS Nam - DL Chua Anthranoid

8/13/2019 TS Nam - DL Chua Anthranoid

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Phn 2

DC LIUCHA 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


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NOI DUNG1. nh danh thc vat & dc lieu2. Mo ta thc vat, bo phan dung3. Thanh phan hoa hoc chnhAnthranoidTannin4. Chiet xuat5. nh tnh6. nh lng

Theo DVN IITheo DVN III7. Tac dung sinh hoc Cong dung


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La


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Toan cay


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1. NH DANHai hoang gm nhieu loai thuoc chi Rheum, ho Polygonaceae

DTQ quy nh 3 loai- R. palmatum L.- R. officinale Baillon- R. tanguticum Maxim ex Balf.

DVN III quy nh dung- R. palmatum L.- R. officinale Baillon- R. palmatum officinale

palmatum : hnh ban tayofficinale : dc dung


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2. MO TACay: 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 otm nhat.Than re: rat phat trien (bo phan dung)Hoa: ngon, thng moc thanh chumQua: co 3 canh


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Hnh ngon cay mang hoa


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La va ngon hoa


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PHAN BO- Trung quoc, chau Au- Viet Nam con phai nhap

- Thu than re t cay tren 3 tuoi- Cat bo re con- Thai phien phan than re- Bao quan 1 nam mi dung

THU HAI


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BOPH N DUNGRhizoma RheiThan re a cao vo, say kho cua cac loai ai hoang- Rheum palmatum L.- Rheum officinale Baillon- Rheum palmatum officinale, ho Polygonaceae


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BO PHAN DUNGRhizoma Rhei


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1. Manh ban. Manh mo mem

3. Si

4. Calci oxalathnh cau gai

5. Hat tinh bot

Soi b t


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3. THANH PHAN HOA HOC

@. Aglycon (anthraquinon)- anthraquinon t do dang oxy hoa- anthraquinon dimer dang kh

@. Glycosid (anthraglycosid)- glycosid dang oxy hoa- glycosid dang kh (anthron, anthranol)- glycosid dang dimer

Chu yeu : anthranoid (3% - 5%) va tannin (10%, PC > PG)

khoang 0.1 0.2%

khoang 2 4%


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THANH PHAN HOA HOC@. Anthraquinon t do dang oxy hoa

O

OH OH

R6 R

R6 R3- Chrysophanol H Me- Aloe emodin H CH2OH- Rhein H COOH- Emodin OH Me- Physcion OMe Me


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THANH PHAN HOAHOC@. Glycosid vi aglycon dang oxy hoa hay dang kh- chrysophanol- Aloe emodin- Rhein- Emodin- Physcion

OH gan glucose

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


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Cu tao cua cac dimer aglyconesAnthron 1 va Anthron 2 Tao thanh

RheinAloe emodin RheinRhein Sennidin A va BSennidin CEmodin Rhein Rheidin AChrysophanol Rhein Rheidin BPhyscion Rhein Rheidin CAloe emodin Emodin Palmidin AAloe emodin Chrysophanol Palmidin BEmodin Chrysophanol Palmidin C


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Cau truc cac dimer anthronesO

O

OH OH

OHOH

R3

R3

R6

R6

Cac dimer aglycon


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Cau truc cac dimer glycosid.O

O

OH

OH

COOR

COOH

glc

O

O

glc

Cac dimer glycosid


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4. NH TNH4.1. 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 acetat4.3. Phan ng vi Pyridin MeOH4.4. Th nghiem vi thang hoa (ket hp vi Borntrager)4.5. nh tnh so sanh4.6. nh tnh phan biet


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5. NH TNH

- 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)

4.5. nh tnh so sanh


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5. NH TNHKhi 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

hRf = 50 55 70 80 95

CT

mau th T a b lan rhaponticosid

4.6. nh tnh phan biet D Phap


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6. NH LNG6.1. 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


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6. NH LNG

- 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 / 100mai hoang phai cha 2,2% anthranoid (tnh theo rhein)Mun nh lng cac anthranoid acid ta lc dch chit ethervi Na bicarbonat ;

6.2. Phng phap DVN III, 2002


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7. TAC DUNG VA CONGDUNG- Dang kh / dc lieu ti cotac 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, m t t qua gan, chu yeu : phanChuy:- 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


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- Cac vi khuan tai ruot gia catSennoside 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


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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 tythe) 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)


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MT VI BI THUC THNG DNG

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Trch ng lipid huyt cao: dung con chie t xua t a i hoa ng la m thanhvie n 0 25g moi nga y uong lu c sang sm 3 vie n x 3 tuan, kt qua tt;s bnh nhan tri glyceride va beta-lipoprotein cao t kt qu 76%;Tr chu ng trng v thc nhie t ta o bon :ai hoang : 10 - 15g, Hau phac : 8g, Ch thc :8g, sac uongMang tieu : 10g ( hoa ung) neu bung chng;Tr cha n 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 hongmi ln ung 3g, ngy 3 ln ,kim tra phn m tnh hoc dngtnh nh mi thi ung, Bnh qun thi gian cm mu l 2 ngy,


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Cassiaangustifolia(L hp)


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C 2 loi thng dng:

- Cassia angustifoliaVahl., Phan t dipn

- Cassia acutifoliaDel., Phan t dip Ai cp

Cy: nh, cao n 1 m, mc thnh bi.

L: kp lng chim chn, loiC. acutifoliac t 4 5 i l

cht,C. angustifoliac 5 8 i, nh nhn.

Hoa: mc thnh chm nch l, cnh mu vng, c 10 nhi,

c 3 nhi lp.

Qu: loi qu u dt, cha 6 8 h t

1. M T


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1. C iM THC VT

Phan t : Cassia angustifiolia Vahl. (L hp)

Cassia acutifolia Del. (L nhn)

Phan t l hp Phan t l nhn

Ngun gc Arab Phi chu

Trng nhiu n Ai cp

L, qu di, hp ngn, mp

S l cht nhiu hn t hn

Vit Nam +++


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@. Cc anthranoid dng t do (0,05 0,10%)

Rhein, aloe emodin, chrysophanol

@. Cc dimer anthranoid (2-3%):

Sennosid A, B = dirhein anthron

Sennosid C, D = rhein anthron + aloe emodin anthron

@. Cc flavonoid: kaempferol, isorhamnetin

@. Cht nha: gy au bng, tan trong cn v nc nng

nhng b ta khi ngui. Do cn ngui v lc loi

nha trc khi ung.

2. THANH PHN HA HC


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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

3. INH TNH


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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


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4. INH LNG

Phng php D Php 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 bitnng .- Tnh kt qu, bit 1 mg 1,8-diOH anthraquinon ~ 1,797 mgsennosid.


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NH LNG

bt PTDdch nc nng

dch nc acid

dch thy phn + oxy ha

dch ether ln acid, mui

dch ether cn etherKOH

mu

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

Na2CO3,(pH 7-8) + (FeCl3 + HCl,)

chit kit = Et2O

ra = H2O

o Abs. 500 nm

// dd. chun Istizin

1 mg Istizin # 1,8 mg sennosid


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TC DNG & CNG DNG

Cng dng ch yu : nhun ty

Ung: C tc dng sau 8 12 gi(tht: tc dng nhanh hn)

C ch: Kiu AQ (tng nhu ng c trn)

- kch thch tiu ha (1 2 gam l)- nhun trng (3 4 gam l)

- ty, x (5 7 gam l)

Ch :

Loib ch

tnh

a (gy au b

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

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

Chng ch nh: Kiu AQ

A


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Tc dng kch thch tiu ho, nhun v ty tu theo liu

s dng.

- Liu gip tiu ho: 1-2 g l

- Liu nhun: 3 4 g l

- Liu x: 5 7 g

Chng ch nh i vi ngi c thai, vim t cung, bng

quang.

Dng dng: thuc hm hoc thuc tht. Tuy nhin nnra cn hoc lc loi nha trc khi dng trnh au

bng.

5. TC DNG VA CNG DNG


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

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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 chnn v khi xt nghim ch s men gan SGOT v SGPT (serumglutamic oxaloacetic transaminase v serum glutamic pyruvictransaminase) tng cao hn bnh thng gp 2-5 ln lm tiu hyt bo gan.

Du hiu khi bnh khi no th ch s men gan gim. Tt c ccbnh gan sau khi ung Phan T Dip vi liu cao 12g/ln, ngyung 2 ln, b Phan T Dip vo 1 ly nc si ngm 30 pht, haynu si cho thuc thm ra tr thnh nu hng m, ung ht 1 lnmt ly, vn n ung bnh thng, khi i cu ra phn en lng tiuchy, tip tc ung cho n khi i phn d dng v phn khnglng nt na m tr li phn do, mu vng, th ngng.Khi i th men gan SGOT, SGPT gim xung bnh thng th khibnh.Ung phng bnh th liu 4g/ ngy c tc dng lc mu v gimmen gan.


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Tn khoa hc:Cassia alataL. Fabaceae

Dng cy: nh; cao 1,5 m 3 m, thn g mm, d = 10-12 cm.

L: l kp lng chim chn, di 30-40 cm, c t 8-14 i l

cht hnh trng, gc v nh l u trn.

Cm hoa: mc thnh bng di 12-14 cm, rng 5-6 cm, mang

cc hoa mu vng sm.

Qu: loi qu u, di 8-16 cm, c 2 cnh sut theo chiu dc

ca qu, bn trong c 40-60 ht.

1. M T

2 THANH PHN HO HC


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@. Trong l c cha cc dn cht anthranoid: chrysophanol,

aloe emodin, rhein, emodin.@. Trong r c 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

2. THANH PHN HO HC

(1)

O

O

OH OH

CH3

OH

O

O

OH

CH3

O-glc

OH

OMe

(2)

3 TC DNG VA CNG DNG


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L c tc dng nhun v ty tu theo liu s dng.

L cn dng cha hc lo bng cch gi nt ri xt voni b nm.

3. TC DNG VA CNG DNG


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THO QUYT MINH


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1 M T


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1. M T

Tn khoa hc:Cassia toraL. Fabaceae

Cy: nh, cao 30-90 cm, mc hoang nhiu ni trongnc.

L: kp, lng chim chn, gm 3-4 i l cht, l km

hnh si di 1 cm. L cht hnh trng ngc.

Hoa: mc k l, mu vng, c t 1-3 chic.

Qu: loi qu u hnh tr, di 12-14 cm, trong chavi chc ht


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2. B PHN DNG B phn dng l ht gi

3. THANH PHN HO HC

Ht cha ch yu l cht bo v anthranoid:

Chrysophanol Aloe emodin

Physcion Rhein

Emodin

Cc glycosid ca cc aglycon trn

A


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3. THANH PHN HO HC

Ngoi ra cn cha mt s dn cht khng thuc nhm

anthranoid nh: Rubrofusarin nor-rubrofusarin Rubrofusarin 6-gentibiosid toralacton4. CNG DNG

ng y dng cha au mt , mt m, chy nhiunc mt, qung g.

Cn dng ch nhc u, mt ng, gii nhit, b thn

Lu : khi s dng nn sao vng loi bt cht c


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Aloe vera L.

Aloe ferox Mill.Asphodelaceae

(Alloen = ng, ting Arab)


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1 M T THC VT


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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 veraL. var. chinensis (Haw.) Berger, Asphodelaceae


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Aloe spp.

Chi Aloe 180 loi 04 loi dng lm thuc.

Trong 04 loi ny, c 02 loi thng dng

Aloe vera L. = A. vulgaris Lam.

= A. barbadensis Mill. = L hi Barbade

Aloe ferox Mill.

= Bitter Aloe = L hi x Cape


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Aloe vera L. Aloe ferox Mill.


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Al


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Aloe vera

Aloe ferox


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3. CCH THU HI - CH BiN3.1. Thu hoch nha L hi

- Phng php th s

- Phng php hin i

3.2. Ch bin Bt l L hi

2. B PHN DNG

2.1. Dch c c t l = Nha L hi = ALOE2.2. Gel ca l; Bt l (sau khi thu nha)


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L HI


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x l L hi


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co ly gel


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3 THNH PHN HA HC


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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 ch l cc PS kiu gluco-mannan3.4. Khong, vitamin, enzym, lignin, saponin, sterol,

amino acid, salicylic acid.

3. THNH PHN HA HC

3 THNH PHN HA HC


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O OHOH

CH2O

H glc

Rha

aloinosid

O OMeOH

H

OH

Me

glc

homonatalosid

3. THNH PHN HA HC

O

O OHOH

CH2OH

aloe emodin

O OHOH

CH2OH

H glc

barbaloin **

4 NH TNH NHA L HI


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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)

4.5. Ph.ng vi acid periodic; acid nitric

Phn bit2 loi L hi

4 NH TNH NHA L HI


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4.2. Phn ng Schouteten

4. NH TNH NHA L HI

dch nc t

nha L hi

loi tp = bt Talc

+ bt Na borat

pha long / nc

h.quang vng sng

(di UV 365 nm)

4.3. Phn ng cng hp vi Brom

dch nc t

nha L hi

+ ddch Br2ta mu vng

4 NH TNH NHA L HI


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4.4. Phn ng Klunge (A. vera // A. ferox)

4. NH TNH NHA L HI

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 tnha L hi

+ HIO4 1%

bn (vera)hng* (ferox)

* mt sau 1 h


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

dch nc t

nha L hi

+ HNO3 nu (vera)

xanh vng (ferox)

(DVN III)

4 NH TNH NHA L HI


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4.7. Sc k (SKLM hay SKG)

Dung mi : phn cc (barbaloin >> aloe emodin)

Pht hin :

- phun, nhng 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%

4. NH TNH NHA L HI

5. NH LNG BARBALOIN


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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

5. NH LNG BARBALOIN


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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%

6. TC DNG V CNG DNG


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6. TC DNG V CNG DNG

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


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PHN LP ANTHRANOID


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PHN LP ANTHRANOID

T R NHUBt r Nhu

Dch chit cn

Lp ta

anthranoid

EtOH.H2O

c thu hi EtOH, + HCl long, Lc

VLC, Si-gel / DCM

cc AQ

SKC, Si-gel / Benzen - DCM

O

O

CHO

OH

OMe

3

21

O

O

CHO

OH

OH

12

3

damnacanthal

nor-damnacanthal

365 254365 + 254


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D

ND

D

ND

D

ND

TAC DUNG VA CONG DUNG


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Nc sc r nhu cha au lng v cao

huyt p; Qu c tc dng iu kinh, nhun trng,

cao huyt p;

L cha vt thng, mn nht, tr aulng , cha l v cha st.

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TS Nam - DL Chua Anthranoid