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- Bach qua*
- Dy mt*
- Cc Citrus*
- Dip c
- T mc
PHN B TRNG TROT - Moc nhiu Trung quc, Han, Nht, - cung thy chu u. - Vit Nam cung co trng (t canh, hat) - Cy 3 tui se cho hoa (hoa Hoe)
> 90%
< 10%
6
1. Hoa hoe
2. Cc b phn khc a. L : b. vo qua : Flavonoid (6.6%) # 4.7% Rutin Flavonoid (10.5%) # 4.3% Rutin
OH HO O O OH O Rutinose OH
= Rutoside
(C27H30O16 = 610.51)
u tin: t Ruta graveolens. Hin nay: chu yu t - nu Hoe - Bach an (Sophora japonica). (E. macrorhyncha).
- Bt tinh th hinh kim nho, vang luc, khng mui vi, - sy 96OC : ngm 3H2O; 110OC 12h/10 mmHg khan - Di nh sng va khng khi - Rutin khan : 125OC se 196OC se bi oxy-hoa nu. mau nu, hoa deo; huy 215OC
- d tan /
- tng mau vang / dung dich kim loang, - cho mau o m vi phan ng cyanidin, - cho mau xanh luc (ri nu) vi dung dich FeCl3, - pht quang vang cam hi nu / UV 366 nm.
OH HO O O OH O Rutinose
13
OH
3. hat phn co 3 l ny mm
1. Phan ng mau
bt hoa Hoe
EtOH 95%, un, loc
dich chit cn
NaOH loang FeCl3 loang Mg* / HCl
xanh luc nu
mau o m
15
- dung mi :
EtOAc ForOH H2O (8 : 1 : 1)
(100 : 17 : 13)
(4 : 1 : 5; )
1. Phng php UV-Vis Bit = 362.5 nm; Rutin co 2. Phng php so mau - sau phan ng Cyanidin (Vis) - sau phan ng vi AlCl3 (UV 365 nm) 3. Phng php cn - chit rutin = EtOH nong, thuy phn vi H2SO4
1% E 1cm
= 325
Abs.
A1
325
A2
200
250
300
350
400 nm
bit An
Cn
18
nu hoa Hoe
HCl 0.5% EtOH 95%
dich chit cn
thu hi cn
+ H2SO4 2%
tua quercetin
cn
quercetin %
rutin %
19
Ct:
Pha ng: Detector: Ct :
Pha ng:
Detector:
Detector UV 365 nm
10
15
20
25 phut
(1) rutin,
(2) quercetin-3-glc,
(3) quercitrin,
(4) myricetin,
(7) apigenin,
(5) luteolin,
(8) kaempferol
(6) quercetin,
(9) isorhamnetin.
21
2984
OH HO O O OH O Rutinose OH
1466
1493
1656 1605 1202 1360 1295 22
3418
303
H+
465
quercetin
glc
rha
146
611 = [M+H]+
(162+146)
146
[quercetin+H]+
50%
162
303
100
200
300
400
500
600
m/z
23
Ph
13C-NMR
cua Rutin
HO O
OH OH O Rutinose
3 5 4 4
quercetin (15 C)
6
OH
10
2 C/rutinose
5 2 6 8
rutinose
ppm
24
- lam bn va giam tinh thm cua mao mach, hng cu - chng co tht, giam trng lc c tim. - phong chng x va ng mach, - tri xut huyt (chay mu cam, bng huyt, ho ra mu). - tri cc ri loan v vn mach (tri, chn nng, di cam u chi, au nhc chi, phu chi,
T Rutin cc d tan co tc dung tri liu hn: - trihydroxyethyl-rutosid (Troxerutin*, Solurutin*), - morpholylethyl-rutosid, sulforutin, ethoxazo-rutosid...
C2H4OH O O O OH O
O O Rutinose
C2H4OH C2H4OH
trihydroxyethyl-rutosid
26
Artichaut
27
28
a phi / sy
29
# 1.000.000 tn (2005)
Arg. 100.000 tn (10%)
Chu u : 85%. Trong o, Italia 500.000 tn (50%) Spain 300.000 tn (30%) Php 50.000 tn (05%).
Trng bng chi non. Thu hoach l sau khi hi cum hoa
(nhng khi cha ra hoa, thu hoach l tt nht). L mong nc : Trnh u ng. Cn loai bo sng l, ch gi phin l (l non tt hn l gia). Sau o:
1. Cc acid (#11 hp cht) acid 1,5-dicaffeoyl-quinic acid 1,3-dicaffeoyl-quinic = (1 tin cht * cua cynarin) = cynarin ** (0.5%)
acid 3-caffeoyl-quinic
acid 4-caffeoyl-quinic acid 5-caffeoyl-quinic
2. Cc Flavonoid (# 8 hp cht)
- Cynarosid
- Scolymosid
(Luteolin 7-O-glc)
(Luteolin 7-O-rut)
- Cynarotriosid (Luteolin 7-O-rut; 4-O-glc) - Narirutin 3. Cc thanh phn khc - phytosterol (-sitosterol, stigmasterol) - triterpenoid (taraxerol, cynarogenin)
- cht ng (cynaropicrin)
33
HO
5
3 OH 6
2 1 COOH
OH
OH
acid quinic
3 4 HO 5 OH
COOH 1
OH
6 OH
Caffeoyl
4
Caffeoyl
HO COOH
HO
5
3 O 6
COOH
1
HO
OH
Caffeoyl
cynarin
= acid 1,3-dicaffeoyl-quinic
34
Caffeoyl
4
HO
5
3 O 6
COOH
1
OH
Caffeoyl
cynarin
OH OH
dy ni depsid
CO
4
HO
5
3 O 6
COOH
1
OH
OH CO OH
35
dy ni depsid
Dich cn nc
thu hi cn
Dich nc
lc EtOAc
cn - nc
L a x
Dich EtOAc
ng kh
dit men
L Artis (4oC)
Cn EtOAc
sc k
cc Polyphenol
36
Phng php Fratianni (2007) (Dung chun bi mu inh lng, mu th sinh hoc) L Artis ng lanh c ngm 1 gi vi 5 V dung mi
37
2.5% - 5% cynarin
15% acid chlorogenic tinh theo acid chlorogenic (HPLC) Thng bi trn ng mach nha hay maltose Trn thc t, ngoai cc tiu chun / DVN; cao Artis thng c b sung tiu chun inh tinh bng HPLC. Sc mu th phai cho cc peak # cc cht chun 13% - 18% acid caffeyolquinic
38
L Artis kh (50 g)
MetOH 70% (2 x 1000 ml)
Dich chit cn **
lc vi CHCl3 Ly lp nc
Dich chit nc
SKC RP-18, thu 50 ph.oan
Ph.oan (02)
P. (03 16)
P. (44 - 46)
acid chlorogenic
luteolin 7-rutosid
cynarosid
cynarin
39
manh biu bi phin l gm nhng t bao a gic, mang l khi & rt nhiu lng che ch nhiu khi nha nu, kich thc thay i
cn cn 96% +
(10OC x 20 phut)
NaOH 10%
mau hng cnh sen
40
polyphenol +
polyphenol +
FeCl3 1%
kali fericyanid 1% (thth Barton)
mau xanh
41
42
: Si-gel F 254 / Si-gel G : BuOAc ForOH H2O (14 : 5 : 5) : NaNO2 / NaOH (cynarin mau hng)
: HCl 0.1N; chiu khai trin: : thuc th Barton : Rf ~ 0.30-0.35 (mau xanh)
43
a ph c
AcOH + H2SO4
dung
ch
MeOH
inh lng polyphenol toan phn Dung ph.php Folin-Ciocalteu, tao mau xanh, so mau, tinh theo quercetin hay catechin.
inh lng polyphenol toan phn (Folin Ciocalteu) Trn (800 l nc) + (50 l th.th FC) + (10-50 l mu) Sau 1 va trc 8, thm 100 l dung dich Na2CO3 20%, b sung nc va u 1 ml. Trn u. U 2 gi, o Abs. 760 nm. Lam 3 ln lp lai. So snh vi ng cong chun cua quercetin / catechin.
rutin
Tc dung chinh
li mt, thng mt; tr tiu ho
49
50
Ngm nc, u mm, xt lt ri phi hay sy kh. Con ch thanh: T u hoang cm : tm ru, sao qua, phi sy kh Hoang cm thn : sao chy xem, phun nc, phi sy kh
baicalein,
Chu yu la cc Flavonoid
baicalin
scutellarein
HO HO OH O O
baicalein
OH HO HO OH O
OH
OH OMe HO
wogonin
O
glcA
O HO OH
glcA
O HO
OH
scutellarin
baicalin
53
Dich chit EtOH + dd. Chi acetat Dich chit EtOH + Mg** / HCl
luc xm
nu tia
54
Dc in Trung quc, DVN III: Dung phng php quang ph UV-Vis : Dich chit MeOH / EtOH, o quang 279 1 nm tinh theo baicalin (E 1 = 673) 1
55
Khng khun, ha nhit Tng co bop, lam chm nhip tim. Giam co tht c trn rut.
56
57
Thn gia
59
1. Cc Flavonoid
Chu yu: sinensetin, eupatorin, tetramethyl-scutellarein (~ 10 cht thuc nhom polymethoxy-flavon (PMF) Ngoai ra con cc glycosid cua kaempferol, quercetin
3. Cc diterpenoid (> 50 cht) - cc orthosiphol, neo-orthosiphol, seco-orthosiphol - cc orthosiphonon, neo-orthosiphonon - cc staminol, nor-staminol, nor-staminon - cc staminolacton, nor-staminolacton - cc siphonol 4. Cc nhom hp cht khc - triterpenoid (acid oleanolic, ursolic, betunilic)
OMe OMe
MeO MeO OMe O O
OMe
eupatorin
Lu :
sinensetin
tetramethyl-scutellarein
: dich CHCl3 cua cy Ru meo : Si-gel G (sy 120OC x 1 h) : toluen ethyl acetat aceton acid formic (5 : 2 : 2 : 1) : ac. boric 10% ac. oxalic 10% (2 : 1) +
Kt qua
: co 6 vt co mau
hng vang
366 nm
xanh l hng
63
bt cy Ru meo
Dich nc m c
Dich n-BuOH
Cn n-BuOH / MeOH
64
DVN III, 2002: khng co ch tiu inh lng hoat cht / cy Ru meo ch co ch tiu ham lng cht chit c trong 2 dmi :
66
67
Sc t o
Hoat huyt, tri chng huyt khi (nghen mach), Tri chng au tht ngc, hep mach vanh. Lam tng co bop c trn (t cung . . .) K thai !!! Lam thuc iu kinh; cha chng b kinh, au kinh
70
OH
O HO
glc O
OH
glc
OH
7-glucosid luteolin
HO HO glc
carthamon** (chalcon)
glc O HO OH OH OH
OH
carthamin** (bis-chalcon)
71
Dy leo ln, dai # 10 m, thng moc thanh bui ln. L kep lng chim le, phin l ln, khi non: mm, vang luc
O
12
A
11
D
1
O5
rotenon*
4 3
sumatrol elliptinol
B
2
O E
D
O
1
OMe OMe
rotenon (4 8% / r)
74
Rotenon la 1 isoflavonoid kem phn cc : tan / dmhc kpc > EtOH > nc (/nc : T = 1.6 ppm) Rotenon kem bn / nh sng, khng khi. Rotenon rt kem bn / kim, d.dich Oxy-ho (KMnO4) rotenon H2SO4 vang cam bt NaNO2 mau tim xanh kO bn
NH4OH
75
Bt r Thuc c CHCl3 Cn CHCl3 CCl4 phc [Rotenon CCl4] EtOH 96% si Rotenon / EtOH lanh, thu tinh th Rotenon : cn tinh R%
76
Xc inh nng ti thiu lam cho c mt thng bng. Xc inh % rui bi cht khi tip xuc vi dd. Rotenon
Xut x
Mi trng
Artemia salina
Artemia salina
79
Artemia salina
80
81
82
Cy Cuc gai (Silybum marianum, Asteraceae) co 1-2 nm, cao 0.2 1.5 m, moc hoang va trng nhiu chu u, t lu a c dung lam thuc bao v gan. a di thc vao VN (2000, Trai dc liu Lm ng). B phn dung : Qua (Semen Silibi). Hoat cht chinh : Silymarin = hn hp 3 flavolignan (silybin + silychrystin + silydianin) Silymarin: antioxidant, bao v gan, phuc hi gan, cha cc chng bnh v gan mt (LEGALON !)
83
O OH
Silybin
OH
(C25H22O10.H2O; M = 500)
OMe OH
85
86
87
c thc vt, la loai duy nht / Ginkgoaceae con sot lai c coi la hoa thach sng. cy ln; cy c & ci ring bit l co 2 thuy c bit (biloba) cy ci mi cho qua (Ngn hanh, Bach qua) moc nhiu Trung quc, Nht, chu u.
- sesquiterpen lacton
- diterpen lacton
(bilobalid)
(cc ginkgolid A, B, C, M, J)
- flavonoid
- tannin
(gallocatechin, epigallocatechin)
89
Cht chun : rutin, quercitrin, quercetin, kaempferol va isorhamnetin Detector : PDA (350 nm).
90
rutin 8.94
91
Hat Bach qua va l Bach qua co tc dung - antioxidant; bao v gan, phuc hi chc nng gan - tri thiu nng tun hoan nao, ri loan tp tinh / ngi gia - lam bn thanh mach; cha tri
92
93
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95
96
97
98
99
100
101
102
103
104
105
nc ta cc cy thuc chi Citrus c trng cc ia phng sau: Phu tho, Ha giang, Ha tinh, Hu, Bin hoa, My tho, Cn th, Bn tre, Trn th gii, Citrus c trng cc nc chu : Trung quc, Nht, Han quc, Indonesia, Malaysia, Thi
Ngoai tinh du/vo qua ngoai (vi limonen la thanh phn chinh), carotenoid, coumarin, vitamin C, acid hu c (a. citric) va pectin, vo qua va dich qua Citrus con cha nhiu
flavonoid.
Phn ln cc flavonoid cua chi Citrus thuc nhom flavanon:
107
Bi:
@. Flavanon glycosid
Naringin (naringenin-7-O-neohesperidosid) Naringin4'glucosid
Naringin6"malonat
Neoeriocitrin (eriodictyol7Oneohesperidiosid) Neohesperidin (hesperetin7Oneohesperidiosid) Hesperidin (hesperetin7Orutinosid) Poncerin (isosakuranetin7Oneohesperidiosid)
@. Flavon glycosid
Luteolin7Oneohesperidosid Rhoifolin (apigenin7Oneohesperidosid)
108
Cam
@. Flavanon glycosid
Hesperidin (hesperetin7Orutinosid) Didymin (isosakuranetin7Orutinosid) Eriocitrin (eriodictyol7Orutinosid) Narirutin (naringenin7Orutinosid)
@. Flavon glycosid
Diosmin (diosmetin7Orutinosid) Isorhoifolin (apiginin7Orutinosid) Rutin (quercetin3Orutinosid)
@. Cglycosylflavon
Diosmetin8glucosid Vitexin2"xylosid
109
Qut
@. Flavanon aglycon
Citromitin 5ODesmethylcitromitin
@. Flavanon glycosid
Hesperidin, Didymin, Narirutin, Neoeriocitrin, Neohesperidin
@. Flavon aglycon
Auranetin 5ODesmethylnobiletin 5,4'Dihydroxy6,7,8,3'tetramethoxyflavon 3,5,6,7,8,3',4'Heptamethoxyflavon 5Hydroxyauranetin Nobiletin, Tangeritin, sinensetin, Xanthomicrol
@. Flavon glycosid
Diosmin, Isorhoifolin, Rhoifolin
110
Chanh
Eriocitrin (eriodictyol7Orutinosid)
Hesperidin (hesperetin7Orutinosid)
Diosmin (diosmetin7Orutinosid)
Tc
3,5-Di-C--glucopyranosylphloretin Tangeretin, Nobiletin
111
Dang flavonoid toan phn phi hp vi vit. C co tc dung lam bn thanh mach, chng xut huyt di da. Diosmin + hesperidin (= Daflon) c dung cha ri loan tun hoan tinh mach, gian tinh mach, tri. Naringin c dung trong nhan khoa cha sung huyt kt mac, ri loan tun hoan vong mac. Naringenin c dung cha loet da day. Cc polymethoxyflavon (tangeretin, nobiletin,) co tc dung khng vim va khng ung th kh manh trn cc m hinh thc nghim.
112
* The grapefruit flavonoid naringenin as a Hepatitis C virus therapy : efficacy, mechanism and delivery
Naringenin is a flavonoid that contributes to the taste of grapefruit and has a bioactive effect as an antioxidant, antiinflammatory, carbohydrate metabolism promoter, free radical scavenger and an immune system builder. In addition to being useful in lowering LDL and vLTL (the bad cholesterols, Naringenin has also been shown to reduce the production of the Hepatitis C Virus in infected hepatocytes (liver cells).
113
* A study published in the journal Hepatology in June, 2008, reported that Stimulation with naringenin reduces HCV secretion in infected cells by 80% by inhibiting the secretion of vLDL.
* Citrus unshiu peel and its active ingredient nobiletin exhibit anti-hepatitis C activity.
treatment on high cholesterol diet-induced blood circulatory disorders, obesity and hyperlipidemia. * Grapefruit Compound (naringenin) may help combat Hepatitis C infection
114
* Grapefruit fights hepatitis C * Naringenin compound in Grapefruit Inhibits HCV Replication in Laboratory Study * HCV is bound to very low-density lipoprotein (vLDL, a socalled bad cholesterol) when it is secreted from liver cells and that the viral secretion required to pass infection to other cells may be blocked by the common flavonoid naringenin. * The hepatitis C virus is infected patients while lipoprotein (vLDL). The could be used to block circulating viral titer. actively secreted by the liver of bound to very low density grapefruit flavonoid naringenin vLDL secretion and lower the
115