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MC LC
Trang LI CM N MC LC DANH MC CC K HIU, CH VIT TT DANH MC CC BNG DANH MC CC S DANH MC CC HNH i v vi vi vii
M U TNG QUAN
1. I CNG V CY MP NG 1.1 M t cy 1.2 Phn b v sinh thi 1.3 Y hc dn gian ca cy mp ng 1.3.1 R 1.3.2 Thn 1.3.3 L 1.3.4 Hoa 1.3.5 Tri 1.3.6 Ht 2. CC NGHIN CU V MP NG 2.1 Cc cng trnh nghin cu trong nc 2.1.1 Thnh phn ha hc 2.1.2 Tc dng dc l 5 5 5 6 6 6 7 7 7 7 2 2 4
2 2.2 Cc cng trnh nghin cu trn th gii 2.2.1 Thnh phn ha hc 2.2.1.1. Triterpene 2.2.1.2. Steroid 2.2.1.3. Protein 2.2.1.4. Lipid 2.2.1.5. Carbohydrate 2.2.1.6. Caroteniod 2.2.2. Mt s triterpene trong cy mp ng 2.2.2.1. Cc triterpene glycoside c c lp t ht mp ng 2.2.2.2 Cc triterpene glycoside c c lp t tri mp ng 2.2.2.3 Cc triterpene glycoside c c lp t l v dy mp ng 2.2.3. Tc dng dc l 8 8 8 9 9 9 9 10 10 10 12 16 19
THC NGHIM
1. NGUYNLIU 2. NH TNH CC HP CHT HU C TRONG TRI MP NG 2.1 Kho st s hin din ca cc hp cht alkaloid 2.1.1 Thuc th alkaloid 2.1.2 nh tnh alkaloid 2..2. Kho st s hin din ca cc hp cht flavonoid 2.2.1 Thuc th flavonoid 2.2.2 nh tnh flavonoid 2.3. Kho st s hin din ca cc hp cht anthraglycoside 2.3.1 Thuc th anthraglycoside 2.3.2 nh tnh anthraglycoside 2.4. Kho st s hin din ca cc hp cht sterol 2.4.1 Thuc th sterol 2.4.2 nh tnh sterol 23 23 24 24 24 25 25 25 25 25 25 26 26 26
3 2.5 Kho st s hin din ca cc hp cht saponin 2.5.1 Thuc th saponin 2.5.2 nh tnh saponin 2.6. Kho st s hin din ca cc hp cht ng kh 2.7. Kho st s hin din ca cc hp cht tanin 2.7.1 Thuc th tanin 2.7.2 nh tnh tanin 2.8. Kho st s hin din ca cc hp cht glycoside 2.8.1 Thuc th glycoside 2.8.2 nh tnh glycoside 3. TCH CHIT, C LP V TINH CH CC HP CHT 3.1. Thit b v ha cht 3.1.1. Thit b 3.1.2. Ha cht 3.2. Chit xut cc nhm hp cht 3.3. Phn lp v tinh ch cc hp cht 26 26 27 28 28 28 28 28 28 29 30 30 30 30 31 32
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2.1. Cht MC1 2.1.1 Kt qu phn tch tinh khit ca MC1 bng HPLC 2.1.2 Nhn danh cu trc ha hc ca MC1A v MC1B 2.1.2.1. Mu cht MC1A 2.1.2.2 . Mu cht MC1B 2.2. Hp cht MC6 2.3. Hp cht MC5
37 37 37 37 41 47 51
KT LUN
PH LC
DANH MC CC PH LC
5 NMR ppm Rf s t TLC UV -Glc : Nuclear Magnetic Resonance : Parts per million : Retention factor : Singlet (NMR) : Triplet (NMR) : Thin Layer Chromatography : Ultra Violet : -glucosidase : Chemical shift
DANH MC CC BNG
Trang Bng 2.1: Kt qu sc k ct thng Bng 3.1: Kt qu nh tnh cc hp cht hu c trong tri kh qua Bng 3.2: D liu ph 1H, 13C-NMR; DEPT v HMBC ca MC1A Bng 3.3 : D liu ph 13C-NMR v DEPT ca MC1B Bng 3.4: D liu ph 1H, 13C-NMR, DEPT v HMBC ca MC1B Bng 3.5: D liu ph 13C-NMR v DEPT ca MC6 Bng 3.6: D liu ph 1H, 13C-NMR, DEPT v HMBC ca MC6 Bng 3.7: So snh d liu ph MC6 vi ti liu 34 36 39 42 45 49 49 50
DANH MC CC S
S 2.1: Quy trnh chit xut cc nhm hp cht ca tri mp ng S 2.2: Quy trnh phn lp v tinh ch cc hp cht t tri mp ng 32 33
DANH MC CC HNH
Hnh 1.1: Cy kh qua Hnh 1.2: Dy v l kh qua Hnh 1.3: Tri kh qua Hnh 1.4: Ht kh qua Hnh 1. 5: Gin kh qua (Ph Yn) Hnh 1.6: Var. charantia L. Hnh 1.7: Var. abbreviata Ser. Hnh 2.1: Qu trnh sy nguyn liu Hnh 2.2: Sc k ct Hnh 2.3: Sc k lp mng Hnh 3.1: Tinh th MC1 Hnh 3.2: TLC ca MC1, MC1A v MC1B Hnh 3.3: TLC ca MC1A cc h gii ly khc nhau Hnh 3.4: Cng thc cu to ca MC1A Hnh 3.5: TLC ca MC1B cc h gii ly khc nhau Hnh 3.6: Cng thc cu to ca MC1B Hnh 3.7: Mu cht MC6 Hnh 3.8: TLC ca MC6 Hnh 3.9: Cng thc cu to ca MC6 Hnh 3.10: Mu cht MC5 Hnh 3.11: TLC ca MC5 3 3 3 3 3 5 5 23 30 30 37 37 38 39 42 45 48 48 51 51 51
LI C M N
Em xin gi li cm n su sc n: PGS.TS Nguyn Ngc Hnh ThS. Phng Vn Trung Ngi thy truyn t cho em nhng kin thc chuyn mn v kinh nghim nghin cu, tn tnh hng dn, ch bo em trong sut thi gian em nghin cu ti phng Ha hp cht thin nhin- Vin Cng ngh Ha hc. Khoa Cng ngh Ha- Thc phm cng Thy, C v cc bn sinh vin trng i hc Lc Hng quan tm ng vin, to mi iu kin cho em trong qu trnh hc tp v nghin cu. ThS. Phan Nht Minh, cc anh ch trong phng Ha hp cht thin nhin, cng cc anh ch nghin cu vin trng i hc Cn Th, cc bn sinh vin n lm ti nghin cu tn tnh hng dn, gp , cung cp ti liu, to iu kin gip em lm tt cng vic ca mnh. Con knh gi n Gia nh lng bit n su sc. Xin chn thnh cm n! LC HNG, thng 11 nm 2009 L Th Minh Nguyt
LI M U
Mp ng hay cn gi l kh qua (Momordica charantia L.), thuc h Bu b Cucurbitaceae) c trng nhiu nc trn th gii, c bit l nhng vng c kh hu nhit i. Vit Nam, cy c trng hu ht cc tnh t ng bng n trung du v min ni. Mp ng c v ng, tnh hn nn trong dn gian thng dng tr cc bnh mn nht, gii nhit, tr phin, thanh tm, sng mt, gim au Khoa hc ngy nay chng minh dch chit tri mp ng c kh nng c ch khi u, c tc dng h tr men gan v iu tr bnh i tho ng Hin nay bnh i tho ng l mt trong cc bnh mn tnh, gy t vong cao, ng hng th ba trn th gii sau bnh tim mch v ung th. Vit Nam, t l mc bnh ngy mt gia tng, i hi cp thit phi tm ra cc loi thuc hiu qu, c tr. Mp ng c tc dng c bit nh vy nhng hin nay vn cn rt t cng trnh nghin cu v hp cht tr bnh i tho ng. V th, chng ti thc hin nghin cu ti : Gp phn kho st thnh phn ha hc ca tri mp ng.
TNG QUAN
1. I CNG V CY MP NG
1.1. M t cy
Tn khoa hc: Momordica charantia L. H: Bu b (Cucurbitaceae) Tn nc ngoi: Bitter melon, bitter gourd (Anh), bitter apple, wild cucumber, bitter cucumber, ampalaya (Philipines), balsam pear (M), karela (n ) Tn Vit Nam: Mp ng, kh qua, lng qua, cm l chi[3] Ngoi ra n cn c nhiu tn khc nh: Mp m, chua hao, da mt, hng c nng, hng dng, b t, li qua. M t cy mp ng: [3,21] Cy mp ng thuc loi dy leo, c i sng khong mt nm. ng knh dy khong 5-10mm, dy b di 5 7m, thn mu xanh nht c gc cnh, leo c nh c nhiu tua cun, ngn c lng t. L n, nhm, mc so le, di 5-10cm, rng 4-8cm, phin l mng chia lm 5 7 thy hnh trng, mp c rng ca u, mt di l mu xanh nht hn mt trn l, gn l ni r mt di, phin l c lng ngn. Hoa mc n c k l, hoa c v hoa ci cng gc, c cung di. Hoa c c i v ng rt ngn, trng gm nm cnh mng hnh bu dc, nhy 5 ri nhau. Hoa ci c i v trng hoa ging hoa c. Trng hoa mu vng nht, ng knh khong 2cm . Tri hnh thoi, di 8 15cm, gc v u thun nhn. Mt v c nhiu u li to nh khng u. Tri khi cha chn c mu xanh hoc xanh vng nht, khi chn c mu vng hng. V th Trung Quc, mp ng cn c tn l hng dng, hng c nng. Khi chn, tri nt dn ra t u, tch ra lm ba phn l chm o ht mu bn trong .
[16]
10 Ht dt, di 13 15mm, rng 7 8mm, hnh rng nga, tht t ngt hai u. V ht cng, quanh ht c mng mu nh mng ht gc.
Hnh 1.1: Cy mp ng
Hnh 1.2: Dy v l mp ng
Hnh 1.3:Tri mp ng
Hnh 1.4: Ht mp ng
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1.3. Y hc dn gian ca cy mp ng
Hu ht cc b phn ca cy nh r, thn, l, hoa, tri, ht u c th dng lm thuc cha bnh. [4] 1.3.1 R R ti, sc nc ung, mi ngy mt thang, t 1000ml nc vi 60g r mp ng ti, sc cn 400ml, chia lm 2 3 ln ung, c th p dng cho mi dng bnh. R mp ng dng tr l, nht l amip. Ti n , dch r (cng nh l, tri) mp ng c dng tr bnh tiu ng, do c tc dng lm gim ng huyt. R mp ng cn c th tr bnh gan. [2] 1.3.2 Thn Dy mp ng c dng lm thuc cha vim xoang, chy nc mi c mi hi hoc bnh gan lm vng da. [13] 1.3.3 L L c v ng, tnh mt. n l non tr bnh nng bc trong mnh. Gi l vt nc, thm cht mui, ung tr bnh nng m man hoc tr mn nht, rm sy. Ngoi ra, l cn c th tr c rn cn, lm thuc nhun trng, h st. [2, 4]
13 1.3.4 Hoa Hoa mp ng c dng cha au d dy, l cp tnh , au mt. [4,15] 1.3.5 Tri Tri cn xanh c v ng, khi chn th t ng hn. Tri mp ng c tnh hn (mt), khng c. Tri xanh c tnh gii nhit, lm tiu m, nhun trng, b thn, nui can huyt, bt mt mi, gim stress, xoa du thn kinh, gii c, li tiu, lm bt au khp. Khi chn mp ng c tnh b thn, kin t, dng huyt, dit giun (sn, li), ng thi c tc dng lm sng mt, b tim, b mu, mt gan, rt thch hp vi nhng ngi au gan, au l lch.[22] Trung Quc, tri mp ng cn dng tr t qu tim, bnh st, kh ming, vim hng. n , dch tri mp ng c dng tr rn cn. Ngi ta cn dng bt tri mp ng hn cc vt thng (lm ko da non), tr vt lot c tnh. Thi Lan, dch tri c dng tr bnh v gan, l lch.[2] Vi tnh dit khun v chng oxi ha, tri mp ng lm da mn mng, tr mn trng c hay bnh vy nn, v ngay c vi vt thng do cn trng cn, nhim trng da. Mt khc, tri mp ng cn cung cp ngun nng lng di do v tng kh nng chu ng cho c th.[22] Ngoi cc cng dng trn, tri mp ng cn c dng tr nhiu bnh nh: Tr ho, st, kit l, d dy, au tc, i dt, ph thng do gan, mt au nhc, gii nhit, hi hp, bun phin, tm cho tr em tr rm sy, lm h ng huyt bnh nhn i tho ng type 2 (khng ph thuc insulin). [17] 1.3.6 Ht Ht c cht bo, v ng, hi ngt, tnh m, thanh nhit, gii c, gii cm, tr ho, li tiu. Ht cn cha rn cn, cha nht c sng ty, vt thng nhim trng, h st au hng v chng th thai.[13] Ti nhiu nc khc, ht mp ng c dng tr bnh i tho ng.[18, 22]
14 Ngoi ra, theo mt s nghin cu gn y cho bit cc hot cht trong ht mp ng cn c tc dng chng ung th, lm h huyt p, khng virus HIV[17]
2. CC NGHIN CU V MP NG
2.1 Cc cng trnh nghin cu trong nc
2.1.1 Thnh phn ha hc Cc tc gi Phm Vn Thanh, Phm Kim Mn, on Th Nhu, Nguyn Thng Dong, V Kim Thu, Nguyn Kim Phng v L Minh Phng ca Vin Dc liu thng k v kho st s b cc nhm hot cht chnh ca cy mp ng. Tuy nhin, cc tc gi ny cha c lp c cc hot cht c hot tnh di dng cht tinh khit cng nh cha xc nh cu trc ca cc hot cht ny, m ch nh lng theo cht G6, mt aglycon ca nhm glycoside .[14] Cc tc gi Nguyn Thanh Hng, Nguyn Ngc Hnh, Phng Vn Trung Vin cng ngh Ha hc c lp v nhn danh c hai hp cht t ht: Momordicoside A v Momordicoside B v bn hp cht t tri: Momordicoside K, Momordicoside L, 3-O[-D-glucopyranosyl]-stigmasta-5,25(27)-diene v 23-O--D-allopyranosyl 5,19epoxycucurbita-6,24-dien-3,22,23-triol 3-O--D-allopyranoside. [10] 2.1.2 Tc dng dc l Y hc c truyn v dn gian Vit Nam c nhiu kinh nghim cha bnh t mp ng, nhng ch dng nguyn liu th ban u hoc cc dng nc p, nc sc m thi. Ngy nay, trn th trng xut hin nhiu sn phm tri mp ng nhng a s dng thc phm chc nng nh tr ha tan, tr ti lc. in hnh l sn phm tr mp ng ca Vin Dc liu hay tr ti lc mp ng ca Cng ty Traphaco. Nhm tc gi Phm Vn Thanh, Phm Kim Mn, on Th Nhu v cng s sn xut ch phm Morantin t thnh phn glycoside ca tri mp ng dng to, mu trng v chng minh tc dng h ng huyt ca nhm glycoside trn th gy i tho ng thc nghim bng Alloxan. [14]
15 Cc tc gi Nguyn Th Nh, Nguyn Th Bay nghin cu tc dng h ng huyt ca mt bi thuc nam trn thc nghim lm sng, l sn phm tr ti lc m thnh phn mp ng qua chim 60%. Cc tc gi Mai Phng Mai, V Phng Nguyn cng thm d tc dng h ng huyt ca mt s bi thuc dn gian m hnh i tho ng bng streptozotocin trn chut nht, m thnh phn ca bi thuc cng c cha tri mp ng.
Triterpene saponin: Goyasaponins I, II, III. Cc triterpene khc: Momordicin, momordicinin, momordicilin. Cucurbitane triterpenoid 3, cucurbitane triterpenoid 6. -amyrin, cycloartenol, erythrodiol, gypsogenin, karounidiol, multiflorenol,
Sterol: Elasterol; lanosterol; momordenol; -sitosterol; -spinasterol; stigmasterol; stigmasta-5-ene-3,25-diol. 2.2.1.3. Protein p-insulin, v-insulin. Map-30. Momorcharin I, momorcharin II, -momorcharin, -momorcharin, -
momorcharin, -momorcharin, -momorcharin. Momordin, momordin A, momordin B. Ribosome-inactivating proteins 1, 2, 3, 4. Trypsin inhibitor mcti-I, trypsin inhibitor mcti-II, trypsin inhibitor mci-3. Cc protein khc: Alanine, -alanine, phenylanaline, arginine, asparagine, aspartic acid 2.2.1.4. Lipid Arachidic acid, capric acid, cholesterol, -elaeostearic acid, lauric acid, linoleic acid, linolenic acid, palmitic acid, palmitoleic acid, stearic acid. 2.2.1. 5. Carbohydrate D-galacturonic acid, -glucose, -glucose, inulin, mycose, pectin, trehalose, trehalose.
17 2.2.1. 6. Carotenoid -carotene, cryptoxanthin, lutein, lycopene, mutatochrome, phytofluene, rubixanthin, zeaxantin, zeinoxanthin Ngoi ra cn c cc thnh phn khc: Alkaloid: Charine, zeatin, zeatin riboside; monoterpene: p-cymene, menthol ; sesquiterpene: Nerolidol; sapogenin: Diosgenin; cc cht khong: Ca, Mg, Fe, Cu, Zn, P, N, I, F Trong nhiu nghin cu, ngi ta chng minh c rng c t nht ba nhm hp cht c tc dng lm gim lng ng huyt hoc c hot tnh khng i tho ng. l hn hp ca hai steroid glycoside gi l charantin, cc peptide ging insulin (pinsulin) v alkaloid. Cc hp cht ny ch yu tp trung tri mp ng. 2.2.2. Mt s Triterpene Glycosede c trong cy mp ng 2.2.2.1. Cc triterpene glycoside c c lp t ht mp ng [25, 26, 27,28,31,33] Momordicoside A L 3-O--gentiobioside ca cucurbit-5-en-3,22(S),23(R),24(R),25-pentaol. Cng thc chung: C42H72O15; M = 816 vC; mp = 181 187oC; []20D = +1.05o. Cng thc cu to:
OH
21 18 12 11 1 2 6" 5" 4" 13 14 15 10 5 4 5' 4' 1" 19 6 30 31 8 7 32 17 16 20 22 23
OH
24 25 26
OH OH
27
OH O O
6'
O
1'
OH
3" 2"
OH
3' 2'
HO
HO OH
OH
18 Momordicoside B -3-O--D-xylopyranosyl(14)-[-D-glucopyranosyl(16)]--D-glucopyranoside ca cucurbit -5-en-3 ,22(S),23(R),24(R), 25pentaol. Cng thc chung: C47H80O19; M = 948 vC; mp = 238 242oC; []20D= +6.15o. Cng thc cu to:
OH
21 18 12 11 1 2 13 14 15 10 5 4 19 6 30 31 8 7 32 17 16 20 22 23
OH
24 25 26
OH OH
27
OH O O
4' 1" 2"
6' 5'
O
1' 2'
OH
3"
OH
3'
HO
OH O
OH
5''' 4'''
O
1''' 2'''
OH
3'''
HO
OH