viện hàn lâm khoa học công nghệ việt nam Viện công nghệ sinh học NGUYễN XUÂN CƯờNG NGHIấN CU HOT TNH SINH HC V THNH PHN HểA HC CA MT S LOI THUC CHI FICUS VIT NAM LUN N TIN S SINH HC Hà nội - 2014 VIN HN LM KHOA HC V CễNG NGH VIT NAM VIN CễNG NGH SINH HC NGUYN XUN CNG NGHIấN CU HOT TNH SINH HC V THNH PHN HểA HC CA MT S LOI THUC CHI FICUS VIT NAM Chuyờn ngnh: Húa sinh hc Mó s: 62 42 01 16 LUN N TIN S SINH HC Ngi hng dn khoa hc: GS.TS Trng Nam Hi Vin Cụng ngh sinh hc PGS.TS Phan Vn Kim Vin Húa sinh bin H Ni, 2014 -i- LI CM N Lun ỏn ny c thc hin ti Phũng Nghiờn cu cu trỳc, Vin Húa sinh Bin v Phũng K thut Di truyn, Vin Cụng ngh sinh hc, Vin Hn lõm Khoa hc v Cụng ngh Vit Nam, vi s h tr kinh phớ ca ti nghiờn cu c bn c ti tr bi Qu phỏt trin Khoa hc v Cụng ngh Quc gia - NAFOSTED (mó s: 104.01.31.09) Tụi xin trõn trng cm n GS TS Trng Nam Hi, Vin Cụng ngh sinh hc, Vin Hn lõm Khoa hc v Cụng ngh Vit Nam, PGS TS Phan Vn Kim, GS TS Chõu Vn Minh, Vin Hoỏ sinh bin v GS TS Kim Young Ho, i hc Dc, i hc Quc gia Chungnam, Hn Quc ó tn tỡnh hng dn, ch bo quỏ trỡnh thc hin Lun ỏn ng thi tụi xin trõn trng cm n PGS TS Ninh Khc Bn, Phũng Ti nguyờn Sinh vt, Vin Húa sinh bin ó giỳp giỏm nh loi cỏc mu thc vt Tụi cng xin chõn thnh cm n Ban lónh o Vin Húa sinh bin v Vin Cụng ngh sinh hc, cỏc cỏn b Phũng Nghiờn cu cu trỳc, Phũng Dc liu bin, Vin Hoỏ sinh bin, v Phũng K thut Di truyn, Vin Cụng ngh sinh hc, Vin Hn lõm Khoa hc v Cụng ngh Vit Nam ó to iu kin thun li v tn tỡnh giỳp tụi sut thi gian thc hin lun ỏn Cui cựng tụi xin by t lũng bit n i vi nhng ngi thõn gia ỡnh, ng nghip v bn bố ó luụn ng h, ng viờn tụi sut thi gian qua tụi cú th hon thnh tt cụng vic nghiờn cu ca mỡnh H Ni, ngy thỏng nm 2014 Nguyn Xuõn Cng -ii- LI CAM OAN Tụi xin cam oan: õy l cụng trỡnh nghiờn cu ca tụi v mt s kt qu cựng cng tỏc vi cỏc cng s khỏc Cỏc s liu v kt qu trỡnh by lun ỏn l trung thc, mt phn ó c cụng b trờn khoa hc chuyờn ngnh quc t v quc gia v ó c s ng ý ca cỏc ng tỏc gi Phn cũn li cha c cụng b bt c cụng trỡnh no khỏc H Ni, ngy thỏng nm 2014 Tỏc gi Nguyn Xuõn Cng -iii- MC LC Trang M U CHNG TNG QUAN VN NGHIấN CU 1.1 S LC V CHI SUNG (FICUS L.) 1.2 CC NGHIấN CU HOT TNH SINH HC CHI SUNG (FICUS L.) 1.2.1 Cỏc nghiờn cu trờn th gii 1.2.2 Cỏc nghiờn cu nc 1.3 CY GA F MICROCARPA 10 1.3.1 Mụ t, phõn b v sinh thỏi 10 1.3.2 Cụng dng v hot tớnh sinh hc 11 1.3.3 Thnh phn cỏc hp cht trao i th cp ó c nghiờn cu 15 1.4 CY A BP F ELASTICA 25 1.4.1 Mụ t, phõn b v sinh thỏi 25 1.4.2 Cụng dng, hot tớnh sinh hc v thnh phn húa hc 25 1.5 CY A LễNG F DRUPACEA 26 1.5.1 Mụ t, phõn b v sinh thỏi 26 1.5.2 Cụng dng, hot tớnh sinh hc v thnh phn húa hc 26 1.6 CY GO F CALLOSA 26 1.7 S ễXI HểA V GC T DO 27 1.7.1 Bn cht quỏ trỡnh ụxi húa 27 1.7.2 H thng cỏc cht chng ụxi húa ca c th 34 1.8 BNH TIU NG V HOT TNH C CH ENZYM -GLUCOSIDASE 38 1.8.1 Bnh tiu ng 38 1.8.2 Hot tớnh c ch enzym -glucosidase 40 1.9 MT S PHNG PHP PH CNG HNG T HT NHN TRONG 43 XC NH CU TRC HểA HC CA CC HP CHT TRAO I TH CP CHNG VT LIU V PHNG PHP NGHIấN CU 46 2.1 VT LIU NGHIấN CU 46 -iv2.1.1 Cõy Ga Ficus microcarpa 46 2.1.2 Cõy a bỳp Ficus elastica 46 2.1.3 Cõy Go Ficus callosa 47 2.1.4 Cõy a lụng Ficus drupacea 47 2.2 PHNG PHP NGHIấN CU 47 2.2.1 Phng phỏp chit xut cỏc hp cht trao i th cp 47 2.2.2 Phng phỏp phõn lp cỏc hp cht trao i th cp 48 2.2.3 Phng phỏp xỏc nh cu trỳc cỏc hp cht trao i th cp 58 2.2.4 Phng phỏp ỏnh giỏ hot tớnh chng ụxy húa 59 2.2.5 Phng phỏp ỏnh giỏ hot tớnh khỏng enzym -glucosidase 61 CHNG KT QU NGHIấN CU 62 3.1 KT QU THU THP CC LOI FICUS 62 3.2 KT QU PHN LP CC HP CHT TRAO I TH CP 64 3.2.1 Hng s vt lý v d kin ph ca cỏc hp cht trao i th cp t cõy 64 Ga F microcarpa 3.2.2 Hng s vt lý v d kin ph ca cỏc hp cht trao i th cp t cõy a 69 bỳp F elastica 3.2.3 Hng s vt lý v d kin ph ca cỏc hp cht trao i th cp t cõy 74 Go F callosa 3.2.4 Hng s vt lý v d kin ph ca cỏc hp cht trao i th cp t cõy a 79 lụng F drupacea 3.3 KT QU NH GI HOT TNH CHNG ễXI HểA 3.3.2 Kt qu ỏnh giỏ hot tớnh chng ụxi húa ca cỏc cht trao i th cp t 84 84 cõy Ga F microcarpa 3.3.2 Kt qu ỏnh giỏ hot tớnh chng ụxi húa ca cỏc cht trao i th cp t 85 cõy a bỳp F elastica 3.3.3 Kt qu ỏnh giỏ hot tớnh chng ụxi húa ca cỏc cht trao i th cp t 87 cõy Go F callosa 3.4 KT QU NH GI HOT TNH KHNG ENZYM -GLUCOSIDASE 88 CHNG BN LUN KT QU 89 4.1 BN LUN XC NH CU TRC HểA HC CA CC HP CHT 89 -vTRAO I TH CP 4.1.1 Bn lun xỏc nh cu trỳc húa hc cỏc hp cht trao i th cp phõn lp 89 c t cõy Ga F microcarpa 4.1.2 Bn lun xỏc nh cu trỳc húa hc cỏc hp cht trao i th cp phõn lp 96 c t cõy a bỳp F elastica 4.1.3 Bn lun xỏc nh cu trỳc húa hc cỏc hp cht trao i th cp phõn lp 102 c t cõy Go F callosa 4.1.4 Bn lun xỏc nh cu trỳc húa hc cỏc hp cht trao i th cp phõn lp 105 c t cõy a lụng F drupacea 4.2 BN LUN KT QU NH GI HOT TNH SINH HC 110 4.2.1 Bn lun kt qu ỏnh giỏ hot tớnh chng ụxi húa 110 4.2.2 Bn lun kt qu ỏnh giỏ hot tớnh khỏng enzym -glucosidase 114 KT LUN V KIN NGH 117 DANH MC CC CễNG B CA TC GI Cể LIấN QUAN N TI 119 LUN N TểM TT KT QU THC HIN LUN N BNG TING ANH 121 TI LIU THAM KHO 125 PH LC 143 -vi- NHNG CH VIT TT 13 C NMR Ph cng hng t ht nhõn cacbon 13 Carbon-13 Nuclear Magnetic Resonance Spectroscopy H NMR Ph cng hng t ht nhõn proton Proton Magnetic Resonance Spectroscopy COSY H-1H Chemical Shift Correlation Spectroscopy 2D-NMR Ph cng hng t ht nhõn hai chiu Two-Dimensional NMR CC Sc ký ct Column Chromatography DEPT Distortionless Enhancement by Polarisation Transfer HMBC Heteronuclear Multiple Bond Connectivity HSQC Heteronuclear Single Quantum Coherence IR Ph hng ngoi Infrared Spectroscopy Me Nhúm methyl MS Ph lng Mass Spectroscopy NOESY Nuclear Overhauser Effect Spectroscopy ORAC Oxygen radical absorbance capacity TLC Sc ký lp mng Thin Layer Chromatography mp Melting point im chy -viiDANH MC CC HèNH Trang Hỡnh 1.1 Cu trỳc húa hc ca cỏc hp cht - 17 16 Hỡnh 1.2 Cu trỳc húa hc ca cỏc hp cht 18 - 40 17 Hỡnh 1.3 Cu trỳc húa hc ca cỏc hp cht 41 - 54 18 Hỡnh 1.4 Cu trỳc húa hc ca cỏc hp cht 55 - 65 20 Hỡnh 1.5 Cu trỳc húa hc ca cỏc hp cht 66 - 76 21 Hỡnh 1.6 Cu trỳc húa hc ca cỏc hp cht 77 - 87 22 Hỡnh 1.7 Cu trỳc húa hc ca cỏc hp cht 88 -98 23 Hỡnh 1.8 Cu trỳc húa hc ca cỏc hp cht 99 -112 24 Hỡnh 1.9 Dng hot ng ca nit v ụxi tham gia vo hin tng 32 stress ụxi húa Hỡnh 1.10 Nhng trng thỏi bnh lý chớnh liờn quan mt thit n gc 33 t Hỡnh 2.1 Cõy Ga F microcarpa 46 Hỡnh 2.2 Cõy a bỳp - F elastica 46 Hỡnh 2.3 Cõy Go - F callosa 47 Hỡnh 2.4 Cõy a lụng - F drupacea 47 Hỡnh 2.5 S chit phõn on mu cõy Go - F Callosa 49 v phõn lp cỏc hp cht t cn chit CHCl3 v EtOAc Hỡnh 2.6 S phõn lp cỏc hp cht t lp nc 50 Hỡnh 2.7 S chit phõn on mu cõy a lụng - F drupacea v 52 phõn lp cỏc hp cht t cn chit n-hexane Hỡnh 2.8 S phõn lp cỏc hp cht t lp nc 53 -viii- Hỡnh 2.9 S chit phõn on v phõn lp cỏc cht t cõy a bỳp 54 - F elastica Hỡnh 2.10 S chit phõn on mu cõy Ga - F microcarpa v 56 phõn lp cỏc hp cht t cn chit CHCl3 v EtOAc Hỡnh 2.11 S phõn lp cỏc hp cht t lp nc 57 Hỡnh 4.1 Ph 1H-NMR ca hp cht FM1 89 Hỡnh 4.2 Cu trỳc húa hc ca hp cht FM1 90 Hỡnh 4.3 Ph 13C-NMR ca hp cht 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QUAN VN NGHIấN CU 1.1 S LC V CHI SUNG (FICUS L.) Chi Sung (Ficus L.) l mt chi ln trong h Dõu tm (Moraceae), gm cỏc cõy g ln, g nh, bi v c dõy leo, phõn b rng rói khp cỏc vựng nhit i Nam v Bc bỏn cu Ngi ta c tớnh cú khong 1000 loi thuc chi ny phõn b cỏc ni trờn th gii Cỏc nc vựng ụng Nam v Nam chõu ỏ l ni tp trung nhiu loi nht Vit Nam hin cha cú nghiờn cu y v chi Sung (Ficus L.) Phm Hong H ó nghiờn... Hot tớnh chng oxy húa ca cỏc dch chit cõy Ga cựng vi 11 mt s hp cht v hm lng tng cỏc hp cht phenol trong cỏc cn chit Bng 1.2 Hot tớnh khỏng khun ca cỏc dch chit cõy Ga v 13 ampicillin Bng 1.3 Hot tớnh chng oxy húa ca cỏc dch chit r khớ sinh cõy 13 Ga cựng vi mt s hp cht v hm lng tng cỏc hp cht phenol trong cỏc cn chit Bng 1.4 Hot tớnh khỏng khun ca cỏc dch chit ca r khớ sinh cõy 14 Ga v ampicillin Bng... trỏi xoan Qu phc hỡnh cu, khi chớn mu vng Mựa hoa qu: thỏng 9-12 1.2 CC NGHIấN CU HOT TNH SINH HC CHI SUNG (FICUS L.) 1.2.1 Cỏc nghiờn cu trờn th gii Cỏc nghiờn cu v húa hc v mi liờn h vi hot ng sinh- dc hc ca cỏc loi thuc chi Sung (Ficus L.) cng ó c thc hin trong khong 50 nm gn -6õy Nhỡn chung, cỏc loi thuc chi Sung (Ficus L.) thng cú cỏc nhúm hp cht steroid, flavonoid, cỏc triterpene, saponin, megastigman,... khỏng sinh, chng nm, chng kớ sinh trựng ca dch chit mt s loi thuc chi Sung (Ficus L.) cng ó c nghiờn cu Dch chit v cõy F asperifolia ó c s dng th nghim hot tớnh khỏng vi sinh vt kim nh l Staphylococcus aureus, B subtilis, Micrococcus flavus, E coli, Pseudomonas aeruginosa v cỏc dũng khỏng S aureus l SA1199B, RN4220 v XU212 Thờm vo ú, hot ng chng ụxi húa vi th nghim nguyờn bo si trờn da ca dch chit... trong c th hn so vi cỏc dc phm tng hp -2Mc dự Ficus l mt chi ln, c cỏc nh khoa hc trờn th gii quan tõm nghiờn cu v th hin nhiu hot tớnh sinh hc quý bỏu, nhng nc ta, vn cha cú nhiu nghiờn cu mang tớnh h thng to ra c s khoa hc phc v lõu di Xut phỏt t thc t ú, chỳng tụi ó thc hin ti "Nghiờn cu hot tớnh sinh hc v thnh phn húa hc mt s loi thuc chi Ficus Vit Nam" , vi mc tiờu v ni dung nghiờn cu sau: Mc... (n = 3) Cỏc cn chit c th nng 200 àg/a, khỏng sinh appicillin th 1 àg/a Cỏc nghiờn cu tip theo ca nhúm tỏc gi Ao Changwei v hot tớnh chng ụxi húa v khỏng khun ca cỏc cn chit ca r khớ sinh cõy Ga cho thy: Phõn on chit ethyl acetate cú cha hm lng cỏc hp cht phenol cao nht v cng th hin hot tớnh chng ụxi húa cao nht (Bng 1.3) Ngoi ra, cỏc dch chit cú hm lng cỏc hp cht phenol cao (dch chit ethyl acetate,... monotecpen, ficusic acid (99) v hai hp cht phenol mi, ficusol (100) v ficuglucoside (101) (Hỡnh 1.8), c phõn lp v xỏc nh cu trỳc t dch chit methanol ca g cõy Ga (Li, Kuo, 1998) Tip theo, mt hp cht apocarotenoid, ficusone (102) v hai dn xut g-lacton mi, ficuspirolide (103) v ficusolide (104), cựng vi 4,5-dihydroblumenol A (105) tip tc c hai tỏc gi ny cụng b vo nm 1999 (Kuo, Li, 1999) v mt g-lacton mi, ficuspirolide... polymorph Mi giỏ tr trong bng c th hin bng tr s trung bỡnh sai s chun (n = 2) Cỏc cn chit c th nng 400 àg/a, khỏng sinh appicillin th 1 àg/a Bng 1.3 Hot tớnh chng ụxi húa ca cỏc dch chit r khớ sinh cõy Ga cựng vi mt s hp cht v hm lng tng cỏc hp cht phenol trong cỏc cn chit (Ao et al., 2009) Hm lng tng cỏc hp EC50 (mg/ml) Dch chit Methanol Hexan DPPH 6,8 0,1 ABTS+ 5,6 0,1 173,0 5,8 75,1 0,8 PMS- cht... nghiờn cu theo hng khỏng vi sinh vt Cỏc nghiờn cu v tỏc dng khỏng vi sinh vt ca cỏc loi Ficus c cỏc nh khoa hc quan tõm nghiờn cu t khỏ sm Nm 1990, cỏc nh khoa hc Thy S phỏt hin dch chit metanol ca cõy F spetica th hin hot tớnh khỏng khun -8v khỏng nm mnh Cỏc nghiờn cu thnh phn húa hc theo nh hng hot tớnh sinh hc t cõy F septica ca nhúm nghiờn cu ny ó xỏc nh c hai hp cht alkanoid l Ficuseptine v antofine... et al., 2010) (+)(2R,3S) afzelechin, (-)(2R,3R) epiafzelechin th hin hot tớnh khỏng virut HSV1 yu vi giỏ tr IC50 tng ng l 0,49 v 0,55 mg/ml (Hu et al., 2010) Ba hp cht lignan mi l ficusal (74), ficusesquilignan A (75) v ficusesquilignan B (76) (Hỡnh 1.5) c phỏt hin t g cõy Ga vo nm 2000 (Li, Kuo, 2000) -22c Cỏc hp cht phenyl propanoid Nm 2006, mt phenylpropanoid mi ficuscarpanoside B (77) cựng vi