B GIO DC V O TO VIN HN LM KHOA HC V CễNG NGH VIT NAM HC VIN KHOA HC V CễNG NGH - NGUYN HONG SA NGHIấN CU THNH PHN HểA HC V HOT TNH SINH HC CA CC LOI L KIM: PINUS DALATENSIS, PINUS KESIYA V PODOCARPUS NERIIFOLIUS VIT NAM LUN N TIN S HểA HC H NI 2017 VIN HN LM KHOA HC V CễNG NGH VIT NAM HC VIN KHOA HC V CễNG NGH .*** NGUYN HONG SA NGHIấN CU THNH PHN HểA HC V HOT TNH SINH HC CA CC LOI L KIM: PINUS DALATENSIS, PINUS KESIYA V PODOCARPUS NERIIFOLIUS VIT NAM LUN N TIN S HểA HC Chuyờn ngnh: Hoỏ hu c Mó s: 62 44 01 14 Ngi hng dn khoa hc 1: PGS.TS Trnh Th Thy Ngi hng dn khoa hc 2: TS Nguyn Thanh Tõm H Ni 2017 LI CAM OAN Tụi xin cam oan: õy l cụng trỡnh nghiờn cu ca riờng tụi di s hng dn khoa hc ca PGS.TS Trnh Th Thy v TS Nguyn Thanh Tõm Cỏc kt qu thu c lun ỏn hon ton trung thc v cha c cụng b bt k cụng trỡnh no khỏc Ton b trớch dn lun ỏn u ch rừ ngun gc Tỏc gi lun ỏn Nguyn Hong Sa LI CM N Lun ỏn ny c hon thnh ti Vin Húa hc, Vin Hn lõm Khoa hc v Cụng ngh Vit Nam Trong quỏ trỡnh nghiờn cu, tỏc gi ó nhn c nhiu s giỳp quý bỏu ca thy cụ, cỏc nh khoa hc cng nh ng nghip, bn bố v gia ỡnh Tụi xin by t lũng bit n chõn thnh v sõu sc n PGS.TS Trnh Th Thy v TS Nguyn Thanh Tõm l nhng ngi ó hng dn tn tỡnh, chu ỏo v to mi iu kin giỳp tụi thi gian thc hin lun ỏn Tụi xin chõn thnh cm n th cỏn b Phũng Nghiờn cu hp cht thiờn nhiờn, Phũng Tng hp hu c, Vin Húa hc ó giỳp , h tr tụi sut quỏ trỡnh lm lun ỏn Tụi xin trõn trng cm n s quan tõm giỳp ca Hc vin Khoa hc v Cụng ngh, lónh o Vin Húa hc, b phn o to Phũng Qun lý tng hp ó to iu kin v giỳp tụi hon thnh lun ỏn Tụi xin trõn trng cm n lónh o Trng i hc Khỏnh Hũa, trng Khoa cựng cỏn b ca Khoa T nhiờn v Cụng ngh ó to mi iu kin thun li cho tụi thi gian lm lun ỏn Tụi cng xin by t lũng bit n ti GS.TSKH Trn Vn Sung ó cú nhng nh hng xõy dng nn múng ban u cho tụi trờn ng hc v nghiờn cu khoa hc Cui cựng, tụi xin chõn thnh cm n gia ỡnh v bn bố ó c v, ng viờn tụi hon thnh lun ỏn Tụi xin trõn trng cm n ! H Ni, ngy thỏng nm 2017 Tỏc gi lun ỏn Nguyn Hong Sa MC LC MC LC i DANH MC CC Kí HIU V CH VIT TT iv DANH MC CC BIU BNG vii DANH MC CC HèNH viii PH LC ix M U Chng TNG QUAN 1.1 Tng quan v cỏc loi nghiờn cu 1.1.1 Thụng lt (Pinus dalatensis) 1.1.2 Thụng ba lỏ (Pinus kesiya) 1.1.3 Thụng tre lỏ di dai (Podocarpus neriifolius) 1.2 Tỡnh hỡnh nghiờn cu v húa hc mt s loi thuc chi Pinus 1.2.1 Nghiờn cu v thnh phn tinh du t chi Pinus 1.2.2 Cỏc hp cht terpenoid t chi Pinus 1.2.3 Cỏc hp cht flavonoid t chi Pinus 14 1.2.4 Cỏc hp cht lignan t chi Pinus 17 1.2.5 Cỏc hp cht khỏc t chi Pinus 19 1.3 Mt s nghiờn cu v thnh phn húa hc ca Thụng ba lỏ 20 1.4 Cỏc nghiờn cu v hot tớnh sinh hc ca cỏc cht phõn lp t cỏc loi thuc chi Pinus 20 1.4.1 Hot tớnh khỏng viờm v gim au 21 1.4.2 Hot tớnh c ch cỏc u v khỏng ung th 22 1.4.3 Hot tớnh khỏng khun v khỏng nm 24 1.4.4 Hot tớnh chng oxi húa 26 1.4.5 Hot tớnh khỏng virus v mt s hot tớnh khỏc 27 1.5 Tỡnh hỡnh nghiờn cu v húa hc v hot tớnh sinh hc mt s loi thuc chi Podocarpus 28 1.6 Tỡnh hỡnh nghiờn cu v húa hc ca loi thụng tre lỏ di (Podocarpus neriifolius) 39 Chng THC NGHIM 42 i 2.1 Thu hỏi mu cõy v xỏc nh tờn khoa hc 42 2.2 Phng phỏp x lý v chit mu 42 2.3 Phng phỏp kho sỏt, phõn tỏch v tinh ch cỏc hp cht t mu thc vt 42 2.4 Phng phỏp xỏc nh cu trỳc 43 2.5 Phng phỏp th mt s hot tớnh sinh hc 43 2.6 Húa cht v thit b 46 2.7 Quy trỡnh chit v thu cỏc chit xut t cỏc loi thc vt nghiờn cu 47 2.8 Phõn lp cht t cỏc chit xut 48 2.8.1 Phõn lp cỏc cht t chit xut ethyl acetate ca g Thụng lt 48 2.8.2 Phõn lp cỏc cht t chit xut n-butanol ca g Thụng lt 49 2.8.3 Phõn lp cỏc cht t chit xut n-hexane ca lỏ Thụng lt 49 2.8.4 Phõn lp cỏc cht t chit xut ethyl acetate ca lỏ Thụng lt 50 2.8.5 Phõn lp cỏc cht t chit xut ethyl acetate ca r Thụng ba lỏ 51 2.8.6 Phõn lp cỏc cht t chit xut ethyl acetate ca g Thụng tre lỏ di 52 2.9 D kin ph ca cỏc cht tỏch c 60 Chng KT QU V THO LUN 70 3.1 Cỏc cht c phõn lp t Thụng lt (Pinus dalatensis) 70 3.1.1 Cht TT1: Caryolane-1,9-diol 70 3.1.2 Hn hp TT2 71 3.1.3 Cht TT3: 15-Methoxypinusolidic acid 73 3.1.4 Cht TT4: Lambertianic acid 75 3.1.5 Cht TT5: 8(17), 13-ent-Labdadien-1516-lactone-19-oic acid 77 3.1.6 Cht TT6: Isopimaric acid 78 3.1.7 Cht TT12: 3-Hydroxy-14-serraten-21-one 79 3.1.8 Cht TF1: Pinocembrin 81 3.1.9 Cht TF2: Chrysin 82 3.1.10 Cht TF3: Pinostrobin 83 3.1.11 Cht TF4: (+) Catechin 84 3.1.12 Cht TF5: Kaempferol 85 ii 3.1.13 Cht TF7: Kaempferol 3-O-(3,6-di-O-E-p-coumaroyl)--D-glucopyranoside 86 3.1.14 Cht TP1: Dihydropinosylvin 89 3.1.15 Cht TP2: Dihydropinosylvin 5-methyl ether 89 3.1.16 Cht TP3: 3-Hydroxy-5-methoxystilbene 90 3.1.17 Hn hp TP5 90 3.1.18 Cht TP6: Vanillic acid 4-(--D-glucopyranoside) 92 3.1.19 Cht TL1: (+) Lariciresinol 94 3.1.20 Cht TL3: Cedrusin-4-O--D-glucopyranoside 95 3.1.21 Cht TS1: -Sitosterol 97 3.1.22 Cht TS2: Daucosterol 98 3.2 Cỏc cht c phõn lp t Thụng ba lỏ (Pinus kesiya) 99 3.2.1 Cht TT11: 7-Oxo-15-hydroxydehydroabietic acid 99 3.2.2 Cht TF6: 3-O-Methylcatechin 7-O--D-glucopyranoside 101 3.2.3 Cht TP4: Resveratrol-3-O--D-glucoside 102 3.2.4 Cht TP7: 3,4-Dimethoxyphenyl 2-O-(3-O-methyl--L-rhamnopyranosyl) -D-glucopyranoside 103 3.2.5 3.3 Cht TL2: Cedrusin 105 Cỏc cht c phõn lp t Thụng tre lỏ di (Podocarpus neriifolius) 105 3.3.1 Cht TT7: Totarol 105 3.3.2 Cht TT8: Totarol-19-carboxylic acid 106 3.3.3 Cht TT9: Inumakiol D 107 3.3.4 Cht TT10: Macrophyllic acid 108 3.4 Hot tớnh sinh hc ca mt s cht sch 111 KT LUN V KIN NGH 116 DANH SCH CC CễNG TRèNH CễNG B 119 TI LIU THAM KHO 120 iii DANH MC CC Kí HIU V CH VIT TT CC GFC TLC H-NMR 13 C-NMR COSY Cỏc phng phỏp sc ký Column Chromatography Gel filtration chromatography Thin Layer Chromatography Cỏc phng phỏp ph Proton Nuclear Magnetic Resonance Spectroscopy Carbon-13 Nuclear Magnetic Resonance Spectroscopy Correlation Spectroscopy DEPT Distortionless Enhancement by Polarisation Transfer ESI-MS Electron Spray Ionization Mass Spectrometry HR-ESI-MS High Resolution - Electron Spray Ionization - Mass Spectrometry HMBC Heteronuclear Multiple Bond Correlation IR NOESY Ph cng hng t ht nhõn H Ph cng hng t ht nhõn carbon 13 Ph tng tỏc hai chiu 1H1 H Ph DEPT Ph ion húa phun mự in t Ph phõn gii cao ion húa phun mự in t Ph tng tỏc d ht nhõn qua nhiu liờn kt t: triplet q: quartet brd: broad doublet ddd: doublet of doublet of doublets dt: doublet of triplets s: singlet d: doublet m: multiplet brs: broad singlet dd: doublet of doublets td: triplet of doublets HSQC Sc ký ct thng Sc ký lc Gel Sc ký bn mng Heteronuclear Single Quantum Coherence Infrared Spectroscopy Nuclear Overhauser Effect Spectroscopy Cỏc dũng t bo 9-KB Human epidermoid carcinoma 26-L5 A-431 A-549 Murine colon carcinoma Human epidermoid carcinoma Human bronchogenic carcinoma iv Ph tng tỏc d ht nhõn qua mt liờn kt Ph hng ngoi Ph NOESY Ung th biu mụ hng ngi Ung th rut kt chut Ung th biu mụ ngi Ung th phi ngi Bel-7402 Human hepatoma DU-145 Human prostate adenocarcinoma HeLa Hep-G2 HeLa cell line Human hepatocellular carcinoma HL-60 Human promyelocytic leukemia HT-1080 Human fibrosarcoma KB Human epidermoid carcinoma L-929 Mouse fibroblast LNCaP Human prostate adenocarcinoma LU MCF-7 Human bronchogenic carcinoma Human breast adenocarcinoma NCI-H292 Human lung mucoepidermoid OCI-AML Acute Myeloid Leukemia cells P-388 Lymphocytic leukemia PC-3 Human prostate adenocarcinoma SK-LU-1 Human Caucasian Lung adenocarcinoma SK-N-SH Human neuroblastoma cell line SMMC7721 T-47D U-397 COX-2 CTPT EBV ED50 Human hepatocarcinoma Human ductal breast epithelial tumor Human leukemic monocyte lymphoma Cỏc vit tt khỏc Cyclooxygenase-2 Epstein-Barr Virus Effective Dose v Ung th gan ngi Ung th tuyn tin lit ngi T bo ung th Hela Ung th gan ngi Ung th mỏu cp tớnh ngi bo ung th biu mụ liờn kt di cn ngi Ung th biu mụ ngi Ung th biu mụ liờn kt si chut Ung th tuyn tin lit ngi Ung th phi ngi Ung th vỳ ngi Ung th biu mụ phi ngi T bo ung th bch cu myeloid cp tớnh Ung th mỏu lympho (Ung th bch cu) Ung th tuyn tin lit ngi Ung th phi ngi U nguyờn bo thn kinh ngi Ung th biu mụ t bo gan ngi Ung th vỳ ngi Ung th mỏu ngi Enzym cyclooxygenase-2 Cụng thc phõn t Virus Epstein-Barr Liu tỏc dng ti a trờn 50% i tng th FIV Feline immunodeficiency virus HSV Herpes simplex virus HIV Human immunodeficiency virus IC50 Inhibitory Concentration 50% LD50 MIC Lethal Dose 50 Minimum Inhibitory Concentration MMTV Mouse mammary tumour virus OD Optical Density ROS Reactive oxygen species mp Melting point Virus gõy suy gim dch ng vt h mốo Virus Herpes simplex Virus gõy suy gim dch ngi Nng c ch 50% i tng th Liu gõy cht 50% thỳ th Nng c ch ti thiu Chng virus gõy ung th vỳ chut Mt quang Nhng phn t hot ng cha Oxygen im núng chy n-BuOH CDCl3 DCM DMSO EtOAc EtOH MeOH CD3OD TMS n-Butanol Chloroform deuteri (d) Dichloromethane Dimethylsulfoxide Ethyl acetate Ethanol Methanol Methanol deuteri (d4) Tetramethylsilane Ac Bz OMe Ph Et Me Glc Acetoxyl Benzoyl Methoxy Phenyl Ethyl Methyl Glucose Xyl C Carbon bc Rf Xylose Retardation factor (retention factor) 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HỌC VÀ CÔNG NGHỆ VIỆT NAM HỌC VIỆN KHOA HỌC VÀ CÔNG NGHỆ …… ….***………… NGUYỄN HOÀNG SA NGHIÊN CỨU THÀNH PHẦN HÓA HỌC VÀ HOẠT TÍNH SINH HỌC CỦA CÁC LOÀI LÁ KIM: PINUS DALATENSIS, PINUS KESIYA VÀ... Gordon) loài Thông tre dài (Podocarpus neriifolius D Don) giới có vài nghiên cứu nên việc nghiên cứu thành phần hóa học hoạt tính sinh học ba loài cần thiết, nhằm góp phần tạo sở để hướng đến nghiên. .. 24 1.4.4 Hoạt tính chống oxi hóa 26 1.4.5 Hoạt tính kháng virus số hoạt tính khác 27 1.5 Tình hình nghiên cứu hóa học hoạt tính sinh học số loài thuộc chi Podocarpus