Nghiên cứu thành phần hóa học và hoạt tính chống oxy hóa của một số loài dược liệu của đồng bào pa cô và bru vân kiều, tỉnh quảng trị

LỜI CAM ĐOAN Tôi xin cam đoan: Đây công trình nghiên cứu riêng tơi, kết thu luận án hoàn toàn trung thực, đồng tác giả cho phép sử dụng chưa cơng bố cơng trình khác Tác giả luận án Lê Trung Hiếu LỜI CẢM ƠN Luận án hồn thành Khoa Hóa, Trường Đại học Khoa học, Đại học Huế Tôi xin bày tỏ lòng biết ơn chân thành sâu sắc đến PGS.TS Trần Thị Văn Thi Người hướng dẫn tận tình, chu đáo tạo điều kiện tốt giúp đỡ thời gian thực luận án Tôi xin trân trọng cảm ơn quan tâm giúp đỡ Ban Giám Hiệu Trường Đại học Khoa học, Phòng Đào tạo Sau Đại học Trường Đại học Khoa học, Phòng Đào tạo Sau Đại học Đại học Huế tạo điều kiện giúp đỡ tơi hồn thành luận án Tôi xin trân trọng cảm ơn Ban Chủ nhiệm Khoa Q Thầy Cơ Khoa Hóa giúp đỡ tạo điều kiện thuận lợi cho thời gian làm luận án Tôi xin trân trọng cảm ơn PGS TS Nguyễn Thị Hoài, PGS TS Phạm Cẩm Nam, PGS TS Võ Thị Mai Hương, TS Hồ Việt Đức NCS Lê Lâm Sơn giúp đỡ tơi q trình thực nghiệm Cuối cùng, tơi xin chân thành cảm ơn gia đình bạn bè cổ vũ, động viên tơi hồn thành luận án Tôi xin trân trọng cảm ơn ! Thừa Thiên Huế, ngày…tháng…năm 2017 Tác giả luận án Lê Trung Hiếu MỤC LỤC DANH MỤC CÁC KÝ HIỆU VÀ CHỮ VIẾT TẮT Các loài dược liệu Ab A bauchei Archidendron bauchei Ac A clypearia Archidendron clypearia Hp H parasitica Helixanthera parasitica Lr L rubra Leea rubra Mc M casearifolia Microdesmis casearifolia Pv P venusta Pyrostegia venusta So S oleracea Spilanthes oleracea Hoạt tính chống oxy hóa ROS Reactive oxygene species DPPH 1,1-diphenyl-2picrylhydrazyl TPC Tổng hàm lượng hợp TFC Tổng hàm lượng chất phenol TAC flavonoid Hàm lượng chất chống TA5C-HPLC Hàm lượng tổng oxy hóa quy tương đương hợp chất chống oxy gallic acid hóa xác định phương pháp HPLC HAT Hydrogen Atom Transfer SET Single Electron Transfer AST Aspartate Amino ALT Transferase PAR Alanin Amino Transferase Paracetamol Các phương pháp sắc ký CC Column Chromatography Sắc ký cột thường HPLC High Performance Liquid Sắc ký lỏng hiệu cao Chromatography TLC Thin Layer Chromatography Sắc ký mỏng Các phương pháp phổ H-NMR 13 C-NMR APCI-MS DEPT Proton Nuclear Magnetic Phổ cộng hưởng từ hạt nhân Resonance Spectroscopy proton Carbon-13 Nuclear Magnetic Phổ cộng hưởng từ hạt nhân Resonance Spectroscopy carbon 13 Atmospheric Pressure Chemical Phổ khối ion hóa hóa học áp Ionization Mass Spectrometry suất khí Distortionless Enhancement by Phổ DEPT Polarisation Transfer COSY Correlation Spectroscopy Phổ tương tác hai chiều 1H- 1H ESI-MS Electron Spray Ionization Mass Phổ khối ion hóa phun mù điện Spectrometry tử Heteronuclear Multiple Bond Phổ tương tác dị hạt nhân qua Correlation nhiều liên kết High Resolution - Electron Phổ khối phân giải cao ion hóa Spray Ionization - Mass phun mù điện tử HMBC HR-ESI-MS Spectrometry HSQC HSQC Heteronuclear Single Phổ tương tác dị hạt nhân qua Quantum Coherence liên kết IR Infrared Spectroscopy Phổ hồng ngoại J (Hz) Hằng số tương tác tính Hz NOESY Nuclear Overhauser Effect Phổ NOESY Spectroscopy UV Ultraviolet Spectroscopy Phổ tử ngoại δ (ppm) (ppm = part per million) Độ dịch chuyển hóa học tính phần triệu s singlet q quartet dt double triplet d doublet dd double doublet br broad triplet m multiplet t Các ký hiệu viết tắt khác IC50 Inhibitory Concentration 50% Nồng độ ức chế 50% ED50 Effective dose 50% Liều lượng hiệu nồng độ 50% BDE Bond dissociation energy Năng lượng phân ly liên kết IE Ionization energy Năng lượng ion hóa Mp Melting point Điểm chảy OD Optical Density Mật độ quang CTPT Công thức phân tử EtAc Ethyl acetate DMSO B n-Butanol MeOH Methanol Dimethylsulfoxide C Chloroform H n-Hexane W Water GA Gallic aicd QU Quercetin DANH MỤC CÁC BIỂU BẢNG DANH MỤC CÁC HÌNH DANH MỤC CÁC PHỤ LỤC Phụ lục Kết giám định tên thực vật PL1 Phụ lục Kết mật độ quang cao toàn phần nồng độ PL2 Phụ lục Kết mật độ quang dung dịch chuẩn gallic acid quercetin sau lên màu với thuốc thử PL3 Phụ lục Kết mật độ quang phân đoạn nồng độ PL4 Phụ lục Tỷ lệ bắt gốc tự DPPH (%) dung dịch cao phân đoạn .PL6 Phụ lục Các phổ hợp chất số 1: lup-20(29)-en-3-one PL8 Phụ lục Các phổ hợp chất số 2: α-tocospiro A PL9 Phụ lục Các phổ hợp chất số 3: spinasterol PL11 Phụ lục Các phổ hợp chất số 4: oleanolic acid PL12 Phụ lục Phổ 1H-NMR hợp chất số 5: daucosterol PL13 Phụ lục 10 Các phổ hợp chất số 6: methyl gallate PL14 Phụ lục 11 Các phổ hợp chất số 7: quercetin PL15 Phụ lục 12 Các phổ hợp chất số 8: Rutin PL16 Phụ lục 13 Các phổ hợp chất số 9: α-tocopherol .PL18 Phụ lục 14 Các phổ hợp chất số 10: betulinic acid PL20 Phụ lục 15 Các phổ hợp chất số 11: α-spinasterone PL22 Phụ lục 16 Phổ 1H-NMR hợp chất 12: stigmasterol PL23 Phụ lục 17 Phổ 1H-NMR hợp chất 13: 1-octacosanol .PL24 Phụ lục 18 Các phổ hợp chất số 14: docosenoic acid PL25 Phụ lục 19 Các phổ hợp chất số 15: quercitrin PL26 Phụ lục 20 Các phổ hợp chất số 16: 7-O-galloyltricetiflavan PL29 Phụ lục 21 Tỷ lệ bắt gốc tự DPPH hợp chất phân lập .PL31 Phụ lục 22 Kết hoạt tính chống oxy hóa in vitro hợp chất phân lập PL32 Phụ lục 23 Sắc ký đồ chất chuẩn dung dịch cao toàn phần PL33 Phụ lục 24 Sắc ký đồ chất chuẩn dung dịch cao toàn phần PL50 MỞ ĐẦU Hoạt tính chống oxy hóa hoạt tính sinh học quan trọng xem xét phổ biến khía cạnh sử dụng thực phẩm hay dược liệu để phòng bệnh chữa bệnh Các dạng oxy hoạt động, bao gồm gốc tự ion chứa oxy có hoạt tính oxy hóa cao OH , HOO-, O2-,… có lượng cao bền nên dễ dàng công đại phân tử ADN, protein,… gây biến dị, huỷ hoại tế bào, gây ung thư, bệnh tim mạch, tiểu đường, béo phì tăng nhanh lão hố [25], [135] Vì vậy, việc bổ sung chất chống oxy hóa để kiểm soát hàm lượng ổn định gốc tự mang lại nhiều lợi ích tốt cho thể bảo vệ toàn vẹn tế bào, ngăn ngừa số tai biến, làm chậm trình lão hố thể, bảo vệ chức gan, hạn chế tác nhân gây viêm, bảo vệ chức hệ thần kinh, giảm thiểu tác nhân gây ung thư điều trị bệnh Alzheimer, Parkinson [61], [136], [88] Một đường quan trọng để phát hợp chất có hoạt tính sinh học xuất phát từ tri thức địa Quá trình nghiên cứu định hướng dựa theo kinh nghiệm sử dụng thuốc qua trình sàng lọc hoạt tính sinh học, tích lũy lâu dài lưu truyền từ hệ qua hệ khác cộng đồng dân tộc, tương tự hàng ngàn thử nghiệm in vivo thể người qua thời gian dài, giảm nhiều thời gian, công sức tiền so với sàng lọc phòng thí nghiệm Từ kết điều tra thuốc mà đồng bào Pa Cô Bru - Vân Kiều thuộc tỉnh Quảng Trị dùng để chữa loại bệnh có liên quan đến hoạt tính chống oxy hóa viêm gan, viêm họng, khối u vùng bụng , Nguyễn Thị Hồi nhóm nghiên cứu chọn 16 loài dược liệu từ 102 loài, sử dụng phương pháp sàng lọc theo hoạt tính chống oxy hóa phòng thí nghiệm để thu 02 lồi dược liệu có hoạt tính chống oxy hóa bật (mạnh tương đương với curcumin) Mán đỉa Cúc nút áo [2] Bên cạnh đó, nghiên cứu ban đầu chúng tơi cho thấy cao tồn phần từ lồi dược liệu: Cổ ướm (Archidendron bauchei), Mán đỉa (Archidendron clypearia), Chùm gởi (Helixanthera parasitica), Gối hạc (Leea 10 16 17 18 19 20 21 22 23 24 25 26 27 research, 23(6), 892-895 Altoé, T D., de Amorim, G M., Gomes, J V D., Borges, A S., Valadão, I C., Silva, I V., & Borges, W D S (2014) In vitro antioxidant and cell viability of Pyrostegia venusta (Ker Gawl.) 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X (2004) Effect of Selenium on Increasing the Antioxidant Activity of Protein Extracts from a Selenium‐enriched Mushroom Species of the Ganoderma Genus Journal of food science, 69(3) Internet 181 zzzHttp://www.lrc-hueuni.edu.vn/dongy/show_target.plx? url=/thuocdongy/M/Mandia.htm&key=&char=M 1990 182 zzzHttp://www.lrc-hueuni.edu.vn/dongy/show_target.plx? url=/thuocdongy/R/RangDong.htm&key=&char=R 183 zzzHttp://www.lrchueuni.edu.vn/dongy/show_target.plx? 160 url=/thuocdongy/C/ChanhOc.htm&key=&char=C Chanh ốc 184 zzzwwwhttp://bacsytructuyen.com/diendan/baiviet/15579-cuc-ao-rau-spilanthesoleracea-cay-thuoc-nam-dung-cho-tre-em-bi-chung-noi-lap/#ixzz45yKfbMN7 185 zzzWwwHttp://baithuochay.net/home/?frame=bai-thuoc&p=542&.html 161 ... học hoạt tính chống oxy hóa chúng Trên sở đó, luận án đặt nhiệm vụ Nghiên cứu thành phần hóa học hoạt tính chống oxy hóa số lồi dược liệu đồng bào Pa Cô Bru - Vân Kiều, tỉnh Quảng Trị Kết luận... hoạt tính chống oxy hóa tốt mơ hình thử nghiệm hóa học chưa có hoạt 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