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Dalbergia Tonkinensis Prain) Ở Việt Nam

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Dalbergia Tonkinensis Prain) Ở Việt Nam BỘ GIÁO DỤC VÀ ĐÀO TẠO VIỆN HÀN LÂM KHOA HỌC VÀ CÔNG NGHỆ VIỆT NAM HỌC VIỆN KHOA HỌC VÀ CÔNG NGHỆ NGŨ TRƯỜNG NHÂN NGHIÊN CỨU THÀNH PHẦN HÓA HỌC VÀ HOẠT TÍNH SINH HỌC CỦA LOÀI SƯA (DALBERGIA TONKINENSIS PRAIN) Ở VIỆT NAM LUẬN ÁN TIẾN SỸ HÓA HỌC Hà Nội, 2019 BỘ GIÁO DỤC VÀ ĐÀO TẠO VIỆN HÀN LÂM KHOA HỌC VÀ CÔNG NGHỆ VIỆT NAM HỌC VIỆN KHOA HỌC VÀ CÔNG NGHỆ NGŨ TRƯỜNG NHÂN NGHIÊN CỨU THÀNH PHẦN HÓA HỌC VÀ HOẠT TÍNH SINH HỌC CỦA LOÀI SƯA (DALBERGIA TONKINENSIS PRAIN) Ở VIỆT NAM LUẬN ÁN TIẾN SỸ HÓA HỌC Chuyên ngành: Hóa học các hợp chất thiên nhiên Mã số chuyên ngành: 9.44.01.17 Người hướng dẫn khoa học: 1. PGS.TS. Nguyễn Mạnh Cường 2. TS. Đỗ Hữu Nghị Hà Nội, 2019 i MỤC LỤC LỜI CAM ĐOAN .................................................................................................... v LỜI CẢM ƠN ........................................................................................................ vi DANH MỤC CÁC KÝ HIỆU, CÁC CHỮ VIẾT TẮT .......................................... vii DANH MỤC CÁC BẢNG ..................................................................................... ix DANH MỤC CÁC HÌNH ...................................................................................... xi DANH MỤC CÁC SƠ ĐỒ .................................................................................. xiv DANH MỤC CÁC PHỤ LỤC ............................................................................... xv MỞ ĐẦU ................................................................................................................ 1 CHƯƠNG 1: TỔNG QUAN ...................................................................................................3 1.1. KHÁI QUÁT VỀ HỌ ĐẬU (FABACEAE) VÀ CHI TRẮC (DALBERGIA) ................3 1.1.1. Khái quát về họ Đậu (Fabaceae) ............................................................. 3 1.1.2. Khái quát về chi Trắc (Dalbergia) .......................................................... 3 1.1.3. Tổng quan về loài Sưa (Dalbergia tonkinensis Prain) .............................. 4 1.2. TÌNH HÌNH NGHIÊN CỨU VỀ THÀNH PHẦN HÓA HỌC CỦA CHI TRẮC (DALBERGIA) TRÊN THẾ GIỚI ..............................................................................................5 1.2.1. Hợp chất khung flavan ........................................................................... 7 1.2.2. Hợp chất khung isoflavan ....................................................................... 8 1.2.3. Hợp chất khung neoflavan .................................................................... 10 1.2.4. Hợp chất khung flavanol ...................................................................... 10 1.2.5. Hợp chất khung flavanone .................................................................... 11 1.2.6. Hợp chất khung isoflavanone................................................................ 14 1.2.7. Hợp chất khung flavanonol ................................................................... 15 1.2.8. Hợp chất khung isoflavanonol .............................................................. 16 1.2.9. Hợp chất khung flavone ....................................................................... 17 1.2.10. Hợp chất khung isoflavone ............................................................... 18 1.2.11. Hợp chất khung neoflavone .............................................................. 21 1.2.12. Hợp chất khung 4-aryl-coumarin....................................................... 21 1.2.13. Hợp chất khung aurone ....................................................................... 23 ii 1.2.14. Hợp chất khung chalcone ................................................................... 23 1.2.15. Lớp chất diaryl propanoid .................................................................. 25 1.2.16. Lớp chất cumarin và dẫn xuất ............................................................. 25 1.2.17. Lớp chất lignan .................................................................................. 27 1.2.18. Lớp chất benzophenon........................................................................ 28 1.2.19. Lớp chất terpenoid ............................................................................. 28 1.2.20. Các lớp chất khác ............................................................................... 29 1.3. TÌNH HÌNH NGHIÊN CỨU VỀ THÀNH PHẦN HÓA HỌC CỦA CHI TRẮC (DALBERGIA) Ở VIỆT NAM ................................................................................................ 30 1.4. HOẠT TÍNH SINH HỌC CỦA CHI TRẮC (DALBERGIA)........................................ 34 1.4.1. Hoạt tính chống oxi hóa ....................................................................... 34 1.4.2. Hoạt tính gây độc tế bào ....................................................................... 37 1.4.3. Hoạt tính kháng khuẩn ......................................................................... 40 1.4.4. Hoạt tính kháng viêm ........................................................................... 41 1.4.5. Hoạt tính chống đái tháo đường ............................................................ 41 1.4.6. Hoạt tính chống dị ứng ......................................................................... 42 CHƯƠNG 2: THỰC NGHIỆM VÀ PHƯƠNG PHÁP NGHIÊN CỨU ............ 43 2.1. Đối tượng và phương pháp nghiên cứu ............................................................................ 43 2.1.1. Thu mẫu cây, xác định tên khoa học và phương pháp xử lý mẫu ............ 43 2.1.2. Các phương pháp nghiên cứu thực vật loài Sưa (Dalbergia tonkinensis Prain) ............................................................................................................ 43 2.1.3. Phương pháp phân lập các hợp chất từ các dịch chiết ............................. 46 2.1.4. Các phương pháp xác định cấu trúc hóa học các hợp chất ...................... 46 2.2. Phương pháp thử nghiệm hoạt tính sinh học .................................................................... 46 2.2.1. Phương pháp đánh giá hoạt tính kháng vi sinh vật kiểm định ................. 46 2.2.2. Phương pháp thử hoạt tính ức chế enzyme -glucosidase ...................... 48 2.3. Xử lý mẫu thực vật và chiết tách ....................................................................................... 49 2.3.1. Cây Sưa (Dalbergia tonkinensis Prain) (C-561)..................................... 49 2.3.2. Cây Sưa (Dalbergia tonkinensis Prain) (C-612)..................................... 54 2.4. Thông số hóa lý và dữ kiện phổ các hợp chất phân lập ................................................... 61 iii CHƯƠNG 3: KẾT QUẢ VÀ BÀN LUẬN .......................................................... 67 3.1. KẾT QUẢ NGHIÊN CỨU VỀ VI PHẪU VÀ DNA CỦA CÂY SƯA (DALBERGIA TONKINENSIS PRAIN) .......................................................................................................... 67 3.1.1. Kết quả nghiên cứu vi phẫu cây Sưa (Dalbergia tonkinensis Prain) ........ 67 3.1.2. Kết quả nghiên cứu DNA cây Sưa (Dalbergia tonkinensis Prain) ........... 70 3.2. THÀNH PHẦN HÓA HỌC CÂY SƯA (DALBERGIA TONKINENSIS PRAIN) (C- 561) ........................................................................................................................................ 74 3.2.1. Hợp chất pinocembrin (DT.01) ............................................................. 75 3.2.2. Hợp chất naringenin (DT.02) ................................................................ 78 3.2.3. Hợp chất 3'-hydoxy-2,4,5-trimethoxydalbergiquinol (DT.03)................. 80 3.2.4. Hợp chất medicarpin (DT.04) ............................................................... 82 3.2.5. Hợp chất buteaspermanol (DT.05) ........................................................ 84 3.2.6. Hợp chất mới daltonkin A (DT.06) ....................................................... 85 3.2.7. Hợp chất mới daltonkin B (DT.07) ....................................................... 93 3.3. THÀNH PHẦN HÓA HỌC CÂY SƯA (DALBERGIA TONKINENSIS PRAIN) (C- 612) ...................................................................................................................................... 101 3.3.1. Hợp chất Dalbergin (DT.08) ................................................................ 101 3.3.2. Hợp chất isoliquiritigenin (DT.09) ....................................................... 102 3.3.3. Hợp chất 7,3',5'-trihydroxyflavanone (DT.10) ...................................... 104 3.3.4. Hợp chất vestitone (DT.11) ................................................................. 106 3.3.5. Hợp chất calycosin (DT.12) ................................................................. 108 3.3.6. Hợp chất 4',7-dihidroxy-3-methoxyflavone (DT.13) ............................. 109 3.3.7. Hợp chất liquiritigenin (DT.14) ........................................................... 110 3.3.8. Hợp chất sativanone (DT.15) ............................................................... 112 3.3.9. Hợp chất 3'-O-methylviolanone (DT.16) .............................................. 112 3.3.10. Hợp chất sulfuretin (DT.17)............................................................... 114 3.3.11. Hợp chất formononetin (DT.18) ......................................................... 115 3.4. KẾT LUẬN VỀ XÁC ĐỊNH CẤU TRÚC CÁC HỢP CHẤT ................................... 116 3.5. ĐÁNH GIÁ TÁC DỤNG SINH HỌC .......................................................................... 119 iv 3.5.1. Khảo sát hoạt tính kháng khuẩn của các hợp chất từ cặn chiết dichloromethane ..........................................................................................
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