Khóa luận tốt nghiệp: Khảo sát thành phần hóa học phân đoạn A5 cao chloroform rễ cây hà thủ ô trắng Streptocaulon juventas

Cây Hà thủ ô trắng có tên khoa học là Streptocaulon juventas (Lour) Merr, thuộc họ thiên lý Asclepiadaceae. Cây Hà thủ ô trắng có công dụng làm cho người già trẻ lại, giúp cho sự giao hợp được bền lâu, tóc bạc hóa đen. Trong kháng chiến tại các vùng dân tộc, người ta dùng củ và thân lá cây này chữa cảm sốt, cảm nắng, sốt rét. Ngoài ra, có nơi người... Đề tài Hoàn thiện công tác quản trị nhân sự tại Công ty TNHH Mộc Khải Tuyên được nghiên cứu nhằm giúp công ty TNHH Mộc Khải Tuyên làm rõ được thực trạng công tác quản trị nhân sự trong công ty như thế nào từ đó đề ra các giải pháp giúp công ty hoàn thiện công tác quản trị nhân sự tốt hơn trong thời gian tới.

BỘ GIÁO DỤC VÀ ĐÀO TẠO TRƢỜNG ĐẠI HỌC SƢ PHẠM THÀNH PHỐ HỒ CHÍ MINH KHOA HĨA HỌC  KHÓA LUẬN TỐT NGHIỆP KHẢO SÁT THÀNH PHẦN HÓA HỌC PHÂN ĐOẠN A5 CAO CHLOROFORM RỄ CÂY HÀ THỦ Ô TRẮNG Streptocaulon juventas 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b NGUYỄN HỮU TOÀN 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 Thành phố Hồ Chí Minh, ngày 05 tháng 05 năm 2019 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 BỘ GIÁO DỤC VÀ ĐÀO TẠO TRƢỜNG ĐẠI HỌC SƢ PHẠM THÀNH PHỐ HỒ CHÍ MINH KHOA HĨA HỌC  KHĨA LUẬN TỐT NGHIỆP KHẢO SÁT THÀNH PHẦN HÓA HỌC PHÂN ĐOẠN A5 CAO CHLOROFORM RỄ CÂY HÀ THỦ Ô TRẮNG Streptocaulon juventas 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 Giảng viên hƣớng dẫn: TS Bùi Xuân Hào d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 Sinh viên thực hiện: Nguyễn Hữu Toàn 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 Mã số sinh viên: K40.201.094 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 Thành phố Hồ Chí Minh, ngày 05 tháng 05 năm 2019 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 NHẬN XÉT CỦA GIẢNG VIÊN PHẢN BIỆN 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 Thành phố Hồ Chí Minh, ngày 05 tháng 05 năm 2019 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 Giảng viên phản biện df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Khóa luận tốt nghiệp Nguyễn Hữu Toàn LỜI CẢM ƠN Nghiên cứu đƣợc thực phịng thí nghiệm Hợp chất thiên nhiên, khoa Hóa học, trƣờng Đại học Sƣ phạm thành phố Hồ Chí Minh Em xin chân thành cảm ơn giáo viên hƣớng dẫn Thầy Bùi Xuân Hào tận tâm việc truyền đạt kiến thức kinh nghiệm quý báu Thầy ln theo dõi q trình làm việc em để kịp thời phát hiện, điều chỉnh, sửa chữa sai sót Tất nhằm tạo điều kiện tối ƣu để em hồn thành Khóa luận tốt nghiệp Song song với học thực nghiệm, Thầy truyền cho em tinh thần nghiên cứu khoa học, giúp em có động lực việc học tập nghiên cứu Em xin cảm ơn quý Thầy Cơ phịng thí nghiệm Hợp chất thiên nhiên nói riêng nhƣ q Thầy Cơ khoa Hóa học – trƣờng Đại học Sƣ phạm thành phố Hồ Chí Minh nói chung tận tâm cơng tác giảng dạy, truyền thụ cho em nhiều kiến thức khoa học hữu ích suốt thời gian em học tập trƣờng Cuối cùng, em xin gửi lời cảm ơn chân thành đến bạn Trần Thị Tú Quyên, bạn Nguyễn Thị Ngọc Nƣơng, chị Trần Thị Thu Sƣơng đồng hành em suốt thời gian qua 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 Xin chân thành cảm ơn 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Khóa luận tốt nghiệp Nguyễn Hữu Tồn MỤC LỤC MỤC CÁC KÝ HIỆU VÀ CHỮ VIẾT TẮT DANH MỤC CÁC BẢNG DANH MỤC CÁC SƠ ĐỒ DANH MỤC CÁC HÌNH DANH MỤC CÁC PHỤ LỤC LỜI MỞ ĐẦU CHƢƠNG TỔNG QUAN 1.1 ĐẶC ĐIỂM THỰC VẬT 1.1.1 Mô tả chung 1.1.2 Vùng phân bố 1.2 CÁC NGHIÊN CỨU VỀ DƢỢC TÍNH 1.2.1 Dƣợc tính theo y học cổ truyền 1.2.2 Nghiên cứu dƣợc tính 1.3 CÁC NGHIÊN CỨU VỀ THÀNH PHẦN HÓA HỌC CHƢƠNG THỰC NGHIỆM 12 2.1 HOÁ CHẤT, THIẾT BỊ, PHƢƠNG PHÁP 12 2.1.1 Hoá chất 12 2.1.2 Thiết bị 12 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 2.1.3 Phƣơng pháp tiến hành 12 2.2 NGUYÊN LIỆU 12 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 2.2.1 Thu hái nguyên liệu 12 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 2.2.2 Xử lý mẫu nguyên liệu 13 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e 2.3 ĐIỀU CHẾ CÁC LOẠI CAO 13 2.4 CÔ LẬP CÁC HỢP CHẤT HỮU CƠ TRONG CAO CHLOROFORM 14 d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 2.4.1 Sắc kí cột silica gel cao chloroform 14 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 2.4.2 Sắc kí cột silica gel phân đoạn A5 bảng 2.1 14 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 2.4.3 Sắc kí cột pha đảo phân đoạn A5.4 bảng 2.2 15 CHƢƠNG KẾT QUẢ VÀ THẢO LUẬN 17 CHƢƠNG KẾT LUẬN VÀ ĐỀ XUẤT 20 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 4.1 KẾT LUẬN 20 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 4.2 ĐỀ XUẤT 20 TÀI LIỆU THAM KHẢO 21 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Khóa luận tốt nghiệp Nguyễn Hữu Toàn MỤC CÁC KÝ HIỆU VÀ CHỮ VIẾT TẮT Ký hiệu, chữ viết tắt H-NMR 13 C-NMR HSQC Tiếng Anh Proton (1) Nuclear Magnetic Resonance Carbon (13) Nuclear Magnetic Resonance Heteronuclear Single Quantum Correlation HMBC Heteronuclear Multiple Bond Coherence s d t dd m  J ppm UV EA C Me Et H AcOH Ac SKC SKLM g mg MHz Hz cm mm m nm Singlet Doublet Triplet Double of doublet Multiplet Chemical shift Coupling constant Part per million Ultra Violet Ethyl Acetate Chloroform Methanol Ethanol n-Hexane Acetic acid Acetone Gam Miligam Mega Hertz Hertz Centimeter Milimeter Micrometer Nanometer Tiếng Việt Phổ cộng hƣởng từ hạt nhân proton (1) Phổ cộng hƣởng từ hạt nhân carbon (13) Phổ tƣơng tác dị hạt nhân qua liên kết Phổ tƣơng tác dị hạt nhân qua nhiều liên kết Mũi đơn Mũi đôi Mũi ba Mũi đơi đơi Mũi đa Độ chuyển dịch hố học Hằng số ghép spin Một phần triệu Tia cực tím Etyl axetat Clorofom Metanol Etanol Hexan Axit axetic Axeton Sắc ký cột Sắc ký lớp mỏng Gam 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e Mi-li-gam Me-ga-héc Héc 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 Xăng - ti- mét Mi-li-mét Mi-crô-mét Na-nô-mét 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Khóa luận tốt nghiệp Nguyễn Hữu Toàn DANH MỤC CÁC BẢNG Bảng 1.1 Các nghiên cứu thành phần hóa học Bảng 2.1 Sắc kí cột silica gel cao chloroform 14 Bảng 2.2 Sắc kí cột silica gel phân đoạn A5 15 Bảng 3.1 So sánh số liệu phổ hợp chất SJ1 hợp chất 5-pregnen-3,17,20-triol 19 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Khóa luận tốt nghiệp Nguyễn Hữu Toàn DANH MỤC CÁC SƠ ĐỒ Sơ đồ 2.1 Quy trình điều chế cao chloroform từ rễ Hà thủ ô trắng 13 Sơ đồ 2.2 Quy trình lập hợp chất 16 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Khóa luận tốt nghiệp Nguyễn Hữu Tồn DANH MỤC CÁC HÌNH Hình 1.1 Cây củ Hà thủ trắng Hình 3.1 Cấu trúc hợp chất SJ1 18 Hình 3.2 Một số tƣơng quan HMBC hợp chất SJ1 18 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Khóa luận tốt nghiệp Nguyễn Hữu Toàn DANH MỤC CÁC PHỤ LỤC  Phụ lục 1a Phổ 1H-NMR (MeOD) hợp chất SJ1  Phụ lục 1b Phổ 13C-NMR (MeOD) hợp chất SJ1  Phụ lục 1c Phổ HSQC (MeOD) hợp chất SJ1  Phụ lục 1d Phổ HMBC (MeOD) hợp chất SJ1 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Khóa luận tốt nghiệp Nguyễn Hữu Tồn Cao chloroform (400 gam) - Sắc kí cột silica gel - Giải ly H:EA, EA:Me:H2O - Cô quay thu hồi dung môi A1 3.6 g A2 5.0 g A3 5.6 g A4 8.4 g A5 A6 A7 A8 A9 A10 A11 A12 A13 6.0 g 8.4 g 13.0 g 19.6 g 26.8 g 31.0 g 41.2 g 53.0 g 71.6 g - Sắc kí cột silica gel - Giải ly Hexane:Ethanol A5.1 A5.2 A5.3 A5.5 A5.4 960 mg 882 mg 798 mg 950 mg 940mg - Sắc kí cột pha đảo, C-18 - Giải ly hệ MeOH:H2O 9:1 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 SJ1 122.5 mg df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 Sơ đồ 2.2 Quy trình lập hợp chất d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 16 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Khóa luận tốt nghiệp Nguyễn Hữu Tồn CHƢƠNG KẾT QUẢ VÀ THẢO LUẬN KHẢO SÁT CẤU TRÚC HỢP CHẤT SJ1 Hợp chất SJ1 (122,5 mg) thu đƣợc đƣợc từ phân đoạn A5.4 cao chloroform, có tính chất sau: - Dạng tinh thể hình kim, khơng màu, tan hồn tồn dung mơi methanol - Sắc kí lớp mỏng cho vết nhúng H2SO4 20% sấy nóng đến vết, bảng mỏng cho vết màu nâu rêu  Phổ 1H-NMR (MeOD): Phụ lục 1a  Phổ 13C-NMR (MeOD): Phụ lục 1b  Phổ HSQC (MeOD): Phụ lục 1c  Phổ HMBC (MeOD): Phụ lục 1d  BIỆN LUẬN CÁU TRÚC Phổ 1H-NMR hợp chất SJ1 (phụ lục 1a) cho thấy diện tín hiệu cộng hƣởng ba nhóm methyl H 1.19 (3H, d, J = 6.0 Hz); 0.8 (3H, s) 1.05 (3H, s) Trên phổ 1H-NMR cho thấy tín hiệu cộng hƣởng proton olefin H 5.37 (1H, m), hai proton methine gắn oxygen H 3.42 (1H, m) 3.80 (1H, dd, J = 6.3; 12.5 Hz) 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 Ngoài ra, phổ proton cịn có diện tín hiệu cộng hƣởng proton methylene 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 methine khoảng H 1.3 - 2.2 ppm df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b Phổ 13C-NMR hợp chất SJ1 (phụ lục 1b) cho thấy diện 21 carbon, gồm 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 có tín hiệu cộng hƣởng ba carbon methyl C 14.8 (C-18); 18.8 (C-21); 19.8 (C-19), 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 tám carbon methylene, sáu carbon methine có hai carbon methine gắn với oxygen d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b C 72.4 (C-3) C 72.9 (C-20), carbon methine olefin C 122.4 (C-6), bốn 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c carbon bậc bốn có carbon olefin C 142.3 (C-5), carbon gắn với oxygen C 87 (C-17) 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 Phổ HMBC hợp chất SJ1 (phụ lục 3d) cho thấy có tƣơng quan proton nhóm c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 methyl H 1.05 (3H, s, H-19) với carbon olefin C 142.3 (C-5) carbon C 38.6 (C- 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 1), 51.5 (C-9), 37.7 (C-10) Đồng thời proton olefin H 5.37 (1H, m, H-6) tƣơng quan với carbon C 33.2 (C-7), 33.3 (C-8), 37.7 (C-10) xác nhận diện liên kết đôi vị 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 trí C5-C6 Proton nhóm methyl H 1.19 (3H, d, H-21) tƣơng quan với hai carbon C 87 17 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Khóa luận tốt nghiệp Nguyễn Hữu Tồn (C-17); 72.9 (C-20) Đồng thời proton nhóm methyl H 0.8 (3H, s, H-18) tƣơng quan với carbon C 87.0 (C-17), 47 (C-13), 52.6 (C-14) xác nhận diện hai nhóm hydroxyl vị trí C-17 C-20 Các tƣơng quan HMBC lại đƣợc trình bày cụ thể Hình 3.2 Bảng 3.1 Từ số liệu phổ trên, kết hợp với so sánh tài liệu tham khảo (đƣợc trình bày Bảng 3.1) [12], cấu trúc SJ1 đƣợc đề nghị 5-pregnen-3,17,20-triol Hình 3.1 Cấu trúc hợp chất SJ1 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 Hình 3.2 Một số tƣơng quan HMBC hợp chất SJ1 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 18 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Khóa luận tốt nghiệp Nguyễn Hữu Tồn Bảng 3.1 So sánh số liệu phổ hợp chất SJ1 hợp chất 5-pregnen-3,17,20-triol Vị trí carbon Hợp chất 5-pregnen-3,17,20-triol (CD3)2CO Hợp chất SJ1 (MeOD) Loại carbon δH (ppm) δC (ppm) HMBC ( H⟶13C) δC (ppm) -CH2- 1.9; 1.1 (m) 38.6 38.3 -CH2- 1.58; 1.52 (m) 33.2 32.6 >CH-O- 3.42 (m) 72.4 71.1 -CH2- 2.25; 2.20 (m) 43.0 >C= - 142.3 =CH- 5.37 (m) 122.4 C-7; 8; 10 121.6 -CH2- 2.05; 2.0 (m) 32.3 C-5; 6; 8; 32.8 >CH- 1.52 (m) 33.3 C-7; 9; 14 32.8 >CH- 0.97 (m) 51.5 C-10; 11; 19 51.1 10 >C< - 37.7 11 -CH2- 1.5; 1.61 (m) 21.7 12 -CH2- 1.72; 1.8 (m) 32.4 31.9 13 >C< - 47.0 46.3 C-3; 5; 43.4 142.4 37.4 C-8; 9; 10; 13 21.4 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 14 >CH- 1.75 (m) 52.6 C-8; 13; 16; 18 52.2 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 15 -CH2- 2.08; 1.73 (m) 38.1 C-14; 16 38.6 16 -CH2- 1.76; 1.17 (m) 24.5 C-17 24.2 >C-O- - 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 17 87.0 85.8 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 18 -CH3 0.80 (s) -CH3 1.05 (s) >CH-O- 3.80 (q, J=6.3) 14.8 C-13; 14; 17; 14.4 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe 19 19.8 C-5; 9; 10 19.8 f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 20 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 72.9 C-21 72.2 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 21 -CH3 1.19 (d, J=6.0) c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e 18.8 C-17; 20 19.2 b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 19 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Khóa luận tốt nghiệp Nguyễn Hữu Toàn CHƢƠNG KẾT LUẬN VÀ ĐỀ XUẤT 4.1 KẾT LUẬN Từ mẫu rễ Hà thủ ô trắng thu hái đƣợc huyện Tịnh Biên, tỉnh An Giang, tơi khảo sát thành phần hố học cao chlorofom rễ Hà thủ ô trắng Bằng kỹ thuật sắc ký cột silica gel pha thƣờng, pha đảo, sắc ký lớp mỏng, cô lập đƣợc hợp chất: 5pregnen-3,17, 20-triol 4.2 ĐỀ XUẤT Trong thời gian tới tiếp tục khảo sát phân đoạn khác với hy vọng cô lập thêm hợp chất có cấu trúc Với mong muốn đóng góp chứng khoa học có giá trị Y học, tơi tiến hành thử nghiệm hoạt tính sinh học hợp chất cô lập đƣợc 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 f30 0647 0eaa75fb c03a6 cd1 296a7 baff2fde4fc88 c5d8 0e7e8 05c20 445 f057 6fba59ac8c4e 9bdf4e 2d37a 6e52e 4d1 fc0 d97e 52033 2486 b108 b 6ac85e 6b36 36b4 1df49 c267 c062 235bd48 0e9ed f9 dbd175b8eb7a 87444 0fa0 1dfe7 d7f7cf90a6 f92 74c81be 6be3 cbf7ee2 0416 0b53 5f5 7d8 c76 f1e6e 17e9 fe f3a8e f7a276 b2a0 4f9 2b17a 67137 b8a2 b5c136efb1e 7eaf7 81d1f4 316c593 d2c 0a2f44 210d1bfbcc3a7 35d5 1d13 f37 7b1 72d0 079b6dc0dfc35 e5ac1d8a5 f07 b5 ab5a5c1d67 622e0 44fd9c038a98 b3 f82 f5a071 7f5 9adefb04 4eeafe be3 c4c40e 54813e1 1a2e6a 6638e 29b2 0b7 c7e8a 1f7 92736 b1e8 c7ee ba292 7f7 2950 b4a90 b 87d180a 6f6 794a2 2d3 bb70a 4e2d2289aa8 df113fa 96d4 dd6 0d1 555e5 50f50086 24f6fb cc2 c3e2 d82a 7f4 2dc11d3 f7a8 4c9 d529 044 b7cfa91b4143 0b68 8aca f29 c5eac84c3f6 c86 c63 6c6 9f5ae 9f2 1f1 94c4b94 d1 c92e f3b8 8c4 e9b9a 3b5 cb2 8e b4a4b4 8b05 3489 bfa88 9d0 2057a9 3d2fb dd52 510 c0571 74e5 b5d0 9708 eb22 f03 1be6b6b5 d865 d19a15 7c0 c61 287d53f3bbef7 b31 c9b2 6f7 1494 f5a9 52c6be3 c9 9f937 3257 f26 5f9 43b5 6a1771 9851 f86 54481 0935 c52 003e be480 8c5 d5fba3e7 df50 b161 db0 3291ea f55 69f0537a9 e320 25a6bfdb6a95a68 c4 df2 df6e38a9 623 2b77ae3 f85 3222 3db95346 d300 0d8 68e6ddad9 20a7ba 014 ce7d06ee8 95a2fa e1 ab38e52 7a1f04aa55 bce 221d5ac4 2f1 4f8 b883 b9c08a42 99f2488 c61 c615 f54 f 9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 20 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Khóa luận tốt nghiệp Nguyễn Hữu Tồn TÀI LIỆU THAM KHẢO Tài liệu Tiếng Việt [1] Đỗ Tất Lợi (2004), Những thuốc vị thuốc Việt Nam, NXB Y học, 836-837 [2] Phạm Thanh Tâm, Trần Hùng (2002), Chuyên đề Nghiên cứu Khoa học Dƣợc, Y Học TP Hồ Chí Minh, 49-52 Tài liệu Tiếng Anh [3] Bui Xuan Hao, 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Merr., Asian Journal of Tranditional Medicines, 3(5), 193-198 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 688f0 1fc5a0 f29fe 01a1 f12bc58 e905 f3 c73b1d0e 18686 7c9 5c8 533 ccdd31 d8d 5ac1c03e9 7c0 9d11a 1e51fcb6a1e21 f59a 46c9796 d3ad0 16f5a324 85d6 6092 0b 85cbfd0 b14 f24 f71ee 04fbcfdd5 ed71 5fb4642 584d703 b0754 31c9d59 8785 e42 05bb4 6d10 f6a1 0a49fc87 4f4 ef7ff3 9e845fb 99d8 98157 b65 4c10 7b6 6e5e0 857 203076 c61 1f4 9f0 bca c3e09 e51 c452fb8 e3c6 26d5db4b01 0a9c3f7 752e7 b46e d9d2e cb4 2640a 78d3 1c7 88be 3195e d06 f227a 0a55e6 3c9 5c6 e5bdc8 493b45233 6241c8cf19 f4fe 18aca c143 58ed f87 5118 5b19 39fdd99 4c7 e0b6 5e9fca936 474 d600 f8f5a5205 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9a4dfb005aa 1c4 96bfb25 b1e0 d760 7750 67084 0577 2254fb1 58f03b2 d6b49817 080f1 60e2 d78 c3f57a67a b43d1d4 9e5d1 7ed5 3e3b57ad1 6592 cc4d62 b9aa8 7e3 d22c57008 165 f64e 080b2350 cf37f2d7a0 6aa0164 4b4aaa b383ae 0d92a cab8b5 f8d2 e7f0b0d5d0 c7b2466 32074 e7d5 dee c289 77f33ed0 b62 c2abcf2417 1c5 5ab 79a5e77a d2d6 c3 bc8e 88b1bde 442fe00d6c2 8da41 da9d0585 dc8aa 9f0 c70 f60 24 447b14 faea0 d730 d286 87a0ee 3e82 c349 609d215 f8355a d21 7fd8 774e8 99bf88 d54395a c02 c16 b196 cc74e0 c79 d3a2a7 c15aa 5b71 b9aa86 8194 7ac88 281e 8d76 b48182 8e6b398 c7a71a 5ee1 f02 Khóa luận tốt nghiệp Nguyễn Hữu Tồn Phụ lục 1a 6b4090 276 f85e 7e79a2 7b4 f9d31306 2ff9828 5326 33d3 1409 b83a2 1eabae5 c78 69b235 50a5 c3c862be85 c992 c8a9 d31 cc7 8eb5 4cfda56e 5e9a28 26f8fcf74 565 4bb45 0f2 178 f0e02 f11 f3 f858 dd7 e448a6 231fe65db2a88 2044 c48 1c3 5a24df6 bc9 b0bcf6 4689 7071a2 696e7 f15 1a28a c446 11fbd8 db86 80ef6b9 8cc9b6 74dc1 df3a6 b9d39e60 7c3 09863 4a0f18e f8e90e f5 f54e 4fe0e e17fc36 91491 3481e 6e 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