秋水仙素与无籽西瓜 Digitoxigenin:One of the Most Ingested Drugs in Medicine [活性】制痛细胞的生长，制胞有丝分夏 我水仙会运装广美应用于和地本、速传学的得究来拉物有钟的工作中 Molecules that Changed the World Nature Is A Great Architecture 天然产物极大地丰言了化学结构库 壁彩皆通 ” 密零 Nature,An Excellent Synthetic Chemist4 秋水仙素与无籽西瓜 O N H H3CO H3CO H3CO CH3 O OCH3 木原 均 Hitoshi Kihara 秋水仙碱 Colchicine  ［来源］百合科植物秋水仙Colchicum autumnale、老鸦 瓣Tulipa edulis、 丽江山慈菇Iphigenia indica鳞茎等。  ［活性］抑制癌细胞的生长。抑制细胞有丝分裂。 秋水仙素还被广泛应用于细胞学、遗传学的研究和植物育种的工作中。 1820 Digitoxigenin is a cardenolide isolated from Digitalis purpurrea and Digitalis lanata (Foxglove). These cardiac glycosides are the only inotropic drugs suitable for chronic treatment of congestive heart failure. ￾ Inhibit HT-1080 cell line growth, and show cytotoxic activities against breast and lung cancer cell lines. Digitoxigenin: One of the Most Ingested Drugs in Medicine O OH H O O Digitoxin R=H Digoxin R=OH H H O HO O O O OH O OH HO R HO OH H O O Digitoxigenin H H 洋地黄毒苷元 洋地黄毒苷和地高辛 充血型心力衰竭 1930 大自然是位神奇的化学家，合成了许许多多形形色色结构复杂的天 然产物，它们在人类医学发展史上扮演了非常重要角色，曾诞生了许多 影响人类历史进程和命运的重要小分子，aspirin, morphine, quinine, steroidal contraceptives, digoxin, penicillin, streptomycin, cyclosporin, taxol, vinblastine, ginkgolides, artemisinin and lavastatin and so on，这些 分子说明了天然产物具有巨大的历史作用和未来发展潜力。在现代药物 研究中，每一次具有轰动效应的药物的出现一般都伴随着一种新类型天 然产物的发现，同时也推动了有机化学和生命科学的发展。 Molecules that Changed the World O O OH O O OH HO HO HO HO OH OHC NH NH2 HN HN H2N NH NHMe O O O O H CH3 H CH3 O H H3C Artemisinin C C O NH N S H H H COOH H H O O O O HO O Lovastatin Penicillin Streptomycin Nature Is A Great Architecture Nature Is A Great Architecture 天然产物极大地丰富了化学结构库 N OH O CH3 OH O Ph O HO H3C O O H3C O H3C O H3C O CH3 Aconitine O O O O O CH3 H3C H3C Qinghaosu O O O O HO O O HO O HO H OH H H N H N OO OH H NH HO OH HO OH H OH OH OH OAc AcO H HO O H MeO2C O O O O OH O H AcO O O H OH CO2Me OH N N O O H H H H H N N OH OH H H CH3 Ajmaline N O H3CO OH CH3 Ryanodine H3C CH3 O O O NH HO HO HO OH HO HO CH3 CH3 OCH3 O H H H Echinopine B N O O N N OH OH O H3C Morphine O O H O OAc HO H Maoecrystal Z O O O O O CO2CH3 O Khayasin Ginkgolide C Metaphanine O OH Azadiractin H N CH3 H3C O NH2 Huperzine A N H N O O H3C Gelsemine OH OH OH Vinigrol Tetrodotoxin Strychnine Zoanthamine N O O O O O CH3 H3C CH3 CH3 CH3 CH3 H H H H CH3 H H3C CH3 HO AcO H O CH3 H O O O H OH OAc H O O OH H N O Ph H H H Taxol Taxane Nature, An Excellent Synthetic Chemist Nature, An Excellent Synthetic Chemist Maitotoxin 刺尾鱼毒素 比河豚毒素强200倍 O O O O O O O O O O O O O OH O O O OH O O O O HO OH O OH S O O ONa HO OH OH OH OH OH O S O ONa HO OH O H H H H H H H HO H H H H H H H H OH OHH H H H H H OH H OH HO OH H H OH H H OH OH H H HO H H H H H O O O O O O O OH H H H H H H H H H HO H A B C D E F G H I J K L M N P Q R S T U V Y X W 51 52 O O O O O HO OH H H H H H H O Z A' B' D C' ' F E' ' 村田 道雄 安元 健