西加毒素(Ciguatoxin) 聚醚梯：4.Maitotoxin MTX Polyether ladder刺尾鱼毒素 平间正博 1992,114 Maitotoxin MTX Maitotoxin .Na Maitotoxin MTX ofTwo World Records 0Mw-342 ith 99 sl of en le bond-there are 2-6.32 61 Hirama M. Science 2001, 294: 1904. 平间正博 PNAS, 2004,101, 12013–12018. 西加毒素 (Ciguatoxin) After a twelve-year struggle, the total synthesis of ciguatoxin CTX3C has been achieved. 62 4. Maitotoxin MTX 刺尾鱼毒素 Murata, M.; Iwashita, T.; Yokoyama, A.; Sasaki, M.; Yasumoto, T. J. Am. Chem. Soc. 1992, 114, 6594 C164H256O68S2Na2 32 ether rings 聚醚梯: Polyether ladder 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' ' 63 Maitotoxin MTX MTX 属于典型的钙通道激动剂 LD50 50 ng/Kg, 毒性高于岩沙海葵 毒素9倍，比河豚毒素强200倍。 Ca2+ ion channel activator MTX is the largest and most toxic of all non-peptidic secondary metabolites. Murata M. Yasumoto T. Nat. Prod. Rep. 2000, 17, 293-314. Murata M. Yasumoto T. Chem. Rev. 1993, 93, 1897-1909. 64 Maitotoxin 代表着现代鉴定技术NMR-MS在天然产物化学结构研究中的应用水平 C164H256O68S2Na2 村田 道雄 65 Maitotoxin MTX 5 μg/100 Kg 1 mg kill 1 million mice C164H256O68S2Na2 (MW = 3422) with 99 elements of stereochemistry-98 stereogenic centers and 1 trisubstituted double bond-there are 299=6.3 × 100 000 000000 000 000 000000 000 000 possible stereoisomers. Holder of Two World Records 66