Nakanishi T, Suzuki M
Pharmaceuticals Group, Nippon Kayaku Company, Ltd., 31-12, Shimo 3-Chome, Kita-ku, Tokyo 115-8588, Japan.
J Nat Prod. 1998 Oct;61(10):1263-7. doi: 10.1021/np980193s.
Fagaridine is a quaternary benzo[c]phenanthridine alkaloid, originally isolated from Fagara xanthoxyloides in 1973. The assigned structure of this alkaloid was 7-hydroxy-8-methoxy-5-methyl-2, 3-(methylenedioxy)benzo[c]phenanthridinium (1). We have synthesized this compound, coded NK109, aiming at a practical antitumor drug, and during synthetic studies we questioned the original assigned structure. Thus, we synthesized 8-hydroxy-7-methoxy-5-methyl-2, 3-(methylenedioxy)benzo[c]phenanthridinium (2), isomer of the assigned structure, and compared the spectroscopic data of both 1 and 2. The NMR data of 1 and 2 were very similar, but the UV spectra were completely different. The UV data for fagaridine agreed with these for 2; consequently, the true structure of fagaridine is 2, not 1.
法加立定是一种季铵型苯并[c]菲啶生物碱，最初于1973年从刺花椒中分离得到。该生物碱的指定结构为7-羟基-8-甲氧基-5-甲基-2,3-(亚甲二氧基)苯并[c]菲啶鎓（1）。我们合成了这种化合物，编码为NK109，旨在开发一种实用的抗肿瘤药物，并且在合成研究过程中，我们对最初指定的结构提出了质疑。因此，我们合成了指定结构的异构体8-羟基-7-甲氧基-5-甲基-2,3-(亚甲二氧基)苯并[c]菲啶鎓（2），并比较了1和2的光谱数据。1和2的核磁共振数据非常相似，但紫外光谱却完全不同。法加立定的紫外数据与2的一致；因此，法加立定的真实结构是2，而不是1。
