92(P32) 中国産駱駝蒿(Peganum nigellastrum)より得られる新規アルカロイド成分の構造(ポスター発表の部)

概要

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Six new alkaloids were isolated from the aerial parts of Peganum nigellastrum along with twelve known alkaloids. The structures of the new compounds each named luotonins A (1), B (2), E (3), C (4), D (5), and F (6) were confirmed by spectroscopic evidence and chemical synthesis. Luotonins A (1), B (2), and E (3) were unique alkaloids having a pyrroloquinazolinoquinoline skeleton. Luotonins C (4) and D (5) were canthin-6-one derivatives, which was the first isolation of canthin-6-one type alkaloid from the genus Peganum. Luotonin F (6), 3-[3(H)-quinazolinone]carbonyl-quinoline, was also a unique alkaloid of the title plant. Total syntheses of all new compounds 1-6 were achieved by convenient way. Luotonin A (1) was synthesized by 3 steps through vasicinone (14) as a key intermediate. Canthin-6-one derivatives (4) and (5) were synthesized by a biomimetic way from harmine (16) coexisting with 4 and 5 in the same source. Luotonin F (6) was also synthsized by 6 steps from 3-formylquinoline as a starting material. These new compound 1-6 were tested cytotoxic activity against P-388 cells. Among them, luotonin A (1) was the most potent inhibitor (IC_<50> 1.8μg/mL).
天然有機化合物討論会の論文
1999-09-01