12 ミソハギの新塩基Lythrancine-I〜IV及びLythrancepine-I〜IIIの構造について
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概要
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Seven new alkaloids, lythrancine-I〜IV and lythrancepine-I〜III, were isolated from Lythrum anceps Makino (Lythraceae). The i.r. and n.m.r. spectra of lythrancine-II, C_<29>H_<37>O_6N show the presence of a secondary acetoxy-, two aromatic methoxy- and two hydroxy-groups. Acetylation of lythrancine-II gave lythrancine-III, C_<31>H_<39>O_7N, and lythrancine-IV, C_<33>H_<41>O_8N, and alkaline hydrolysis of these three bases afforded lythrancine-I, C_<27>H_<35>O_5N. Both lythrancepine-II, C_<29>H_<37>O_5N, and lythrancepine-III, C_<31>H_<39>O_6N, on alkaline hydrolysis gave lythrancepine-I, C_<27>H_<35>O_4N. Lythrancine-III was converted into lythrancepine-I through its treatment with p-TsC1 in pyr. followed by LiAlH_4 reduction of the product. The foregoing chemical evidences show that these seven bases have the same skeleton. Treatment of lythrancine-II with phosgene readily gave 5-membered cyclic carbonate, which shows the presence of a cis-glycol in the molecule. One proton on each of two oxygenated carbons of the carbonate was recognized in the n.m.r. spectrum, thus, the original alcohols proved to be secondary. Lythrancine-II, on chromic acid oxidation, yielded 2,2'-dimethoxydipheny1-5,5'-dicarboxylic acid (IV), 4-methoxybenzene-1,3-dicarboxylic acid (V) and trans-6-carboxy-2-carboxymethylhexahydro-pyridine (VI), which were isolated as dimethyl esters. Jones' oxidation of lythrancine-III gave monoketone (XI), C_<31>H_<37>O_7N, and diketone (XII), C_<31>H_<35>O_8N. From the analysis of the n.m.r. spectrum of the latter (XII), structure (XIIa) was assigned to this compound. Then, the unique structures of seven natural bases were presented as shown in Chart 5.
- 天然有機化合物討論会の論文
- 1970-10-01
著者
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藤田 栄一
Osaka University Of Pharmaceutical Sciences
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藤田 栄一
京大化研
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藤田 栄一
Institute For Chemical Research Kyoto University
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佐伯 行一
京大化研
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