49 キササゲのcatalpalactoneおよび類縁物貭の生合成研究

概要

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Catalpalactone (1), a phthalide in Catalpa ovata wood has been assumed to be biosynthesized via deoxylapachol (2) (or its equivalent) judging from the structure. Actually, besides 1 five naphthoquinones and catalponol (8), a hydrogenated naphthoquinone have been isolated from the Catalpa wood. Accordingly, (arom. carboxy-^<14>C]-o-succinylbenzoic acid (14) synthesized employing Cu^<14>CN, o-succinylbenzoic acid (14) and deoxylapachol (2) labeled by the Wilzbach method were administered to the Catalpa ovata plant. Catalpalactone (1) and catalponol (8) isolated from the plant were subjected to several degradation reactions which revealed that both compounds are biosynthesized via o-succinylbenzoic acid (14) or shikimate. It was also established that the phthalide carbonyl group of catalpalactone (1) originates from the carboxyl group of shikimic acid.
天然有機化合物討論会の論文
1973-10-01