30 高等植物におけるプレニルナフトキノン類の生合成研究

概要

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o-Succinylbenzoic acid (OSB), 2-carbomethoxy-4-hydroxy-α-tetralone, catalponone and the related substance variously labeled with ^<14>C and ^3H were administered to Catalpa ovata. Detailed examination of catalpalactone, catalponol and α-lapachones isolated from the plant revealed the following biosynthetic pathway: 2-Carboxy-4-hydroxy-α-tetralone formed by the reductive cyclization of OSB is subjected to prenylation and decarboxylation to give 2-epicatalponol, which undergoes epimerization giving catalponol. On the other hand, oxidation of 2-epicatalponol gives 2R-catalponone, which is further converted into catalpalactone and α-lapachones. On the basis of this pathway, the biosynthesis of 1-naphthylisopentyl ether, 2,2-dimethylnaphthochroman, nordihydrolapachenole, tetrahydrotectol etc. was also discussed. This route is highly suggestive of the biosynthesis of phylloquinone, menaquinones as well as anthraquinones such as alizarin and morindone.
天然有機化合物討論会の論文
1974-10-01