45 プレニルナフトキノン類縁体および関連アントラキノン類の生合成研究

概要

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The biosynthesis of prenylnaphthoquinone congeners and anthraquinones which are known to be biosynthesized via osuccinylbenzoic acid (OSB) has been studied using cell cultures. In order to clarify the stereochemical process of prenylation and the subsequent decarboxylation during the biosynthesis of naphthoquinone congeners occurring in Catalpa ovata G. Don (Bignoniaceae), the dilution analyses after administration of [1-carboxy-^<14>C]-OSB to cell cultures of the same plant were carried out. The results obtained by these experiments demonstrated that OSB is transformed, via 2-carboxy-4-oxo-1-tetralone (COT), stereospecifically to (2S)-2-prenyl-COT ((2S)-21) which is in turn transformed to (2R)-catalponone ((2R)-22), and that the latter is a key intermediate in the biosynthesis of prenylnaphthoquinone congeners. The mechanism of prenylation during the biosynthesis of lucidin primeveroside (30) was elucidated by locating the ^<13>C-label in the above glycoside isolated from cell suspension cultures of Galium mollugo L. (Rubiaceae), to which [1-carboxy-^<13>C]-OSB was administered. This mechanism was also supported by the isolation, from the same culture, of a glycoside of the possible intermediate (31).
天然有機化合物討論会の論文
1979-09-20