25 ヤブコウジ科植物のベンゾキノン誘導体,とくにbis(benzoquinonyl)-olefine型化合物の構造

概要

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The distribution of hydroxybenzoquinone derivatives among Myrsinaceae plants growing in Japan has been examined and the presence of embelin (Ia), rapanone (Ib), maesaquinone (IIa), acetylmaesaquinone (IIb), and 2-hydroxy-5-methoxy-3-pentadecenyl(tridecenyl, tridecyl)benzoquinone (Va) and novel type bis(benzoquinonyl)-olefines, designated ardisiaquinones A (V), B (VI), and C (VII), was confirmed. Ardisiaquinones (V-VII), isolated from Ardisia sieboldii in respective yields of 0.02, 0.02, and 0.0005%, showed the similar properties and, from the formation of the derivatives (Chart 1) and from their spectroscopic properties (cf. Table 1), the partial formula (A) was put forward for these compounds. Mass (Table 2), IR and UV spectra suggested the positions of the substituents as shown in the formula (B) and the alkaline hydrogen peroxide oxidation afforded cis-octadec-9-en-1,18-dioic acid. Thus the structure of ardisiaquinones have been established as V, VI and VII. The structure has also been confirmed by the unequivocal synthesis of XIX shown in Chart 2. The biogenesis of the compounds will also be discussed.
天然有機化合物討論会の論文
1967-09-25