56 ハナミョウガの成分研究 : 一新セスキテルペンパーオキサイドhanalpinolの構造

概要

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The seeds of A. japonica (Zingiberaceae) have been used as an aromatic stomachic under the name, "Izu-shukusha", in Japan. From the fresh rhizomes of the plant, two new sesquiterpenes, 3α,4α-oxidoagarofuran(2) and hanalpinol(11) were isolated together with 4α-hydroxydihydroagarofuran(1), α-agarofuran(3), 10-epi-γ-eudesmol(4), β-eudesmol(5) and furopelargone B(15). The structure of (2) was elucidated by chemical correlation with (1). Hanalpinol(11) was obtained as a fairly stable oil. Chemical and physical evidences indicated that this compound is a novel sesquiterpene peroxide possessing the partial structure as shown in Fig. 1. Oxidation of (11) with pyridinium chlorochromate gave a crstalline α,β-unsaturated ketone(12), the structure of which was established by means of X-ray analysis. The IR spectrum of (11) revealed the presence of intramolecular hydrogen bond, and acid treatment of (11) resulted in the formation of furopelargone B(15). Therefore, the structure of hanalpinol can be illustrated as formula (11). It is noteworthy that some of the above sesquiterpenes have significantly antagonistic activities against histamine and barium chloride on excised guinea pig ileum.
天然有機化合物討論会の論文
1980-09-10