18 「軟紫根」中のプロスタグランジン生合成阻害成分について

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As a continuation of our studies on biologically active compounds contained in traditional medicinal drugs, we have investigated inhibitors of Prostaglandin(PG) biosynthesis contained in "Nan-Shikon", the root of Arnebia euchroma. In our previous screening, hot aquous extracts of "Nan-Shikon" showed significant inhibitory activity against PG synthesizing enzyme system prepared from rabbit renal medulla microsomes. It was found, however, that naphtha-quinones known as the main constituents of "Nan-Shikon" was not contained in the hot water extracts, so that the PG biosynthesis inhibitors would be different from the compounds isolated from "Nan-Shikon". Partition with solvent followed by repeated chromatography finally gave inhibitors of PG biosynthesis tentatively designated as NS-2(1), 3(2), 4(3), 6(5) and 7(4). NS-2(1) was identified to be a mixture of shikonofuran B and C which had been isolated from "Ko-Shikon", the root of Lithospermum erythrorrhizon. NS-7 was identified as de-O-methllasiodiplodin isolated formerly from a fungus, Lasiodiplodia theobroma. A question remains unsolved whether NS-7(4) is produced by the plant or by the contaminated fungi. The spectral data of NS-4(3) suggested that it is a new compound and a dehydroderivative of geranylhydroquinone. The structure of NS-4, named arnebinol, was finally established by X-ray crystallography as a new ansa-type monoterpenyl benzenoid. NS-6(5) is a orange coloured compound and its UV spectrum suggested it being a benzoquinone derivative. Structure investigation finally led to the conclusion that NS-6, named arnebinone, is a new monoterpenoid benzoquinone possessing a fused 6 membered ring arising from successive migration and cyclization of geranylhydroquinone. Inhibitory activity against PG biosynthesis is stronger in NS-7 and 2 than in NS-4 and 6. Structure of NS-3 which showed similar colour with NS-6 is under investigation.
天然有機化合物討論会の論文
1983-09-15

18 「軟紫根」中のプロスタグランジン生合成阻害成分について

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