84(P-85) ロクショウグサレキン属の色素ザイリンデン類の構造と化学的性質(ポスター発表の部)

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The fungi, Chlorociboria species, have a beautiful blue-green color. The conspicuous color has been attracting attention for over two centuries (first report; Geffroy 1728). The main blue pigment is xylindein (1), the plane structure of which was determined independently by Edwards et al. and Blackburn et al. in 1965. We reinvestigated the xylindein structure to reveal its hitherto-unknown absolute configuration and its tautomeric structure. By the X-ray crystallographic heavy atom method analysis of the p-bromobenzylether derivative 4, the absolute configurations at C-2' and C-2" positions were assigned as S and S. Furthermore, the X-ray crystallographic analysis of 1 itself showed the proposed tautomer to be the proper one. Next we investigated the chemical property of xylindein. When dimethylxylindein (2) was subjected to irradiation conditions in acetic acid, a 1:1 mixture of dihydrodimethylxylindein (3) and the dimethylxylindein dimer (8) was obtained. This result clearly showed that xylindein should have a auto-redox property. Furthermore, other pigments were isolated from Chlorociboria sp. and their structures were determined. The whole extracts were methylated with diazomethane and the resulting mixture was separated by silica-gel column chromatograpy to afford several pigments, in which 3 and 8 were included. In addition, the new compounds, 1'-hydroxydimethylxylindein 9 and 1'-hydroxydihydroxylindein tetramethyl-ether 10, were also isolated.
天然有機化合物討論会の論文
2000-10-01

84(P-85) ロクショウグサレキン属の色素ザイリンデン類の構造と化学的性質(ポスター発表の部)

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