Studies on nepalese crude drugs. XXVI. Chemical constituents of Panch Aunle, the roots of Dactylorhiza hatagirea D. Don.

From the dried roots of Dactylorhiza hatagirea, which are termed Panch Aunl e in Nepal, five new compounds called dactylorhins A, B, C, D and E, and tw o new natural compounds named dactyloses A and B, have been isolated togeth er with twelve known compounds. In addition to these compounds, two kinds o f lipid mixture were also obtained. The structures of the new compounds have been determined by spectroscopic a nd chemical methods as follows: dactylorhin A, (2R)-2-beta-D-glucopyranosyl oxy-2-(2-methylpropyl)butanedioic acid bis(4-beta-D-glucopyranosyloxybenzyl ) ester; dactylorhin B, (2R,3S)-2-beta-D-glucopyranosyloxy-3-hydroxy-2-(2-m ethylpropyl)butanedioic acid bis(4-beta-D-glucopyranosyloxybenzyl) ester; d actylorhin C, (2R)-2-beta-D-glucopyranosyloxy-2-(2-methylpropyl) butanedioi c acid; dactylorhin D, (2R,3S)-2-beta-D-glucopyranosyloxy-3-hydroxy-2-(2-mr thylpropyl)butanedioic acid 1-(4-beta-D-glucopyranosyloxybenzyl) ester; dac tylorhin E, (2R)-2-beta-D-glucopyranosyloxy-2-(2-methylpropyl)butanedioic a cid 1-(4-beta-D-glucopyranosyloxybenzyl) ester; dactylose A, 1-deoxy-1-(4-h ydroxyphenyl)-L-sorbose; dactylose B, 1-deoxy-1-(4-hydroxyphenyl)-L-tagatos e. Although a mixture of dactyloses A and B has been already syntheshed, this is the first example of their isolation from natural resources. Dactyloses A and B were suggested to be biosynthesized from L-ascorbic acid and 4-hydroxybenzyl alcohol via 2-C-(4-hydroxybenzyl)-alpha-L-xylo-3-ketoh exulofuranosono-1,4-lactone.