Structures of New and Known Cyanoglucosides from a North American Plant, Purshia tridentata DC.

Chemical and Pharmaceutical Bulletin
1994.0

Abstract

A new cyanoglucoside, purshianin (1), was isolated together with a known cyanoglucoside, menisdaurin (2a), from stems of Purshia tridentata DC. (Rosaceae) collected in Oregon, U.S.A. and the structure was established as (4S,6S)-(Z)-6-(β-D-glucopyranosyloxy)-4-hydroxy-2-cyclohexene-A¹,α-acetonitrile (1) based on chemical and spectral evidence. Notably, the absolute structure of 1 and the revised stereostructure (2), (4S6R)-(Z)-6-(β-D-1) glucopyranosyloxy)-4-hydroxy-2-cyclohexene-Λ¹,a-acetonitrile for menisdaurin were decided based on combined studies of difference NOE spectra and Dreiding model inspection.

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