Coumarins of Smyrniopsis aucheri

Abstract

Chemical transformations and spectral characteristics have enabled us to establish the structure and configurations of three coumarins: (+)-2′,2′-dimethyl-3′β-hydroxy-3′,4′-dihydropyrano(5′,6′:6,7)coumarin (I); (+)-4′β-hydroxy-5′β-(1-hydroxy-1-methylethyl)-4′,5′-dihydrofuro(2′,3′:6,7)coumarin (II); and (+)-4′β-hydroxy-5′-(1-glucopyranosyloxy-1-methylethyl)-4′,5′-dihydrofuro(2′,3′:6,7)-coumarin (III) isolated from the roots ofSmyrnopsis aucheri Karjag. This is the first time that these compounds, which have been called smyrinol, smyrindiol, and smyrindioloside, have been detected in nature.