Isolation of two megastigmane-3,9-diol glucosides from Shiraz leaves

The water soluble methanol extract from Shiraz leaves, was passed through a XAD 2 column, and elution with methanol yielded a crude glycoconjugate com posite. Further separation of this polar fraction using HPLC semi preparati ve C-18 column followed by acetylation and flash chromatography yielded Ala ngioside J and a new norisoprenoid beta -D-glucopyranoside. Using H-1 and C -13-NMR techniques, the latter was shown to be the C-9 conjugate of the sam e (3S,5R,6S,9R)-megastigmane-3,9-diol as the C-3 conjugated former one.