MASS SPECTROMETRY AS AN AID FOR DETERMINING STRUCTURES OF NATURAL GLUCOSIDES

Mass spectral fragmentation patterns were determined for acetates of a number of glucosides of unequivocally known structure which have been isolated from the barks and leaves of trees of the family Salicaceae. All glucoside acetates, irrespective of size, indicated primary fragmentation at the C-1 bond, essentially similar to that found for completely acetylated glucose and methyl glucoside. In addition, the spectra of the acetates of glucosides with free phenolic groups demonstrated loss of acetyl as ketene either concurrently with or before the rupture of the C-1 bond. Presence or absence of ester substitution in the glucose moiety of the parent glucosides could thus be determined with certainty, and possible location of substitution is indicated by relative intensities of fragment peaks. © 1968.