Purification of monoterpenyl glycosides by gel-permeation and hydrophobic-interaction chromatography on polyacrylamide (Bio-Gel P-2)

Hydrophobic interaction of the aglycone of monoterpenyl glycosides with the polyacrylamide matrix of Bio-Gel P-2 greatly retards the elution of these substances when chromatographed in dilute aqueous sodium chloride. This hydrophobic interaction is eliminated by inclusion of 15% acetonitrile in the eluant, thereby permitting conventional gel-permeation chromatography. Combination of these techniques by sequential chromatography on the same Bio-Gel column, in the hydrophobic interaction mode followed by the gel-permeation mode, provides a simple, yet mild and highly selective procedure for the purification of monoterpenyl glycosides from crude plant extracts. Examination of the chromatographic properties of beta-D-glucopyranosides and beta-D-galactopyranosides of a number of acyclic, monocyclic, and bicyclic monoterpenols indicates that the extent of hydrophobic interaction is of diagnostic value in determining the nature of the aglycone.