Studies on the barks of the family salicaceae—xix

Studies of the Hot Water Extractives of the Bark and Leaves of Populus deltoides Bartr.

“…indicated that these fractions comprised essentially only these two components with only traces of other products. If desired, crystalline products could be obtained by chromatography on silica gel as described previously (1).…”

“…The major and important peaks of the mass spectrum with their relative intensities are noted in the Experimental. Although deltoidin pentaacetate is an isomer of the acetate of w-salicyloylsalicin, the mass spectra of the two compounds are entirely different (15 For personal use only. pentaacetate does not give the prominent peak at mle 331, which is characteristic of the acetates of all glucosides without glucose moiety substitution (15).…”

“…Although deltoidin pentaacetate is an isomer of the acetate of w-salicyloylsalicin, the mass spectra of the two compounds are entirely different (15 For personal use only. pentaacetate does not give the prominent peak at mle 331, which is characteristic of the acetates of all glucosides without glucose moiety substitution (15). Instead of mle 331 and related mle 271 and 21 1 peaks due to loss of acetic acids from the unsubstituted glucose acetate moiety, deltoidin pentaacetate exhibited a major peak at mle 451 corresponding with an acetylsalicyloyl ester of triacetylglucoseoxonium ion, and demonstrating that salicyloyl substitution in deltoidin is on the glucose moiety.…”

“…In an earlier study on the mass spectrometry of phenolic glucosides (15) it was demonstrated that the acetates of phenolic glucosides with aroyl substitution on the 6-0-glucose position gave much greater yields of ions corresponding with the loss of two acetic acids and one ketene than did the acetates of those with aroyl substitution on the 2-0-glucose position. In the case of monobenzoates of salicin and of w-salicyloylsalicin, the ion involved was that at mle 231, and the relative intensities were 19.2 and 1.0 for 6-0-benzoylsalicin and 2-0-benzoylsalicin, respectively, and 38.1 and 1.2 for 6-O-benzoyl-wsalicyloylsalicin and 2-0-benzoyl-w-salicyloylsalicin, respectively.…”

“…tree cut in Outagamie County, Wisconsin in June were extracted immediately with ethanol by the Waring Blendor technique (1). The hot water-soluble portions of the ethanol extractives were extracted fractionally with ethyl acetate, and the ethyl acetate-soluble fractions were chromatographed on columns of polyamide and eluted with water followed by 20% ethanol and 50% ethanol as employed in recent studies on the barks of other species (1,2). As in previous studies, all eluate fractions were monitored by means of t.l.c., concentrated to small volumes, allowed to stand, filtered if crystals separated, and finally freeze dried.…”