Aliphatic β-D-glucosides from fruits of Carica pubescens

Article abstract of DOI:10.1016/S0031-9422(97)00196-9

Ethyl 3-O-β-D-glucopyranosylbutanoate, butyl 3-O-β-D- glucopyranosylbutanoate and 3-oxo-octyl 1-O-β-D-glucopyranoside were isolated from Carica pubescens fruit pulp by liquid chromatography on XAD. Identifications were performed after peracetylation by comparison of HRGC and HRGC-mass spectral data with those of synthesized reference compounds. Chiral evaluation of glycosidically-bound 3-hydroxybutanoates and octane-1,3-diol was achieved by multidimensional gas chromatography, combining a polar achiral column (DB-Wax) with a chiral main column (heptakis-2,6-di-O-methyl- 3-O-pentyl-β-cyclodextrin/OV 1701 and 2.3-di-O-acetyl-6-O-tert-butyl- dimethylsilyl-β-cyclodextrin/OV 1701, respectively). Comparison of retention times of synthesized, optically-enriched reference compounds with enzymically-released aglycones revealed enantiomeric excesses of the (S)-3- hydroxybutanoates, i.e. 96% and 24%, for the ethyl and the butyl ester, respectively. Octane-1,3-diol exhibited an enantiomeric excess of (R)-90%.