Isolation and identification of trans-2- and trans-3-hydroxy-1,8-cineole glucosides from Alpinia galanga.
Three hydroxy-1,8-cineole glucopyranosides, (1R, 2R, 4S)- and (1S, 2S, 4R)-trans-2-hydroxy-1,8-cineole beta-D-glucopyranosides, and (1R, 3S, 4S)-trans-3-hydroxy-1,8-cineole beta-D-glucopyranoside, which are possible precursors of acetoxy-1,8-cineoles as unique aroma components, were isolated from the rhizomes of greater galangal (Alpinia galanga W.). Their structures were analyzed by FAB-MS and NMR spectrometry, and the absolute configulation of each aglycone was determined by using a GC-MS analysis with a capillary column coated with a chiral stationary phase. The composition of the diastereomers of (1R, 2R, 4S)- and (1S, 2S, 4R)-trans-2-hydroxy-1,8-cineole beta-D-glucopyranosides in the rhizomes was determined as 3:7 by a GC-MS analysis after preparing the trifluoroacetate derivatives of the glucosides.
Someya
Y
Y
Laboratory of Food Chemistry, Ochanomizu University, Tokyo, Japan.
Kobayashi
A
A
Kubota
K
K
D002240:Carbohydrate Sequence; D008401:Gas Chromatography-Mass Spectrometry; D005960:Glucosides / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment
D005960:Glucosides