Planta Med 2012; 78(08): 834-837
DOI: 10.1055/s-0031-1298432
Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Simultaneous Determination of the Absolute Configuration of Twelve Monosaccharide Enantiomers from Natural Products in a Single Injection by a UPLC-UV/MS Method

Yan-Hong Wang
1   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS 38677, USA
,
Bharathi Avula
1   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS 38677, USA
,
Xiang Fu
2   Department of Pharmacognosy, School of Pharmacy, University of Mississippi, University, MS 38677, USA
,
Mei Wang
1   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS 38677, USA
,
Ikhlas A. Khan
1   National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS 38677, USA
2   Department of Pharmacognosy, School of Pharmacy, University of Mississippi, University, MS 38677, USA
3   Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia
› Author Affiliations
Further Information

Publication History

received 15 December 2011
revised 27 February 2012

accepted 12 March 2012

Publication Date:
24 April 2012 (online)

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Abstract

In natural product chemistry, it is often crucial to determine sugar composition as well as the absolute configuration of each monosaccharide in glycosides. An ultra-performance liquid chromatography method using both photodiode array (PDA) and mass spectrometry detectors (UPLC-UV/MS) was developed for qualitative analysis of the absolute configuration of monosaccharide enantiomers. Within a single injection, 16 monosaccharide derivatives including 6 pairs of aldose enantiomers (D/L-glucose, D/L-galactose, D/L-allose, D/L-arabinose, D/L-xylose, and D/L-fucose) and 4 other monosaccharides (L-rhamnose, 2-deoxy-D-glucose, 6-deoxy-D-glucose, and 2-deoxy-D-glalactose) were identified in less than 25 minutes. It was found that the structures of derivatives of sugar enantiomers correlated with retention time. Among derivatives of sugar enantiomers in the current study, the stereoisomer of R-configuration at C-3′ retained longer than the corresponding S-configuration isomer. The UPLC-MS method can increase sensitivity of detection of the saccharides by more than 10 times compared to previously reported methods. The one-pot reaction of monosaccharide with L-cysteine methyl ester and phenyl isothiocyanate is easily reproduced, clean, and relatively simple in a screw-capped reaction vial. The developed method was successfully applied for the analysis of different types of glycosides, viz., glycosides of triterpenes, steroids, and flavonoids, that commonly exist in nature. The absolute configurations of composed monosaccharides are clearly characterized from tested samples.