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United States Department of Agriculture

Agricultural Research Service

Research Project: Discovery and Development of Natural Product-based Weed Management Methods

Location: Natural Products Utilization Research

Title: Simultaneous determination of the absolute configuration of twelve monosaccharide enantiomers from natural products in a single injection by UPLC-UV/MS method

Authors
item Wang, Yan-Hong -
item Avula, Bharathi -
item Fu, Xiang -
item Khan, Ikhlas -

Submitted to: Planta Medica
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: March 12, 2012
Publication Date: April 24, 2012
Citation: Wang, Y., Avula, B., Fu, X., Khan, I.A. 2012. Simultaneous determination of the absolute configuration of twelve monosaccharide enantiomers from natural products in a single injection by UPLC-UV/MS method. Planta Medica. 78:834-837.

Interpretive Summary: This manuscript presents an developed ultra performance liquid chromatography and a mass spectrometric(UPLC-UV/MS method for the characterization of 6 pairs of aldose enantiomers and 4 other monosacchrids in a single run within 23 minutes. It is the first method combining UPLC and MS techniques to deal with separation of multi-aldose enantiomers in a single injection. In this study, it was found that the structures of sugar enantiomers and their retention times were correlated. The absolute configuration at C-3' had a significant influence on the elution order of diastereoisomers. The developed method is fast and sensitive. It is useful for determination of sugar configuration of glycosides in natural product chemistry, and for qualification of dietary products that are used for substitution of sugars.

Technical 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. Within a single injection, 16 monosaccharide derivatives including 6 pairs of aldose enantiomers and 4 other monosaccharides were identified in less than 25 minutes. It was determined that the structures of derivatives of sugar enantiomers correlated with retention time. 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 of glycosides, viz., glycosides of triterpenes, steroids and flavonoid which commonly exist in nature. The absolute configurations of composed monosaccharides are clearly characterized from tested samples.

Last Modified: 4/17/2014
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