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Phytochem Anal. 2009 Sep-Oct;20(5):353-64. doi: 10.1002/pca.1133.

NMR and UPLC-qTOF-MS/MS characterisation of novel phenylethanol derivatives of phenylpropanoid glucosides from the leaves of strawberry (Fragaria x ananassa cv. Jonsok).

Author information

  • 1Department of Biosciences, University of Kuopio, Kuopio, Finland. kati.hanhineva@uku.fi

Abstract

INTRODUCTION:

Strawberry (Fragaria x ananassa) is rich in polyphenols, particularly anthocyanins, flavonols, condensed tannins and ellagic tannins. In addition to the fruits, the leaves of strawberry also contain a wide range of phenolic compound classes, but have not been investigated to the same extent as the fruit.

OBJECTIVE:

To characterise a metabolite group present in the leaves of strawberry, that was not amenable for identification based on earlier information available in the literature.

METHODOLOGY:

Methanolic extracts of strawberry leaves were analysed by UPLC-qTOF-MS/MS and iterative quantum mechanical NMR spectral analysis.

RESULTS:

The structures of phenylethanol derivatives of phenylpropanoid glucosides Eutigoside A ( F4) and its two isomeric forms 2-(4-hydroxyphenyl)ethyl-[6-O-(Z)-coumaroyl]-beta-D-glucopyranoside (F6) and 4-(2-hydroxyethyl)phenyl-[6-O-(E)-coumaroyl]-beta-D-glucopyranoside (F1) were resolved by NMR and UPLC-qTOF-MS/MS. In addition, two other derivatives of phenylpropanoid glucosides similar to Eutigoside A but possessing different phenolic acid moieties, namely Grayanoside A ( F5) and 2-(4-hydroxyphenyl)ethyl-[6-O-(E)-caffeoyl]-beta-D-glucopyranoside (F14), were similarly identified. Also, accurate characteristic coupling constants for the subunits are reported and their usefulness in structural analysis is highlighted.

CONCLUSION:

Chemical analysis of the leaves of strawberry (Fragaria x ananassa cv. Jonsok) resulted in the identification of a compound class, phenylethanol derivatives of phenylpropanoid glycosides, not previously found in strawberry.

PMID:
19425115
[PubMed - indexed for MEDLINE]
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