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

2009; Wiley; Volume: 20; Issue: 5 Linguagem: Inglês

10.1002/pca.1133

1099-1565

Kati Hanhineva, Pasi Soininen, Mikko Anttonen, Hanna Kokko, Ilana Rogachev, Asaph Aharoni, Reino Laatikainen, Sirpa Kärenlampi,

Natural product bioactivities and synthesis

Abstract Introduction Strawberry ( Fragaria × 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]‐ β‐ d ‐glucopyranoside ( F6 ) and 4‐(2‐hydroxyethyl)phenyl‐[6‐ O ‐( e )‐coumaroyl]‐ β‐ 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]‐ β‐ 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 × ananassa cv. Jonsok) resulted in the identification of a compound class, phenylethanol derivatives of phenylpropanoid glycosides, not previously found in strawberry. Copyright © 2009 John Wiley & Sons, Ltd.