Structural Characterisation of Malonyl Flavonols in Leek (Allium porrum L.) Using High-performance Liquid Chromatography and Mass Spectrometry
Article first published online: 28 DEC 2013
Copyright © 2013 John Wiley & Sons, Ltd.
Volume 25, Issue 3, pages 207–212, May/June 2014
How to Cite
Donna, L. D., Mazzotti, F., Taverna, D., Napoli, A. and Sindona, G. (2014), Structural Characterisation of Malonyl Flavonols in Leek (Allium porrum L.) Using High-performance Liquid Chromatography and Mass Spectrometry. Phytochem. Anal., 25: 207–212. doi: 10.1002/pca.2493
- Issue published online: 14 APR 2014
- Article first published online: 28 DEC 2013
- Manuscript Accepted: 10 NOV 2013
- Manuscript Revised: 8 NOV 2013
- Manuscript Received: 17 MAR 2013
- structure elucidation;
- tandem mass spectrometry;
- malonyl flavonoid;
- Allium porrum
Vegetables contain a variety of phytochemicals that have the ability to modify enzymatic and chemical reactions, and therefore may have a positive influence on human health. In particular kaempferol is known to possess anti-carcinogenic activity.
The purpose of this work was to determine the structure of glycosylated kaempferol derivatives, acylated with malonic acid on the sugar portion.
A methanolic extract of the leaves of Allium porrum L. was submitted to fractionation procedures through semi-preparative HPLC/UV–MS techniques. The collected fractions were evaluated by accurate tandem mass spectrometry experiments using an electrospray ionisation (ESI) quadrupole time-of-flight instrument. Isolated compounds were hydrolysed in order to obtain information on the ester moieties.
The structures of five compounds not previously reported in leek were determined. The molecules are mono-hexose, di-hexose and coumaroyl, feruloyl and caffeoyl acylated di-hexose derivatives of kaempferol. The common characteristic of the structures relies on the presence of the malonyl moiety on the primary alcoholic function of the sugar immediately linked to the aglycone. Accurate tandem MS experiments and basic hydrolysis treatments revealed a sequence of the acylated glycosidic moieties.
A set of secondary metabolites of the aerial part of Allium porrum L. (leek) was identified and characterised by ESI/MS2. Knowledge of the presence of these first-reported compounds in leek could provide the means for fully understanding of the metabolism of this plant in relation to the biosynthesis of the phenolics. Copyright © 2013 John Wiley & Sons, Ltd.