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Feruloyloacetone can be the main curcumin transformation product

Author:
Typek, Rafał, Dawidowicz, Andrzej L., Bernacik, Katarzyna, Stankevič, Marek
Source:
Food chemistry 2019
ISSN:
0308-8146
Subject:
Curcuma longa, bioactive properties, curcumin, ferulic acid, food processing, foods, heat, mass spectrometry, nuclear magnetic resonance spectroscopy, temperature, vanillin
Abstract:
Curcumin is a phenolic compound produced by some plants, among which Curcuma longa is the reachest in this principal curcuminoid. At elevated temperature curcumin degrades to trans-6-(4’-hydroxy-3’-methoxyphenyl)-2,4-dioxo-5-hexenal, vanillin, ferulic acid and feruloylmethane, however, the formation of feruloyloacetone ((5E)-6-(4-hydroxy-3-methoxyphenyl)hex-5-ene-2,4-dione) in the curcumin degradation process has not been reported yet. As results from experiments, even 28.8% or 20.6% of the degraded curcumin is transformed to feruloyloacetone during 2 hrs heating of alkaline or acidic curcumin solution, respectively. The structure of the identified feruloyloacetone was confirmed by MSn, HRMS and NMR data. The presented results are important for food processing as feruloyloacetone is formed during food products preparation and its biological activity has not been fully recognized.
Agid:
6309806