Feruloyloacetone can be the main curcumin transformation product. (15th July 2019)

• Record Type: Journal Article
• Authors: Typek, Rafał; Dawidowicz, Andrzej L.; Bernacik, Katarzyna; Stankevič, Marek
• Is Part Of: Food chemistry. Volume 286(2019)
• Page Start: 136
• Page End: 140
• Publication Date: 2019-07-15
• Subjects: Feruloyloacetone -- Curcumin derivative -- Curcumin degradation -- Feruloyloacetone NMR spectra -- Feruloyloacetone MSn analysis; Food -- Analysis -- Periodicals; Food -- Composition -- Periodicals; 664
• DOI: 10.1016/j.foodchem.2019.01.194
• Languages: English
• ISSNs: 0308-8146

Abstract

Highlights: The transformation of curcumin to feruloyloacetone. The influence of pH on feruloyloacetone formation was examined. MS 2, HRMS and NMR analysis of feruloyloacetone. 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 h heating of alkaline or acidic curcumin solution, respectively. The structure of the identified feruloyloacetone was confirmed by MS n, 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.