Identification of key constituent of sugar-smoking pigment and its photobleaching, antioxidant and antiproliferative properties. (September 2022)

• Record Type: Journal Article
• Authors: Zou, Yufeng; Zhang, Jianbo; Niu, Yumin; Liu, Dengyong
• Is Part Of: Food research international. Volume 159(2022)
• Publication Date: 2022-09
• Subjects: Sugar-smoking pigment -- Structural characterization -- Decoloration -- Antioxidant capacity -- Antiproliferative activity; Food -- Analysis -- Periodicals; Food industry and trade -- Periodicals; Food industry and trade -- Canada -- Periodicals; Food Technology -- Periodicals; Food -- Periodicals; Food-Processing Industry -- Periodicals; Aliments -- Industrie et commerce -- Périodiques; Aliments -- Industrie et commerce -- Canada -- Périodiques; Aliments -- Recherche -- Périodiques; Food industry and trade; Canada; Periodicals; Electronic journals; 664.005
• DOI: 10.1016/j.foodres.2022.111485
• Languages: English
• ISSNs: 0963-9969

Abstract

Graphical abstract: Highlights: The key constituent of sugar-smoking brown pigment was identified as 5-(α-D-glucopyranosyl-(1–6)-α-D-glucopyranosyloxymenthyl)-2-furancarboxaldehyde. The binding mode of pigment and protein on chicken skin was identified by molecular docking. Discoloration was mainly due to oxidation reaction followed by photobleaching. The pigment exhibited both radical scavenging and anti-proliferative ability. The pigment can be extracted from plants (like Rehmanniae Radix ) as an alternative to smoking technique to produce clean label sugar-smoked meat products. Abstract: The key constituent(s) of sugar-smoking brown pigments were identified, the chemical and biological properties were subsequently investigated, and the possibility of obtaining it from nature was explored. A pigment was isolated, which was identified as condensation product of 5-hydroxymethyl-2-furfuraldehyde (5-HMF) with glucose: 5-(α-D-glucopyranosyl-(1–6)-α-D-glucopyranosyloxymenthyl)-2-furancarboxaldehyde (5-GGMF). The molecular weight was 450.00. The interaction between pigment with protein on chicken skin was mainly via hydrogen and carbon-hydrogen bonds. It was obtained by caramelization instead of Maillard reaction. Discoloration of sugar-smoking pigments were mainly due to cleavage of chromophores caused by the oxidation reaction followed by photobleaching mechanism. Both radical scavenging and antiproliferative capacity of sugar-smoking pigment were in a dose-dependent manner. However, the IC50 values for HepG2 and PANC-1 cells differed by more than ten times. Since 5-GGMF is also present in plant resources (like Rehmanniae Radix ), it can be obtained as natural additive to produce clean label sugar-smoked meat products.