Adduct Formation of Acrolein with Cyanidin-3-O-glucoside and Its Degradants/Metabolites during Thermal Processing or In Vivo after Consumption of Red Bayberry

Abstract

Acrolein (ACR) derives from the external environment and the endogenous metabolism of organisms. It has super-reactivity and can induce various diseases. We investigated the capacity of cyanidin-3-O-glucoside (C3G) and its degradants/metabolites to capture ACR during thermal processing or in vivo. Our results indicated that both C3G and its degradants, including phloroglucinaldehyde (PGA) and protocatechuic acid (PCA), could efficiently trap ACR to form adducts, such as C3G–ACR, C3G–2ACR, PGA–ACR, PGA–2ACR, PCA–ACR, and PCA–2ACR. Additionally, these adducts were detected in commercial canned red bayberry products. The adducts of C3G and its metabolites conjugated with ACR, such as C3G–ACR, C3G–2ACR, PGA–ACR, and 4-hydroxybenzoic-acid–ACR (4-HBA–ACR), were also detected in mice feces treated with C3G by oral gavage, where the adduct level was dose-dependent. A similar pattern was observed in tests on human consumption of red bayberry. In human urine, only PGA–2ACR and 4-HBA–ACR, were found, whereas C3G–ACR, C3G–2ACR, myricetin-3-O-rhamnoside–ACR (M3R–ACR), PGA–2ACR, 4-HBA–ACR and ferulic acid–ACR (FA–ACR) were detected in human feces following administration of red bayberry. Our results are the first demonstration that C3G and its metabolites can capture ACR in vitro and in vivo (mice and humans) and present a novel strategy, the development of C3G as a promising ACR inhibitor.

Effects of hesperidin combined with synephrine on the capture of acrolein in a mouse model, or in humans by citrus consumption

“…Numerous studies have reported that natural polyphenols or flavonoids, such as phloretin, 12 epigallocatechin gallate, genistein, 13 cyanidin-3- O -glucoside, 14 cardamomin, and alpinetin, 15 can effectively scavenge ACR in vitro and in vivo , in both mice and humans. Additionally, our previous study demonstrated that curcumin in combination with quercetin synergistically inhibited ACR formation in roasted chicken wings.…”

Berry anthocyanins prevent α‐dicarbonyls and advanced glycation end product formation in phosphate‐buffered saline‐based model systems, cookie and ground pork

“…After supplementation with quercetin by oral gavage, the quercetin‐MGO adduct was detected in mouse urine and feces (Zhao et al., 2021). In addition, a recent study successfully identified the acrolein adducts of C3G and its metabolites in mouse feces and human urine and feces after the consumption of red bayberry (Song, Lu, Lu et al., 2021). It is important to note that D3G, D3R, C3G, and C3R could be detected in human plasma at 90 min after ingestion of blackcurrant juice (Nielsen et al., 2003).…”

Mechanism of action of anthocyanin on the detoxification of foodborne contaminants—A review of recent literature

“…Twenty male Institute of Cancer Research (ICR) mice were fed ACR with or without C3G, and the feces contained adducts of C3G and its metabolites conjugated with ACR. C3G and its degradants, such as phloroglucinaldehyde and protocatechuic acid (PCA), could readily bind ACR to generate adducts, such as C3G‐ACR, C3G‐2ACR, PGA‐ACR, PGA‐2ACR, PCA‐ACR, and PCA‐2ACR, which could be detected in feces and urine (Song et al., 2021a). In summary, these findings imply that the protective effect of anthocyanins is unique and that it may function as an ACR inhibitor.…”