Anthocyanins from red cabbage – stability to simulated gastrointestinal digestion

• Published in: Phytochemistry (Oxford) Vol. 68; no. 9; pp. 1285 - 1294
• Main Authors: McDougall, Gordon J., Fyffe, Stewart, Dobson, Pat, Stewart, Derek
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01.05.2007; Elsevier
• Subjects: Acylation; Anthocyanins; Anthocyanins - chemistry; Anthocyanins - isolation & purification; Anthocyanins - metabolism; Biological and medical sciences; Brassica - chemistry; Brassica oleracea; cabbage; Chemical constitution; digestion; Digestion - physiology; Fundamental and applied biological sciences. Psychology; gastrointestinal system; General pharmacology; Health benefits; Hydrogen-Ion Concentration; Hydroxycinnamic acids; In vitro digestion; Medical sciences; Molecular Structure; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant physiology and development; Polyphenols; Red cabbage; Stability; Stability; Polyphenols; Anthocyanins; In vitro digestion; Hydroxycinnamic acids; Red cabbage; Health benefits; Acylation; Anthocyanin; Molecular structure; Glucoside; Digestion; In vitro; Brassica oleracea var. capitata rubra; Polyphenol; Phenol; Cruciferae; Dicotyledones; Angiospermae; Phenols; Spermatophyta; Cinnamic acid(hydroxy)
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2007.02.004

The stability of red cabbage anthocyanins was assessed by an in vitro procedure that simulates human gastrointestinal digestion. Anthocyanins acylated with hydroxycinnamic acids were more stable than the unacylated forms with a marked difference in stability between different acylated hydroxycinnamic acids. Anthocyanins were the main polyphenol components in extracts of fresh and pickled red cabbage. The composition of anthocyanins in red cabbage was studied using liquid chromatography mass–spectrometry. Eleven major peaks absorbing at 520 nm were discerned, which represented 18 different anthocyanin structures. Another five minor anthocyanin components could be identified by searching at their respective m/ z values but only in anthocyanin-enriched concentrates produced by sorption to solid phase extraction matrices. The predominant anthocyanins were constructed of cyanidin-3-diglucoside-5-glucoside “cores” which were non-acylated, mono-acylated or di-acylated with p-coumaric, caffeic, ferulic and sinapic acids. Pelargonidin-3-glucoside and novel forms of cyanidin-3- O-triglucoside-5- O-glucoside di-acylated with hydroxycinnamic acids were also detected in extracts of raw red cabbage, commercially pickled red cabbage and anthocyanin-enriched concentrates. The stability of the anthocyanins to simulated gastrointestinal digestion was assessed. The anthocyanins were effectively stable in the acidic gastric digestion conditions but the total recovery after simulated pancreatic digestion was around 25% compared to around 100% recovery of phenol content. As anthocyanins make up the majority of red cabbage polyphenols, this suggested that anthocyanins broke down to form new phenolic components. The recovery of the individual anthocyanins was monitored by LC–MS n . All of the anthocyanins were reduced in content after pancreatic digestion but acylated forms were notably more stable than non-acylated forms. There was also a relationship between the type of acylated hydroxycinnamic acid and stability to pancreatic digestion.