Abstract

Research on the bioavailability of anthocyanins has focused, historically, on the non-flavonoid (C6-Cn) products that arise from anthocyanins in vivo. However, this review focuses on the products of anthocyanins that still possess the flavonoid structure (C6-C3-C6). Described herein are aspects of the in vivo pool of C6-C3-C6 anthocyanin-derived intermediates. Properties related to molecular size, shape, and polarity conveyed by six major anthocyanidin structures are discussed. The presence of a glycoside or not, and a variety of possible phase 2 conjugates, gives rise to a chemically diverse pool of C6-C3-C6 intermediates. Chemical properties influence the in vivo stability of anthocyanin-derived products, as well as their suitability as a substrate for xenobiotic conjugation and transport, and their association with the biomatrix. The flavonoid structure is associated with bioactivity and the particular properties of these C6-C3-C6 products of anthocyanins determines their deposition in the body, which may influence in vivo processes and ultimately health outcomes.

Highlights

  • Anthocyanidin pigments (Figure 1) are widely distributed in fruit, especially berries, and can be the most abundant flavonoid in deeply pigmented berry crops like blueberries

  • When anthocyanin anthocyanins have been very well-studied [19], this review focuses on the C6 -C3 -C6 -based products, 13C-labelled cyanidin-3-glucoside (C3g), rapid and was investigated in a human study using which are worthy of attention, owing to their well-documented bioactivities [1,2]

  • When the relative in vitro stabilities of the three glucosides of cyanidin, delphinidin, pelargonidin and their aglycones were compared at neutral pH, B-ring structures with greater hydroxylation were associated with decreased stability [20]

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Summary

Introduction

Anthocyanidin pigments (Figure 1) are widely distributed in fruit, especially berries, and can be the most abundant flavonoid in deeply pigmented berry crops like blueberries. There are several research, it is agreed that the concentration of parent anthocyanins in vivo would be too low to metaexert analyses that associate greater anthocyanin intake with reduced cardiovascular disease risk [6,7,8,9,10]. ADME was investigated in a human study using 13 C-labelled cyanidin-3-glucoside (C3g), rapid and cardiovascular and metabolic function, anthocyanin intake associated with a of delayed complete anthocyanin breakdown was demonstrated when is a significant proportion the 13 Cdecline. When anthocyanin anthocyanins have been very well-studied [19], this review focuses on the C6 -C3 -C6 -based products, 13C-labelled cyanidin-3-glucoside (C3g), rapid and ADME was investigated in a human study using which are worthy of attention, owing to their well-documented bioactivities [1,2].

Anthocyanin
Membrane Solubility of Anthocyanins
Anthocyanin Association with Human Serum Albumin
Anthocyanins in the Intestinal Tract
Uptake of Parent Anthocyanins on the Bilitranslocase
Parent Anthocyanin Conversion into C6 -C3 -C6 Products in Vivo
Deglycosylation
First-Pass Metabolism
Enterohepatic Circulation
Factors Affecting EHC Uptake
Flavonoids in EHC
Anthocyanins and EHC
Structural Specificity in Anthocyanin’s Behavior in Vivo
Cyanidin Metabolism and Products
Malvidin Metabolism and Products
Pelargonidin Metabolism and Products
Anthocyanins in Tissues
Anthocyanin Beyond the Blood Brain Barrier
The Pool of Anthocyanin Products in the Body
Slow Clearance of C6 -C3 -C6 Metabolites from Human Urine
How C6 -C3 -C6 Products from Anthocyanins May Work in Vivo
Methods to Study Anthocyanin Bioavailability
Findings
10. Conclusions
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