Dietary Flavonoid Aglycones and Their Glycosides: Which Show Better Biological Significance?

Abstract

The dietary flavonoids, especially their glycosides, are the most vital phytochemicals in diets and are of great general interest due to their diverse bioactivity. The natural flavonoids almost all exist as their O-glycoside or C-glycoside forms in plants. In this review, we summarized the existing knowledge on the different biological benefits and pharmacokinetic behaviors between flavonoid aglycones and their glycosides. Due to various conclusions from different flavonoid types and health/disease conditions, it is very difficult to draw general or universally applicable comments regarding the impact of glycosylation on the biological benefits of flavonoids. It seems as though O-glycosylation generally reduces the bioactivity of these compounds - this has been observed for diverse properties including antioxidant activity, antidiabetes activity, anti-inflammation activity, antibacterial, antifungal activity, antitumor activity, anticoagulant activity, antiplatelet activity, antidegranulating activity, antitrypanosomal activity, influenza virus neuraminidase inhibition, aldehyde oxidase inhibition, immunomodulatory, and antitubercular activity. However, O-glycosylation can enhance certain types of biological benefits including anti-HIV activity, tyrosinase inhibition, antirotavirus activity, antistress activity, antiobesity activity, anticholinesterase potential, antiadipogenic activity, and antiallergic activity. However, there is a lack of data for most flavonoids, and their structures vary widely. There is also a profound lack of data on the impact of C-glycosylation on flavonoid biological benefits, although it has been demonstrated that in at least some cases C-glycosylation has positive effects on properties that may be useful in human healthcare such as antioxidant and antidiabetes activity. Furthermore, there is a lack of in vivo data that would make it possible to make broad generalizations concerning the influence of glycosylation on the benefits of flavonoids for human health. It is possible that the effects of glycosylation on flavonoid bioactivity in vitro may differ from that seen in vivo. With in vivo (oral) treatment, flavonoid glycosides showed similar or even higher antidiabetes, anti-inflammatory, antidegranulating, antistress, and antiallergic activity than their flavonoid aglycones. Flavonoid glycosides keep higher plasma levels and have a longer mean residence time than those of aglycones. We should pay more attention to in vivo benefits of flavonoid glycosides, especially C-glycosides.

High‐power ultrasound altered the polyphenolic content and antioxidant capacity in cloudy apple juice during storage

“…The reduction in phenolic compounds during ultrasound treatment as well as during storage of sonicated juices might be prescribed to the sonochemically generated hydroxyl radicals. These radicals could enhance hydrolysis of the phenolic glycosidic moieties, thus promoting aglycon formation that are phenolic structures with lower stability than the corresponding glycosides compounds (Dias et al, ; Xiao, ). Also, nucleated cavitation bubbles that grew and collapsed during ultrasonic treatment, may be filled with water vapor or other gases that are dissolved in the apple juice.…”

A Method for Visualizing Fluorescence of Flavonoid Therapeutics in Vivo in the Model Eukaryote Dictyostelium Discoideum

“…The mechanisms for flavonoid influx into human cells have not been fully elucidated and observations have been reported to differ based on flavonoid, cell type and sample preparation, and this might equally apply to amoebae. There may be more passive diffusion of the less-polar aglycones [41] than of the more commonly found glycoside forms [51]. The extent of this is not known versus active transport and efflux, although our chemical inhibition studies suggest that flavonoid efflux is an active process (manuscript in preparation).…”

Efeito dos compostos fenólicos do camu-camu e do cupuaçu no desenvolvimento da obesidade e diabetes mellitus tipo 2

“…The inhibition of gut digestive enzyme activities, as well the modulation of receptors and nutrient transporters, have been described as adjuvants in the treatment against the alterations in glucose and lipids homeostasis (Williamsom, 2013;. Previously, a cupuassu extract showed potent inhibition of α-amylase activity and some flavones also showed strong inhibitory activity of α-glucosidase (Xiao, 2015), while flavan-3-ols apparently have stronger lipase inhibitory activity compared to other classes of polyphenols (Gonzales et al, 2015). In addition, flavan-3-ols have also the potential to modulate incretins as glucagon-like peptide-1 (GLP-1) and dipeptidyl-peptidase 4 (DPP4) activity in vitro (Gonzáles-Albuín et al, 2014), and reduce sugar absorption through the inhibition of the main transporters of glucose present in the intestinal epithelial cells .…”

“…As frutas, legumes e verduras fornecem compostos bioativos como fibras, vitaminas, minerais, carotenoides e compostos fenólicos que promovem benefícios à saúde e reduzem o risco de desenvolvimento dessas doenças (SLAVIN;LLOYD, 2012;TORRES-FUENTES et al, 2014). Entre estes diferentes compostos bioativos presentes nos vegetais, os compostos fenólicos destacam-se por suas propriedades antioxidante, antinflamatória, e mais recentemente por seus efeitos sobre a sinalização celular, a expressão gênica e a microbiota intestinal, mecanismos importantes na prevenção do desenvolvimento de diabetes tipo 2 e da obesidade (ANHÊ et al 2013HASSAN, 2010;XIAO;). …”

“…As frutas, legumes e verduras fornecem compostos bioativos como fibras, vitaminas, minerais, carotenoides e compostos fenólicos que promovem benefícios à saúde e reduzem o risco de desenvolvimento dessas doenças (SLAVIN;LLOYD, 2012;TORRES-FUENTES et al, 2014). Entre estes diferentes compostos bioativos presentes nos vegetais, os compostos fenólicos destacam-se por suas propriedades antioxidante, antinflamatória, e mais recentemente por seus efeitos sobre a sinalização celular, a expressão gênica e a microbiota intestinal, mecanismos importantes na prevenção do desenvolvimento de diabetes tipo 2 e da obesidade (ANHÊ et al 2013 HASSAN, 2010;XIAO; A insulina é um hormônio polipeptídico anabólico produzido pelas células β pancreáticas, cuja síntese é ativada pelo aumento dos níveis circulantes de glicose e aminoácidos após as refeições. Seus efeitos metabólicos imediatos incluem: aumento da absorção de glicose, principalmente em tecido muscular e adiposo; aumento da síntese de proteínas, ácidos graxos e glicogênio; bem como inibição da produção hepática de glicose, da lipólise no tecido adiposo e da proteólise no tecido muscular (FREITAS; CESCHINI; RAMALLO, 2014;.…”