<i>C</i>-Glycosylflavonoids: Identification, Bioactivity and Synthesis

Rauter, Amélia P.; Lopes, Rui G.; Martins, Alice

doi:10.1177/1934578x0700201125

Cited by 22 publications

(17 citation statements)

References 109 publications

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“…Flavonoids may be present in plants in free form, but are more commonly derivatives that are synthesized by processes such as glycosidation, prenylation, acetylation, methylation, and polymerization, which affects their bioactivity [ 57 ]. The most common form of flavonoid derivatives are glycosides, frequently O-glycosides, and less frequently, C-glycosydes [ 58 ]. Modification may involve a single oligosaccharide, or in some cases, a polysaccharide moiety.…”

Section: Flavonoidsmentioning

confidence: 99%

The Role of Polyphenols in Abiotic Stress Response: The Influence of Molecular Structure

Šamec

Karalija

Šola

et al. 2021

Plants

365

224

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Abiotic stressors such as extreme temperatures, drought, flood, light, salt, and heavy metals alter biological diversity and crop production worldwide. Therefore, it is important to know the mechanisms by which plants cope with stress conditions. Polyphenols, which are the largest group of plant-specialized metabolites, are generally recognized as molecules involved in stress protection in plants. This diverse group of metabolites contains various structures, from simple forms consisting of one aromatic ring to more complex ones consisting of large number of polymerized molecules. Consequently, all these molecules, depending on their structure, may show different roles in plant growth, development, and stress protection. In the present review, we aimed to summarize data on how different polyphenol structures influence their biological activity and their roles in abiotic stress responses. We focused our review on phenolic acids, flavonoids, stilbenoids, and lignans.

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Section: Flavonoidsmentioning

confidence: 99%

The Role of Polyphenols in Abiotic Stress Response: The Influence of Molecular Structure

Šamec

Karalija

Šola

et al. 2021

Plants

365

224

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“…Based on their polyphenolic structure these C ‐glycosyl flavonoids are potent antioxidants. Furthermore, anti‐inflammatory, antiviral, antibacterial, anxiolytic and hypoglycemic effects have been found in various in vitro test systems 43. Due to their structural similarity the flavan‐3‐ol derivatives may exhibit related properties.…”

Section: Discussionmentioning

confidence: 99%

Flavan‐3‐ol C‐glycosides – Preparation and model experiments mimicking their human intestinal transit

Hasslauer

Oehme

Locher

et al. 2010

Molecular Nutrition Food Res

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In order to study the human intestinal transit of flavan-3-ol C-glycosides, several C-glycosyl derivatives were prepared by non-enzymatic reaction of (+)-catechin with α-D-glucose, α-D-galactose and α-D-rhamnose, respectively. In contrast to literature data, we propose that the reaction mechanism proceeds in analogy to the rearrangement of flavan-3-ols during epimerization under alkaline conditions. Four of the 12 synthesized flavan-3-ol C-glycosides were incubated under aerobic conditions at 37°C using saliva (2 min) and simulated gastric juice (3 h). To simulate human intestine, the C-glycosides were also incubated under anaerobic conditions at 37°C both in human ileostomy fluid (10 h) and colostomy fluid (24 h), respectively. The flavan-3-ol C-glycosides under study, i.e. (+)-epicatechin 8-C-β-D-glucopyranoside (1a), (+)-epicatechin 6-C-β-D-glucopyranoside (1d), (+)-catechin 6-C-β-D-galactopyranoside (2b), (+)-catechin 6-C-β-D-rhamnopyranoside (3b) were analyzed in the incubation samples by HPLC-DAD and HPLC-DAD-MS/MS. They were found to be stable in the course of incubation in saliva, simulated gastric juice and ileostomy fluid and underwent degradation in colostomy fluid. While the 6-C-β-D-glucopyranoside 1d was completely metabolized between 2 and 4 h, decomposition of the 6-C-β-D-galactopyranoside 2b reached only 16 ± 2% within 4 h of incubation. Linear degradation rates of 1d and 2b in colostomy fluid differed significantly. As microbial metabolism of flavan-3-ols is known not to be influenced by the stereochemistry of the aglycon, varying degradation rates are ascribed to the effect of the sugar moiety. Based on these results we assume that flavan-3-ol C-glycosides pass through the upper gastrointestinal tract (oral cavity, stomach and small intestine) unmodified and are then metabolized by the colonic microflora.

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“…Glycosylation also occurs frequently in nature, usually at position 3 or 7 ( Figure 1 A). Common carbohydrates attached include D-glucose, L-rhamnose, D-galactose, D-xylose and L-arabinose [ 3 , 4 ]. Using genistein as an example, the basic molecular structures of this flavonoid in the aglycone, glycoside and conjugated β-glycoside forms are illustrated in Figure 1 .…”

Section: Classification and Chemical Structures Of Flavonoidsmentioning

confidence: 99%

Understanding the Composition, Biosynthesis, Accumulation and Transport of Flavonoids in Crops for the Promotion of Crops as Healthy Sources of Flavonoids for Human Consumption

Cheng

et al. 2020

Nutrients

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Flavonoids are a class of polyphenolic compounds that naturally occur in plants. Sub-groups of flavonoids include flavone, flavonol, flavanone, flavanonol, anthocyanidin, flavanol and isoflavone. The various modifications on flavonoid molecules further increase the diversity of flavonoids. Certain crops are famous for being enriched in specific flavonoids. For example, anthocyanins, which give rise to a purplish color, are the characteristic compounds in berries; flavanols are enriched in teas; and isoflavones are uniquely found in several legumes. It is widely accepted that the antioxidative properties of flavonoids are beneficial for human health. In this review, we summarize the classification of the different sub-groups of flavonoids based on their molecular structures. The health benefits of flavonoids are addressed from the perspective of their molecular structures. The flavonoid biosynthesis pathways are compared among different crops to highlight the mechanisms that lead to the differential accumulation of different sub-groups of flavonoids. In addition, the mechanisms and genes involved in the transport and accumulation of flavonoids in crops are discussed. We hope the understanding of flavonoid accumulation in crops will guide the proper balance in their consumption to improve human health.

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C-Glycosylflavonoids: Identification, Bioactivity and Synthesis

Cited by 22 publications

References 109 publications

The Role of Polyphenols in Abiotic Stress Response: The Influence of Molecular Structure

The Role of Polyphenols in Abiotic Stress Response: The Influence of Molecular Structure

Flavan‐3‐ol C‐glycosides – Preparation and model experiments mimicking their human intestinal transit

Understanding the Composition, Biosynthesis, Accumulation and Transport of Flavonoids in Crops for the Promotion of Crops as Healthy Sources of Flavonoids for Human Consumption

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