Modification of flavonoids: methods and influences on biological activities

Li, Changhong; Dai, Taotao; Chen, Jun; Chen, Ming‐Shun; Liang, Ruihong; Liu, Chengmei; Du, Liqing; McClements, David Julian

doi:10.1080/10408398.2022.2083572

Cited by 12 publications

(12 citation statements)

References 194 publications

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“…Flavonoids are usually poorly soluble in aqueous solutions, and the effect is dependent on the type and number of sugar moieties [ 4 , 5 , 6 ]. As expected, quercetin showed the highest partition coefficient, reflecting a higher degree of lipophilicity, while the partition coefficient observed for rutin indicated a higher degree of hydrophilicity.…”

Section: Discussionmentioning

confidence: 99%

“…These results were in agreement with those described in the literature [ 17 , 18 , 19 ]. Together with being slight less soluble in water, flavonoids bound to rhamnosyl need to be hydrolyzed by the colonic microbiota to allow aglycone release and, hence, absorption, while glucoside derivatives can be absorbed in the small intestine [ 4 , 5 , 6 , 18 ]. In this context, the enzymatic hydrolysis of rhamnosyl derivatives, such as rutin, is a good strategy to increase the bioavailability.…”

Section: Discussionmentioning

confidence: 99%

“…Several biological effects, such as anti-inflammatory, atheroprotective, antioxidant and anti-proliferative activities, have been described for Q3G. The beneficial effects can also be attributed to the increased blood level of quercetin detected after Q3G consumption [ 4 , 5 , 6 , 7 , 8 ]. A previous study of our research group evaluated α-L-rhamnosidases (hesperidinase from Penicillium sp.…”

Section: Introductionmentioning

confidence: 99%

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Enzymatic Hydrolysis of Rutin: Evaluation of Kinetic Parameters and Anti-Proliferative, Mutagenic and Anti-Mutagenic Effects

Sobreiro

Torre

Araújo

et al. 2023

Life

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The bioavailability of glucoside flavonoids is influenced by the nature of the sugar, glucosides being absorbed faster than rhamnoglucosides, for example. One strategy to enhance the bioavailability is enzymatic hydrolysis. In this study, some kinetic parameters of hesperidinase-mediated hydrolysis of rutin were evaluated using an UHPLC/QTOF-MSE analysis of the products of a bioconversion reaction. The resulting hydrolyzed rutins (after 4, 8 and 12 h of reaction) were submitted to anti-proliferative and Cytokinesis-Block Micronucleus (CBMN) assays in CHO-K1 cells. In the hesperidinase-mediated hydrolysis, the final concentration of quercetin-3-O-glucoside (Q3G) was directly proportional to the rutin concentration and inversely proportional to the reaction time. At an anti-proliferative concentration (2.5 μg/mL), hydrolyzed rutin derivatives did not show a mutagenic effect, except for the sample with a higher content of Q3G (after 4 h of the enzymatic hydrolysis of rutin). Moreover, the higher Q3G content in hydrolyzed rutin protected the CHO-K1 cells 92% of the time against methyl methanesulfonate-induced mutagenic damage. These results suggested that the anti-mutagenic effect of hydrolyzed rutin might be related to antioxidant and cell death induction. Presenting a good lipophilicity/hydrophilicity ratio, together with antioxidant and anti-mutagenic activities, the hesperidinase-mediated hydrolyzed rutin seemed to be a promisor raw material for the development of food supplements.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Enzymatic Hydrolysis of Rutin: Evaluation of Kinetic Parameters and Anti-Proliferative, Mutagenic and Anti-Mutagenic Effects

Sobreiro

Torre

Araújo

et al. 2023

Life

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“…The flavonoid nucleus with more hydroxyl groups is held up in the hydrophobic cavity because hydrophilicity rises with the number of hydroxyl groups [18,74,75]. The antioxidant activity is decreased by altering the methylation of the free hydroxyl groups on ring B. Methoxyl flavonoid derivatives have higher antioxidant activity due to flavonoid-flavonoid interaction [76,77].…”

Section: Role and Function Of Flavonoids As A Protective Preventive A...mentioning

confidence: 99%

Flavonoids Biosynthesis in Plants as a Defense Mechanism: Role and Function Concerning Pharmacodynamics and Pharmacokinetic Properties

Nabil-Adam¹,

Elnosary²,

Ashour³

et al. 2023

Flavonoid Metabolism - Recent Advances and Applications in Crop Breeding

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Flavonoids are a major class of secondary metabolites that comprises more than 6000 compounds that have been identified. They are biosynthesized via the phenylpropanoid metabolic pathway that involves groups of enzymes such as isomerases, hydroxylases, and reductases that greatly affect the determination of the flavonoid skeleton. For example, transferase enzymes responsible for the modification of sugar result in changes in the physiological activity of the flavonoids and changes in their physical properties, such as solubility, reactivity, and interaction with cellular target molecules, which affect their pharmacodynamics and pharmacokinetic properties. In addition, flavonoids have diverse biological activities such as antioxidants, anticancer, and antiviral in managing Alzheimer’s disease. However, most marine flavonoids are still incompletely discovered because marine flavonoid biosynthesis is produced and possesses unique substitutions that are not commonly found in terrestrial bioactive compounds. The current chapter will illustrate the importance of flavonoids’ role in metabolism and the main difference between marine and terrestrial flavonoids.

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“…According to the D-value of the heat of formation (△ HOF) and radical scavenging rete examination (including DPPH, ABTS and FRAP test), the anti-oxidative activity of flavonoid compounds is closely related to their structures [ 50 ]. The main structural factors affecting the anti-oxidative activity of flavonoids includes the number and location of the hydroxyl, ring-C yoke system, the glycoside or methylation of the hydroxyl, the lipid solubility and charge distribution [ 51 , 52 ].…”

Section: Chemical Structure and Anti-oxidative Activity Of Flavonoidsmentioning

confidence: 99%

Potential therapeutic use of plant flavonoids in AD and PD

Meng-zhen

Zhang

et al. 2022

Heliyon

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Modification of flavonoids: methods and influences on biological activities

Cited by 12 publications

References 194 publications

Enzymatic Hydrolysis of Rutin: Evaluation of Kinetic Parameters and Anti-Proliferative, Mutagenic and Anti-Mutagenic Effects

Enzymatic Hydrolysis of Rutin: Evaluation of Kinetic Parameters and Anti-Proliferative, Mutagenic and Anti-Mutagenic Effects

Flavonoids Biosynthesis in Plants as a Defense Mechanism: Role and Function Concerning Pharmacodynamics and Pharmacokinetic Properties

Potential therapeutic use of plant flavonoids in AD and PD

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