2009
DOI: 10.3390/ijms10115002
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Methylation of Dietary Flavones Increases Their Metabolic Stability and Chemopreventive Effects

Abstract: Dietary flavones have promising chemoprotective properties, in particular with regard to cancer, but problems with low oral bioavailability and sometimes unacceptable toxicity have made their use as protective additives to normal diets questionable. However, methylation of free phenolic hydroxyl groups leads to derivatives not susceptible to glucuronic acid or sulfate conjugation, resulting in increased metabolic stability. Methylation also leads to greatly improved transport through biological membranes, such… Show more

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Cited by 124 publications
(101 citation statements)
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“…It has been shown that methylation of flavonoids makes them more lipophilic, thereby improving their transport over biological membranes and increasing their cellular uptake (Spencer et al, 2003(Spencer et al, , 2004. Moreover, blocking the free hydroxyl group by methylation prevents other conjugation reactions such as glucuronidation at this group and thus increases the metabolic stability of flavonoids (Walle, 2009). Methylation of the hydroxyl group also decreases the antioxidant capacity of flavonoids (Spencer et al, 2003).…”
Section: Discussionmentioning
confidence: 99%
“…It has been shown that methylation of flavonoids makes them more lipophilic, thereby improving their transport over biological membranes and increasing their cellular uptake (Spencer et al, 2003(Spencer et al, , 2004. Moreover, blocking the free hydroxyl group by methylation prevents other conjugation reactions such as glucuronidation at this group and thus increases the metabolic stability of flavonoids (Walle, 2009). Methylation of the hydroxyl group also decreases the antioxidant capacity of flavonoids (Spencer et al, 2003).…”
Section: Discussionmentioning
confidence: 99%
“…This result supports that the methylation of flavonoids enhanced the transporting ability, which leads to facilitated absorption and greatly enhanced bioavailability. The methylation of hydroxyl groups in the flavonoids significantly improved their intestinal absorption and metabolic stability (Wen & Walle, 2006;Walle 2009). Walle found that the methylation seems to be an effective method to enhance the metabolic resistance and transport of flavonoids (Walle 2007).…”
Section: Effects Of Methylation Of Hydroxyl Group In Dietary Flavonoimentioning
confidence: 99%
“…Courts and Williamson concluded that the C-glycoside aspalathin Molecular structure-affinity relationship of dietary flavonoids for bovine serum albumin Jian Shi and Hui Cao was methylated and glucuronidated in vivo (Courts & Williamson 2009). The potential therapeutic utility of the methylated flavones has also been advanced by finding that the methylation of flavonoids reduces the possibility of toxic side-effects (Walle 2009 Table 2 gave the effects of hydroxylation of flavonoids on the affinities for BSA in vitro. As seen from these data, the hydroxylation on the rings A, B and C of flavonoids dramatically influenced the binding affinities for BSA.…”
Section: Effects Of Methylation Of Hydroxyl Group In Dietary Flavonoimentioning
confidence: 99%
“…Anthocyanins are hydrophilic compounds, predictably unable to cross the cell plasma membrane by passive diffusion (9). Therefore, without a hydrophilic carrier, such as the NNS, which also have a hydrophobic, fatty acid component that ʻmeltsʼ into cell membranes to deposit the Bilberry into the cancer cells, one could understand the poor bioavailability of the anthocyanins (10,11). The results obtained show that the bilberry extract does have an increased anti-cancer effect when it is encapsulated compared to the free compound.…”
Section: Discussionmentioning
confidence: 62%