Phytoestrogens as natural prodrugs in cancer prevention: dietary flavonoids

Arroo, R. R. J.; Androutsopoulos, Vasilis P.; Beresford, Kenneth J. M.; Ruparelia, Ketan C.; Surichan, Somchaiya; Wilsher, Nicola E.; Potter, Gerard A.

doi:10.1007/s11101-009-9128-6

Cited by 34 publications

(21 citation statements)

References 53 publications

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“…Other studies have also shown that intracellular metabolism (conjugation and oxidation) strongly affects the bioavailability (the amount that can be absorbed from the lumen) of flavonoids, thus regulates the biological activities of flavonoids in vivo (Williams et al 2004;Holst and Williamson 2008). Methoxylated flavones are considered to represent a superior anti-cancer flavonoid subclass due to their easy access to the target cells (lipophilicity) and large bioavailability (masking of reactive hydroxyl group) (Deng et al 2006;Arroo et al 2009;Walle 2007a, b). Based on these data, tricin appears to be an attractive candidate for pharmacological and medicinal studies although more and detailed human clinical trials as well as the studies of metabolism and bioavailability of tricin in vivo are needed.…”

Section: Biological Significance Of Tricinmentioning

confidence: 99%

Tricin—a potential multifunctional nutraceutical

2009

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This review throws light on the natural occurrence and distribution of tricin (5,7,4 0 -trihydroxy-3 0 ,5 0 -dimethoxyflavone) and its conjugated forms, as more common natural plant constituents than previously known. It examines the current literature dealing with its biosynthesis, regulation, biological significance, pharmacological effects, and potential role as a chemopreventive and anticancer agent. Because of its common occurrence in cereal grain plants and the wide spectrum of its health promoting effects, a metabolic engineering strategy is proposed to produce tricin in sufficient amounts for further experimentation, and increase its accumulation in wheat grain endosperm as a nutraceutical.

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Section: Biological Significance Of Tricinmentioning

confidence: 99%

Tricin—a potential multifunctional nutraceutical

2009

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“…Some healthrelated benefits are associated with this group of compounds, including strengthening of the immune system, protecting against cancer, and reducing capillary fragility (Lu et al, 2013). Because many flavonoid glycosides exhibit low oral bioavailability due to the microbial hydrolysis and conjugation that occurs in the intestine and the liver, this type of compound is generally considered a natural prodrug (Arroo et al, 2008(Arroo et al, , 2009; the health benefits are attributed to the metabolites capable of reaching the circulation (Dorjgochoo et al, 2012;Vissiennon et al, 2012;Romano et al, 2013). However, there have been few biologic/pharmacologic evaluations of the resultant conjugates (Terao, 1999;Koga and Meydani, 2001) because of limited access to the pure compounds.…”

Section: Introductionmentioning

confidence: 99%

The Presystemic Interplay between Gut Microbiota and Orally Administered Calycosin-7-O-β-d-Glucoside

Ruan

et al. 2015

Drug Metab Dispos

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Presystemic interactions with gut microbiota might play important roles in the holistic action of herbal medicines in their traditional oral applications. However, research interests usually focus on biologic activities of the in vivo available herb-derived components and their exposure in circulation. In this study, we illustrated the importance of studying the presystemic interplay with gut microbiota for understanding the holistic actions of medicinal herbs by using calycosin-7-O-b-D-glucoside (C7G), the most abundant flavonoid and chemical marker in Astragali Radix, as a model compound. When C7G was orally administrated to rats, calycosin-39-O-glucuronide (G2) was the major circulating component in the blood together with a minor calycosin but not C7G. Rat gut microbiota hydrolyzed C7G in vitro rapidly and produced its aglycone calycosin. Calycosin exhibited higher permeability than C7G and further underwent extensive glucuronidation to yield 3ʹ-glucuronide as the dominant metabolite. Bioactivity assays revealed that G2 exhibited similar or more potent proangiogenic effects than calycosin in human umbilical vein endothelial cells in vitro and in the vascular endothelial growth factor receptor tyrosine kinase inhibitor II-induced blood vessel loss model in zebrafish. More interestingly, the incubation of C7G with gut microbiota from both normal and colitic rats showed a probiotics-like effect through stimulating the growth of the beneficial bacteria Lactobacillus and Bifidobacterium. In conclusion, C7G interacts reciprocally with gut microbiota after oral dosing, which makes it not only an angiogenic prodrug but also a modulator of gut microbiota.

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“…Polyphenols are phytochemicals well studied for contributing to the prevention of cancer, cardiovascular and neurodegenerative diseases, and present in a variety of food sources, especially vegetables, fruits, tea ( Camellia sinensis ), cocoa and nuts. Most health benefits ascribed to polyphenols may be related to their prominent antioxidant and anti‐inflammatory effects, once oxidative damage and inflammation are usually present in chronic and degenerative diseases .…”

Section: Introductionmentioning

confidence: 99%