5-(3′,4′-Dihydroxyphenyl)-γ-valerolactone and its sulphate conjugates, representative circulating metabolites of flavan-3-ols, exhibit anti-adhesive activity against uropathogenic Escherichia coli in bladder epithelial cells

Rethinking the Mechanism of the Health Benefits of Proanthocyanidins: Absorption, Metabolism, and Interaction with Gut Microbiota

“…The majority of proanthocyanidins are passed into the large intestine, fermented by microbiota and degraded into different types of phenylvalerolactones and phenolic acids (Barros, García‐Villalba, Tomás‐Barberán, & Genovese, ). These metabolites can be reabsorbed and detected in blood (Mena et al., ). Some studies have also investigated and demonstrated the bioactivity and beneficial health effects of these metabolites (Monagas et al., ).…”

“…Studies have shown that metabolites of proanthocyanidins also exhibited strong bioactivity. 5‐(3′,4′‐dihydroxyphenyl)‐γ‐valerolactone, a metabolite of proanthocyanidins, inhibit the adhesive activity of uropathogenic Escherichia coli in bladder epithelial cells and thus attenuated THP‐1 monocyte‐endothelial adhesion (Lee et al., ; Mena et al., ). Also, dihydroxyphenyl‐γ‐valerolactone derivatives which are metabolites of cranberry proanthocyanidins have been proved to prevent invasion of UPEC ATCC R 53503 TM which may cause UTIs, while 5‐(3’‐hydroxyphenyl)‐γ‐valerolactone‐4‐ O ‐sulphate also shows neuroprotective effects at 50 µM (Mena et al., ).…”

A randomized, double-blind, placebo-controlled pilot study to assess bacterial anti-adhesive activity in human urine following consumption of a cranberry supplement

“…One of the cranberry PAC degradation products, valerolactone and its derivatives, showed anti-adhesion properties at a concentration of 100 μM, indicating their potential biologically relevant activity in urine. 19 Despite encouraging observation from cell-based studies, few studies have investigated the ex vivo urinary anti-adhesion effect against type 1 E. coli, combining both a human intervention component and an in vitro component to study exposure to the cranberry product occurring at expected intake levels in humans and the presence of anti-adhesive cranberry components in the urine. Di Martino et al 24 found that urine from cranberry juice consumers inhibited the adhesion of E. coli with type 1 fimbriae.…”

“…18 Moreover, the gut microbial degradation products of cranberry PACs, valerolactone and its derivatives exhibited anti-adhesion properties against P-type UPEC at a concentration of 100 μM, indicating their potential biologically relevant activity in urine. 19 The anti-adhesion activities of cranberry-derived metabolites suggest that their presence in the urine could be responsible for the further reduction of bacterial colonization and pathogenesis of UTIs.…”

Concise Synthesis of Catechin Metabolites 5-(3′,4′-Dihydroxyphenyl)-γ-valerolactones (DHPV) in Optically Pure Form and Their Stereochemical Effects on Skin Wrinkle-Reducing Activities

“…Since the first report on the metabolic fate of (+)-catechin in rabbits by Watanabe et al [9], there have been intensive pharmacokinetic studies on DHPV [10][11][12] after the intake of a single flavan-3-ol or polyphenol-rich foods in various living organisms for the past half century. However, investigation on its biological effects were relatively rare, except for a few reports [13][14][15][16]. Despite the lack of studies on DHPVs' role in the biological system, several papers recently reported that DHPV exhibits a protective effect against UV-induced skin inflammation [17] or photoaging [18].…”