Red wine and components flavonoids inhibit UGT2B17 in vitro

Background The metabolism and excretion of the anabolic steroid testosterone occurs by glucuronidation to the conjugate testosterone glucuronide which is then excreted in urine. Alterations in UGT glucuronidation enzyme activity could alter the rate of testosterone excretion and thus its bioavailability. The aim of this study is to investigate if red wine, a common dietary substance, has an inhibitory effect on UGT2B17. Methods Testosterone glucuronidation was assayed using human UGT2B17 supersomes with quantification of unglucuronidated testosterone over time using HPLC with DAD detection. The selected red wine was analysed using HPLC and the inhibitory effects of the wine and phenolic components were tested independently in a screening assay. Further analyses were conducted for the strongest inhibitors at physiologically relevant concentrations. Control experiments were conducted to determine the effects of the ethanol on UGT2B17. Results Over the concentration range of 2 to 8% the red wine sample inhibited the glucuronidation of testosterone by up to 70% over 2 hours. The ethanol content had no significant effect. Three red wine phenolics, identified by HLPC analyses, also inhibited the enzyme by varying amounts in the order of quercetin (72%), caffeic acid (22%) and gallic acid (9%); using a ratio of phenolic:testosterone of 1:2.5. In contrast p-coumaric acid and chlorogenic acid had no effect on the UGT2B17. The most active phenolic was selected for a detailed study at physiologically relevant concentrations, and quercetin maintained inhibitory activity of 20% at 2 M despite a ten-fold excess of testosterone. Conclusion This study reports that in an in vitro supersome-based assay, the key steroid-metabolising enzyme UGT2B17 is inhibited by a number of phenolic dietary substances and therefore may reduce the rate of testosterone glucuronidation in vivo. These results highlight the potential interactions of a number of common dietary compounds on testosterone metabolism. Considering the variety of foodstuffs that contain flavonoids, it is feasible that diet can elevate levels of circulating testosterone through reduction in urinary excretion. These results warrant further investigation and extension to a human trial to delineate the healt

Phenolic and furanic compounds of Portuguese chestnut and French, American and Portuguese oak wood chips

Botanical species used on aging process must be wisely and judiciously chosen, and for this selection, a basic knowledge of the chemical composition of woods is warranted. Aiming to contribute to extend the knowledge of the chemical composition of several wood species useful for enological purposes, we have focused our studies on Portuguese chestnut and French, American and Portuguese oak chips. The profile of low molecular weight phenolic composition of these chips was achieved, using an optimized extraction method based on pressurized liquid extraction, followed by the quantification of phenolic acids, phenolic aldehydes and furanic derivatives by high-performance liquid chromatography (HPLC-DAD). The identification of those compounds was also confirmed by LC-DAD/ESI-MS. This study allowed the determination of the low molecular phenolic composition of Portuguese chestnut and French, American and Portuguese oak wood. According to our results, the influence of the botanical species seems to be more relevant than the geographic origin of the wood species

Phenolic composition of monovarietal red wines regarding volatile phenols and its precursors

The aim of this study was to characterise and compare wines from different grape varieties focusing on the volatile phenols and on the respective precursor compounds, both on the free form (p-coumaric, ferulic and caffeic acids) and as tartaric esters of hydroxycinnamic acids (caftaric, coutaric and fertaric acids). Fifty-eight commercial monovarietal red wines from eight selected grape varieties were used: Cabernet Sauvignon, Syrah, Aragonez, Castelão, Touriga Franca, Touriga Nacional, Trincadeira and Vinhão (Sousão). It was found that volatile phenol precursors exist mostly as esters of tartaric acid, with caftaric acid as the most abundant cinnamate (17–111 mg/L), followed by coutaric and fertaric acids. The predominant hydroxycinnamic acid was p-coumaric acid, the highest concentrations being found in Syrah and Touriga Franca (6–7 mg/L) and the lowest in Touriga Nacional and Trincadeira (2–3 mg/L). Touriga Nacional exhibits the highest difference between bound and free forms. Malvidin-3-O-(6-p-coumaroyl)-glucoside, a potential source of p-coumaric acid, was found in most of the wines with average values varying between 1 and 5 mg/L. Twenty-two percent of the wines analysed presented levels of volatile phenols above the perception threshold. Ethylphenols were the highest in Vinhão and Trincadeira, showing an average value well above the perception threshold. The concentrations found in Cabernet Sauvignon and Syrah wines were around ten times lower than those reported in previous works. The results show relevant differences among grape varieties but the availability of the precursors in meaningful amounts may not be the only factor explaining the formation of volatile phenols in wines.info:eu-repo/semantics/publishedVersio

Treatment by fining agents of red wine affected by phenolic off-odour

Although phenolic off-odour is very detrimental for red wine quality, there is a lack of easy-to-use methods able to decrease the levels of the responsible compounds 4-ethylphenol (4-EP) and 4-ethylguaiacol (4-EG) and to improve the sensory quality of the contaminated wines. To this aim, an alternative use of fining agents (activated charcoal, PVPP and zeolite) was evaluated. Two levels of ethylphenol contamination were considered: a naturally low contaminated red wine and the same wine spiked with 4-EP and 4-EG. The impact of the treatments on desirable aroma volatiles, polyphenols and colour was also evaluated. The effectiveness in diminishing the intensity of the phenolic off-odour was assessed by descriptive sensory analysis. The activated charcoal and PVPP significantly decreased the concentrations of 4-ethylguaiacol and 4-ethylphenol in the naturally contaminated wine, while none of the tested fining agent was effective in the spiked one. Polyphenols and colour were slightly affected, to the same extent for the two treatments. Charcoal and PVPP additions negatively impacted the concentration of the aroma volatiles, especially esters, with the activated charcoal achieving a higher decrease. The sensory outcome of both treatments was the decrease in the intensity of phenolic off-odour, with charcoal achieving a higher decrease. Interestingly, in spite of the decrease in esters, also a significant increase in the intensity of “red fruit” odour occurred