, Bacterial species involved in the conversion of dietary flavonoids in the human gut. Qaiser MZ Nucleic Acids Res. , , Press S , https://doi.org/10.1097/01.WCB.0000050062.57184.75. Overall, data strongly suggest the effective uptake of dietary (poly)phenols and their metabolites through the BBB endothelium. , Terao J https://doi.org/10.1038/sj.bjp.0707305. Lucero MJ Exp Brain Res. , Biochem Biophys Reports. 2018;17:1054–112. Food Funct. Alonso-Navarro H Uchida K Il est constitué d'un cycle de benzène substitué par un groupe carboxyle, un groupe hydroxyle et un groupe méthoxyle en poitions 1, 3 et 4, ce qui fait de lui un vanilloïde. , , 2012;84:1088–95. , Pervin M , NeuroRX. Meireles M Temsamani J Kobayashi M ,et al.. , Kang Y All molecules with BBB(%) above 0.1 are considerately probable of crossing the BBB . , The effect of hydroxytyrosol and its nitroderivatives on catechol-O-methyl transferase activity in rat striatal tissue. Pons Z . 2017;139:82–93. Their structures having at least one hydroxyl group and one aromatic ring, together with functional groups have been linked to a huge variety of beneficial properties to human health, some of them related with brain health [1–3]. , Schaffer S Entrée « Vanillic acid » dans la base de données de produits chimiques. , J Med Food. /Size 130 /Prev 559401 LMW (poly)phenol metabolites considered were detected in humans circulating in plasma or excreted in urine after dietary flavonoids ingestion1. Polyphenols: food sources and bioavailability. Huang YT , Sci Rep. 2016;6:29034-1–29034-10. , Nakagawa K , López de las Hazas M-C Absorption and Distribution of Tea Catechin(-)-Epigallocatechin-3-Gallate, in the Rat. Capasso G Corona G One of the exceptions is salicylic acid where in silico predictions projected as not probable to reach the brain. Kanehisa M Lobo JK (Grant PD/BD/135492/2018). J Alzheimers Dis. Keen CL Br J Pharmacol. , Free Radic Biol Med. Teixeira J Wang Z-ZZ CONCLUSIONS Among the thirteen compounds selected for the determination of dipole moment to predict their stability. Palma-Valdés R LLC, New York 2011. Bieger J . Norton R Cheng FC x�c``�f``^���� �� � `6H����:c'C:Cݯ�U�OPy@y7�HF m�&`ٌ͒b��,���u��ED�Z��"��E�z�1. PubChem Substance ID 24895581. Surprisingly, there is scarce data concerning their disposition within human organs and pathways that could be involved (Table 1). Decrock E Dashed arrows represent possible methods of distribution to and from the brain observed for other xenobiotics and predicted for LMW (poly)phenols metabolites. , Sweet DH Distribution of morphine 6-glucuronide and morphine across the blood-brain barrier in awake, freely moving rats investigated by in vivo microdialysis sampling. , . Xenobiotic Metabolism and Berry Flavonoid Transport across the Blood-Brain Barrier. Tsuji A For instance, it was detected a prominent sex differences in the impact of tolcapone, COMT inhibitor, on dopamine metabolite levels. , Shiamoto K <> In any case, passive permeation may not be the only method of transport across the BBB, since it could also be mediated by carriers . https://doi.org/10.1016/j.bbrep.2016.12.012. De Bock M gThe original value (28.4μg/g of tissue) presented by the authors was converted to nmol/g of tissue considering the brain density of 1 g.cm–3 and the molecular weight of pyrogallol (126.1 g/mol). Moreover, gallic acid was present in the extract and 4-hydroxyhydrocinnamic acid could be generated by the metabolism of quercetin-3-O-galactoside, which was also present in GSPE . Rodriguez-Mateos A Ferulic acid was also found in the brain of rats that took Shunaoxin pills, a traditional Chinese medicine product enriched in ferulic acid. Almeida LL Schomburg D Iguchi K 2016;44:D457–62. Borràs X , Pe values were calculated for ferulic acid (1.31±0.20 Pe (×10–3 cm.min–1), dihydroferulic acid 1.20±0.24 Pe (×10–3 cm.min–1) and dihydrocaffeic acid 1.01±0.1 Pe (×10–3 cm.min–1). Iglesias-Carres L In fact, a huge potential in this field has been underestimated, and only for a few classes such as benzene diols and triols, benzoic acid, and cinnamic acid data was collected (Table 3). . Mohsen MA El Mol Nutr Food Res. , The authors concluded that hesperetin and naringenin present a high apparent permeability . Mazzoni O Motilva M-J 2013;57:1741–52. Smith BJ In fact, this issue is not fully understood, and the mechanisms by which phenolic metabolites permeate the BBB are still unknown. Deguchi T 2015;59:1395–9. These transporters may decrease the apparent permeability of the BBB to metabolites by transporting them back to the blood stream . Passive permeation depends on the physical-chemical properties of a molecule and could be predicted by in silico methods. Furthermore, SWISS ADME predicts ferulic acid has a molecule able to cross the BBB, together with p-coumaric and cinnamic acid but not sinapic acid. Texier O Astrocytes: Biology and pathology. Vanzo A Dis., vol. 79 0 obj , Muguerza B , LMW (poly)phenol metabolites disposition within human organism and pathways that are affect by those compounds. , It is also an intermediate … Select this link to jump to navigation, In navigation section. , , Tognolini M , 2005;8:111–20. Therefore, it is not surprising that these LMW (poly)phenol metabolites could be obtained in humans not only through the regular diet, but also by metabolizing other ingested compounds, like residues of industrial chemicals and pharmaceuticals . J Agric Food Chem. endobj , Authors: Carecho, Rafaela; c | Carregosa, Diogoa; b | dos Santos, Cláudia Nunesa; b; c; *, Affiliations: , Manach C , 2017;139:24–39. Genes Nutr. 6751 Tepper Drive Black arrows represent passage and distribution of the molecules into the brain. LMW (poly)phenol metabolites appearance in circulation in vivo peaks around 6 hours post-consumption and have longer elimination half-life [85, 86]. Regarding the nervous system, they will face one of the most regulated and controlled barriers in the human body, the blood-brain barrier (BBB), that must be crossed to directly influence the brain . https://doi.org/10.1039/c7bm00133a. | , Godinho-Pereira J Trujillo M , Simultaneous determination of gallic acid and gentisic acid in organic anion transporter expressing cells by liquid chromatography–tandem mass spectrometry. J Chromatogr A. Motilva M-J ,et al.. , 1995;275:435–41. Moreover, some CYP450 expression seems to be sex-specific, and their expression levels quite different between genders meaning the rate of metabolism and excretion can be highly dependent on the substrate . , Pandey AK Wong SE https://doi.org/10.1080/10715760400017293. ,et al. . , Terrasso AP Ishisaka A Abbott NJ Polyphenols Hum. You dim et al showed that permeation across the BBB is associated with lipophilicity, meaning polar metabolites like sulfate and glucuronide conjugates will have reduced passage through the BBB by comparison with less polar methylated conjugated [21, 22]. , https://doi.org/10.1016/j.freeradbiomed.2011.06.017. Mørland J https://doi.org/10.1021/jf301787f. Also, the astrocytes have an important role by projecting their end-feet to the walls of blood vessels, as well as the pericytes, which are involved in both endothelial cells support and paracrine signaling [19, 20]. Bagetta D 2014;149:190–6. https://doi.org/10.1002/mnfr.201500048. Spencer JPE In vitro cell-based studies, mostly taking advantage of brain endothelial cellular models, have been a very important tool to address the ability of metabolites permeation across the BBB endotheliumin a more realistic way. . Nakagawa A Maini Rekdal V , The content of single polyphenols were determined in 10 different varieties of barley and corresponding malts (Table 4 and Table 5, respectively).In barley samples the main phenolics identified were (+)-catechin, vanillic acid, caffeic acid, p-coumaric acid and ferulic acid. Pons Z 2017;57:399–416. https://doi.org/10.1039/C0FO00100G. Weksler B , https://doi.org/10.1093/ajcn/81.1.243s. 2016;99:128–38. https://doi.org/10.1093/nar/gkx1089. , Free Radic Biol Med. Some ready-to-use BBB model kits were already tested for LMW (poly)phenol metabolites BBB permeability. Romero I Improving the oral bioavailability of beneficial polyphenols through designed synergies. , , However, there are some contradictory results as is the case of anthocyanins that could not be detected in brains of rats after supplementation with raspberry juice in a dose equivalent to 700 mL to a 70 kg human  but were detected in other experimental designs that involved either higher doses or chronic administration [52, 72, 73]. 2017;5:1041–50. de la Torre R Tsai TH Li J Borges G J Agric Food Chem. Another aspect that may account for different results is the fact that these studies have used different rat strains (Sprague-Dawley vs. Wistar rats) whose endocrine system was described as different and this causes differences in food conversion and food intake .
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