vanillic acid dipole

Mahdi ZM Alhaddad H +:� ɪ�?ζ�H��W��~�3$�QT��φ���D�����[���'�Y"GEQ���_hO��F�ю�]PH����В��N@ܮF�oI�N�B؀a����'��'� Kang Y-S 2018;61:18–30.

, Motilva M-J , Mattivi F Nevertheless, it has been proven that permeation through these two methods can be compromised in diseases within which inflammation occurs leading to an increase permeability of BBB to small molecules [105, 106]. Ohtsuki S Passive permeation depends on the physical-chemical properties of a molecule and could be predicted by in silico methods. Shukitt-Hale B << /Type /XRef /Filter /FlateDecode /Length 179 /W [ 1 3 1 ] /Index [ 77 53 ] , In turn, gallic acid, 3-O-methylgallicacid, and 4-hydroxyhydrocinnamic acid were not detected in the brain of these rats for any dose tested, despite being detected in other organs in the same animals. . In malt, vanillic acid … , Amini A .

Morrica P Spencer JPE Journal of Pharmacy. Effect of intracerebral hydroxytyrosol and its nitroderivatives on striatal dopamine metabolism: A study by in vivo microdialysis. Additionally, recent studies have been reported the ability of endothelial cells to metabolize the phenolic metabolites into novel compounds before allowing their penetration into the brain [25]. , The same model was used to confirm flavan-3-ols metabolites BBB permeability followed by in vivo validation [33].


Lv C , Rubió L ,

, , , , Seelig A , . Roowi S Crozier A Yin MC Ferruzzi MG Palma-Valdés R StarDrop: Molecules are classified by the authors as not probable or probable according to the log BB of -1 or higher than -1 respectively [39].

Nilmeier JP , 2004;36:592–604. , Biochem Pharmacol. Gasperotti M [b] iBET, Instituto de Biologia Experimental e Tecnológica, Avenida da República, Apartado 12, Oeiras, Portugal . Their distribution relies on their capability to cross several barriers they may encounter during their journey. Some attempts to address this was done by using monoclonal antibodies for the compounds [57, 58]. , Dose effect on the uptake and accumulation of hydroxytyrosol and its metabolites in target tissues in rats. , Rice-Evans C Figueira I ,et al.. Phenanthrene is a likely carcinogenic compound that poses a large toxicity risk to exposed living organisms. Furthermore, another commercially available in vitro model of BBB (RTU), consisting of bovine endothelial cells, was used to test the potential of ferulic acid, dihydroferulic acid, and dihydrocaffeic acidto cross the BBB [47]. . , Heal. , Accordingly, it is not clear if a chronic consumption vs. acute ingestion could impact the levels detected since there is no a direct comparison for the same time point of tissue collection after the last intake. Therefore, it is plausible to consider that the same transporters could be involved in the transport of the residual levels of flavonoid circulating and most importantly the transport of their more abundant LMW (poly)phenol metabolites. Keen CL Ho L Generally, it is described that malerodents tend to have higher levels of cytochrome P450, while phase II metabolism seems to be quite similar between genders. , Also, the brain presence of (poly)phenols seems to be independent of their route of administration, since different compounds were detected in the brain after different types of administration. Nakamura T Insights into the putative catechin and epicatechin transport across blood-brain barrier. 2009;16:233–43. Ekberg JAK , Kalt W . Moreover, sulfates of vanillin, vanillic acid and homovanilic were also detected in the brain of rats after the ingestion of phenolic extract from olive cake [80]. ,

Into rather unexplored terrain-transcellular transport across the blood-brain barrier. Milbury PE Rice-Evans C Feunang YD

, Yet, a limited number of studies have been conducted on LMW (poly)phenol metabolites molecules.

2017;9:180–6. 2011;2:39–44. For flavonoids, several mechanistic studies on their transport have been proposed, due to their molecular weight and other chemical properties like polar surface and number and position of the oxygen atoms among others discussed below. 2012;84:1088–95. 2016;60:760–72. Gender-related similarities and differences in the body distribution of grape seed flavanols in rats. , It is formed by multiple cell types and proteins that ensure tight regulation of the movement of ions, molecules, and cells between the blood and the brain. 2014;27:691–726. Agúndez JAG Blank R . Therefore, to reveal their potential effects, several studies focused on understanding their routes after being ingested, the metabolism they are submitted, the distribution to reach the target tissues, and ultimately, the mechanisms behind their action.

Sci Rep. 2016;6:29034-1–29034-10. , Kay CD Felgines C , The source of (poly)phenols is quite wide and variable and even the regular diet given to the rats can differ. , Impact of Flavonoids on Cellular and Molecular Mechanisms Underlying Age-Related Cognitive Decline and Neurodegeneration. , However, other mechanisms of transport are also considered, such as paracellular transport and vesicular transport (Fig. Serra A Food complexity and interactions among the different components can affect the release of the compounds from the matrix and the uptake leading to different pharmacokinetic profiles. 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. , Romero M-P [a] CEDOC, NOVA Medical School, Faculdade de Ciências Médicas, Universidade NOVA de Lisboa, Campo dos Mártires da Pátria, Lisboa, Portugal The penetration of catechol and pyrogallol into mouse brain and the effect on cerebral monoamine levels. , , Halquist MS , EC Number 204-466-8. Un article de Wikipédia, l'encyclopédie libre. In fact, for some of these metabolites we highlighted the pathways where they could be involved, using the KEGG pathways database [12]. Bellon K 2007;51:714–25.

Gр��}31�gL����b At3�5a0��E$M����/}_�E7D"{�0��Y����m�0`�p��~�`�g�:o�0�CHYR�N|��O�v�� �Sf ,et al.. Interestingly, in silico predictions about the permeability of the specific molecules with available information show corroborating data between in vitro and in silico predictions. , Ekins S On the other hand, vanillic acid presented the highest percentage of transport to the brain considering both the dose injected and the mean concentration found in control brains [51]. 2012;60:9377–83. Low-Molecular Weight Metabolites from Polyphenols as Effectors for Attenuating Neuroinflammation. Development of a computational approach to predict blood-Brain Barrier Permeability. Absorption and metabolism of flavonoids. , Lobo JK

, Dashed arrows represent possible methods of distribution to and from the brain observed for other xenobiotics and predicted for LMW (poly)phenols metabolites. 2019;11:2678. . . ,et al.. . Vanillic acid (4-hydroxy-3-methoxybenzoic acid) is a dihydroxybenzoic acid derivative used as a flavoring agent. Momma TY ,


, 8Homovanillic acid was also detected in the vehicle group and only for the highest dose (HT-100) homovanillic presented significant increases in the brain. , PubChem Substance ID 24895581. . J Pharm Pharmacol. Liu MC Additionally, male Balb/cA mice with a diet supplemented with protocatechuic acid have also shown increased levels of this metabolite in the brain, which were not detectable in brains from mice not supplemented [77]. 2010;58:3950–6. Spencer JPE Czank C J Alzheimers Dis. Another approach to evaluate brain permeability to (poly)phenol metabolites in vivo is its direct administration to the circulation bypassing the gastrointestinal tract (Table 5). Regardless of the mode of occurrence within the human body (by endogenous production or by dietary exposure to parent compounds) for some LMW (poly)phenol metabolites their presence in different human organs is already described in the human metabolome database (Table1) [13]. Based on this, we may expect that this type of transport could also be occurring for other phenolic acids. 2018;46:110–7. This work has received funding from the European Research Council (ERC) under the European Union’s Horizon 2020 Research and Innovation Programme under Grant Agreement No. Sugiyama Y J Agric Food Chem. , 2017;69:1846–57. Chen C ,et al.. Flavonoid metabolites transport across a human BBB model. The main reason for this is the fact that the major analytical approach for this evaluation in biological samples relies on chromatographic techniques. It is an oxidized form of vanillin. Peng HW , 1969;7:250–7. Ottaviani JI Kusuhara H Borges G Compr Rev Food Sci Food Saf. . Besson C All these parameters can then be conjugated into a single property designated commonly as log BB that represents the logarithmic ratio between the concentration of a compound in the brain and blood. 1BBB Kit™ (RBT-24) is anin vitro model of BBB made of primary cultures of rat (Wistar rat) brain capillary endothelial cells, brain pericytes, and astrocytes. del Bas JM Pimpão RC There is still huge gap in knowledge about the fate of LMW (poly)phenol metabolites in the brain, especially due to the diversity of brain resident cells (Fig. A Method to Predict Blood-Brain Barrier Permeability of Drug-Like Compounds Using Molecular Dynamics Simulations. Hosoya K Qi X-RR Manach C Lemon RN Anthocyanins in aged blueberry-fed rats are found centrally and may enhance memory.

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