Biodisponibilidade de compostos fenólicos: um importante desafio para o desenvolvimento de fármacos?

ANAND, P.; KUNNUMAKKARA, A.B.; NEWMAN, R.A.; AGGARWAL, B.B. 2007 - Bioavailability of curcumin: problems and promises. Molecular Pharmaceutics, v. 4, p. 807-818. ARTS, I.C.; HOLLMAN, P.C. 2005 - Polyphenols and disease risk in epidemiologic studies. American Journal of Clinical Nutrition, v. 81, p. 317S-25S. BANSAL, S.; VYAS, S.; BHATTACHARYAC, S.; SHARMA, M. 2013 - Catechin prodrugs and analogs: a new array of chemical entities with improved pharmacological and pharmacokinetic properties. Natural Product Reports, v. 30, p. 1438-1454. BIASUTTO, L.; ZORATTI, M. 2014 - Prodrugs of quercetin and resveratrol: A strategy under development. Current Drug Metabolism, v. 15, p. 77-95. BOLLI, A.; MARINO, M.; RIMBACH, G.; FANALI, G.; FASANO, M.; ASCENZI, P. 2010 - Flavonoid binding to human serum albumin. Biochemical and Biophysical Research Communications, v. 398, p. 444-449. BONIFÁCIO, B.V.; SILVA, P.B.D.; RAMOS, M.A.D.S.; NEGRI, K.M.S.; BAUAB, T.M.; CHORILLI, M. 2014 - Nanotechnology-based drug delivery systems and herbal medicines: a review. International Journal of Nanomedicine, v. 9, p. 1-15. BOUDET, A.M. 2007 - Evolution and current status of research in phenolic compounds. Phytochemistry, v. 68, p. 2722-2735. BRAVO, L. 1998 - Polyphenols: Chemistry, dietary sources, metabolism, and nutritional significance. Nutrition Reviews, v. 56, p. 317-333. CHEN, Z.; ZHENG, S.; LI, L.; JIANG, H. 2014 - Metabolism of flavonoids in human: A comprehensive review. Current Drug Metabolism, v. 15, p. 48-61. CHEYNIER, V.; COMTE, G.; DAVIES, K.M.; LATTANZIO, V.; MARTENS, S. 2013 - Plant phenolics: Recent advances on their biosynthesis, genetics, and ecophysiology. Plant Physiology and Biochemistry, v. 72, p. 1-20. CLAVEL, T.; BORRMANN, D.; BRAUNE, A.; DORÉ, J.; BLAUT, M. 2006 - Occurrence and activity of human intestinal bacteria involved in the conversion of dietary lignans. Anaerobe, v. 12, p. 140-147. CLINICALTRIALS.GOV. Available at: https://clinicaltrials.gov/ct2/home. Access on March 15, 2015. CORREA-BETANZO, J.; ALLEN-VERCOE, E.; MCDONALD, J.; SCHROETER, K.; CORREDIG, M.; PALIYATH, G. 2014 - Stability and biological activity of wild blueberry (Vaccinium angustifolium) polyphenols during simulated in vitro gastrointestinal digestion. Food Chemistry, v. 165, p. 522-531. CROZIER, A.; JAGANATH, I.B.; CLIFFORD, M.N. 2009 - Dietary phenolics: chemistry, bioavailability and effects on health. Natural Product Reports, v. 26, p. 965-1096. CROZIER, A.; RIO, D.D.; CLIFFORD, M.N. 2010 - Bioavailability of dietary flavonoids and phenolic compounds. Molecular Aspects of Medicine, v. 31, p. 446-467. CURCIO, M.; CIRILLO, G.; PARISI, O.I.; IEMMA, F.; PICCI, N.; PUOCI, F. 2012 - Quercetin-imprinted nanospheres as novel drug delivery devices. Journal of Functional Biomaterials, v. 3, p. 269-282. D’ARCHIVIO, M.; FILESI, C.; VARÃŒ, R.; SCAZZOCCHIO, B.; MASELLA, R. 2010 - Bioavailability of the polyphenols: status and controversies. International Journal of Molecular Sciences, v. 11, p. 1321-1342. DHILLON, N.; AGGARWAL, B.B.; NEWMAN, R.A.; A.WOLFF, R.; KUNNUMAKKARA, A.B.; ABBRUZZESE, J.L.; NG, C.S.; BADMAEV, V.; KURZROCK, R. 2008 - Phase II trial of curcumin in patients with advanced pancreatic cancer. Clinical Cancer Research, v. 14, p. 4491-4499. FÉRRIZ, J.M.; VINOVÁ, J. 2010 - Prodrug design of phenolic drugs. Current Pharmaceutical Design, v. 16, p. 2033-2052. GAO, S.; BASU, S.; YANG, Z.; DEB, A.; HU, M. 2012 - Bioavailability challenges associated with development of saponins as therapeutic and chemopreventive agents. Current Drug Targets, v. 13, p. 1885-1899. GONZÁLEZ, S.; FERNÁNDEZ, M.; CUERVO, A.; LASHERAS, C. 2014 - Dietary intake of polyphenols and major food sources in an institutionalized elderly population. Journal of Human Nutrition and Dietetics, v. 27, p. 176-183. GOTA, V.S.; MARU, G.B.; SONI, T.G.; GANDHI, T.R.; KOCHAR, N.; AGARWAL, M.G. 2010 - Safety and pharmacokinetics of a solid lipid curcumin particle formulation in osteosarcoma patients and healthy volunteers. Journal of Agricultural and Food Chemistry, v. 58, p. 2095-2099. HAJIRAHIMKHAN, A.; DIETZ, B.M.; BOLTON, J.L. 2013 - Botanical modulation of menopausal symptoms: mechanisms of action? Planta Medica, v. 79, p. 538-553. HELENO, S.A.; MARTINS, A.; QUEIROZ, M.J.R.P.; FERREIRA, I.C.F.R. 2015 - Bioactivity of phenolic acids: Metabolites versus parent compounds: A review. Food Chemistry, v. 173, p. 501-513. HOLLMAN, P.; KATAN, M. 1997 - Absorption, metabolism and health effects of dietary flavonoids in man. Biomedicine & Pharmacotherapy, v. 51, p. 305-310. KAMONPATANA, K.; GIUSTI, M.M.; CHITCHUMROONCHOKCHAI, C.; CRUZ, M.M.; RIEDL, K.M.; KUMAR, P.; FAILLA, M.L. 2012 - Susceptibility of anthocyanins to ex vivo degradation in human saliva. Food Chemistry, v. 135, p. 738-747. KHUSHNUD, T.; MOUSA, S.A. 2013 - Potential role of naturally derived polyphenols and their nanotechnology delivery in cancer. Molecular Biotechnology, v. 55, p. 78-86. KIDD, P.M. 2009 - Bioavailability and activity of phytosome complexes from botanical polyphenols: The silymarin, curcumin, green tea, and grape seed extracts. Alternative Medicine Review, v. 14, p. 226-246. KOBAYASHI, S.; SHINOHARA, M.; NAGAI, T.; KONISHI, Y. 2013 - Transport mechanisms of soy isoflavones and their microbial metabolites dihydrogenistein and dihydrodaidzein across monolayers and membranes. Pharmaceutic Analytica Acta, v. 4, p. 2210-2217. LAFAY, S.; GIL-IZQUIERDO, A.; MANACH, C.; MORAND, C.; BESSON, C; SCALBERT, A. 2006 - Chlorogenic acid is absorbed in its intact form in the stomach of rats. The Journal of Nutrition, v. 136, p. 1192-1197. LAMBERT, J.D.; RICE, J.E.; HONG, J.; HOUA, Z.; YANGA, C.S. 2005 - Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives. Bioorganic & Medicinal Chemistry Letters, v. 15, p. 873-876. LAMBERT, J.D.; SANG, S.; HONG, J.; KWON, S.-J.; LEE, M.-J.; HO, C.-T.; YANG, C.S. 2006 - Peracetylation as a means of enhancing in vitro bioactivity and bioavailability of epigallocatechin-3-gallate. Drug Metabolism and Disposition, v. 34, p. 2111-2116. LAMBERT, J.D.; SANG, S.; YANG, C.S. 2007 - Biotransformation of green tea polyphenols and the biological activities of those metabolites. Molecular Pharmaceutics, v. 4, p. 819-825. LANDETE, J.M. 2012 - Plant and mammalian lignans: A review of source, intake, metabolism, intestinal bacteria and health. Food Research International, v. 46, p. 410-424. LAO, C.D.; RUFFN, M.T.; NORMOLLE, D.; HEATH, D.D.; MURRAY, S.I.; BAILEY, J.M.; BOGGS, M.E.; CROWELL, J.; ROCK, C.L.; BRENNER, D.E. 2006 - Dose escalation of a curcuminoid formulation. BMC Complementary and Alternative Medicine, v. 6. LEWANDOWSKA, U.; SZEWCZYK, K.; HRABEC, E.b.; JANECKA, A.; GORLACH, S. 2013 - Overview of metabolism and bioavailability enhancement of polyphenols. Journal of Agricultural and Food Chemistry, v. 61, p. 12183-12199. LI, Z.; JIANG, H.; XU, C.; GU, L. 2015 - A review: Using nanoparticles to enhance absorption and bioavailability of phenolic phytochemicals. Food Hydrocolloids, v. 43, p. 153-164. LI, J.; SHIN, G.H.; CHEN, X.; A, H.J.P. 2015 - Modified curcumin with hyaluronic acid: Combination of pro-drug and nano-micelle strategy to address the curcumin challenge. Food Research International, v. 69, p. 202-208. LU, D.-L.; DING, D.-J.; YAN, W.-J.; LI, R.-R.; DAI, F.; WANG, Q.; YU, S.-S.; LI, Y.; JIN, X.-L.; ZHOU, B. 2013 - Influence of glucuronidation and reduction modifications of resveratrol on its biological activities. ChemBioChem, v. 14, p. 1094-1104. MANACH, C.; SCALBERT, A.; MORAND, C.; RÉMÉSY, C.; JIMÉNEZ, L. 2004- Polyphenols: food source and bioavailability. The American Journal of Clinical Nutrition, v. 79, p. 727-747. MARIER, J.; VACHON, P.; GRITSAS, A.; ZHANG, J.; MOREAU, J.; DUCHARME, M. 2002 - Metabolism and disposition of resveratrol in rats: extent of absorption, glucuronidation, and enterohepatic recirculation evidenced by a linked-rat model. The Journal of Pharmacology and Experimental Therapeutics, v. 302, p. 369-373. MARQUES, L.C.; SOUZA, C.M. 2012 - Pesquisa e desenvolvimento de fitoterápicos: Relatos de experiência em indústria farmacêutica nacional. Revista Fitos, v. 7, p. 50-66. MIKSITS, M.; WLCEK, K.; SVOBODA, M.; KUNERT, O.; HASLINGER, E.; THALHAMMER, T.; SZEKERES, T.; JÄGER, W. 2009 - Antitumor activity of resveratrol and its sulfated metabolites against human breast cancer cells. Planta Medica, v. 75, p. 1227-1230. PELUSO, I.; PALMERY, M. 2015 - Flavonoids at the pharma-nutrition interface: Is a therapeutic index in demand? Biomedicine & Pharmacotherapy, v. 71, p. 102-107. PEREZ-VIZCAINO, F.; DUARTE, J.; SANTOS-BUELGA, C. 2012 - The flavonoid paradox: conjugation and deconjugation as key steps for the biological activity of flavonoids. Journal of the Science of Food and Agriculture, v. 92, p. 1822-1825. QUIDEAU, S.; DEFFIEUX, D.; DOUAT-CASASSUS, C.; POUYSÉGU, L. 2011 - Plant polyphenols: Chemical properties, biological activities, and synthesis. Angewandte Chemie, v. 50, p. 586-621 REIN, M.J.; RENOUF, M.; CRUZ-HERNANDEZ, C.; ACTIS-GORETTA, L.; THAKKAR, S.K.; PINTO, M.D.S. 2012 - Bioavailability of bioactive food compounds: a challenging journey to bioefficacy. British Journal of Clinical Pharmacology, v. 75, p. 588-602. RUBIÓ, L.; MACIÀ, A.; CASTELL-AUVÍ, A.; PINENT, M.; BLAY, M.T.; ARDÉVOL, A.; ROMERO, M.-P.; MOTILVA, M.-J. 2014 - Effect of the co-occurring olive oil and thyme extracts on the phenolic bioaccessibility and bioavailability assessed by in vitro digestion and cell models. Food Chemistry, v. 149, p. 277-284. SANDUR, S.K.; PANDEY, M.K.; SUNG, B.; AHN, K.S.; MURAKAMI, A.; SETHI, G.; LIMTRAKUL, P.; BADMAEV, V.; AGGARWAL, B.B. 2007 - Curcumin, demethoxycurcumin, bisdemethoxycurcumin, tetrahydrocurcumin and turmerones differentially regulate anti-inflammatory and anti-proliferative responses through a ROS-independent mechanism. Carcinogenesis, v. 28, p. 1765-1773. SANTOS, A.C.; VEIGA, F.; RIBEIRO, A.J. 2011 - New delivery systems to improve the bioavailability of resveratrol. Expert Opinion on Drug Delivery, v. 8, p. 973-990. SANTOS, A.C.; COSTA, G.; VEIGA, F.; FIGUEIREDO, I.V.; BATISTA, M.T.; RIBEIRO, A.J. 2014 - Advance in methods studying the pharmacokinetics of polyphenols. Current Drug Metabolism, v. 15, p. 96-115. SELMA, M.A.V.; ESPÍN, J.C.; TOMÁS-BARBERÁN, F.A. 2009 - Interaction between phenolics and gut microbiota: role in human health. Journal of Agricultural and Food Chemistry, v. 57, p. 6485-6501. SEMALTY, A.; SEMALTY, M.; SINGH, D.; RAWAT, M.S.M. 2012 - Phyto-phospholipid complex of catechin in value added herbal drug delivery. Journal of Inclusion Phenomena and Macrocyclic Chemistry, v. 73, p. 377-386. SETCHELL, K.D.R.; BROWN, N.M.; ZIMMER-NECHEMIAS, L.; WOLFE, B.; JHA, P.; HEUBIB, J.E. 2014 - Metabolism of secoisolariciresinol-diglycoside the dietary precursor to the intestinally derived lignan enterolactone in humans. Food & Function, v. 5, p. 491-501. SINGH, G.; PAI, R.S. 2014 - Recent advances of resveratrol in nanostructured based delivery systems and in the management of HIV/AIDS. Journal of Controlled Release, v. 194, p. 178-188. SOPPIMATH, K.S.; AMINABHAVI, T.M.; KULKARNI, A.R.; RUDZINSKI, W.E. 2001 - Biodegradable polymeric nanoparticles as drug delivery devices. Journal of Controlled Release, v. 70, p. 1-20. SOUSA, I.P.; BERNKOP-SCHNÃœRCH, A. 2014 - Pre-systemic metabolism of orally administered drugs and strategies to overcome it. Journal of Controlled Release, v. 192, p. 301-309. SURESH, D.; SRINIVASAN, K. 2010 - Tissue distribution & elimination of capsaicin, piperine & curcumin following oral intake in rats. Indian Journal of Medical Research, v. 131, p. 682-691. TIAN, X.-J.; YANG, X.-W.; YANG, X.; WANG, K. 2009 - Studies of intestinal permeability of 36 flavonoids using Caco-2 cell monolayer model. International Journal of Pharmaceutics, v. 367, p. 58-64. TOMÁS-BARBERÁN, F.A.; ANDRÉS-LACUEVA, C. 2012 - Polyphenols and health: Current state and progress. Journal of Agricultural and Food Chemistry, v. 60, p. 8773-8775. TOMÉ-CARNEIRO, J.; LARROSA, M.; GONZÁLEZ-SARRÍAS, A.; TOMÁS-BARBERÁN, F.A.; GARCÍA-CONESA, T.M.; ESPÍN, J.C. 2013 - Resveratrol and clinical trials: the crossroad from in vitro studies to human evidence. Current Pharmaceutical Design, v. 19, p. 6064-6093. TZOUNIS, X.; VULEVIC, J.; KUHNLE, G.G.C.; GEORGE, T.; LEONCZAK, J.; GIBSON, G.R.; KWIK-URIBE, C.; SPENCER, J.P.E. 2008 - Flavanol monomer-induced changes to the human faecal microflora. British Journal of Nutrition, v. 99, p. 782-792. VAN DER HOOFT, J.J.J.; VOS, R.C.H.d.; MIHALEVA, V.; BINO, R.J.; RIDDER, L.; ROO, N.D.; JACOBS, D.M.; DUYNHOVEN, J.P.M.V.; VERVOORT, J. 2012 - Structural elucidation and quantification of phenolic conjugates present in human urine after tea intake. Analytical Chemistry, v. 84, p. 7263-7271. VAREED, S.K.; KAKARALA, M.; RUFFIN, M.T.; CROWELL, J.A.; P.; NORMOLLE, P.D; DJURIC, Z.; BRENNER, D.E. 2008 - Pharmacokinetics of curcumin conjugate metabolites in healthy human subjects. Cancer Epidemiology, Biomarkers & Prevention, v. 17, p. 1411-1417. VELDERRAIN-RODRÍGUEZ, G.R.; PALAFOX-CARLOS, H.; WALL-MEDRANO, A.; AYALA-ZAVALA, J.F.; CHEN, C.-Y.O.; ROBLES-S´ANCHEZ, M.; ASTIAZARAN-GARCÍA, H.; ALVAREZ-PARRILLA, E.; GONZ´ALEZ-AGUILAR, G.A. 2014 - Phenolic compounds: their journey after intake. Food & Function, v. 5, p. 189-197. VISSIENNON, C.; NIEBER, K.; KELBER, O.; BUTTERWECK, V. 2012 - Route of administration determines the anxiolytic activity of the flavonols kaempferol, quercetin and myricetin — are they prodrugs? Journal of Nutritional Biochemistry, v. 23, p. 733-740. VITRAC, X.; DESMOULIÈRE, A.; BROUILLAUD, B.; KRISA, S.; DEFFIEUX, G.R.; BARTHE, N.; ROSENBAUM, J.; MÉRILLON, J.-M. 2003 - Distribution of [14C]-trans-resveratrol, a cancer chemopreventive polyphenol, in mouse tissues after oral administration. Life Sciences, v. 72, p. 2219-2233. WALLE, T.; HSIEH, F.; DELEGGE, M.H.; Jr., J.E.O.; WALLE, U.K. 2004 - High absorption but very low bioavailability of oral resveratrol in humans. Drug Metabolism and Disposition, v. 32, p. 1377-1382. WEINERT, C.H.; WIESE, S.; RAWEL, H.M.; ESATBEYOGLU, T.; WINTERHALTER, P.; HOMANN, T.; KULLING, S.E. 2012 - Methylation of catechins and procyanidins by rat and human catechol-O-methyltransferase: metabolite profiling and molecular modeling studies. Drug Metabolism and Disposition, v. 40, p. 353-359. WILLIAMSON, G.; CLIFFORD, M.N. 2010 - Colonic metabolites of berry polyphenols: the missing link to biological activity? British Journal of Nutrition, v. 104, p. S48-S66. WU, B.; BASU, S.; MENG, S.; WANG, X.; ZHANG, S.; HU, M. 2011a - Regioselective sulfation and glucuronidation of phenolics: Insights into the structural basis of conjugation. Current Drug Metabolism, v. 12, p. 900-916. WU, B.; KULKARNI, K.; BASU, S.; ZHANG, S.; HU, M. 2011b - First-pass metabolism via UDP-glucuronosyltransferase: a barrier to oral bioavailability of phenolics. Journal of Pharmaceutical Sciences, v. 100, p. 3655-3681. YU, Y.; DENG, Y.; LU, B.-m.; LIU, Y.-x.; LI, J.; BAO, J.-k. 2014 - Green tea catechins: a fresh flavor to anticancer therapy. Apoptosis, v. 19, p. 1-18. ZHANG, X.; SONG, J.; SHI, X.; MIAO, S.; LI, Y.; WEN, A. 2013 - Absorption and metabolism characteristics of rutin in Caco-2 cells. The Scientific World Journal, v. 2013, p.1-8. ZHAO, Z.; MOGHADASIAN, M.H. 2010 - Bioavailability of hydroxycinnamates: a brief review of in vivo and in vitro studies. Phytochemistry Reviews, v. 9, p. 133-145. ZHOU, J.; ZHOU, M.; YANG, F.F.; LIU, G.Y.; PAN, R.L.; CHANG, Q.; LIU, M.X.; LIAO, Y.H. 2015- Involvement of the inhibition of intestinal glucuronidation in enhancing of the oral bioavailability of resveratrol by labrasol conaining nanoemulsion. Molecular Pharmaceutics, v. 12, p.1084-95.