Tea catechins’ affinity for human cannabinoid receptors

Phytomedicine - Tập 17 - Trang 19-22 - 2010
G. Korte1, A. Dreiseitel1, P. Schreier2, A. Oehme2, S. Locher2, S. Geiger3, J. Heilmann3, P.G. Sand1
1Department of Psychiatry, University of Regensburg, Franz-Josef-Strauss-Allee 11, H4 R97 93053 Regensburg, Germany
2Chair of Food Chemistry, University of Wuerzburg, Am Hubland, 97074 Wuerzburg, Germany
3Chair of Pharmaceutical Biology, Institute of Pharmacy, University of Regensburg, Universitaetsstrasse 31, 93053 Regensburg, Germany

Tài liệu tham khảo

Abbas, 2009, Epigallocatechin gallate from green tea (Camellia sinensis) increases lifespan and stress resistance in Caenorhabditis elegans, Planta Med., 75, 216, 10.1055/s-0028-1088378 Adachi, 2006, Epigallocatechin gallate attenuates acute stress responses through GABAergic system in the brain, Eur. J. Pharmacol., 531, 171, 10.1016/j.ejphar.2005.12.024 Adachi, 2007, Galloyl group is not necessary for a sedative effect of catechin through GABAergic system, Lett. Drug Des. Discovery, 4, 163, 10.2174/157018007780077444 Arts, 2000, Catechin contents of foods commonly consumed in The Netherlands. 1. Fruits, vegetables, staple foods, and processed foods, J. Agric. Food Chem., 48, 1746, 10.1021/jf000025h Arts, 2001, Catechin intake and associated dietary and lifestyle factors in a representative sample of Dutch men and women, Eur. J. Clin. Nutr., 55, 76, 10.1038/sj.ejcn.1601115 Auvichayapat, 2008, Effectiveness of green tea on weight reduction in obese Thais: a randomized, controlled trial, Physiol. Behav., 93, 486, 10.1016/j.physbeh.2007.10.009 Bari, 2005, Lipid rafts control signaling of type-1 cannabinoid receptors in neuronal cells. Implications for anandamide-induced apoptosis, J. Biol. Chem., A280, 12,212, 10.1074/jbc.M411642200 Bastianetto, 2009, Comparative neuroprotective properties of stilbene and catechin analogs: action via a plasma membrane receptor site?, CNS Neurosci. Ther., 15, 76, 10.1111/j.1755-5949.2008.00074.x Bose, 2008, The major green tea polyphenol, (−)-epigallocatechin-3-gallate, inhibits obesity, metabolic syndrome, and fatty liver disease in high-fat-fed mice, J. Nutr., 138, 1677, 10.1093/jn/138.9.1677 Capasso, 1998, Flavonoids reduce morphine withdrawal in-vitro, J. Pharm. Pharmacol., 50, 561, 10.1111/j.2042-7158.1998.tb06199.x Cheng, 1973, Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (IC50) of an enzymatic reaction, Biochem. Pharmacol., 22, 3099, 10.1016/0006-2952(73)90196-2 Chou, 2007, Epigallocatechin gallate, the most active polyphenolic catechin in green tea, presynaptically facilitates Ca2+-dependent glutamate release via activation of protein kinase C in rat cerebral cortex, Synapse, 61, 889, 10.1002/syn.20444 Cooper, 2005, Medicinal benefits of green tea: part I. Review of noncancer health benefits, J. Altern. Complement. Med., 11, 521, 10.1089/acm.2005.11.521 DalBó, 2005, Antinociceptive effect of proanthocyanidins from Croton celtidifolius bark, J. Pharm. Pharmacol., 57, 765, 10.1211/0022357056091 Dias, 2007, Antinociceptive activity of Maytenus rigida stem bark, Fitoterapia, 78, 460, 10.1016/j.fitote.2007.02.017 Diepvens, 2005, Effect of green tea on resting energy expenditure and substrate oxidation during weight loss in overweight females, Br. J. Nutr., 94, 1026, 10.1079/BJN20051580 Furuno, 2002, The contribution of the pyrogallol moiety to the superoxide radical scavenging activity of flavonoids, Biol. Pharm. Bull., 25, 19, 10.1248/bpb.25.19 Galve-Roperh, 2008, Mechanisms of control of neuron survival by the endocannabinoid system, Curr. Pharm. Des., 14, 2279, 10.2174/138161208785740117 Henning, 2008, Nongallated compared with gallated flavan-3-ols in green and black tea are more bioavailable, J. Nutr., 138, 1529S, 10.1093/jn/138.8.1529S Higdon, 2003, Tea catechins and polyphenols: health effects, metabolism, and antioxidant functions, Crit. Rev. Food Sci. Nutr., 43, 89, 10.1080/10408690390826464 Hill, 2007, Can EGCG reduce abdominal fat in obese subjects?, J. Am. Coll. Nutr., 26, 396S, 10.1080/07315724.2007.10719628 Hou, 2007, Green tea proanthocyanidins inhibit cyclooxygenase-2 expression in LPS-activated mouse macrophages: molecular mechanisms and structure–activity relationship, Arch. Biochem. Biophys., 460, 67, 10.1016/j.abb.2007.01.009 Hursel, 2009, Green tea catechin plus caffeine supplementation to a high-protein diet has no additional effect on body weight maintenance after weight loss, Am. J. Clin. Nutr., 89, 822, 10.3945/ajcn.2008.27043 Ikeda, 2005, Tea catechins with a galloyl moiety suppress postprandial hypertriacylglycerolemia by delaying lymphatic transport of dietary fat in rats, J. Nutr., 135, 155, 10.1093/jn/135.2.155 Jeon, 2003, Green tea catechins as a BACE1 (beta-secretase) inhibitor, Bioorg. Med. Chem. Lett., 13, 3905, 10.1016/j.bmcl.2003.09.018 Jhaveri, 2008, Inhibition of fatty acid amide hydrolase and cyclooxygenase-2 increases levels of endocannabinoid related molecules and produces analgesia via peroxisome proliferator-activated receptor-alpha in a model of inflammatory pain, Neuropharmacology, 55, 85, 10.1016/j.neuropharm.2008.04.018 Kakuda, 2002, Neuroprotective effects of the green tea components theanine and catechins, Biol. Pharm. Bull., 25, 1513, 10.1248/bpb.25.1513 Kaur, 2005, Reversal of LPS-induced central and peripheral hyperalgesia by green tea extract, Phytother. Res., 19, 39, 10.1002/ptr.1621 Katavic, 2007, Flavonoids as opioid receptor ligands: identification and preliminary structure-activity relationships, J. Nat. Prod., 70, 1278, 10.1021/np070194x Kao, 2000, Modulation of obesity by a green tea catechin, Am. J. Clin. Nutr., 72, 1232, 10.1093/ajcn/72.5.1232 Keli, 1996, Dietary flavonoids, antioxidant vitamins, and incidence of stroke: the Zutphen study, Arch. Intern. Med., 156, 637, 10.1001/archinte.1996.00440060059007 Kim, 2007, Epigallocatechin gallate, a green tea polyphenol, mediates NO-dependent vasodilation using signaling pathways in vascular endothelium requiring reactive oxygen species and Fyn, J. Biol. Chem., 282, 13736, 10.1074/jbc.M609725200 Kinjo, 2002, Activity-guided fractionation of green tea extract with antiproliferative activity against human stomach cancer cells, Biol. Pharm. Bull., 25, 1238, 10.1248/bpb.25.1238 Kuriyama, 2006, Green tea consumption and cognitive function: a cross-sectional study from the Tsurugaya Project 1, Am. J. Clin. Nutr., 83, 355, 10.1093/ajcn/83.2.355 Lynn, 1994, Localization of cannabinoid receptors and nonsaturable high-density cannabinoid binding sites in peripheral tissues of the rat: implications for receptor-mediated immune modulation by cannabinoids, J. Pharmacol. Exp. Ther., 268, 1612 Maeda-Yamamoto, 2007, In vitro and in vivo anti-allergic effects of ‘benifuuki’ green tea containing O-methylated catechin and ginger extract enhancement, Cytotechnology, 55, 135, 10.1007/s10616-007-9112-1 Matsuda, 1990, Structure of a cannabinoid receptor and functional expression of the cloned cDNA, Nature, 346, 561, 10.1038/346561a0 Munro, 1993, Molecular characterization of a peripheral receptor for cannabinoids, Nature, 365, 61, 10.1038/365061a0 Murase, 2006, Reduction of diet-induced obesity by a combination of tea-catechin intake and regular swimming, Int. J. Obes., 30, 561, 10.1038/sj.ijo.0803135 Nagao, 2009, A catechin-rich beverage improves obesity and blood glucose control in patients with type 2 diabetes, Obesity, 17, 310, 10.1038/oby.2008.505 Okamoto, 2003, Inhibitory effects of green tea catechins on protein tyrosine phosphatase in Prevotella intermedia, Oral Microbiol. Immunol., 18, 192, 10.1034/j.1399-302X.2003.00056.x Pan, 2003, Potential therapeutic properties of green tea polyphenols in Parkinson's disease, Drugs Aging, 20, 711, 10.2165/00002512-200320100-00001 Patra, 2008, Molecular targets of (−)-epigallocatechin-3-gallate (EGCG): specificity and interaction with membrane lipid rafts, J. Physiol. Pharmacol., 59, 217 Richard, 2009, The brain endocannabinoid system in the regulation of energy balance, Best Pract. Res. Clin. Endocrinol. Metab., 23, 17, 10.1016/j.beem.2008.10.007 Rocha, 2007, Antidepressant-like effect of Cecropia glaziouiSneth and its constituents – in vivo and in vitro characterization of the underlying mechanism, Phytomedicine, 14, 396, 10.1016/j.phymed.2007.03.011 Rondanelli, 2009, Administration of a dietary supplement (N-oleyl-phosphatidylethanolamine and epigallocatechin-3-gallate formula) enhances compliance with diet in healthy overweight subjects: a randomized controlled trial, Br. J. Nutr., 101, 457, 10.1017/S0007114508024008 Ruidavets, 2000, Catechin in the Mediterranean diet: vegetable, fruit or wine?, Atherosclerosis, 153, 107, 10.1016/S0021-9150(00)00377-4 Rylski, 1979, The analgesic action of some flavonoids in the hot plate test, Acta Physiol. Pol., 30, 385 Saeki, 2000, Importance of a pyrogallol-type structure in catechin compounds for apoptosis-inducing activity, Phytochemistry, 53, 391, 10.1016/S0031-9422(99)00513-0 Sattayasai, 2008, Biphasic effects of Morus alba leaves green tea extract on mice in chronic forced swimming model, Phytother. Res., 22, 487, 10.1002/ptr.2346 Shen, 2009, Green tea polyphenols and Tai Chi for bone health: designing a placebo-controlled randomized trial, BMC Musculoskelet. Disord., 10, 110, 10.1186/1471-2474-10-110 Singal, 2005, Modulatory role of green tea extract on antinociceptive effect of morphine in diabetic mice, J. Med. Food, 8, 386, 10.1089/jmf.2005.8.386 Stalmach, 2009, Absorption, metabolism and excretion of Choladi green tea flavan-3-ols by humans, Mol. Nutr. Food Res., 53, 44, 10.1002/mnfr.200800169 Tanabe, 2008, Consumption of green and roasted teas and the risk of stroke incidence: results from the Tokamachi–Nakasato cohort study in Japan, Int. J. Epidemiol., 37, 1030, 10.1093/ije/dyn211 Tang, 2007, Effects and mechanisms of catechin for adjuvant arthritis in rats, Adv. Ther., 24, 679, 10.1007/BF02848793 Tedeschi, 2002, Antiinflammatory action of EGCG, the main component of green tea, through STAT-1 inhibition, Ann. N. Y. Acad. Sci., 973, 435, 10.1111/j.1749-6632.2002.tb04678.x Walker, 2005, Cannabinoid mechanisms of pain suppression, Handb. Exp. Pharmacol., 168, 509, 10.1007/3-540-26573-2_17 Wang, 2008, Validation of green tea polyphenol biomarkers in a phase II human intervention trial, Food Chem. Toxicol., 46, 232, 10.1016/j.fct.2007.08.007 Wang, 2003, The galloyl moiety of green tea catechins is the critical structural feature to inhibit fatty-acid synthase, Biochem. Pharmacol., 66, 2039, 10.1016/S0006-2952(03)00585-9 Warden, 2001, Catechins are bioavailable in men and women drinking black tea throughout the day, J. Nutr., 131, 1731, 10.1093/jn/131.6.1731 Woelkart, 2008, CB receptor ligands from plants, Curr. Top. Med. Chem., 8, 173, 10.2174/156802608783498023 Wolfe, 2008, Structure-activity relationships of flavonoids in the cellular antioxidant activity assay, J. Agric. Food Chem., 56, 8404, 10.1021/jf8013074