Catechol O-Methyltransferase: A Review of the Gene and Enzyme
Corresponding author: Dr.Neil McGregor, Faculty of Medicine, Dentistry and Health Sciences. University of Melbourne, 4A Wilmot Street, Malvern East 3145, Austraila; Email: email@example.com
1. Diatchenko L, Slade GD, Nackley AG, Bhalang K, Sigurdsson A et al. Genetic basis for individual variations in pain perception and the development of a chronic pain condition. Hum Mol Genet. 2005, 14(1):135-143.
8. Goertzel BN, Pennachin C, de Souza CL, Gurbaxani B, Maloney EM et al. Combinations of single nucleotide polymorphisms in neuroendocrine effector and receptor genes predict chronic fatigue syndrome. Pharmacogenomics. 2006, 7(3):475-483.
10. Cohen H, Neumann L, Glazer Y, Ebstein RP, Buskila D. The relationship between a common catechol-O-methyltransferase (COMT) polymorphism val(158) met and fibromyalgia. ClinExp Rheumatol. 2009, 27(5 Suppl 56): S51-S56.
12.Tander B, Gunes S, Boke O, Alayli G, Kara N et al. Polymorphisms of the serotonin-2A receptor and catechol-O-methyltransferase genes: a study on fibromyalgia susceptibility. Rheumatol Int. 2008, 28(7): 685-691.
13. Vargas-Alarcon G, Fragoso JM, Cruz-Robles D, Vargas A, Lao-Villadoniga JI et al. Catechol-O-methyltransferase gene haplotypes in Mexican and Spanish patients with fibromyalgia. Arthritis Res Ther. 2007, 9(5): R110.
14.Tander B, Gunes S, Boke O, Alayli G, Kara N et al. Polymorphisms of the serotonin-2A receptor and catechol-O-methyltransferase genes: a study on fibromyalgia susceptibility. Rheumatol Int. 2008, 28(7): 685-691.
15. Hagen K, Pettersen E, Stovner LJ, Skorpen F, Zwart JA. No association between chronic musculoskeletal complaints and Val158Met polymorphism in the Catechol-O-methyltransferase gene. The HUNT study. BMC Musculoskelet Disord. 2006, 7:40.
17. Nackley AG, Shabalina SA, Tchivileva IE, Satterfield K, Korchynskyi O et al. Human catechol-O-methyltransferase haplotypes modulate protein expression by altering mRNA secondary structure. Science. 2006, 314(5807):1930-1933.
18. Nackley AG, Shabalina SA, Lambert JE, Conrad MS, Gibson DG et al. Low enzymatic activity haplotypes of the human catechol- O-methyltransferase gene: enrichment for marker SNPs. PLoS One 2009; 4(4):e5237
21.Tenhunen J. Characterization of the rat catechol-O-methyltransferase gene proximal promoter: identification of a nuclear protein-DNA interaction that contributes to the tissue-specific regulation. DNA Cell Biol. 1996, 15(6): 461-473.
22.Tenhunen J, Salminen M, Lundstrom K, Kiviluoto T, Savolainen R, et al. Genomic organization of the human catechol O-methyltransferase gene and its expression from two distinct promoters. Eur J Biochem. 1994, 223(3):1049-1059.
23.Tenhunen J, Salminen M, Jalanko A, Ukkonen S, Ulmanen I. Structure of the rat catechol-O-methyltransferase gene: separate promoters are used to produce mRNAs for soluble and membrane-bound forms of the enzyme. DNA Cell Biol. 1993,12(3): 253-263.
25. Eisenhofer G, Keiser H, Friberg P, Mezey E, Huynh TT et al. Plasma metanephrines are markers of pheochromocytoma produced by catechol-O-methyltransferase within tumors. J Clin Endocrinol Metab. 1998, 83(6): 2175-2185.
26. Ellingson T, Duddempudi S, Greenberg BD, Hooper D, Eisenhofer G. Determination of differential activities of soluble and membrane-bound catechol-O-methyltransferase in tissues and erythrocytes. J Chromatogr B Biomed Sci Appl. 1999, 729(1-2): 347-353.
28. Mannisto PT, Ulmanen I, Lundstrom K, Taskinen J, Tenhunen J et al. Characteristics of catechol O-methyl-transferase (COMT) and properties of selective COMT inhibitors. Prog Drug Res. 1992, 39: 291-350.
29. Tunbridge EM, Weinberger DR, Harrison PJ. A novel protein isoform of catechol O-methyltransferase (COMT): brain expression analysis in schizophrenia and bipolar disorder and effect of Val158Met genotype. Mol Psychiatry. 2006, 11(2):116- 117.
31. Singh B, Mense SM, Bhat NK, Putty S, Guthiel WA et al. Dietary quercetin exacerbates the development of estrogen-induced breast tumors in female ACI rats. Toxicol Appl Pharmacol 2010, 247(2): 83-90.
33. Smith SB, Maixner DW, Greenspan JD, Dubner R, Fillingim RB et al. Potential genetic risk factors for chronic TMD: genetic associations from the OPPERA case control study. J Pain. 2011, 12(11 Suppl): T92-101.
35. Kerr JR, Burke B, Petty R, Gough J, Fear D et al. Seven genomic subtypes of chronic fatigue syndrome/myalgic encephalomyelitis: a detailed analysis of gene networks and clinical phenotypes. J Clin Pathol. 2008, 61(6):730-739.
36. Hoeger-Bement MK, Sluka KA. Phosphorylation of CREB and mechanical hyperalgesia is reversed by blockade of the cAMP pathway in a time-dependent manner after repeated intramuscular acid injections. J Neurosci. 2003, 23(13):5437- 5445.
39. Brannan K, Kim H, Erickson B, Glover-Cutter K, Kim S et al. mRNA decapping factors and the exonuclease Xrn2 function in widespread premature termination of RNA polymerase II transcription. Mol Cell. 2012, 46(3): 311-324.
42. Huang Y, Liu J, Xu Y, Dai Z, Alves MH. Reduction of insulin resistance in HepG2 cells by knockdown of LITAF expression in human THP-1 macrophages. J Huazhong Univ Sci Technolog Med Sci. 2012, 32(1): 53-58.
43. Merrill JC, You J, Constable C, Leeman SE, Amar S. Wholebody deletion of LPS-induced TNF-alpha factor (LITAF) markedly improves experimental endotoxic shock and inflammatory arthritis. Proc Natl Acad Sci U S A. 2011, 108(52): 21247-21252.
44. Ji ZZ, Dai Z, Xu YC. A new tumor necrosis factor (TNF)-alpha regulator, lipopolysaccharides-induced TNF-alpha factor, is associated with obesity and insulin resistance. Chin Med J (Engl). 2011, 124(2): 177-182.
45. Bolcato-Bellemin AL, Mattei MG, Fenton M, Amar S. Molecular cloning and characterization of mouse LITAF cDNA: role in the regulation of tumor necrosis factor-alpha (TNF-alpha) gene expression. J Endotoxin Res. 2004, 10(1):15-23.
47. Stucchi A, Reed K, O’Brien M, Cerda S, Andrews C et al. A new transcription factor that regulates TNF-alpha gene expression, LITAF, is increased in intestinal tissues from patients with CD and UC. Inflamm Bowel Dis. 2006, 12(7):581-587.
62.Bertocci B, Miggiano V, Da PM, Dembic Z, Lahm HW et al. Human catechol-O-methyltransferase: cloning and expression of the membrane-associated form. Proc Natl Acad Sci U S A. 1991, 88(4): 1416-1420.
63.Nackley AG, Diatchenko L. Assessing potential functionality of catechol-O-methyltransferase (COMT) polymorphisms associated with pain sensitivity and temporomandibular joint disorders. Methods Mol Biol. 2010, 617: 375-393.
64. Doyle AE, Goodman JE, Silber PM, Yager JD. Catechol- O-methyltransferase low activity genotype (COMTLL) is associated with low levels of COMT protein in human hepatocytes. Cancer Lett. 2004, 214(2):189-195.
67. Du X, Schwander M, Moresco EM, Viviani P, Haller C, Hildebrand MS et al. A catechol-O-methyltransferase that is essential for auditory function in mice and humans. Proc Natl Acad Sci U S A. 2008, 105(38):14609-14614.
68. Charif M, Bounaceur S, Abidi O, Nahili H, Rouba H et al. The c.242G>A mutation in LRTOMT gene is responsible for a high prevalence of deafness in the Moroccan population. Mol Biol Rep. 2012, 39(12):11011-11016.
69. Vanwesemael M, Schrauwen I, Ceuppens R, Alasti F, Jorssen E et al. A 1 bp deletion in the dual reading frame deafness gene LRTOMT causes a frameshift from the first into the second reading frame. Am J Med Genet A. 2011, 155A(8):2021-2023.
70. Duman D, Sirmaci A, Cengiz FB, Ozdag H, Tekin M. Screening of 38 genes identifies mutations in 62% of families with nonsyndromic deafness in Turkey. Genet Test Mol Biomarkers. 2011, 15(1-2):29-33.
71. Ahmed ZM, Masmoudi S, Kalay E, Belyantseva IA, Mosrati MA et al. Mutations of LRTOMT, a fusion gene with alternative reading frames, cause nonsyndromic deafness in humans. Nat Genet. 2008, 40(11):1335-1340
72. Zarchi O, Attias J, Raveh E, Basel-Vanagaite L, Saporta L et al. A comparative study of hearing loss in two microdeletion syndromes: velocardiofacial (22q11.2 deletion) and Williams (7q11.23 deletion) syndromes. J Pediatr. 2011, 158(2): 301- 306.
73. Ross CJ, Katzov-Eckert H, Dube MP, Brooks B, Rassekh SR et al. Genetic variants in TPMT and COMT are associated with hearing loss in children receiving cisplatin chemotherapy. Nat Genet. 2009, 41(12):1345-1349.
76. Chen J, Lipska BK, Halim N, Ma QD, Matsumoto M et al. Functional analysis of genetic variation in catechol-O-methyltransferase (COMT): effects on mRNA, protein, and enzyme activity in postmortem human brain. Am J Hum Genet. 2004, 75(5): 807-821.
80. Lotta T, Vidgren J, Tilgmann C, Ulmanen I, Melen K et al. Kinetics of human soluble and membrane-bound catechol O-methyltransferase: a revised mechanism and description of the thermolabile variant of the enzyme. Biochemistry. 1995, 34(13):4202-4210.
82. Malherbe P, Bertocci B, Caspers P, Zurcher G, Da PM. Expression of functional membrane-bound and soluble catechol- O-methyltransferase in Escherichia coli and a mammalian cell line. J Neurochem.1992, 58(5):1782-1789.
83. Borchardt RT, Huber JA, Wu YS. Potential inhibitor of S-adenosylmethionine- dependent methyltransferases. 2. Modification of the base portion of S-adenosylhomocysteine. J Med Chem. 1974, 17(8): 868-873.
84. Borchardt RT, Wu YS. Potential inhibitors of S-adenosylmethionine- dependent methyltransferases. 1. Modification of the amino acid portion of S-adenosylhomocysteine. J Med Chem. 1974, 17(8):862-868.
86. Coward JK, Bussolotti DL, Chang CD. Analogs of S-adenosylhomocysteine as potential inhibitors of biological transmethylation. Inhibition of several methylases by S-tubercidinylhomocysteine. J Med Chem. 1974, 17(12):1286-1289.
88. Coward JK, D’Urso-Scott M, Sweet WD. Inhibition of catechol- O-methyltransferase by S-adenosylhomocysteine and S-adenosylhomocysteine sulfoxide, a potential transition-state analog. Biochem Pharmacol. 1972, 21(8):1200-1203.
90. Maas D, Maret C, Schaade L, Scheithauer S, Ritter K et al. Reactivation of the Epstein-Barr virus from viral latency by an S-adenosylhomocysteine hydrolase/14-3-3 zeta/PLA2-dependent pathway. Med Microbiol Immunol. 2006, 195(4):217-223.
91. Schaade L, Kleines M, Krone B, Hausding M, Walter R, et al. Enhanced transcription of the s-adenosylhomocysteine hydrolase gene precedes Epstein-Barr virus lytic gene activation in ganglioside-stimulated lymphoma cells. Med Microbiol Immunol. 2000, 189(1):13-18.
92 .Lerner AM, Dworkin HJ, Sayyed T, Chang CH, Fitzgerald JT et al. Prevalence of abnormal cardiac wall motion in the cardiomyopathy associated with incomplete multiplication of Epstein-barr Virus and/or cytomegalovirus in patients with chronic fatigue syndrome. In Vivo. 2004, 18(4):417-424.
93. Zhang L, Gough J, Christmas D, Mattey DL, Richards SC et al. Microbial infections in eight genomic subtypes of chronic fatigue syndrome/myalgic encephalomyelitis. J Clin Pathol. 2010, 63(2):156-164.
94. Dickerson FB, Boronow JJ, Stallings C, Origoni AE, Cole S et al. The catechol O-methyltransferase Val158Met polymorphism and herpes simplex virus type 1 infection are risk factors for cognitive impairment in bipolar disorder: additive gene-environmental effects in a complex human psychiatric disorder. Bipolar Disord. 2006, 8(2):124-132.
96. Bouma EM, Riese H, Doornbos B, Ormel J, Oldehinkel AJ. Genetically based reduced MAOA and COMT functioning is associated with the cortisol stress response: a replication study. Mol Psychiatry. 2012, 17(2):119-121.
98. Cusin C, Serretti A, Lattuada E, Lilli R, Lorenzi C et al. Association study of MAO-A, COMT, 5-HT2A, DRD2, and DRD4 polymorphisms with illness time course in mood disorders. Am J Med. Genet 2002, 114(4):380-390.
99. Doornbos B, jck-Brouwer DA, Kema IP, Tanke MA, van Goor SA et al. The development of peripartum depressive symptoms is associated with gene polymorphisms of MAOA, 5-HTT and COMT. Prog Neuropsychopharmacol Biol Psychiatry. 2009, 33(7):1250-1254.
102. Johansson B, Angelo HR, Christensen JK, Moller IW, Ronsted P. Dose-effect relationship of disulfiram in human volunteers. II: A study of the relation between the disulfiram-alcohol reaction and plasma concentrations of acetaldehyde, diethyldithiocarbamic acid methyl ester, and erythrocyte aldehyde dehydrogenase activity. Pharmacol Toxicol. 1991, 68(3):166- 170.
104. Nishimura FT, Kimura Y, Abe S, Fukunaga T, Minami J et al. Effects of functional polymorphisms related to catecholaminergic systems on changes in blood catecholamine and cardiovascular measures after alcohol ingestion in the Japanese population. Alcohol Clin Exp Res. 2008, 32(11):1937-1946.
108. Helkamaa T, Reenila I, Tuominen RK, Soinila S, Vaananen A et al. Increased catechol-O-methyltransferase activity and protein expression in OX-42-positive cells in the substantia nigra after lipopolysaccharide microinfusion. Neurochem Int. 2007, 51(6-7): 412-423.
111. Borroni B, Di LM, Padovani A. Catechol-o-methyltransferase gene polymorphism in dementia with Lewy bodies-related psychosis: evidence for a genetic predisposition. Int Psychogeriatr. 2006, 18(4): 755-757.
112. Seeman P, Weinshenker D, Quirion R, Srivastava LK, Bhardwaj SK et al. Dopamine supersensitivity correlates with D2High states, implying many paths to psychosis. Proc Natl Acad Sci U S A. 2005, 102(9):3513-3518.
115. Tunbridge EM, Huber A, Farrell SM, Stumpenhorst K, Harrison PJ et al. The role of catechol-O-methyltransferase in reward processing and addiction. CNS Neurol Disord Drug Targets. 2012, 11(3): 306-323.
116. Yoshizumi M, Kitagawa T, Hori T, Katoh I, Houchi H et al. Physiological significance of plasma sulfoconjugated dopamine in patients with hypertension–clinical and experimental studies. Life Sci. 1996, 59(4):324-330.
120. Okamoto K, Imbe H, Tashiro A, Kumabe S, Senba E. Blockade of peripheral 5HT3 receptor attenuates the formalin-induced nocifensive behavior in persistent temporomandibular joint inflammation of rat. Neurosci Lett. 2004, 367(2):259-263.
121.Okamoto K, Imbe H, Tashiro A, Kimura A, Donishi T, et al. The role of peripheral 5HT2A and 5HT1A receptors on the orofacial formalin test in rats with persistent temporomandibular joint inflammation. Neuroscience. 2005, 130(2): 465-474.
125. Christidis N, Nilsson A, Kopp S, Ernberg M. Intramuscular injection of granisetron into the masseter muscle increases the pressure pain threshold in healthy participants and patients with localized myalgia. Clin J Pain. 2007, 23(6): 467-472.
127. Voog O, Alstergren P, Leibur E, Kallikorm R, Kopp S. Immediate effects of the serotonin antagonist granisetron on temporomandibular joint pain in patients with systemic inflammatory disorders. Life Sci. 2000, 68(5): 591-602.
129. Benjamin J, Osher Y, Lichtenberg P, Bachner-Melman R, Gritsenko I, et al. An interaction between the catechol O-methyltransferase and serotonin transporter promoter region polymorphisms contributes to tridimensional personality questionnaire persistence scores in normal subjects. Neuropsychobiology. 2000, 41(1): 48-53.
130. Borroni B, Grassi M, Agosti C, Archetti S, Costanzi C et al. Cumulative effect of COMT and 5-HTTLPR polymorphisms and their interaction with disease severity and comorbidities on the risk of psychosis in Alzheimer disease. Am J Geriatr Psychiatry. 2006, 14(4): 343-351.
132. De L, V, Strauss J, Kennedy JL. Power based association analysis (PBAT) of serotonergic and noradrenergic polymorphisms in bipolar patients with suicidal behaviour. Prog Neuropsychopharmacol Biol Psychiatry. 2008, 32(1):197-203.
134. Lu F, Zahid M, Saeed M, Cavalieri EL, et al. Estrogen metabolism and formation of estrogen-DNA adducts in estradiol- treated MCF-10F cells. The effects of 2,3,7,8-tetrachlorodibenzo- p-dioxin induction and catechol-O-methyltransferase inhibition. J Steroid Biochem Mol Biol. 2007, 105(1-5):150- 158.
139. Butterworth M, Lau SS, Monks TJ. 17 beta-Estradiol metabolism by hamster hepatic microsomes. Implications for the catechol-O-methyl transferase-mediated detoxication of catechol estrogens. Drug Metab Dispos. 1996, 24(5): 588-594.
140. Fernandez-Ruiz JJ, Bukhari AR, Martinez-Arrieta R, Tresguerres JA, Ramos JA. Effects of estrogens and progesterone on the catecholaminergic activity of the adrenal medulla in female rats. Life Sci 1988, 42(9):1019-1028.
142. Greenlee H, Chen Y, Kabat GC, Wang Q, Kibriya MG et al. Variants in estrogen metabolism and biosynthesis genes and urinary estrogen metabolites in women with a family history of breast cancer. Breast Cancer Res Treat. 2007, 102(1):111- 117.
144. Eriksson AL, Suuriniemi M, Mahonen A, Cheng S, Ohlsson C. The COMT val158met polymorphism is associated with early pubertal development, height and cortical bone mass in girls. Pediatr Res. 2005, 58(1):71-77.
146 .Cribb AE, Joy KM, Guernsey J, Dryer D, Hender K et al. CYP17, catechol-o-methyltransferase, and glutathione transferase M1 genetic polymorphisms, lifestyle factors, and breast cancer risk in women on Prince Edward Island. Breast J. 2011, 17(1): 24-31.
148. Lin WY, Chou YC, Wu MH, Jeng YL, Huang HB et al. Polymorphic catechol-O-methyltransferase gene, duration of estrogen exposure, and breast cancer risk: a nested case-control study in Taiwan. Cancer Detect Prev. 2005, 29(5): 427-432.
149.Hu Z, Song CG, Lu JS, Luo JM, Shen ZZ, Huang W et al. A multigenic study on breast cancer risk associated with genetic polymorphisms of ER Alpha, COMT and CYP19 gene in BRCA1/ BRCA2 negative Shanghai women with early onset breast cancer or affected relatives. J Cancer Res Clin Oncol. 2007, 133(12): 969-978.
151. Liang S, Liu X, Fan P, Liu R, Zhang J et al. Association between Val158Met functional polymorphism in the COMT gene and risk of preeclampsia in a Chinese population. Arch Med Res. 2012, 43(2):154-158.
152. Parvez H, Parvez S. The effects of metopirone and adrenalectomy on the regulation of the enzymes monoamine oxidase and catechol-O-methyl transferase in different brain regions. J Neurochem. 1973, 20(4):1011-1020.
153.Jabbi M, Kema IP, van der Pompe G, te Meerman GJ, Ormel J et al. Catechol-o-methyltransferase polymorphism and susceptibility to major depressive disorder modulates psychological stress response. Psychiatr Genet. 2007, 17(3):183-193.
154.Yoshizumi M, Kitagawa T, Hori T, Katoh I, Houchi H et al. Physiological significance of plasma sulfoconjugated dopamine in patients with hypertension–clinical and experimental studies. Life Sci. 1996, 59(4): 324-330.
157. Htun NC, Miyaki K, Song Y, Ikeda S, Shimbo T et al. Association of the catechol-O-methyl transferase gene Val158Met polymorphism with blood pressure and prevalence of hypertension: interaction with dietary energy intake. Am J Hypertens. 2011, 24(9):1022-1026.
158. Hirano Y, Tsunoda M, Shimosawa T, Matsui H, Fujita T et al. Suppression of catechol-O-methyltransferase activity through blunting of alpha2-adrenoceptor can explain hypertension in Dahl salt-sensitive rats. Hypertens Res. 2007, 30(3): 269-278.
160. Eriksson AL, Skrtic S, Niklason A, Hulten LM, Wiklund O et al. Association between the low activity genotype of catechol- O-methyltransferase and myocardial infarction in a hypertensive population. Eur Heart J. 2004, 25(5):386-391.
161. Almeida L, Falcao A, Vaz-da-Silva M, Nunes T, Santos AT, Rocha JF et al. Effect of nebicapone on the pharmacokinetics and pharmacodynamics of warfarin in healthy subjects. Eur J Clin Pharmacol. 2008, 64(10): 961-966.
162.Dingemanse J, Meyerhoff C, Schadrack J. Effect of the catechol- O-methyltransferase inhibitor entacapone on the steadystate pharmacokinetics and pharmacodynamics of warfarin. Br J Clin Pharmacol. 2002, 53(5):485-491.
163. Chen J, Song J, Yuan P, Tian Q, Ji Y et al. Orientation and cellular distribution of membrane-bound catechol-O-methyltransferase in cortical neurons: implications for drug development. J Biol Chem. 2011, 286(40):34752-34760.
164. Happonen P, Voutilainen S, Tuomainen TP, Salonen JT. Catechol- o-methyltransferase gene polymorphism modifies the effect of coffee intake on incidence of acute coronary events. PLoS One. 2006, 1:e117.
165. Bhaird NN, Fowler CJ, Thorberg O, Tipton KF. Involvement of catechol-O-methyl transferase in the metabolism of the putative dopamine autoreceptor agonist 3-PPP(3-(3-hydroxyphenyl)- N-n-propylpiperidine). Biochem Pharmacol. 1985, 34(19):3599-3601.
166. Brannan T, Prikhojan A, Yahr MD. Peripheral and central inhibitors of catechol-O-methyl transferase: effects on liver and brain COMT activity and L-DOPA metabolism. J Neural Transm. 1997, 104(1):77-87.
168. Pizarro N, Farre M, Pujadas M, Peiro AM, Roset PN et al. Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites in human samples including the catechol-type metabolite (3,4-dihydroxymethamphetamine). Drug Metab Dispos. 2004, 32(9):1001-1007.
172. Yan M, Webster LT, Jr., Blumer JL. Kinetic interactions of dopamine and dobutamine with human catechol-O-methyltransferase and monoamine oxidase in vitro. J Pharmacol Exp Ther. 2002, 301(1):315-321.
177. Bowers-Komro DM, McCormick DB, King GA, Sweeny JG, Iacobucci GA. Confirmation of 2-O-methyl ascorbic acid as the product from the enzymatic methylation of L-ascorbic acid by catechol-O-methyltransferase. Int J Vitam Nutr Res. 1982,52(2):186-193.
178. Salama SA, Kamel MW, Botting S, Salih SM, Borahay MA et al. Catechol-o-methyltransferase expression and 2-methoxyestradiol affect microtubule dynamics and modify steroid receptor signaling in leiomyoma cells. PLoS One. 2009, 4(10):e7356.
179. Salama SA, Kamel MW, az-Arrastia CR, Xu X, Veenstra TD et al. Effect of tumor necrosis factor-alpha on estrogen metabolism and endometrial cells: potential physiological and pathological relevance. J Clin Endocrinol Metab. 2009, 94(1):285- 293.
183. McCann SE, Wactawski-Wende J, Kufel K, Olson J, Ovando B et al. Changes in 2-hydroxyestrone and 16alpha-hydroxyestrone metabolism with flaxseed consumption: modification by COMT and CYP1B1 genotype. Cancer Epidemiol Biomarkers Prev. 2007, 16(2):256-262.
185. Dubey RK, Gillespie DG, Zacharia LC, Rosselli M, Korzekwa KR et al. Methoxyestradiols mediate the antimitogenic effects of estradiol on vascular smooth muscle cells via estrogen receptor- independent mechanisms. Biochem Biophys Res Commun. 2000, 278(1):27-33.
186. Dubey RK, Gillespie DG, Zacharia LC, Rosselli M, Imthurn B, et al. Methoxyestradiols mediate the antimitogenic effects of locally applied estradiol on cardiac fibroblast growth. Hypertension. 2002, 39(2 Pt 2):412-417.
187. Dubey RK, Gillespie DG, Keller PJ, Imthurn B, Zacharia LC et al. Role of methoxyestradiols in the growth inhibitory effects of estradiol on human glomerular mesangial cells. Hypertension. 2002, 39(2 Pt 2):418-424.
190. Quiram DR, Weinshilboum RM. Catechol-o-methyltransferase in rat erythrocyte and three other tissues: comparison of biochemical properties after removal of inhibitory calcium. J Neurochem. 1976, 27(5): 1197-1203.
194. van Duursen MB, Sanderson JT, de Jong PC, Kraaij M, van den BM. Phytochemicals inhibit catechol-O-methyltransferase activity in cytosolic fractions from healthy human mammary tissues: implications for catechol estrogen-induced DNA damage. Toxicol Sci. 2004, 81(2):316-324.
195. Nagai M, Conney AH, Zhu BT. Strong inhibitory effects of common tea catechins and bioflavonoids on the O-methylation of catechol estrogens catalyzed by human liver cytosolic catechol-O-methyltransferase. Drug Metab Dispos. 2004, 32(5): 497-504.
199. Zhu BT, Ezell EL, Liehr JG. Catechol-O-methyltransferase- catalyzed rapid O-methylation of mutagenic flavonoids. Metabolic inactivation as a possible reason for their lack of carcinogenicity in vivo. J Biol Chem. 1994, 269(1): 292-299.
200. Zhu BT, Liehr JG. Inhibition of catechol O-methyltransferase catalyzed O-methylation of 2- and 4-hydroxyestradiol by quercetin. Possible role in estradiol-induced tumorigenesis. J Biol Chem. 1996, 271(3):1357-1363.
206. Zhu BT, Wang P, Nagai M, Wen Y, Bai HW. Inhibition of human catechol-O-methyltransferase (COMT)-mediated O-methylation of catechol estrogens by major polyphenolic components present in coffee. J Steroid Biochem Mol Biol. 2009, 113(1-2):65-74.
207. Anning EN, Bryan LJ, O’Donnell SR. The extraneuronal accumulation of isoprenaline in trachea and atria of guinea-pig and cat: a fluorescence histochemical study. Br J Pharmacol. 1979, 65(2):175-182.
208. O’Donnell SR, Saar N. The uptake kinetics and metabolism of extraneuronal noradrenaline in guinea-pig trachea as studied with quantitative fluorescence microphotometry. Br J Pharmacol. 1978, 62(2):235-239.
209. Brown AL, Lane J, Holyoak C, Nicol B, Mayes AE et al. Health effects of green tea catechins in overweight and obese men: a randomised controlled cross-over trial. Br J Nutr. 2011, 106(12):1880-1889.
210. Chen D, Wang CY, Lambert JD, Ai N, Welsh WJ et al. Inhibition of human liver catechol-O-methyltransferase by tea catechins and their metabolites: structure-activity relationship and molecular-modeling studies. Biochem Pharmacol. 2005, 69(10):1523-1531.
211. Kuhnle G, Spencer JP, Schroeter H, Shenoy B, Debnam ES et al. Epicatechin and catechin are O-methylated and glucuronidated in the small intestine. Biochem Biophys Res Commun. 2000, 277(2):507-512.
212. Nagai M, Conney AH, Zhu BT. Strong inhibitory effects of common tea catechins and bioflavonoids on the O-methylation of catechol estrogens catalyzed by human liver cytosolic catechol-O-methyltransferase. Drug Metab Dispos. 2004, 32(5):497-504.
213. Kadowaki M, Ootani E, Sugihara N, Furuno K. Inhibitory effects of catechin gallates on o-methyltranslation of protocatechuic acid in rat liver cytosolic preparations and cultured hepatocytes. Biol Pharm Bull. 2005, 28(8):1509-1513.
216. Tilgmann C, Kalkkinen N. Purification and partial sequence analysis of the soluble catechol-O-methyltransferase from human placenta: comparison to the rat liver enzyme. Biochem Biophys Res Commun. 1991, 174(2):995-1002.