Pathways Knowlegdes
Necessitatibus eius consequatur ex aliquid fuga eum quidem sint consectetur velit
| Pathway | DOIs | Note |
|---|---|---|
| coumarin biosynthesis (via 2-coumarate) Accession ID: BioCyc:META_PWY-5176 |
|
Curini M, Cravotto G, Epifano F, Giannone G. Chemistry and biological activity of natural and synthetic prenyloxycoumarins. Curr Med Chem. 2006;13(2):199–222. doi: 10.2174/092986706775197890. PMID: 16472213.; Lacy A, O'Kennedy R. Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer. Curr Pharm Des. 2004;10(30):3797–811. doi: 10.2174/1381612043382693. PMID: 15579072.; Fylaktakidou KC, Hadjipavlou-Litina DJ, Litinas KE, Nicolaides DN. Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activities. Curr Pharm Des. 2004;10(30):3813–33. doi: 10.2174/1381612043382710. PMID: 15579073.; Oba K, Conn EE, Canut H, Boudet AM. Subcellular Localization of 2-(beta-d-Glucosyloxy)-Cinnamic Acids and the Related beta-glucosidase in Leaves of Melilotus alba Desr. Plant Physiol. 1981 Dec;68(6):1359–63. PMID: 16662108; PMCID: PMC426103.; Poulton JE, McRee DE, Conn EE. Intracellular Localization of Two Enzymes Involved in Coumarin Biosynthesis in Melilotus alba. Plant Physiol. 1980 Feb 01;65(2):171–5. doi: 10.1104/pp.65.2.171.; Gestetner B, Conn EE. The 2-hydroxylation of trans-cinnamic acid by chloroplasts from Melilotus alba desr. Archives of Biochemistry and Biophysics. 1974 Aug;163(2):617–24. doi: 10.1016/0003-9861(74)90522-0.; Kleinhofs A, Haskins FA, Gorz HJ. Ultraviolet-induced isomerization of beta-D-glucosyl omicron-hydroxycinnamic acid on filter paper. J Chromatogr. 1966 Apr;22(1):184–6. doi: 10.1016/s0021-9673(01)97086-4. PMID: 5921806.; Haskins FA, Williams LG, Gorz HJ. Light-Induced Trans to Cis Conversion of ß-d-Glucosyl o-Hydroxycinnamic Acid in Melilotus alba Leaves. Plant Physiol. 1964 Sep 01;39(5):777–81. doi: 10.1104/pp.39.5.777.; Stoker JR. The biosynthesis of coumarin in Melilotus alba. Biochemical and Biophysical Research Communications. 1963 Dec;14(1):17–20. doi: 10.1016/0006-291x(63)90203-1.; Stoker JR, Bellis DM. The Biosynthesis of Coumarin in Melilotus Alba. Journal of Biological Chemistry. 1962 Jul;237(7):2303–5. doi: 10.1016/s0021-9258(19)63437-x.; Kosuge T. Studies on the identity of bound coumarin in sweet clover. Archives of Biochemistry and Biophysics. 1961 Nov;95(2):211–8. doi: 10.1016/0003-9861(61)90137-0.; KOUKOL J, CONN EE. The metabolism of aromatic compounds in higher plants. IV. Purification and properties of the phenylalanine deaminase of Hordeum vulgare. J Biol Chem. 1961 Oct;236():2692–8. PMID: 14458851.; Kosuge T, Conn EE. The Metabolism of Aromatic Compounds in Higher Plants. Journal of Biological Chemistry. 1959 Aug;234(8):2133–7. doi: 10.1016/s0021-9258(18)69879-5. |
| nicotine degradation IV Accession ID: BioCyc:META_PWY66-201 |
|
Hukkanen J, Jacob P, Benowitz NL. Metabolism and disposition kinetics of nicotine. Pharmacol Rev. 2005 Mar;57(1):79–115. doi: 10.1124/pr.57.1.3. PMID: 15734728.; Meger M, Meger-Kossien I, Schuler-Metz A, Janket D, Scherer G. Simultaneous determination of nicotine and eight nicotine metabolites in urine of smokers using liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Oct 05;778(1-2):251–61. doi: 10.1016/s0378-4347(01)00451-0. PMID: 12376133.; Pankow JF. A consideration of the role of gas/particle partitioning in the deposition of nicotine and other tobacco smoke compounds in the respiratory tract. Chem Res Toxicol. 2001 Nov;14(11):1465–81. doi: 10.1021/tx0100901. PMID: 11712903.; Hecht SS, Hochalter JB, Villalta PW, Murphy SE. 2'-Hydroxylation of nicotine by cytochrome P450 2A6 and human liver microsomes: Formation of a lung carcinogen precursor. Proc. Natl. Acad. Sci. U.S.A. 2000 Oct 24;97(23):12493–7. doi: 10.1073/pnas.220207697.; Hecht SS, Carmella SG, Murphy SE. Effects of watercress consumption on urinary metabolites of nicotine in smokers. Cancer Epidemiol Biomarkers Prev. 1999 Oct;8(10):907–13. PMID: 10548320.; Rose JE, Behm FM, Westman EC, Coleman RE. Arterial nicotine kinetics during cigarette smoking and intravenous nicotine administration: implications for addiction. Drug Alcohol Depend. 1999 Sep 01;56(2):99–107. doi: 10.1016/s0376-8716(99)00025-3. PMID: 10482401.; Perry DC, Dávila-Garci´a MI, Stockmeier CA, Kellar KJ. Increased Nicotinic Receptors in Brains from Smokers: Membrane Binding and Autoradiography Studies. The Journal of Pharmacology and Experimental Therapeutics. 1999 Jun;289(3):1545–52. doi: 10.1016/s0022-3565(24)38304-1.; Jacob P, Yu L, Shulgin AT, Benowitz NL. Minor tobacco alkaloids as biomarkers for tobacco use: comparison of users of cigarettes, smokeless tobacco, cigars, and pipes. Am J Public Health. 1999 May;89(5):731–6. PMID: 10224986; PMCID: PMC1508721.; Hecht SS, Hatsukami DK, Bonilla LE, Hochalter JB. Quantitation of 4-oxo-4-(3-pyridyl)butanoic acid and enantiomers of 4-hydroxy-4-(3-pyridyl)butanoic acid in human urine: A substantial pathway of nicotine metabolism. Chem Res Toxicol. 1999 Feb;12(2):172–9. doi: 10.1021/tx980214i. PMID: 10027795.; Eldirdiri N, Ulgen M, Jacob P, Gorrod JW. The in vitro metabolism of norcotinine and related biotransformation products by microsomal preparations. European Journal of Drug Metabolism and Pharmacokinetics. 1997 Dec;22(4):385–90. doi: 10.1007/bf03190974.; Zevin S, Jacob P, Benowitz N. Cotinine effects on nicotine metabolism. Clinical Pharmacology & Therapeutics. 1997 Jun 19;61(6):649–54. doi: 10.1016/s0009-9236(97)90099-0.; Lunell E, Bergström M, Antoni G, Långström B, Nordberg A. Nicotine deposition and body distribution from a nicotine inhaler and a cigarette studied with positron emission tomography. Clinical Pharmacology & Therapeutics. 1996 May 20;59(5):593–4. doi: 10.1016/s0009-9236(96)90188-5.; Benowitz NL. Pharmacology of nicotine: addiction and therapeutics. Annu Rev Pharmacol Toxicol. 1996;36():597–613. doi: 10.1146/annurev.pa.36.040196.003121. PMID: 8725403.; Benowitz NL, Jacob P. Metabolism of nicotine to cotinine studied by a dual stable isotope method. Clinical Pharmacology & Therapeutics. 1994 Nov 09;56(5):483–93. doi: 10.1038/clpt.1994.169.; Benowitz NL, Jacob P, Fong I, Gupta S. Nicotine metabolic profile in man: comparison of cigarette smoking and transdermal nicotine. The Journal of Pharmacology and Experimental Therapeutics. 1994 Jan;268(1):296–303. doi: 10.1016/s0022-3565(25)38479-x.; Henningfield JE, Keenan RM. Nicotine delivery kinetics and abuse liability. Journal of Consulting and Clinical Psychology. 1993;61(5):743–50. doi: 10.1037//0022-006x.61.5.743.; Cashman JR, Park SB, Yang ZC, Wrighton SA, Jacob P, Benowitz NL. Metabolism of nicotine by human liver microsomes: stereoselective formation of trans-nicotine N'-oxide. Chem Res Toxicol. 1992 Sep;5(5):639–46. doi: 10.1021/tx00029a008. PMID: 1446003.; Byrd GD, Chang KM, Greene JM, deBethizy JD. Evidence for urinary excretion of glucuronide conjugates of nicotine, cotinine, and trans-3'-hydroxycotinine in smokers. Drug Metabolism and Disposition. 1992 Mar;20(2):192–7. doi: 10.1016/s0090-9556(25)08565-4.; Dwoskin LP, Leibee LL, Jewell AL, Fang ZX, Crooks PA. Inhibition of [3H]dopamine uptake into rat striatal slices by quaternary N-methylated nicotine metabolites. Life Sci. 1992;50(25):PL233–7. doi: 10.1016/0024-3205(92)90533-u. PMID: 1593921.; Kyerematen GA, Morgan ML, Chattopadhyay B, deBethizy JD, Vesell ES. Disposition of nicotine and eight metabolites in smokers and nonsmokers: identification in smokers of two metabolites that are longer lived than cotinine. Clin Pharmacol Ther. 1990 Dec;48(6):641–51. doi: 10.1038/clpt.1990.208. PMID: 2249376.; Benowitz NL. Drug therapy. Pharmacologic aspects of cigarette smoking and nicotine addiction. N Engl J Med. 1988 Nov 17;319(20):1318–30. doi: 10.1056/nejm198811173192005. PMID: 3054551.; Benowitz NL, Porchet H, Sheiner L, Jacob P. Nicotine absorption and cardiovascular effects with smokeless tobacco use: Comparison with cigarettes and nicotine gum. Clinical Pharmacology & Therapeutics. 1988 Jul 28;44(1):23–8. doi: 10.1038/clpt.1988.107.; Crooks PA, Godin CS. N-methylation of nicotine enantiomers by human liver cytosol. J Pharm Pharmacol. 1988 Feb;40(2):153–4. doi: 10.1111/j.2042-7158.1988.tb05207.x. PMID: 2897456.; Peterson LA, Trevor A, Castagnoli N. Stereochemical studies on the cytochrome P-450 catalyzed oxidation of (S)-nicotine to the (S)-nicotine delta 1'(5')-iminium species. J Med Chem. 1987 Feb;30(2):249–54. doi: 10.1021/jm00385a004. PMID: 3806608.; Neurath GB, Dünger M, Orth D, Pein FG. Trans-3'-hydroxycotinine as a main metabolite in urine of smokers. International Archives of Occupational and Environmental Health. 1987 Feb;59(2):199–201. doi: 10.1007/bf00378497.; Benowitz NL, Jacob P. Daily intake of nicotine during cigarette smoking. Clinical Pharmacology & Therapeutics. 1984 Apr 14;35(4):499–504. doi: 10.1038/clpt.1984.67.; Hibberd AR, Gorrod JW. Nicotine delta 1 '(5)' iminium ion: a reactive intermediate in nicotine metabolism. Adv Exp Med Biol. 1981;136 Pt B():1121–31. PMID: 6896399.; Nguyen TL, Gruenke LD, Castagnoli N. Metabolic oxidation of nicotine to chemically reactive intermediates. J Med Chem. 1979 Mar;22(3):259–63. doi: 10.1021/jm00189a008. PMID: 423207.; Murphy PJ. Enzymatic oxidation of nicotine to nicotine 1'(5') iminium ion. A newly discovered intermediate in the metabolism of nicotine. J Biol Chem. 1973 Apr 25;248(8):2796–800. PMID: 4144545.; Beckett AH, Gorrod JW, Jenner P. Absorption of (-)-nicotine-l-N-oxide in man and its reduction in the gastrointestinal tract. J Pharm Pharmacol. 1970 Sep;22(9):722–3. doi: 10.1111/j.2042-7158.1970.tb12767.x. PMID: 4394772.; McKennis H, Schwartz SL, Bowman ER. Alternate Routes in the Metabolic Degradation of the Pyrrolidine Ring of Nicotine. Journal of Biological Chemistry. 1964 Nov;239(11):3990–6. doi: 10.1016/s0021-9258(18)91232-9.; PAPADOPOULOS NM. FORMATION OF NORNICOTINE AND OTHER METABOLITES FROM NICOTINE IN VITRO AND IN VIVO. Can J Biochem. 1964 Apr;42():435–42. doi: 10.1139/o64-051. PMID: 14166990.; McKennis H, Turnbull LB, Bowman ER. N-Methylation of Nicotine and Cotinine in Vivo. Journal of Biological Chemistry. 1963 Feb;238(2):719–23. doi: 10.1016/s0021-9258(18)81325-4.; Bowman ER, McKennis H. STUDIES ON THE METABOLISM OF (-)-COTININE IN THE HUMAN. The Journal of Pharmacology and Experimental Therapeutics. 1962 Mar;135(3):306–11. doi: 10.1016/s0022-3565(25)26236-x.; WADA E, BOWMAN ER, TURNBULL LB, McKENNIS H. Norcotinine (desmethylcotinine) as a urinary metabolite of nornicotine. J Med Pharm Chem. 1961 Jul 01;4():21–30. doi: 10.1021/jm50017a002. PMID: 14004224. |
| coumarin biosynthesis (via 2-coumarate) Accession ID: BioCyc:ARA_PWY-5176 |
|
Curini M, Cravotto G, Epifano F, Giannone G. Chemistry and biological activity of natural and synthetic prenyloxycoumarins. Curr Med Chem. 2006;13(2):199–222. doi: 10.2174/092986706775197890. PMID: 16472213.; Lacy A, O'Kennedy R. Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer. Curr Pharm Des. 2004;10(30):3797–811. doi: 10.2174/1381612043382693. PMID: 15579072.; Fylaktakidou KC, Hadjipavlou-Litina DJ, Litinas KE, Nicolaides DN. Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activities. Curr Pharm Des. 2004;10(30):3813–33. doi: 10.2174/1381612043382710. PMID: 15579073.; Oba K, Conn EE, Canut H, Boudet AM. Subcellular Localization of 2-(beta-d-Glucosyloxy)-Cinnamic Acids and the Related beta-glucosidase in Leaves of Melilotus alba Desr. Plant Physiol. 1981 Dec;68(6):1359–63. PMID: 16662108; PMCID: PMC426103.; Poulton JE, McRee DE, Conn EE. Intracellular Localization of Two Enzymes Involved in Coumarin Biosynthesis in Melilotus alba. Plant Physiol. 1980 Feb 01;65(2):171–5. doi: 10.1104/pp.65.2.171.; Gestetner B, Conn EE. The 2-hydroxylation of trans-cinnamic acid by chloroplasts from Melilotus alba desr. Archives of Biochemistry and Biophysics. 1974 Aug;163(2):617–24. doi: 10.1016/0003-9861(74)90522-0.; Kleinhofs A, Haskins FA, Gorz HJ. Ultraviolet-induced isomerization of beta-D-glucosyl omicron-hydroxycinnamic acid on filter paper. J Chromatogr. 1966 Apr;22(1):184–6. doi: 10.1016/s0021-9673(01)97086-4. PMID: 5921806.; Haskins FA, Williams LG, Gorz HJ. Light-Induced Trans to Cis Conversion of ß-d-Glucosyl o-Hydroxycinnamic Acid in Melilotus alba Leaves. Plant Physiol. 1964 Sep 01;39(5):777–81. doi: 10.1104/pp.39.5.777.; Stoker JR. The biosynthesis of coumarin in Melilotus alba. Biochemical and Biophysical Research Communications. 1963 Dec;14(1):17–20. doi: 10.1016/0006-291x(63)90203-1.; Stoker JR, Bellis DM. The Biosynthesis of Coumarin in Melilotus Alba. Journal of Biological Chemistry. 1962 Jul;237(7):2303–5. doi: 10.1016/s0021-9258(19)63437-x.; Kosuge T. Studies on the identity of bound coumarin in sweet clover. Archives of Biochemistry and Biophysics. 1961 Nov;95(2):211–8. doi: 10.1016/0003-9861(61)90137-0.; KOUKOL J, CONN EE. The metabolism of aromatic compounds in higher plants. IV. Purification and properties of the phenylalanine deaminase of Hordeum vulgare. J Biol Chem. 1961 Oct;236():2692–8. PMID: 14458851.; Kosuge T, Conn EE. The Metabolism of Aromatic Compounds in Higher Plants. Journal of Biological Chemistry. 1959 Aug;234(8):2133–7. doi: 10.1016/s0021-9258(18)69879-5. |
| coumarin metabolism (to melilotic acid) Accession ID: BioCyc:META_PWY-5319 |
|
KOUKOL J, CONN EE. The metabolism of aromatic compounds in higher plants. IV. Purification and properties of the phenylalanine deaminase of Hordeum vulgare. J Biol Chem. 1961 Oct;236():2692–8. PMID: 14458851.; Kosuge T, Conn EE. The Metabolism of Aromatic Compounds in Higher Plants. Journal of Biological Chemistry. 1959 Aug;234(8):2133–7. doi: 10.1016/s0021-9258(18)69879-5. |
| coumarin biosynthesis (via 2-coumarate) Accession ID: BioCyc:THAPS_PWY-5176 |
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| Metabolism and regulation Accession ID: Plant Reactome:R-OSA-2744345 |
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| Secondary metabolism Accession ID: Plant Reactome:R-OSA-2744344 |
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Perera I, Seneweera S, Hirotsu N. Manipulating the Phytic Acid Content of Rice Grain Toward Improving Micronutrient Bioavailability. Rice (N Y). 2018 Jan 11;11(1):4. PMID: 29327163; PMCID: PMC5764899.; Lam PY, Liu H, Lo C. Completion of Tricin Biosynthesis Pathway in Rice: Cytochrome P450 75B4 Is a Unique Chrysoeriol 5'-Hydroxylase. Plant Physiol. 2015 Aug;168(4):1527–36. PMID: 26082402; PMCID: PMC4528758.; Lam PY, Zhu FY, Chan WL, Liu H, Lo C. Cytochrome P450 93G1 Is a Flavone Synthase II That Channels Flavanones to the Biosynthesis of Tricin O-Linked Conjugates in Rice. Plant Physiol. 2014 Jul;165(3):1315–27. PMID: 24843076; PMCID: PMC4081339.; Suzuki M, Tanaka K, Kuwano M, Yoshida KT. Expression pattern of inositol phosphate-related enzymes in rice (Oryza sativa L.): implications for the phytic acid biosynthetic pathway. Gene. 2007 Dec 15;405(1-2):55–64. doi: 10.1016/j.gene.2007.09.006. PMID: 17961936.; Shimura K, Okada A, Okada K, Jikumaru Y, Ko K, Toyomasu T, Sassa T, Hasegawa M, Kodama O, Shibuya N, Koga J, Nojiri H, Yamane H. Identification of a Biosynthetic Gene Cluster in Rice for Momilactones. Journal of Biological Chemistry. 2007 Nov;282(47):34013–8. doi: 10.1074/jbc.m703344200. |
| Coumarin biosynthesis (via 2-coumarate) Accession ID: Plant Reactome:R-OSA-1119284 |
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| coumarin biosynthesis (via 2-coumarate) Accession ID: PlantCyc:SPENNELLII_PWY-5176 |
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| coumarin biosynthesis (via 2-coumarate) Accession ID: PlantCyc:SUGARBEET_PWY-5176 |
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| coumarin biosynthesis (via 2-coumarate) Accession ID: PlantCyc:ALYRATA_PWY-5176 |
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| coumarin biosynthesis (via 2-coumarate) Accession ID: PlantCyc:TPARVULA_PWY-5176 |
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| coumarin biosynthesis (via 2-coumarate) Accession ID: PlantCyc:BRACHYPODIUM_PWY-5176 |
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| coumarin biosynthesis (via 2-coumarate) Accession ID: PlantCyc:CACUMINATA_PWY-5176 |
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| coumarin biosynthesis (via 2-coumarate) Accession ID: PlantCyc:CANNUUM_PWY-5176 |
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| coumarin biosynthesis (via 2-coumarate) Accession ID: PlantCyc:CARNATION_PWY-5176 |
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| coumarin biosynthesis (via 2-coumarate) Accession ID: PlantCyc:CARROT_PWY-5176 |
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| coumarin biosynthesis (via 2-coumarate) Accession ID: PlantCyc:RUBBERTREE_PWY-5176 |
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| coumarin biosynthesis (via 2-coumarate) Accession ID: PlantCyc:CLEMENTINE_PWY-5176 |
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| coumarin biosynthesis (via 2-coumarate) Accession ID: PlantCyc:CSATIVA_PK_PWY-5176 |
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