Formate: The Neglected Member of One-Carbon Metabolism

Annual Review of Nutrition

Volumn 36, Issue , 2016, Pages 369-388

  Brosnan, Margaret E ^a   Brosnan, John T ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

Amino acids; Methylation reactions; Neural tube defects; Purine synthesis; Tetrahydrofolate; Thymidylate synthesis

Indexed keywords

CATALASE; FOLIC ACID; FORMIC ACID; FORMIC ACID DERIVATIVE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; PURINE DERIVATIVE; THYMIDINE PHOSPHATE;

CARBON METABOLISM; EMBRYO DEVELOPMENT; ENZYME METABOLISM; ENZYME SYNTHESIS; FETUS DEVELOPMENT; FOLATE METABOLISM; HUMAN; LAMB; MITOCHONDRION; NEOPLASM; NEURAL TUBE DEFECT; NONHUMAN; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; REVIEW; VITAMIN DEFICIENCY; ANIMAL; BIOLOGICAL MODEL; BIOSYNTHESIS; BLOOD; DIETARY SUPPLEMENT; DNA METHYLATION; ENZYMOLOGY; FEMALE; GENETIC EPIGENESIS; MALE; MATERNAL NUTRITION; METABOLISM; METHYLATION; NEURAL TUBE DEFECTS; PENTOSE PHOSPHATE CYCLE; PREGNANCY; PROTEIN PROCESSING; RNA PROCESSING;

ANIMALS; DIETARY SUPPLEMENTS; DNA METHYLATION; EPIGENESIS, GENETIC; FEMALE; FETAL DEVELOPMENT; FORMATES; HUMANS; MALE; MATERNAL NUTRITIONAL PHYSIOLOGICAL PHENOMENA; METHYLATION; MITOCHONDRIA; MODELS, BIOLOGICAL; NADP; NEURAL TUBE DEFECTS; PENTOSE PHOSPHATE PATHWAY; PREGNANCY; PROTEIN PROCESSING, POST-TRANSLATIONAL; PURINES; RNA PROCESSING, POST-TRANSCRIPTIONAL; THYMIDINE MONOPHOSPHATE;

EID: 84979075821     PISSN: 01999885     EISSN: 15454312     Source Type: Book Series    
DOI: 10.1146/annurev-nutr-071715-050738     Document Type: Review

References (82)

1. Dietary Reference Intakes for Energy, Carbohydrate, Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids (Macronutrients). Washington, DC: Natl. Acad. Press 2005
2. Amelio I, Cutruzzola F, Antonov A, AgostiniM,MelinoG. 2014. Serine and glycinemetabolism in cancer. Trends Biochem. Sci. 39:191-98
3. Anderson DD, Stover PJ. 2009. SHMT1 and SHMT2 are functionally redundant in nuclear de novo thymidylate biosynthesis. PLOS ONE 4:e5839
4. Anderson DD, Woeller CF, Chiang EP, Shane B, Stover PJ. 2012. Serine hydroxymethyltransferase anchors de novo thymidylate synthesis pathway to nuclear lamina for DNA synthesis. J. Biol. Chem. 287:7051-62
5. Aronson PS. 2006. Essential roles of CFEX-mediated Cl(-)-oxalate exchange in proximal tubule NaCl transport and prevention of urolithiasis. Kidney Int. 70:1207-13
6. Bach SJ. 1955. The metabolism of monocarbon compounds in the mammal with special reference to formic acid. Ergeb. Physiol. 48:529-74
7. Barlowe CK, ApplingDR. 1988. In vitro evidence for the involvement ofmitochondrial folatemetabolism in the supply of cytoplasmic one-carbon units. Biofactors 1:171-76
8. BrosnanME, MacMillan L, Stevens JR, Brosnan JT. 2015. Division of labour:How does folatemetabolism partition between one-carbon metabolism and amino acid oxidation? Biochem. J. 472:135-46
9. Calabrese EJ, Canada AT. 1989. Catalase: its role in xenobiotic detoxification. Pharmacol. Ther. 44:297-307
10. Cetin I, Fennessey PV, Sparks JW, Meschia G, Battaglia FC. 1992. Fetal serine fluxes across fetal liver, hindlimb, and placenta in late gestation. Am. J. Physiol. 263:E786-93
11. Cetin I,Marconi AM, Bozzetti P, Sereni LP, Corbetta C, et al. 1988. Umbilical amino acid concentrations in appropriate and small for gestational age infants a biochemical difference present in utero.Am. J. Obstet. Gynecol. 158:120-26
12. Chance B. 1950. On the reaction of catalase peroxides with acceptors. J. Biol. Chem. 182:649-58
13. Chew TW, Jiang X, Yan J, Wang W, Lusa AL, et al. 2011. Folate intake, MTHFR genotype, and sex modulate choline metabolism in mice. J. Nutr. 141:1475-81
14. Cook RJ, Champion KM, Giometti CS. 2001. Methanol toxicity and formate oxidation in NEUT2 mice. Arch. Biochem. Biophys. 393:192-98
15. Davis SR, Stacpoole PW, Williamson J, Kick LS, Quinlivan EP, et al. 2004. Tracer-derived total and folate-dependent homocysteine remethylation and synthesis rates in humans indicate that serine is the main one-carbon donor. Am. J. Physiol. Endocrinol. Metab. 286:E272-79
16. Deacon R, Perry J, Lumb M, Chanarin I. 1990. Formate metabolism in the cobalamin-inactivated rat. Br. J. Haematol. 74:354-59
17. Di Pietro E,WangXL,MacKenzie RE. 2004. The expression of mitochondrial methylenetetrahydrofolate dehydrogenase-cyclohydrolase supports a role in rapid cell growth. Biochim. Biophys. Acta 1674:78-84
18. Dorokhov YL, Shindyapina AV, Sheshukova EV, Komarova TV. 2015. Metabolic methanol: molecular pathways and physiological roles. Physiol. Rev. 95:603-44
19. Field MS, Kamynina E, Agunloye OC, Liebenthal RP, Lamarre SG, et al. 2014. Nuclear enrichment of folate cofactors and methylenetetrahydrofolate dehydrogenase 1 (MTHFD1) protect de novo thymidylate biosynthesis during folate deficiency. J. Biol. Chem. 289:29642-50
20. Fishman J. 1982. Biochemical mechanism of aromatization. Cancer Res. 42:3277-80s
21. Forneris F, Binda C, Vanoni MA, Mattevi A, Battaglioli E. 2005. Histone demethylation catalysed by LSD1 is a flavin-dependent oxidative process. FEBS Lett. 579:2203-7
22. Fu TF, Rife JP, Schirch V. 2001. The role of serine hydroxymethyltransferase isozymes in one-carbon metabolism in MCF-7 cells as determined by (13)C NMR. Arch. Biochem. Biophys. 393:42-50
23. Garcia-Martinez LF, Appling DR. 1993. Characterization of the folate-dependent mitochondrial oxidation of carbon 3 of serine. Biochemistry 32:4671-76
24. Green JM, MacKenzie RE, Matthews RG. 1988. Substrate flux through methylenetetrahydrofolate dehydrogenase: predicted effects of the concentration of methylenetetrahydrofolate on its partitioning into pathways leading to nucleotide biosynthesis or methionine regeneration. Biochemistry 27:8014-22
25. Greene ND, Copp AJ. 2014. Neural tube defects. Annu. Rev. Neurosci. 37:221-42
26. Gregory JF 3rd,Cuskelly GJ, Shane B, Toth JP, BaumgartnerTG, Stacpoole PW. 2000. Primed, constant infusion with [2H3]serine allows in vivo kinetic measurement of serine turnover, homocysteine remethylation, and transsulfuration processes in human one-carbon metabolism. Am. J. Clin. Nutr. 72:1535-41
27. Guenther BD, Sheppard CA, Tran P, Rozen R, Matthews RG, Ludwig ML. 1999. The structure and properties of methylenetetrahydrofolate reductase from Escherichia coli suggest how folate ameliorates human hyperhomocysteinemia. Nat. Struct. Biol. 6:359-65
28. Gustafsson Sheppard N, Jarl L, Mahadessian D, Strittmatter L, Schmidt A, et al. 2015. The folate-coupled enzyme MTHFD2 is a nuclear protein and promotes cell proliferation. Sci. Rep. 5:15029
29. Hamm S, Just G, LacosteN,Moitessier N, Szyf M, MamerO. 2008. On themechanism of demethylation of 5-methylcytosine in DNA. Bioorg. Med. Chem. Lett. 18:1046-49
30. Hefetz A, Blum MS. 1978. Biosynthesis and accumulation of formic acid in the poison gland of the carpenter ant Camponotus pennsylvanicus. Science 201:454-55
31. Hefetz A, Blum MS. 1978. Biosynthesis of formic acid by the poison glands of formicine ants. Biochim. Biophys. Acta 543:484-96
32. Jain M, Nilsson R, Sharma S, Madhusudhan N, Kitami T, et al. 2012. Metabolite profiling identifies a key role for glycine in rapid cancer cell proliferation. Science 336:1040-44
33. Jones PJ, Ausman LM, CrollDH, Feng JY, Schaefer EA, Lichtenstein AH. 1998. Validation of deuterium incorporation against sterol balance for measurement of human cholesterol biosynthesis. J. Lipid Res. 39:1111-17
34. Katre P, Joshi S, Bhat DS, Deshmukh M, Gurav N, et al. 2015. Effect of multi-nutrient insufficiency on markers of one carbon metabolism in young women: response to a methionine load. Eur. J. Clin. Nutr. doi: 10.1038/ejcn.2015.155
35. Kim D, Fiske BP, Birsoy K, Freinkman E, Kami K, et al. 2015. SHMT2 drives glioma cell survival in ischaemia but imposes a dependence on glycine clearance. Nature 520:363-67
36. Koc EC, Koc H. 2012. Regulation of mammalian mitochondrial translation by post-translational modifications. Biochim. Biophys. Acta 1819:1055-66
37. Krebs HA, Hems R. 1976. The regulation of the degradation of methionine and of the one-carbon units derived from histidine, serine and glycine. Adv. Enzyme Regul. 14:493-513
38. Krebs HA, Hems R, Tyler B. 1976. The regulation of folate and methionine metabolism. Biochem. J. 158:341-53
39. Krupenko NI, Dubard ME, Strickland KC, Moxley KM, Oleinik NV, Krupenko SA. 2010. ALDH1L2 is the mitochondrial homolog of 10-formyltetrahydrofolate dehydrogenase. J. Biol. Chem. 285:23056-63
40. Labuschagne CF, van den Broek NJ, Mackay GM, Vousden KH, Maddocks OD. 2014. Serine, but not glycine, supports one-carbon metabolism and proliferation of cancer cells. Cell Rep. 7:1248-58
41. Lamarre SG, MacMillan L, Morrow GP, Randell E, Pongnopparat T, et al. 2014. An isotope-dilution, GC-MS assay for formate and its application to human and animal metabolism. Amino Acids 46:1885-91
42. Lamarre SG,Molloy AM, Reinke SN, Sykes BD, Brosnan ME, Brosnan JT. 2012. Formate can differentiate between hyperhomocysteinemia due to impaired remethylation and impaired transsulfuration. Am. J. Physiol. Endocrinol. Metab. 302:E61-67
43. Lamarre SG, Saulnier RJ, Blier PU, Driedzic WR. 2014. A rapid and convenient method for measuring the fractional rate of protein synthesis in ectothermic animal tissues using a stable isotope tracer. Comp. Biochem. Physiol. B Biochem. Mol. Biol. 182:1-5
44. Luka Z, Moss F, Loukachevitch LV, Bornhop DJ, Wagner C. 2011. Histone demethylase LSD1 is a folate-binding protein. Biochemistry 50:4750-56
45. Luka Z, Mudd SH, Wagner C. 2009. Glycine N-methyltransferase and regulation of Sadenosylmethionine levels. J. Biol. Chem. 284:22507-11
46. Luka Z, Pakhomova S, Loukachevitch LV, Calcutt MW, Newcomer ME, Wagner C. 2014. Crystal structure of the histone lysine specific demethylase LSD1 complexed with tetrahydrofolate. Protein Sci. 23:993-98
47. Macchiarulo A, Camaioni E, Nuti R, Pellicciari R. 2009. Highlights at the gate of tryptophan catabolism a review on the mechanisms of activation and regulation of indoleamine 2,3-dioxygenase (IDO), a novel target in cancer disease. Amino Acids 37:219-29
48. Macdonald DW. 2001. The New Encyclopedia of Mammals. Oxford, UK: Oxford Univ. Press
49. MacFarlane AJ, Liu X, Perry CA, Flodby P, Allen RH, et al. 2008. Cytoplasmic serine hydroxymethyltransferase regulates the metabolic partitioning of methylenetetrahydrofolate but is not essential in mice. J. Biol. Chem. 283:25846-53
50. MacFarlane AJ, Perry CA, Girnary HH, Gao D, Allen RH, et al. 2009. Mthfd1 is an essential gene in mice and alters biomarkers of impaired one-carbon metabolism. J. Biol. Chem. 284:1533-39
51. Matthews RG. 2009. A love affair with vitamins. J. Biol. Chem. 284:26217-28
52. Momb J, Lewandowski JP, Bryant JD, Fitch R, Surman DR, et al. 2013. Deletion of Mthfd1l causes embryonic lethality and neural tube and craniofacial defects in mice. PNAS 110:549-54
53. Morris ML, Lee SC, Harper AE. 1972. Influence of differential induction of histidine catabolic enzymes on histidine degradation in vivo. J. Biol. Chem. 247:5793-804
54. MorrowGP, MacMillan L, Lamarre SG, Young SK, MacFarlane AJ, et al. 2015. In vivo kinetics of formate metabolism in folate-deficient and folate-replete rats. J. Biol. Chem. 290:2244-50
55. Mudd SH, Ebert MH, Scriver CR. 1980. Labile methyl group balances in the human: the role of sarcosine. Metabolism 29:707-20
56. Narisawa A, Komatsuzaki S, Kikuchi A, Niihori T, Aoki Y, et al. 2012. Mutations in genes encoding the glycine cleavage system predispose to neural tube defects in mice and humans. Hum. Mol. Genet. 21:1496-503
57. Narkewicz MR, Moores RR Jr, Battaglia FC, Frerman FF. 1999. Ontogeny of serine hydroxymethyltransferase isoenzymes in fetal sheep liver, kidney, and placenta. Mol. Genet. Metab. 68:473-80
58. Pai YJ, Leung KY, Savery D, Hutchin T, Prunty H, et al. 2015. Glycine decarboxylase deficiency causes neural tube defects and features of non-ketotic hyperglycinemia in mice. Nat. Commun. 6:6388
59. Pangilinan F, Molloy AM, Mills JL, Troendle JF, Parle-McDermott A, et al. 2014. Replication and exploratory analysis of 24 candidate risk polymorphisms for neural tube defects. BMC Med. Genet. 15:102
60. Parle-McDermott A, Pangilinan F, O'Brien KK, Mills JL, Magee AM, et al. 2009. A common variant in MTHFD1L is associated with neural tube defects and mRNA splicing efficiency. Hum. Mutat. 30:1650-56
61. Pfeiffer CM, SternbergMR, Fazili Z, Lacher DA, ZhangM, et al. 2015. Folate status and concentrations of serum folate forms in the US population: National Health and Nutrition Examination Survey 2011-2. Br. J. Nutr. 113:1965-77
62. Pike ST, Rajendra R, Artzt K, Appling DR. 2010. Mitochondrial C1-tetrahydrofolate synthase (MTHFD1L) supports the flow of mitochondrial one-carbon units into the methyl cycle in embryos. J. Biol. Chem. 285:4612-20
63. Porter DH, Cook RJ, Wagner C. 1985. Enzymatic properties of dimethylglycine dehydrogenase and sarcosine dehydrogenase from rat liver. Arch. Biochem. Biophys. 243:396-407
64. Possemato R, Marks KM, Shaul YD, Pacold ME, Kim D, et al. 2011. Functional genomics reveal that the serine synthesis pathway is essential in breast cancer. Nature 476:346-50
65. Prasannan P, Pike S, Peng K, Shane B, Appling DR. 2003. Human mitochondrial C1-tetrahydrofolate synthase: gene structure, tissue distribution of the mRNA, and immunolocalization in Chinese hamster ovary calls. J. Biol. Chem. 278:43178-87
66. Regnault TR, de Vrijer B, Battaglia FC. 2002. Transport and metabolism of amino acids in placenta. Endocrine 19:23-41
67. Sen K, Hackett JC. 2010. Peroxo-iron mediated deformylation in sterol 14alpha-demethylase catalysis. J. Am. Chem. Soc. 132:10293-305
68. Siu MT, Wiley MJ, Wells PG. 2013. Methanol teratogenicity in mutant mice with deficient catalase activity and transgenic mice expressing human catalase. Reprod. Toxicol. 36:33-39
69. Strickland KC, Krupenko NI, Dubard ME, Hu CJ, Tsybovsky Y, Krupenko SA. 2011. Enzymatic properties of ALDH1L2, a mitochondrial 10-formyltetrahydrofolate dehydrogenase. Chem. Biol. Interact. 191:129-36
70. Tamura Y, Ogihara T, Uchida T, Ikeda F, Kumashiro N, et al. 2007. Amelioration of glucose tolerance by hepatic inhibition of nuclear factor κB in db/db mice. Diabetologia 50:131-14
71. Tibbetts AS, Appling DR. 2010. Compartmentalization of mammalian folate-mediated one-carbon metabolism. Annu. Rev. Nutr. 30:57-81
72. van den Brink DM, Wanders RJ. 2006. Phytanic acid: production from phytol, its breakdown and role in human disease. Cell. Mol. Life Sci. 63:1752-65
73. Wanders RJ, Komen JC. 2007. Peroxisomes, Refsum's disease and the alpha-and omega-oxidation of phytanic acid. Biochem. Soc. Trans. 35:865-69
74. Wang H, Wang L, Zhang H, Deng P, Chen J, et al. 2013. 1H NMR-based metabolic profiling of human rectal cancer tissue. Mol. Cancer 12:121
75. Wang L, Chen J, Chen L, Deng P, Bu Q, et al. 2013. 1H-NMR based metabonomic profiling of human esophageal cancer tissue. Mol. Cancer 12:25
76. Wang Y, Huang Y,Wang J, Cheng C, HuangW, et al. 2009. Structure of the formate transporter FocA reveals a pentameric aquaporin-like channel. Nature 462:467-72
77. Washburn SE, Caudill MA, Malysheva O, MacFarlane AJ, Behan NA, et al. 2015. Formate metabolism in fetal and neonatal sheep. Am. J. Physiol. Endocrinol. Metab. 308:E921-27
78. Waydhas C,Weigl K, Sies H. 1978. The disposition of formaldehyde and formate arising from drug Ndemethylations dependent on cytochrome P-450 in hepatocytes and in perfused rat liver. Eur. J. Biochem. 89:143-50
79. Wittwer AJ, Wagner C. 1981. Identification of the folate-binding proteins of rat liver mitochondria as dimethylglycine dehydrogenase and sarcosine dehydrogenase. Flavoprotein nature and enzymatic properties of the purified proteins. J. Biol. Chem. 256:4109-15
80. Woeller CF, Anderson DD, Szebenyi DM, Stover PJ. 2007. Evidence for small ubiquitin-like modifierdependent nuclear import of the thymidylate biosynthesis pathway. J. Biol. Chem. 282:17623-31
81. Wray J. 1670. Extract of a Letter, Written by Mr. John Wray to the Publisher January 13. 1670. Concerning some un-common observations and experiments made with an acid juyce to be found in ants. Philos. Trans. 5:2063-66
82. Yoshida T, Kikuchi G. 1973. Major pathways of serine and glycine catabolism in various organs of the rat and cock. J. Biochem. 73:1013-22