Occurrence, stability, and determination of formyl folates in foods

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 41, 2013, Pages 9758-9768

  Jägerstad, Margaretha ^a   Jastrebova, Jelena ^a  

^a SWEDISH UNIVERSITY OF AGRICULTURAL SCIENCES   (Sweden)

Author keywords

analysis; formyl folates; HPLC; interconversions; LC MS; stability

Indexed keywords

ANALYSIS; FOLATES; HPLC; INTERCONVERSIONS; LC-MS;

ALKYLATION; AMINO ACIDS; CONVERGENCE OF NUMERICAL METHODS; LAKES; NUCLEIC ACIDS; REPAIR;

FOOD PROCESSING;

FOLINIC ACID; VITAMIN B COMPLEX;

CHEMISTRY; FOOD ANALYSIS; FOOD HANDLING; OXIDATION REDUCTION REACTION; REVIEW;

FOOD ANALYSIS; FOOD HANDLING; FORMYLTETRAHYDROFOLATES; OXIDATION-REDUCTION; VITAMIN B COMPLEX;

EID: 84886935876     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf4028427     Document Type: Review

References (87)

1. Hawkes, J. G.; Villota, R. Folates in foods: reactivity, stability during processing, and nutritional implications Crit. Rev. Food Sci. Nutr. 1989, 28, 439-538
2. MRC Vitamin Study Research Group. Prevention of neural tube defects; results of the Medical Research Council Vitamin Study Lancet 1991, 338, 131-137
3. Selhub, J.; Rosenberg, I. H. Folic acid. In Present Knowledge in Nutrition, 7 th ed.; Ziegler, E. E.; Filer, L. J., Eds.; ILSI Press: Washington, DC, 1996; pp 206-219.
4. Lucock, M. Folic acid: nutritional biochemistry, molecular biology, and role in disease processes Mol. Gen. Metab. 2000, 1, 121-138
5. Durga, J.; van Boxtel, M. P.; Schouten, E. G.; Kok, F. J.; Jolles, J.; Katan, M. B.; Verhoef, P. Effect of 3 year folic acid supplementation on cognitive function in older adults in the FACIT trial: a randomised, double-blind, controlled trial Lancet 2007, 369, 208-216
6. WCRF/AICR (World Cancer Research Fund/American Institute for Cancer Research Publisher). Food, Nutrition, Physical Activity and the Prevention of Cancer: A Global Perspective; Washington, DC, 2007; www.dietandcancerreport.org (accessed March 2013).
7. Kim, Y.-I. Folic acid supplementation and cancer risk: Point. Cancer Epidemiol., Biomarkers Prev. 2008, 17, updated version downloaded Feb 19, 2012, from www.cebp.aacrjournals.org.
8. Cole, B. F.; Baron, J. A.; Sandler, R. S.; Haile, R. W.; Ahmen, D. J.; Bresalier, R. S.; McKeown-Eyssen, G.; Summers, R. W. Folic acid for the prevention of colorectal adenomas: a randomized clinical trial JAMA, J. Am. Med. Assoc. 2007, 297, 2351-2359
9. Wien, T. N.; Pike, E.; Wisloff, T.; Staff, A.; Smeland, S.; Klemp, M. Cancer risk with folic acid supplements: a systematic review and meta-analysis BMJ Open 2012, 2e000653 10.1136/bmjopen-2011-005
10. Bouckaert, K. P.; Slimani, N.; Nicolas, G.; Vignat, J.; Wright, A. J. A.; Roe, M.; Witthöft, C. M.; Finglas, P. Critical evaluation of folate data in European and international databases. Recommendations for standardization in nutritional studies Mol. Nutr. Food Res. 2011, 55, 166-180
11. Gregory, J. F. Chemical and nutritional aspects of folate research: analytical procedures, methods of folate synthesis, stability, and bioavailability of dietary folates. In Advances in Food and Nutrition Research; Kinsella, J. E., Ed.; Academic Press: New York, 1989; pp 1-101.
12. Ye, L.; Eitenmiller, R. R.; Ye, L.; Landen, W. O. Chapter 10. Folate and folic acid. In Vitamin Analysis for the Health and Food Sciences, 2 nd ed.; CRC Press: Boca Raton, FL, 2007; pp 443-505.
13. Blakley, R. L. The biochemistry of folic acid and related pteridines. In Frontiers of Biology. North Holland Publishing: Amsterdam, The Netherlands, 1969; pp 1-99.
14. Robinson, D. R. The nonenzymatic hydrolysis of N5,N10- methenyltetrahydrofolic acid and related reactions Methods Enzymol. 18B 1971, 184, 716-725
15. Quinlivan, E. P.; Hanson, A. D.; Gregory, J. F. The analysis of folate and its metabolic precursors in biological samples Anal. Biochem. 2006, 348, 163-184
16. Scott, J.; Rebeille, F.; Fletcher, J. Folic acid and folates: the feasibility for nutritional enhancement in plant foods J. Sci. Food Agric. 2000, 80, 795-824
17. Duthie, S. J. Folate and cancer: how DNA damage, repair and methylation impact on colon carcinogens J. Inher. Metab. Dis. 2011, 34, 101-109
18. van der Put, N. M. J.; van Straaten, H. W. M.; Trijbels, F. J. M.; Blom, H. J. Folate, homocysteine and neural tube defects: an overview Exp. Biol. Med. 2001, 226, 243-270
19. Refsum, H.; Ueland, P. M.; NygaÌŠrd, O.; Vollset, S. E. Homocysteine and cardiovascular disease Annu. Rev. Med. 1998, 49, 31-62
20. USDA National Nutrient Database for Standard Reference, release 25; Nutrient Data Laboratory Home Page, 2012; http://www.ars.usda.gov/ba/bhnrc/ndl.
21. Ossey, E. S.; Wehling, R. L.; Albrecht, J. A. HPLC determination of stability and distribution of added folic acid and some endogenous folates during breadmaking Cereal Chem. 2001, 78, 375-378
22. Piironen, V.; Edelmann, M.; Kariluoto, S.; Bedo, Z. Folate in wheat genotypes in the HEALTHGRAIN diversity screen J. Agric. Food Chem. 2008, 56, 9726-9731
23. Patring, J.; Wandel, M.; Jägerstad, M.; Fröhlich, W. Folate content in Norwegian and Swedish flours and bread analysed by use of liquid chromatography mass spectrometry J. Food Compos. Anal. 2009, 22, 649-656
24. Müller, H. Determination of folic acid content of grain, cereal products, bakery products and legumes by means of high-performance liquid chromatography (HPLC) Z. Lebensm. Unters. Forsch. 1993, 197, 573-577
25. Pfeiffer, C. M.; Rogers, L. M.; Gregory, J. F. Determination of folate in cereal-grain food products using trienzyme extraction and combined affinity and reversed-phase liquid chromatography J. Agric. Food Chem. 1997, 45, 407-413
26. Konings, E. J. M.; Roomans, H. H. S.; Dorant, E.; Goldbohm, R. A.; Saris, W. H. M.; van den Brandt, P. A. Folate intake of the Dutch population according to newly established liquid chromatography data for foods Am. J. Clin. Nutr. 2001, 73, 765-776
27. Freisleben, A.; Schieberle, P.; Rychlik, M. Comparison of folate quantification in foods by high-performance liquid chromatography-fluorescence detection to that by stable isotope dilution assays using high-performance liquid chromatography-tandem mass spectrometry Anal. Biochem. 2003, 315, 247-255
28. Kariluoto, S.; Vahteristo, L.; Salovaara, H.; Katina, K.; Liukkonen, K. H.; Piironen, V. Effect of baking method and fermentation on folate content of rye and wheat breads Cereal Chem. 2004, 81, 134-139
29. Ringling, C.; Rychlik, M. Analysis of seven folates in food by LC-MS/MS to improve accuracy of total folate data Eur. Food Res. Technol. 2013, 236, 17-28
30. Seyoum, E.; Selhub, J. Properties of food folates determined by stability and susceptibility to intestinal pteroylpolyglutamate hydrolase action J. Nutr. 1998, 128, 1956-1960
31. Patring, J.; Jastrebova, J.; Hjortmo, S.; Andlid, T.; Jägerstad, M. Development of a simplified method for the determination of folates in baker's yeast by HPLC with ultraviolet and fluorescence detection J. Agric. Food Chem. 2005, 53, 2606-2411
32. Patring, J.; Jastrebova, J. Application of liquid chromatography- electrospray ionisation mass spectrometry for determination of dietary folates: effects of buffer nature and mobile phase composition on sensitivity and selectivity J. Chromatogr., A 2007, 1143, 72-82
33. Jastrebova, J.; Strandler, H. S.; Patring, J.; Wiklund, T. Comparison of UPLC and HPLC for analysis of dietary folates Chromatographia 2011, 73, 219-225
34. Müller, H. Determination of folic acid contents in vegetables and fruits by means of high-performance liquid chromatography (HPLC) Z. Lebensm. Unters. Forsch. 1993, 196, 137-141
35. Vahteristo, L.; Lehikoinen, K.; Ollilainen, V.; Varo, P. Application of an HPLC assay for the determination of folate derivatives in some vegetables, fruits and berries consumed in Finland Food Chem. 1997, 59, 589-597
36. Rychlik, M.; Netzel, M.; Pfannebecker, I.; Frank, T.; Bitsch, I. Application of stable isotope dilution assays based on liquid chromatography-tandem mass spectrometry for the assessment of folate bioavailability J. Chromatogr., B 2003, 792, 167-176
37. Zhang, G. F.; Storozhenko, S.; Van Der Straeten, D.; Lambert, W. E. Investigation of the extraction behavior of the main monoglutamate folates from spinach by liquid chromatography-electrospray ionization tandem mass spectrometry J. Chromatogr., A 2005, 1078, 59-66
38. Shohag, M. J. I.; Wei, Y.-Y.; Yu, N.; Zangh, J.; Wang, K.; Patring, J.; He, Z.; Yang, X. Natural variation of folate content and composition in spinach (Spinacia oleracea) germplasm J. Agric. Food Chem. 2011, 59, 12520-12526
39. Vahteristo, L. T.; Ollilainen, V.; Varo, P. Liquid chromatographic determination of folate monoglutamates in fish, meat, egg, and dairy products consumed in Finland J. AOAC Int. 1997, 80, 373-378
40. Strandler, H. S. Determination of Folate for Food Composition Data; Lic. thesis, Swedish University of Agricultural Sciences, Uppsala, Sweden, 2012; pp 35.
41. Müller, H. Determination of folic acid contents in foods of animal origin by means of high-performance liquid chromatography (HPLC) Z. Lebensm. Unters. Forsch. 1993, 196, 518-521
42. Vishnumohan, S.; Arcot, J.; Pickford, R. Naturally-occurring folates in foods: Method development and analysis using liquid chromatography tandem mass spectrometry (LC-MS/MS) Food Chem. 2011, 125, 736-742
43. FFI (Flour Fortification Initiative); http://www.FFInetwork.org/global- progress/index.php (accessed Aug 29, 2013).
44. Stover, P. J. One-carbon metabolism-genome interaction in folate-associated pathologies J. Nutr. 2009, 139, 2402-2405
45. Stover, P. J.; Field, M. S. Trafficking of intracellular folates Adv. Nutr. 2011, 2, 325-331
46. Girgis, S.; Suh, J. R.; Jolivet, J.; Stover, J. 5-Fomyltetrahydrofolate regulates homocysteine remethylation in human neuroblastoma J. Biol. Chem. 1997, 272, 4729-4734
47. Stover, P.; Schirch, V. The metabolic role of leucovorin Trends Biochem. Sci. (TIBS) 1993, 18, 102-106
48. Baggott, J. E.; Tamura, T. Bioactivity of orally administered unnatural isomers, [6 R ]-5-formyltetrahydrofolate and [6 S ]-5,10- methenyltetrahydrofolate in humans Biochim. Biophys. Acta 1999, 1472, 323-332
49. Baggott, J. E.; Tamura, T. Metabolism of 10-formyldihydrofolate in humans Biomed. Pharmacother. 2001, 55, 454-457
50. May, M.; Bardos, T. J.; Barger, F. L.; Lansford, M.; Ravel, J. M. Synthetic and degradative investigations of the structure of folinic acid-SF J. Am. Chem. Soc. 1951, 73, 3067-3075
51. Cosulich, D. B.; Roth, B.; Smith, J. B.; Hultquist, M. E.; Parker, R. P. Acid transformation products of leucovorin J. Am. Chem. Soc. 1951, 73, 5006 (letter to the Editor)
52. Cosulich, D. B.; Roth, B.; Smith, J. B.; Hultquist, M. E.; Parker, R. P. Chemistry of leucovorin J. Am. Chem. Soc. 1952, 74, 3252-3263
53. Stokstad, E. L. R.; Koch, J. Folic acid metabolism Physiol. Rev. 1967, 47, 83-115
54. Robinson, D. R.; Jencks, J. P. Mechanism and catalysis of the hydrolysis of methenyltetrahydrofolic acid J. Am. Chem. Soc. 1967, 89, 7098-7103
55. 10-formyltetrahydrofolic acid J. Biol. Chem. 1960, 235, 195-201
56. Jastrebova, J.; Axelsson, M.; Strandler, H. S.; Jägerstad, M. Stability of dietary 5-formyltetrahydrofolate and its determination by HPLC: a pilot study on impact of pH, temperature and antioxidants on analytical results Eur. Food Res. Technol. 2013, 10.1007/s00217-013-2046-2
57. Baggott, J. E. Hydrolysis of 5,10-methenyltetrahydrofolate to 5-formyltetrahydrofolate at pH 2.5 to 4.5 Biochemistry 2000, 39, 14647-14653
58. Tabor, H.; Wyngarden, L. The enzymatic formation of formiminotetrahydrofolic acid, 5,10-methenyltetrahydrofolic acid and 10-formyltetrahydrofolic acid in the metabolism of formiminoglutamic acid J. Biol. Chem. 1959, 235, 1830-1846
59. Beavon, J. R. G.; Blair, J. A. The pH dependent rearrangements of formyltetrahydrofolates and their nutritional implications Br. J. Nutr. 1972, 28, 385-390
60. Stover, P.; Schirch, V. Serine hydroxymethyltransferase catalyzes the hydrolysis of 5,10-methenyltetrahydrofolate to 5-formyltetrahydrofolate J. Biol. Chem. 1990, 265, 14227-14233
61. Stover, P.; Schirch, V. Enzymatic mechanism for the hydrolysis of 5,10 methenyltetrahydropteroylglutamate to 5-formyltetrahydrofolate by serinehydroxymethyltransferase Biochemistry 1992, 31, 2155-2164
62. Gregory, J. F. Chapter 7. Vitamins. In Fennema's Food Chemistry, 4 th ed.; Damodaran, S.; Parkin, K. L.; Fennema, O. R., Eds.; CRC Press: Boca Raton, FL, 2008; pp 498-503.
63. Ball, G. F. M. Chapter 13. Folate. In Vitamins in Foods. Analysis, Bioavailability, And Stability; Ball, G., Ed.; CRC Press: Boca Raton, FL, 2006; pp 231-273.
64. Tyagi, A.; Penzkofer, A.; Batschauer, A.; Wolf, E. Thermal degradation of (6 R, S)-5,10-methenyltetrahydrofolate in aqeous solution at pH 8 Chem. Phys. 2009, 358, 132-136
65. De Brouwer, V.; Zhang, G.-F.; Storozhenko, S.; van der Straeten, D.; Lambert, W. pH stability of individual folates during critical sample preparation steps in prevision of the analysis of plant folates Phytochem. Anal. 2007, 18, 496-508
66. Jägerstad, M.; Piironen, V.; Walker, C.; Carnovale, E.; Holasova, M.; Nau, H.; Ros, G. Increasing natural-food folates through bioprocessing and biotechnology Trends Food Sci. Technol. 2005, 16, 298-306
67. AOAC Official Method 992.05. Folic acid (pteroylglutamic acid) in infant formula. In Official Methods of Analysis, 17 th ed.; Horwitz, W., Ed.; AOAC International: Gaithersburg, MD, 2000; pp 50.024-50.026.
68. AOAC Official Method 2004.05. Total folates in cereals and cereal foods. In Official Methods of Analysis, 10 th ed.; AOAC International: Gaithersburg, MD, 2004.
69. Kariluoto, M. S.; Vahteristo, L. T.; Piironen, V. I. Applicability of microbiological assay and affinity chromatography purification followed by high-performance liquid chromatography (HPLC) in studying folate contents in rye J. Sci. Food Agric. 2001, 81, 938-942
70. Selhub, J. Determination of tissue folate composition by affinity chromatography followed by high-pressure ion pair liquid chromatography Anal. Biochem. 1989, 182, 84-93
71. Nygren-Babol, L.; Jägerstad, M. Folate-binding protein in milk: a review of biochemistry, physiology and analytical methods Crit. Rev. Food Sci. Nutr. 2012, 52, 410-425
72. Nilsson, C.; Johansson, M.; Yazynina, E.; Stralsjo, L.; Jastrebova, J. Solid-phase extraction for HPLC analysis of dietary folates Eur. Food Res. Technol. 2004, 219, 199-204
73. Ruggeri, S.; Vahteristo, L.; Aguzzi, A.; Finglas, P. M.; Carnovale, E. Determination of folate vitamers in food and in Italian reference diet by high-performance liquid chromatography J. Chromatogr., A 1999, 855, 237-245
74. Ginting, E.; Arcot, J. High-performance liquid chromatographic determination of naturally occuring folates during tempe preparation J. Agric. Food Chem. 2004, 52, 7752-7758
75. Kirsch, S.; Knapp, J.-P.; Herrmann, W.; Obeid, R. Quantification of key folate forms in serum using stable-isotope dilution ultra performance liquid chromatography-tandem mass spectrometry J. Chromatogr., B 2010, 878, 68-75
76. Pfeiffer, C. M.; Fazili, Z.; McCoy, L.; Zhang, M.; Gunter, E. W. Determination of folate vitamers in human serum by stable-isotope-dilution tandem mass spectrometry and comparison with radioassay and microbiologic assay Clin. Chem. 2004, 50, 423-432
77. Liu, J.; Pickford, R.; Meagher, A. P.; Ward, R. L. Quantitative analysis of tissue folate using ultra-high-performance liquid chromatography tandem mass spectrometry Anal. Biochem. 2011, 411, 210-217
78. Huang, Y.; Kartulyari, S.; Morales, M. E.; Stanislawska-Sachadyn, A.; von Feldt, J. M.; Whitehead, A.; Blair, I. A. A. Quantification of key red blood cell folates from subjects with defined MTHFR 677C>T genotypes using stable isotope dilution liquid chromatography/mass spectrometry Rapid Commun. Mass Spectrom. 2008, 22, 2403-2412
79. Diaz de la Garza, R.; Quinlivan, E. P.; Klaus, S. M.; Basset, G. J. C.; Gregory, J. F., III; Hanson, A. D. Folate biofortification in tomatoes by engineering the pteridine branch of folate synthesis Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 13720-13725
80. Diaz de la Garza, R. I.; Gregory, J. F., III; Hanson, A. D. Folate biofortification of tomato fruit Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 4218-4222
81. De Brouwer, V.; Storozhenko, S.; Van de Steene, J. C.; Wille, S.; Stove, C. P.; van der Straeten, D.; Lambert, W. E. Optimisation and validation of a liquid chromatography-tandem mass spectrometry method for folates in rice J. Chromatogr., A 2008, 1215, 125-132
82. De Brouwer, V.; Storozhenko, S.; Stove, C. P.; Van Daele, J.; Van der Straeten, D.; Lambert, W. E. Ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) for the sensitive determination of folates in rice J. Chromatogr., B: Anal. Tech. Biomed. Life Sci. 2010, 878, 509-513
83. Büttner, B. E.; Öhrvik, V. E.; Witthöft, C. M.; Rychlik, M. Quantification of isotope-labelled and unlabelled folates in plasma, ileostomy and food samples Anal. Bioanal. Chem. 2011, 399, 429-439
84. Phillips, K. M.; Wunderlich, K. M.; Holden, J. M.; Exler, J.; Gebhardt, S. E.; Haytowitz, D. B.; Beecher, G. R.; Doherty, R. F. Stability of 5-methyltetrahydrofolate in frozen fresh fruits and vegetables Food Chem. 2005, 92, 587-595
85. Phillips, K. M.; Ruggio, D. M.; Ashraf-Khorassani, M.; Haytowitz, D. B. Difference in folate content of green and red sweet peppers (Capsicum annuum) determined by liquid chromatography-mass spectrometry J. Agric. Food Chem. 2006, 54, 9998-10002
86. Phillips, K. M.; Ruggio, D. M.; Haytowitz, D. Folate composition of 10 types of mushrooms determined by liquid chromatography-mass spectrometry Food Chem. 2011, 129, 630-636
87. Bagley, P. J.; Selhub, J. Analysis of folate form distribution by affinity followed by reversed-phase chromatography with electrochemical detection Clin. Chem. 2000, 46, 404-411