Challenges in the determination of unsubstituted food folates: Impact of stabilities and conversions on analytical results

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 9, 2015, Pages 2367-2377

  Strandler, Hanna Sara ^a   Patring, Johan ^b   Jägerstad, Margaretha ^b   Jastrebova, Jelena ^b  

^a National Food Agency   (Sweden)

^b SWEDISH UNIVERSITY OF AGRICULTURAL SCIENCES   (Sweden)

Author keywords

5,10 methylenetetrahydrofolate; dihydrofolate; folate oxidation; folate stabilization; folic acid; tetrahydrofolate

Indexed keywords

DEVELOPING COUNTRIES;

5,10-METHYLENETETRAHYDROFOLATE; ANALYTICAL PROCEDURE; ANALYTICAL RESULTS; CARBON METABOLISM; DIHYDROFOLATE; FOLIC ACIDS; OXIDATION MECHANISMS; TETRAHYDROFOLATES;

ORGANIC ACIDS;

FOLIC ACID;

ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; FOOD ANALYSIS; HUMAN; METABOLISM; OXIDATION REDUCTION REACTION;

ANIMALS; FOLIC ACID; FOOD ANALYSIS; HUMANS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 84924565867     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf504987n     Document Type: Review

References (91)

1. MRC Vitamin Study Research Group. Prevention of neural tube defects: results of the Medical Research Council Vitamin Study Lancet 1991, 338, 131-137
2. Lucock, M. Folic acid: nutritional biochemistry, molecular biology, and role in disease processes Mol. Gen. Metab. 2000, 71, 121-138
3. Clarke, R.; Halsey, J.; Bennett, D.; Lewington, S. Homocysteine and vascular disease: review of published results of the homocysteine-lowering trials J. Inherit. Metab. Dis. 2011, 34, 83-91
4. De-Regil, L.; Fernández-Gaxiola, A.; Dowswell, T.; Peña-Rosas, J. Effects and safety of periconceptional folate supplementation for preventing birth defects. Cochrane Database Systematic Rev. 2010, 10, CD007950.
5. 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, USA; www.dietandcancerreport.org (accessed March 2014).
6. Durga, J.; van Boxtel, M. P. J.; 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
7. Qin, X.; Cui, Y.; Shen, L.; Sun, N.; Zhang, Y.; Li, J.; Xu, X.; Wang, B.; Xu, X.; Huo, Y.; Wang, X. Folic acid supplementation and cancer risk: a meta-analysis of randomized controlled trials Int. J. Cancer 2013, 133, 1033-1041
8. Wien, T. N.; Pike, E.; Wisløff, T.; Staff, A.; Smeland, S.; Klemp, M. Cancer risk with folic acid supplements: a systematic review and meta-analysis. BMJ Open 2012, 2e000653, DOI: 10.1136/bmjopen-2011-005.
9. 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.
10. Nelson, D. L.; Cox, M. M. Chapter 22.2. Biosynthesis of amino acids. In Lehninger Principles of Biochemistry, 5 th ed.; Freeman: New York, 2008; pp 882-897.
11. Hawkes, J. G.; Villota, R. Folates in foods: reactivity, stability during processing, and nutritional implications Crit. Rev. Food Sci. Nutr. 1989, 28, 439-538
12. Ball, G. F. M. Folate. In Vitamins in Foods: Analysis, Bioavailability, and Stability; Ball, G., Ed.; CRC Press: Boca Raton, FL, USA, 2006; pp 231-273.
13. Kirsch, S. H.; 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
14. Wilson, S. D.; Horne, D. W. Evaluation of ascorbic acid in protecting labile folic acid derivatives Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 6500-6504
15. Reed, L. S.; Archer, M. C. Oxidation of tetrahydrofolic acid by air J. Agric. Food Chem. 1980, 28, 801-805
16. Eto, I.; Krumdieck, C. L. Determination of three different pools of reduced one-carbon-substituted folates: I. A study of the fundamental chemical reactions Anal. Biochem. 1980, 109, 167-184
17. USDA National Nutrient Database for Standard Reference, release 25; Nutrient Data Laboratory Home Page, 2012; http://www.ars.usda.gov/ba/bhnrc/ndl.
18. 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
19. Ravanel, S.; Douce, R.; Rébeille, F. Metabolism of folates in plants. In Advances in Botanical Research; Rebeille, F.; Douce, R., Eds.; Academic Press: London, UK, 2011; Vol. 59, pp 67-106.
20. Hanson, A. D.; Gregory, J. F. Folate biosynthesis, turnover, and transport in plants Annu. Rev. Plant Biol. 2011, 62, 105-125
21. Díaz 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
22. De Brouwer, V.; Storozhenko, S.; Van de Steene, J. C.; Wille, S. M. R.; 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
23. Jägerstad, M.; Piironen, V.; Walker, C.; Ros, G.; Carnovale, E.; Holasova, M.; Nau, H. Increasing natural food folates through bioprocessing and biotechnology Trends Food Sci.Technol. 2005, 16, 298-306
24. Koehler, P.; Hartmann, G.; Wieser, H.; Rychlik, M. Changes of folates, dietary fiber, and proteins in wheat as affected by germination J. Agric. Food Chem. 2007, 55, 4678-4683
25. Patring, J.; Wandel, M.; Jägerstad, M.; Frølich, W. Folate content of Norwegian and Swedish flours and bread analysed by use of liquid chromatography-mass spectrometry J. Food Compos. Anal. 2009, 22, 649-656
26. Kariluoto, S.; Edelmann, M.; Herranen, M.; Lampi, A.-M.; Shmelev, A.; Salovaara, H.; Korhola, M.; Piironen, V. Production of folate by bacteria isolated from oat bran Int. J. Food Microbiol. 2010, 143, 41-47
27. FFI (Food Fortification Initiative); http://www.ffinetwork.org (accessed January 2015).
28. Patring, J. D. M.; Jastrebova, J. A. 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
29. 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
30. 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
31. Freisleben, A.; Schieberle, P.; Rychlik, M. Specific and sensitive quantification of folate vitamers in foods by stable isotope dilution assays using high-performance liquid chromatography-tandem mass spectrometry Anal. Bioanal. Chem. 2003, 376, 149-156
32. 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
33. Wang, C.; Riedl, K. M.; Schwartz, S. J. Fate of folates during vegetable juice processing - deglutamylation and interconversion Food Res. Int. 2013, 53, 440-448
34. 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 2010, 878, 509-513
35. 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.
36. Temple, C., Jr.; Montgomery, J. A. Chemical and physical properties of folic acid and reduced derivatives. In Folates and Pterins; Blakley, R. L.; Benkovic, S. J., Eds.; Wiley: New York, 1984; Vol. 1, pp 62-104.
37. Patring, J.; Lanina, S. A.; Jastrebova, J. A. Applicability of alkyl-bonded ultra-pure silica stationary phases for gradient reversed-phase HPLC of folates with conventional and volatile buffers under highly aqeous conditions J. Sep. Sci. 2006, 29, 889-904
38. Kallen, R. G.; Jencks, W. P. The dissociation constants of tetrahydrofolic acid J. Biol. Chem. 1966, 241, 5845-5850
39. Kallen, R. Tetrahydrofolic acid and formaldehyde. In Methods in Enzymology; Wright, D. M. A. L., Ed.; Academic Press: New York, 1971; Vol. 66, pp 705-716.
40. Poe, M. Acidic dissociation constants of folic acid, dihydrofolic acid, and methotrexate J. Biol. Chem. 1977, 25, 3724-3728
41. Gregory, J. F. Vitamins. In Food Chemistry; Damodaran, S.; Parkin, K. L.; Fennema, O. R., Eds.; Dekker: New York, 2008; pp 498-503.
42. OBroin, J.; Temperley, I.; Brown, J.; Scott, J. Nutritional stability of various naturally occurring monoglutamate derivatives of folic acid Am. J. Clin. Nutr. 1975, 28, 438-444
43. Paine-Wilson, B.; Chen, T. S. Thermal destruction of folacin: effect of pH and buffer ions J. Food Sci. 1979, 44, 717-722
44. Mnkeni, A. P.; Beveridge, T. Thermal destruction of pteroylglutamic acid in buffer and model food systems J. Food Sci. 1982, 47, 2038-2041
45. Lowry, O. H.; Bessey, O. A.; Crawford, E. J. Photolytic and enzymatic transformations of pteroylglutamic acid J. Biol. Chem. 1949, 180, 389-398
46. Akhtar, M. J.; Khan, M. A.; Ahmad, I. Photodegradation of folic acid in aqueous solution J. Pharm. Biomed. Anal. 1999, 19, 269-275
47. Akhtar, J. M.; Khan, A. M.; Ahmad, I. Effect of riboflavin on the photolysis of folic acid in aqueous solution J. Pharm. Biomed. Anal. 2000, 23, 1039-1044
48. Thomas, A. H.; Suárez, G.; Cabrerizo, F. M.; Martino, R.; Capparelli, A. L. Study of the photolysis of folic acid and 6-formylpterin in acid aqueous solutions J. Photochem. Photobiol. A: Chem. 2000, 135, 147-154
49. Poe, M. Dihydrofolate reductase from a methotrexate-resistant strain of Escherichia coli: dihydrofolate monooxygenase activity Biochem. Biophys. Res. Commun. 1973, 54, 1008-1014
50. Hillcoat, B. L.; Nixon, P. F.; Blakley, R. L. Effect of substrate decomposition on the spectrophotometric assay of dihydrofolate reductase Anal. Biochem. 1967, 21, 178-189
51. Scrimgeour, K. G. Methods for reduction, stabilization, and analyses of folates. In Methods in Enzymology; Donald, B.; McCormick, L. D. W., Eds.; Academic Press: New York, 1980; Vol. 66, pp 517-523.
52. Chen, T. S.; Cooper, R. G. Thermal destruction of folacin: effect of ascorbic acid, oxygen and temperature J. Food Sci. 1979, 44, 713-716
53. Tripet, F. Y.; Kesselring, U. W. Stability of solid folic acid in relation to temperature and humidity Pharm. Acta Helv. 1975, 50, 318-322
54. Blair, J. A.; Pearson, A. J. Kinetics and mechanism of the autoxidation of the 2-amino-4-hydroxy-5,6,7,8-tetrahydropteridines J. Chem. Soc., Perkin Trans. 2 1974, 1, 80-88
55. Blair, J. A.; Farrar, G. Chapter 6. Oxidation of tetrahydrofolates and tetrahydrobiopterin by molecular oxygen. In Atmospheric Oxidation and Antioxidants; Scott, G., Ed.; Elsevier: Amsterdam, The Netherlands, 1993; pp 171-182.
56. Martin, C. B.; Walker, D.; Soniat, M. Density functional theory study of possible mechanisms of folic acid photodecomposition J. Photochem. Photobiol. A: Chem. 2009, 208, 1-6
57. Wilson, S. D.; Horne, D. W. High-performance liquid chromatographic determination of the distribution of naturally occurring folic acid derivatives in rat liver Anal. Biochem. 1984, 142, 529-535
58. Osborn, M. J.; Huennekens, F. M. Enzymatic reduction of dihydrofolic acid J. Biol. Chem. 1958, 233, 969-974
59. Blakley, R. L. Spectrophotometric studies on the combination of formaldehyde with tetrahydropteroylglutamic acid and other hydropteridines Biochem. J. 1960, 74, 71-82
60. Patring, J. D. M.; Johansson, M.; Yazynina, E.; Jastrebova, J. Evaluation of impact of different antioxidants on stability of dietary folates during food sample preparation and storage of extracts prior to analysis Anal. Chim. Acta 2005, 553, 36-42
61. De Brouwer, V.; Zhang, G. F.; Storozhenko, S.; Straeten, D. V.; Lambert, W. E. pH stability of individual folates during critical sample preparation steps in prevision of the analysis of plant folates Phytochem. Anal. 2007, 18, 496-508
62. Zakrezewski, S. F. Evidence for the chemical interaction between 2-mercaptoethanol and tetrahydrofolate J. Biol. Chem. 1966, 241, 2957-2961
63. Pearson, A. J. Kinetics and mechanisms of the autooxidation of tetrahydropterins Chem. Ind. 1974, 233-239
64. 10-methylene tetrahydrofolic acid) J. Am. Chem. Soc. 1960, 82, 4921-4927
65. Blakley, R. L. The reaction of tetrahydropteroylglutamic acid and related hydropteridines with formaldehyde Biochem. J. 1959, 72, 707-710
66. Kallen, R. G.; Jencks, W. P. The mechanism of the condensation of formaldehyde with tetrahydrofolic acid J. Biol. Chem. 1966, 241, 5851-5863
67. Jones, M. L.; Nixon, P. F. Tetrahydrofolates are greatly stabilized by binding to bovine milk folate-binding protein J. Nutr. 2002, 132, 2690-2694
68. 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
69. Konings, E. J.; Roomans, H. H.; Dorant, E.; Goldbohm, R. A.; Saris, W. H.; 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
70. Stea, T. H.; Johansson, M.; Jägerstad, M.; Frølich, W. Retention of folates in cooked, stored and reheated peas, broccoli and potatoes for use in modern large-scale service systems Food Chem. 2007, 101, 1095-1107
71. Delchier, N.; Ringling, C.; Le Grandois, J.; Aoudé-Werner, D.; Galland, R.; Georgé, S.; Rychlik, M.; Renard, C. Effects of industrial processing on folate content in green vegetables Food Chem. 2013, 139, 815-824
72. Nollet, L. M. L.; Toldra, F. Food Analysis by HPLC, 3rd ed.; CRC Press: Boca Raton, FL, USA, 2012.
73. Official Methods of Analysis of AOAC INTERNATIONAL (2003) 17th Ed., AOAC INTERNATIONAL: Gaithersburg, MD, USA, Official Method 992.05.
74. Official Methods of Analysis of AOAC INTERNATIONAL (2005) 18th Ed., AOAC INTERNATIONAL: Gaithersburg, MD, USA. Official Method 2004.05.
75. CEN, EN 14131:2003 Foodstuffs. Determination of folate by microbiological assay, 2003.
76. Boström Caselunghe, M.; Lindeberg, J. Biosensor-based determination of folic acid in fortified food Food Chem. 2000, 70, 523-532
77. Stralsjo, L.; Arkbage, K.; Witthoft, C.; Jagerstad, M. Evaluation of a radioprotein-binding assay (RPBA) for folate analysis in berries and milk Food Chem. 2002, 79, 525-534
78. 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
79. Strandler, H. S. Determination of Folate for Food Composition Data, Swedish University of Agricultural Sciences, Uppsala, Sweden, 2012.
80. 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, USA, 2008; pp 443-505.
81. Bagley, P. J.; Selhub, J. Analysis of folate form distribution by affinity followed by reversed-phase chromatography and electrochemical detection Clin. Chem. 2000, 46, 404-411
82. Jägerstad, M.; Jastrebova, J. Occurrence, stability, and determination of formyl folates in foods J. Agric. Food Chem. 2013, 61, 9758-9768
83. van den Berg, H.; Finglas, P. M.; Bates, C. FLAIR intercomparisons on serum and red cell folate Int. J. Vitam. Nutr. Res. 1994, 64, 288-293
84. Yazynina, E.; Johansson, M.; Jagerstad, M.; Jastrebova, J. Low folate content in gluten-free cereal products and their main ingredients Food Chem. 2008, 111, 236-242
85. Tamura, T.; Shin, Y. S.; Williams, M. A.; Stokstad, E. L. R. Lactobacillus casei response to pteroylpolyglutamates Anal. Biochem. 1972, 49, 517-521
86. Ramos-Parra, P. A.; Urrea-Lopez, R.; Diaz de la Garza, R. I. Folate analysis in complex food matrices: use of a recombinant Arabidopsis γ-glutamyl hydrolase for folate deglutamylation Food Res. Int. 2013, 54, 177-185
87. Tamura, T.; Mizuno, Y.; Johnston, K. E.; Jacob, R. A. Food folate assay with protease, α-amylase, and folate conjugase treatments J. Agric. Food Chem. 1997, 45, 135-139
88. van Daele, J.; Blancquaert, D.; Kiekens, F.; van Der Straeten, D.; Lambert, W. E.; Stove, C. P. Folate profiling in potato (Solanum tuberosum) tubers by ultrahigh-performance liquid chromatography-tandem mass spectrometry J. Agric. Food Chem. 2014, 62, 3092-3100
89. Strandler, H. S.; Axelsson, M.; Jastrebova, J. Food folate analysis by HPLC; effects of on-column degradation and interconversion of folates. Presented at the 1st International Vitamin Conference, Copenhagen, Denmark, 2010.
90. Gounelle, J. C.; Ladjimi, H.; Prognon, P. A rapid ans specific extraction procedure for folate determination in rat liver and analysis by high-performance liquid chromatography with fluorometric detection Anal. Biochem. 1989, 176, 406-411
91. Wieling, J. LC-MS-MS experiences with internal standards Chromatographia 2002, 55, S107-S113