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Chemical Compound Review

Pyridoxic acid     3-hydroxy-5-(hydroxymethyl)- 2-methyl...

Synonyms: P9630_ALDRICH, SureCN195230, AG-H-31277, CHEBI:17405, P9630_SIGMA, ...
 
 
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Disease relevance of Pyridoxic acid

 

High impact information on Pyridoxic acid

  • The values of Vmax/Km and pKm were highest for PLP and 4-pyridoxic acid phosphate and lowest for pyridoxamine phosphate [6].
  • At its optimal pH of 8.0-8.6, it catalyzes the oxidation of isopyridoxal (Km = 40 microM, turnover number = 10 s-1 molecule-1) by NAD+ (Km = 40 microM) to a mixture of 5-pyridoxic acid and 5-pyridoxolactone, which are produced in constant ratio throughout the course of the reaction [7].
  • Reaction b also is enhanced when the poorly utilized analogues, 3-hydroxy-2-methylpyridine-5-carboxylic acid or NADH, replace 5-pyridoxic acid or NADPH, respectively, as substrates in Reaction a [8].
  • This was reflected in the decreased production of 4-pyridoxic acid by the perfused liver from 3.8% to 1.2% of the dose by the addition of erythrocytes to the perfusate [9].
  • However, in membrane fractions, oxygen supports 4-pyridoxic acid oxidation via a CN--sensitive electron transport chain, indicating that the dehydrogenase probably is coupled to ATP generation in such preparations [1].
 

Chemical compound and disease context of Pyridoxic acid

 

Biological context of Pyridoxic acid

  • The change in isotope abundance of urinary 4-pyridoxic acid following administration of [2H2]PN reflects the kinetics of labelling of the body pools of vitamin B6, and yields, non-invasively, the rate of degradation of glycogen phosphorylase [11].
  • To evaluate PN-glucoside bioavailability, the subjects were administered a single oral dose of either deuterium-labeled ([2H2]) PN (Trial 1) or [2H2] PN-glucoside (Trial 2), and the urinary excretion rates of labeled 4-pyridoxic acid (4PA) were measured [12].
  • The urinary 4-pyridoxic acid excretion of the DR groups responded to the reduced food intake and were lower at weeks 10 and 20 [13].
 

Anatomical context of Pyridoxic acid

 

Associations of Pyridoxic acid with other chemical compounds

 

Gene context of Pyridoxic acid

  • PLP, pyridoxal (PL) and 4-pyridoxic acid (4-PA) were the major B6 compounds in plasma and the only compounds which increased after supplementation [21].
  • Depending on the indicator, between 20% and 70% of the subjects had inadequate values for 4-pyridoxic acid, total vitamin B-6, plasma pyridoxal 5'-phosphate, and erythrocyte alanine aminotransferase percentage stimulation at a vitamin B-6 intake of 1.33 mg/d (0.016 mg vitamin B-6/g protein) [22].
  • RESULTS: Renal clearance of 4-pyridoxic acid was 232 +/- 94 mL/min in nonpregnant women, 337 +/- 140 mL/min in pregnant women, and 215 +/- 103 mL/min in lactating healthy women [2].
  • The dietary vitamin B-6 to protein ratio of both diets was 0.017 mg/g. Urinary excretions of 4-pyridoxic acid and total vitamin B-6 were significantly lower (P < 0.05) during the high PNG diet period than when the low PNG diet was consumed [23].
  • This compound, named tetrahydropentoxyline, is a new type of hydrophilic tetrahydro-beta-carboline, and its elution position was between those of 4-pyridoxic acid and kynurenic acid on C18 reversed-phase HPLC [24].
 

Analytical, diagnostic and therapeutic context of Pyridoxic acid

References

  1. The bacterial oxidation of vitamin B6. 4-Pyridoxic acid dehydrogenase: a membrane-bound enzyme from Pseudomonas MA-1. Yagi, T., Kishore, G.M., Snell, E.E. J. Biol. Chem. (1983) [Pubmed]
  2. Elevated plasma 4-pyridoxic acid in renal insufficiency. Coburn, S.P., Reynolds, R.D., Mahuren, J.D., Schaltenbrand, W.E., Wang, Y., Ericson, K.L., Whyte, M.P., Zubovic, Y.M., Ziegler, P.J., Costill, D.L., Fink, W.J., Pearson, D.R., Pauly, T.A., Thampy, K.G., Wortsman, J. Am. J. Clin. Nutr. (2002) [Pubmed]
  3. Vitamin B6 deficiency in cancer patients. Potera, C., Rose, D.P., Brown, R.R. Am. J. Clin. Nutr. (1977) [Pubmed]
  4. Feeding experiments of pyridoxine derivatives as vitamin B6. Maeno, M., Morimoto, Y., Hayakawa, T., Suzuki, Y., Tsuge, H. International journal for vitamin and nutrition research. Internationale Zeitschrift für Vitamin- und Ernährungsforschung. Journal international de vitaminologie et de nutrition. (1997) [Pubmed]
  5. Excretion of 4-pyridoxic acid and oxalic acid in patients with urinary calculi. Tiselius, H.G. Investigative urology. (1977) [Pubmed]
  6. Kinetic analysis and chemical modification of vitamin B6 phosphatase from human erythrocytes. Gao, G.J., Fonda, M.L. J. Biol. Chem. (1994) [Pubmed]
  7. Enzymes of vitamin B6 degradation. Purification and properties of isopyridoxal dehydrogenase and 5-formyl-3-hydroxy-2-methylpyridine-4-carboxylic-acid dehydrogenase. Lee, Y.C., Nelson, M.J., Snell, E.E. J. Biol. Chem. (1986) [Pubmed]
  8. Enzymes of vitamin B6 degradation. Purification and properties of 5-pyridoxic-acid oxygenase from Arthrobacter sp. Nelson, M.J., Snell, E.E. J. Biol. Chem. (1986) [Pubmed]
  9. Effect of binding to hemoglobin and albumin on pyridoxal transport and metabolism. Ink, S.L., Henderson, L.M. J. Biol. Chem. (1984) [Pubmed]
  10. Use of chlorite to improve HPLC detection of pyridoxal 5'-phosphate. Ericson, K.L., Mahuren, J.D., Zubovic, Y.M., Coburn, S.P. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. (2005) [Pubmed]
  11. Measurement of the turnover of glycogen phosphorylase by GC/MS using stable isotope derivatives of pyridoxine (vitamin B6). Beynon, R.J., Leyland, D.M., Evershed, R.P., Edwards, R.H., Coburn, S.P. Biochem. J. (1996) [Pubmed]
  12. Pyridoxine-5'-beta--glucoside exhibits incomplete bioavailability as a source of vitamin B-6 and partially inhibits the utilization of co-ingested pyridoxine in humans. Nakano, H., McMahon, L.G., Gregory, J.F. J. Nutr. (1997) [Pubmed]
  13. The influence of dietary restriction on vitamin B-6 vitamer distribution and on vitamin B-6 metabolizing enzymes in rats. Wei, I.L. Journal of the American College of Nutrition. (1999) [Pubmed]
  14. Induction of sister-chromatid exchange in human lymphocytes by vitamin B6. Dozi-Vassiliades, J., Mourelatos, D., Myrtsiotis, A. Mutat. Res. (1983) [Pubmed]
  15. The utilization of intravenously infused pyridoxine in humans. Zempleni, J., Kübler, W. Clin. Chim. Acta (1994) [Pubmed]
  16. Vitamin B6 deficiency in chronic liver disease--evidence for increased degradation of pyridoxal-5'-phosphate. Labadarios, D., Rossouw, J.E., McConnell, J.B., Davis, M., Williams, R. Gut (1977) [Pubmed]
  17. Dietary intake of total and glycosylated vitamin B-6 and the vitamin B-6 nutritional status of unsupplemented lactating women and their infants. Andon, M.B., Reynolds, R.D., Moser-Veillon, P.B., Howard, M.P. Am. J. Clin. Nutr. (1989) [Pubmed]
  18. Effect of high dose ascorbic acid on vitamin B6 metabolism. Shultz, T.D., Leklem, J.E. Am. J. Clin. Nutr. (1982) [Pubmed]
  19. Chronic exercise affects vitamin B-6 metabolism but not requirement of growing rats. Hadj-Saad, F., Lhuissier, M., Guilland, J.C. J. Nutr. (1997) [Pubmed]
  20. The status of plasma homocysteine and related B-vitamins in healthy young vegetarians and nonvegetarians. Huang, Y.C., Chang, S.J., Chiu, Y.T., Chang, H.H., Cheng, C.H. European journal of nutrition. (2003) [Pubmed]
  21. The measurement of plasma vitamin B6 compounds: comparison of a cation-exchange HPLC method with the open-column chromatographic method and the L-tyrosine apodecarboxylase assay. Lui, A., Lumeng, L., Li, T.K. Am. J. Clin. Nutr. (1985) [Pubmed]
  22. Changes in vitamin B-6 status indicators of women fed a constant protein diet with varying levels of vitamin B-6. Hansen, C.M., Leklem, J.E., Miller, L.T. Am. J. Clin. Nutr. (1997) [Pubmed]
  23. Vitamin B-6 status indicators decrease in women consuming a diet high in pyridoxine glucoside. Hansen, C.M., Leklem, J.E., Miller, L.T. J. Nutr. (1996) [Pubmed]
  24. A hydrophilic tetrahydro-beta-carboline in human urine. Horiuchi, K., Yonekawa, O., Iwahara, K., Kanno, T., Kurihara, T., Fujise, Y. J. Biochem. (1994) [Pubmed]
  25. Determination of urinary 4-pyridoxic acid using high performance liquid chromatography. Gregory, J.F., Kirk, J.R. Am. J. Clin. Nutr. (1979) [Pubmed]
  26. Pyridoxic acid excretion during low vitamin B-6 intake, total fasting, and bed rest. Coburn, S.P., Thampy, K.G., Lane, H.W., Conn, P.S., Ziegler, P.J., Costill, D.L., Mahuren, J.D., Fink, W.J., Pearson, D.R., Schaltenbrand, W.E. Am. J. Clin. Nutr. (1995) [Pubmed]
  27. A simple liquid-chromatographic method for measuring vitamin B6 compounds in plasma. Edwards, P., Liu, P.K., Rose, G.A. Clin. Chem. (1989) [Pubmed]
 
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