Glucuronolactone

Glucuronolactone is a molecule commonly found as a component of Energy Drinks formulations with surprisingly minimal research on it, given its societal usage.

This page features 17 unique references to scientific papers.


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Also Known As

Glucuronic Acid, Glucaro 1,4-lactone, Glutarate


Table of Contents:


Edit1. Sources and Stucture

1.1. Structure

Glucuronolactone is a molecule that is commonly found in energy drinks (at around 10-60mg, with variance depending on brand), although in studies 'disassembling' the constituents of energy drinks suggest no significant contribution towards energy.[1][2]

1.2. Biological Significance

In vitro, D-glucuronolactone can be metabolized by a dehydrogenase into D-Glucaro-1,4-Lactone (G14L), where D-glucuronolactone appears to metabolize into a dilactone (d-glucaro-1,4-3,6-dilactone) and then spontaneously degrade into G14L.[3]

D-Glucaric acid is the main urinary metabolite of the glucuronic acid pathway,[4][5] which synthesizes Glucuronic Acid for the purposes of conjugation by drug metabolizing enzymes (UGT transferases). Daily urine output of D-Glucaric Acid is approximately 30-100umol.[6][7]

Glucuronolactone is a prodrug for the compound D-Glucaro-1,4-Lactone

In animals (non-primapes) that are capable of synthesizing ascorbic acid (Vitamin C) endogenously, glucuronolactone is used as a pre-requisite for ascorbic acid.[8]

Can be used to synthesize Vitamin C in creatures capable of this conversion, which are not humans

1.3. Enzymatic Interactions

D-Glucaro-1,4-Lactone (G14L) appears to be an inhibitor of the β-Glucuronidase enzyme.[3]


Edit2. Pharmacology

2.1. Metabolism

Glucuronolactone can be formed when glucuronic acid is degraded in subcritical water interchangeably.[9]


Edit3. Cardiovascular Health

3.1. Blood Flow

1,4-GL can be seen as protective for blood vessel health by alleviating oxidative/nitrative damage to lipoproteins from reactive species such as hydroperoxide and peroxynitrate, as well as acting as an anti-platelet aggregative compound.[10][11] It may be synergistic with Resveratrol in this regard.[12]

When consuming an energy drink (80mg Caffeine, 1000mg Taurine, 800mg Glucuronolactone; sugar free with B-complex), an overall increase in platelet aggregation appears to occur in otherwise healthy persons with infrequent energy drink consumption.[13] Participants refrained from caffeine for a week prior to testing, and the contribution of Glucuronolactone towards the observed effects was not established.[13]


Edit4. Skeletal Muscle and Performance

4.1. Aerobic Exercise

One study injecting glucuronolactone (100mg/kg) intraperitoneally in rats immediately prior to a 30 minute swim and subsequent rest (the swim which was repeated three times, each with an injection prior to the swim) noted that glucuronolactone failed to affect time to exhaustion in the first swim but improved performance relative to saline in the second and third swim.[14]


Edit5. Interactions with Cancer

Via its actions as a beta-glucuronidase inhibitor (of which too much activity is correlated with some forms of cancer), 1,4-GL can be seen as potentially anti-carcinogenic.[15] 1,4-GL and D-Glutarate also have potent anti-proliferative properties.[16]

References

  1. Mets MA, et al. Positive effects of Red Bull® Energy Drink on driving performance during prolonged driving. Psychopharmacology (Berl). (2011)
  2. Debunking the Effects of Taurine in Red Bull Energy Drink
  3. Marsh CA. Metabolism of D-glucuronolactone in mammalian systems. Inhibitory properties of the products of D-glucuronolactone-dehydrogenase action. Biochem J. (1966)
  4. Perry W, Jenkins MV. Note on the enzyme assay for urinary D-glucaric acid and correlation with rifampicin-induced mixed function oxidase activity. Int J Clin Pharmacol Ther Toxicol. (1986)
  5. Metabolism of d-glucuronolactone in mammalian systems. Identification of d-glucaric acid as a normal constituent of urine
  6. Marsh CA. An enzymatic determination of D-glucaric acid by conversion to pyruvate. Anal Biochem. (1985)
  7. Marsh CA. Biosynthesis of D-glucaric acid in mammals: a free-radical mechanism. Carbohydr Res. (1986)
  8. Smirnoff N. L-ascorbic acid biosynthesis. Vitam Horm. (2001)
  9. Wang R, et al. Degradation kinetics of glucuronic acid in subcritical water. Biosci Biotechnol Biochem. (2010)
  10. Saluk-Juszczak J, et al. Protective effects of D-glucaro-1,4-lactone against oxidative modifications in blood platelets. Nutr Metab Cardiovasc Dis. (2008)
  11. Olas B, et al. Protective effects of D-glucaro 1,4-lactone against oxidative/nitrative modifications of plasma proteins. Nutrition. (2007)
  12. Olas B, Saluk-Juszczak J, Wachowicz B. D-glucaro 1,4-lactone and resveratrol as antioxidants in blood platelets. Cell Biol Toxicol. (2008)
  13. Worthley MI, et al. Detrimental effects of energy drink consumption on platelet and endothelial function. Am J Med. (2010)
  14. Tamura S, et al. Effects of glucuronolactone and the other carbohydrates on the biochemical changes produced in the living body of rats by hard exercise. Jpn J Pharmacol. (1968)
  15. [No authors listed. Calcium-D-glucarate. Altern Med Rev. (2002)
  16. Walaszek Z. Potential use of D-glucaric acid derivatives in cancer prevention. Cancer Lett. (1990)
  17. Wilson CP1, et al. Riboflavin offers a targeted strategy for managing hypertension in patients with the MTHFR 677TT genotype: a 4-y follow-up. Am J Clin Nutr. (2012)

(Common misspellings for Glucuronolactone include glutrate, glucaronic, glucuronlactone, glucuro)

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