Oxidation of 10-formyltetrahydrofolate to 10-formyldihydrofolate by complex IV of rat mitochondria

Biochemistry. 2002 Apr 30;41(17):5633-6. doi: 10.1021/bi0120244.

Abstract

We hypothesized that the unanticipated bioactivity of orally administered unnatural carbon-6 isomers, (6R)-5-formyltetrahydrofolate (5-HCO-THF) and (6S)-5,10-methenyltetrahydrofolate (5,10-CH-THF), in humans [Baggott, J. E., and Tamura, T. (1999) Biochim. Biophys. Acta 1472, 323-32] is explained by the rapid oxidation of (6S)-10-formyltetrahydrofolate (10-HCO-THF), which is produced by in vivo chemical processes from the above folates. An oxidation of 10-HCO-THF produces 10-formyldihydrofolate (10-HCO-DHF), which no longer has the asymmetric center at carbon-6 and is metabolized by aminoimidazole carboxamide ribotide (AICAR) transformylase forming bioactive dihydrofolate. Since cytochrome c (Fe(3+)) rapidly oxidizes both (6R)- and (6S)-10-HCO-THF [Baggott et al. (2001) Biochem. J. 354, 115-22], we investigated the metabolism of 10-HCO-THF by isolated rat liver mitochondria. We found that 10-HCO-THF supported the respiration of mitochondria without uncoupling ATP synthesis. The site of electron donation was identified as complex IV, which contains cytochrome c; the folate product was 10-HCO-DHF, and the reaction was saturable with respect to 10-HCO-THF. Both (6S)- (unnatural) and (6R)-10-HCO-THF supported the respiration of mitochondria, whereas (6S)-5-formyltetrahydrofolate (5-HCO-THF) was inactive. To our knowledge, this cytochrome c oxidation of 10-HCO-THF to 10-HCO-DHF in the mitochondrial intermembrane space represents a possible folate metabolic pathway previously unidentified and would explain the bioactivity of unnatural carbon-6 isomers, (6R)-5-HCO-THF and (6S)-5,10-CH-THF, in humans.

MeSH terms

  • Animals
  • Antimycin A / pharmacology
  • Dose-Response Relationship, Drug
  • Electron Transport / drug effects
  • Electron Transport Complex IV / metabolism*
  • Folic Acid / analogs & derivatives*
  • Folic Acid / metabolism*
  • Half-Life
  • Hydrolysis
  • Leucovorin / analogs & derivatives*
  • Leucovorin / antagonists & inhibitors
  • Leucovorin / metabolism*
  • Male
  • Mitochondria, Liver / drug effects
  • Mitochondria, Liver / enzymology*
  • Mitochondria, Liver / metabolism
  • Oxidants / metabolism*
  • Oxidation-Reduction
  • Oxygen Consumption / drug effects
  • Potassium Cyanide / pharmacology
  • Rats
  • Rats, Sprague-Dawley

Substances

  • Oxidants
  • 10-formyltetrahydropteroylglutamic acid
  • 10-formyldihydrofolate
  • Antimycin A
  • Folic Acid
  • Electron Transport Complex IV
  • Potassium Cyanide
  • Leucovorin