Nicotinamide riboside

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Structural formula
Structural formula
General
Surname Nicotinamide riboside
other names
  • 1- (β-D-ribofuranosyl) nicotinamide
  • N-ribosyl nicotinamide
Molecular formula C 11 H 15 N 2 O 5 +
External identifiers / databases
CAS number 1341-23-7
PubChem 439924
ChemSpider 388956
Wikidata Q3334152
properties
Molar mass 255.25 g mol −1
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nicotinamidribosid ( NO ) is a chemical compound selected from the group pyridine - nucleosides , presumably a precursor of vitamin B 3 ( nicotinamide adenine dinucleotide , or NAD + is).

properties

Nicotinamide riboside (NR) was first described as a growth factor ( Factor V ) by Haemophilus influenzae in 1944 . Factor V purified from the blood has been described as consisting of three substances: NAD +, NMN and NR. NR accelerated the growth of H. influena the most. H. influenza , on the other hand, does not grow in culture media with nicotinic acid , nicotinamide , tryptophan or aspartic acid , which were previously described as precursors of NAD +.

In 2000 it was shown for Sir2 from yeast that Sir2 is an NAD + -dependent protein - lysine - deacetylase . The biosynthesis of NAD + in yeast was probably carried out exclusively via NAMN (nicotinic acid mononucleotide). If the glutamine- hydrolyzing NAD + synthase is deleted in yeast , yeast can still grow in the presence of NR. The conversion of NR to NMN by nicotinamide riboside kinases was then demonstrated in vitro and in vivo .

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ↑ Bogan, KL, Brenner, C .: Nicotinic acid, nicotinamide, and nicotinamide riboside: a molecular evaluation of NAD + precursor vitamins in human nutrition . In: Annu. Rev. Nutr. . 28, 2008, pp. 115-130. doi : 10.1146 / annurev.nutr.28.061807.155443 . PMID 18429699 .
  3. ↑ Chi Y, Sauve AA: Nicotinamide riboside, a trace nutrient in foods, is a vitamin B3 with effects on energy metabolism and neuroprotection . In: Curr Opin Clin Nutr Metab Care . 16, No. 6, November 2013, pp. 657-61. doi : 10.1097 / MCO.0b013e32836510c0 . PMID 24071780 .
  4. ^ W Gingrich, F Schlenk: Codehydrogenase I and Other Pyridinium Compounds as V-Factor for Hemophilus influenzae and H. parainfluenzae. . In: Journal of Bacteriology . 47, No. 6, June 1944, pp. 535-50. PMID 16560803 . PMC 373952 (free full text).
  5. ↑ Belenky, P .: NAD + Metabolism in Health and Disease . In: Trends in Biochemical Sciences . 32, No. 1, 2007, pp. 12-19. doi : 10.1016 / j.tibs.2006.11.006 . PMID 17161604 .
  6. ↑ Imai, S .: Transcriptional silencing and longevity protein Sir2 is an NAD-dependent histone deacetylase . In: Nature . 403, No. 6771, 2000, pp. 795-800. doi : 10.1038 / 35001622 . PMID 10693811 .
  7. ↑ Anderson: Nicotinamide and PNC1 govern lifespan extension by calorie restriction in Saccharomyces cerevisiae . In: Nature . 423, No. 6936, 2003, pp. 181-185. doi : 10.1038 / nature01578 . PMID 12736687 . PMC 4802858 (free full text).
  8. ↑ Bitterman: Inhibition of silencing and accelerated aging by nicotinamide, a putative negative regulator of yeast Sir2 and human SIRT1 . In: J. Biol. Chem. . 277, No. 47, 2002, pp. 45099-45107. doi : 10.1074 / jbc.m205670200 . PMID 12297502 .
  9. ↑ Gallo: Nicotinamide clearance by pnc1 directly regulates sir2-mediated silencing and longevity . In: Mol. Cell. Biol . 24, No. 3, 2004, pp. 1301-1312. doi : 10.1128 / mcb.24.3.1301-1312.2004 . PMC 321434 (free full text).
  10. ↑ Panozzo, C .: Aerobic and anaerobic NAD + metabolism in Saccharomyces cerevisiae . In: FEBS Lett. . 517, No. 1-3, 2002, pp. 97-102. doi : 10.1016 / s0014-5793 (02) 02585-1 . PMID 12062417 .
  11. ↑ JJ Sandmeier, I Celic, JD Boeke, JS Smith: Telomeric and rDNA silencing in Saccharomyces cerevisiae are dependent on a nuclear NAD (+) salvage pathway. . In: Genetics . 160, No. 3, March 2002, pp. 877-89. PMID 11901108 . PMC 1462005 (free full text).
  12. ↑ P. Bieganowski, C. Brenner: Discoveries of nicotinamide riboside as a nutrient and conserved NRK genes establish a Preiss-Handler independent route to NAD + in fungi and humans. In: Cell . Volume 117, Number 4, May 2004, pp. 495-502, doi: 10.1016 / s0092-8674 (04) 00416-7 , PMID 15137942 .
  13. ↑ Hautkooper, RH: Sirtuins as regulators of metabolism and healthspan . In: Nat. Rev. Mol. Cell Biol . 13, No. 4, 2012, pp. 225-238. doi : 10.1038 / nrm3293 . PMID 22395773 . PMC 4872805 (free full text).