Chemistry:Lac-Phe

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Lactoylphenylalanine, or Lac-Phe, is an N-lactoyl-amino acid metabolite produced by mammals and microorganisms.[1][2][3][4][5] In humans, levels are increased by intense exercise and in the inborn error of metabolism phenylketonuria.[6][7][8][1][9] In mice, high levels of Lac-Phe in the blood cause a decrease of food intake[6] and in humans, its production has been shown to correlate with adipose tissue loss during an endurance exercise intervention.[10] In mammals it is created from (S)-lactate and L-phenylalanine by the cytosol nonspecific dipeptidase (CNDP2) protein.[1] It is classified as N-acyl-alpha-amino acid and pseudodipeptide.[11]

It has also been reported that as an additive, N-L-lactoyl phenylalanine improves the taste of food, conferring an umami flavor.[12] It is found naturally in significant amounts in some traditional Chinese fermented foods such as preserved pickles and soy sauce,[13] and in Parmigiano-Reggiano cheese.[14] Oral intake of Lac-Phe does not have anti-obesity effects in mice, though intraperitoneal injection does reduce food intake and weight gain.[6] Activity dependent cell labeling indicates Lac-Phe activated neural populations in the hypothalamus and brainstem. [15]

See also

References

  1. ↑ 1.0 1.1 1.2 "N-lactoyl-amino acids are ubiquitous metabolites that originate from CNDP2-mediated reverse proteolysis of lactate and amino acids". Proceedings of the National Academy of Sciences of the United States of America 112 (21): 6601–6606. May 2015. doi:10.1073/pnas.1424638112. PMID 25964343. Bibcode: 2015PNAS..112.6601J. 
  2. ↑ Sgarbi, Elisa; Lazzi, Camilla; Iacopino, Luca; Bottesini, Chiara; Lambertini, Francesca; Sforza, Stefano; Gatti, Monica (2013-09-01). "Microbial origin of non proteolytic aminoacyl derivatives in long ripened cheeses". Food Microbiology 35 (2): 116–120. doi:10.1016/j.fm.2013.02.013. ISSN 0740-0020. PMID 23664262. https://www.sciencedirect.com/science/article/abs/pii/S0740002013000373. 
  3. ↑ Bottesini, Chiara; Tedeschi, Tullia; Dossena, Arnaldo; Sforza, Stefano (2014-02-01). "Enzymatic production and degradation of cheese-derived non-proteolytic aminoacyl derivatives" (in en). Amino Acids 46 (2): 441–447. doi:10.1007/s00726-013-1637-3. ISSN 1438-2199. PMID 24337832. https://link.springer.com/article/10.1007/s00726-013-1637-3. 
  4. ↑ Feng, Junwei; Huang, Zikun; Huang, Mingtao; Cui, Chun; Zhao, Mouming; Feng, Yunzi (2024-11-30). "Revealing the Microbial Origins of N-Lactoyl Amino Acids in Soy Sauce: Synthesis Conditions, Potential Enzymes, and Utilization Preference". Journal of Agricultural and Food Chemistry 73 (5): 3008–3015. doi:10.1021/acs.jafc.4c04907. ISSN 0021-8561. PMID 39614824. https://pubs.acs.org/doi/10.1021/acs.jafc.4c04907. 
  5. ↑ Xiao, Shuke; Li, Veronica L.; Long, Jonathan Z. (2024-08-01). "Lac-Phe (N-lactoyl-phenylalanine)" (in English). Trends in Endocrinology & Metabolism 35 (8): 758–759. doi:10.1016/j.tem.2024.05.007. ISSN 1043-2760. PMID 39137723. 
  6. ↑ 6.0 6.1 6.2 "An exercise-inducible metabolite that suppresses feeding and obesity". Nature 606 (7915): 785–790. June 2022. doi:10.1038/s41586-022-04828-5. PMID 35705806. Bibcode: 2022Natur.606..785L. 
  7. ↑ "Appetite-suppressing molecule helps obese mice lose weight". New Scientist. 15 June 2022. https://www.newscientist.com/article/2324591-appetite-suppressing-molecule-helps-obese-mice-lose-weight/. 
  8. ↑ "Why Does a Hard Workout Make You Less Hungry?". The New York Times. 15 June 2022. https://www.nytimes.com/2022/06/15/well/move/exercise-appetite.html. 
  9. ↑ Václavík, Jan; Coene, Karlien L. M.; Vrobel, Ivo; Najdekr, Lukáš; Friedecký, David; Karlíková, Radana; Mádrová, Lucie; Petsalo, Aleksanteri et al. (2018). "Structural elucidation of novel biomarkers of known metabolic disorders based on multistage fragmentation mass spectra" (in en). Journal of Inherited Metabolic Disease 41 (3): 407–414. doi:10.1007/s10545-017-0109-4. ISSN 1573-2665. PMID 29139026. https://onlinelibrary.wiley.com/doi/10.1007/s10545-017-0109-4. 
  10. ↑ "Exercise-Induced N-Lactoylphenylalanine Predicts Adipose Tissue Loss during Endurance Training in Overweight and Obese Humans". Metabolites 13 (1): 15. January 2023. doi:10.3390/metabo13010015. PMID 36676940. 
  11. ↑ "Metabocard for N-Lactoylphenylalanine". The Human Metabolome Database (HMDB). The Metabolomics Innovation Centre (TIMC). https://hmdb.ca/metabolites/HMDB0062175. 
  12. ↑ Feng, Junwei; Huang, Zikun; Cui, Chun; Zhao, Mouming; Feng, Yunzi (2024-10-01). "Synthesis, taste characteristics and taste mechanism of N-lactoyl leucine from soy sauce using sensory analysis and UPLC-MS/MS". Food Chemistry 454. doi:10.1016/j.foodchem.2024.139670. ISSN 0308-8146. PMID 38820630. https://www.sciencedirect.com/science/article/abs/pii/S0308814624013207. 
  13. ↑ "Preparation and Taste Characteristics of Kokumi N-Lactoyl Phenylalanine in the Presence of Phenylalanine and Lactate". Journal of Agricultural and Food Chemistry 70 (17): 5396–5407. May 2022. doi:10.1021/acs.jafc.2c00530. PMID 35452224. Bibcode: 2022JAFC...70.5396W. 
  14. ↑ Sforza, Stefano; Cavatorta, Valeria; Galaverna, Gianni; Dossena, Arnaldo; Marchelli, Rosangela (2009-10-01). "Accumulation of non-proteolytic aminoacyl derivatives in Parmigiano-Reggiano cheese during ripening". International Dairy Journal 19 (10): 582–587. doi:10.1016/j.idairyj.2009.04.009. ISSN 0958-6946. https://linkinghub.elsevier.com/retrieve/pii/S0958694609000776. 
  15. ↑ Moya-Garzon MD, Wang M, Li VL, Lyu X, Wei W, Tung AS (2024). "A β-hydroxybutyrate shunt pathway generates anti-obesity ketone metabolites.". Cell 188 (1): 175–186.e20. doi:10.1016/j.cell.2024.10.032. PMID 39536746. 



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