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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Gynesine     1-methylpyridine-5-carboxylate

Synonyms: Caffearin, Coffearin, Caffearine, Coffearine, Trigonellin, ...
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Disease relevance of Trigenelline

  • Genes controlling the catabolism of trigonelline, a secondary metabolite that is often present in legumes, are located on the pSym megaplasmid of Rhizobium meliloti [1].
  • Trigonelline and amino acids were heated separately or in combinations for 20 min at 250 degrees C. The results of bacteria mutation assays (Salmonella typhimurium strains TA 98, YG 1024 and YG 1029) showed that trigonelline, alone or in combination with most of the single amino acids and mixtures of amino acids, yielded potent mutagenic activity [2].
  • Staphylococcus aureus accumulated all tested betaines except trigonelline [3].
  • Other dietary betaines such as trigonelline may also be taken but enhance urea toxicity [4].
  • Niacin and trigonelline inhibited the invasion of hepatoma cells at concentrations of 2.5-40 microM without affecting proliferation [5].

High impact information on Trigenelline


Biological context of Trigenelline


Anatomical context of Trigenelline


Associations of Trigenelline with other chemical compounds


Gene context of Trigenelline

  • The time course of the absorbance change was monitored for the binding of DAO with trigonelline by means of a stopped-flow technique [10].
  • Diosgenin (1.65 mg/ml; 4 mM) inhibited glucagon-induced HGPa activity by 20% (p < 0.05), and was more effective than trigonelline (non significant inhibition of 9.4% at 1.65 mg/ml, 10 mM) [18].
  • The prevalent biotype (A8b trigonelline-) was isolated in the delivery room, in the operating room, in the Nursery and in the NICU from items, healthy infant excreters and affected infants; the second biotype (A3a) was isolated only in the NICU from staff, two healthy infant excreters and two affected infants [19].

Analytical, diagnostic and therapeutic context of Trigenelline


  1. Genetic analysis of a region of the Rhizobium meliloti pSym plasmid specifying catabolism of trigonelline, a secondary metabolite present in legumes. Boivin, C., Barran, L.R., Malpica, C.A., Rosenberg, C. J. Bacteriol. (1991) [Pubmed]
  2. Trigonelline, a naturally occurring constituent of green coffee beans behind the mutagenic activity of roasted coffee? Wu, X., Skog, K., Jägerstad, M. Mutat. Res. (1997) [Pubmed]
  3. Osmoprotective properties and accumulation of betaine analogues by Staphylococcus aureus. Peddie, B.A., Wong-She, J., Randall, K., Lever, M., Chambers, S.T. FEMS Microbiol. Lett. (1998) [Pubmed]
  4. Inhibitors of bacterial growth in urine: what is the role of betaines? Chambers, S.T., Peddie, B.A., Randall, K., Lever, M. Int. J. Antimicrob. Agents (1999) [Pubmed]
  5. Anti-invasive activity of niacin and trigonelline against cancer cells. Hirakawa, N., Okauchi, R., Miura, Y., Yagasaki, K. Biosci. Biotechnol. Biochem. (2005) [Pubmed]
  6. Inactivation of DNA replication origins by the cell cycle regulator, trigonelline, in root meristems of Lactuca sativa. Mazzuca, S., Bitonti, M.B., Innocenti, A.M., Francis, D. Planta (2000) [Pubmed]
  7. UV-B- and oxidative stress-induced increase in nicotinamide and trigonelline and inhibition of defensive metabolism induction by poly(ADP-ribose)polymerase inhibitor in plant tissue. Berglund, T., Kalbin, G., Strid, A., Rydström, J., Ohlsson, A.B. FEBS Lett. (1996) [Pubmed]
  8. Betaine use by rhizosphere bacteria: genes essential for trigonelline, stachydrine, and carnitine catabolism in Rhizobium meliloti are located on pSym in the symbiotic region. Goldmann, A., Boivin, C., Fleury, V., Message, B., Lecoeur, L., Maille, M., Tepfer, D. Mol. Plant Microbe Interact. (1991) [Pubmed]
  9. Alkylpyridiniums. 1. Formation in model systems via thermal degradation of trigonelline. Stadler, R.H., Varga, N., Hau, J., Vera, F.A., Welti, D.H. J. Agric. Food Chem. (2002) [Pubmed]
  10. Proton release from flavoprotein D-amino acid oxidase on complexation with the zwitterionic ligand, trigonelline. Nishina, Y., Sato, K., Shiga, K. J. Biochem. (1990) [Pubmed]
  11. Absorption of trigonelline from the small intestine of the specific pathogen-free (SPF) and germ-free (GF) rats in vivo. Yuyama, S. Adv. Exp. Med. Biol. (1999) [Pubmed]
  12. Trigonelline-induced neurite outgrowth in human neuroblastoma SK-N-SH cells. Tohda, C., Nakamura, N., Komatsu, K., Hattori, M. Biol. Pharm. Bull. (1999) [Pubmed]
  13. Search for natural products related to regeneration of the neuronal network. Tohda, C., Kuboyama, T., Komatsu, K. Neurosignals (2005) [Pubmed]
  14. Isolation and identification of N1-methylnicotinic acid (trigonelline) from rat urine. Yuyama, S., Suzuki, T. J. Nutr. Sci. Vitaminol. (1985) [Pubmed]
  15. Changes in trigonelline (N-methylnicotinic acid) content and nicotinic acid metabolism during germination of mungbean (Phaseolus aureus) seeds. Zheng, X.Q., Hayashibe, E., Ashihara, H. J. Exp. Bot. (2005) [Pubmed]
  16. Changes in the concentration of trigonelline in a semi-arid leguminous plant (Prosopis laevigata) induced by an arbuscular mycorrhizal fungus during the presymbiotic phase. Rojas-Andrade, R., Cerda-García-Rojas, C.M., Frías-Hernández, J.T., Dendooven, L., Olalde-Portugal, V., Ramos-Valdivia, A.C. Mycorrhiza (2003) [Pubmed]
  17. Drought stress, peroxidase activity and formaldehyde metabolism in bean plants. Stefanovits-Bányai, E., Sárdi, E., Lakatos, S., Zayan, M., Velich, I. Acta. Biol. Hung. (1998) [Pubmed]
  18. In vitro effect of fenugreek extracts on intestinal sodium-dependent glucose uptake and hepatic glycogen phosphorylase A. Al-Habori, M., Raman, A., Lawrence, M.J., Skett, P. Int. J. Exp. Diabetes Res. (2001) [Pubmed]
  19. Epidemiological and bacteriological investigation of Serratia marcescens epidemic in a nursery and in a neonatal intensive care unit. Montanaro, D., Grasso, G.M., Annino, I., De Ruggiero, N., Scarcella, A., Schioppa, F. The Journal of hygiene. (1984) [Pubmed]
  20. A dihydropyridine carrier system for sustained delivery of 2',3'-dideoxynucleosides to the brain. Palomino, E., Kessel, D., Horwitz, J.P. J. Med. Chem. (1989) [Pubmed]
  21. The excretion of N1-methyl-2-pyridone-5-carboxylic acid and related compounds in human subjects after oral administration of nicotinic acid, trigonelline and N1-methyl-2-pyridone-5-carboxylic acid. Yuyama, S., Suzuki, T. Adv. Exp. Med. Biol. (1991) [Pubmed]
  22. Changes in formaldehyde contents of germinating acorns of Quercus cerris L. under low temperature stress conditions. Németh, Z.I., Albert, L., Varga, S. Acta. Biol. Hung. (1998) [Pubmed]
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