N,N-dimethylpiperidinium (mepiquat): Part 1. Formation in model systems and relevance to roasted food products

References

• Ahmed MU, Thorpe SR, Baynes JW. 1986. Identification of the Nε-carboxymethyllysine as a degradation product of fructosyllysine in glycated protein. J Biol Chem. 261:4889–4894.
   PubMed Web of Science ®Google Scholar
• Bray L, Chriqui D, Gloux K, Le Rudulier D, Meyer M, Peduzzi J. 1991. Betaines and free amino acids in salt stressed vitroplants and winter resting buds of Populus trichocarpa × deltoids. Physiol Plant. 83:136–143.
   Google Scholar
• Campa C, Ballester JF, Doulbeau S, Dussert S, Hamon S, Noirot M. 2004. Trigonelline and sucrose diversity in wild Coffea species. Food Chem. 88:39–43.
   Web of Science ®Google Scholar
• Cho Y, Lightfoot DA, Wood AJ. 1999. Trigonelline concentrations in slat stressed leaves of cultivated Glycine max. Phytochemistry. 52:1235–1238.
   Web of Science ®Google Scholar
• Corol D-I, Ravel C, Raksegi M, Bedo Z, Charmet G, Beale MH, Shewry PR, Ward JL. 2012. Effects of genotype and environment of the contents of betaine, choline, and trigonelline in cereal grains. J Agric Food Chem. 60:5471–5481.
   PubMed Web of Science ®Google Scholar
• Drusch S, Faist V, Erbersdobler HF. 1999. Determination of the Nε-carboxymethyllysine in milk products by a modified reversed-phase HPLC method. Food Chem. 65:547–553.
   Web of Science ®Google Scholar
• Evangelisti F, Calgano C, Zunin P. 1994. Relationship between blocked lysine and carbohydrate composition of infant formulas. J Food Sci. 59:335–337.
   Web of Science ®Google Scholar
• Ferrer I, Thurman EM. 2007. Importance of the electron mass in the calculations of exact mass by time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 21:2538–2539.
   PubMed Web of Science ®Google Scholar
• Finot A, Bujard E, Mottu F, Mauron J. 1977. Availability of the true Schiff’s base of lysine. Chemical evaluation of the Schiff’s base between lysine and lactose in milk. In: Friedman M, editor. Protein crosslinking – B. Nutritional and medical consequences. New York (NY): Plenum Publishing Corporation; 343–365.
   Google Scholar
• Friedman M. 1996. Food browning and its prevention: an overview. J Agric Food Chem. 44:631–653.
   Web of Science ®Google Scholar
• Fu M-X, Requena JR, Jenkins AJ, Lyons TJ, Baynes JW, Thorpe SR. 1996. The advanced glycation end product, Nε-(carboxymethyl)lysine, is a product of both lipid peroxidation and glycoxidation reactions. J Biol Chem. 271:9982–9986.
   PubMed Web of Science ®Google Scholar
• Goldmann T, Davidek T, Gouezec E, Blank I, Bertholet M-C SR. 2009. Formation of styrene during the Maillard reaction is negligible. Food Addit Contam Part A. 26:583–594.
   Web of Science ®Google Scholar
• Grandhee SK, Monnier VM. 1991. Mechanism of formation of the Maillard protein cross-link pentosidine. J Biol Chem. 266:11649–11653.
   PubMed Web of Science ®Google Scholar
• Henle T. 2005. Protein-bound advanced glycation endproducts (AGEs) as bioactive amino acid derivatives in foods. Amino Acids. 29:313–322.
   PubMed Web of Science ®Google Scholar
• Henle T, Schwarzenbolz U, Klostermeyer H. 1997. Detection and quantification of pentosidine in foods. Z Lebensm Unters Forsh. 204:95–98.
   Google Scholar
• Henle T, Walter H, Klostermeyer H. 1991. Evaluation of the extent of the early Maillard-reaction in milk products by direct measurement of the Amadori product lactuloselysine. Z Lebensm Unters Forsh. 193:119–122.
   PubMedGoogle Scholar
• Jahns E. 1885. Ueber die Alkaloïde des Bockshornsamens. Berichte der deutschen chemischen Gesellschaft. 18:2518–2523.
   Google Scholar
• Koshiro Y, Zheng X-Q, Wang M-L, Nagai C, Ashihara H. 2006. Changes in content and biosynthetic activity of caffeine and trigonelline during growth and ripening of Coffea Arabica and Coffea canephora fruits. Plant Sci. 171:242–250.
   Web of Science ®Google Scholar
• Lang R, Yagar EF, Eggers R, Hofmann T. 2008. Quantitative investigation of trigonelline, nicotinic acid, and nicotinamide in foods, urine, and plasma by means of LC-MS/MS and stable isotope dilution analysis. J Agric Food Chem. 56:11114–11121.
   PubMed Web of Science ®Google Scholar
• Lee G, Carrow RN, Duncan RR, Eiteman MA, Rieger MW. 2008. Synthesis of organic osmolytes and salt tolerance mechanisms in Paspalum vaginatum. Environ Exp Bot. 63:19–27.
   Web of Science ®Google Scholar
• Lindenmeier M, Faist V, Hofman T. 2002. Structural and functional characterization of pronyl-lysine, a novel protein modification in bread crust melanoidins showing in vitro antioxidative and phase I/II enzyme modulating activity. J Agric Food Chem. 50:6997–7006.
   PubMed Web of Science ®Google Scholar
• Locas CP, Yaylayan VA. 2008. Further insight into thermally and pH-induced generation of acrylamide from glucose/asparagine model systems. J Agric Food Chem. 56:6069–6074.
   PubMed Web of Science ®Google Scholar
• Matsui A, Yin Y, Yamanaka K, Iwasaki M, Ashihara H. 2007. Metabolic fate of nicotinamide in higher plants. Physiol. Plant. 131:191–200.
   PubMed Web of Science ®Google Scholar
• Nayakama T, Hayase F, Kato H. 1980. Formation of the ε-(2-formyl-5-hydroxymethyl-pyrrol-1-yl)-L-norleucine in the Maillard reaction between D-glucose and L-lysine. Agric Biol Chem. 44:1201–1202.
   Google Scholar
• Nikolov P, Yaylayan VA. 2010. Formation of pent-4-en-1-amine, the counterpart of acrylamide from lysine and its conversion into piperidine in lysine/glucose reaction mixtures. J Agric Food Chem. 58:4456–4462.
   PubMed Web of Science ®Google Scholar
• Peiser HS, Holden NE, De Bièvre P, Barnes IL, Hagemann R, De Laeter JR, Murphy TJ, Roth E, Shima M, Thode HG. 1984. Element by element review of their atomic weights. Pure Appl Chem. 56:695–768.
   Web of Science ®Google Scholar
• Perrone D, Donangelo CM, Farah A. 2008. Fast simultaneous analysis of caffeine, trigonelline, nicotinic acid and sucrose in coffee by liquid chromatography-mass spectrometry. Food Chem. 110:1030–1035.
   PubMed Web of Science ®Google Scholar
• Rajasekaran LR, Aspinall D, Jones GP, Paleg LG. 2001. Stress metabolism. IX. Effect of salt stress on trigonelline accumulation in tomato. Can J Plant Sci. 81:497–498.
   Google Scholar
• Riediker S, Obrist H, Varga N, Stadler RH. 2002. Determination of chlormequat and mepiquat in pear, tomato, and wheat flour using on-line solid-phase extraction (Prospekt) coupled with liquid chromatography-electrospray ionization tandem mass spectrometry. J Chromatogr A. 966:15–23.
   PubMed Web of Science ®Google Scholar
• Stadler RH, Robert F, Riediker S, Varga N, Davidek T, Devaud S, Goldmann T, Hau J, Blank I. 2004. In-depth mechanistic study on the formation of acrylamide and other vinylogous compounds by the Maillard reaction. J Agric Food Chem. 52:5550–5558.
   PubMed Web of Science ®Google Scholar
• Stadler RH, Varga N, Hau J, Arce Vera F, Dieter HW. 2002a. Alkylpyridiniums. 1. Formation in model systems via thermal degradation of trigonelline. J Agric Food Chem. 50:1192–1199.
   PubMed Web of Science ®Google Scholar
• Stadler RH, Varga N, Milo C, Schilter B, Arce Vera F, Dieter HW. 2002b. Alkylpyridiniums. 2. Isolation and quantification in roasted and ground coffees. J Agric Food Chem. 50:1200–1206.
   PubMed Web of Science ®Google Scholar
• Stadler RH, Verzegnassi L, Varga N, Grigorov M, Studer A, Riediker S, Schilter B. 2003. Formation of vinylogous compounds in model Maillard reaction systems. Chem Res Toxicol. 16:1242–1250.
   PubMed Web of Science ®Google Scholar
• Stennert A, Maier HG. 1994. Trigonelline in coffee. Z Lebensm Unters Forsch. 199:198–200.
   PubMedGoogle Scholar
• Tramontano WA, Jouve D. 1997. Trigonelline accumulation in salt-stressed legumes and the role of other osmoregulators as cell cycle control agents. Phytochemistry. 44:1037–1040.
   Web of Science ®Google Scholar
• Tramontano WA, McGinley PA, Ciancaglini EF, Evans LS. 1986. A survey of trigonelline concentrations in dry seeds of the Dicotyledoneae. Environ Exp Botany. 26:197–205.
   Web of Science ®Google Scholar
• Wermann S, Theurillat V, Verzegnassi L, Hofmann J, Kuchenbecker R, Constable A, Delatour T, Stadler RH. 2014. N, N-Dimethylpyridinium (mepiquat) Part 2. Formation in foods during thermal processing. Food Addit Contam Part A. Available from: http://www.tandfonline.com/doi/abs/10.1080/19440049.2013.871585
   Google Scholar