Identification of quinoline, carboline and glycinamide compounds in cow milk using HRMS and NMR

Food Chemistry

Volumn 141, Issue 3, 2013, Pages 1888-1894

  Rouge, Pascal ^a,b   Cornu, Agnès ^a,b   Biesse Martin, Anne Sophie ^b,c   Lyan, Bernard ^d   Rochut, Nadège ^e   Graulet, Benoît ^a,b  

^a UMR1213 HERBIVORES   (France)

^b UNIVERSITÉ CLERMONT AUVERGNE   (France)

^c ICCF   (France)

^d INRA and University of Auvergne   (France)

^e Danone Research   (France)

Author keywords

Cow milk; HPLC DAD; HRMS; Multidimensional NMR; UV absorbing compound

Indexed keywords

FOOD TECHNOLOGY; PHYSICAL CHEMISTRY;

COW MILK; HPLC-DAD; HRMS; MULTIDIMENSIONAL NMR; UV-ABSORBING COMPOUNDS;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CARBOLINE DERIVATIVE; GLYCINAMIDE; QUINOLINE;

ANALYTIC METHOD; ANIMAL FOOD; ARTICLE; EXTRACTION; HETERONUCLEAR MULTIPLE BOND CORRELATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION PROCEDURE; LIGHT ABSORPTION; MILK; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE;

ANIMALIA;

EID: 84879055623     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2013.04.072     Document Type: Article

References (20)

1. Adachi, J., Mizoi, Y., Naito, T., Ogawa, Y., Uetani, Y., & Ninomiya, I. (1991). Identification of tetrahydro-β-carboline-3-carboxylic acid in foodstuffs, human urine and human-milk. Journal of Nutrition, 121(5), 646-652.
2. Bertoni, G., Merlini, L., Nasini, G., & Abenaim, U. (1980). 1-Methyl-β-carboline-3- carboxylic acid, an unusual metabolite from cows fed with corn silage. Journal of Agricultural and Food Chemistry, 28, 672-673.
3. Besle, J. M., Cornu, A., & Jouany, J. P. (1994). Roles of structural phenylpropanoids in forage cell-wall digestion. Journal of the Science of Food and Agriculture, 64(2), 171-190.
4. Besle, J. M., Viala, D., Martin, B., Pradel, P., Meunier, B., Berdague, J. L., et al. (2010). Ultraviolet-absorbing compounds in milk are related to forage polyphenols. Journal of Dairy Science, 93(7), 2846-2856.
5. Cardoso, C. L., Castro-Gamboa, I., Silva, D. H. S., Furlan, M., Epifanio, R. D., Pinto, A. D., et al. (2004). Indole glucoalkaloids from Chimarrhis turbinata and their evaluation (Pubitemid 39602369)
6. Cui, M. C., Chen, F. Z., Fu, J. M., Sheng, G. Y., & Sun, G. P. (2004). Microbial metabolism of quinoline by Comamonas sp. World Journal of Microbiology & Biotechnology, 20(6), 539-543.
7. Gulyaeva, N., & Aniol, V. (2012). Good guys from a shady family. Journal of Neurochemistry, 121(6), 841-842.
8. Inman, W. D., Bray, W. M., Gassner, N. C., Lokey, R. S., Tenney, K., Shen, Y. Y. C., TenDyke, K., Suh, T., & Crews, P. (2010). A β-carboline alkaloid from the Papua New Guinea marine sponge Hyrtios reticulatus. Journal of Natural Products, 73(2), 255-257.
9. Kaiser, J. P., Feng, Y. C., & Bollag, J. M. (1996). Microbial metabolism of pyridine, quinoline, acridine, and their derivatives under aerobic and anaerobic conditions. Microbiological Reviews, 60(3), 483-498.
10. Linares, R. M., Gonzalez, A., Ayala, J. H., Afonso, A. M., & Gonzalez, V. (1995). Protolytic equilibria of indole and several indolecarboxylic acids in micellar media. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 51(10), 1691-1701.
11. Lopez, V., & Lindsay, R. C. (1993). Thermal-stability of some metabolically conjugated potential precursors of flavor components in meat and milk. Journal of Food Science, 58(2), 292-298.
12. Lowry, J. B., Sumpter, E. A., McSweeney, C. S., Schlink, A. C., & Bowden, B. (1993). Phenolic-acids in the fiber of some tropical grasses, effect on feed quality, and their metabolism by sheep. Australian Journal of Agricultural Research, 44(5), 1123-1133.
13. Martin, A. K. (1982). The origin of urinary aromatic compounds excreted by ruminants 3. The metabolism of phenolic compounds to simple phenols. British Journal of Nutrition, 48(03), 497-507. (Pubitemid 13195311)
14. Musshoff, F., Daldrup, T., Bonte, W., Leitner, A., & Lesch, O. M. (1996). Formaldehyde-derived tetrahydroisoquinolines and tetrahydro-b-carbolines in human urine. Journal of Chromatography B: Biomedical Applications, 683(2), 163-176. (Pubitemid 26319560)
15. O'Connell, J. E., & Fox, P. F. (2001). Significance and applications of phenolic compounds in the production and quality of milk and dairy products: A review. International Dairy Journal, 11(3), 103-120. (Pubitemid 32682563)
16. O'Donnell, F., Smyth, T. J., Ramachandran, V. N., & Smyth, W. F. (2010). A study of the antimicrobial activity of selected synthetic and naturally occurring quinolines. International Journal of Antimicrobial Agents, 35(1), 30-38.
17. Otaka, H., Yasuhara, A., & Morita, M. (2003). Determination of bisphenol A and 4- nonylphenol in human milk using alkaline digestion and cleanup by solid-phase extraction. Analytical Sciences, 19(12), 1663-1666.
18. Rose, D. P. (1972). Aspects of tryptophan metabolism in health and disease: A review. Journal of Clinical Pathology, 25, 17-25.
19. Tsuchiya, H., Sato, M., Hayashi, H., Kato, H., Kureshiro, H., & Hayashi, T. (1996). Simultaneous determination of tetrahydro-β-carbolines and β-carbolines. Chromatographia, 43(7-8), 419-425.
20. Zhang, Y. M., Frank, M. W., Zhu, K., Mayasundari, A., & Rock, C. O. (2008). PqsD is responsible for the synthesis of 2,4-dihydroxyquinoline, an extracellular metabolite produced by Pseudomonas aeruginosa. Journal of Biological Chemistry, 283(43), 28788-28794.