An isotope-labeled chemical derivatization method for the quantitation of short-chain fatty acids in human feces by liquid chromatography-tandem mass spectrometry

Analytica Chimica Acta

Volumn 854, Issue , 2015, Pages 86-94

  Han, Jun ^a   Lin, Karen ^a   Sequeira, Carita ^a   Borchers, Christoph H ^a,b  

^a UNIVERSITY OF VICTORIA   (Canada)

^b UNIVERSITY OF VICTORIA   (Canada)

Author keywords

3 Nitrophenylhydrazine; Chemical derivatization; Isotope labeling; Short chain fatty acid; Ultrahigh performance liquid chromatography multiple reaction monitoring mass spectrometr

Indexed keywords

CHAINS; CHEMICAL STABILITY; ELECTROSPRAY IONIZATION; ISOTOPES; LIQUID CHROMATOGRAPHY; LIQUIDS; MASS SPECTROMETRY; NEGATIVE IONS;

3-NITROPHENYLHYDRAZINE; CHEMICAL DERIVATIZATION; ISOTOPE LABELING; MULTIPLE REACTION MONITORING; SHORT-CHAIN FATTY ACIDS;

FATTY ACIDS;

2 METHYLBUTYRIC ACID; 3 METHYL VALERATE; 3 NITROPHENYLHYDRAZINE; ACETIC ACID; BUTYRIC ACID; CARBON 13; HEXANOIC ACID; HEXANOIC ACID DERIVATIVE; HYDRAZINE DERIVATIVE; ISOBUTYRIC ACID; ISOCAPROATE; ISOVALERIC ACID; PROPIONIC ACID; SHORT CHAIN FATTY ACID; UNCLASSIFIED DRUG; VALERIC ACID; VOLATILE FATTY ACID;

ANALYTIC METHOD; ARTICLE; DERIVATIZATION; ELECTROSPRAY; FECES ANALYSIS; HUMAN; ISOTOPE LABELING; LIMIT OF DETECTION; LIMIT OF QUANTITATION; LIPID ANALYSIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MEASUREMENT ACCURACY; MEASUREMENT PRECISION; MULTIPLE REACTION MONITORING; SENSITIVITY ANALYSIS; TANDEM MASS SPECTROMETRY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; CALIBRATION; CHEMISTRY; FECES; PROCEDURES; REPRODUCIBILITY;

CALIBRATION; CHROMATOGRAPHY, LIQUID; FATTY ACIDS, VOLATILE; FECES; HUMANS; ISOTOPE LABELING; LIMIT OF DETECTION; REPRODUCIBILITY OF RESULTS; TANDEM MASS SPECTROMETRY;

EID: 84919337329     PISSN: 00032670     EISSN: 18734324     Source Type: Journal    
DOI: 10.1016/j.aca.2014.11.015     Document Type: Article

References (56)

1. Nicholson J.K., Holmes E., Kinross J., Burcelin R., Gibson G., Jia W., Pettersson S. Host-gut microbiota metabolic interactions. Science 2012, 336:1262-1267.
2. Greenberg N.A., Gassull M.A., Meier R. Short-chain fatty acids: ready for prime time?. Nutr. Clin. Pract. 2006, 21:639-640.
3. Roy C.C., Kien C.L., Bouthillier L., Levy E. Short-chain fatty acids: ready for prime time?. Nutr. Clin. Pract. 2006, 21:351-366.
4. Cummings J.H. Short chain fatty acids in the human colon. Gut 1981, 22:763-779.
5. Macfarlane S., Macfarlane G.T. Regulation of short-chain fatty acid production. Proc. Nutr. Soc. 2003, 62:67-72.
6. Bergman E.N. Energy contributions of volatile fatty acids from the gastrointestinal tract in various species. Physiol. Rev. 1990, 70:567-590.
7. Ruppin H., Bar-Meir S., Soergel K.H., Wood C.M., Schmitt M.G. Absorption of short-chain fatty acids by the colon. Gastroenterology 1980, 78:1500-1507.
8. Wong J.M., de Souza R., Kendall C.W., Emam A., Jenkins D.J. Colonic health: fermentation and short chain fatty acids. J. Clin. Gastroenterol. 2006, 40:235-243.
9. Tan J., McKenzie C., Potamitis M., Thorburn A.N., Mackay C.R., Macia L. The role of short-chain fatty acids in health and disease. Adv. Immunol. 2014, 121:91-119.
10. Murase M., Kimura Y., Nagata Y. Determination of portal short-chain fatty acids in rats fed various dietary fibers by capillary gas chromatography. J. Chromatogr. B Biomed. Appl. 1995, 664:415-420.
11. Cummings J.H., Pomare E.W., Branch W.J., Naylor C.P., Macfarlane G.T. Short chain fatty acids in human large intestine, portal, hepatic and venous blood. Gut 1987, 28:1221-1227.
12. Layden B.T., Angueira A.R., Brodsky M., Durai V., Lowe W.L. Short chain fatty acids and their receptors: new metabolic targets. Transl. Res. 2013, 161:131-140.
13. Gao Z., Yin J., Zhang J., Ward R.E., Martin R.J., Lefevre M., Cefalu W.T., Ye J. Butyrate improves insulin sensitivity and increases energy expenditure in mice. Diabetes 2009, 58:1509-1517.
14. McGrath L.T., Weir C.D., Maynard S., Rowlands B.J. Gas-liquid chromatographic analysis of volatile short chain fatty acids in fecal samples as pentafluorobenzyl esters. Anal. Biochem. 1992, 207:227-230.
15. Demigne C., Morand C., Levrat M.A., Besson C., Moundras C., Remesy C. Effect of propionate on fatty acid and cholesterol synthesis and on acetate metabolism in isolated rat hepatocytes. Br. J. Nutr. 1995, 74:209-219.
16. Fushimi T., Suruga K., Oshima Y., Fukiharu M., Tsukamoto Y., Goda T. Dietary acetic acid reduces serum cholesterol and triacylglycerols in rats fed a cholesterol-rich diet. Br. J. Nutr. 2006, 95:916-924.
17. Brown A.J., Goldsworthy S.M., Barnes A.A., Eilert M.M., Tcheang L., Daniels D., Muir A.I., Wigglesworth M.J., Kinghorn I., Fraser N.J., Pike N.B., Strum J.C., Steplewski K.M., Murdock P.R., Holder J.C., Marshall F.H., Szekeres P.G., Wilson S., Ignar D.M., Foord S.M., Wise A., Dowell S.J. The orphan G protein-coupled receptors GPR41 and GPR43 are activated by propionate and other short chain carboxylic acids. J. Biol. Chem. 2003, 278:11312-11319.
18. Tolhurst G., Heffron H., Lam Y.S., Parker H.E., Habib A.M., Diakogiannaki E., Cameron J., Grosse J., Reimann F., Gribble F.M. Short-chain fatty acids stimulate glucagon-like peptide-1 secretion via the G-protein-coupled receptor FFAR2. Diabetes 2012, 61:364-371.
19. De Vadder F., Kovatcheva-Datchary P., Goncalves D., Vinera J., Zitoun C., Duchampt A., Backhed F., Mithieux G. Microbiota-generated metabolites promote metabolic benefits via gut-brain neural circuits. Cell 2014, 156:84-96.
20. Hamer H.M., Jonkers D., Venema K., Vanhoutvin S., Troost F.J., Brummer R.J. Review article: the role of butyrate on colonic function. Aliment. Pharmacol. Ther. 2008, 27:104-119.
21. Huda-Faujan N., Abdulamir A.S., Fatimah A.B., Anas O.M., Shuhaimi M., Yazid A.M., Loong Y.Y. The impact of the level of the intestinal short chain fatty acids in inflammatory bowel disease patients versus healthy subjects. Open Biochem. J. 2010, 4:53-58.
22. Mortensen P.B., Andersen J.R., Arffmann S., Krag E. Short-chain fatty acids and the irritable bowel syndrome: the effect of wheat bran. Scand. J. Gastroenterol. 1987, 22:185-192.
23. Treem W.R., Ahsan N., Kastoff G., Hyams J.S. Fecal short-chain fatty acids in patients with diarrhea-predominant irritable bowel syndrome: in vitro studies of carbohydrate fermentation. J. Pediatr. Gastroenterol. Nutr. 1996, 23:280-286.
24. Ramakrishna B.S., Mathan V.I. Colonic dysfunction in acute diarrhoea: the role of luminal short chain fatty acids. Gut 1993, 34:1215-1218.
25. Scheppach W., Bartram H.P., Richter F. Role of short-chain fatty acids in the prevention of colorectal cancer. Eur. J. Cancer 1995, 31A:1077-1080.
26. Zhao G., Nyman M., Jonsson J.A. Rapid determination of short-chain fatty acids in colonic contents and faeces of humans and rats by acidified water-extraction and direct-injection gas chromatography. Biomed. Chromatogr. 2006, 20:674-682.
27. Arellano M., Jomard P., El Kaddouri S., Roques C., Nepveu F., Couderc F. Routine analysis of short-chain fatty acids for anaerobic bacteria identification using capillary electrophoresis and indirect ultraviolet detection. J. Chromatogr. B Biomed. Sci. Appl. 2000, 741:89-100.
28. Barbas C., Adeva N., Aguilar R., Rosillo M., Rubio T., Castro M. Quantitative determination of short-chain organic acids in urine by capillary electrophoresis. Clin. Chem. 1998, 44:1340-1342.
29. Kotani A., Miyaguchi Y., Kohama M., Ohtsuka T., Shiratori T., Kusu F. Determination of short-chain fatty acids in rat and human feces by high-performance liquid chromatography with electrochemical detection. Anal. Sci. 2009, 25:1007-1011.
30. Horspool L.J., McKellar Q.A. Determination of short-chain fatty acids in equine caecal liquor by ion exchange high performance liquid chromatography after solid phase extraction. Biomed. Chromatogr. 1991, 5:202-206.
31. Stein J., Kulemeier J., Lembcke B., Caspary W.F. Simple and rapid method for determination of short-chain fatty acids in biological materials by high-performance liquid chromatography with ultraviolet detection. J. Chromatogr. 1992, 576:53-61.
32. Schiffels J., Baumann M.E., Selmer T. Facile analysis of short-chain fatty acids as 4-nitrophenyl esters in complex anaerobic fermentation samples by high performance liquid chromatography. J. Chromatogr. A 2011, 1218:5848-5851.
33. Miwa H., Hiyama C., Yamamoto M. High-performance liquid chromatography of short-and long-chain fatty acids as 2-nitrophenylhydrazides. J. Chromatogr. A 1985, 321:165-174.
34. Miwa H., Yamamoto M. Improved method of determination of biologically important C10:0-C22:6 fatty acids as their 2-nitrophenylhydrazides by reversed-phase high-performance liquid chromatography. J. Chromatogr. 1986, 351:275-282.
35. Miwa H., Yamamoto M. High-performance liquid chromatographic analysis of serum short-chain fatty acids by direct derivatization. J. Chromatogr. 1987, 421:33-41.
36. den Besten G., van Eunen K., Groen A.K., Venema K., Reijngoud D.J., Bakker B.M. The role of short-chain fatty acids in the interplay between diet, gut microbiota, and host energy metabolism. J. Lipid Res. 2013, 54:2325-2340.
37. Crown S.B., Antoniewicz M.R. Publishing 13C metabolic flux analysis studies: a review and future perspectives. Metab. Eng. 2013, 20:42-48.
38. Antoniewicz M.R. 13C metabolic flux analysis: optimal design of isotopic labeling experiments. Curr. Opin. Biotechnol. 2013, 24:1116-1121.
39. Antoniewicz M.R. Tandem mass spectrometry for measuring stable-isotope labeling. Curr. Opin. Biotechnol. 2013, 24:48-53.
40. Husek P. Chloroformates in gas chromatography as general purpose derivatizing agents. J. Chromatogr. B Biomed. Sci. Appl. 1998, 717:57-91.
41. Zheng X., Qiu Y., Zhong W., Baxter S., Su M., Li Q., Xie G., Ore B.M., Qiao S., Spencer M.D., Zeisel S.H., Zhou Z., Zhao A., Jia W. A targeted metabolomic protocol for short-chain fatty acids and branched-chain amino acids. Metabolomics 2013, 9:818-827.
42. Meesters R.J., van Eijk H.M., ten Have G.A., de Graaf A.A., Venema K., van Rossum B.E., Deutz N.E. Application of liquid chromatography-mass spectrometry to measure the concentrations and study the synthesis of short chain fatty acids following stable isotope infusions. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2007, 854:57-62.
43. van Eijk H.M., Bloemen J.G., Dejong C.H. Application of liquid chromatography-mass spectrometry to measure short chain fatty acids in blood. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2009, 877:719-724.
44. Vogeser M., Seger C. Pitfalls associated with the use of liquid chromatography-tandem mass spectrometry in the clinical laboratory. Clin. Chem. 2010, 56:1234-1244.
45. Mulvana D.E. Critical topics in ensuring data quality in bioanalytical LC-MS method development. Bioanalysis 2010, 2:1051-1072.
46. Bruheim P., Kvitvang H.F., Villas-Boas S.G. Stable isotope coded derivatizing reagents as internal standards in metabolite profiling. J. Chromatogr. A 2013, 1296:196-203.
47. Lamos S.M., Shortreed M.R., Frey B.L., Belshaw P.J., Smith L.M. Relative quantification of carboxylic acid metabolites by liquid chromatography-mass spectrometry using isotopic variants of cholamine. Analyt. Chem. 2007, 79:5143-5149.
48. Yang W.C., Adamec J., Regnier F.E. Enhancement of the LC/MS analysis of fatty acids through derivatization and stable isotope coding. Analyt. Chem. 2007, 79:5150-5157.
49. Guo K., Li L. High-performance isotope labeling for profiling carboxylic acid-containing metabolites in biofluids by mass spectrometry. Analyt. Chem. 2010, 82:8789-8793.
50. Han J., Gagnon S., Eckle T., Borchers C.H. Metabolomic analysis of key central carbon metabolism carboxylic acids as their 3-nitrophenylhydrazones by UPLC/ESI-MS. Electrophoresis 2013, 34:2891-2900.
51. Yomota C., Ohnishi Y. Determination of biotin following derivatization with 2-nitrophenylhydrazine by high-performance liquid chromatography with on-line UV detection and electrospray-ionization mass spectrometry. J. Chromatogr. A 2007, 1142:231-235.
52. Miwa H. High-performance liquid chromatographic determination of free fatty acids and esterified fatty acids in biological materials as their 2-nitrophenylhydrazides. Anal. Chim. Acta 2002, 465:237-255.
53. USFDA Draft Guidance for Industry: Bioanalytical Method Validation 1999, US Food and Drug Administration, Rockville, MD, U. S. A.
54. Cook S.I., Sellin J.H. Review article: short chain fatty acids in health and disease. Aliment. Pharmacol. Ther. 1998, 12:499-507.
55. Hijova E., Chmelarova A. Short chain fatty acids and colonic health. Bratisl. Lek. Listy 2007, 108:354-358.
56. Binder H.J. Role of colonic short-chain fatty acid transport in diarrhea. Annu. Rev. Physiol. 2010, 72:297-313.