Simultaneous Quantification of Five Stereoisomeric Hexoses in Nine Biological Matrices Using Ultrahigh Performance Liquid Chromatography with Tandem Mass Spectrometry

Journal of Analysis and Testing - Tập 4 - Trang 249-256 - 2020
Jiali Zuo1, Runxian Cai1, Yanpeng An1, Huiru Tang1
1State Key Laboratory of Genetic Engineering, Metabonomics and Systems Biology Laboratory At Shanghai International Centre for Molecular Phenomics, Zhongshan Hospital and School of Life Sciences, Human Phenome Institute, Fudan University, Shanghai, China

Tóm tắt

Stereoisomeric hexoses are present in almost all biological organisms in the forms of aldoses and ketoses, with diverse physiological and pathophysiological functions. Accurate and simultaneous quantification is vital for understanding their functions individually. However, such analysis remains challenging owing to their highly similar behavior in chromatography and mass spectrometry. By combining the pre-column 3-nitrophenylhydrazine derivatization and ultrahigh performance liquid chromatography tandem mass spectrometry (UHPLC-MS/MS), here, we developed a method for simultaneous quantification of five important stereoisomeric hexoses including D-glucose, D-galactose, D-mannose, D-fructose and L-sorbose representing both aldoses and ketoses. The method achieved baseline-separation for all these five derivatized hexoses chromatographically and had high sensitivity (LOD, femtomole on column), excellent linearity (R2 > 0.995) and efficiency with stable-isotope dilution. With this method, we further quantified these hexoses in nine biological matrices including human biofluids (serum, urine and saliva), human cells, human and mouse feces, rat liver tissue, mung-bean seeds and peach pulp. The results provided quantitative data for these hexoses in multiple biological samples and showed significant concentration diversity for these hexoses in different biological samples, which demonstrated the applicability of the method for simultaneous quantification of these hexose phenotypes of biological systems. • An optimized UHPLC-MS/MS method based on 3-nitrophenylhydrazine derivatization. • Simultaneous quantification of five stereoisomeric hexoses. • Quantitative results for these five hexoses in nine different biological matrices.

Tài liệu tham khảo

Coelho AI, Berry GT, Rubio-Gozalbo ME. Galactose metabolism and health. Curr Opin Clin Nutr Metab Care. 2015;18:422–7.

Hannou SA, Haslam DE, McKeown NM, Herman MA. Fructose metabolism and metabolic disease. J Clin Invest. 2018;128:545–55.

Dolan LC, Potter SM, Burdock GA. Evidence-based review on the effect of normal dietary consumption of fructose on blood lipids and body weight of overweight and obese individuals. Crit Rev Food Sci Nutr. 2010;50:889–918.

Kawasaki T, Akanuma H, Yamanouchi T. Increased fructose concentrations in blood and urine in patients with diabetes. Diabetes Care. 2002;25:353–7.

Chao HW, Chao SW, Lin H, Ku HC, Cheng CF. Homeostasis of glucose and lipid in non-alcoholic fatty liver disease. Int J Mol Sci. 2019;20:298–315.

Ouyang X, Cirillo P, Sautin Y, McCall S, Bruchette JL, Diehl AM, Johnson RJ, Abdelmalek MF. Fructose consumption as a risk factor for non-alcoholic fatty liver disease. J Hepatol. 2008;48:993–9.

Mardinoglu A, Stančáková A, Lotta LA, Kuusisto J, Boren J, Blüher M, Wareham NJ, Ferrannini E, Groop PH, Laakso M, Langenberg C, Smith U. Plasma mannose levels are associated with incident type 2 diabetes and cardiovascular disease. Cell Metab. 2017;26:281–3.

Gonzalez PS, O’Prey J, Cardaci S, Barthet VJA, Sakamaki J, Beaumatin F, Roseweir A, Gay DM, Mackay G, Malviya G, Kania E, Ritchie S, Baudot AD, Zunino B, Mrowinska A, Nixon C, Ennis D, Hoyle A, Millan D, McNeish IA, Sansom OJ, Edwards J, Ryan KM. Mannose impairs tumour growth and enhances chemotherapy. Nature. 2018;563:719–23.

Bantle JP. Dietary fructose and metabolic syndrome and diabetes. J Nutr. 1268S;139:1263S–8S.

Frey PA. The Leloir pathway: a mechanistic imperative for three enzymes to change the stereochemical configuration of a single carbon in galactose. FASEB J. 1996;10:461–70.

Wursch P, Welsch C, Arnaud MJ. Metabolism of L-sorbose in the rat and the effect of the intestinal microflora on its utilization both in the rat and in the human. Nutr Metab. 1979;23:145–55.

Burns JJ, Mosbach EH, Schulenberg S, Reichenthal J. Studies on the incorporation of C14 administered as l-sorbose into l-ascorbic acid and d-glucose in rats. J Biol Chem. 1955;214:507–14.

Sun M, Wu W, Liu Z, Cong Y. Microbiota metabolite short chain fatty acids, GCPR, and inflammatory bowel diseases. J Gastroenterol. 2017;52:1–8.

Sato T, Kusuhara S, Yokoi W, Ito M, Miyazaki K. Prebiotic potential of L-sorbose and xylitol in promoting the growth and metabolic activity of specific butyrate-producing bacteria in human fecal culture. FEMS Microbiol Ecol. 2017;93:1–10.

Nagata Y, Mizuta N, Kanasaki A, Tanaka K. Rare sugars, d-allulose, d-tagatose and d-sorbose, differently modulate lipid metabolism in rats. J Sci Food Agric. 2018;98:2020–6.

Faeh D, Minehira K, Schwarz JM, Periasamy R, Park S, Tappy L. Effect of fructose overfeeding and fish oil administration on hepatic de novo lipogenesis and insulin sensitivity in healthy men. Diabetes. 2005;54:1907–13.

Goncalves MD, Lu C, Tutnauer J, Hartman TE, Hwang SK, Murphy CJ, Pauli C, Morris R, Taylor S, Bosch K, Yang S, Wang Y, Van Riper J, Carl Lekaye H, Roper J, Kim Y, Chen Q, Gross SS, Rhee KY, Cantley LC, Yun Y. High-fructose corn syrup enhances intestinal tumor growth in mice. Science. 2019;363:1345–9.

Chen W, Wei W, Jia L, Chen W, Jin X, Wang M. GLUT5-mediated fructose utilization drives lung cancer growth by stimulating fatty acid synthesis and AMPK/mTORC1 signaling. JCI Insight. 2020;5:1–17.

Preston GM, Calle RA. Elevated serum sorbitol and not fructose in type 2 diabetic patients. Biomark Insights. 2010;5:33–8.

Lee S, Zhang C, Kilicarslan M, Piening BD, Bjornson E, Hallström BM, Groen AK, Ferrannini E, Laakso M, Snyder M, Blüher M, Uhlen M, Nielsen J, Smith U, Serlie MJ, Boren J, Mardinoglu A. Integrated network analysis reveals an association between plasma mannose levels and insulin resistance. Cell Metab. 2016;24:172–84.

Amano E, Funakoshi S, Yoshimura K, Hirano S, Ohmi S, Takata H, Terada Y, Fujimoto S. Fasting plasma mannose levels are associated with insulin sensitivity independent of BMI in Japanese individuals with diabetes. Diabetol Metab Syndr. 2018;10:88–94.

Campi B, Codini S, Bisoli N, Baldi S, Zucchi R, Ferrannini E, Saba A. Quantification of D-mannose in plasma: development and validation of a reliable and accurate HPLC-MS-MS method. Clin Chim Acta. 2019;493:31–5.

Ferrannini E, Bokarewa M, Brembeck P, Baboota R, Hedjazifar S, Andersson K, Baldi S, Campi B, Muscelli E, Saba A, Sterner I, Wasen C, Smith U. Mannose is an insulin-regulated metabolite reflecting whole-body insulin sensitivity in man. Metab Clin Exp. 2020;102:153974.

Zhang P, Wang Z, Xie M, Nie W, Huang L. Detection of carbohydrates using a pre-column derivatization reagent 1-(4-isopropyl) phenyl-3-methyl-5-pyrazolone by high-performance liquid chromatography coupled with electrospray ionization mass spectrometry. J Chromatogr B. 2010;878:1135–44.

Hong Q, Ruhaak LR, Totten SM, Smilowitz JT, German JB, Lebrilla CB. Label-free absolute quantitation of oligosaccharides using multiple reaction monitoring. Anal Chem. 2014;86:2640–7.

Lv Y, Yang X, Zhao Y, Ruan Y, Yang Y, Wang Z. Separation and quantification of component monosaccharides of the tea polysaccharides from Gynostemma pentaphyllum by HPLC with indirect UV detection. Food Chem. 2009;112:742–6.

Ma C, Sun Z, Chen C, Zhang L, Zhu S. Simultaneous separation and determination of fructose, sorbitol, glucose and sucrose in fruits by HPLC-ELSD. Food Chem. 2014;145:784–8.

Zhang Z, Khan NM, Nunez KM, Chess EK, Szabo CM. Complete monosaccharide analysis by high-performance anion-exchange chromatography with pulsed amperometric detection. Anal Chem. 2012;84:4104–10.

Medeiros PM, Simoneit BRT. Analysis of sugars in environmental samples by gas chromatography-mass spectrometry. J Chromatogr A. 2007;1141:271–8.

Xu G, Amicucci MJ, Cheng Z, Galermo AG, Lebrilla CB. Revisiting monosaccharide analysis-quantitation of a comprehensive set of monosaccharides using dynamic multiple reaction monitoring. Analyst. 2018;143:200–7.

Anumula KR. High-sensitivity and high-resolution methods for glycoprotein analysis. Anal Biochem. 2000;283:17–26.

Anumula KR. Quantitative determination of monosaccharides in glycoproteins by HPLC with highly sensitive fluorescence detection. Anal Biochem. 1994;220:275–83.

Hase S, Ibuki T, Ikenaka T. Reexamination of the pyridylamination used for fluorescence labeling of oligosaccharides and its application to glycoproteins. J Biochem. 1984;95:197–203.

Karamanos NK, Tsegenidis T, Antonopoulos CA. Analysis of neutral sugars as dinitrophenyl-hydrazones by high-performance liquid chromatography. J Chromatogr A. 1987;405:221–8.

Han J, Lin K, Sequria C, Yang J, Borchers CH. Quantitation of low molecular weight sugars by chemical derivatization-liquid chromatography/multiple reaction monitoring/mass spectrometry. Electrophoresis. 2016;37:1851–60.

Wu X, Li N, Li H, Tang H. An optimized method for NMR-based plant seed metabolomic analysis with maximized polar metabolite extraction efficiency, signal-to-noise ratio, and chemical shift consistency. Analyst. 2014;139:1769–78.

An Y, Xu W, Li H, Lei H, Zhang L, Hao F, Duan Y, Yan X, Zhao Y, Wu J, Wang Y, Tang H. High-fat diet induces dynamic metabolic alterations in multiple biological matrices of rats. J Proteome Res. 2013;12:3755–68.

Matyash V, Liebisch G, Kurzchalia TV, Shevchenko A, Schwudke D. Lipid extraction by methyl-terf-butyl ether for high-throughput lipidomics. J Lipid Res. 2008;49:1137–46.

Thông tin
Thông tin xuất bản

Journal of Analysis and Testing

Tập 4

249-256

Thông tin tác giả