Abstract
This work presented a new analytical methodology based on hydrophilic interaction ultra-performance liquid chromatography coupled with triple-quadrupole tandem mass spectrometry in multiple-reaction monitoring mode for analysis of 24 underivatized free amino acids (FAAs) in functional foods. The proposed method was first reported and validated by assessing the matrix effects, linearity, limit of detections and limit of quantifications, precision, repeatability, stability and recovery of all target compounds, and it was used to determine the nutritional substances of FAAs in ginkgo seeds and further elucidate the nutritional value of this functional food. The result showed that ginkgo seed turned out to be a good source of FAAs with high levels of several essential FAAs and to have a good nutritional value. Furthermore, the principal component analysis was performed to classify the ginkgo seed samples on the basis of 24 FAAs. As a result, the samples could be mainly clustered into three groups, which were similar to areas classification. Overall, the presented method would be useful for the investigation of amino acids in edible plants and agricultural products.
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Cai X, Zou L, Dong J, Zhao L, Wang Y, Xu Q, Xue X, Zhang X, Liang X (2009) Analysis of highly polar metabolites in human plasma by ultra-performance hydrophilic interaction liquid chromatography coupled with quadrupole-time of flight mass spectrometry. Anal Chim Acta 650:10–15
Callejón R, Troncoso A, Morales M (2010) Determination of amino acids in grape-derived products: a review. Talanta 81:1143–1152
Cerrada-Gimenez M, Häkkinen MR, Vepsäläinen J, Auriola S, Alhonen L, Keinänen TA (2012) Polyamine flux analysis by determination of heavy isotope incorporation from 13C, 15N-enriched amino acids into polyamines by LC–MS/MS. Amino Acids 42:451–460
Chen L, Chen Q, Zhang Z, Wan X (2009) A novel colorimetric determination of free amino acids content in tea infusions with 2,4-dinitrofluorobenzene. J Food Compos Anal 22:137–141
Chen L, Song F, Liu Z, Zheng Z, Xing J, Liu S (2012) Multi-residue method for fast determination of pesticide residues in plants used in Traditional Chinese Medicine by ultra-high-performance liquid chromatography coupled to tandem mass spectrometry. J Chromatogr A 1225:132–140
Deng Q, Wang L, Wei F, Xie B, Huang FH, Huang W, Shi J, Huang Q, Tian B, Xue S (2011) Functional properties of protein isolates, globulin and albumin extracted from Ginkgo biloba seeds. Food Chem 124:1458–1465
Friedman M, Levin CE (2012) Nutritional and medicinal aspects of d-amino acids. Amino Acids 42:1553–1582
Jandera P (2011) Stationary and mobile phases in hydrophilic interaction chromatography. Anal Chim Acta 692:1–25
Jia S, Kang YP, Park JH, Lee J, Kwon SW (2011) Simultaneous determination of 23 amino acids and 7 biogenic amines in fermented food samples by liquid chromatography/quadrupole time-of-flight mass spectrometry. J Chromatogr A 128:9174–9182
Johnsen E, Wilson SR, Odsbu I, Krapp A, Malerod H, Skarstad K, Lundanes E (2011) Hydrophilic interaction chromatography of nucleoside triphosphates with temperature as a separation parameter. J Chromatogr A 1218:5981–5986
Kaiser A, Khomutov AR, Simonian A, Agostinelli E (2012) A rapid and robust assay for the determination of the amino acid hypusine as a possible biomarker for a high-throughput screening of antimalarials and for the diagnosis and therapy of different diseases. Amino Acids 42:1651–1659
Kvitvang HFN, Andreassen T, Adam T, Villas-Bôas SG, Bruheim P (2011) Highly sensitive GC/MS/MS method for quantitation of amino and nonamino organic acids. Anal Chem 83:2705–2711
Langrock T, Czihal P, Hoffmann R (2006) Amino acid analysis by hydrophilic interaction chromatography coupled on-line to electrospray ionization mass spectrometry. Amino Acids 30:291–297
Leggio A, Belsito EL, De Marco R, Liguori A, Siciliano C, Spinella M (2012) Simultaneous extraction and derivatization of amino acids and free fatty acids in meat products. J Chromatogr A 1241:96–102
Li G, Cui Y, You J, Zhao X, Sun Z, Xia L, Suo Y, Wang X (2011) Determination of trace amino acids in human serum by a selective and sensitive pre-column derivatization method using HPLC-FLD-MS/MS and derivatization optimization by response surface methodology. Amino Acids 40:1185–1193
Major RT (1967) The ginkgo, the most ancient living tree. Science 157:1270–1273
Matuszewski BK, Constanzer ML, Chavez-Eng CM (2003) Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC–MS/MS. Anal Chem 74:2034–2040
Neville DCA, Alonzi DS, Butters TD (2012) Hydrophilic interaction liquid chromatography of anthranilic acid-labelled oligosaccharides with a 4-aminobenzoic acid ethyl ester-labelled dextran hydrolysate internal standard. J Chromatogr A 1233:66–70
Qu J, Chen W, Luo G, Wang Y, Xiao S, Ling Z, Chen G (2002a) Rapid determination of underivatized pyroglutamic acid, glutamic acid, glutamine and other relevant amino acids in fermentation media by LC–MS–MS. Analyst 127:66–69
Qu J, Wang Y, Luo G, Wu Z, Yang C (2002b) Validated quantitation of underivatized amino acids in human blood samples by volatile ion-pair reversed-phase liquid chromatography coupled to isotope dilution tandem mass spectrometry. Anal Chem 74:2034–2040
Rambla-Alegre M, Esteve-Romero J, Carda-Broch S (2012) Is it really necessary to validate an analytical method or not? That is the question. J Chromatogr A 1232:101–109
Rebane R, Herodes K (2012) Comparison of three buffer solutions for amino acid derivatization and following analysis by liquid chromatography electrospray mass spectrometry. J Chromatogr A 1245:134–142
Sanchez-Hernandez L, Marina ML, Crego AL (2012) A capillary electrophoresis–tandem mass spectrometry methodology for the determination of non-protein amino acids in vegetable oils as novel markers for the detection of adulterations in olive oils. J Chromatogr A 1218:4944–4951
Sarazin C, Delaunay N, Costanza C, Eudes V, Mallet JM, Gareil P (2011) New avenue for mid UV-range detection of underivatized carbohydrates and aminoacids in capillary electrophoresis. Anal Chem 83:7381–7387
Singh B, Kaur P, Singh GRD, Ahuja PS (2008) Biology and chemistry of Ginkgo biloba. Fitoterapia 79:401–408
Song Y, Funatsu T, Tsunoda M (2012) Rapid determination of amino acids in biological samples using a monolithic silica column. Amino Acids 42:1897–1902
Strieglerová L, Kubáň P, Boček P (2011) Electromembrane extraction of amino acids from body fluids followed by capillary electrophoresis with capacitively coupled contactless conductivity detection. J Chromatogr A 1218:6248–6255
Syu KY, Lin CL, Huang HC, Lin JK (2008) Determination of theanine, GABA, and other amino acids in green, oolong, black, and pu-erh teas with dabsylation and high-performance liquid chromatography. J Agric Food Chem 56:7637–7643
Van Beek TA (2002) Chemical analysis of Ginkgo biloba leaves and extracts. J Chromatogr A 967:21–55
Vioque J, Alaiz M, Girón-Calle J (2012) Nutritional and functional properties of Vicia faba protein isolates and related fractions. Food Chem 132:67–72
Wang J, Wang JL, Xin X (2000) Seed growth characteristics of Ginkgo biloba and its physiological change. Chin J Appl Ecol 11:507–512
Wang L, Xu R, Hu B, Li W, Sun Y, Tu Y, Zeng X (2010) Analysis of free amino acids in Chinese teas and flower of tea plant by high performance liquid chromatography combined with solid-phase extraction. Food Chem 123:1259–1266
Wang C, Zhang W, Song F, Liu Z, Liu S (2012) A simple method for the analysis by MS/MS of underivatized amino acids on dry blood spots from newborn screening. Amino Acids 42:1889–1895
Wu L, Zhou J, Xue X, Li Y, Zhao J (2009) Fast determination of 26 amino acids and their content changes in royal jelly during storage using ultra-performance liquid chromatography. J Food Compos Anal 22:242–249
Xing Q, Liang T, Shen G, Wang X, Jin Y, Liang X (2012) Comprehensive HILIC × RPLC with mass spectrometry detection for the analysis of saponins in Panax notoginseng. Analyst 137:2239–2249
Yan D, Li G, Xiao XH, Dong XP, Li ZL (2007) Direct determination of fourteen underivatized amino acids from Whitmania pigra by using liquid chromatography-evaporative light scattering detection. J Chromatogr A 1138:301–304
Acknowledgments
This work was supported by A Project Funded by the National Science and Technology Support Program of China (2011BAI04B03), the 2009’ Program for New Century Excellent Talents by the Ministry of Education (NCET-09-0163), the Priority Academic Program Development of Jiangsu Higher Education Institutions (ysxk-2010), and the Construction Project for Jiangsu Engineering Center of Innovative Drug from Blood-conditioning TCM Formulae. We are grateful to Mr. Wei Jiang (Taixing, Jiangsu province, China) for collecting samples. We are also pleased to thank Waters China Ltd. for technical support.
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Zhou, G., Pang, H., Tang, Y. et al. Hydrophilic interaction ultra-performance liquid chromatography coupled with triple-quadrupole tandem mass spectrometry for highly rapid and sensitive analysis of underivatized amino acids in functional foods. Amino Acids 44, 1293–1305 (2013). https://doi.org/10.1007/s00726-013-1463-7
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DOI: https://doi.org/10.1007/s00726-013-1463-7