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Simultaneous Determination of Melatonin, l-Tryptophan, and two l-Tryptophan-Derived Esters in Food by HPLC with Graphene Oxide/SiO2 Nanocomposite as the Adsorbent

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Abstract

In this research, a dispersive solid-phase extraction (dSPE) with graphene oxide@SiO2 (GO@SiO2) nanocomposites as the adsorbent followed by high-performance liquid chromatography analysis was developed for simultaneous determination of melatonin, l-tryptophan, and two l-tryptophan-derived esters in food (black sesame seed (Sesamum indicum L.) was selected in this case). The GO@SiO2 nanocomposite was prepared by one-pot aggregation in aqueous phase with sol-gel technique. The structure and morphology of the GO@SiO2 were characterized by scanning electron microscopy, transmission electron microscopy, Fourier transform-infrared spectroscopy, and X-ray diffraction. The extraction conditions of dSPE including the ratio of material to liquid, adsorption and desorption time, desorption temperature, and desorption solvents were investigated, respectively. The detection limits of the developed method for the analysis of melatonin, l-tryptophan, l-tryptophan methyl ester, and l-tryptophan ethyl ester were achieved below 0.1 μg mL−1. The established method was successfully applied to the analysis of the target analytes in black sesame seed, which provided a simple, low-cost, and sensitive approach for the determination of trace compounds in complex samples.

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References

  • Arnao MB, Ruiz JH (2015) Functions of melatonin in plants: a review. J Pineal Res 59:133–150

    Article  CAS  PubMed  Google Scholar 

  • Calvo JR, Yanes CG, Maldonado MD (2013) The role of melatonin in the cells of the innate immunity: a review. J Pineal Res 55:103–120

    Article  CAS  PubMed  Google Scholar 

  • Cruz EF, Álvarez-Fernández MA, Valero E, Troncoso AM, García-Parrilla MC (2016) Validation of an analytical method to determine melatonin and compounds related to L-tryptophan metabolism using UHPLC/HRMS. Food Anal Methods 9:3327–3336

    Article  Google Scholar 

  • Dreyer DR, Park SJ, Bielawski CW, Ruoff RS (2010) The chemistry of graphene oxide. Chem Soc Rev 39:228–240

    Article  CAS  PubMed  Google Scholar 

  • Dubbels R, Reiter RJ, Klenke E, Goebel A, Schnakenberg E, Ehlers C, Schiwara HW, Schloot W (1995) Melatonin in edible plants identified by radioimmunoassay and by high performance liquid chromatography-mass spectrometry. J Pineal Res 18:28–31

    Article  CAS  PubMed  Google Scholar 

  • García JJ, Pingarrón LL, Souza PA, Tres A, Escudero P, García-Gil FA, Tan DX, Reiter RJ, Ramírez JM, Bernal-Pérez M (2014) Protective effects of melatonin in reducing oxidative stress and in preserving the fluidity of biological membranes: a review. J Pineal Res 56:225–237

    Article  CAS  PubMed  Google Scholar 

  • Gomez F, Hernández IG, Cerutti S, Silva MF (2015a) Solid phase extraction/cyclodextrin-modified micellar electrokinetic chromatography for the analysis of melatonin and related indole compounds in plants. Microchem J 123:22–27

    Article  CAS  Google Scholar 

  • Gomez FJ, Martín A, Silva MF, Escarpa A (2015b) Microchip electrophoresis-single wall carbon nanotube press-transferred electrodes for fast and reliable electrochemical sensing of melatonin and its precursors. Electrophoresis 36:1880–1885

    Article  CAS  PubMed  Google Scholar 

  • Huang X, Mazza G (2011) Simultaneous analysis of serotonin, melatonin, piceid and resveratrol in fruits using liquid chromatography tandem mass spectrometry. J Chromatogr A 1218:3890–3899

    Article  CAS  PubMed  Google Scholar 

  • Hummers WS, Offeman RE (1958) Preparation of graphitic oxide. J Am Chem Soc 80:1339

    Article  CAS  Google Scholar 

  • Ishizaki A, Uemura A, Kataoka H (2017) A sensitive method to determine melatonin in saliva by automated online in-tube solid-phase microextraction coupled with stable isotope-dilution liquid chromatography-tandem mass spectrometry. Anal Methods 9:3134–3140

    Article  CAS  Google Scholar 

  • Kocadağlı T, Yılmaz C, Gökmen V (2014) Determination of melatonin and its isomer in foods by liquid chromatography tandem mass spectrometry. Food Chem 153:151–156

    Article  CAS  PubMed  Google Scholar 

  • Liu Q, Shi JB, Jiang GB (2012) Application of graphene in analytical sample preparation. Trac-Trend Anal Chem 37:1–11

    Article  CAS  Google Scholar 

  • Liu Q, Shi JB, Sun JT, Wang T, Zeng LX, Jiang GB (2011) Graphene and graphene oxide sheets supported on silica as versatile and high-performance adsorbents for solid-phase extraction. Angew Chem Int Ed 50:5913–5917

    Article  CAS  Google Scholar 

  • Mauriz JL, Collado PS, Veneroso C, Reiter RJ, Gallego JG (2013) A review of the molecular aspects of melatoninʼs anti-inflammatory actions: recent insights and new perspectives. J Pineal Res 54:1–14

    Article  CAS  PubMed  Google Scholar 

  • Meng JF, Shia TC, Song S, Zhang ZW, Fang YL (2017) Melatonin in grapes and grape-related foodstuffs: a review. Food Chem 231:185–191

    Article  CAS  PubMed  Google Scholar 

  • Murch SJ, Hall BA, Le CH, Saxena PK (2010) Changes in the levels of indoleamine phytochemicals during véraison and ripening of wine grapes. J Pineal Res 49:95–100

    CAS  PubMed  Google Scholar 

  • Novoselov KS, Geim AK, Morozov SV, Jiang D, Zhang Y, Dubonos SV, Grigorieva IV, Firsov AA (2004) Electric field effect in atomically thin carbon films. Science 306:666–669

    Article  CAS  PubMed  Google Scholar 

  • Poboży E, Michalski A, Brochocka JS, Trojanowicz M (2005) Determination of melatonin and its precursors and metabolites using capillary electrophoresis with UV and fluorometric detection. J Sep Sci 28:2165–2172

    Article  CAS  PubMed  Google Scholar 

  • Rao CNR, Sood AK, Subrahmanyam KS, Govindaraj A (2009) Graphene : the new two-dimensional nanomaterial. Angew Chem Int Ed 48:7752–7777

    Article  CAS  Google Scholar 

  • Reinholds I, Pugajeva I, Radenkovs V, Rjabova J, Bartkevics V (2016) Development and validation of new ultra-high-performance liquid chromatography–hybrid quadrupole-Orbitrap mass spectrometry method for determination of melatonin in fruits. J Chromatogr Sci 54:977–984

    Article  CAS  PubMed  Google Scholar 

  • Setyaningsih W, Palma M, Barroso CG (2012) A new microwave-assisted extraction method for melatonin determination in rice grains. J Cereal Sci 56:340–346

    Article  CAS  Google Scholar 

  • Setyaningsih W, Saputro IE, Barbero GF, Palma M, Barroso CG (2015) Determination of melatonin in rice (Oryza sativa) grains by pressurized liquid extraction. J Agric Food Chem 63:1107–1115

    Article  CAS  PubMed  Google Scholar 

  • Talebianpoor MS, Khodadoust S, Rozbehi A, Toori MA, Zoladl M, Ghaedi M, Mohammadi R, Hosseinzadeh AS (2014) Application of optimized dispersive liquid–liquid microextraction for determination of melatonin by HPLC–UV in plasma samples. J Chromatogr B 960:1–7

    Article  CAS  Google Scholar 

  • Tan DX, Zheng XD, Kong J, Manchester LC, Hardeland R, Kim SJ, Xu XY, Reiter RJ (2014) Fundamental issues related to the origin of melatonin and melatonin isomers during evolution: relation to their biological functions. Int J Mol Sci 15:15858–15890

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Tudela R, Agustí AR, Buxaderas S, Aumatell MR, Castellari M, Tamames EL (2016) Ultrahigh-performance liquid chromatography (UHPLC)−tandem mass spectrometry (MS/MS) quantification of nine target indoles in sparkling wines. J Agric Food Chem 64:4772–4776

    Article  CAS  PubMed  Google Scholar 

  • Wang AQ, Wei BP, Zhang Y, Wang YJ, Xu L, Lan K (2011) An ultra-high sensitive bioanalytical method for plasma melatonin by liquid chromatography–tandem mass spectrometry using water as calibration matrix. J Chromatogr B 879:2259–2264

    Article  CAS  Google Scholar 

  • Xiao R, Zhang XT, Zhang XN, Niu JH, Lu MH, Liu XH, Cai ZW (2017) Analysis of flavors and fragrances by HPLC with Fe3O4@GO magnetic nanocomposite as the adsorbent. Talanta 166:262–267

    Article  CAS  PubMed  Google Scholar 

  • Ye TT, Hao YH, Yu L, Shi HT, Reiter RJ, Feng YQ (2017) A simple, rapid method for determination of melatonin in plant tissues by UPLC coupled with high resolution Orbitrap mass spectrometry. Front Plant Sci 8:1–10

    Google Scholar 

  • Yin BJ, Li TT, Li Z, Dang T, He PL (2016) Determination of melatonin and its metabolites in biological fluids and eggs using high-performance liquid chromatography with fluorescence and quadrupole-Orbitrap high-resolution mass spectrometry. Food Anal Methods 9:1142–1149

    Article  Google Scholar 

  • Zhang XN, Niu JH, Zhang XT, Xiao R, Lu MH, Cai ZW (2017) Graphene oxide-SiO2 nanocomposite as the adsorbent for extraction and preconcentration of plant hormones for HPLC analysis. J Chromatogr B 1046:58–64

    Article  CAS  Google Scholar 

  • Zieliński H, Nowak DS, Wiczkowski W (2017) Determination of melatonin in bakery products using liquid chromatography coupled to tandem mass spectrometry (LC–MS/MS). Chem Pap 71:1083–1089

    Article  CAS  Google Scholar 

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Funding

Support by the National Nature Science Foundation of China (21477033), Program for Science & Technology Innovation Talents in Universities of Henan Province (17HASTIT003), Program for Excellent Youth Scholars in Higher Education of Henan Province (2014GGJS-024), and the Program for Development in Science and Technology of Henan Province (172102310608) is gratefully acknowledged.

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Correspondence to Minghua Lu.

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Jiahua Niu declares that she has no conflict of interest. Xiaoting Zhang declares that she has no conflict of interest. Peige Qin declares that she has no conflict of interest. Yixin Yang declares that she has no conflict of interest. Shufang Tian declares that she has no conflict of interest. Hui Yang declares that she has no conflict of interest. Minghua Lu declares that he has no conflict of interest.

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This article does not contain any studies with human participants or animals performed by any of the authors.

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Niu, J., Zhang, X., Qin, P. et al. Simultaneous Determination of Melatonin, l-Tryptophan, and two l-Tryptophan-Derived Esters in Food by HPLC with Graphene Oxide/SiO2 Nanocomposite as the Adsorbent. Food Anal. Methods 11, 2438–2446 (2018). https://doi.org/10.1007/s12161-018-1213-2

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  • DOI: https://doi.org/10.1007/s12161-018-1213-2

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