Abstract
This work proposes a fluorescent probe based on CdTe quantum dots (QDs) for the determination of resveratrol in wine samples. The synthesis of cysteamine (CA) capped CdTe QD was carried out in a one-pot eco-friendly process, resorting to the electrochemical reduction of metallic tellurium powder in a graphite macroelectrode (cavity cell). The reduced species of tellurium (Te2− and Te22−) migrated to an intermediate compartment of the electrochemical cell and in the presence of a cadmium salt and organic stabilizing agent (CA), forming the colloidal dispersion of CdTe in a single step. Under optimum synthesis conditions, the fluorescence intensity of the prepared nanoparticles varied linearly with the resveratrol concentration in the range from 3.25 to 75 μg L−1 (R2 = 0.9984), with a detection limit of 0.97 μg L−1 and RSD of 3.7% (5.0 μg L−1 resveratrol, n = 10). The method was successfully applied to the resveratrol determination in wines, with recoveries from 97.8 to 112.4%. Student’s t test was applied and no statistically significant difference was observed between the two methods (HPLC and proposed), with a confidence level of 95% (ttabulated = 2.45 and tcalculated = 0.38). The resveratrol determination method, by using CdTe-CA QDs as fluorescence probe, was simple, rapid, inexpensive, and sensitive.
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References
Arce L, Tena MT, Rios A (1998) Determination of trans-resveratrol and other polyphenols in wines by a continuous flow sample clean-up system followed by capillary electrophoresis separation. Anal Chim Acta 359:27–38
Areias MCC, Navarro M, Bieber LW, Diniz FB, Léonel E, Vivier CC, Nedelec JY (2008) A novel electrosynthesis cell with a compressed graphite powder cathode and minimal organic solvent content: application to the Reformatsky reaction. Electrochim Acta 53:6477–6483
Belmiro TMC, Pereira CF, Paim APS (2017) Red wines from South America: content of phenolic compound and chemometric distinction by origin. Microchem J 133:114–120
Biju V, Itoh T, Anas A, Sujith A, Ishikawa M (2008) Semiconductor quantum dots and metal nanoparticles: syntheses, optical properties, and biological applications. Anal Bioanal Chem 391:2469–2495
Burns J, Gardner PT, O’Neil J, Crawford S, Morecroft I, McPhail DB, Lister C, Matthews D, MacLean MR, Lean MEJ, Duthie GG, Alan C (2000) Relationship among antioxidant activity, vasodilation capacity, and phenolic content of red wines. J Agric Food Chem 48:220–230
Cacho JI, Campillo N, Vinas P, Hernández-Córdoba M (2013) Stir bar sorptive extraction with gas chromatography-mass spectrometry for the determination of resveratrol, piceatannol and oxyresveratrol isomers in wines. J Chromatogr A 1315:21–27
Cai K, Yang R, Wang Y, Yu X, Liu J (2013) Super fast detection of latent fingerprints with water soluble CdTe quantum dots. Forensic Sci Int 226:240–243
Costa-Fernández JM, Pereiro R, Sanz-Medel A (2006) The use of luminescent quantum dots for optical sensing. TrAC Trends Anal Chem 25:207–218
Drbohlavova J, Adam V, Kizek R, Hubalek J (2009) Quantum dots—characterization, preparation and usage in biological systems. Int J Mol Sci 10:656–673
Freitas DV, Dias JMM, Passos SGB, De Souza GCS, Teixeira Neto E, Navarro M (2014) Electrochemical synthesis of TGA-capped CdTe and CdSe quantum dots. Green Chem 16:3247–3254
Galeano-Díaz T, Durán-Merás I, Airado-Rodríguez D (2007a) Determination of resveratrol in wine by photochemically induced second-derivative fluorescence coupled with liquid-liquid extraction. Anal Bioanal Chem 387:1999–2007
Galeano-Diaz T, Durán-Merás I, Airado-Rodriguez D (2007b) Isocratic chromatography of resveratrol and piceid after previous generation of fluorescent photoproducts: wine analysis without sample preparation. J Sep Sci 30:3110–3119
Gan T, Zhao N, Yin G, Tu M, Liu J, Liu W (2017) Mercaptopropionic acid-capped Mn-doped ZnS quantum dots as a probe for selective room-temperature phosphorescence detection of Pb2+ in water. New J Chem 41:13425–13434
Garcia-Cortes M, Fernandez-Arguelles MT, Costa-Fernandez JM (2017) Sensitive prostate specific antigen quantification using dihydrolipoic acid surface functionalized phosphorescent quantum dots. Anal Chim Acta 987:118–126
Gocan S (2009) Analysis of stilbenes in wine by HPLC: recent approaches. J Liq Chromatogr Relat Technol 32:1598–1643
Godoy-Caballero P, Airado-Rodríguez D, Durán-Merás I, Galeano-Díaz T (2010) Sensitized synchronous fluorimetric determination of trans-resveratrol and trans-piceid in red wine based on their immobilization on nylon membranes. Talanta 82:1733–1741
Han J, Bu X, Zhou D, Zhang H, Yang B (2014) Discriminating Cr(III) and Cr(VI) using aqueous CdTe quantum dots with various surface ligands. RSC Adv 4:32946–32952
Jackson RS (2008) Wine science. Principles and applications. Elsevier, USA ISBN: 978-0-12-373646-8
Koc MA, Raja SN, Hanson LA, Nguyen SC, Borys NJ, Powers AS, Wu S, Takano K, Swabeck JK, Olshansky JH, LinL RRO, Alivisatos AP (2017) Characterizing photon reabsorption in quantum dot-polymer composites for use as displacement sensors. ACS Nano 11:2075–2084
Kolouchová-Hanzlíková I, Melzoch K, Filip V, Smidrkal J (2004) Rapid method for resveratrol determination by HPLC with electrochemical and UV detections in wines. J Food Chem 87:151–158
Kuang R, Kuang X, Pan S, Zheng X, Duan J, Duan Y (2010) Synthesis of cysteamine-coated CdTe quantum dots for the detection of bisphenol A. Microchim Acta 169:109–115
Lamuela-Raventos RM, Romero-Perez AI, Waterhouse AL, Torre-Boronat MC (1995) Direct HPLC analysis of cis- and trans-resveratrol and piceid isomers in Spanish red Vitis vinifera wines. J Agric Food Chem 43:281–283
Li J, Li X, Yang R, Qu L, Harrington PB (2013) Sensitive electrochemical chlorophenols sensor based on nanocomposite of ZnSe quantum dots and cetyltrimethylammonium bromide. Anal Chim Acta 804:76–83
Lima AS, Rodrigues SSM, Korn MGA, Ribeiro DSM, Santos JLM, Teixeira LSG (2014) Determination of copper in biodiesel samples using CdTe-GSH quantum dots as photoluminescence probes. Microchem J 117:144–148
Liu X, Teng Z, Zhang Y, Huan M, Zhou S (2010) Bioavailability and safety study of resveratrol 500 mg tablets in healthy male and female volunteers. Anal Lett 43:557–569
Lopez R, Dugo P, Mondello L (2007) Determination of trans-resveratrol in wine by micro-HPLC with fluorescence detection. J Sep Sci 30:669–672
López-Nicolás JM, García-Carmona F (2008) Rapid, simple and sensitive determination of the apparent formation constants of trans-resveratrol complexes with natural cyclodextrins in aqueous medium using HPLC. Food Chem 109:868–875
Luan T, Li G, Zhang Z (2000) Gas-phase post derivatization following solid-phase microextraction for rapid determination of trans-resveratrol in wine by gas chromatography-mass spectrometry. Anal Chim Acta 404(424):19–25
Molina-García L, Ruiz-Medina A, Fernández-de Córdova ML (2011) An automatic optosensing device for the simultaneous determination of resveratrol and piceid in wines. Anal Chim Acta 689:226–233
Montes M, García-López M, Rodríguez I, Cela R (2010) Mixed-mode solid-phase extraction followed by acetylation and gas chromatography mass spectrometry for the reliable determination of trans-resveratrol in wine samples. Anal Chim Acta 673:47–53
Nemcová L, Zima J, Bareka J, Janovská D (2011) Determination of resveratrol in grains, hulls and leaves of common and tartary buckwheat by HPLC with electrochemical detection at carbon paste electrode. Food Chem 126:374–378
Nour V, Trandafir I, Muntean C (2012) Ultraviolet irradiation of trans-resveratrol and HPLC determination of trans-resveratrol and cis-resveratrol in Romanian red wines. J Chromatogr Sci 50:920–927
Paim APS, Rodrigues SSM, Ribeiro DSM, Souza GCS, Santos JLM, Araujo ANCG, Amorim AN, Teixeira-Neto E, Silva VL, Montenegro MCBSM (2017) Fluorescence probe for mercury(II) based on the aqueous synthesis of CdTe quantum dots stabilized with 2-mercaptoetanosulfonate. New J Chem 41:3265–3272
Passos SGB, Freitas DV, Dias JMM, Teixeira-Neto E, Navarro M (2016) One-pot electrochemical synthesis of CdTe quantum dots in cavity cell. Electrochim Acta 190:689–694
Penumathsa SV, Maulik N (2009) Resveratrol: a promising agent in promoting cardioprotection against coronary heart disease. Can J Physiol Pharmacol 87:275–286
Pezet R, Pont V, Cuenat P (1994) Method to determine resveratrol and pterostilbene in grape berries and wines using high-performance liquid chromatography and highly sensitive fluorimetric detection. J Choromatogr A 663:191–197
Rodrigues SSM, Ribeiro DSM, Soares JX, Passos MLC, Saraiva MLMFS, Santos JLM (2017) Application of nanocrystalline CdTe quantum dots in chemical analysis: implementation of chemo-sensing schemes based on analyte triggered photoluminescence modulation. Coord Chem Rev 330:127–143
Soto ME, Bernal J, Martín MT, Higes M, Bernal JL, Nozal MJ (2012) Liquid chromatographic determination of resveratrol and piceid isomers in honey. Food Anal Methods 5:162–171
Souza GCS, Santana EEA, Silva PAB, Freitas DV, Navarro M, Paim APS, Lavorante AF (2015) Employment of electrochemically synthesized TGA–CdSe quantum dots for Cr3+ determination in vitamin supplements. Talanta 144:986–991
Souza GCS, Ribeiro DSM, Rodrigues SSM, Paim APS, Lavorante AF, Silva VL, Santos JLM, Araujo NA, Montenegro MCBSM (2016) Clean photoinduced generation of free reactive oxygen species by silica films embedding MPA-CdTe quantum dots. RSC Adv 6:8563–8571
Yu WW, Qu L, Guo W, Peng X (2003) Experimental determination of the extinction coefficient of CdTe, CdSe, and CdS nanocrystals. Chem Mater 15:2854–2860
Zhang L, Xu C, Li B (2009) Simple and sensitive detection method for chromium(VI)in water using glutathione capped CdTe quantum dots as fluorescent probes. Microchim Acta 166:61–68
Zhang Q, Qian D, Hai-Bo H, An Y, Wang T (2013) Determination of trans-resveratrol in grape seed by coupling liquid extraction with micellar electrokinetic chromatography. Anal Methods 5:3418–3421
Acknowledgements
The authors acknowledge LNNano-CNPEM (Campinas, Brazil) for the use of the TEM facility. Research fellowships and scholarship granted by CNPq and CAPES are also gratefully acknowledged. The English version was revised by Sidney Pratt, Canadian, BA, MAT (The Johns Hopkins University), RSAdip (TEFL) (Cambridge University).
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Financial support by CAPES (Projeto PVE 093/2012), FACEPE (APQ-0557-1.06/15), and FACEPE/NUQAAPE (APQ-0346-1.06/14).
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Natália S. M. Ramos declares that she has no conflict of interest. Denilson V. Freitas declares that he has no conflict of interest. Gustavo C. S. de Souza declares that he has no conflict of interest. Tailândia M. C. Belmiro declares that she has no conflict of interest. Erico Teixeira-Neto declares that he has no conflict of interest. Marcelo Navarro declares that he has no conflict of interest. André F. Lavorante declares that he has no conflict of interest. Maria Conceição B. S. M. Montenegro declares that she has no conflict of interest. Ana Paula S. Paim declares that she has no conflict of interest.
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Ramos, N.S.M., Freitas, D.V., de Souza, G.C.S. et al. Cysteamine-CdTe Quantum Dots Electrochemically Synthesized as Fluorescence Probe for Resveratrol. Food Anal. Methods 11, 3371–3379 (2018). https://doi.org/10.1007/s12161-018-1305-z
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DOI: https://doi.org/10.1007/s12161-018-1305-z