Generic placeholder image

Current Analytical Chemistry

Author(s): Òscar Vidal, Xavier Castilla, Núria Aliaga-Alcalde, Ana M. López-Periago, Concepción Domingo, Sonia Sentellas and Javier Saurina*

DOI: 10.2174/1573411014666180629125729

DownloadDownload PDF Flyer Cite As
Determination of Curcuminoids by Liquid Chromatography with Diode Array Detection: Application to the Characterization of Turmeric and Curry Samples

Page: [95 - 105] Pages: 11

  • * (Excluding Mailing and Handling)

Abstract

Background: A simple, rapid and efficient method for the determination of curcumin and other polyphenols in turmeric and curry samples was here developed. The method relied on sample extraction with methanol and extract analysis by liquid chromatography with diode array detection (HPLC-DAD).

Methods: The separation of components was carried out in reversed-phase mode using an elution gradient based on 0.1% (v/v) formic acid aqueous solution and acetonitrile as the components of the mobile phase. Chromatograms were recorded at 420 nm for specific monitoring of curcumin and related compounds.

Results: Extraction and separation conditions were optimized by experimental design and multicriteria response functions. Figures of merit were established under the selected experimental conditions. In general, repeatability of peak areas were better than 0.4%, detection limits were below 0.006 mg L-1 and quantitative recoveries expressed as a percentage were about 100 ± 2. The method was applied to quantify curcuminoids in commercial samples. It was found that apart from curcumin, demethoxycurcumin and bisdemethoxycurcumin, other related molecules also occurred in the samples. In this regard, a tentative elucidation of possible unknown curcuminoids was attempted by liquid chromatography coupled to mass spectrometry.

Conclusion: Differences in the compositional profiles among samples were encountered to be relevant, so that the resulting HPLC-DAD data was exploited for chemometric characterization of turmeric and curry samples. Samples were successfully discriminated according to matrix types, species varieties and origins.

Keywords: Curcumin determination, curcuminoids, experimental design, food sample characterization, liquid chromatography, principal component analysis.

Graphical Abstract

[1]
Maheshwari, R.K.; Singh, A.K.; Gaddipati, J.; Srimal, R.C. Multiple biological activities of curcumin: A short review. Life Sci., 2006, 78(18), 2081-2087.
[http://dx.doi.org/10.1016/j.lfs.2005.12.007] [PMID: 16413584]
[2]
Jurenka, J.S. Anti-inflammatory properties of curcumin, a major constituent of Curcuma longa: A review of preclinical and clinical research. Altern. Med. Rev., 2009, 14(2), 141-153.
[PMID: 19594223]
[3]
Zhou, H.; Beevers, C.S.; Huang, S. The targets of curcumin. Curr. Drug Targets, 2011, 12(3), 332-347.
[http://dx.doi.org/10.2174/138945011794815356] [PMID: 20955148]
[4]
Anand, P.; Thomas, S.G.; Kunnumakkara, A.B.; Sundaram, C.; Harikumar, K.B.; Sung, B.; Tharakan, S.T.; Misra, K.; Priyadarsini, I.K.; Rajasekharan, K.N.; Aggarwal, B.B. Biological activities of curcumin and its analogues (Congeners) made by man and Mother Nature. Biochem. Pharmacol., 2008, 76(11), 1590-1611.
[http://dx.doi.org/10.1016/j.bcp.2008.08.008] [PMID: 18775680]
[5]
Marchiani, A.; Rozzo, C.; Fadda, A.; Delogu, G.; Ruzza, P. Curcumin and curcumin-like molecules: From spice to drugs. Curr. Med. Chem., 2014, 21(2), 204-222.
[http://dx.doi.org/10.2174/092986732102131206115810] [PMID: 23590716]
[6]
Goel, A.; Kunnumakkara, A.B.; Aggarwal, B.B. Curcumin as “Curecumin”: from kitchen to clinic. Biochem. Pharmacol., 2008, 75(4), 787-809.
[http://dx.doi.org/10.1016/j.bcp.2007.08.016] [PMID: 17900536]
[7]
Tayyem, R.F.; Heath, D.D.; Al-Delaimy, W.K.; Rock, C.L. Curcumin content of turmeric and curry powders. Nutr. Cancer, 2006, 55(2), 126-131.
[http://dx.doi.org/10.1207/s15327914nc5502_2] [PMID: 17044766]
[8]
Chanin, N.; Saw, S.; Abdul, H.; Veda, P.; Apilak, W.; Napat, S.; Kakanand, S.; Chartchalerm, I.N.A.; Supaluk, P.; Virapong, P. Elucidating the structure-activity relationship of curcumin and its biological activities.Curcumin: Synthesis, Emerging Role in Pain Management and Health Implications; Pouliquen, D.L., Ed.; Nova Science Publisher: NY, 2014, pp. 49-86.
[9]
Priyadarsini, K.I. The chemistry of curcumin: From extraction to therapeutic agent. Molecules, 2014, 19(12), 20091-20112.
[http://dx.doi.org/10.3390/molecules191220091] [PMID: 25470276]
[10]
Kim, Y.J.; Lee, H.J.; Shin, Y. Optimization and validation of high-performance liquid chromatography method for individual curcuminoids in turmeric by heat-refluxed extraction. J. Agric. Food Chem., 2013, 61(46), 10911-10918.
[http://dx.doi.org/10.1021/jf402483c] [PMID: 24164304]
[11]
Ali, I.; Haque, A.; Saleem, K. Separation and identification of curcuminoids in turmeric powder by HPLC using phenyl column. Anal. Methods, 2014, 6, 2526-2536.
[http://dx.doi.org/10.1039/C3AY41987H]
[12]
Inoue, K.; Hamasaki, S.; Yoshimura, Y.; Yamada, M.; Nakamura, M.; Ito, Y.; Nakazawa, H. Validation of LC/electrospray-MS for determination of major curcuminoids in foods. J. Liq. Chromatogr. Relat. Technol., 2003, 26, 53-62.
[http://dx.doi.org/10.1081/JLC-120017152]
[13]
Anubala, S.; Sekar, R.; Nagaiah, K. Development and validation of an analytical method for the separation and determination of major bioactive curcuminoids in Curcuma longa rhizomes and herbal products using non-aqueous capillary electrophoresis. Talanta, 2014, 123, 10-17.
[http://dx.doi.org/10.1016/j.talanta.2014.01.017] [PMID: 24725858]
[14]
Osorio-Tobon, J.F.; Meireles, M.A.A. Recent applications of pressurized fluid extraction: curcuminoids extraction with pressurized liquids. Food Public Health, 2013, 3, 289-303.
[http://dx.doi.org/10.5923/j.fph.20130306.05]
[15]
Mudge, E.; Chan, M.; Venkataraman, S.; Brown, P.N. Curcuminoids in turmeric roots and supplements: Method optimization and validation. Food Anal. Methods, 2016, 9, 1428-1435.
[http://dx.doi.org/10.1007/s12161-015-0326-0]
[16]
Khurana, A.; Ho, C.T. High-performance liquid-chromatographic analysis of curcuminoids and their photo-oxidative decomposition compounds in curcuma longa. J. Liq. Chromatogr., 1988, 11, 2295-2304.
[http://dx.doi.org/10.1080/01483918808067200]
[17]
Chin-Chen, M.L.; Carda-Broch, S.; Bose, D.; Esteve-Romero, J. Direct injection and determination of the active principles of spices using micellar liquid chromatography. Food Chem., 2010, 120, 915-920.
[http://dx.doi.org/10.1016/j.foodchem.2009.11.003]
[18]
Malasoni, R.; Srivastava, A.; Pandey, R.R.; Srivastava, P.K.; Dwivedi, A.K. Development and validation of improved HPLC method for the Quantitative determination of Curcuminoids in Herbal Medicament. J. Sci. Ind. Res. (India), 2013, 72, 88-91.
[19]
Osorio-Tobón, J.F.; Carvalho, P.I.N.; Barbero, G.F.; Nogueira, G.C.; Rostagno, M.A.; Meireles, M.A.D. Fast analysis of curcuminoids from turmeric (Curcuma longa L.) by high-performance liquid chromatography using a fused-core column. Food Chem., 2016, 200, 167-174.
[http://dx.doi.org/10.1016/j.foodchem.2016.01.021] [PMID: 26830575]
[20]
Ashraf, K.; Mujeeb, M.; Ahmad, A.; Ahmad, N.; Amir, M. Determination of curcuminoids in Curcuma longa Linn. by UPLC/Q-TOF-MS: An application in turmeric cultivation. J. Chromatogr. Sci., 2015, 53(8), 1346-1352.
[http://dx.doi.org/10.1093/chromsci/bmv023] [PMID: 25838167]
[21]
Kalaycıoğlu, Z.; Hashemi, P.; Günaydın, K.; Erim, F.B. The sensitive capillary electrophoretic-LIF method for simultaneous determination of curcuminoids in turmeric by enhancing fluorescence intensities of molecules upon inclusion into (2-hydroxypropyl)-β-cyclodextrin. Electrophoresis, 2015, 36(20), 2516-2521.
[http://dx.doi.org/10.1002/elps.201500253] [PMID: 26178140]
[22]
Anubala, S.; Sekar, R.; Nagaiah, K. Determination of curcuminoids and their degradation products in turmeric (curcuma longa) rhizome herbal products by non- aqueous capillary electrophoresis with photodiode array detection. Food Anal. Methods, 2016, 9, 2567-2578.
[http://dx.doi.org/10.1007/s12161-016-0438-1]
[23]
Li, F.; Liu, R.; Yang, F.Q.; Xiao, W.; Chen, C.; Xia, Z.N. Determination of three curcuminoids in Curcuma longa by microemulsion electrokinetic chromatography with protective effects on the analytes. Anal. Methods, 2015, 6, 2566-2571.
[http://dx.doi.org/10.1039/C3AY42106F]
[24]
Nhujak, T.; Saisuwan, W.; Srisa-art, M.; Petsom, A. Microemulsion electrokinetic chromatography for separation and analysis of curcuminoids in turmeric samples. J. Sep. Sci., 2006, 29(5), 666-676.
[http://dx.doi.org/10.1002/jssc.200500333] [PMID: 16605086]
[25]
Lucci, P.; Saurina, J.; Nunez, O. Trends in LC-MS and LC-HRMS analysis and characterization of polyphenols in food. Trends Analyt. Chem., 2017, 88, 1-24.
[http://dx.doi.org/10.1016/j.trac.2016.12.006]
[26]
Sentellas, S.; Núñez, Ó.; Saurina, J. Recent Advances in the determination of biogenic amines in food samples by (U)HPLC. J. Agric. Food Chem., 2016, 64(11), 7667-7678.
[http://dx.doi.org/10.1021/acs.jafc.6b02789] [PMID: 27689967]
[27]
Saurina, J. Characterization of wines using compositional profiles and chemometrics. Trends Analyt. Chem., 2010, 29, 234-245.
[http://dx.doi.org/10.1016/j.trac.2009.11.008]
[28]
Kulyal, P.; Kuchibhatla, L.N.; Maheshwari, K.U.; Babu, K.N. Tetali. S.D.; Raghavendra, A.S. Highly sensitive HPLC method for estimation of total or individual curcuminoids in Curcuma cultivars and commercial turmeric powders. Curr. Sci., 2016, 111, 1816-1824.
[http://dx.doi.org/10.18520/cs/v111/i11/1816-1824]
[29]
Ma, X.; Gang, D.R. Metabolic profiling of turmeric (Curcuma longa L.) plants derived from in vitro micropropagation and conventional greenhouse cultivation. J. Agric. Food Chem., 2006, 54(25), 9573-9583.
[http://dx.doi.org/10.1021/jf061658k] [PMID: 17147448]
[30]
Lee, J.; Jung, Y.; Shin, J.H.; Kim, H.K.; Moon, B.C.; Ryu, D.H.; Hwang, G.S. Secondary metabolite profiling of Curcuma species grown at different locations using GC/TOF and UPLC/Q-TOF MS. Molecules, 2014, 19(7), 9535-9551.
[http://dx.doi.org/10.3390/molecules19079535] [PMID: 25000465]
[31]
Ni, Y.N.; Mei, M.H.; Kokot, S. Resolution of high performance liquid chromatographic fingerprints of rhizoma curcumae by application of chemometrics. J. Liq. Chromatogr. Relat. Technol., 2011, 34, 1952-1964.
[http://dx.doi.org/10.1080/10826076.2011.582215]
[32]
Rohaeti, E.; Rafi, M.; Syafitri, U.D.; Heryanto, R. Fourier transform infrared spectroscopy combined with chemometrics for discrimination of Curcuma longa, Curcuma xanthorrhiza and Zingiber cassumunar. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2015, 137, 1244-1249.
[http://dx.doi.org/10.1016/j.saa.2014.08.139] [PMID: 25305617]
[33]
Wise, B.; Gallager, N.B. PLS_Toolbox for use with MATLAB, version 2.0, Eigenvector Research Inc; Mason: WA, USA, 1992.
[34]
Puigventos, L.; Nunez, O.; Saurina, J. HPLC Fingerprints for the authentication of cranberry-based products based on multivariate calibration approaches. Curr. Anal. Chem., 2017, 13, 256-261.
[http://dx.doi.org/10.2174/1573411012666160216220526]
[35]
Li, W.; Wang, S.; Feng, J.; Xiao, Y.; Xue, X.; Zhang, H.; Wang, Y.; Liang, X. Structure elucidation and NMR assignments for curcuminoids from the rhizomes of Curcuma longa. Magn. Reson. Chem., 2009, 47(10), 902-908.
[http://dx.doi.org/10.1002/mrc.2478] [PMID: 19569074]