Baking; Correlation analysis; DDMP; HS-SPME-GC-MS/MS; Red jujube; Biotechnology; Food Science
Abstract :
[en] Baked red jujube is a common food ingredient used to enrich the nutritional value and enhance the aroma. DDMP (2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one) with intense bitterness and potential toxicity may be present in several baked red jujube-based products but there are no well-defined methods to measure it quickly, sensitively, and accurately. Headspace solid-phase microextraction with gas chromatography-tandem mass spectrometry (HS-SPME-GC-MS/MS) was applied for the analysis of DDMP. The standard curve was linear between the concentrations of 0.01 and 100 μg/mL, with a limit of detection at 0.1 ng/g that below the sensory threshold of DDMP (2.06 μg/g). Five cultivars of baked red jujubes from China were evaluated with the method for DDMP content (4.55–46.50 μg/g). The results indicated that jujube cultivars with a higher molar ratio of proline to glucose, lower moisture content, and stronger ability to resist water stress should be avoided from baking to modulate the formation of DDMP.
Disciplines :
Chemistry Food science
Author, co-author :
Qiao, Yening ; Université de Liège - ULiège > TERRA Research Centre ; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences (CAAS)/ Key Laboratory of Agro-Products Processing, Ministry of Agriculture and Rural Affairs, Beijing, China
Bi, Jinfeng; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences (CAAS)/ Key Laboratory of Agro-Products Processing, Ministry of Agriculture and Rural Affairs, Beijing, China
Chen, Qinqin; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences (CAAS)/ Key Laboratory of Agro-Products Processing, Ministry of Agriculture and Rural Affairs, Beijing, China
Wu, Xinye ; Université de Liège - ULiège > TERRA Research Centre ; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences (CAAS)/ Key Laboratory of Agro-Products Processing, Ministry of Agriculture and Rural Affairs, Beijing, China
Jin, Xinwen; Institute of Agro-products Processing Science and Technology, XinJiang Academy of Agricultural and Reclamation Science, Shihezi, China
Gou, Min ; Université de Liège - ULiège > TERRA Research Centre ; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences (CAAS)/ Key Laboratory of Agro-Products Processing, Ministry of Agriculture and Rural Affairs, Beijing, China
Yang, Xinrui; Institute of Food Science and Technology, Chinese Academy of Agricultural Sciences (CAAS)/ Key Laboratory of Agro-Products Processing, Ministry of Agriculture and Rural Affairs, Beijing, China
Purcaro, Giorgia ; Université de Liège - ULiège > TERRA Research Centre > Chimie des agro-biosystèmes
Language :
English
Title :
Rapid and sensitive quantitation of DDMP (2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one) in baked red jujubes by HS-SPME-GC-MS/MS
This work was supported by the National Natural Science Foundation of China [ 31801564 ]; Financial Science and Technology Project of Xinjiang production and construction Corps [ 2020CB008 ]; Science and Technology Project in Key of Xinjiang production and construction Corps [ 2019AB024 ]; and Agricultural Science and Technology Innovation Project [ CAAS-ASTIP-2020-IFST-04 ].
Armorini, S., Yeatts, J., Mullen, K., Mason, S., Mehmeti, E., Anderson, K., Washburn, S., Baynes, R., Development of a HS-SPME-GC-MS/MS method for the quantitation of thymol and carvacrol in bovine matrices and to determine residue depletion in milk and tissues. Journal of Agricultural and Food Chemistry 64:41 (2016), 7856–7865, 10.1021/acs.jafc.6b02899.
Beppu, Y., Komura, H., Izumo, T., Horii, Y., Shen, J., Tanida, M., Nakashima, T., Tsuruoka, N., Nagai, K., Identificaton of 2,3-dihydro-3,5-dihydroxy-6-methyl-4-H-pyran-4-one isolated from Lactobacillus pentosus strain S-PT84 culture supernatants as a compound that stimulates autonomic nerve activities in rats. Journal of Agricultural and Food Chemistry 60:44 (2021), 11044–11049, 10.1021/jf302355e.
Bin, Q., Peterson, D.G., Identification of bitter compounds in whole wheat bread crumb. Food Chemistry 203 (2016), 8–15, 10.1016/j.foodchem.2016.01.116.
Cechovska, L., Cejpek, K., Konecny, M., Velisek, J., On the role of 2,3-dihydro-3,5-dihydroxy-6-methyl-(4H)-pyran-4-one in antioxidant capacity of prunes. European Food Research and Technology 233:3 (2011), 367–376, 10.1007/s00217-011-1527-4.
Cho, I., Kim, S., Choi, H., Kim, Y., Characterization of aroma-active compounds in raw and cooked pine-mushrooms (Tricholoma matsutake Sing.). Journal of Agricultural and Food Chemistry 54 (2006), 6332–6335, 10.1021/jf060824l.
European Commission Directorate-General for Health and Food Safety (SANTE). Guidance document on analytical quality control and method validation procedures for pesticides residues analysis in food and feed. Retrieved from https://www.eurl-pesticides.eu, 2017. (Accessed 30 December 2021)
Evers, D., Lefevre, I., Legay, S., Lamoureux, D., Hausman, J.F., Gutierrez Rosales, R.O., Tincopa Marca, T.R., Hoffmann, L., Bonierbale, M., Schafleitner, R., Identification of drought-responsive compounds in potato through a combined transcriptomic and targeted metabolite approach. Journal of Experimental Botany 61 (2010), 2327–2343, 10.1093/jxb/erq060.
Feng, C., Wang, B., Zhao, A., Wei, L., Shao, Y., Wang, Y., Zhang, F., Quality characteristics and antioxidant activities of goat milk yogurt with added jujube pulp. Food Chemistry 277 (2019), 238–245, 10.1016/j.foodchem.2018.10.104.
Furlan, A.L., Bianucci, E., Giordano, W., Becker, D.F., Proline metabolic dynamics and implications in drought tolerance of peanut plants. Plant Physiology and Biochemistry 151 (2020), 566–578, 10.1016/j.plaphy.2020.04.010.
Gao, Q., Wu, C., Wang, M., The jujube (Ziziphus jujuba Mill.) fruit: A review of current knowledge of fruit composition and health benefits. Journal of Agricultural and Food Chemistry 61:14 (2013), 3351–3363, 10.1021/jf4007032.
Gbaguidi, F., Accrombessi, G., Moudachirou, M., Quetin-Leclercq, J., HPLC quantification of two isomeric triterpenic acids isolated from Mitracarpus scaber and antimicrobial activity on Dermatophilus Congolensis. Journal of Pharmaceutical and Biomedical Analysis 39 (2005), 990–995, 10.1016/j.jpba.2005.05.030.
Harischandra, N.R., Pallavi, M.S., Bheemanna, M., PavanKumar, K., Chandra Sekhara Reddy, V., Udaykumar, N.R., Paramasivam, M., Yadav, S., Simultaneous determination of 79 pesticides in pigeonpea grains using GC-MS/MS and LC-MS/MS. Food Chemistry, 347, 2021, 10.1016/j.foodchem.2020.128986 Article 128986.
Hassine, A.B., Ghanem, M.E., Bouzid, S., Lutts, S., An inland and a coastal population of the Mediterranean xero-halophyte species Atriplex halimus L. differ in their ability to accumulate proline and glycinebetaine in response to salinity and water stress. Journal of Experimental Botany 59 (2008), 1315–1326, 10.1093/jxb/ern040.
Hiramoto, K., Nasuhara, A., Michikoshi, K., Kato, T., Kikugawa, K., DNA strand-breaking activity and mutagenicity of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP), a Maillard reaction product of glucose and glycine. Mutation Research: Reviews in Mutation Research 395:1 (1997), 47–56, 10.1016/S1383-5718(97)00141-1.
Hopfer, H., Jodari, F., Negre-Zakharov, F., Wylie, P.L., Ebeler, S., HS-SPME-GC-MS/MS method for the rapid and sensitive quantitation of 2-acetyl-1-pyrroline in single rice kernels. Journal of Agricultural and Food Chemistry 64 (2016), 4114–4120, 10.1021/acs.jafc.6b00703.
Hwang, I.G., Kim, H.Y., Woo, K.S., Lee, S.H., Lee, J., Jeong, H.S., Isolation and identification of the antioxidant DDMP from heated pear (Pyrus pyrifolia Nakai). Preventive Nutrition and Food Science 18:1 (2013), 76–79, 10.3746/pnf.2013.18.1.076.
Jung, O., In, G., Tae, M., Bang, Y., Ung, S., Heon, S., Young, W., Dae, J., Jin, T., Anti-proliferate and pro-apoptotic effects of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyranone through inactivation of NF-κB in human colon cancer cells. Archives of Pharmacal Research 30:11 (2007), 1455–1463, 10.1007/BF02977371.
Kalogeropoulos, N., Chiou, A., Ioannou, M., Karathanos, V.T., Hassapidou, M., Andrikopoulos, N.K., Nutritional evaluation and bioactive microconstituents (phytosterols, tocopherols, polyphenols, triterpenic acids) in cooked dry legumes usually consumed in the Mediterranean countries. Food Chemistry 121 (2010), 682–690, 10.1016/j.foodchem.2010.01.005.
Kanzler, C., Haase, P., Schestkowa, H., Kroh, L., Antioxidant properties of heterocyclic intermediates of the Maillard reaction and structural related compounds. Journal of Agricultural and Food Chemistry 64:41 (2016), 7829–7837, 10.1021/acs.jafc.6b03398.
Kim, M., Baltes, W., On the role of 2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one in the maillard reaction. Journal of Agricultural and Food Chemistry 44:1 (1996), 282–289, 10.1021/jf950208h.
Kind, T., Tsugawa, H., Cajka, T., Ma, Y., Lai, Z., Mehta, S.S., Wohlgemuth, G., Barupal, D., Showalter, M.R., Arita, M., Fiehn, O., Identification of small molecules using accurate mass MS/MS search. Mass Spectrometry Reviews 37:4 (2017), 513–532, 10.1002/mas.21535.
Kumar, N., Kumawat, S., Khatri, P., Singla, P., Tandon, G., Bhatt, V., Shinde, S., Patil, G., Sonah, H., Deshmukh, R., Understanding aquaporin transport system in highly stress-tolerant and medicinal plant species jujube (Ziziphus jujuba Mill.). Journal of Biotechnology 324 (2020), 103–111, 10.1016/j.jbiotec.2020.09.026.
Li, J., Fan, L., Ding, S., Ding, X., Nutritional composition of five cultivars of Chinese jujube. Food Chemistry 103 (2007), 454–460, 10.1016/j.foodchem.2006.08.016.
Li, H., Tang, X.Y., Wu, C.J., Yu, S.J., Formation of 2,3-dihydro-3,5-Dihydroxy-6-Methyl-4(H)-Pyran-4-One (DDMP) in glucose-amino acids Maillard reaction by dry-heating in comparison to wet-heating. LWT-Food Science and Technology 105 (2019), 156–163, 10.1016/j.lwt.2019.02.015.
Li, H., Wu, C.J., Tang, X.Y., Yu, S.J., Insights into the regulation effects of certain phenolic acids on the 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one (DDMP) formation in micro-aqueous glucose-proline system. Journal of Agricultural and Food Chemistry 67:32 (2019), 9050–9059, 10.1021/acs.jafc.9b01182.
Li, H., Zhang, W.C., Tang, X.Y., Wu, C.J., Zhao, Z.Q., Identification of bitter-taste compounds in class-iii caramel colors. Flavour and Fragrance Journal 36:3 (2021), 404–411, 10.1002/ffj.3652.
Lucie, Č., Karel, C., Michae, K., Jan, V., On the role of 2,3-dihydro-3,5-dihydroxy-6-methyl-(4H)-pyran-4-one in antioxidant capacity of prunes. European Food Research and Technology 233:3 (2011), 367–376, 10.1007/s00217-011-1527-4.
Nishibori, S., Kawakishi, S., Formation of 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one from fructose and β-alanine under conditions used for baking. Journal of Agricultural and Food Chemistry 42 (1994), 1080–1084, 10.1021/jf00041a006.
Pereira, L.L., Guarçoni, R.C., Pinheiro, P.F., Osório, V.M., Pinheiro, C.A., Moreira, T.R., Ten, C., New propositions about coffee wet processing: Chemical and sensory perspectives. Food Chemistry, 25(310), 2020, 10.1016/j.foodchem.2019.125943 Article 125943.
Ranganayakulu, G.S., Sudhakar, C., Reddy, P.S., Effect of water stress on proline metabolism and leaf relative water content in two high yielding genotypes of groundnut (Arachis hypogaea L.) with contrasting drought tolerance. Journal of Experimental Biology and Agricultural Sciences 3:1 (2015), 97–103 http://www.jebas.org/00300120022015/Ranganayakulu%20et%20al%20JEBAS.pdf.
Rashwan, A.K., Karim, N., Shishir, M.R.I., Bao, T., Lu, Y., Chen, W., Jujube fruit: A potential nutritious fruit for the development of functional food products. Journal of Functional Foods, 75, 2020, 10.1016/j.jff.2020.104205 Article 104205.
Shaw, P.E., Tatum, J.H., Berry, R.E., 2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one, a degradation product of a hexose. Carbohydrate Research 16 (1971), 207–211, 10.1016/S0008-6215(00)86115-7.
Šimkovic, I., Nuñez, A., Strahan, G.D., Yadav, M.P., Mendichi, R., Hicks, K.B., Fractionation of sugar beet pulp by introducing ion-exchange groups. Carbohydrate Polymers 78 (2009), 806–812, 10.1016/j.carbpol.2009.06.022.
Xu, H., Zhang, X., Karangwa, E., Inhibition effects of Maillard reaction products derived from l-cysteine and glucose on enzymatic browning catalyzed by mushroom tyrosinase and characterization of active compounds by partial least squares regression analysis. RSC Advances 6:70 (2016), 65825–65836, 10.1039/C6RA15769F.
Yoshiki, Y., Okubo, K., Active oxygen scavenging activity of DDMP (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one) saponin in soybean seed. Bioscience Biotechnology and Biochemistry 59 (1995), 1556–1557, 10.1271/bbb.59.1556.
Yost, R., Fetterolf, D., Tandem mass spectrometry (MS/MS) instrumentation. Mass Spectrometry Reviews 2 (1983), 1–45, 10.1002/mas.1280020102.
Yu, X., Zhao, M., Liu, F., Zeng, S., Hu, J., Antioxidants in volatile Maillard reaction products: Identification and interaction. Lebensmittel-Wissenschaft und -Technologie- Food Science and Technology 53:1 (2013), 22–28, 10.1016/j.lwt.2013.01.024.
Zheng, X., Fu, W., Zheng, K., Gao, B., Lin, L., Liu, W., Lin, Z., Fang, Q., A novel method for the simultaneous determination of esterified 2-/3-MCPD and glycidol in foods by GC-MS/MS. Food Control, 123, 2021, 10.1016/j.foodcont.2020.107766 Article 107776.
Zhou, Z., Xu, Z., Shu, J., She, S., Sun, W., Yin, C., Chen, M., Li, Y., Zhong, F., Influence of various factors on formation of 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one (DDMP) in a solid-state model system of Maillard reaction. European Food Research and Technology 239:1 (2014), 31–40, 10.1007/s00217-014-2191-2.