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On the role of 2,3-dihydro-3,5-dihydroxy-6-methyl-(4H)-pyran-4-one in antioxidant capacity of prunes

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Abstract

Despite available reports on phenolic composition and antioxidant capacity (AOC) of fresh plums and prunes, there is a scarcity of published knowledge on the antioxidants formed and/or released during the drying process in the literature. To evaluate the compounds participating in reducing capacity of prunes, we compared aqueous and methanol extracts of fresh plums, commercial prunes and home-made prunes prepared at different drying temperatures using an HPLC method with amperometric detection (HPLC-ECD). The prunes dried at high temperature (90 °C, 18 h) in kitchen or laboratory oven with restricted ventilation gave up to 3.3 times higher electrochemical capacity (EC) than fresh plums (dry matter; P. domestica cv. Domestica) in dependence on production protocol. Drying at 60 °C (low-temperature drying) for 18 h did not change the EC significantly. Yet, lower EC was found in commercial tenderized prunes with sorbate; they were by a factor of 1.1–8.2 lower in EC than the prepared low-temperature prunes. The principle responsible for the increase in EC in the prunes prepared at high temperatures is 2,3-dihydro-3,5-dihydroxy-6-methyl-(4H)-pyran-4-one (DDMP). It was not detected until 74 °C was set during isothermal 18 h drying or until 6 h of drying passed at 90ºC drying. The ultimate acceptable dwell-time for the preparation of conveniently eatable prunes dried at 90ºC under the conditions used was assessed to 12 h. The EC of plums and prunes as well as the role of DDMP was confirmed by the use of several methods for the assessment of AOC-DPPH assay, β-carotene bleaching method, Oxipres test and Schaal oven test.

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References

  1. Czech Statistical Office (2010). Consumption of food, beverages, and cigarettes in the Czech Republic in 2001–2009. Available at: http://www.czso.cz/csu/2010edicniplan.nsf/engp/3004-10. Accessed Jan 13, 2011

  2. Carlsen MH, Halvorsen BL, Holte K, Bohn SK, Dragland S, Sampson L, Willey C, Senoo H, Umezono Y, Sanada C, Barikmo I, Berhe N, Willet WC, Phillips KM, Jacobs DR, Blomhoff R (2010) The total antioxidant content of more than 3100 foods, beverages, spices, herbs and supplements used worldwide. Nutr J 9:3

    Article  Google Scholar 

  3. Wang H, Cao G, Pryor RL (1996) Total antioxidant capacity of fruits. J Agric Food Chem 44:701–705

    Article  CAS  Google Scholar 

  4. Wu X, Beecher GR, Holden JM, Haytowicz DB, Gebhardt SE, Prior RL (2004) Lipophilic and hydrophilic antioxidant capacities of common foods in the United States. J Agric Food Chem 52:4026–4037

    Article  CAS  Google Scholar 

  5. Gil MI, Tomás-Barberán FA, Hess-Pierce B, Kader AA (2002) Antioxidant capacities, phenolic compounds, carotenoids, and vitamin C contents of nectarine, peach, and plum cultivars from California. J Agric Food Chem 50:4976–4982

    Article  CAS  Google Scholar 

  6. Kim DO, Chun OK, Kim YJ, Moon HY, Lee CY (2003) Quantification of polyphenolics and their antioxidant capacity in fresh plums. J Agric Food Chem 51:6509–6515

    Article  CAS  Google Scholar 

  7. Stacewicz-Sapuntzakis M, Bowen PE, Hussain EA, Damayanti-Wood BI, Farnsworth NR (2001) Chemical composition and potential health effects of prunes: a functional food? Crit Rev Food Sci 41:251–286

    Article  CAS  Google Scholar 

  8. Piga A, Del Caro A, Corda G (2003) From plums to prunes: influence of drying parameters on polyphenols and antioxidant activity. J Agric Food Chem 51:3675–3681

    Article  CAS  Google Scholar 

  9. Raynal J, Moutounet M, Souquet JM (1989) Intervention of phenolic compounds in plum technology. 1. Changes during drying. J Agric Food Chem 37:1046–1050

    Article  CAS  Google Scholar 

  10. Donovan JL, Meyer AS, Waterhouse AL (1998) Phenolic composition and antioxidant activity of prunes and prune juice (Prunus domestica). J Agric Food Chem 46:1247–1252

    Article  CAS  Google Scholar 

  11. Hennning W, Herrmann K (1980) Flavonol glycosides of plums (Prunus domestica and Prunus salicina). Phenolics of fruits. Part 12. Z Lebensm Unters Forsch 171:111–118

    Article  Google Scholar 

  12. Wu X, Prior RL (2005) Systematic identification and characterization of anthocyanins by HPLC-ESI-MS/MS in common foods in the United States: fruits and berries. J Agric Food Chem 53:2589–2599

    Article  CAS  Google Scholar 

  13. Vinson JA, Su X, Zubik L, Bose P (2001) Phenol antioxidant quantity and quality in foods: fruits. J Agric Food Chem 49:5315–5321

    Article  CAS  Google Scholar 

  14. Forni E, Erba ML, Maestrelli A, Polesello A (1992) Sorbitol and free sugar contents in plums. Food Chem 44:269–275

    Article  CAS  Google Scholar 

  15. Belitz H-D, Grosch W, Schieberle P (2004) Food Chemistry, 3rd revised English edition. Springer, Berlin, 817

  16. Velíšek J, Cejpek K (2008) Biosynthesis of food components. OSSIS Tábor, p 140

  17. UNECE standard DDP-07 concerning the marketing and commercial quality control of prunes (2003) United Nations, New York and Geneva

  18. Price WE, Sabarez HT, Storey R, Back PJ (2000) Role of the waxy skin layer in moisture loss during dehydration of prunes. J Agric Food Chem 48:4193–4198

    Article  CAS  Google Scholar 

  19. Di Matteo M, Cinquanta L, Galiero G, Crescitelli S (2002) Physical pre-treatment of plums (Prunus domestica). Part 1. Modelling the kinetics of drying. Food Chem 79:227–232

    Article  CAS  Google Scholar 

  20. Nakatani N, Kayano S, Kikuzaki H, Sumino K, Katagiri K, Mitani T (2000) Identification, determination and antioxidative activities of chlorogenic acid isomers in prune (Prunus domestica L.). J Agric Food Chem 48:5512–5516

    Article  CAS  Google Scholar 

  21. Pellegrini N, Serafini M, Salvatore S, Del Rio D, Bianchi M, Brighenti F (2006) Total antioxidant capacity in spices, dried fruits, nuts, pulses, cereals and sweets consumed in Italy assessed by three different in vitro assays. Mol Nutr Food Res 50:1030–1038

    Article  CAS  Google Scholar 

  22. Halvorsen BL, Carlsen MH, Phillips KM, Bohn Holte K, Jacobs DR Jr, Blomhoff R (2006) Content of redox active compounds (i.e., antioxidants) in foods consumed in the United States. Am J Clin Nutr 84:95–135

    CAS  Google Scholar 

  23. Del Caro A, Piga A, Pinna I, Agabbio M (2004) The effect of storage on polyphenolic content, antioxidant activity and ascorbic acid of prunes. J Agric Food Chem 52:4780–4784

    Article  CAS  Google Scholar 

  24. Brand-Williams W, Cuvelier ME, Berset C (1995) Use of free radical method to evaluate antioxidant activity. Lebensm Wiss Technol 28:25–30

    CAS  Google Scholar 

  25. Trojáková L, Réblová Z, Pokorný J (1999) Determination of the oxidative stability of fats and oils using the Oxipres apparatus. Czech J Food Sci 17:68–72

    Google Scholar 

  26. Rop O, Jurikova T, Mlcek J, Kramarova D, Sengee Z (2009) Antioxidant activity and selected utritional values of plums (Prunus domestica L.) typical of the White Carpathian Mountains. Sci Hortic 122:545–549

    Article  CAS  Google Scholar 

  27. Sabarez HT, Price WE (1999) Prune dehydration: kinetic studies and modelling. J Food Eng 42:167–172

    Article  Google Scholar 

  28. Kayano S, Yamada NF, Suzuki T, Ikami T, Shioaki K, Kikutaki H, Mitani T, Nakatani N (2003) Quantitative evaluation of antioxidant components in prunes (Prunus domestica L.). J Agric Food Chem 51:1480–1485

    Article  CAS  Google Scholar 

  29. Jiang D, Peterson DG (2010) Role of hydroxycinnamic acids in food flavour: a brief overview. Phytochem Rev 9:187–193

    Article  CAS  Google Scholar 

  30. Fang N, Yu S, Prior RL (2002) LC/MS/MS characterization of phenolic constituents in dried plums. J Agric Food Chem 50:3579–3585

    Article  CAS  Google Scholar 

  31. Kikuzaki H, Kakyano S, Fulutsuka N, Aoki A, Kasamatsu K, Yamasaki Y, Mitani D, Nakatani N (2004) Abscisic acid related compounds and lignans in prunes (Prunus domestica L.) and their oxygen radical absorbance capacity (ORAC). J Agric Food Chem 52:344–349

    Article  CAS  Google Scholar 

  32. Kayano S, Kikuzaki H, Fukutsuka N, Mitani T, Nakatani N (2002) Antioxidant activity of prune (Prunus domestica L.) constituents and a new synergist. J Agric Food Chem 50:3708–3712

    Article  CAS  Google Scholar 

  33. Nursten H (2005) The Maillard reaction: chemistry, biochemistry and implications. RSC, Cambridge

    Google Scholar 

  34. Wilford LG, Sabarez HT, Price WE (1997) Kinetics of carbohydrate change during dehydration of d’Agen prunes. Food Chem 59:149–155

    Article  CAS  Google Scholar 

  35. Konečný M, Cejpek K, Čechovská L, Velíšek J (2009) Transformation pathways of reductones in the advanced Maillard reaction. Czech J Food Sci 27:149–152

    Google Scholar 

  36. Kim MO, Baltes W (1996) On the role of 2,3-dihydro-3, 5-dihydroxy-6-methyl-4(H)-pyran-4-one in the Maillard reaction. J Agric Food Chem 44:282–289

    Article  CAS  Google Scholar 

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Acknowledgments

This work was partially supported by the research grant MSM 6046137305 of the Czech Ministry of Education, Youth and Sports.

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Correspondence to Karel Cejpek.

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Čechovská, L., Cejpek, K., Konečný, M. et al. On the role of 2,3-dihydro-3,5-dihydroxy-6-methyl-(4H)-pyran-4-one in antioxidant capacity of prunes. Eur Food Res Technol 233, 367–376 (2011). https://doi.org/10.1007/s00217-011-1527-4

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