Skip to main content
SpringerLink
Log in

Browning inhibition mechanisms by cysteine, ascorbic acid and citric acid, and identifying PPO-catechol-cysteine reaction products

  • Original Article
  • Published:
Journal of Food Science and Technology Aims and scope Submit manuscript

Abstract

The titled compounds were examined as PPO inhibitors and antibrowning agents; their various mechanisms were investigated and discussed. All compounds reduced significantly both the browning process and PPO activity. Browning index gave strong correlation with PPO activity (r2 = 0.96, n = 19) indicating that the browning process is mainly enzymatic. Ascorbic acid could reduce the formed quinone instantly to the original substrate (catechol) at high concentration (>1.5 %) while at lower concentrations acted as competitive inhibitor (KI = 0.256 ± 0.067 mM). Cysteine, at higher concentrations (≥1.0 %), reacted with the resulted quinone to give a colorless products while at the low concentrations, cysteine worked as competitive inhibitor (KI = 1.113 ± 0.176 mM). Citric acid acted only as PPO non-competitive inhibitor with KI = 2.074 ± 0.363 mM. The products of PPO-catechole-cysteine reaction could be separation and identification by LC-ESI-MS. Results indicated that the product of the enzymatic oxidation of catechol, quinone, undergoes two successive nucleophilic attacks by cysteine thiol group. Cysteine was condensed with the resulted mono and dithiocatechols to form peptide side chains.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 1
Scheme 2

Similar content being viewed by others

References

  • Ali HM, Abo-Shady A, Sharaf Eldeen HA, Soror HA, Shousha WG, Abdel-Barry OA, Saleh AM (2013) Structural features, kinetics and SAR study of radical scavenging and antioxidant activities of phenolic and anilinic compounds. Chem Cent J 7:53–61

    Article  Google Scholar 

  • Altunkaya A, Gökmen V (2008) Effect of various inhibitors on enzymatic browning, antioxidant activity and total phenol content of fresh lettuce (Lactuca sativa). Food Chem 107:1173–1179

    Article  CAS  Google Scholar 

  • Amorati R, Pedulli GF, Valgimigli L (2011) Kinetic and thermodynamic aspects of the chain-breaking antioxidant activity of ascorbic acid derivatives in non-aqueous media. Org Biomol Chem 9:3792–3800

    Article  CAS  Google Scholar 

  • Chang T-S (2009) An updated review of tyrosinase inhibitors. Int J Mol Sci 10:2440–2475

    Article  CAS  Google Scholar 

  • Chen Q-X, Song K-K, Qiu L, Liu X-D, Huang H, Guo H-Y (2005) Inhibitory effects on mushroom tyrosinase by p-alkoxybenzoic acids. Food Chem 91:269–274

    Article  CAS  Google Scholar 

  • Cilliers JJL, Singleton VL (1990) Caffeic acid autooxidation and the effects of thiols. J Agric Food Chem 38:1789–1796

    Article  CAS  Google Scholar 

  • Constabel CP, Barbehenn R (2008) defensive roles of polyphenol oxidase in plants. In: Schaller A (ed) Induced plant resistance to herbivory. Springer Science + Business Media BV, pp 253–269

  • Diedrich JK, Julian RR (2010) Site-selective fragmentation of peptides and proteins at quinone-modified cysteine residues investigated by ESI-MS. Anal Chem 82:4006–4014

    Article  CAS  Google Scholar 

  • Dincer B, Colak A, Aydin N, Kadioglu A, Güner S (2002) Characterization of polyphenoloxidase from medlar fruits (Mespilusgermanica L., Rosaceae). Food Chem 77:1–7

    Article  CAS  Google Scholar 

  • Ding C-K, Chachin K, Ueda Y, Wang CY (2002) Inhibition of loquat enzymatic browning by sulfhydryl compounds. Food Chem 76:213–218

    Article  CAS  Google Scholar 

  • Dixon M (1953) The determination of enzymeinhibition constants. Biochem J 55:170–171

    CAS  Google Scholar 

  • Dogăn M, Aslan O, Dogăn S (2002) Substrate specificity, heat inactivation and inhibition of polyphenol oxidase from different aubergine cultivars. Int J Food Sci Technol 37:415–423

    Article  Google Scholar 

  • Friedman M, Bautista FF (1995) Inhibition of polyphenol oxidase by thiol in the absence and presence of potato tissue suspensions. J Agric Food Chem 43:69–76

    Article  CAS  Google Scholar 

  • Garcia-Molina F, Penalver MJ, Rodriguez-Lopez JN, Garcia-Canovas F, Tudela J (2005) Enzymatic method with polyphenol oxidase for the determination of cysteine and N-acetylcysteine. J Agric Food Chem 53:6183–6189

    Article  CAS  Google Scholar 

  • Girelli AM, Mattei E, Messina A, Tarola AM (2004) Inhibition of polyphenol oxidases activity by various dipeptides. J Agric Food Chem 52:2714–2745

    Article  Google Scholar 

  • Golan-Goldhirsh A, Osuga DT, Chen AO, Whitker JR (1992) Effect of ascorbic acid and copper on proteins. In: O´Souza VT, Feder J (eds) The bioorganic chemistry of enzymatic catalysis. CRC Press, Boca Raton, pp 61–76

    Google Scholar 

  • Kumar D, Mishra DS, Chakraborty B, Kumar P (2011) Pericarp browning and quality management of litchi fruit by antioxidants and salicylic acid during ambient storage. J Food Sci Technol. doi:10.1007/s13197-011-0384-2

    Google Scholar 

  • Limbo S, Piergiovanni L (2006) Shelf life of minimally processed potatoes part 1. Effects of high oxygen partial pressures in combination with ascorbic and citric acids on enzymatic browning. Postharvest Biol Technol 39:254–264

    Article  Google Scholar 

  • Lineweaver H, Burk D (1934) The determination of enzyme dissociation constants. J Am Chem Soc 56:658–666

    Article  CAS  Google Scholar 

  • Misnawi JS, Jamilah B, Nazamid S (2003) Effects of incubation and polyphenol oxidase enrichment on colour, fermentation index, procyanidins and astringency of unfermented and partly fermented cocoa beans. J Food Sci Technol 38:285–295

    Article  CAS  Google Scholar 

  • Neves VA, Picchi DG, da Silva MA (2009) Some biochemical properties of polyphenoloxidase from spearmint (Menthaarvensis). Braz Arch Biol Technol 52:1001–1010

    Article  CAS  Google Scholar 

  • Nicolas JJ, Richard-Forget FC, Goupy PM, Amiot MJ, Aubert SY (1994) Enzymatic browning reactions in apple and products. Crit Rev Food Sci Nutr 34:109–157

    Article  CAS  Google Scholar 

  • Oliphant T, Mitra A, Wilkinson M (2012) Contact allergy to sodium sulfite and its relationship to sodium metabisulfite. Contact Dermatitis 66:128–130

    Article  CAS  Google Scholar 

  • Palou E, López-Malo A, Barbosa-Cánovas GV, Welti-Chanes J, Swanson BG (1999) Polyphenoloxidase activity and color of blanched and high hydrostatic pressure treated banana puree. J Food Sci 64:42–45

    Article  CAS  Google Scholar 

  • Peñalver MJ, Rodríguez-López JN, García-Molina F, García-Cánovas F, Tudela J (2002) Method for the determination of molar absorptivities of thiol adducts formed from diphenolic substrates of polyphenol oxidase. Anal Biochem 309:180–185

    Article  Google Scholar 

  • Queiroz C, Lopes MM, Fialho E, Valente-Mesquita VL (2008) Polyphenol oxidase: characteristics and mechanisms of browning control. Food Rev Int 24:361–375

    Article  CAS  Google Scholar 

  • Richard-Forget FC, Goupy PM, Nicolas JJ (1992) Cysteine as an inhibitor of enzymatic browning. 2. kinetic studies. J Agric Food Chem 40:2108–2113

    Article  CAS  Google Scholar 

  • Rupasinghe HPV, Murr DP, DeEll JR, Odumeru J (2005) Influence of 1-methylcyclopropene and NatureSeal on the quality of fresh-cut “Empire” and “Crispin” apples. J Food Qual 28:289–307

    Article  CAS  Google Scholar 

  • Sedaghat N, Zahedi Y (2012) Application of edible coating and acidic washing for extending the storage life of mushrooms (Agaricus bisporus). Food Sci Technol Int 18:523–530

    Article  Google Scholar 

  • Son SM, Moon KD, Lee CY (2001) Inhibitory effects of various antibrowning agents on apple slices. Food Chem 73:23–30

    Article  CAS  Google Scholar 

  • Stohs SJ, Miller MJS (2014) A case study involving allergic reactions to sulfur-containing compounds including, sulfite, taurine, acesulfame potassium and sulfonamides. ChemToxicol 63:240–243

    Article  CAS  Google Scholar 

  • Toivonen PMA, Brummell DA (2008) Biochemical bases of appearance and texture changes in fresh-cut fruit and vegetables. Postharvest Biol Technol 48:1–14

    Article  CAS  Google Scholar 

  • Watkins CB (2008) Overview of 1-methylcyclopropene trials and uses for edible horticultural crops. HortSci 43:86–94

    CAS  Google Scholar 

  • Whitaker JR (1994) Principals of enzymology for the food science, 2nd edn. Marcel Dekker, New York

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Agricultural Biochemistry Department, Faculty of Agriculture, Ain Shams University, Shoubra El-Kheima, Cairo, Egypt

    Hussein M. Ali

  2. Horticulture Department, Faculty of Agriculture, Ain Shams University, Shoubra El-Kheima, Cairo, Egypt

    Ahmed M. El-Gizawy

  3. Vegetable Handling Department, Horticulture Research Institute, Agricultural Research Center, Giza, Egypt

    Rawia E. I. El-Bassiouny & Mahmoud A. Saleh

  4. Faculty of Science For Girls, Chemistry Department, Dammam University, Dammam, Saudi Arabia, 31113, P.O. Box 838

    Hussein M. Ali

Authors
  1. Hussein M. Ali
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ahmed M. El-Gizawy
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Rawia E. I. El-Bassiouny
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mahmoud A. Saleh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hussein M. Ali.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ali, H.M., El-Gizawy, A.M., El-Bassiouny, R.E.I. et al. Browning inhibition mechanisms by cysteine, ascorbic acid and citric acid, and identifying PPO-catechol-cysteine reaction products. J Food Sci Technol 52, 3651–3659 (2015). https://doi.org/10.1007/s13197-014-1437-0

Download citation

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13197-014-1437-0

Keywords

Search

Navigation