Skip to main content
SpringerLink
Log in

Comparison of anti-browning ability and characteristics of the fractionated Maillard reaction products with different polarities

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

Abstract

The Maillard reaction products (MRPs) prepared from aqueous equimolar glucose with 1 M cysteine model solution when heated at 110 °C for 1 h was previously recognized as strong browning inhibitors for banana fruit. This study investigated further the anti-browning ability of the fractionated fractions with different polarity using solvent extraction following a ultra-filtration with 3.5 ku MWCO membrane and characteristized antioxidant activity including DPPH• scavenging ability and reducing power, chelating copper activity, inhibitory ability and the inhibitory constants of banana PPO. Extracts with different polarity were obtained by methanol, ethanol, n-butanol and isopropanol, which were designated as MRP(MeOH),MRP(EtOH),MRP(n-BuOH) and MRP(IPA), respectively. Application of the Lineweaver-Burk plotting showed that all MRPs were mixed-type 1 inhibitors whose Kis was larger than corresponding Ki, with Ki values ranging between 0.297 and 0.035 mg/mL MRPs. MRP(EtOH) showed the strongest anti-browning ability from the visual observation, further evidenced by its lowest Ki and IC50 in terms of the inhibition of PPO activity and DPPH• scavenging ability, with a different anti-browning mechanism vs. Na2S2O5. The strong copper chelating ability of the MRPs may account for the antioxidant ability and PPO activity inhibition to an extent. The effective anti-browning components from MRPs in glucose-cysteine model could be enriched by the combination of ultrafitration with ethanol extraction. And the extract may be applicable in food system.

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

Similar content being viewed by others

Abbreviations

(MRPs):

Maillard reaction products

(Cys):

Cysteine

(Glc):

Glucose

(PPO):

Polyphenoloxidase

(MW):

Molecule weight

(LMW):

Low molecular weight

(HMW):

High molecular weights

(EDTA):

Ethylene diamine tetraacetic acid

(Lys):

Lysine

(Fru):

Fructose

(MWCO):

Molecule weight cut off

(Na2S2O5):

Sodium metabisulphite

(AGEs):

Advanced glycation endproducts

(K3Fe(CN)6):

Potassium ferricyanide

(TMM):

Tetramethylmurexide

(PB):

Phosphate buffer

(DMSO):

Dimethyl sulfoxide

(IC50):

Half maximal inhibitory concentration of a substance

(DPPH•):

2, 2-Diphenyl-1-picrylhydrazyl

References

  • Bersuder P, Hole M, Smith G (1998) Antioxidants from a heated histidine-glucose model system. I: investigation of the antioxidant role of histidine and isolation of antioxidants by high-performance liquid chromatography. J Am Oil Chem Soc 75:181–187

    Article  CAS  Google Scholar 

  • Billaud C, Maraschin C, Chow YN, Chériot S, Peyrat-Maillard MN, Nicolas J (2005) Maillard reaction products as “natural antibrowning” agents in fruit and vegetable technology. Mol Nutr Food Res 49:656–662

    Article  CAS  Google Scholar 

  • Brun-Mérimée S, Billaud C, Louarme L, Nicolas J (2004) Effect of glutathione and Maillard reaction products prepared from glucose or fructose with glutathione on polyphenoloxidase from apple-II. Kinetic study and mechanism of inhibition. Food Chem 84:235–241

    Article  Google Scholar 

  • Chen XM, Kitts DD (2008) Antioxidant activity and chemical properties of crude and fractionated Maillard reaction products derived from four sugar–amino acid Maillard reaction model systems. Ann NY Acad Sci 1126:220–224

    Article  CAS  Google Scholar 

  • Cheriot S, Billaud C, Nicolas J (2006) Use of experimental design methodology to prepare Maillard reaction products from glucose and cysteine inhibitors of polyphenol oxidase from eggplant (Solanum melongena). J Agric Food Chem 54:5120–5126

    Article  CAS  Google Scholar 

  • Cheriot S, Billaud C, Pöchtrager S, Wagner KH, Nicolas J (2009) A comparison study between antioxidant and mutagenic properties of cysteine glucose-derived Maillard reaction products and neoformed products from heated cysteine and hydroxymethylfurfural. Food Chem 114:132–138

    Article  CAS  Google Scholar 

  • De Leonardis A, Lustrato G, Macciola V, Ranalli G (2010) Application of chemical and physical agents in model systems to controlling phenoloxidase enzymes. Eur Food Res Technol 231:603–610

    Article  CAS  Google Scholar 

  • Finot PA, Magnenat E (1981) Metabolic transit of early and advanced Maillard products. Prog Food Nutr Sci 5:193–207

    CAS  Google Scholar 

  • Hofmann T, Ames J, Krome K, Faist V (2001) Determination of the molecular weight distribution of non-enzymatic browning products formed by roasting of glucose and glycine and studies on their effects on NADPH-cytochrome c-reductase and glutathione-S-transferase in Caco-2 cells. Nahrung 45:189–194

    Article  CAS  Google Scholar 

  • Huang MG, Zhang XM, Eric K (2015) Comparation sensory characteristic, non-volatile compounds, volatile compounds and antioxidant activity of MRPs by novel gradient temperature-elevating and traditional isothermal methods. J Food Sci Technol 52:858–866

    Article  CAS  Google Scholar 

  • Jing H, Kitts DD (2004) Antioxidant activity of sugar-lysine Maillard reaction products in cell free and cell culture systems. Arch Biochem Biophys 15:154–163

    Article  Google Scholar 

  • Jung CH, Seog HM, Choi IW, Park MW, Cho HY (2006) Antioxidant properties of various solvent extract from wild ginseng leaves. LWT-Food Sci Technol 39:266–274

    Article  CAS  Google Scholar 

  • Kim JS, Lee YS (2010) Study of maillard reaction products in model aqueous and water/ethanol systems containing glucose and glycine, diglycine, and triglycine. Food Sci Biotechnol 19:1471–1477

    Article  CAS  Google Scholar 

  • Kim MK, Lee JS, Kim KY, Lee HG (2013) Ascorbyl palmitate-loaded chitosan nanoparticles: characteristic and polyphenol oxidase inhibitory activity. Colloids Surf B: Biointerfaces 103:391–394

    Article  CAS  Google Scholar 

  • Lee MK, Park I (2005) Inhibition of potato polyphenol oxidase by Maillard reaction products. Food Chem 91:57–61

    Article  CAS  Google Scholar 

  • Li YX, Su LL, Li FF, Wang CZ, Yuan DB, Chen J, Tan L, Jin ZQ, Ma WH (2015) Acute and sub-chronic toxicity of glucose-cysteine Maillard reaction products in Sprague-Dawley rats. Food Chem Toxicol 60:271–276

  • Lunadei L, Galleguillos P, Diezma B, Lleo L, Ruiz-Garcia L (2011) A multispectral vision system to evaluate enzymatic browning in fresh-cut apple slices. Postharvest Biol Technol 60:225–234

    Article  CAS  Google Scholar 

  • Maillard MN, Billaud C, Chow YN, Ordonaud C, Nicolas J (2007) Free radical scavenging, inhibition of polyphenoloxidase activity and copper chelating properties of model Maillard systems. LWT-Food Sci Technol 40:1434–1444

    Article  CAS  Google Scholar 

  • Matmaroh K, Benjakul S, Tanaka M (2006) Effect of reactant concentrations on the Maillard reaction in a fructose-glycine model system and the inhibition of black tiger shrimp polyphenoloxidase. Food Chem 98:1–8

    Article  CAS  Google Scholar 

  • Mogol BA, Yıldırım A, Gökmen V (2010) Inhibition of enzymatic browning in actual food systems by the Maillard reaction products. J Sci Food Agric 90:2556–2562

    Article  CAS  Google Scholar 

  • Monti SM, Ritieni A, Graziani G, Randazzo G, Mannina L, Segre AL, Fogliano V (1999) LC/MS analysis and antioxidative efficiency of Maillard reaction products from a lactose-lysine model system. J Agric Food Chem 47:1506–1513

    Article  CAS  Google Scholar 

  • Morales FJ, Babbel MB (2002) Melanoidins exert a weak antiradical activity in watery fluids. J Agric Food Chem 50:4657–4661

    Article  CAS  Google Scholar 

  • Morales FJ, Jimenez-Perez S (2001) Free radical scavenging capacity of Maillard reaction products as related to color and fluorescence. Food Chem 72:119–125

    Article  CAS  Google Scholar 

  • Murakami M, Shigeeda A, Danjo K, Yamaguchi T, Takamura H, Matoba T (2002) Radical-scavenging activity and brightly colored pigments in the early stages of Maillard reaction. J Food Sci 67:93–96

    Article  CAS  Google Scholar 

  • Oyaizu M (1986) Studies on products of browning reaction: antioxidative activities of products of browning reaction prepared from glucosamine. Jpn J Nutr 44:307–315

    Article  CAS  Google Scholar 

  • Poulsen MW, Hedegaard RV, Andersen JM, de Courten B, Bugel S, Nielsen J, Skibsted LH, Dragsted LO (2013) Advanced glycation endproducts in food and their effects on health. Food Chem Toxicol 60:10–37

    Article  CAS  Google Scholar 

  • Reichardt C (1994) Solvatochromic dyes as solvent polarity indicators. Chem Rev 94:2319–2358

    Article  CAS  Google Scholar 

  • Roux E, Billaud C, Maraschin C, Brun-Mérimée S, Nicolas J (2003) Inhibitory effect of unheated and heated D-glucose, D-fructose and L-cysteine solutions and Maillard reaction products model systems on polyphenoloxidase from apple. II. Kinetic study and mechanism of inhibition. Food Chem 81:51–60

    Article  CAS  Google Scholar 

  • Sadek PC (2002) HPLC solvent guide, 2nd edn. Wiley, New York, pp 77–78

    Google Scholar 

  • Sojo MM, Nuñez-Delicado E, García-Carmona F, Sánchez-Ferrer A (1999) Cyclodextrins as activator and inhibitor of latent banana pulp polyphenol oxidase. J Agric Food Chem 47:518–523

    Article  CAS  Google Scholar 

  • Teixeira GH, Durigan JF, Mattiuz B, Alves RE, O’Hare TJ (2006) Cultivar affects browning susceptibility of freshly cut star fruit slices. Sci Agric 63:1–4

    Article  Google Scholar 

  • Wijewickreme AN, Kitts DD (1997) Influence of reaction conditions on the oxidative behavior of model Maillard reaction products. J Agric Food Chem 45:4571–4576

    Article  CAS  Google Scholar 

  • Wijewickreme AN, Kitts DD, Durance TD (1997) Reaction conditions influence the elementary composition and metal chelating affinity of nondialyzable model Maillard reaction products. J Agric Food Chem 45:4577–4583

    Article  CAS  Google Scholar 

  • Wu JJ, Cheng KW, Li ETS, Wang MF, Ye WC (2008) Antibrowning activity of MRPs in enzyme and fresh-cut apple slice models. Food Chem 109:379–385

    Article  CAS  Google Scholar 

  • Yang CP, Sj F, Ashrafuzzaman MD, Nakamura N, Hayashi N (2000) Purification and characterization of polyphenol oxidase from banana (Musa sapientum L.) pulp. J Agric Food Chem 48:2732–2735

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the National Natural Science Foundation of China (grant Nos.: 31101328 and 31229004). The author also gratefully acknowledged the financial support from the Natural Science Foundation of Hainan Province (grant No. 311063) and Chinese Academy of Tropical Agricultural Sciences (grant Nos. 1630052012005 and 1630052014005).

Competing interests

There is no conflict of interest statement among the authors.

Author information

Authors and Affiliations

  1. Hainan Key Laboratory of Banana Genetic Improvement, Haikou Experimental Station, Chinese Academy of Tropical Agricultural Sciences, Haikou, 570102, People’s Republic of China

    Debao Yuan, Yinghao Xu, Chaozheng Wang, Yixing Li, Fenfang Li, Ya Zhou, Jiao Chen & Zhiqiang Jin

  2. Food Department, Hainan University, Haikou, 570102, People’s Republic of China

    Haide Zhang

  3. Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, 510650, People’s Republic of China

    Yueming Jiang

Authors
  1. Debao Yuan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yinghao Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chaozheng Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yixing Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Fenfang Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ya Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Jiao Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Zhiqiang Jin
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Haide Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Yueming Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yueming Jiang.

Additional information

Debao Yuan and Yinghao Xu contributed equally to this work.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yuan, D., Xu, Y., Wang, C. et al. Comparison of anti-browning ability and characteristics of the fractionated Maillard reaction products with different polarities. J Food Sci Technol 52, 7163–7172 (2015). https://doi.org/10.1007/s13197-015-1869-1

Download citation

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13197-015-1869-1

Keywords

Search

Navigation