Synthesis of a thiol-β-cyclodextrin, a potential agent for controlling enzymatic browning in fruits and vegetables

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 47, 2013, Pages 11603-11609

  Manta, Carmen ^a   Peralta Altier, Gabriela ^a   Gioia, Larissa ^a   Méndez, María F ^a   Seoane, Gustavo ^a   Ovsejevi, Karen ^a  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

Author keywords

antibrowning agent; polyphenol oxidase (PPO); thiol cyclodextrin (thiol CD)

Indexed keywords

AVERAGE VALUES; ENZYMATIC BROWNING; EPOXY ACTIVATION; FRUITS AND VEGETABLES; MICROENVIRONMENTS; POLYPHENOL OXIDASE; SOLID PHASE REDUCING AGENTS; THIOLATED-CYCLODEXTRIN;

CHEMICAL REACTIONS; FRUITS; VEGETABLES;

CYCLODEXTRINS;

BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; CATECHOL OXIDASE; THIOL BETA CYCLODEXTRIN; THIOL DERIVATIVE; THIOL-BETA-CYCLODEXTRIN;

ARTICLE; CHEMISTRY; MALUS; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

BETA-CYCLODEXTRINS; CATECHOL OXIDASE; MAGNETIC RESONANCE SPECTROSCOPY; MALUS; SULFHYDRYL COMPOUNDS;

EID: 84889823160     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf403063s     Document Type: Article

References (55)

1. French, D.; Rundle, R. E. The molecular weights of the Schardinger α-and β-dextrins J. Am. Chem. Soc. 1942, 64, 1651-1655
2. Koontz, J. L.; Marcy, J. E.; O'Keefe, S. F.; Duncan, S. E. Cyclodextrin inclusion complex formation and solid-state characterization of the natural antioxidants γ-tocopherol and quercetin J. Agric. Food Chem. 2009, 57, 1162-1171
3. Varca, G. H. C.; Andreo-Filho, N.; Lopes, P. S.; Ferraz, H. G. Cyclodextrins: an overview of the complexation of pharmaceutical proteins Curr. Protein Pept. Sci. 2010, 11, 255-263
4. Martin Del Valle, E. M. Cyclodextrins and their uses: a review Process Biochem. 2004, 39, 1033-1046
5. Mele, A.; Mendichi, R.; Selva, A.; Molnar, P.; Toth, G. Non covalent associations of cyclomaltooligosaccharides (cyclodextrins) with carotenoids in water. A study on the α- and β-cyclodextrin/ψ,ψ-carotene (lycopene) systems by light scattering, ionspray ionization and tandem mass spectrometry Carbohydr. Res. 2002, 337, 1129-1136
6. álvarez-Parrilla, E.; De la Rosa, L. A.; Torres-Rivas, F.; Rodrigo-García, J.; Gonzáles-Aguilar, G. A. Complexation of apple antioxidants: chlorogenic acid, quercetin and rutin by cyclodextrin J. Inclusion Phenom. 2005, 53, 121-129
7. Hedges, A. R. Industrial applications of cyclodextrins Chem. Rev. 1998, 98, 2035-2044
8. Kalogeropoulos, N.; Yannakopoulou, K.; Gioxari, A.; Chiou, A.; Makris, D. P. Polyphenol characterization and encapsulation in β-cyclodextrin of a flavonoid-rich Hypericum perforatum (St John's wort) extract LWT-Food Sci. Technol. 2010, 43, 882-889
9. Chaudhuri, S.; Chakraborty, S.; Sengupta, P. K. Encapsulation of serotonin in β-cyclodextrin nano-cavities: fluorescence spectroscopic and molecular modeling studies J. Mol. Struct. 2010, 975, 160-165
10. Mocanu, G.; Vizitiu, D.; Carpov, A. Cyclodextrin polymers J. Bioact. Compat. Polym. 2001, 16, 315-342
11. Astray, G.; Mejuto, J. C.; Rial-Otero, R.; González-Barreiro, C.; Simal-Gándara, J. A review on the use of cyclodextrins in foods Food Hydrocolloids 2009, 23, 1631-1640
12. López-Nicolás, J.; Pérez-López, A.; Carbonell-Barrachina, A.; García-Carmona, F. Use of natural and modified cyclodextrins as inhibiting agents of peach juice enzymatic browning J. Agric. Food Chem. 2007, 55, 5312-5319
13. Hicks, K. B.; Haines, R.; Tong, C. B. S.; Sapers, G. M.; El-Atawy, Y.; Irwin, P. L.; Seib, P. A. Inhibition of enzymatic browning in fresh fruit and vegetable juices by soluble and insoluble forms of β-cyclodextrin alone or in combination with phosphates J. Agric. Food Chem. 1996, 44, 2591-2594
14. Li-Qin, Z.; Jie, Z.; Shu-Hua, Z.; Lai-Hui, G. Inhibition of browning on the surface of peach slices by short-term exposure to nitric oxide and ascorbic acid Food Chem. 2009, 114, 174-179
15. Gorny, J. R.; Hess-Pierce, B.; Cifuentes, R. A.; Kader, A. A. Quality changes in fresh-cut pear slices as affected by controlled atmospheres and chemical preservatives Postharvest Biol. Technol. 2002, 24, 271-278
16. Valente Mezquita, V. L.; Queiroz, Ch. Enzymatic Browning. In Biochemistry of Foods, 3 rd ed.; Eskin, N. A. M.; Shahidi, F., Eds.; Academic Press: San Diego, CA, 2013; pp 387-418.
17. Peñalver, M. J.; Rodríguez-López, J. N.; García-Molina, F.; García-Cánovas, F.; Tudela, J. Method for the determination of molar absorptivities of thiol adducts formed from diphenolic substrates of polyphenol oxidase Anal. Biochem. 2002, 309, 180-185
18. Nikolantonaki, M.; Chichuc, I.; Teissedre, P. L.; Darriet, P. Reactivity of volatile thiols with polyphenols in a wine-model medium: impact of oxygen, iron, and sulfur dioxide Anal. Chim. Acta 2010, 660, 102-109
19. López-Nicolás, J.; Núñez-Delicado, E.; Sánchez-Ferrer, A.; García-Carmona, F. Kinetic model of apple juice enzymatic browning in the presence of cyclodextrins: the use of maltosyl-β-cyclodextrin as secondary antioxidant Food Chem. 2007, 101, 1164-1171
20. Eissa, H.; Fadel, H.; Ibrahim, G. E.; Hassan, I. M.; Abd Elrashid, A. Thiol containing compounds as controlling agents of enzymatic browning in some apple products Food Res. Int. 2006, 39, 855-863
21. Friedman, M.; Bautista, F. Inhibition of polyphenol oxidase by thiols in the absence and presence of potato tissue suspensions J. Agric. Food Chem. 1995, 43, 69-76
22. Guerrero-Beltrán, J.; Swanson, B.; Barbosa-Cánovas, G. Inhibition of polyphenoloxidases in mango puree with 4-hexylresorcinol, cysteine and ascorbic acid LWT-Food Sci. Technol. 2005, 38, 625-630
23. Yang, J.; Leung, D. K. Facile synthesis of β-cyclodextrin dithiols Bioorg. Med. Chem. Lett. 2002, 12, 169-170
24. Fujita, K.; Ueda, T.; Imoto, T.; Tabushi, I.; Toh, N.; Koga, T. Guest-induced conformational change of β-cyclodextrin capped with an environmentally sensitive chromophore Bioorg. Chem. 1982, 11, 72-84
25. Nelles, G.; Weisser, M.; Back, R.; Wohlfart, P.; Wenz, G.; Mittler-Neher, S. Controlled orientation of cyclodextrin derivatives immobilized on gold surfaces J. Am. Chem. Soc. 1996, 118, 5039-5046
26. Bollo, S.; Yáñez, C.; Sturm, J.; Núñez-Vergara, L.; Squella, J. A. Cyclic voltammetric and scanning electrochemical microscopic study of thiolated β-cyclodextrin adsorbed on a gold electrode Langmuir 2003, 19, 3365-3370
27. Croft, A. R.; Bartsch, R. A. Synthesis of chemically modified cyclodextrins Tetrahedron 1983, 39, 1417-1471
28. Brady, B.; Lynam, N.; O'Sullivan, T.; Ahern, C.; Darcy, R. 6a- O-p -Toluenesulfonyl-β-cyclodextrin Org. Synth. Coll. 2004, 10, 686
29. Melton, L. D.; Slessor, K. N. Synthesis of monosubstituted cyclohexaamyloses Carbohydr. Res. 1971, 18, 29-37
30. De Rango, C.; Charpin, P.; Navaza, J.; Keller, N.; Nicolis, I.; Villain, F.; Coleman, A. W. βcyclodextrin/pyridine gel systems. The crystal strycture of a first β-cyclodextrin-pyridine-water compound J. Am. Chem. Soc. 1992, 114, 5475
31. Defaye, J.; Gadelle, A.; Guiller, A.; Darcy, R.; O'Sullivan, T. Branched thiocyclomalto-oligosaccharides: synthesis and properties of 6- S -α- and 6- S -β- d -glucopyranosyl-6-thiocyclomaltoheptaose Carbohydr. Res. 1989, 192, 251
32. Gadelle, A.; Defaye, J. Selective halogenation at primary positions of cyclomalotooligosaccharides and a synthesis of per-3,6-anhydro cyclomalotooligosaccharides Angew. Chem., Int. Ed. Engl. 1991, 30, 78-79
33. Rojas, M.; Koniger, R.; Frases Stoddart, J.; Kaifer, A. E. Supported monolayers containing preformed binding sites. Synthesis and interfacial binding properties of a thiolated β-cyclodextrin derivative J. Am. Chem. Soc. 1995, 117, 336-343
34. Camacho, C.; Matías, J. C.; Chico, B.; Cao, R.; Gómez, L.; Simpson, B. K.; Villalonga, R. Amperometric biosensor for hydrogen peroxide, using supramolecularly immobilized horseradish peroxidase on the β-cyclodextrin-coated gold electrode Electroanalysis 2007, 19, 2538-2542
35. Peng, K.; Tomatsu, I.; Korobko, A. V.; Kros, A. Cyclodextrin-dextran, based in situ hydrogel formation: a carrier for hydrophobic drugs Soft Matter 2010, 6, 85-87
36. Camacho, C.; Chico, B.; Cao, R.; Matías, J. C.; Hernández, J.; Palchetti, I.; Simpson, B.; Mascini, M.; Villalonga, R. Novel enzyme biosensor for hydrogen peroxide via supramolecular associations Biosens. Bioelectron. 2009, 24, 2028-2033
37. Sundberg, L.; Porath, J. Preparation of adsorbents for biospecific affinity chromatography. I. Attachment of group-containing ligands to insoluble polymers by means of bifunctional oxiranes J. Chromatogr. 1974, 90, 87-98
38. Batista-Viera, F.; Barbieri, M.; Ovsejevi, K.; Manta, C.; Carlsson, J. A new method for reversible immobilization of thiol biomolecules based on solid phase bound thiolsulfonate groups J. Appl. Biochem. Biotechnol. 1991, 31, 175-195
39. Batista-Viera, F.; Manta, C.; Carlsson, J. Solid phase thiolsulfinates for the reversible immobilization of thiols Appl. Biochem. Biotechnol. 1994, 44, 1-14
40. Batista-Viera, F.; Manta, C.; Carlsson., J. Covalent binding of thiols to thiolsulfinate-containing supports Biotechnol. Appl. Biochem. 1996, 24, 231-239
41. Axén, R.; Drevin, H.; Carlsson, J. Preparation of modified agarose gels containing thiol groups Acta Chem. Scand. Ser. B 1975, 29, 471-474
42. Grazú, V.; Ovsejevi, K.; Cuadra, K.; Betancor, L.; Manta, C.; Batista-Viera, F. Solid-phase reducing agents as alternative for reducing disulfide bonds in proteins Appl. Biochem. Biotechnol. 2003, 110, 23-32
43. Ovsejevi, K.; Grazú, V.; Cuadra, K.; Batista-Viera, F. Enzyme reduction on solid phase as a tool for the reversible immobilization of yeast β-galactosidase onto a thiol-reactive support Enzyme Microb. Technol. 2004, 37, 456-462
44. Man, M.; Bryant, R. G. Reactions of thiosulfate and sulfite ions with DTNB: interferente in sulfhydryl group analysis Anal. Biochem. 1974, 57, 429-431
45. Vikmon, M. Rapid and simple spectrophotometric method for determination of microamounts of cyclodextrins. In First Symposium on Cyclodextrins; Szejtli, J., Ed.; Reidel Publishing: Budapest, Hungary, 1982; pp 69-74.
46. Ellman, G. L. Colorimetric method for determining low concentrations of mercaptans Arch. Biochem. Biophys. 1958, 74, 443-450
47. Fu, Y.; Zhang, K.; Wang, N.; Du, J. Effects of aqueous clorine dioxide treatment on polyphenol oxidases from Golden Delicious apple LWT-Food Sci. Technol. 2007, 1362-1368
48. Polyphenol oxidase. In Worthington Enzyme Manual; Worthington: Freehold, NJ, 1993.
49. Denoya, G. I.; Pirola, P. M.; Sanow, C. L.; Benítez, C. E. Análisis de la evolución de características cromáticas como parámetro de calidad en vegetales cortados. Chapter A-3. In World Congress and Exhibition Engineering 2010, Buenos Aires, Argentina, 2010.
50. Soliva-Fortuny, R. C.; Oms-Oliu, G.; Martín-Belloso, O. Effects of ripeness stages on the storage atmosphere, color, and textural properties of minimally processed apple slices J. Food Sci. 2002, 67, 1958-1963
51. Vasantha Rupansinghe, H. P.; Murr, D.; Deell, J.; Odumeru, J. Influence of 1-methycyclopropene and nature seal on the quality of fresh-cut 'Empire' and 'Crispin' apples J. Food Qual. 2005, V28, 289-307
52. Perez-Gago, M. B.; Serra, M.; del Río, M. A. Color change of fresh cut apples coated with whey protein concentrate-based edible coatings Postharvest Biol. Technol. 2006, 39, 84-92
53. Renard, E.; Deratani, A.; Volet, G.; Sebille, B. Preparation and characterization of water soluble high molecular weight β-cyclodextrin- epichlorohydrin polymers Eur. Polym. J. 1997, 33, 49-57
54. Billaud, C.; Regaydie, E.; Fayad, N.; Richard-Forget, F.; Nicolas, J. Effect of cyclodextrins on polyphenol oxidation catalyzed by apple polyphenol oxidase. In Enzymatic Browning and Its Prevention; Lee, C. Y.; Whitaker, J. R., Eds.; ACS Symposium Series 600; American Chemical Society: Washington, DC, 1995; pp 295-312.
55. Chisari, M.; Barbagallo, R. N.; Spagna, G. Charaterization and role of polyphenol oxidase and peroxidase in browning in fresh-cut melon J. Agric. Food Chem. 2008, 56, 132-138