Biocatalytic cross-linking of pectic polysaccharides for designed food functionality: Structures, mechanisms, and reactions

Biocatalysis and Agricultural Biotechnology

Volumn 1, Issue 3, 2012, Pages 207-219

  Zaidel, Dayang Norulfairuz Abang ^a,b   Meyer, Anne S ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b UNIVERSITI TEKNOLOGI MALAYSIA   (Malaysia)

Author keywords

Cross link; Enzymatic; Food functionality; Polysaccharide

Indexed keywords

EID: 84861231638     PISSN: 18788181     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcab.2012.03.007     Document Type: Review

References (92)

1. 2+-induced gelation in alginates and pectins: the egg-box model revisited. Biomacromolecules 2001, 2:1089-1096.
2. Bunzel M., Ralph J., Funk C., Steinhart H. Structural elucidation of new ferulic acid-containing phenolic dimers and trimers isolated from maize bran. Tetrahedron Lett. 2005, 46:5845-5850.
3. Bunzel M., Ralph J., Bruning P., Steinhart H. Structural identification of dehydrotriferulic and dehydrotetraferulic acids isolated from insoluble maize bran fiber. J. Agric. Food. Chem. 2006, 54:6409-6418.
4. Bunzel M., Heuermann B., Kim H., Ralph J. Peroxidase-catalyzed oligomerization of ferulic acid esters. J. Agric. Food. Chem. 2008, 56:10368-10375.
5. Berlanga-Reyes C.M., Carvajal-Millan E., Juvera G.C., Rascon-Chu A., Marquez-Escalante J.A., Martinez-Lopez A.L. Laccase induced maize bran arabinoxylan gels: structural and rheological properties. Food Sci. Biotechnol. 2009, 18:1027-1029.
6. Berlanga-Reyes C.M., Carvajal-Millan E., Lizardi-Mendoza J., Islas-Rubio A.R., Rascón-Chu A. Enzymatic cross-linking of alkali extracted arabinoxylans: gel rheological and structural characteristics. Int. J. Mol. Sci. 2011, 12:5853-5861.
7. Boeriu C.G., Oudgenoeg G., Spekking W.T.J., Lbjm Berendsen, Vancon L., Boumans H., et al. Horseradish peroxidase-catalyzed cross-linking of feruloylated arabinoxylans with Β-casein. J. Agric. Food. Chem. 2004, 52:6633-6639.
8. Brown J.A., Fry S.C. Novel O-D-galacturonoyl esters in the pectic polysaccharides of suspension-cultured plant cells. Plant Physiol. 1993, 103:993-999.
9. Cosgrove D.J. Expansive growth of plant cell walls. Plant Physiol. Biochem. 2000, 38:109-124.
10. Caffall K.H., Mohnen D. The structure, function, and biosynthesis of plant cell wall pectic polysaccharides. Carbohydr. Res. 2009, 344:1879-1900.
11. Coenen G.J., Bakx E.J., Verhoef R.P., Schols H.A., Voragen A.G.J. Identification of the connecting linkage between homo- or xylogalacturonan and rhamnogalacturonan type I. Carbohydr. Polym. 2007, 70:224-235.
12. Colquhoun I.J., Ralet M.C., Thibault J.F., Faulds C.B., Williamson G. Structure identification of feruloylated oligosaccharides from sugar beet pulp by NMR spectroscopy. Carbohydr. Res. 1994, 263:243-256.
13. Corredig M., Kerr W., Wicker L. Particle size distribution of orange juice cloud after addition of sensitized pectin. J. Agric. Food. Chem. 2001, 49:2523-2526.
14. Croak S., Corredig M. The role of pectin in orange juice stabilization: Effect of pectin methylesterase and pectinase activity on the size of cloud particles. Food Hydrocolloids 2006, 20:961-965.
15. Chen B., McClements D.J., Gray D.A., Decker E.A. Stabilization of soybean oil bodies by enzyme (laccase) cross-linking of adsorbed beet pectin coatings. J. Agric. Food. Chem. 2010, 58:9259-9265.
16. Carvajal-Millan E., Guigliarelli B., Belle V., Rouau X., Micard V. Storage stability of laccase induced arabinoxylan gels. Carbohydr. Polym. 2005, 59:181-188.
17. Carvajal-Millan E., Guilbert S., Morel M.H., Micard V. Impact of the structure of arabinoxylan gels on their rheological and protein transport properties. Carbohydr. Polym. 2005, 60:431-438.
18. Denès J.M., Baron A., Renard C.M.G.C., Péan C., Drilleau J.F. Different action patterns for apple pectin methylesterase at pH 7.0 and 4.5. Carbohydr. Res. 2000, 327:385-393.
19. Fissore E.N., Rojas A.M., Gerschenson L.N. Rheological performance of pectin-enriched products isolated from red beet (Beta vulgaris L. var. conditiva) through alkaline and enzymatic treatments. Food Hydrocolloids 2012, 26:246-260.
20. Fraeye I., Colle I., Vandevenne E., Duvetter T., Buggenhout S.V., Moldenaers P., et al. Influence of pectin structure on texture of pectin-calcium gels. Innovative Food Sci. Emerging Technol. 2010, 11:401-409.
21. Fraeye I., Duvetter T., Doungla E., Loey A.V., Hendrickx M. Fine-tuning the properties of pectin-calcium gels by control of pectin fine structure, gel composition and environmental conditions. Trends Food Sci. Technol. 2010, 21:219-228.
22. Figueroa-Espinoza M.C., Rouau X. Oxidative cross-linking of pentosans by a fungal laccase and horseradish peroxidase: mechanism of linkage between feruloylated arabinoxylans. Cereal Chem. 1998, 75:259-265.
23. Guillon F., Thibault J.F. Oxidative cross-linking of chemically and enzymatically modified sugar-beet pectin. Carbohydr. Polym. 1990, 12:353-374.
24. Holck J., Hjernø K., Lorentzen A., Vigsnæs L.K., Hemmingsen L., Licht T.R., et al. Tailored enzymatic production of oligosaccharides from sugar beet pectin and evidence of differential effects of a single DP chain length difference on human faecal microbiota composition after in vitro fermentation. Process Biochem. 2011, 46:1039-1049.
25. Hotchkiss A.T.J., Savary B.J., Cameron R.G., Chau H.K., Brouillette J., Luzio G.A., et al. Enzymatic modification of pectin to increase its calcium sensitivity while preserving its molecular weight. J. Agric. Food. Chem. 2002, 50:2931-2937.
26. Hilz H., Williams P., Doco T., Schols H.A., Voragen A.G.J. The pectic polysaccharide rhamnogalacturonan II is present as a dimer in pectic populations of bilberries and black currants in muro and in juice. Carbohydr. Polym. 2006, 65:521-528.
27. Hou W.C., Chang W.H. Pectinesterase-catalyzed firming effects during precooking of vegetables. J. Food Biochem. 1996, 20:397-416.
28. Hwang J.Y., Lee C.W., Wu M.C., Chang H.M. Transacylation and de-esterification reactions of pectin as catalyzed by pectinesterases from tomato and citrus. J. Agric. Food. Chem. 2003, 51:6287-6292.
29. Hilz H., 2007. Characterisation of Cell Wall Polysaccharides in Bilberries and Black Currants. Ph.D. Thesis. Wageningen University, The Netherlands.
30. Itoh K., Hatakeyama T., Shimoyama T., Miyazaki S., D'Emanuele A., Attwood D. In situ gelling formulation based on methylcellulose/pectin system for oral-sustained drug delivery to dysphagic patients. Drug Dev. Ind. Pharm. 2011, 37:790-797.
31. Ishii T., Matsunaga T., Pellerin P., O'Neill M.A., Darvill A., Albersheim P. The plant cell wall polysaccharide rhamnogalacturonan II self-assembles into a covalently cross-linked dimer. J. Biol. Chem. 1999, 274:13098-13104.
32. Izydorczyk M.S., Biliaderis C.G. Cereal arabinoxylans: advances in structure and physicochemical properties. Carbohydr. Polym. 1995, 28:33-48.
33. Ishii T., Matsunaga T. Pectic polysaccharide rhamnogalacturonan II is covalently linked to homogalacturonan. Phytochemistry 2001, 57:969-974.
34. Jung J., Wicker L. Laccase mediated conjugation of sugar beet pectin and the effect on emulsion stability. Food Hydrocolloids 2012, 28:168-173.
35. Jiang C.M., Lai Y.J., Lee B.H., Chang W.H., Chang H.M. De-esterification and transacylation reactions of pectinesterase from Jelly fig (Ficus awkeotsang Makino) achenes. J. Food Sci. 2001, 66:810-815.
36. Jiang C.M., Wu M.C., Chang W.H., Chang H.M. Change in particle size of pectin reacted with pectinesterase isozymes from pea (Pisum sativum L.) sprouts. J. Agric. Food. Chem. 2001, 49:4383-4387.
37. Kim Y., Wicker L. Charge domain of modified pectins influence interaction with acidified caseins. Food Hydrocolloids 2011, 25:419-425.
38. Kuuva T., Lantto R., Reinikainen T., Buchert J., Autio K. Rheological properties of laccase-induced sugar beet pectin gels. Food Hydrocolloids 2003, 17:679-684.
39. 2+ on the gelation of low-methoxylated pectin at acidic pH. Food Hydrocolloids 2012, 27:42-49.
40. Liu B., Bhaladhare S., Zhan P., Jiang L., Zhang J., Liu L., et al. Morphology and properties of thermoplastic sugar beet pulp and poly(butylenes adipate-co-terepthalate) blends. Ind. Eng. Chem. Res. 2011, 50:13859-13865.
41. Lerouge P., O'Neill M.A., Darvill A.G., Albersheim P. Structural characterization of endo-glycanase-generated oligoglycosyl side chains of rhamnogalacturonan I. Carbohydr. Res. 1993, 243:359-371.
42. Levigne S.V., Ralet M.C.J., Quéméner B.C., Pollet B.N.L., Lapierre C., Thibault J.F.J. Isolation from sugar beet cell walls of arabinan oligosaccharides esterified by two ferulic acid monomers. Plant Physiol. 2004, 134:1173-1180.
43. Luzio G.A., Cameron R.G. Demethylation of a model homogalacturonan with the salt-independent pectin methylesterase from citrus: part II. Structure-function analysis. Carbohydr. Polym. 2008, 71:300-309.
44. Lee H., Rivner J., Urbauer J.L., Garti N., Wicker L. De-esterification pattern of Valencia orange pectinmethylesterases and characterization of modified pectins. J. Sci. Food Agric. 2008, 88:2102-2110.
45. Littoz F.F., McClements D.J. Bio-mimetic approach to improving emulsion stability: cross-linking adsorbed beet pectin layers using laccase. Food Hydrocolloids 2008, 22:1203-1211.
46. Li J.L., Cheng Y.Q., Wang P., Zhao W.T., Yin L.J., Saito M. A novel improvement in whey protein isolate emulsion stability: Generation of an enzymatically cross-linked beet pectin layer using horseradish peroxidase. Food Hydrocolloids 2012, 26:448-455.
47. Munarin F., Guerreiro S.G., Grellier M.A., Tanzi M.C., Barbosa M.A., Petrini P., et al. Pectin-based injectable biomaterials for bone tissue engineering. Biomacromolecules 2011, 12:568-577.
48. Min B., Lim J., Ko S., Lee K.G., Lee S.H., Lee S. Environmentally friendly preparation of pectins from agricultural byproducts and their structural/rheological characterization. Bioresour. Technol. 2011, 102:3855-3860.
49. Micard V., Grabber J.H., Ralph J., MGC Renard, Thibault J.F. Dehydrodiferulic acids from sugar beet pulp. Phytochemistry 1997, 44:1365-1368.
50. Micard V., Thibault J.F. Oxidative gelation of sugar-beet pectins: use of laccases and hydration properties of the cross-linked pectins. Carbohydr. Polym. 1999, 39:265-273.
51. 2+-pectin gels. Food Hydrocolloids 2012, 26:44-53.
52. 2+-gels of partially methylesterified polygalacturonic acid: Effect of "mixed" patterns of methylesterification. Carbohydr. Polym. 2012, 88:37-45.
53. 2+-pectin gels: Towards understanding structure-function relations of pectin. Food Hydrocolloids 2012, 26:89-98.
54. 2+ concentractions. Carbohyr. Res. 2012, 348:69-76.
55. Norsker M., Jensen M., Adler-Nissen J. Enzymatic gelation of sugar beet pectin in food products. Food Hydrocolloids 2000, 14:237-243.
56. Oosterveld A., Beldman G., Schols H.A., Voragen A.G.J. Characterization of arabinose and ferulic acid rich pectic polysaccharides and hemicelluloses from sugar beet pulp. Carbohydr. Res. 2000, 328:185-197.
57. O'Neill M.A., Ishii T., Albersheim P., Darvill A.G., Rhamnogalacturonan I.I. Structure and function of a borate cross-linked cell wall pectic polysaccharide. Annu. Rev. Plant Biol. 2004, 55:109-139.
58. O'Neill M.A., Warrenfeltz D., Kates K., Pellerin P., Doco T., Darvill A.G., et al. Rhamnogalacturonan-II, a pectic polysaccharide in the walls of growing plant cell, forms a dimer that is covalently cross-linked by a borate ester: In vitro conditions for the formation and hydrolysis of the dimer. J. Biol. Chem. 1996, 271:22923-22930.
59. Parr A.J., Waldron K.W., Ng A., Parker M.L. The wall-bound phenolics of Chinese water chestnut (Eleocharis dulcis). J. Sci. Food Agric. 1996, 71:501-507.
60. Popper Z.A., Fry S.C. Xyloglucan-pectin linkages are formed intra-protoplasmically, contribute to wall-assembly, and remain stable in the cell wall. Planta 2008, 227:781-794.
61. Popper Z.A., Fry S.C. Widespread occurrence of a covalent linkage between xyloglucan and acidic polysaccharides in suspension-cultured angiosperm cells. Ann. Bot. 2005, 96:91-99.
62. Ridley B.L., O'Neill M.A., Mohnen D. Pectins: structure, biosynthesis, and oligogalacturonide-related signaling. Phytochemistry 2001, 57:929-967.
63. Ralet M.C., Crépeau M.J., Buchholt H.C., Thibault J.F. Polyelectrolyte behavior and calcium binding properties of sugar beet pectins differing in their degrees of methylation and acetylation. Biochem. Eng. J. 2003, 16:191-201.
64. Ralph J., Quideau S., Grabber J.H., Hatfield R.D. Identification and synthesis of new ferulic acid dehydrodimers present in grass cell walls. J. Chem. Soc. Perkin Trans. 1994, 1:3485-3498.
65. Robertson J.A., Faulds C.B., Smith A.C., Waldron K.W. Peroxidase-mediated oxidative cross-linking and its potential to modify mechanical properties in water-soluble polysaccharide extracts and cereal grain residues. J. Agric. Food. Chem. 2008, 56:1720-1726.
66. Sila D.N., Buggenhout S.V., Duvetter T., Fraeye I., de Roeck A., Loey A.V., et al. Pectins in processed fruits and vegetables: part II - structure-function relationships. Compr. Rev. Food Sci. Food Saf. 2009, 8:86-104.
67. Singh D.P., Liu L.H., Øiseth S.K., Beloy J., Lundin L., Gidley M.J., et al. Influence of boron on carrot cell wall structure and its resistance to fracture. J. Agric. Food. Chem. 2010, 58:9181-9189.
68. Singh A., Sabally K., Kubow S., Donnelly D.J., Gariepy Y., Orsat V. Raghavan GSV. Microwave-assisted extraction of phenolic antioxidants from potato peels. Molecules 2011, 16:2218-2232.
69. Saulnier L., Thibault J.F. Ferulic acid and diferulic acids as components of sugar-beet pectins and maize bran heteroxylans. J. Sci. Food Agric. 1999, 79:396-402.
70. Smith M.M., Hartley R.D. Occurance and nature of ferulic acid substitution of cell-wall polysaccharides in graminaceous plants. Carbohydr. Res. 1983, 118:65-80.
71. Selinheimo E., Lampila P., Mattinen M.L., Buchert J. Formation of protein-oligosaccharide conjugates by laccase and tyrosinase. J. Agric. Food. Chem. 2008, 56:3118-3128.
72. Takei T., Sugihara K., Ijima H., Kawakami K. In situ gellable sugar beet pectin via enzyme-catalyzed coupling reaction of feruloyl groups for biomedical applications. J. Biosci. Bioeng. 2011, 112:491-494.
73. Tanhatan-Nasseri A., Crépeau M.J., Thibault J.F., Ralet M.C. Isolation and characterization of model homogalacturonans of tailored methylesterification patterns. Carbohydr. Polym. 2011, 86:1236-1243.
74. Tahiri M., Pellerin P., Tressol J.C., Doco T., Pepin D., Rayssiguier Y., et al. The rhamnogalacturonan-II dimer decreases intestinal absorption and tissue accumulation of lead in rats. J. Nutr. 2000, 130:249-253.
75. Thibault J.F., Rombouts F.M. Effect of some oxidizing agents, especially ammonium peroxysulfate, on sugar-beet pectins. Carbohydr. Res. 1986, 154:205-215.
76. Thurston C.F. The structure and function of fungal laccases. Microbiology 1994, 140:19-26.
77. Thompson J.E., Fry S.C. Evidence for covalent linkage between xyloglucan and acidic pectins in suspension-cultured rose cells. Planta 2000, 211:275-286.
78. Voragen A.G.J., Coenen G.J., Verhoef R.P., Schols H.A. Pectin, a versatile polysaccharide present in plant cell walls. Struct. Chem. 2009, 20:263-275.
79. Vansteenkiste E., Babot C., Rouau X., Micard V. Oxidative gelation of feruloylated arabinoxylan as affected by protein. Influence on protein enzymatic hydrolysis. Food Hydrocolloids 2004, 18:557-564.
80. Waldron K.W., Parker M.L., Smith A.C. Plant cell walls and food quality. Compr. Rev. Food Sci. Food Saf. 2003, 2:101-119.
81. Willats W.G.T., Knox J.P., Mikkelsen J.D. Pectin: new insights into an old polymer are starting to gel. Trends Food Sci. Technol. 2006, 17:97-104.
82. Whitcombe A.J., O'Neill M.A., Steffan W., Albersheim P., Darvill A.G. Structural characterization of the pectic polysaccharide, rhamnogalacturonan-II. Carbohydr. Res. 1995, 271:15-29.
83. Willats W.G.T., Orfila C., Marcus S.E., Knox J.P., Limberg G., Tmie Christensen, et al. Modulation of the degree and pattern of methyl-esterification of pectic homogalacturonan in plant cell walls: Implications for pectin methyl esterase action, matrix properties, and cell adhesion. J. Biol. Chem. 2001, 276:19404-19413.
84. Wicker L., Ackerley J.L., Hunter J.L. Modification of pectin by pectinmethylesterase and the role in stability of juice beverages. Food Hydrocolloids 2003, 17:809-814.
85. Wu M.C., Chen Y.W., Hwang J.Y., Lee B.H., Chang H.M. Transacylation of citrus pectin as catalyzed by pectinesterase from tendril shoots of chayote [Sechium edule (Jacq.) Swartz]. Food Res. Int. 2004, 37:759-765.
86. Waldron K.W., Parr A.J., Ng A., Ralph J. Cell wall esterified phenolic dimers: Identification and quantification by reverse phase high performance liquid chromatography and diode array detection. Phytochem. Anal. 1996, 7:305-312.
87. Yoo S.H., Fishman M.L., Savary B.J., Atj Hotchkiss Monovalent salt-induced gelation of enzymatically deesterified pectin. J. Agric. Food. Chem. 2003, 51:7410-7417.
88. Yoo S.H., Lee B.H., Savary B.J., Lee S., Lee H.G., Hotchkiss A.T. Characteristics of enzymatically-deesterified pectin gels produced in the presence of monovalent ionic salts. Food Hydrocolloids 2009, 23:1926-1929.
89. Yoo Y.H., Lee S., Kim Y., Kim K.O., Kim Y.S., Yoo S.H. Functional characterization of the gels prepared with pectin methylesterase (PME)-treated pectins. Int. J. Biol. Macromol. 2009, 45:226-230.
90. Zaidel D.N.A., Arnous A., Holck J., Meyer A.S. Kinetics of enzyme-catalyzed cross-linking of feruloylated arabinan from sugar beet. J. Agric. Food. Chem. 2011, 59:11598-11607.
91. Zaidel D.N.A., Chronakis I.S., Meyer A.S. Enzyme catalyzed oxidative gelation of sugar beet pectin: Kinetics and rheology. Food Hydrocolloids 2012, 28:130-140.
92. Zeeb B., Gibis M., Fischer L., Weiss J. Crosslinking of interfacial layers in multilayered oil-in-water emulsions using laccase: characterization and pH-stability. Food Hydrocolloids 2012, 27:126-136.