Oligosaccharides engineering from plants and algae applications in biotechnology and therapeutics

Minerva Biotecnologica

Volumn 17, Issue 3, 2005, Pages 107-117

  Delattre, C ^a   Michaud, Philippe ^a   Courtois, B ^a   Courtois, J ^a  

^a UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

Author keywords

Algae; Biotechnology; Elicitors; Oligosaccharides; Plant cell wall polysaccharides; Polysaccharides cleavage; Prebiotics

Indexed keywords

ALGINIC ACID; ARABINOSE DERIVATIVE; BETA 1,3 GLUCAN; BETA 1,6 GLUCAN; CARBOHYDRATE DERIVATIVE; CARRAGEENAN; CYCLODEXTRIN; FRUCTOSE; FUCOIDIN; GALACTAN; GALACTOSE; GALACTURONIC ACID; GLYCOSAMINOGLYCAN; HEPARIN; IMMUNOMODULATING AGENT; ISOMALTOSE; LAMINARAN; MALTOSE; MANNAN; OLIGOSACCHARIDE; OLIGOSACCHARIN DERIVATIVE; PECTIN; PLANT EXTRACT; POLYSACCHARIDE; PROBIOTIC AGENT; RHAMNOSE; SACCHARIN DERIVATIVE; ULVAN; UNCLASSIFIED DRUG; UNINDEXED DRUG; XYLOSE;

ALGA; BIOMEDICAL ENGINEERING; DEPOLYMERIZATION; DRUG HYDROLYSIS; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME DEGRADATION; GLYCOSYLATION; HERBAL MEDICINE; MEDICINAL PLANT; MICROWAVE IRRADIATION; NONHUMAN; PLANT BIOTECHNOLOGY; RADIOLYSIS; REGULATORY MECHANISM; REVIEW; ULTRASOUND; ULTRAVIOLET IRRADIATION;

ALGAE;

EID: 27744443026     PISSN: 11204826     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (108)

1. Nugent MA. Heparin sequencing brings structure to the function of complex oligosaccharides. Proc Natl Acad Sci U S A 2000;97:10301-3.
2. Lauder RM, Huckerby TN, Nieduszynski IA. A fingerprinting method for chondroitin/dermatan sulfate and hyaluronan oligosaccharides. Glycobiology 2000;10:393-401.
3. Albersheim P, Darvill A, Augur C, Cheong J, Eberhard S, Hahn MG et al. Oligosaccharins: oligosaccharide regulatory molecules. Acc Chem Res 1992;25:77-83.
4. Ryan CA, Farmer EE. Oligosaccharide signals in plants: a current assessment. Annu Rev Plant Physiol 1991;42:651-74.
5. John M, Röhrig H, Schmidt J, Walden R, Schell J. Cell signalling by oligosaccharides. Trends Plant Sci 1997;2:111-5.
6. Spaink HP. Root nodulation and infection factors produced by rhizobial bacteria. Annu Rev Microbiol 2000;54:257-88.
7. Dinan E, Excoffier G, Liénart Y, Vignon MR. Two rhamnogalacturonide tetrasaccharides isolated from semi-retted flax fibers are signaling molecules in Rubus fruticosus L. cells. Plant Physiol 1997;115:793-801.
8. Patier P, Potin P, Rochas C, Kloareg B, Yvin JC, Liņart Y. Free or silica bound oligokappa carrageenans elicit laminarinase activity in Rubus cells and protoplasts. Plant Sci 1995;110:27-35.
9. Potin P, Bouarab K, Küpper F, Kloareg B. Oligosaccharide recognition signals and defense reactions in marine plant-microbe interactions. Curr Opin Microbiol 1999;2:276-83.
10. Küpper FC, Kmoareg B, Guerne J, Potin P. Oligoguluronates elicit an oxidative burst in the brown algal kelp Laminaria digitata. Plant Physiol 2001;125:278-91.
11. Painter TJ. Carbohydrate polymers in desert reclamation: the potential of microalgal biofertilizers. Carbohydr Polym 1993;20:77-86.
12. Patier P, Yvin JC, Kloareg B, Lienart Y, Rochas C. Seaweed liquid fertilizer from Ascophyllum nodosum contains elicitors of plant D-glycanases. J Appl Phycol 1993;5:343-9.
13. Natsume M, Kamo Y, Hirayama M, Adachi T. Isolation and characterization of alginate-derived oligosaccharides with root growth-promoting activities. Carbohydr Res 1994;258:187-97.
14. Sharp JK, Valent B, Albersheim P. Purification and partial characterization of a ,-glucan fragment that elicits phytoalexin accumulation in soybean. J Biol Chem 1984;259:11312-20.
15. Brady KP, Darvill AG, Albersheim P. Activation of a Tobacco glycin-rich protein gene by a fungal glucan preparation. Plant J 1993;4:517-24.
16. Kopp M, Rouster J, Fritig B, Darvill A, Albersheim P. Host pathogen interactions: XXXII. A fungal glucan preparation protects Nicotianae against infection by viruses. Plant Physiol 1989;90:208-16.
17. Cheong JJ, Birberg W, Fügedi P, Pilotti A, Garegg PJ, Hong N et al. Structure-activity relationships of oligo-β-glucoside elicitors of phytoalexin accumulation in soybean. Plant Cell 1991; 3:127-36.
18. Cosio EG, Feger M, Miller CJ, Antelo L, Ebel J. High-affinity binding of fungal ,-glucan elicitors to cell membranes of species of the plant family Fabaceae. Planta 1996;200:92-9.
19. Côté F, Roberts K, Hahn M. Identification of high-affinity binding sites for the hepta-,-glucoside elicitor in membranes of the model legumes Medicago truncatula and Lotus japonicus. Planta 2000;211:596-605.
20. Klarzynski O, Plesse B, Joubert JM, Yvin JC, Kopp M, Kloareg B et al. Linear ,-1,3 glucans are elicitors of defense responses in Tobacco. Plant Physiol 2000;124:1027-38.
21. Eberhard S, Doubrava N, Marfà V, Mohnen D, Southwick A, Albersheim P et al. Pectic cell wall fragments regulate tobacco thin-cell-layer explant morphogenesis. Plant Cell 1989;1:747-55.
22. Côté F, Ham KS, Hahn MG, Bergman CW. Oligosaccharides elicitors in host-pathogen interactions: generation, perception, and signal transduction. In: Biswas, BB, Das H, editors. Subcellular biochemistry. Vol. 29. Plant-microbe interactions. New York: Plenum Press; 1998.p.385-431.
23. Reymond P, Kunz B, Paul-Pletzer K, Grimm R, Eckerskorn C, Farmer EE. Cloning of a cDNA encoding a plasma membrane-associated, uronide binding phosphoprotein with physical properties similar to viral movement proteins. Plant Cell 1996;8:2265-76.
24. Moerschbacher BM, Mierau M, Graebner B, Noll U, Mort AJ. Small oligomers of galacturonic acid are endogenous suppressors of disease resistance reactions in wheat leaves. J Exp Bot 1999;50:605-12.
25. Asiegbu FO, Daniel G, Johansson M. Defense related reactions of seedling roots of Norway pruce to infection by Heterobasidion annosum (Fr.). Bref Physiol Mol Plant Pathol 1994;45:1-19.
26. Low PS, Merdida JR. The oxidative burst in plant defense: function and signal transduction. Physiol Plant 1996;96:533-42.
27. Lee S, Choi H, Suh SS, Doo IS, Oh KY, Choi E et al. Oligogalacturonic acid and chitosan reduce stomatal aperture by inducing the evolution of reactive oxygen species from guard cells of tomato and Commelina communis. Plant Physiol 1999;121:147-52.
28. Ridley BL, O'Neill MA, Mohnen D. Pectins: structure, biosynthesis, and oligogalacturonide-related signaling. Phytochemistry 2001;57:929-67.
29. Côté F, Hahn MG. Oligosaccharins: structure and signal transduction. Plant Mol Biol 1994;12:1379-411.
30. Bergey DR, Orozco-Cardenas M, de Moura DS, Ryan CA. A wound- and systemin-inducible polygalacturonase in tomato leaves. Proc Natl Acad Sci U S A 1999;96:1756-60.
31. Navazio L, Moscatiello R, Bellincampi D, Baldan B, Meggio F, Brini M et al. The role of calcium in oligogalacturonide-activated signalling in soybean cells. Planta 2002;215:596-605.
32. Jin DF, West CA. Characteristics of galacturonic acid oligomers as elicitors of casbene synthetase activity in castor bean seedling. Plant Physiol 1984;74:989-92.
33. Spiro MD, Ridley BL, Eberhard S, Kates KA, Mathieu Y, O'Neill MA et al. Biological activity of reducing-end-derivatized oligogalacturonides in tobacco tissue cultures. Plant Physiol 1998;116:1289-98.
34. Komae K, Komae A, Misaki A. A 4,5-unsaturated low molecular weight oligogalacturonide as a potent phytoalexin-elicitor isolated from polygalacturonide of Ficus awkeotsang. Argic Biol Chem 1990;54:1477-84.
35. Marfà V, Gollin D, Eberhard S, Mohnen D, Albersheim P, Darvill A. Oligogalacturonides are able to induce flowers to form on tobacco explants. Plant J 1991;1:217-25.
36. Ariyo TA, Bucke C, Keshavarz T. Enhanced penicillin production by oligosaccharides from batch cultures of Penicillium chrysogenum in stirred-tank reactors. FEMS Microbiol Lett 1998;166:165-70.
37. Ariyo TA, Bucke C, Keshavarz T Alginate oligosaccharides as enhancers of penicillin production in cultures of Penicillium chrysogenum. Biotechnol Bioeng 1997;53:17-20.
38. Liu G, Casqueiro J, Gutierrez S, Kosalkova K, Castillo NI, Martin JF. Elicitation of penicillin biosynthesis by alginate in Penicillium chrysogenum, exerted on pcbAB, pcbC, and penDE genes at the transcriptional level. J Microbiol Biotechnol 2001;11:812-8.
39. Asilonu E, Bucke C, Keshavarz T. Enhancement of chrysogenin production in cultures of Penicillium chrysogenum by uronic acid oligosaccharicles. Biotechnol Lett 2000;11:931-6.
40. Petruccioli M, Federic F, Bucke C, Keshavarz T. Enhancement of glucose oxidase production by Penicillium variabile P16. Enzyme Microb Technol 1999;24:397-401.
41. Rastall RA, Gibson GR. Prebiotic oligosaccharides: evaluation of biological activities and potential future developments. In: Tannock GW, editor. Probiotics and prebiotics: where are we going? Norwich, UK: Caister Academic Press; 2002.p.107-48.
42. Rycroft CE, Jones MR, Gibson GR, Rastall RA. A comparative in vitro evaluation of the fermentation properties of prebiotic oligosaccharides. J Appl Microbiol 2001;91:878-87.
43. De Boever P, Deplancke B, Verstraete W. Fermentation by gut microbiota cultured in a simulator of the human intestinal microbiol ecosystem is improved by supplementing a soygerm powder. J Nutr 2000;130:2599-606.
44. Olano-Martin E, Mountzouris KC, Gibson GR, Rastall RA. Continuous production of oligosaccharides from pectin in an enzyme membrane reactor. J Food Sci 2001;66:966-71.
45. Olano-Martin E, Gibson GR, Rastall RA. Comparison of the in vitro bifidogenic properties of pectins and pectic-oligosaccharides. J Appl Microbiol 2002;93:505-11.
46. Oosterveld A, Beldman G, Voragen AGJ. Enzymatic modification of pectic polysaccharides obtained from sugar beet pulp. Carbohydr Polym 2002;48:73-81.
47. Pineo GF, Hull RD. Low-molecular-weight heparin: prophylaxis and treatment of venous thromboembolism. Annu Rev Med 1997;48: 79-91.
48. Liu J, Shriver Z, Pope RM, Thorp SC, Duncan MB, Copeland RJ et al. Characterization of a heparan sulfate octasaccharide that binds to Herpes Simplex virus type 1 glycoprotein D. J Biol Chem 2002; 277:33456-67.
49. Ghatak S, Misra S, Toole BP. Hyaluronan oligosaccharides inhibit anchorage-independent growth of tumor cells by suppressing the phosphoinositide 3-kinase/Akt cell survival pathway. J Biol Chem 2002;277:38013-20.
50. Berteau O, Mulloy B. Sulfated fucans, fresh perspectives: structures, functions, and biological properties of sulphated fucans and an overview of enzymes active toward this class of polysaccharide. Glycobiology 2003;13:29R-40R.
51. Farias WRL, Valente AP, Pereira MS, Mourao PAS. Structure and anticoagulant activity of sulphated galactans: isolation of a unique sulphated galactan from the red algae Botryocladia occidentalis and comparison of its anticoagulant action with that of sulphated galactans from invertebrates. J Biol Chem 2000;275:29299-307.
52. Otterlei M, Østgaard K, Skjåk-Bræk G, Smidsrød O, Soon-Shiong P, Espevik T. Induction of cytokineproduction from human monocytes stimulated with alginate. J. Immunother 1991;10:286-91.
53. Hricovini M, Guerrini M, Bisio A. Structure of heparin-derived tetrasaccharide complexed to the plasma protein antithrombin derived from NOEs, J-couplings and chemical shifts. Eur J Biochem 1999;261:789-801.
54. Iwamoto Y, Xu X, Tamura T, Oda T, Muramatsu T. Enzymatically depolymerized alginate oligomers that cause cytotoxic cytokine production in human mononuclear cells. Biosci Biotech Biochem 2003;67:258-63.
55. Wong TY, Preston LA, Schiller NL. Alginate lyase: review of major sources and enzymes characteristics, structure-function analysis, biological roles and applications. Annu Rev Microbiol 2000;54:289-340.
56. Kawada A, Hiura N, Tajima S, Takahara H. Alginate oligosaccharides stimulate VEGF-mediated growth and migration of human endothelial cells. Arch Dermatol Res 1999;291:542-7.
57. Bland EJ, Keshavarz T, Bucke C. The influence of small oligosaccharides on the immune system. Carbohyd Res 2004;339:1673-8.
58. Nardella A, Chaubet F, Boisson-Vidal C, Blondin C, Durand P, Jozefonvicz J. Anticoagulant low molecular wt. fucans produced by radical process and ion exchange chromatography of high molecular weight fucans extracted from the brown seaweed Ascophyllum nodosum. Carbohyd Res 1996;289:201-8.
59. Teleman A, Lundqvist J, Tjerneld F, Stalbrand H, Dahlman O. Characterization of acetylated 4-O-methylglucuronoxylan isolated from aspen employing 1H and 13C NMR spectroscopy. Carbohydr Res 2000;329:807-15.
60. Jacobs A, Lundqvist J, Stalbrand H, Tjerneld F, Dahlman O. Characterization of water-soluble hemicelluloses from spruce and aspen employing SEC/MALDI mass spectroscopy. Carbohydr Res 2002;337:711-7.
61. Zhou G, Sun YP, Xin H, Zhang Y, Li Z, Xu Z. In vivo antitumor and immunomodulation activities of different molecular weight lambda-carrageenans from Chondrus ocellatus. Pharmacol Res 2004;50:47-53.
62. Pengzhan Y, Ning L, Xiguang L, Gefei Z, Quanbin Z, Pengcheng L. Antihyperlipidemic effects of different molecular weight sulfated polysaccharides from Ulva pertusa (Chlorophyta). Pharmacol Res 2003;48:543-9.
63. Ramani R, Ranganathaiah C. Degradation of acrylonitrile-butadiene-styrene and polycarbonate by UV irradiation. Polym Degrad Stabil 2000;69:347-54.
64. Wasikiewicz JM, Yoshii F, Nagasawa N, Wach RA, Mitomo H. Degradation of chitosan and sodium alginate by gamma radiation, sonochemical and ultraviolet methods. Radiat Phys Chem. In press 2004.
65. Jumel K, Harding SE, Mitchell JR. Effect of gamma irradiation on the macromolecular integrity of guar gum. Carbohydr Res 1996;282:223-36.
66. Bisio A, Guglieri S, Frigerio M, Torri G, Vismara E, Cornelli U et al. Controlled gamma-ray irradiation of heparin generates oligosaccharides enriched in highly sulfated sequences. Carbohydr Polym 2004;55:101-12.
67. Ebringerova A, Hromadkova Z. The effect of ultrasound on the structure and properties of the water-soluble corn hull heteroxylan. Ultrason Sonochem 1997;4:305-9.
68. Kardos N, Luche JL. Sonochemistry of carbohydrate compounds. Carbohydr Res 2001;332:115-31.
69. Tomasik P, Zaranyika MF. Nonconventional methods of modification of starch. Adv Carbohydr Chem Biochem 1995;51:243-320.
70. Lii CY, Chen CH, Yeh AI, Lai VMF. Preliminary study on the degradation kinetics of agarose and carrageenans by ultrasound. Food Hydrocoll 1999;13:477-81.
71. Hotchkiss AT Jr, Lecrinier SL, Hicks KB. Isolation of oligogalacturonic acids up to DP 20 by preparative high-performance anion-exchange chromatography and pulsed amperometric detection. Carbohydr Res 2001;324:135-40.
72. Simms PJ, Hotchkiss AT, Irwin PL, Hicks KB. High-performance liquid chromatographic separation of oligogalacturonic acids on a cyclomaltoheptaose (,-cyclodextrin) bonded-phase column. Carbohydr Res 1995;278:1-9.
73. Holme HK, Lindmo K, Kristiansen A, Smidsrød O. Thermal depolymerization of alginate in the solid state. Carbohydr Polym 2003;54:431-8.
74. Carvalheiro F, Esteves MP, Parajo JC, Pereira H, Girio FM. Production of oligosaccharides by autohydrolysis of brewery's spent grain. Bioresour Technol 2004;91:93-100.
75. Piskorz J, Majerski P, Radlein D, Vladars-Usas A, Scott DS. Flash pyrolysis of cellulose for production of anhydro-oligomers. J Anal Appl Pyrol 2000;56:145-66.
76. Cote GL, Willet JL. Thermomechanical depolymerization of dextran. Carbohydr Polym 1999;39:119-26.
77. Colliec S, Boisson-Vidal C, Jozefonvicz J. A low-molecular-weight fucoidan fraction from the brown seaweed Pelvetia canaliculata. Phytochemistry 1994;35:697-700.
78. Hjerde T, Kristiansen TS, Stokke BT, Smidsroed O, Christensen BE. Conformation-dependent depolymerization kinetics of polysaccharides studied by viscosity measurements. Carbohydr Polym 1994;24:265-75.
79. Renard CMGC, Lahaye M, Mutter M, Voragen FGJ, Thibault JF. Isolation and structural characterization of rhamnogalacturonan oligomers generated by controlled acid hydrolysis of sugar-beet pulp. Carbohydr Res 1998;305:271-80.
80. Shimokawa T, Yoshida S, Takeuchi T, Murata K, Ishii T, Kusakabe I. Preparation of two series of oligo-guluronic acids from sodium alginate by acid hydrolysis and enzymatic degradation. Biosci Biotech Biochem 1996;60:1532-4.
81. Ponder GR. Arabinogalactan from Western larch. Part IV. Polymeric products of partial acid hydrolysis. Carbohydr Polym 1998; 36: 1-14.
82. Ganter JLMS, Heyraud A, Petkowicz CLO, Rinaudo M, Reicher F. Galactomannans from Brazilian seeds: characterization of the oligosaccharides produced by mild acid hydrolysis. Int J Biol Macromol 1995;17:13-9.
83. Petkowicz CLO, Sierakowski MR, Ganter JIMS, Reicher F. Galactomannans and arabinans from seeds of Caesalpiniaceae. Phytochemistry 1998;49:737-43.
84. Vogl H, Paper DH, Franz G. Preparation of a sulfated linear (1,4)-β-D-galactan with variable degrees of sulfation. Carbohydr Polym 2000;41:185-90.
85. Campbell, AD, Labavitch JM. Induction and regulation of ethylene biosynthesis and ripening by pectic oligomers in tomato pericarp disks. Plant Physiol 1991;97:706-13.
86. Uchiyama H, Dobashi Y, Ohkouchi K, Nagasawa K. Chemical change involved in the oxidative reductive depolymerization of hyaluronic acid. J Biol Chem 1990;265:7753-9.
87. Miller AR. Oxidation of cell wall polysaccharides by hydrogen peroxide: a potential mechanism for cell wall breakdown in plants. Biochem Biophys Res Commun 1986;141:238-44.
88. Tabbi G, Fry SC, Bonomo RP. ESR study of the non-enzymic scission of xyloglucan by an ascorbate-H2O2-copper system: the involvement of the hydroxyl radical and the degradation of ascorbate. J Inorg Biochem 2001;84:179-87.
89. Hjerde T, Stokke BT, Smidsrød O, Bjørn EC. Free-radical degradation of triple-stranded scleroglucan by hydrogen peroxide and ferrous ions. Carbohydr Polym 1998;37:41-8.
90. Christensen BE, Myhr M, Smidsrød O. The degradation of xanthan by hydrogen peroxide in the presence of ferrous ions. Comparison to acid hydrolysis. Carbohydr Res 1996;280:85-99.
91. Colombini MP, Ceccarini A, Carmignani A. Ion chromatography characterization of polysaccharides in ancient wall paintings. J Chromatogr A 2002;968:79-88.
92. Marry M, Cavalier DM, Schnurr JK, Netland J, Yang Z, Pezeshk V et al. Structural characterization of chemically and enzymatically derived standard oligosaccharides isolated from partially purified tamarind xyloglucan. Carbohydr Polym 2003;51:347-56.
93. Reddy TT, Tammishetti S. Free radical degradation of guar gum. Polym Degrad Stabil 2004;86:455-9.
94. Michaud P, Da Costa A, Courtois B, Courtois J. Polysaccharide lyases: recent developments as biotechnological tools. Crit Rev Biotechnol 2003;23:233-66.
95. De Vries RP, Visser J. Aspergillus enzymes involved in degradation of plant cell wall polysaccharides. Microbiol Mol Biol Rev 2001;65:497-522.
96. Playne MJ, Crittenden RI. Commercially available oligosaccharides. Bulletin of the International Dairy Federation 1996;313:10-22.
97. Aldington S, Fry SC. Oligosaccharins. Adv Bot Res 1993;19:1-101.
98. Antonopoulos A, Favetta P, Helbert W, Lafosse M. Isolation of Î-oligosaccharides using ion-pair liquid chromatography-characterisation by electrospray ionisation mass spectrometry in positive-ion mode. Carbohydr Res 2004;339:1301-9.
99. Boons GJ. Strategies in oligosaccharides synthesis. Tetrahedron 1996;52:1095-121.
100. Magaud D, Grandjean C, Doutheau A, Anker D, Shevchik V, Cotte-Pattat N et al. An efficient and highly stereoselective (1?4) glycosylation between two-galacturonic acid ester derivatives. Tetrahedron Lett 1997;38:241-4.
101. Magaud D, Grandjean C, Doutheau A, Anker D, Shevchik V, Cotte-Pattat N et al. Synthesis of the two monomethyl esters of the disaccharide 4-O-galacturonosyl-galacturonic acid and of precursors for the preparation of higher oligomers methyl uronated in definite sequences. Carbohydr Res 1998;314:189-99.
102. Takeo K, Ohguchi Y, Hasegawa R, Kitamura S. Synthesis of (1,4)-β-D-xylo-oligosaccharides of dp 4-10 by a blockwise approach. Carbohydr Res 1995;278:301-13.
103. Hwang JK. Production of functional carbohydrates by the extrusion reactor. Food Sci Biotechnol 2001;10:455-9.
104. Sangeetha PT, Ramesh MN, Prapulla SG. Production of fructo-oligosaccharides by fructosyl transferase from Aspergillus oryzae CFR 202 and Aureobasidium pullulans CFR 77. Process Biochem 2004;39:753-8.
105. Czermak P, Ebrahimi M, Grau K, Netz S, Sawatzki G, Pfromm PH. Membrane-assisted enzymatic production of galactosyl-oligosaccharides from lactose in a continuous process. J Memb Sci 2004;232:85-91.
106. Nigam P, Singh D. Enzymes and microbial systems involved in starch processing. Enzyme Microb Technol 1995;17:770-8.
107. Thompson DO. Cyclodextrins-enabling excipients: their present and future use in pharmaceuticals. Crit Rev Ther Drug Carrier Syst 1997;14:1-104.
108. Sears P, Wong CH. Toward automated synthesis of oligosaccharides and glycoproteins. Science 2001;291:2344-50.