Functional oligosaccharides: production, properties and applications

  • Seema Patel
  • Arun Goyal
Original Paper


Worldwide interest in oligosaccharides has been increasing ever since they were accorded the prebiotic status. The oligosaccharides of various origin like, bacteria, algae, fungi and higher plants have been used extensively both as food ingredients and pharmacological supplements. The non-digestible oligosaccharides have been implicated as dietary fibre, sweetener, weight controlling agent and humectant in confectioneries, bakeries and breweries. Functional oligosaccharides have been found effective in gastrointestinal normal flora proliferation and pathogen suppression, dental caries prevention, enhancement of immunity, facilitation of mineral absorption, source of antioxidant, antibiotic alternative, regulators of blood glucose in diabetics and serum lipids in hyperlipidemics. Apart from the pharmacological applications, oligosaccharides have found use in drug delivery, cosmetics, animal and fishery feed, agriculture, etc. Keeping in view the importance of the functional oligosaccharides, we present an overview of their natural sources, types, structures, physiological properties. Conventional as well as novel synthesis, purification and analysis methods are summarized. Recent promising developments in this area are presented to facilitate their further exploitation.


Oligosaccharides Functional food Prebiotics Probiotics Microbiota 


  1. Adachi M, Vallee R (2002) Recent research on glycolipid. New effects of oligosaccharides from brown seaweed. Fragr J 30:73–83Google Scholar
  2. Astray G, Gonzalez-Barreiro C, Mejuto JC, Rial-Otero R, Simal-Gandara J (2009) A review on the use of cyclodextrins in foods. Food Hydrocolloids 23:1631–1640CrossRefGoogle Scholar
  3. Bardi L, Ricci R, Marzona M (2003) In situ bioremediation of a hydrocarbon polluted site with cyclodextrin as a coadjuvant to increase bioavailability. Water Air Soil Pollut Focus 3:15–23CrossRefGoogle Scholar
  4. Carvalheiro F, Esteves MP, Parajó JC, Pereira H, Gírio FM (2004) Production of oligosaccharides by autohydrolysis of brewery’s spent grain. Bioresour Technol 91:93–100CrossRefGoogle Scholar
  5. Chen HL, Lu YH, Lin J, Ko LY (2000) Effects of fructooligosaccharide on bowel function and indicators of nutritional status in constipated elderly men. Nutr Res 20:1725–1733CrossRefGoogle Scholar
  6. Chung HK, Bae EK, Ji HJ, Hwang JS, Park DW, Kim JE, Jung HJ, Choi HJ, Lee DS, Youn HJ (2003) An oligosaccharide fraction from Korean mugwort herb suppresses death of the mouse thymocytes in culture by down-regulating the Fas death receptor gene. Biotechnol Lett 25:1549–1553CrossRefGoogle Scholar
  7. Cmelik R, Chmelik J (2010) Structural analysis and differentiation of reducing and nonreducing neutral model starch oligosaccharides by negative-ion electrospray ionization ion-trap mass spectrometry. Int J Mass Spectrom 291:33–40CrossRefGoogle Scholar
  8. Cote GL (2009) Acceptor products of alternansucrase with gentiobiose. Production of novel oligosaccharides for food and feed and elimination of bitterness. Carbohydr Res 344:187–190CrossRefGoogle Scholar
  9. Courtois J (2009) Oligosaccharides from land plants and algae: production and applications in therapeutics and biotechnology. Curr Opin Microbiol 12:261–273CrossRefGoogle Scholar
  10. Crittenden RG, Playne MJ (1996) Production, properties and applications of food-grade oligosaccharides. Trends Food Sci Technol 71:353–361CrossRefGoogle Scholar
  11. Dias LG, Veloso ACA, Correia DM, Rocha O, Torres D, Rocha I (2009) UV spectrophotometry method for the monitoring of galacto-oligosaccharides production. Food Chem 113:246–252CrossRefGoogle Scholar
  12. Dimitroglou A, Merrifield DL, Spring P, Sweetman J, Moate R, Davies SJ (2010) Effects of mannan oligosaccharide (MOS) supplementation on growth performance, feed utilisation, intestinal histology and gut microbiota of gilthead sea bream (Sparus aurata). Aquaculture 300:182–188CrossRefGoogle Scholar
  13. Dodziuk H (2006) Cyclodextrins and their complexes. Wiley-VCH Verlag GmbH & Co., KGaA, WeinheimCrossRefGoogle Scholar
  14. Du YZ, Wang L, Yuan H, Wei XH, Hu FQ (2009) Preparation and characteristics of linoleic acid-grafted chitosan oligosaccharide micelles as a carrier for doxorubicin. Colloids Surf B Biointerfaces 69:257–263CrossRefGoogle Scholar
  15. Ebrahimi M, Placido L, Engel L, Ashaghi KS, Czermak P (2010) A novel; ceramic membrane reactor system for the continuous enzymatic synthesis of oligosaccharides. Desalination 250:1105–1108CrossRefGoogle Scholar
  16. Eseceli H, Demir E, Degirmencioglu N, Bilgic M (2010) The effects of Bio-Mos® mannan oligosaccharide and antibiotic growth promoter performance of broilers. J Anim Vet Adv 9:392–395CrossRefGoogle Scholar
  17. Fey PD, Safranek TJ, Rupp ME, Dunne EF, Ribot E, Iwen PC, Bradford PA, Angulo FJ, Hinrichs SH (2000) Ceftriaxone-resistant salmonella infection acquired by a child from cattle. New Engl J Med 342:1242–1249CrossRefGoogle Scholar
  18. Fric P (2007) Probiotics and prebiotics—renaissance of a therapeutic principle. Cent Eur J Med 2:237–270CrossRefGoogle Scholar
  19. Fujimoto Y, Hattori T, Uno S, Murata T, Usui T (2009) Enzymatic synthesis of gentiooligosaccharides by transglycosylation with β-glycosidases from Penicillium multicolour. Carbohydr Res 344:972–978CrossRefGoogle Scholar
  20. Funane F, Terasawa K, Mizuno Y, Ono H, Miyagi T, Gibu T, Tokashiki S, Kawabata Y, Kim YM, Kimura A, Kobayashi M (2007) A novel cyclic isomaltooligosaccharide (cycloisomaltodecaose, CI-10) produced by Bacillus circulans T-3040 displays remarkable inclusion ability compared with cyclodextrins. J Biotechnol 130:439–445CrossRefGoogle Scholar
  21. Gambarini AG, Miyamoto CA, Lima GA, Nader HB, Dietrich CP (1993) Mitogenic activity of acidic fibroblast growth factor is enhanced by highly sulfated oligosaccharides derived from heparin and heparan sulphate. Mol Cell Biochem 124:121–129CrossRefGoogle Scholar
  22. Goulas AK, Kapasakalidis PG, Sinclair HR, Rastall RA, Grandison AS (2002) Purification of oligosaccharides by nanofiltration. J Memb Sci 209:321–335CrossRefGoogle Scholar
  23. Goulas A, Tzortzis G, Gibson GR (2007) Development of a process for the production and purification of α- and β-galactooligosaccharides from Bifidobacterium bifidum NCIMB 41171. Int Dairy J 17:648–656CrossRefGoogle Scholar
  24. Gullon P, Moura P, Esteves MP, Girio FM, Dominguez H, Parajo JC (2008) Assessment on the fermentability of xylooligosaccharides from rice husks by probiotic bacteria. J Agric Food Chem 56:7482–7487CrossRefGoogle Scholar
  25. Hosomi O, Misawa Y, Takeya A, Matahira Y, Sugahara K, Kubohara Y, Yamakura Y, Kudo S (2009) Novel oligosaccharide has suppressive activity against human leukemia cell proliferation. Glycoconj J 26:189–198CrossRefGoogle Scholar
  26. Hu B, Gong Q, Wang Y, Ma Y, Li J, Yu W (2006) Prebiotic effects of neoagaro-oligosaccharides prepared by enzymatic hydrolysis of agarose. Food Microbiol 12:260–266Google Scholar
  27. Iliev I, Vassileva T, Ignatova C, Ivanova I, Haertle T, Monsan P, Chobert JM (2008) Gluco-oligosaccharides synthesized by glucosyltransferases from constitutive mutants of Leuconostoc mesenteroides strain Lm 28. J Appl Microbiol 104:243–250Google Scholar
  28. Iwata H, Yana S, Nasu M, Yosue T (2005) Effects of chitosan oligosaccharides on the femur trabecular structure in ovariectomized rats. Oral Radiol 21:19–22CrossRefGoogle Scholar
  29. Johnstone KD, Karoli T, Liu L, Dredge K, Copeman E, Li CP, Davis K, Hammond E, Bytheway I, Kostewicz E, Chiu FC, Shackleford DM, Charman SA, Charman SA, Charman WN, Harenberg J, Gonda TJ, Ferro V (2010) Synthesis and biological evaluation of polysulfated oligosaccharide glycosides as inhibitors of angiogenesis and tumor growth. J Med Chem 53:1686–1699CrossRefGoogle Scholar
  30. Katapodis P, Christakopoulos P (2008) Enzymatic production of feruloyl xylo-oligosaccharides from corn cobs by a family 10 xylanase from Thermoascus aurantiacus. LWT Food Sci Technol 41:1239–1243CrossRefGoogle Scholar
  31. Kim YS, Park CS, Oh DK (2006) Lactulose production from lactose and fructose by a thermostable β-galactosidase from Sulfolobus solfataricus. Enzyme Microb Technol 39:903–908CrossRefGoogle Scholar
  32. Kolida S, Gibson GR (2007) Inulin and oligofructose: health benefits and claims—a critical review. Am Soc Nutr 137:2503–2506Google Scholar
  33. Kong F (2007) Recent studies on reaction pathways and applications of sugar orthoesters in synthesis of oligosaccharides. Carbohydr Res 342:345–373CrossRefGoogle Scholar
  34. Li XJ, Piao XS, Kim SW, Liu P, Wang L, Shen YB, Jung SC, Lee HS (2007) Effects of chito-oligosaccharide supplementation on performance, nutrient digestibility, and serum composition in broiler chickens. Poult Sci 86:1107–1114Google Scholar
  35. Li KY, Lai P, Lu S, Fang YT, Chen HH (2008) Optimization of acid hydrolysis conditions for feruloylated oligosaccharides from rice bran through response surface methodolgy. J Agric Food Chem 56:8975–8978CrossRefGoogle Scholar
  36. Li T, Li S, Du L, Wang N, Guo M, Zhang J, Yan F, Zhang H (2010) Effects of haw pectic oligosaccharide on lipid metabolism and oxidative stress in experimental hyperlipidemia mice induced by high-fat diet. Food Chem 121:1010–1013CrossRefGoogle Scholar
  37. Liu HT, He JL, Li WM, Yang Z, Wang YX, Bai XF (2010) Chitosan oligosaccharides protect human umbilical vein endothelial cells from hydrogen peroxide-induced apoptosis. Carbohydr Polym. doi: 10.1016/j.carbpol.2010.01.025
  38. Madhukumar MS, Muralikrishna G (2010) Structural characterisation and determination of prebiotic activity of purified xylo-oligosaccharides obtained from Bengal gram husk (Cicer arietinum L.) and wheat bran (Triticum aestivum). Food Chem 118:215–223CrossRefGoogle Scholar
  39. Mahious AS, Gatesoupe FJ, Hervi M, Metailler R, Ollevier F (2006) Effect of dietary inulin and oligosaccharides as prebiotics for weaning turbot, Psetta maxima (Linnaeus, C. 1758). Aquac Int 14:219–229CrossRefGoogle Scholar
  40. Majumder A, Mangtani A, Patel S, Shukla R, Goyal A (2009) Gluco-oligosaccharides production from glucan of Leuconostoc mesenteroides NRRL B-742 by microwave assisted hydrolysis. Curr Trends Biotechnol Pharm 3:405–411Google Scholar
  41. Minoru S, Yoshio I (2002) Recent research on glycolipid. The molecular mechanism of skin moisturizing effect adored by oligosaccharides. The unique properties of trehalose. Fragr J 30:15–21Google Scholar
  42. Mitsou EK, Panopoulou N, Turunen K, Spiliotis V, Kyriacou A (2010) Impact of a jelly containing short-chain fructo-oligosaccharides and Sideritis euboea extract on human faecal microbiota. Int J Food Microbiol 135:112–117CrossRefGoogle Scholar
  43. Miyazawa T, Funazukuri T (2006) Noncatalytic hydrolysis of guar gum under hydrothermal conditions. Carbohydr Res 341:870–877CrossRefGoogle Scholar
  44. Moure A, Gullon P, Domínguez H, Parajo JC (2006) Advances in the manufacture, purification and applications of xylo-oligosaccharides as food additives and nutraceuticals. Process Biochem 41:1913–1923CrossRefGoogle Scholar
  45. Murata T, Usui T (2002) Efficient synthetic method of obtaining oligosaccharide units and derivatives utilizing endoglycosidases. Biotechnol Bioprocess Eng 7:263–267CrossRefGoogle Scholar
  46. Mussatto SI, Mancilha IM (2007) Non-digestible oligosaccharides: a review. Carbohydr Polym 68:587–597CrossRefGoogle Scholar
  47. Nabarlatz D, Ebringerova A, Montane D (2007) Autohydrolysis of agricultural by-products for the production of xylo-oligosaccharides. Carbohydr Polym 69:20–28CrossRefGoogle Scholar
  48. Nacos MK, Katapodis P, Pappas C, Daferera D, Tarantilis PA, Christakopoulos P (2006) Kenaf xylan—a source of biologically active acidic oligosaccharides. Carbohydr Polym 66:126–134CrossRefGoogle Scholar
  49. Nakai H, Hachem MA, Petersen BO, Westphal Y, Mannerstedt K, Baumann MJ, Dilokpimol A, Schols HA, Duus JO, Svensson B (2010) Efficient chemoenzymatic oligosaccharide synthesis by reverse phosphorolysis using cellobiose phosphorylase and cellodextrin phosphorylase from Clostridium thermocellum. Biochimie PMID: 20678539Google Scholar
  50. Okada H, Fukushi E, Yamamori A, Kawazoe N, Onodera S, Kawabata J, Shiomi N (2010) Novel fructopyranose oligosaccharides isolated from fermented beverage of plant extract. Carbohydr Res 345:414–418CrossRefGoogle Scholar
  51. Pocedicova K, Curda L, Misun D, Dryakova A, Diblikova L (2010) Preparation of galacto-oligosaccharides using membrane reactor. J Food Eng. doi: 10.1016/j.jfoodeng.2010.02.001
  52. Qiang X, YongLie C, QianBing W (2009) Health benefit application of functional oligosaccharides. Carbohydr Polym 77:35–441CrossRefGoogle Scholar
  53. Quigley EMM (2010) Prebiotics and probiotics; modifying and mining the microbiota. Pharmacol Res 61:213–218CrossRefGoogle Scholar
  54. Raman R, Raguram S, Venkataraman G, Paulson JC, Sasisekharan R (2005) Glycomics: an integrated systems approach to structure–function relationships of glycans. Nat Methods 2:817–824CrossRefGoogle Scholar
  55. Rao MS, Chander R, Sharma A (2008) Synergistic effect of chitooligosaccharides and lysozyme for meat preservation. LWT Food Sci Tehnol 4:1995–2001CrossRefGoogle Scholar
  56. Roberfroid M, Slavin J (2000) Nondigestible oligosaccharides. Crit Rev Food Sci Nutr 40:461–480CrossRefGoogle Scholar
  57. Rose DJ, Inglett GE (2010) Two-stage hydrothermal processing of wheat (Triticum aestivum) bran for the production of feruloylated arabinoxylooligosaccharides. Agric Food Chem 58:6427–6432CrossRefGoogle Scholar
  58. Sánchez O, Guio F, Garcia D, Silva E, Caicedo L (2008) Fructooligosaccharides production by Aspergillus sp. N74 in a mechanically agitated airlift reactor. Food Bioproducts Eng 86:109–115CrossRefGoogle Scholar
  59. Savic IM, Nikolic GS, Savic, IM, Cakic MD (2010) Conductometric studies on the stability of copper complexes with different oligosaccharides. Central Eur J Chem. doi: 10.2478/s11532-010-0082-3
  60. Thakur M, Dixit VK (2008) Ameliorative effect of fructo-oligosaccharide rich extract of Orchis latifolia Linn. on sexual dysfunction in hyperglycemic male rats. Sex Disabil 26:37–46CrossRefGoogle Scholar
  61. Thammarutwasik P, Hongpattarakere T, Kijroongrojana S, Kijroongrojana K, Itharat A, Reanmongkol W (2009) Prebiotics: a review. Songklanakarin. J Sci Technol 31:401–408Google Scholar
  62. Tuohy KM, Rouzaud GC, Bruck WM, Gibson GR (2005) Modulation of the human gut microflora towards improved health using prebiotics-assessment of efficacy. Curr Pharm Des 11:75–90CrossRefGoogle Scholar
  63. Van Laere KMJ, Hartemink R, Bosveld M, Schols HA, Voragen AGJ (2000) Fermentation of plant cell wall derived polysaccharides and their corresponding oligosaccharides by intestinal bacteria. J Agric Food Chem 48:1644–1652CrossRefGoogle Scholar
  64. Vanhulle S, Radman R, Parra R, Cui T, Bols C-M, Tron T, Sannia G, Tajalli Keshavarz K (2007) Effect of mannan oligosaccharides elicitor and ferulic acid on enhancement of laccase production in liquid cultures of basidiomycetes. Enzyme Microb Technol 40:1712–1718CrossRefGoogle Scholar
  65. Villamiel M, Corzo N, Foda MI, Montes F, Olano A (2002) Lactulose formation catalysed by alkaline-substituted sepiolites in milk permeate. Food Chem 76:7–11CrossRefGoogle Scholar
  66. Weijers CAGM, Franssen MCR, Visser GM (2008) Glycosyltransferase-catalyzed synthesis of bioactive oligosaccharides. Biotechnol Adv 26:436–456CrossRefGoogle Scholar
  67. Westphal Y, Kuhnel S, de Waard P, Schols SWA, Schols HA, Voragen AGJ, Gruppen H (2010) Branched arabino-oligosaccharides isolated from sugar beet arabinan. Carbohydr Res. doi: 10.1016/j.carres.2010.03.042
  68. Wichienchot S, Jatupornpipat M, Rastall RA (2010) Oligosaccharides of pitaya (dragon fruit) flesh and their prebiotic properties. Food Chem 120:850–857CrossRefGoogle Scholar
  69. Wu SC, Wen TN, Pan CL (2005) Algal-oligosaccharide-lysates prepared by two bacterial agarases stepwise hydrolyzed and their anti-oxidative properties. Fish Sci 71:1149–1159CrossRefGoogle Scholar
  70. Yun JW, Choi YJ, Song CH, Song SK (1999) Microbial production of inulo-oligosaccharides by an endoinulinase from Pseudomonas sp. expressed in Escherichia coli. J Biosci Bioeng 87:291–295CrossRefGoogle Scholar
  71. Zokaee F, Kaghazchi T, Zare A, Soleimani M (2002) Isomerization of lactose to lactulose-study and comparison of three catalytic systems. Process Biochem 37:629–635CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2010

Authors and Affiliations

  1. 1.Department of BiotechnologyIndian Institute of Technology GuwahatiGuwahatiIndia

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