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any of the carbohydrates that yield only a few monosaccharide molecules on complete hydrolysis

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/04/21 08:18:23」(JST)

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An oligosaccharide (from the Greek oligos, a few, and sacchar, sugar) is a saccharide polymer containing a small number (typically two to ten^[1]) of simple sugars (monosaccharides). Oligosaccharides can have many functions; for example, they are commonly found on the plasma membrane of animal cells where they can play a role in cell–cell recognition.

In general, they are found either O- or 'f-linked to compatible amino acid side-chains in proteins or to lipid moieties (see glycans).

Examples

Fructo-oligosaccharides (FOS), which are found in many vegetables, consist of short chains of fructose molecules. (Inulin has a much higher degree of polymerization than FOS and is a polysaccharide.) Galactooligosaccharides (GOS), which also occur naturally, consist of short chains of galactose molecules. These compounds can be only partially digested by humans.

Oligosaccharides are often found as a component of glycoproteins or glycolipids and as such are often used as chemical markers, often for cell recognition. An example is ABO blood type specificity. A and B blood types have two different oligosaccharide glycolipids embedded in the cell membranes of the red blood cells, AB-type blood has both, while O blood type has neither.

Mannan oligosaccharides (MOS) are widely used in animal feed to improve gastrointestinal health, energy levels and performance. They are normally obtained from the yeast cell walls of Saccharomyces cerevisiae. Research at the University of Illinois has demonstrated that mannan oligosaccharides differ from other oligosaccharides in that they are not fermentable and their primary mode of actions include agglutination of type-1 fimbrae pathogens and immunomodulation ^[2]

Therapeutic effects

When oligosaccharides are consumed, the undigested portion serves as food for the intestinal microflora. Depending on the type of oligosaccharide, different bacterial groups are stimulated or suppressed.^[3]^[4]

Clinical studies have shown that administering FOS, GOS, or inulin can increase the number of these friendly bacteria in the colon while simultaneously reducing the population of harmful bacteria.^[5]

Role in human reproduction system

The Sialyl-Lewisx Oligosaccharide identified in a 2011 study, seems to be a the most abundant carbohydrate receptor present in the outer coating (zona pellucida (ZP)) of the human ova, and is implicated as a large factor of Sperm-ZP binding leading to fertilization. These sialyl-Lewisx branches are much more common on the ovum than on any other kind of body cell; they completely coat it. The discovery of the largest receptor on the human ovum may help improve infertility research. ^[6]^[7]

Role in mother-to-child transmission of HIV-1

Breast-feeding is the highest prevalence factor of postnatal transmission of HIV-1. However, most breast-fed infants do not contract the virus from the infected mother despite the continuous exposure. The Lewis antigen glycans in human milk compete with HIV-1 glycoprotein-120 and binds to the dendritic cell-specific ICAM3-grabbing non-integrin (DC-SIGN) on human dendritic cells. The glycans inhibit the transfer of the virus to the CD4 T lymphocytes. Because the human milk oligosaccharides carry one more of the Lewis antigen glycan, it's hypothesized that they do compete with gp120 for binding. ^[8]

Sources

FOS and inulin are found naturally in Jerusalem artichoke, burdock, chicory, leeks, onions, and asparagus. FOS products derived from chicory root contain significant quantities of inulin, a fiber widely distributed in fruits, vegetables and plants. Inulin is a significant part of the daily diet of most of the world’s population. FOS can also be synthesized by enzymes of the fungus Aspergillus niger acting on sucrose. GOS is naturally found in soybeans and can be synthesized from lactose (milk sugar). FOS, GOS, and inulin are available as nutritional supplements in capsules, tablets, and as a powder.

Not all natural oligosaccharides occur as components of glycoproteins or glycolipids. Some, such as the raffinose series, occur as storage or transport carbohydrates in plants. Others, such as maltodextrins or cellodextrins, result from the microbial breakdown of larger polysaccharides such as starch or cellulose.

Carrots are an excellent source of oligosaccharides but only after they have been cooked for an hour. This cooking breaks down the starches into the shorter chains needed for bioavailability. (Moro soup, invented by Ernst Moro in Germany in 1908 has been used for decades to treat bacterial infections in humans and farm animals. This soup not only prevents the bacteria from attaching to the intestinal wall, but also prevents bacteria from reproducing, according to DW TV.)

References

^ Oligosaccharides at the US National Library of Medicine Medical Subject Headings (MeSH)
^ M R Smiricky-Tjardes, E A Flickinger, C M Grieshop, L L Bauer, M R Murphy, G C Fahey (October 2003). "In vitro fermentation characteristics of selected oligosaccharides by swine fecal microflora" (Abstract (free)). 81 (10). pp. 2505–2514. Retrieved 30 March 2013.
^ Bode, L. (2009). "Human milk oligosaccharides: prebiotics and beyond.". Nutrition Reviews 67 (2): S183–91. doi:10.1111/j.1753-4887.2009.00239.x.
^ De Filippo, C., Cavalieri, D., Di Paola, M., Ramazzotti, M., Poullet, J. B., Massart, S., et al. (2010). "Impact of diet in shaping gut microbiota revealed by a comparative study in children from Europe and rural Africa.". Proceedings of the National Academy of Sciences 107 (33): 14691–14696. doi:10.1073/pnas.1005963107.
^ Macfarlane GT, Steed H. and Macfarlane S. (2008). "Bacterial metabolism and health-related effects of galacto-oligosaccharides and other prebiotics". J. Appl. Microbiol. 104 (2): 305–344. doi:10.1111/j.1365-2672.2007.03520.x. PMID 18215222.
^ http://news.sciencemag.org/sciencenow/2011/08/the-sweet-meeting-of-sperm-and-e.html
^ http://www.sciencemag.org/content/333/6050/1761
^ Hong, Ninonuevo, Lee, Bode, Librill, "Human milk oligosaccharides reduce HIV-1-gp120 binding to dendritic cell-specific ICAM3-grabbing non-integrin (DC-SIGN)", "pubmed.gov."

UpToDate Contents

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1. アレルギー性疾患の予防のためのプレバイオティクスおよびプロバイオティクス prebiotics and probiotics for prevention of allergic disease
2. 正期産児のための母乳の栄養組成 nutritional composition of human milk for full term infants
3. ヒト絨毛性性ゴナドトロピン：妊娠および妊娠性絨毛性疾患の検査と低検査値が持続する原因 human chorionic gonadotropin testing in pregnancy and gestational trophoblastic disease and causes of low persistent levels
4. 腸内ガスと膨満 intestinal gas and bloating
5. 先天性代謝異常：分類 inborn errors of metabolism classification

English Journal

Oligosaccharide biosensor for direct monitoring of enzymatic activities using QCM-D.

Bouchet-Spinelli A, Reuillard B, Coche-Guérente L, Armand S, Labbé P, Fort S.SourceCentre de Recherches sur les Macromolécules Végétales (CERMAV-CNRS), affiliated with Université de Grenoble, Member of the Institut de Chimie Moléculaire de Grenoble (ICMG) and Member of the PolyNat Carnot Institute, BP 53, 38041 Grenoble cedex 9, France. Electronic address: aurelie.bouchet-spinelli@ujf-grenoble.fr.
Biosensors & bioelectronics.Biosens Bioelectron.2013 Nov 15;49:290-6. doi: 10.1016/j.bios.2013.05.027. Epub 2013 May 30.
Enzymatic modification of saccharidic biomass is a subject of intensive research with potential applications in plant or human health, design of biomaterials and biofuel production. Bioengineering and metagenomics provide access to libraries of glycoside hydrolases but the biochemical characterizati
PMID 23774166

Identification and characterisation of water and alkali soluble oligosaccharides from hazelnut skin (Corylus avellana L.).

Montella R, Coïsson JD, Travaglia F, Locatelli M, Bordiga M, Meyrand M, Barile D, Arlorio M.SourceDipartimento di Scienze del Farmaco & Drug and Food Biotechnology Center, Università degli Studi del Piemonte Orientale "A. Avogadro", Largo Donegani 2, 28100 Novara, Italy.
Food chemistry.Food Chem.2013 Oct 15;140(4):717-25. doi: 10.1016/j.foodchem.2013.01.061. Epub 2013 Feb 1.
Hazelnut skins are a good example of agricultural by-product with the potential to become a valuable source of functional ingredients. In this work, the fibre from hazelnut skins was extracted by using water and alkali solution and characterised by a suite of analytical tools (MALDI-FTICR, nano LC-C
PMID 23692758

Difucosylation of chitooligosaccharides by eukaryote and prokaryote α1,6-fucosyltransferases.

Ihara H, Hanashima S, Tsukamoto H, Yamaguchi Y, Taniguchi N, Ikeda Y.SourceDivision of Molecular Cell Biology, Department of Biomolecular Sciences, Saga University Faculty of Medicine, 5-1-1 Nabeshima, Saga 849-8501, Japan.
Biochimica et biophysica acta.Biochim Biophys Acta.2013 Oct;1830(10):4482-90. doi: 10.1016/j.bbagen.2013.05.013. Epub 2013 May 18.
BACKGROUND: The synthesis of eukaryotic N-glycans and the rhizobia Nod factor both involve α1,6-fucosylation. These fucosylations are catalyzed by eukaryotic α1,6-fucosyltransferase, FUT8, and rhizobial enzyme, NodZ. The two enzymes have similar enzymatic properties and structures but display diff
PMID 23688399

Japanese Journal

Characterization of an α-glucosidase, HdAgl, from the digestive fluid of Haliotis discus hannai

Satoh Takuya,Inoue Akira,Ojima Takao
Comparative biochemistry and physiology b : biochemistry & molecular biology 166(1), 15-22, 2013-09-00
… This enzyme could degrade various sizes of maltooligosaccharides into glucose and released glucose from starch producing no appreciable intermediate oligosaccharides. …
NAID 120005342539

Kinetics of lactose conversion to galacto-oligosaccharides by β-galactosidase immobilized on PVDF membrane(BIOCHEMICAL ENGINEERING)

Palai Tapas,Bhattacharya Prashant K.
Journal of bioscience and bioengineering 115(6), 668-673, 2013-06-00
… Experimental studies were made for immobilization of enzymes on microporous polyvinylidene fluoride (PVDF) membrane in order to carry out enzymatic reaction of lactose into galacto-oligosaccharides using β-galactosidase. … The present work, however, is the first part in the direction of enzymatic membrane reactor studies for carrying out reaction followed by membrane based separation to purify galacto-oligosaccharides out of reaction mixture. …
NAID 110009614952

Mass preparation of oligosaccharides by the hydrolysis of chondroitin sulfate polysaccharides with a subcritical water microreaction system

Yamada Shuhei,Matsushima Keiichiro,Ura Haruo,Miyamoto Nobuyuki,Sugahara Kazuyuki
Carbohydrate Research 371, 16-21, 2013-04-19
… Thus, CS oligosaccharides are expected to have pharmacological applications. … Since the activity of orally administered CS is expected to increase by depolymerization, industrial production of CS oligosaccharides is required. … CS oligosaccharides principally containing an N-acetyl-D-galactosamine residue at their reducing ends were successfully obtained. … No significant desulfation was found in CS oligosaccharides prepared under optimized conditions. …
NAID 120005228742