Isomaltooligosaccharide

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Isomaltooligosaccharide (IMO) is a mixture of short-chain carbohydrates which has a digestion-resistant property. IMO is found naturally in some foods, as well as being manufactured commercially. The raw material used for manufacturing IMO is starch, which is enzymatically converted into a mixture of isomaltooligosaccharides.

Contents

Chemistry

The term "oligosaccharide" encompasses carbohydrates that are larger than simple di- or tri-saccharides, but smaller than polysaccharides (greater than 10 units). Isomalto-oligosaccharides (IMO) are glucose oligomers with α-D-(1,6)-linkages, including isomaltose, panose, isomaltotriose, isomaltotetraose, isomaltopentaose, nigerose, kojibiose, and higher branched oligosaccharides. [1] Depending on production method, the structure of the IMO molecules can vary significantly. While human intestinal enzymes readily digest α(1,4)-glycosidic bonds, longer change IMO (e.g. >= DP4) with α(1,6)-linkages are not easily hydrolyzed and exhibit a digestion-resistant property. Therefore, some IMO preparations are only partially digested in the upper gastrointestinal tract.

Isomalto-oligosaccharides are a normal part of the human diet and occur naturally in fermented foods, such as fermented sourdough breads and kimchi. The disaccharide isomaltose is also present in rice miso, soy sauce, and sake. [2] [3] [4] Isomaltose, one of the α(1,6)-linked disaccharide components of IMO, has been identified as a natural constituent of honey and although chemically related, it is not an IMO . [5] IMO is a sweet-tasting, high-density syrup which could be spray-dried into powder form.

Manufacturing

For manufacturing IMO on a commercial scale, food industries use starch processed from cereal crops like wheat, barley, pulses (peas, beans, lentils), oats, tapioca, rice, potato and others. This variety in sources could benefit consumers who have allergies or hypersensitivity to certain cereal crops. The manufacturing process controls the degree of polymerization (dp) and the α(1,6)-linkages to ensure a consistent quality of IMO from different starch sources. The starch is first converted, by means of simple enzymatic hydrolysis, into high maltose syrup with di-, tri and oligosaccharides (2, 3 or more glucose units) having α(1,4)-glycosidic linkages which are readily digestible in the human intestine. These α(1,4)-glycosidic linkages are further converted into digestion-resistant α(1,6)-glycosidic linkages, creating "iso" linkages between glucose moieties and forming Isomalto-oligosaccharide (IMO).

The majority of oligosaccharides found in IMO consist of three to six monosaccharide (glucose) units linked together. However, disaccharides, as well as longer polysaccharides (up to nine glucose units), are also present. The disaccharide fraction of IMO consists mainly of α(1,6)-linked isomaltose, while maltotriose, panose, and isomaltotriose make up the trisaccharide fraction. A mixture of isomaltotetraose, isomaltopentaose, maltohexaose, maltoheptaose, and small amounts of oligomers with 8 or more degrees of polymerization, comprise the remaining oligomers in IMO. Longer oligomers do not have 100% α(1,6)-linkages; the ratio of α(1,4)- to α(1,6)-linkages is variable.

Health claims

Animal studies describe IMO as a multifunctional molecule which exerts positive effects on digestive health; it acts as a prebiotic, decreases flatulence, has a low glycemic index, and prevents dental caries in animals. [6] [7] [8] [9] [10]

Prebiotics are defined as "non-digestible food ingredients that may beneficially affect the host by selectively stimulating the growth and/or activity of a limited number of bacteria in the colon". [11] Oligosaccharides that are not digested and absorbed in the small intestine, pass through to the colon where they are fermented by Bifidobacteria, thus enhancing the proliferation of the bacteria. In this respect, fermentable oligosaccharides may be considered prebiotics. The oligosaccharides in IMO mixtures are, at least partially, fermented by bacteria in the colon and may, therefore, stimulate the growth of bacterial subpopulations. [12] [13] [14] [15] [16]

Dental caries is caused by the formation of insoluble glucan (plaque) on the surface of teeth, and the production of acids by bacteria in the plaque. These acids attack the hard tissues of the teeth. Studies with animal models showed that IMO, in place of sucrose, reduces the amount of plaque formed and also reduces the amount of enamel-attacking acids formed. Therefore, IMO acts as an anti-caries agent. [17]

The reported Glycemic Index (GI) for IMO is 34.66±7.65 (on a scale of 1–100) which represents a low GI. [18] Consumption of IMO effectively improved bowel movements, stool output and microbial fermentation in the colon without any adverse effects in elderly people. [19]

Health claims for the various classes of oligosaccharides have been investigated by the European Food Safety Authority (EFSA) and found to be insufficiently substantiated. Therefore, health claims for oligosaccharides and prebiotics are prohibited in the European Union. [20]

Usage

IMO is finding global acceptance by food manufacturers for use in a wide range of food products, especially beverages and snack/nutrition bars. In the United States, IMO is used mostly as a source of dietary fiber. However, IMO is also used as a low calorie sweetener in a variety of foods like bakery and cereal products. Since IMO is about 50% as sweet as sucrose (sugar), it cannot replace sugar in a one-to-one ratio. However, IMO has few side effects compared to other oligosaccharides of the same class. [21] Therefore this carbohydrate molecule is receiving growing attention by food manufacturers across North America, as well as in Europe.

Side-effects

Generally, all digestion-resistant oligosaccharides, including IMO, have adverse side effects when consumed in amounts greater than permissible levels. The maximum permissible dose of IMO is 1.5 g/kg body weight, which is higher than for any other sugar substitute. [21] However, the U.S. Food and Drug Administration (FDA) has recommended a maximum consumption of 30 g/day for IMO. [22] Higher dosages (greater than 40 g/day), can cause gastrointestinal symptoms like flatulence, bloating, soft stool or diarrhea.

Regulatory information

IMO and other oligosaccharides have long been approved in China and Japan. In Japan, IMO has been on the list of Foods for Specified Health Use (FOSHU) for more than 10 years. In 2002, over 50% of the FOSHU foods in Japan incorporated oligosaccharides as the functional component. [23] [24] The list includes many types of foods: soft drinks and other beverages, frozen yogurt, confectionery products, sweeteners, cookies, coffee drink mixes, bread, tofu, chocolate, and soup mixes. IMO has been imported into the United States for the last few years but has never been manufactured there or formally approved by the FDA. In 2009, a Canadian-based company, BioNeutra, received FDA-GRAS and Health Canada approval for IMO. [25] The European Food Safety Agency (EFSA) recently authorized xylo‐oligosaccharides (XOS) as a novel food (NF) pursuant to Regulation (EU) 2015/2283. [26]

Commercial availability

IMO is commercially manufactured mostly in China and Japan. However, most of this product is consumed locally or exported to neighboring Asian countries. In Japan, Meiji Dairies (Meiji Food Company) is one of the biggest IMO producers. IMO is marketed under several trade names like IMO-900 and IMO-800. Being a novel food ingredient, there wasn't a producer of IMO in North America and Europe until BioNeutra North America, Inc. began to manufacture this product with the VitaFiber IMO trademark, [27] which was approved for use in Canada by Health Canada in 2012. [28] US-based companies have also been producing other kinds of oligosaccharides, like GOS, FOS, and XOS.

See also

Related Research Articles

<span class="mw-page-title-main">Carbohydrate</span> Organic compound that consists only of carbon, hydrogen, and oxygen

In organic chemistry, a carbohydrate is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen–oxygen atom ratio of 2:1 and thus with the empirical formula Cm(H2O)n. However, not all carbohydrates conform to this precise stoichiometric definition, nor are all chemicals that do conform to this definition automatically classified as carbohydrates.

<span class="mw-page-title-main">Disaccharide</span> Complex sugar

A disaccharide is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disaccharides are simple sugars soluble in water. Three common examples are sucrose, lactose, and maltose.

<span class="mw-page-title-main">Polysaccharide</span> Long carbohydrate polymers comprising starch, glycogen, cellulose, and chitin

Polysaccharides, or polycarbohydrates, are the most abundant carbohydrates found in food. They are long chain polymeric carbohydrates composed of monosaccharide units bound together by glycosidic linkages. This carbohydrate can react with water (hydrolysis) using amylase enzymes as catalyst, which produces constituent sugars. They range in structure from linear to highly branched. Examples include storage polysaccharides such as starch, glycogen and galactogen and structural polysaccharides such as cellulose and chitin.

<span class="mw-page-title-main">Fructose</span> Simple ketonic monosaccharide found in many plants

Fructose, or fruit sugar, is a ketonic simple sugar found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. It is one of the three dietary monosaccharides, along with glucose and galactose, that are absorbed by the gut directly into the blood of the portal vein during digestion. The liver then converts both fructose and galactose into glucose, so that dissolved glucose, known as blood sugar, is the only monosaccharide present in circulating blood.

<span class="mw-page-title-main">Maltose</span> Chemical compound

Maltose, also known as maltobiose or malt sugar, is a disaccharide formed from two units of glucose joined with an α(1→4) bond. In the isomer isomaltose, the two glucose molecules are joined with an α(1→6) bond. Maltose is the two-unit member of the amylose homologous series, the key structural motif of starch. When alpha-amylase breaks down starch, it removes two glucose units at a time, producing maltose. An example of this reaction is found in germinating seeds, which is why it was named after malt. Unlike sucrose, it is a reducing sugar.

<span class="mw-page-title-main">Maltase</span> Enzyme

Maltase is one type of alpha-glucosidase enzymes located in the brush border of the small intestine. This enzyme catalyzes the hydrolysis of disaccharide maltose into two simple sugars of glucose. Maltase is found in plants, bacteria, yeast, humans, and other vertebrates. It is thought to be synthesized by cells of the mucous membrane lining the intestinal wall.

<span class="mw-page-title-main">Inulin</span> Chemical compound

Inulins are a group of naturally occurring polysaccharides produced by many types of plants, industrially most often extracted from chicory. The inulins belong to a class of dietary fibers known as fructans. Inulin is used by some plants as a means of storing energy and is typically found in roots or rhizomes. Most plants that synthesize and store inulin do not store other forms of carbohydrate such as starch. In the United States in 2018, the Food and Drug Administration approved inulin as a dietary fiber ingredient used to improve the nutritional value of manufactured food products. Using inulin to measure kidney function is the "gold standard" for comparison with other means of estimating glomerular filtration rate.

<span class="mw-page-title-main">Reducing sugar</span> Sugars that contain free OH group at the anomeric carbon atom

A reducing sugar is any sugar that is capable of acting as a reducing agent. In an alkaline solution, a reducing sugar forms some aldehyde or ketone, which allows it to act as a reducing agent, for example in Benedict's reagent. In such a reaction, the sugar becomes a carboxylic acid.

Fructooligosaccharides (FOS) also sometimes called oligofructose or oligofructan, are oligosaccharide fructans, used as an alternative sweetener. FOS exhibits sweetness levels between 30 and 50 percent of sugar in commercially prepared syrups. It occurs naturally, and its commercial use emerged in the 1980s in response to consumer demand for healthier and calorie-reduced foods.

Prebiotics are compounds in food that induce the growth or activity of beneficial microorganisms such as bacteria and fungi. The most common example is in the gastrointestinal tract, where prebiotics can alter the composition of organisms in the gut microbiome.

Glucomannan is a water-soluble polysaccharide that is considered a dietary fiber. It is a hemicellulose component in the cell walls of some plant species. Glucomannan is a food additive used as an emulsifier and thickener. It is a major source of mannan oligosaccharide (MOS) found in nature, the other being galactomannan, which is insoluble.

Polydextrose is a synthetic polymer of glucose. It is a food ingredient classified as soluble fiber by the US FDA as well as Health Canada, as of April 2013. It is frequently used to increase the dietary fiber content of food, to replace sugar, and to reduce calories and fat content. It is a multi-purpose food ingredient synthesized from dextrose (glucose), plus about 10 percent sorbitol and 1 percent citric acid. Its E number is E1200. The FDA approved it in 1981.

<span class="mw-page-title-main">Fructan</span>

A fructan is a polymer of fructose molecules. Fructans with a short chain length are known as fructooligosaccharides. Fructans can be found in over 12% of the angiosperms including both monocots and dicots such as agave, artichokes, asparagus, leeks, garlic, onions, yacón, jícama, barley and wheat.

<span class="mw-page-title-main">Isomaltulose</span> Chemical compound

Isomaltulose is a disaccharide carbohydrate composed of glucose and fructose. The glucose and fructose are linked by an alpha-1,6-glycosidic bond. Isomaltulose is present in honey and sugarcane extracts. It tastes similar to sucrose with half the sweetness. Isomaltulose, also known by the trade name Palatinose, is manufactured by enzymatic rearrangement (isomerization) of sucrose from beet sugar. The enzyme and its source were discovered in Germany in 1950, and since then its physiological role and physical properties have been studied extensively. Isomaltulose has been used as an alternative to sugar in foods in Japan since 1985, in the EU since 2005, in the US since 2006, and in Australia and New Zealand since 2007, besides other countries worldwide. Analytical methods for characterization and assay of commercial isomaltulose are laid down, for example, in the Food Chemicals Codex. Its physical properties closely resemble those of sucrose, making it easy to use in existing recipes and processes.

<span class="mw-page-title-main">Isomaltose</span> Chemical compound

Isomaltose is a disaccharide similar to maltose, but with a α-(1-6)-linkage instead of the α-(1-4)-linkage. Both of the sugars are dimers of glucose, which is a pyranose sugar. Isomaltose is a reducing sugar. Isomaltose is produced when high maltose syrup is treated with the enzyme transglucosidase (TG) and is one of the major components in the mixture isomaltooligosaccharide.

<span class="mw-page-title-main">Galactooligosaccharide</span> Class of prebiotics

Galactooligosaccharides (GOS), also known as oligogalactosyllactose, oligogalactose, oligolactose or transgalactooligosaccharides (TOS), belong to the group of prebiotics. Prebiotics are defined as non-digestible food ingredients that beneficially affect the host by stimulating the growth and/or activity of beneficial bacteria in the colon. GOS occurs in commercially available products such as food for both infants and adults.

<span class="mw-page-title-main">Xylooligosaccharide</span> Polymer of the sugar xylose

Xylooligosaccharides (XOS) are polymers of the sugar xylose. They are produced from the xylan fraction in plant fiber. Their C5 structure is fundamentally different from other prebiotics, which are based upon C6 sugars. Xylooligosaccharides have been commercially available since the 1980s, originally produced by Suntory in Japan. They have more recently become more widely available commercially, as technologies have advanced and production costs have fallen. Some enzymes from yeast can exclusively convert xylan into only xylooligosaccharides-DP-3 to 7.

<span class="mw-page-title-main">Neopullulanase</span>

Neopullulanase is an enzyme of the alpha-amylase family with systematic name pullulan 4-D-glucanohydrolase (panose-forming). This enzyme principally catalyses the following chemical reaction by cleaving pullulan's alpha-1,4-glucosidic bonds:

Lacto-<i>N</i>-tetraose Chemical compound

Lacto-N-tetraose is a complex sugar found in human milk. It is one of the few characterized human milk oligosaccharides (HMOs) and is enzymatically synthesized from the substrate lactose. It is biologically relevant in the early development of the infant gut flora.

<span class="mw-page-title-main">Kestose</span> Sugar from fructooligosaccharide group

Kestose is a class of sugars that belongs to a group of fructooligosaccharides.

References

  1. ↑ PDRNS. 2001. Prebiotics. in: PDR for Nutritional Supplements (1st Ed.). Physicians' Desk Reference (PDR); Demoines, Iowa/Medical Economics Data Production Company; Montvale, New Jersey, pp. 372-375
  2. ↑ Hondo, S. & Mochizuki, T., Free Sugars in Miso. Nipon Shokuhin Kogyo Gakkaishi 26(11), (1979) 469-472
  3. ↑ Nishino, R.; Ozawa, Y.; Yasuda, A.; Sakasai, T. 1981. [Oligosaccharides in soy sauce]. Denpun Kagaku 28(2):125-131 [Japanese with English summary]
  4. ↑ Tungland, B.C.; Meyer, D. 2002. Nondigestible oligo-and polysaccharides (dietary fiber): Their physiology and role in human health and food. Compr Rev Food Sci Food Safety 3:73-92
  5. ↑ White, J.W.; Hoban, N. 1959. Composition of honey. IV. Identification of the disaccharides. Arch Biochem Biophys 80(2):386-392
  6. ↑ Kaneko, T.; Kohmoto, T.; Fukui, F.; Akiba, T.; Suzuki, S.; Hirao, A.; Nakatsuru, S.; Kanisawa, M. 1990. [Acute and chronic toxicity and mutagenicity studies on isomaltooligosaccharides, and the effect on peripheral blood lymphocytes and intestinal microflora]. Shokuhin Eiseigaku Zasshi 31 (5):394-403 [Japanese with English summary]
  7. ↑ Rycroft, C.E.; Jones, M.R.; Gibson, G.R.; Rastall, R.A. 2001. A comparative in vitro evaluation of the fermentation properties of prebiotic oligosaccharides. J Appl Microbiol 91(5):878-887
  8. ↑ Hesta, M., Debraekeleer, J., Janssens, G. P. J. & De Wilde, R. (2001) [The effect of a commercial high-fibre diet and an Isomalto-oligosaccharide-supplemented diet on post-prandial glucose concentrations in dogs] J. Animal Physio. Animal Nutr., 85(7-8) 217
  9. ↑ Hesta, M, Roosen, W, et al. (2003). Prebiotics affect nutrient digestibility but not fecal ammonia in dogs fed increased dietary protein levels. British Journal of Nutrition 90, 1007-1014
  10. ↑ Minami T, et al. (1989). Caries-inducing activity of isomaltooligosugar (IMOS) in vitro and rat experiments. Shoni Shikagaku Zasshi 27(4) 1010-7
  11. ↑ Roberfroid M., "Prebiotics: The Concept Revisited", J. Nutr. 137:830-837S, 2007
  12. ↑ Ketabi, A., Dieleman, A. L., and Ganzle, G. M., 2011, [influence of isomaltooligosaccharides on intestinal microbiota in rats], J. Appl. Micro. Biol., 110, 1297-1306
  13. ↑ Kohmoto, T.; Fukui, F.; Takaku, H.; Machida, Y.; Arai, M.; Mitsuoka, T. 1988. Effect of isomalto-oligosaccharides on human fecal flora. Bifidobacteria Microflora 7(2):61-69
  14. ↑ Qing, G.; Yi, Y.; Guohong, J.; Gai, C. 2003. [Study on the regulative effect of Isomaltooligosaccharides on human intestinal flora]. Wei Sheng Yan Jiu 32(1):54-55 [Chinese with English summary]
  15. ↑ Kaneko, T.; Komoto, T.; Kikuchi, H.; Shiota, M.; Yatake, T.; lino, H.; Tsuji, K. 1993. [Effects of isomaltooligosaccharides intake on defecation and intestinal environment in healthy volunteers]. Ninon Kasei Gakkaishi 44(4):245-254 [Japanese with English summary]
  16. ↑ Kaneko, T., Kohmoto, T., Kikuchi, H., Shito, M., Iino, H. and Mitsuoka, T. (1994) [Effect of isomaltooligosaccharides with different degrees of polymerization on human fecal bifidobacteria] Biosci. Biotech. Biochem. 58(12), 2288-2290
  17. ↑ Minami T, et al. (1989). Caries-inducing activity of isomaltooligosugar (IMOS) in vitro and rat experiments. Shoni Shikagaku Zasshi 27(4) 1010-7)
  18. ↑ Sheng, G. E., Dong-lian, C. A. I. & Wan, Li-li. (2006) [Determination of glycemic index of xylitol and isooligosccharide] Chin. J. Clin. Nutr., 14(4) 235-237
  19. ↑ Chen, H.-L., et al., 2001. Effects of isomalto-oligosaccharides on bowel functions and indicators of nutritional status in constipated elderly men. J Am Coll Nutr 20(1):44-49
  20. ↑ EU Register of nutrition and health claims made on foods, http://ec.europa.eu/nuhclaims/
  21. 1 2 Oku, T.; Nakamura, S., 2002. Digestion, absorption, fermentation, and metabolism of functional sugar substitutes and their available energy. Pure Appl. Chem. 74(7): 1253-1261
  22. ↑ "Archived copy" (PDF). Archived from the original (PDF) on 2012-04-26. Retrieved 2011-12-13.{{cite web}}: CS1 maint: archived copy as title (link)
  23. ↑ Nakakuki, T., (2003) Development of Functional Oligosaccharides in Japan. Trends in Glycoscience and Glycotechnology 15(82): 62 & 63
  24. ↑ Yamaguchi, P. & Associates, Inc. (2004) Functional Foods & FOSHU Japan, Market & Product Report
  25. ↑ "Agency Response Letter GRAS Notice No. GRN 000246". Food and Drug Administration . Archived from the original on 2012-03-21. Retrieved 2019-12-16.
  26. ↑ Turck, Dominique; Bresson, Jean-Louis; Burlingame, Barbara; Dean, Tara; Fairweather‐Tait, Susan; Heinonen, Marina; Hirsch‐Ernst, Karen Ildico; Mangelsdorf, Inge; McArdle, Harry J. (2018). "Safety of xylo-oligosaccharides (XOS) as a novel food pursuant to Regulation (EU) 2015/2283" (PDF). EFSA Journal. 16 (7): e05361. doi:10.2903/j.efsa.2018.5361. ISSN   1831-4732. PMC   7009669 . PMID   32625993.
  27. ↑ "BioNeutra: Producers of VitaFiber™IMO".
  28. ↑ "Novel Food Information - Isomalto-oligosaccharide (VitaFiber ™)". 18 February 2011.
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