Isomaltooligosaccharide
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Isomaltooligosaccharide (IMO) is a mixture of short-chain
carbohydrate 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 (as in water) and thus with the empirical formula (where ''m'' may o ...
s 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 Starch or amylum is a polymeric carbohydrate consisting of numerous glucose units joined by glycosidic bonds. This polysaccharide is produced by most green plants for energy storage. Worldwide, it is the most common carbohydrate in human die ...
, which is enzymatically converted into a mixture of isomaltooligosaccharides.


Chemistry

The term "
oligosaccharide An oligosaccharide (/ˌɑlɪgoʊˈsækəˌɹaɪd/; from the Greek ὀλίγος ''olígos'', "a few", and σάκχαρ ''sácchar'', "sugar") is a saccharide polymer containing a small number (typically two to ten) of monosaccharides (simple sug ...
" encompasses carbohydrates that are larger than simple di- or tri-
saccharides 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 (as in water) and thus with the empirical formula (where ''m'' may or may ...
, but smaller than
polysaccharides 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 w ...
(greater than 10 units). Isomalto-oligosaccharides (IMO) are
glucose Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, u ...
oligomers with α-D-(1,6)-linkages, including isomaltose, panose, isomaltotriose, isomaltotetraose, isomaltopentaose, nigerose, kojibiose, and higher branched oligosaccharides. Depending on production method, the structure of the IMO molecules can vary significantly. While human intestinal enzymes readily digest α(1,4)-
glycosidic bonds A glycosidic bond or glycosidic linkage is a type of covalent bond that joins a carbohydrate (sugar) molecule to another group, which may or may not be another carbohydrate. A glycosidic bond is formed between the hemiacetal or hemiketal gr ...
, 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. 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 . 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 Starch or amylum is a polymeric carbohydrate consisting of numerous glucose units joined by glycosidic bonds. This polysaccharide is produced by most green plants for energy storage. Worldwide, it is the most common carbohydrate in human die ...
processed from
cereal A cereal is any grass cultivated for the edible components of its grain (botanically, a type of fruit called a caryopsis), composed of the endosperm, germ, and bran. Cereal grain crops are grown in greater quantities and provide more food ...
crops like wheat, barley,
pulses In medicine, a pulse represents the tactile arterial palpation of the cardiac cycle (heartbeat) by trained fingertips. The pulse may be palpated in any place that allows an artery to be compressed near the surface of the body, such as at the nec ...
(peas, beans,
lentils The lentil (''Lens culinaris'' or ''Lens esculenta'') is an edible legume. It is an annual plant known for its lens-shaped seeds. It is about tall, and the seeds grow in pods, usually with two seeds in each. As a food crop, the largest produ ...
), oats,
tapioca Tapioca (; ) is a starch extracted from the storage roots of the cassava plant (''Manihot esculenta,'' also known as manioc), a species native to the North and Northeast regions of Brazil, but whose use is now spread throughout South America ...
, 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 Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysi ...
, into high
maltose } Maltose ( or ), 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 tw ...
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 Maltotriose is a trisaccharide (three-part sugar) consisting of three glucose molecules linked with α-1,4 glycosidic bonds. It is most commonly produced by the digestive enzyme alpha-amylase (a common enzyme in human saliva) on amylose in starc ...
, 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.Kaneko, T.; Kohmoto, T.; Fukui, F.; Akiba, T.; Suzuki, S.; Hirao, A.; Nakatsuru, S.; Kanisawa, M. 1990. cute 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 apanese with English summary/ref> 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". Oligosaccharides that are not digested and absorbed in the small intestine, pass through to the colon where they are fermented by
Bifidobacteria ''Bifidobacterium'' is a genus of gram-positive, nonmotile, often branched anaerobic bacteria. They are ubiquitous inhabitants of the gastrointestinal tract though strains have been isolated from the vagina and mouth ('' B. dentium'') of ma ...
, thus enhancing the proliferation of the bacteria. In this respect, fermentable oligosaccharides may be considered
prebiotics 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 ...
. The oligosaccharides in IMO mixtures are, at least partially, fermented by bacteria in the colon and may, therefore, stimulate the growth of bacterial subpopulations.Qing, G.; Yi, Y.; Guohong, J.; Gai, C. 2003. tudy on the regulative effect of Isomaltooligosaccharides on human intestinal flora Wei Sheng Yan Jiu 32(1):54-55 hinese with English summary/ref>Kaneko, T.; Komoto, T.; Kikuchi, H.; Shiota, M.; Yatake, T.; lino, H.; Tsuji, K. 1993. ffects of isomaltooligosaccharides intake on defecation and intestinal environment in healthy volunteers Ninon Kasei Gakkaishi 44(4):245-254 apanese with English summary/ref>
Dental caries Tooth decay, also known as cavities or caries, is the breakdown of teeth due to acids produced by bacteria. The cavities may be a number of different colors from yellow to black. Symptoms may include pain and difficulty with eating. Complicat ...
is caused by the formation of insoluble
glucan A glucan is a polysaccharide derived from D-glucose, linked by glycosidic bonds. Glucans are noted in two forms: alpha glucans and beta glucans. Many beta-glucans are medically important. They represent a drug target for antifungal medications o ...
(
plaque Plaque may refer to: Commemorations or awards * Commemorative plaque, a plate or tablet fixed to a wall to mark an event, person, etc. * Memorial Plaque (medallion), issued to next-of-kin of dead British military personnel after World War I * Pl ...
) 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. The reported
Glycemic Index The glycemic (glycaemic) index (GI; ) is a number from 0 to 100 assigned to a food, with pure glucose arbitrarily given the value of 100, which represents the relative rise in the blood glucose level two hours after consuming that food. The GI of ...
(GI) for IMO is 34.66±7.65 (on a scale of 1–100) which represents a low GI. Consumption of IMO effectively improved bowel movements, stool output and microbial fermentation in the colon without any adverse effects in elderly people. Health claims for the various classes of oligosaccharides have been investigated by the
European Food Safety Authority The European Food Safety Authority (EFSA) is the agency of the European Union (EU) that provides independent scientific advice and communicates on existing and emerging risks associated with the food chain. EFSA was established in February 2002, ...
(EFSA) and found to be insufficiently substantiated. Therefore, health claims for oligosaccharides and prebiotics are prohibited in the
European Union The European Union (EU) is a supranational union, supranational political union, political and economic union of Member state of the European Union, member states that are located primarily in Europe, Europe. The union has a total area of ...
.


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.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 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. However, the U.S.
Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...
(FDA) has recommended a maximum consumption of 30 g/day for IMO. Higher dosages (greater than 40 g/day), can cause gastrointestinal symptoms like flatulence,
bloating Abdominal bloating (or simply bloating) is a short-term disease that affects the gastrointestinal tract. Bloating is generally characterized by an excess buildup of gas, air or fluids in the stomach. A person may have feelings of tightness, pres ...
, soft stool or
diarrhea Diarrhea, also spelled diarrhoea, is the condition of having at least three loose, liquid, or watery bowel movements each day. It often lasts for a few days and can result in dehydration due to fluid loss. Signs of dehydration often begin w ...
.


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. 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 BioNeutra North America, Inc. is a Canada-based agri-biotechnology manufacturer of patented technology to produce the food ingredients and natural fibre sweeteners, Isomaltooligosaccharide (IMO) and Fructooligosaccharide (FOS). BioNeutra is the ...
, received FDA- GRAS and
Health Canada Health Canada (HC; french: Santé Canada, SC)Health Canada is the applied title under the Federal Identity Program; the legal title is Department of Health (). is the department of the Government of Canada responsible for national health poli ...
approval for IMO. The
European Food Safety Agency The European Food Safety Authority (EFSA) is the agency of the European Union (EU) that provides independent scientific advice and communicates on existing and emerging risks associated with the food chain. EFSA was established in February 2002, ...
(EFSA) recently authorized xylo‐oligosaccharides (XOS) as a novel food (NF) pursuant to Regulation (EU) 2015/2283.


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 is a Japanese food company. It was renamed into the , on March 31, 2011. It was a major dairy industry company established in 1917. Apart from dairy products like milk, ice cream, and cheese, their lineup includes sports drinks, pizza, choco ...
(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, which was approved for use in Canada by Health Canada in 2012. US-based companies have also been producing other kinds of oligosaccharides, like GOS, FOS, and XOS.


See also

* (FOS) * (GOS) * (XOS)


References

{{carbohydrates Dietary supplements Food additives Oligosaccharides Prebiotics (nutrition) Sugar substitutes