Kestose

Last updated
1-Kestose
1-Kestose.PNG
Chemical structure of 1-kestose trisaccharide
Names
IUPAC name
(2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-2-[[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Other names
1-Kestose; O-beta-D-Fructofuranosyl-(2.1)-beta-D-fructofuranosyl-alpha-D-glucopyranoside
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 207-429-4
KEGG
PubChem CID
UNII
  • InChI=1S/C18H32O16/c19-1-6-9(23)12(26)13(27)16(31-6)34-18(15(29)11(25)8(3-21)33-18)5-30-17(4-22)14(28)10(24)7(2-20)32-17/h6-16,19-29H,1-5H2/t6-,7-,8-,9-,10-,11-,12+,13-,14+,15+,16-,17-,18+/m1/s1
    Key: VAWYEUIPHLMNNF-OESPXIITSA-N
  • C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO[C@]3([C@H]([C@@H]([C@H](O3)CO)O)O)CO)O)O)O)O
Properties
C18H32O16
Molar mass 504.438 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Kestose is a class of sugars that belongs to a group of fructooligosaccharides. [1]

Contents

Chemical properties

Kestoses are typical fructooligosaccharides, and in its structure, one fructose molecule is combined with sucrose to form a trisaccharide. In the 1-kestose type, the fructose molecule will be connected to sucrose by a (1→2β) glycosidic bond. Different types of kestoses have different lengths of subunits in the chain, for example, 6-kestose has from 10 to 200 fructose residues and is also called levan type fructooligosaccharide. Also, 1-kestose has less than 50 fructose residues in the chain and is also called inulin type fructooligosaccharide. [2] Kestoses are categorized based on their structure into 3 main groups: 1-kestose, 6-kestose, neokestose. The most common of them is 1-kestose which is found in many plants. [3]

Biosynthesis

According to the conditions of the plant cell, kestose biosynthesis occurs in the vacuole. The precursor molecule of kestose is sucrose. The sucrose-sucrose fructosyl transferase enzyme relates a sucrose molecule with a fructose residue to a second sucrose molecule, producing a kestose-1 molecule. Following, the enzyme fructan-fructan 1-fructosyl transferase combines fructose residue from trisaccharides, and by that synthetase longer kestose-1 chain. Respectively, to synthesize 6-kestose chain, the enzyme fructan-fructan 6-fructosyl transferase should combine fructose residue from trisaccharide and that synthesize a longer chain. [2]

Food sources

As well as other fructooligosaccharides, kestose can be found in such plants as wheat, onions, asparagus, and banana. Moreover, the plant families of Compositae, Amaryllidaceae, Gramineae and Liliaceae contain kestose along with other fructooligosaccharides in parts of the plant such as fruits, roots, and tubers. [4]

Kestose-1 composition in various vegetables [4]
Ingredientmg/g
Acorn Squash 0.2
Artichoke (globe)1.5
Carrot (Bunny Luv)0.3
Chicory root 1.7
Garlic 3.3
Leek 0.7
Lettuce 0.3
Shallot 4.5
Yam 0.2

Industrial production

In the industry, kestose, like other fructooligosaccharides, is produced by transfructosylation reaction of sucrose with the enzyme B-fructofuranosidase, which is obtained from the mold fungus Aspergillus niger . [4]

Potential health effects

Prebiotic activity

Kestose as well as many other fructooligosaccharides belong to the prebiotics, i.e. to the substances that have a positive effect on the intestinal microbiome after consuming them in food. In particular, the consumption of kestose mixed with other fructooligosaccharides increases the concentration of healthy probiotic bifidobacteria and decreases the concentration of the Clostridia, bacteria associated with inflammatory processes. [5]

Consequently, kestoses complies with the essential criteria required for a prebiotic: 1) they are not digested by enzymes of the mammalian host organism, 2) they have a positive effect on only positive probiotic microorganisms growth, 3) they have a positive effect on the microbiome in general, 4) they have a positive effect on the defense system of host organism. [6]

Consumption with food

Kestose has less caloric value than sucrose, and is not a promoter of tooth decay. Consumption of kestose, as well as other prebiotics, reduces the risk of cancer, hyperlipidaemia and acute gastroenteritis. [6]

In particular, kestoses perform their prebiotic function by positively influencing the growth of lactobacilli and bifidobacteria probiotics, which protect the host organism from acute gastroenteritis, which appears when pathogenic microorganisms multiply in the intestines and has symptoms such as diarrhea, vomiting, and pain in the abdomen. [6]

Impact of kestose-1 on glucose metabolism in rats with type 2 diabetes

Studies on rats have shown that the consumption of kestose-1 helps the propagation of probiotics such as Anaerostipes caccae in the intestinal microflora. These probiotics are butyrate producer bacteria, which through the production of butyrate contribute to glucose tolerance and weight loss in rodents. Also, the consumption of kestose-1 by rats promotes the multiplication of probiotics of the bifidobacteria class, which produce the metabolites acetate and lactate, which in turn Anaerostipes caccae also uses to synthesize butyrate. [7]

Impact of kestose-1 on symptoms of the atopic dermatitis disease

Studies show the positive effect of consumption of prebiotic kestose-1 on the reproduction of microorganisms Faecalibacterium prausnitzii , which have an anti-inflammatory effect due to the production of short-chain fatty acid - butyrate. Butyrate in turn promotes the differentiation of regulatory T cells, which have the function of suppressing the production of T helper 2 cytokines that cause inflammatory processes in allergic reactions such as atopic dermatitis disease. Significant results were achieved with the consumption of kestose-1 for multiplication of Faecalibacterium prausnitzii probiotic, and in the consequence of relief of symptoms of atopic dermatitis disease in children aged 2 to 5 years, after 6 weeks of consumption of kestose-1 in food.[8] [8]

Related Research Articles

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

Butyric acid, also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula CH3CH2CH2CO2H. It is an oily, colorless liquid with an unpleasant odor. Isobutyric acid is an isomer. Salts and esters of butyric acid are known as butyrates or butanoates. The acid does not occur widely in nature, but its esters are widespread. It is a common industrial chemical and an important component in the mammalian gut.

<span class="mw-page-title-main">Inulin</span> Natural plant polysaccharides

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.

An oligosaccharide is a saccharide polymer containing a small number of monosaccharides. Oligosaccharides can have many functions including cell recognition and cell adhesion.

<span class="mw-page-title-main">Fructose malabsorption</span> Medical condition

Fructose malabsorption, formerly named dietary fructose intolerance (DFI), is a digestive disorder in which absorption of fructose is impaired by deficient fructose carriers in the small intestine's enterocytes. This results in an increased concentration of fructose. Intolerance to fructose was first identified and reported in 1956.

<span class="mw-page-title-main">Fructooligosaccharide</span> Oligosaccharide fructans

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 demand for healthier and calorie-reduced foods.

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

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

Raffinose is a trisaccharide composed of galactose, glucose, and fructose. It can be found in beans, cabbage, brussels sprouts, broccoli, asparagus, other vegetables, and whole grains. Raffinose can be hydrolyzed to D-galactose and sucrose by the enzyme α-galactosidase (α-GAL), an enzyme which in the lumen of the human digestive tract is only produced by bacteria in the large intestine. α-GAL also hydrolyzes other α-galactosides such as stachyose, verbascose, and galactinol, if present. The enzyme does not cleave β-linked galactose, as in lactose.

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

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">Agave syrup</span> Sweetener

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

Fructosides are glycosides where the glycone group is fructose.

<span class="mw-page-title-main">Sucrose phosphorylase</span> Class of enzymes

Sucrose phosphorylase is an important enzyme in the metabolism of sucrose and regulation of other metabolic intermediates. Sucrose phosphorylase is in the class of hexosyltransferases. More specifically it has been placed in the retaining glycoside hydrolases family although it catalyzes a transglycosidation rather than hydrolysis. Sucrose phosphorylase catalyzes the conversion of sucrose to D-fructose and α-D-glucose-1-phosphate. It has been shown in multiple experiments that the enzyme catalyzes this conversion by a double displacement mechanism.

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<span class="mw-page-title-main">Levansucrase</span> Enzyme used in the catalysis of sucrose

Levansucrase is an enzyme that catalyzes the chemical reaction

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

Levan is a naturally occurring fructan present in many plants and microorganisms. This polymer is made up of fructose, a monosaccharide sugar, connected by 2,6 beta glycosidic linkages. Levan can have both branched and linear structures of relatively low molecular weight. Branched levan forms a very small, sphere-like structure with basal chains 9 units long. The 2,1 branching allows methyl ethers to form and create a spherical shape. The ends of levan also tend to contain a glucosyl residue. Branched levan tends to be more stable than linear polysaccharides. However, the amount of branching and length of polymerization tends to vary among different species. The shortest levan is 6-kestose, a chain of two fructose molecules and a terminal glucose molecule.

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References

  1. Ide, Kaori; Shinohara, Mikako; Yamagishi, Shohei; Endo, Akihito; Nishifuji, Koji; Tochio, Takumi (2020). "Kestose supplementation exerts bifidogenic effect within fecal microbiota and increases fecal butyrate concentration in dogs". Journal of Veterinary Medical Science. 82 (1): 1–8. doi:10.1292/jvms.19-0071. ISSN   0916-7250. PMC   6983673 . PMID   31761826.
  2. 1 2 Heldt, Hans-Walter; Piechulla, Birgit (2011), "Polysaccharides are storage and transport forms of carbohydrates produced by photosynthesis", Plant Biochemistry, Elsevier, pp. 241–271, doi:10.1016/b978-0-12-384986-1.00009-0, ISBN   978-0-12-384986-1, S2CID   90618522 , retrieved 2021-12-29
  3. Ni, Dawei; Xu, Wei; Zhu, Yingying; Pang, Xiaoyang; Lv, Jiaping; Mu, Wanmeng (2021-01-02). "Insight into the effects and biotechnological production of kestoses, the smallest fructooligosaccharides". Critical Reviews in Biotechnology. 41 (1): 34–46. doi:10.1080/07388551.2020.1844622. ISSN   0738-8551. PMID   33153319. S2CID   226269151.
  4. 1 2 3 Campbell, Joy M.; Bauer, Laura L.; Fahey, George C.; Hogarth, A. J. C. L.; Wolf, Bryan W.; Hunter, Diane E. (1997-08-01). "Selected Fructooligosaccharide (1-Kestose, Nystose, and 1 F -β-Fructofuranosylnystose) Composition of Foods and Feeds". Journal of Agricultural and Food Chemistry. 45 (8): 3076–3082. doi:10.1021/jf970087g. ISSN   0021-8561.
  5. Suzuki, Nobuyuki; Aiba, Yuji; Takeda, Hiroyuki; Fukumori, Yasunori; Koga, Yasuhiro (2006). "Superiority of 1-kestose, the Smallest Fructo-oligosaccharide, to a Synthetic Mixture of Fructo-oligosaccharides in the Selective Stimulating Activity on Bifidobacteria". Bioscience and Microflora. 25 (3): 109–116. doi:10.12938/bifidus.25.109. ISSN   1342-1441.
  6. 1 2 3 Panesar, P.S.; Bali, V. (2016), "Prebiotics", Encyclopedia of Food and Health, Elsevier, pp. 464–471, doi:10.1016/b978-0-12-384947-2.00560-2, ISBN   978-0-12-384953-3 , retrieved 2021-12-29
  7. Watanabe, Ayako; Kadota, Yoshihiro; Kamio, Rina; Tochio, Takumi; Endo, Akihito; Shimomura, Yoshiharu; Kitaura, Yasuyuki (December 2020). "1-Kestose supplementation mitigates the progressive deterioration of glucose metabolism in type 2 diabetes OLETF rats". Scientific Reports. 10 (1): 15674. doi:10.1038/s41598-020-72773-2. ISSN   2045-2322. PMC   7515885 . PMID   32973311.
  8. Koga, Yasuhiro; Tokunaga, Shouji; Nagano, Jun; Sato, Fuyuhiko; Konishi, Kenta; Tochio, Takumi; Murakami, Youko; Masumoto, Natsuko; Tezuka, Jun-ichirou; Sudo, Nobuyuki; Kubo, Chiharu (December 2016). "Age-associated effect of kestose on Faecalibacterium prausnitzii and symptoms in the atopic dermatitis infants". Pediatric Research. 80 (6): 844–851. doi:10.1038/pr.2016.167. ISSN   0031-3998. PMC   5156669 . PMID   27537603.