Kestose

1-Kestose
	; 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
CAS Number	470-69-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16885;
ChemSpider	389087;
EC Number	207-429-4;
KEGG	C03661; G02515;
PubChem CID	440080;
UNII	02LN7O412C;
	InChI 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;
	SMILES 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
Chemical formula	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).
	Infobox references

Short description: Sugar from fructooligosaccharide group

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

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]
Ingredient	mg/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]

References

↑ 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" (in en). Journal of Veterinary Medical Science 82 (1): 1–8. doi:10.1292/jvms.19-0071. ISSN 0916-7250. PMID 31761826. PMC 6983673. https://www.jstage.jst.go.jp/article/jvms/82/1/82_19-0071/_article.
↑ ^2.0 ^2.1 Heldt, Hans-Walter; Piechulla, Birgit (2011), "Polysaccharides are storage and transport forms of carbohydrates produced by photosynthesis" (in en), Plant Biochemistry (Elsevier): pp. 241–271, doi:10.1016/b978-0-12-384986-1.00009-0, ISBN 978-0-12-384986-1, https://linkinghub.elsevier.com/retrieve/pii/B9780123849861000090, retrieved 2021-12-29
↑ 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" (in en). Critical Reviews in Biotechnology 41 (1): 34–46. doi:10.1080/07388551.2020.1844622. ISSN 0738-8551. PMID 33153319. https://www.tandfonline.com/doi/full/10.1080/07388551.2020.1844622.
↑ ^4.0 ^4.1 ^4.2 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" (in en). Journal of Agricultural and Food Chemistry 45 (8): 3076–3082. doi:10.1021/jf970087g. ISSN 0021-8561. https://pubs.acs.org/doi/10.1021/jf970087g.
↑ 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" (in en). Bioscience and Microflora 25 (3): 109–116. doi:10.12938/bifidus.25.109. ISSN 1342-1441. https://www.jstage.jst.go.jp/article/bifidus/25/3/25_3_109/_article.
↑ ^6.0 ^6.1 ^6.2 Panesar, P.S.; Bali, V. (2016) (in en), Prebiotics, Elsevier, pp. 464–471, doi:10.1016/b978-0-12-384947-2.00560-2, ISBN 978-0-12-384953-3, https://linkinghub.elsevier.com/retrieve/pii/B9780123849472005602, retrieved 2021-12-29
↑ 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" (in en). Scientific Reports 10 (1): 15674. doi:10.1038/s41598-020-72773-2. ISSN 2045-2322. PMID 32973311.
↑ Koga, Yasuhiro; Tokunaga, Shouji; Nagano, Jun; Sato, Fuyuhiko; Konishi, Kenta; Tochio, Takumi; Murakami, Youko; Masumoto, Natsuko et al. (December 2016). "Age-associated effect of kestose on Faecalibacterium prausnitzii and symptoms in the atopic dermatitis infants" (in en). Pediatric Research 80 (6): 844–851. doi:10.1038/pr.2016.167. ISSN 0031-3998. PMID 27537603.

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Kestose. Read more

[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" (in en). Journal of Veterinary Medical Science 82 (1): 1–8. doi:10.1292/jvms.19-0071. ISSN 0916-7250. PMID 31761826. PMC 6983673. https://www.jstage.jst.go.jp/article/jvms/82/1/82_19-0071/_article.

[:0-2] 2.0 ^2.1 Heldt, Hans-Walter; Piechulla, Birgit (2011), "Polysaccharides are storage and transport forms of carbohydrates produced by photosynthesis" (in en), Plant Biochemistry (Elsevier): pp. 241–271, doi:10.1016/b978-0-12-384986-1.00009-0, ISBN 978-0-12-384986-1, https://linkinghub.elsevier.com/retrieve/pii/B9780123849861000090, 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" (in en). Critical Reviews in Biotechnology 41 (1): 34–46. doi:10.1080/07388551.2020.1844622. ISSN 0738-8551. PMID 33153319. https://www.tandfonline.com/doi/full/10.1080/07388551.2020.1844622.

[:1-4] 4.0 ^4.1 ^4.2 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" (in en). Journal of Agricultural and Food Chemistry 45 (8): 3076–3082. doi:10.1021/jf970087g. ISSN 0021-8561. https://pubs.acs.org/doi/10.1021/jf970087g.

[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" (in en). Bioscience and Microflora 25 (3): 109–116. doi:10.12938/bifidus.25.109. ISSN 1342-1441. https://www.jstage.jst.go.jp/article/bifidus/25/3/25_3_109/_article.

[:2-6] 6.0 ^6.1 ^6.2 Panesar, P.S.; Bali, V. (2016) (in en), Prebiotics, Elsevier, pp. 464–471, doi:10.1016/b978-0-12-384947-2.00560-2, ISBN 978-0-12-384953-3, https://linkinghub.elsevier.com/retrieve/pii/B9780123849472005602, 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" (in en). Scientific Reports 10 (1): 15674. doi:10.1038/s41598-020-72773-2. ISSN 2045-2322. PMID 32973311.

[8] Koga, Yasuhiro; Tokunaga, Shouji; Nagano, Jun; Sato, Fuyuhiko; Konishi, Kenta; Tochio, Takumi; Murakami, Youko; Masumoto, Natsuko et al. (December 2016). "Age-associated effect of kestose on Faecalibacterium prausnitzii and symptoms in the atopic dermatitis infants" (in en). Pediatric Research 80 (6): 844–851. doi:10.1038/pr.2016.167. ISSN 0031-3998. PMID 27537603.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]