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Draft:Cyclodextran

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  • Comment: The "Potential applications" section appears VERY promotional and possibly also original research. Theroadislong (talk) 08:08, 23 October 2024 (UTC)
Structure of cyclodextran (CI-8)

Cyclodextran, also known as cyclic isomaltooligosaccharide (CI), is a non-reducing sugar derived from dextran. It is characterized by its cyclized structure and composition of alpha-1,6 bonds.

Comparison with cyclodextrin

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Although CI shares the common constituent of glucose, its linkage pattern is distinct from that of another cyclic oligosaccharide, cyclodextrin (CD), which consists of alpha-1,4 bonds. The structures of 11 types of CIs, with glucose units ranging from seven to seventeen, have been determined. CI-10, in particular, has strong inclusion complex-forming ability. Four Bacillus strains and two Paenibacillus strains were identified as novel CI-producing bacteria. These strains mainly produced CI-10 to CI-12, but larger CIs up to CI-17 were also identified..[1] While CIs with high molecular weights, incorporating more than eighteen glucose units, also exist, research predominantly focuses on CIs with seven to twelve glucose units (CI-7 to CI-12) due to their higher prevalence and relative ease of purification.

History

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Initial discovery

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CI was first discovered in 1993. In a liquid culture using dextran as a carbon source, the researchers noticed that a strain of bacteria isolated from soil produced and accumulated a substance different from linear isomaltooligosaccharides.[2]

Natural occurrence

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This substance, which was revealed to have a structure where 7 to 9 glucose molecules were connected in a circular fashion via alpha-1,6 bonds, was named cyclodextran. Given that dextran and isomaltooligosaccharides are naturally occurring, it was speculated that CI might also be a natural product. A trace amount of CI from CI-7 to CI-9 was confirmed when attempts were made to detect CI from brown sugar.[3]

Industrial production

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CI is produced using two primary methods. One involves converting sucrose into dextran, which is then cyclized. The second method uses starch directly. Commercial production typically favors sucrose as the starting material. CITase is employed to convert dextran into CI. A commercially available product, CI-Dextran mix, contains at least 13% CI by weight and is available from Wellneo Sugar Co., Ltd. [4]. Studies indicate that CI-Dextran mix may help reduce dental plaque. [5] Additionally, research shows that bacterial strains, such as Paenibacillus sp. 598K, can produce CIs from starch, even without dextran. [6]

Functional properties

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Inhibition of Glucosyltransferase (GTF)

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CI specifically inhibits the activity of glucosyltransferase (GTF), a key enzyme in Streptococcus mutans, thereby suppressing the formation of glucan, a major component of dental plaque.[7]

Mechanism of action

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CI is believed to inhibit GTF through competitive inhibition by binding to its active site[8] [9] GTF plays a crucial role in plaque formation. However, the precise details of this inhibition mechanism are still under investigation.

Solubility enhancement

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CI enhances the solubility of some difficult-to-dissolve substances. [10] Research has shown that CI can form inclusion complexes with various hydrophobic compounds, enhancing their solubility and stability. [11]

Chemical properties

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One notable characteristic of CI is its lack of sweetness, indicating that it does not function as a sweetener. Due to its cyclic structure, CI has no terminal groups, and as a result, it does not exhibit reducing properties. CI is a non-reducing oligosaccharide with strong stability against heat, acid, and alkali, attributed to its cyclic structure. CI has high solubility in water and can dissolve in an equivalent or smaller amount of water.

Usage

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Prevention of dental diseases

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CI, a functional oligosaccharide, has been shown to inhibit the formation of dental plaque, which plays a critical role in the development of dental caries and periodontal disease. As plaque accumulation is a primary contributor to these oral health conditions, [12] reducing plaque through CI consumption may support their prevention. Studies demonstrate that CI inhibits the activity of glucosyltransferase (GTF), an enzyme responsible for glucan formation, thus limiting plaque accumulation. Furthermore, a clinical trial found that the CI-Dextran mix reduced plaque formation. Healthy adults consuming the product experienced a significant reduction in plaque buildup, with no reported adverse events. [13]

Potential applications

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CI's unique mechanism of action inhibits the glucosyltransferase (GTF) [14] without exhibiting bactericidal effects, meaning it does not harm beneficial bacteria. This property allows CI to remain effective even when consumed alongside sugars. Its potential applications extend to food, cosmetics, and possibly over-the-counter drugs. A key advantage of CI, compared to similar substances, is its ability to inhibit plaque formation without disrupting the balance of the oral microbiota, even in the presence of sugars.

References

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  1. ^ Funane K, Terasawa K, Mizuno Y, Ono H, Gibu S, Tokashiki T, Kawabata Y, Kim YM, Kimura A, Kobayashi M (December 2008). "Isolation of Bacillus and Paenibacillus Bacterial Strains That Produce Large Molecules of Cyclic Isomaltooligosaccharides". Bioscience, Biotechnology, and Biochemistry. 72 (12): 3277–80. doi:10.1271/bbb.80384. PMID 19060390.
  2. ^ Oguma T, Horiuchi T, Kobayashi M (January 1993). "Novel Cyclic Dextrins, Cycloisomaltooligosaccharides, from Bacillus sp. T-3040 Culture". Bioscience, Biotechnology, and Biochemistry. 57 (7): 1225–27. doi:10.1271/bbb.57.1225. PMID 27281012.
  3. ^ Tokasiki T, Kinjyo K, Funane K, Itou H (2007). "Novel Cycloisomaltooligosaccharides Contained in the Kokuto Produced in Okinawa Prefecture". Journal of Applied Glycoscience. 54 (1): 27–30. doi:10.5458/JAG.54.27.
  4. ^ "CI-Dextran mix | Wellneo Sugar Co., Ltd".
  5. ^ Teshima, Hikaru; Kato, Hikaru; Nakamura, Yasuyuki; Suzuki, Naoko; Horiuchi, Masahiko (2024). "Production of Cyclodextran and Its Application". Functional Foods in Health and Disease. 14 (2): 143–156. doi:10.31989/ffhd.v14i2.1324.
  6. ^ Ichinose H, Suzuki R, Miyazaki T, Kimura K, Momma M, Suzuki N, Fujimoto Z, Kimura A, Funane K (2017). "Paenibacillus sp. 598K 6-α-glucosyltransferase is essential for cycloisomaltooligosaccharide synthesis from α-(1 → 4)-glucan". Applied Microbiology and Biotechnology. 101 (10): 4115–4128. doi:10.1007/s00253-017-8174-z. PMID 28224195.
  7. ^ Kobayashi M; Funane K; Oguma T (1995). "Inhibition of Dextran and Mutan Synthesis by Cycloisomaltooligosaccharides". Bioscience, Biotechnology, and Biochemistry. 59 (10): 1861–65. doi:10.1271/bbb.59.1861. PMID 8534976.
  8. ^ Kobayashi M, Oguma T (1995). "Cyclodextran and anti-dental-caries action". Japan Food Science. 34 (1): 26–31.
  9. ^ Imamura W, Yamasaki T, Kato H, Ishikawa T (2024). "Computational study on the inhibition mechanism of cyclodextran against GTF-SI from Streptococcus mutans focusing on the glucan-binding domain". Carbohydrate Polymer Technologies and Applications. 7: 100473. doi:10.1016/j.carpta.2024.100473.
  10. ^ Hong, Seong-Jin; Park, Bo-Ram; Lee, Byung-Hoo; Park, Boo-Su; Kim, Young-Min (2023). "New Potential Applications of Cyclodextran in High Water Solubility and in Vitro Digestive System". SSRN. SSRN 4477437.
  11. ^ Oguma, Tetsuya; Kawamoto, Hiroshi (2003). "Production of Cyclodextran and Its Application". Trends in Glycoscience and Glycotechnology. 15 (82): 91–99. doi:10.4052/tigg.15.91.
  12. ^ Gurenlian, JoAnn R. (2007). "The Role of Dental Plaque Biofilm in Oral Health". Journal of Dental Hygiene. 81 (5).
  13. ^ Teshima, Hikaru; Kato, Hikaru; Nakamura, Yasuyuki; Suzuki, Naoko; Horiuchi, Masahiko (2024). "Production of Cyclodextran and Its Application". Functional Foods in Health and Disease. 14 (2): 143–156. doi:10.31989/ffhd.v14i2.1324.
  14. ^ Kobayashi M; Funane K; Oguma T (1995). "Inhibition of Dextran and Mutan Synthesis by Cycloisomaltooligosaccharides". Bioscience, Biotechnology, and Biochemistry. 59 (10): 1861–65. doi:10.1271/bbb.59.1861. PMID 8534976.
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