Trehalulose Explained

Trehalulose is a disaccharide made up of a molecule of fructose bound to a molecule of glucose. Like isomaltulose, it is a structural isomer of sucrose that is present in small quantities in honey.[1] It makes up 50% of sugars in the honeydew of silverleaf whiteflies[2] [3] and is synthesised from sucrose by some bacteria,[4] [5] such as Protaminombacter rubrum. Because the anomeric carbon of the fructose moiety is not involved in the glycosidic bond, it is a reducing sugar.[6]

Physiology

Because the fructose and glucose molecules are linked by a 1,1 glycosidic bond, which is more stable than the 1,2 glycosidic bond in sucrose, it is broken down more slowly than sucrose in the small intestine, giving it a lower glycemic index. This more stable bond also means that it cannot be utilised by Streptococcus mutans, and it is therefore non-cariogenic.[7]

Properties

Unlike isomaltulose, trehalulose strongly resists crystallisation, and forms an amorphous solid when dried. Its sweetness relative to sucrose has been estimated as between 0.4[8] and 0.7.[9]

It has a specific rotation of

20
[\alpha]
D

=+50

°.

Honey from stingless bees

In 2020 researchers at the University of Queensland found that some species of stingless bee in Australia, Malaysia, and Brazil produce honey containing between 13% and 44% trehalulose rather than the usual glucose and fructose. The university's findings supported the long-standing claims of Indigenous Australian people that native honey is beneficial for human health.[10] [11] In 2021 the same researchers discovered that the bees convert all sucrose from nectar into trehalulose.[12]

References

  1. Book: Wolfgang Gerhartz . Ullmann's encyclopedia of industrial chemistry / Vol. A. Alphabetically arranged articles. 25, Starch and other polysaccharides to surfactants.. 1994. VCH Verl.-Ges. 3-527-20125-4. 5., completely rev . Weinheim. 426–427. 311987978.
  2. Salvucci. Michael E.. Wolfe. Gregory R.. Hendrix. Donald L.. 1997-05-01. Effect of sucrose concentration on carbohydrate metabolism in Bemisia argentifolii: Biochemical mechanism and physiological role for trehalulose synthesis in the silverleaf whitefly. Journal of Insect Physiology. en. 43. 5. 457–464. 10.1016/S0022-1910(96)00124-2. 0022-1910.
  3. Book: Dictionary of carbohydrates with CD-ROM. Collins, P. M.. 29 November 2005. 0-8493-7765-X. 2nd. Boca Raton. 538. 70262506.
  4. Hamerli. Dénes. Birch. Robert G.. 2011. Transgenic expression of trehalulose synthase results in high concentrations of the sucrose isomer trehalulose in mature stems of field-grown sugarcane. Plant Biotechnology Journal. en. 9. 1. 32–37. 10.1111/j.1467-7652.2010.00528.x. 20492546. 1467-7652. free.
  5. Tsuyuki. Ken'ichiro. Sugitani. Toshiaki. Miyata. Yukie. Ebashi. Tadishi. Nakajima. Yoshikazu. 1992. Isolation and characterization of isomaltulose- and trehalulose-producing bacteria from Thailand soil.. The Journal of General and Applied Microbiology. 38. 5. 483–490. 10.2323/jgam.38.483. 1349-8037. free.
  6. Book: Rosenplenter. Kurt. Handbuch Süßungsmittel. Lipinski. Prof Dr Gert-Wolfhard von Rymon. Nöhle. Prof Dr Ulrich. 2007-01-01. Behr's Verlag DE. 978-3-89947-947-8. 258. de.
  7. Ooshima. T.. Izumitani. A.. Minami. T.. Fujiwara. T.. Nakajima. Y.. Hamada. S.. 1991. Trehalulose Does Not Induce Dental Caries in Rats Infected with Mutans Streptococci. Caries Research. en . 25. 4. 277–282. 10.1159/000261376. 0008-6568. 1913765.
  8. Process for producing a saccharide composition containing trehalulose. 1997-09-10. EP. 0794259. Hayashibara Seibutsu Kagaku Kenkyujo KK. Nishimoto. Tomoyuki. Chaen. Hiroto. Fukuda. Shigeharu. Miyake. Toshio.
  9. Ravaud. Stéphanie. Watzlawick. Hildegard. Haser. Richard. Mattes. Ralf. Aghajari. Nushin. 2005-01-01. Expression, purification, crystallization and preliminary X-ray crystallographic studies of the trehalulose synthase MutB from Pseudomonas mesoacidophila MX-45. Acta Crystallographica Section F. 61. 1. 100–103. 10.1107/S1744309104030623. 1744-3091. 1952383. 16508103.
  10. Web site: Layt. Stuart. 2020-07-23. Scientists say native stingless bee honey hits the sweet spot. 2020-07-27. Brisbane Times. en.
  11. Fletcher. Mary T.. Hungerford. Natasha L.. Webber. Dennis. Carpinelli de Jesus. Matheus. Zhang. Jiali. Stone. Isobella S. J.. Blanchfield. Joanne T.. Zawawi. Norhasnida. 2020-07-22. Stingless bee honey, a novel source of trehalulose: a biologically active disaccharide with health benefits. Scientific Reports. en. 10. 1. 12128. 10.1038/s41598-020-68940-0. 32699353. 7376065. 2020NatSR..1012128F. 2045-2322. free.
  12. News: Native bees make a healthy honey no others make, and now we know how. ABC News. 27 August 2021.

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Trehalulose".

Except where otherwise indicated, Everything.Explained.Today is © Copyright 2009-2024, A B Cryer, All Rights Reserved. Cookie policy.