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Cyclitol

Cyclitols are a class of compounds in organic chemistry that are cycloalkanes containing at least three hydroxyl groups, each attached to a different ring carbon atom. The general formula for an unsubstituted cyclitol is \(C_nH_{2n-x}(OH)_x\) or \(C_nH_{2n}O_x\), where \(3 \leq x \leq n\). Cyclitols can also include compounds with various functional groups substituted for hydrogen or those with one or more double bonds in the ring[1].

Cyclitols and their derivatives play important roles in plants, acting as compatible solutes formed in response to salt or water stress. Some cyclitols, such as quinic or shikimic acid, are part of hydrolysable tannins. They exist in several structural isomers, which can further exist in multiple stereoisomers, including enantiomers. For example, inositol, a well-known cyclitol, has nine stereoisomers, two of which are enantiomers[1].

The IUPAC has provided a nomenclature system for cyclitol stereoisomers. Examples of naturally occurring cyclitols include:

Cyclitols are also associated with various biological functions and potential therapeutic applications. For instance, myo-inositol (MI) and its derivatives are key in many cellular processes such as signal transduction, phosphate storage, cell wall formation, membrane biogenesis, and osmoregulation. MI is a common cyclitol in eukaryotic cells and serves as a precursor for structural lipids like phosphatidylinositols (PIs) and phosphatidylinositol phosphate lipids (PIPs)[2].

Research has also explored the connection between cyclitols and neurodegenerative diseases, suggesting that dietary supplementation of MI may have a promising effect on the treatment of such disorders[2].

Cyclitols have been studied for their antioxidative properties, although they exhibit very low antioxidative properties compared to other compounds like flavanones and glutathione. However, when combined with these compounds, there can be a significant increase in antioxidative activity[4].

In summary, cyclitols are a diverse group of compounds with various isomers and derivatives that play significant roles in plant physiology and have potential therapeutic applications in human health, particularly in the treatment of metabolic and neurodegenerative diseases[1][2].

Citations:

[1] https://en.wikipedia.org/wiki/Cyclitol

[2] https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10180955/

[3] https://onlinelibrary.wiley.com/doi/10.1002/cbdv.202301064

[4] https://www.mdpi.com/1420-3049/27/1/158

[5] https://www.merriam-webster.com/dictionary/cyclitol

[6] https://iupac.qmul.ac.uk/cyclitol/

[7] https://link.springer.com/article/10.1007/s11101-020-09677-6

[8] https://www.researchgate.net/publication/329379676_The_Healing-Promoting_Properties_of_Selected_Cyclitols-A_Review

[9] https://www.sciencedirect.com/topics/biochemistry-genetics-and-molecular-biology/cyclitol

[10] https://www.degruyter.com/document/doi/10.1351/pac197437010283/pdf

[11] https://www.mdpi.com/2072-6643/11/10/2314

[12] https://www.sciencedirect.com/topics/agricultural-and-biological-sciences/cyclitol

[13] https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6835238/

[14] https://www.frontiersin.org/articles/10.3389/fchem.2022.950433

[15] https://www.collinsdictionary.com/us/dictionary/english/cyclitol

[16] http://publications.iupac.org/pac/1974/pdf/3701x0283.pdf

[17] https://www.yourdictionary.com/cyclitol

[18] https://www.researchgate.net/figure/Various-types-of-cyclitols_fig1_341114016

[19] https://en.wiktionary.org/wiki/cyclitol

[20] https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6316775/