Aglycone

An aglycone (aglycon[1] or genin) is the chemical compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom.[2] For example, the aglycone of a cardiac glycoside would be a steroid molecule.

Chemical structures of digoxin (top) and its aglycone
digoxigenin (bottom)

Detection

A way to identify aglycone is proposed to extract it from Agave spp. by using H-NMR and Heteronuclear multiple bond correlation (HMBC) experiments. The HMBC experiment can be combined with other techniques such as mass spectrometry to further examine the structure and the function of aglycone.[3]

Samples of glycones and glycosides from limonoids can be simultaneously quantified through a high performance liquid chromatography (HPLC) method, where a binary solvent system and a diode array detector separate and detect them at a sensitivity of 0.25-0.50 μg.[4]

Clinical significance

A study on molecular markers in human aortic endothelial cells published that aglycone stopped cell migration but not monocyte adhesion, which is the initial step of atherosclerotic plaque formation.[5] Another study exploring the benefits of extra virgin olive oil consumption in preventing age-related neurodegenerative diseases found aglycone greatly increased the cognitive performance of mice. The aglycone-fed mice displayed strong autophagic reactions, mTOR regulation, and reduced plaque deposits and ß-amyloid levels.[6]

See also

References
  1. McNaught AD (January 1996). "Nomenclature of carbohydrates (IUPAC Recommendations 1996)". Pure and Applied Chemistry. 68 (10): 1919–2008. doi:10.1351/pac199668101919. S2CID 19741698. Archived from the original on 12 November 2016. 2-Carb-33
  2. IUPAC Compendium of Chemical Terminology. Vol. 67 (2nd ed.). 1997. p. 1312.
  3. Simonet AM, Durán AG, Pérez AJ, Macías FA (January 2021). "Features in the NMR spectra of the aglycones of Agave spp. saponins. HMBC method for aglycone identification (HMAI)". Phytochemical Analysis. 32 (1): 38–61. doi:10.1002/pca.2946. PMID 32515107. S2CID 219549980.
  4. Vikram A, Jayaprakasha GK, Patil BS (May 2007). "Simultaneous determination of citrus limonoid aglycones and glucosides by high performance liquid chromatography". Analytica Chimica Acta. 590 (2): 180–186. doi:10.1016/j.aca.2007.03.029. PMID 17448343.
  5. Giménez-Bastida JA, González-Sarrías A, Larrosa M, Tomás-Barberán F, Espín JC, García-Conesa MT (May 2012). "Ellagitannin metabolites, urolithin A glucuronide and its aglycone urolithin A, ameliorate TNF-α-induced inflammation and associated molecular markers in human aortic endothelial cells". Molecular Nutrition & Food Research. 56 (5): 784–796. doi:10.1002/mnfr.201100677. PMID 22648625.
  6. Grossi C, Rigacci S, Ambrosini S, Ed Dami T, Luccarini I, Traini C, et al. (2013-08-08). Ohno M (ed.). "The polyphenol oleuropein aglycone protects TgCRND8 mice against Aß plaque pathology". PLOS ONE. 8 (8): e71702. Bibcode:2013PLoSO...871702G. doi:10.1371/journal.pone.0071702. PMC 3738517. PMID 23951225.
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