Aglycone Explained

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.

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

• Glucoside

Notes and References

1. McNaught AD . Nomenclature of carbohydrates (IUPAC Recommendations 1996). . Pure and Applied Chemistry . January 1996 . 68 . 10 . 1919–2008 . 10.1351/pac199668101919 . 19741698 . https://web.archive.org/web/20161112074844/http://www.chem.qmul.ac.uk/iupac/2carb/33.html. 12 November 2016. dead. 2-Carb-33 . free .
2. Book: IUPAC Compendium of Chemical Terminology . 2nd . 1997 . 67 . 1312 .
3. Simonet AM, Durán AG, Pérez AJ, Macías FA . Features in the NMR spectra of the aglycones of Agave spp. saponins. HMBC method for aglycone identification (HMAI) . Phytochemical Analysis . 32 . 1 . 38–61 . January 2021 . 32515107 . 10.1002/pca.2946 . 219549980 .
4. Vikram A, Jayaprakasha GK, Patil BS . Simultaneous determination of citrus limonoid aglycones and glucosides by high performance liquid chromatography . Analytica Chimica Acta . 590 . 2 . 180–186 . May 2007 . 17448343 . 10.1016/j.aca.2007.03.029 .
5. Giménez-Bastida JA, González-Sarrías A, Larrosa M, Tomás-Barberán F, Espín JC, García-Conesa MT . 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 . May 2012 . 22648625 . 10.1002/mnfr.201100677 .
6. Grossi C, Rigacci S, Ambrosini S, Ed Dami T, Luccarini I, Traini C, Failli P, Berti A, Casamenti F, Stefani M . 6 . The polyphenol oleuropein aglycone protects TgCRND8 mice against Aß plaque pathology . PLOS ONE . 8 . 8 . e71702 . 2013-08-08 . 23951225 . 3738517 . 10.1371/journal.pone.0071702 . 2013PLoSO...871702G . Masuo . Ohno . free .