Chalcone glycosides

Certain flavanone and chalcone glycosides are difficult to dissolve in methanol, ethanol, or alcohol-water mixtures. Flavanone solubility depends on the pH of water-containing solutions. 

Anam, E.M., Novel flavone and chalcone glycosides from Clerodendron phlomidis (Verbenaceae), Indian J. Chem., 36B, 897, 1997. 

Cioffi, G. et al.. Antioxidant chalcone glycosides and flavanones from Madura (Chlorophora) tinctoria, J. Nat. Prod., 66, 1061, 2003. 

Redl, K., Davis, B., and Bauer, R., Chalcone glycosides from Bidens campylotheca. Phytochemistry, 32, 218, 1993. 

Chalcones are unsaturated and, along with dihydrochalcones, contain an open pyronic cycle and a carbon skeleton numbered in a way different from other flavonoids, Fig. (8, 9). Native chalcone glycosides tend to transform into flavanone glycosides during extraction procedures. Chalcones per se are therefore of restricted occurence in foods [35]. 

Licuraside (= Isoliquiritigenin-4-(3-D-apiofuranosyl-2 - 3-D-Glc 2, 4, 4-Trihydroxychalcone-4-P-D-apiofuranosyl-2 - 3-D- glucoside) (chalcone glycoside) Glycyrrhiza glabra (Fabaceae) PEP (27 pM) [116]... 

Trihydroxychalcone) (chalcone) glycoside in Dahlia variabilis (Asteraceae) [flower], Glycyrrhiza glabra (Fabaceae) [root, rhizome] uncoupler) [PAI, yellow]... 

Litvinenko, V.L Chalcone Glycoside of Glycyrrhiza glabra. Dokl. Akad. Nauk (SSSR), 155, 600 (1964) Chem. Abstr., 60, 14579d (1964). 

Miething, H., and A. Speicher-Brinker Neolicuroside, a New Chalcone Glycoside from the Roots of Glycyrrhiza glabra. Arch. Pharm. (Weinheim), 322, 141 (1989) Chem. Abstr., Ill, 4253t (1989). 

Ninomiya M, Efdi M, Inuzuka T, Koketsu M (2010) Chalcone glycosides from aerial parts of Brassica rapa L. hidabeni , turnip. Phytochem Lett 3 96-99... 

Hara H, Nakamura Y, Ninomiya M, Mochizuki R, Kamiya T, Aizenman E, Koketsu M, Adachi T (2011) Inhibitory effects of chalcone glycosides isolated from Brassica rapa L. hidabeni and their synthetic derivatives on LPS-induced NO production in microglia. Bioorg Med Chem 19 5559-68... 

Tiwari KP, Minocha PK 1980 A chalcone glycoside from Abiespindrow. Planta 19 2501 -2503... 

Contains a complex mixture of red and yellow pigments including 20-30% safflower yellow (safflower yellow SY) which is composed of safflomin A (75%), SY-2 (15%), SY-3, and SY-4, all chalcones glycosides of chalcone (e.g., carthamin yellow) and qui-none (e.g., carthamone red), with the latter predominant in the commercial product also colorless flavonoids and flavonoid glycosides (carthamidin, isocarthamidin, neocarthamin) safflower polysaccharide (glucose, xylose. 

Chalcones are not flavan derivatives since they lack the characteristic central heterocycle. They are converted spontaneously into true flavan derivatives, the flavanones, the reacjtion occurring particularly readily in acidic medium. They play a central role in the biosynthesis of the flavan derivatives. Chalcone glycosides oceur in relatively high quantities in the flowers of several of the Compositae and Leguminosae, which, as a result. 

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