C-Glucosidation

Vicinin-2 and lucenin-2 = apigenin and luteolin 6,8-di C-glucosides Gin = glucuronic acid Rhm = rhamnose. 

C-Glucosidation. Reaction of the protected a-D-glucopyranosyl chloride 1 with silyl enol ethers activated with AgOTf results in a-C-glucosyl esters or ketones. 

Scheme 2.5 One-pot conversions of D-glucose into hydrophilic furans or, alternatively, into C-glucosides by reaction with acetylacetone. " ...

One final, but less direct, ploy is that we have prepared the nitromethyl -D-C-glucoside 47 and hope to be able to alkylate this molecule on carbon [33,34]. 

Figure 5 shows the results of inhibition experiments involving the D-gluco-sides 37 (n = 1-3) and a cellobiohydrolase from Trichoderma reesei. The best inhibition was achieved with the epoxypentyl /J-D-C-glucoside, a result which corresponds nicely to the 0-glycoside series where the epoxybutyl -o-gluco-side 6 (n = 2) was the most effective inhibitor. 

Buko, V. et al.. Inhibition of oxidative damage of red blood cells and liver tissue by genistein-8-C-glucoside, Adv. Exp. Med. Biol, 500, 271, 2001. 

El-Hela, A.A., Singab, A.B., and El-Azizi, M.M.J., Flavone-C-glucosides from Verbena bipinna-tifida Nutt growing in Egypt, J. Pharm. Sci, 25, 232, 2000. 

Majumder, P.L. and Sen, R.C., Chemical constituents of the orchid Tylostylis discolor, occurrence of fiavonoid C-glucoside in Orchidaceae plant, J. Indian Chem. Soc., 71, 649, 1994. 

Tsiklauri, G.C. and Shalashvili, A.G., Flavonoid C-glucosides of tangerine Iveria leaves, Soobsh-cheniya Akad. Nauk Gruzii, 151, 131, 1995. 

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