New Synthetic Glucosyl-Curcuminoids, and their 1H and 13C NMR Characterization, from Curcuma longa L.

Abstract

Turmeric extracts, among which curcumin and bis-demethoxycurcumin, are by far known for their therapeutic activities. In this study we propose easy and low cost synthetic pathways in order to obtain glucosyl-curcuminoids, safe and water soluble potential drugs and dyes, which may be implied in different fields ranging from pharmacology to food chemistry. The complete (1)H and (13)C NMR characterization of naturally occurring curcumin, bis-demethoxycurcumin and new synthetic glucosyl-curcuminoids is reported.

Discovering Bisdemethoxycurcumin from Curcuma longa rhizome as a potent small molecule inhibitor of human pancreatic α-amylase, a target for type-2 diabetes

“…1 -8,8' 126.2, C-9,9' 130.8, C-10,10' 116.3, C-11 11' 160.2, C-12,12' 116.3, C-13,13' 130.8. This was also compared and found to be in agreement with the spectral analysis and chemical shift data reported in literature (Saladini et al, 2009). …”

“…Chemical shifts (d) were referenced to the solvent peaks and then expressed in parts per million (ppm) according to (Saladini et al, 2009). …”

Evaluation of saffron (Crocus sativus L.) adulteration with plant adulterants by 1H NMR metabolite fingerprinting

“…ppm) resulted in full agreement with previously reported data(Saladini, Lazzari, Pignedoli, Rosa, Spagnolo, & Ferrari, 2009). Curcuminoid signals could be easily recognized in the saffron adulterated with turmeric extract (top trace, panel A) by comparison with the pure saffron spectrum.…”

4′-O-Methylglycosylation of Curcumin by Beauveria bassiana

“…To the best of our knowledge, although the syntheses of glycosides of curcumin by plant cell suspension cultures [10] and chemical methods [18] have been reported, this is first time that a new curcumin glycoside has been synthesized by fungal biotransformation. In our previous research on the biotransformation of quercetin by B. bassiana [13], the enzymes responsible for the 4'-O-methylglucosylation were found to be intracellular enzymes, which take the substrate from the medium into the cells.…”

“…To the best of our knowledge, although the syntheses of glycosides of curcumin by plant cell suspension cultures [10] and chemical methods [18] have been reported, this is first time that a new curcumin glycoside has been synthesized by fungal biotransformation. The 4'-Omethyl-glucosylation by B. bassiana ATCC 7159 is more advantageous than chemical methods in that it is an environmentally benign process and requires no toxic chemical reagents.…”