Curcumin (CUR) is one of the active ingredients of turmeric. Numerous studies have demonstrated anti-ineffective potential of CUR. However, limited water solubility, low stability, and bioavailability all prevent the development of the pharmaceutical potential of CUR. Asymmetric natural and synthesized analogs of CUR have demonstrated superior biological performance. In addition, molecules containing rigid backbone were characterized with higher stability. However, their behavior in aqueous solutions is not well understood. It is believed that hydrogen-transfer and keto-enol tautomerization are responsible for the bioactivity mechanisms of CUR and its analogs. Nevertheless, most curcuminoids are reported as enol forms in solid and solution states. 1H Nuclear magnetic resonance (NMR) spectroscopy is a powerful technique that allows the identification of individual hydrogen atoms in an organic molecule. With the clever design 1H NMR can provide information on how molecules change in the solution. To the best of our knowledge, there have been no reports on keto-enol tautomerization of synthetic asymmetric curcuminoids. In this study, we applied variable temperature (VT) 1H NMR spectroscopy to investigate the conversion of enol and keto form of several asymmetric curcuminoids in a variety of solvents. The results of the study provide information valuable for future biological applications of novel curcuminoids.

Study of keto-enol tautomerization of several asymmetric curcuminoids using variable temperature spectroscopy

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