7-Docosahexaenoyl-Quercetin

Sarah Mazzotta,Maria Enrica Di Cocco,Fabio Sciubba,Francesca Aiello,Gabriele Carullo

doi:10.3390/m1203

Sarah Mazzotta, Maria Enrica Di Cocco + Show 3 more

Open Access

https://doi.org/10.3390/m1203

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Abstract

Fatty acids and polyphenols represent different classes of pharmacologically active molecules. Hybrid derivatives of these compounds are interesting therapeutic tools. They could be obtained using enzymatic approaches, which allow regioselective derivatizations. In this short note, the pancreatic porcine lipase was employed to mediate the regioselective synthesis of 7-docosahexaenoyl-quercetin was described. The C-7 regioisomer formation was confirmed by 1H-NMR experiment. Generally, in this approach the alcoholic OH- was preferred when present. Nevertheless, in this case, it was demonstrated that the hindrance of the acyl group is a variable to obtain a good regioselectivity in C-7 position, employing only one-step reaction.

Highlights

The free fatty acids are essential constituents of foods, plants, and humans
We evaluated the use of docosahexaenoic acid (DHA) as acylating agent and Pancreatic Porcine Lipase (PPL) as catalyst for polyphenols, selective quercetin derivatization
Results and Discussion for selective quercetin derivatization. This procedure demonstrates that, in the case of DHA, only the C-7 works, ester was obtained in good yield

Summary

Introduction

The free fatty acids are essential constituents of foods, plants, and humans. Most of them show important biological properties due to they are endogenous ligands of different biological targets [1]. No reports are available for the synthesis of quercetin esters using Novozyme 435® [9]. Molbank 2021, 2021, M1203 enzyme occurred helpful for the preparation of C-3 oleoyl esters of other polyphenols, including morin and catechin [14].

Results

Conclusion