959833-92-2Relevant academic research and scientific papers
Tunable microwave-assisted method for the solvent-free and catalyst-free peracetylation of natural products
Oliverio, Manuela,Costanzo, Paola,Nardi, Monica,Calandruccio, Carla,Salerno, Raffaele,Procopio, Antonio
, p. 2222 - 2233 (2016)
Background: The peracetylation is a simple chemical modification that can be used to enhance the bioavailability of hydrophilic products and to obtain safe and stable pro-drugs. Results: A totally green, solvent-free and catalyst-free microwave (MW)-assisted method for peracetylation of natural products such as oleuropein, alpha-hederin, quercetin and rutin is presented. By simply tuning the MW heating program, polyols with chemical diverse -OH groups or thermolabile functionalities can be peracetylated to improve the biological activity without degradation of the natural starting molecules. An evaluation of the process greenness was performed. Conclusion: The method is potentially universally applicable for green acetylation of hydrophilic biological molecules, potentially easily scalable for industrial applications, including pharmaceutical, cosmetic and food industry.
Enzymatic acylation of flavonoids: Effect of the nature of the substrate, origin of lipase, and operating conditions on conversion yield and regioselectivity
Chebil, Latifa,Anthoni, Julie,Humeau, Catherine,Gerardin, Christine,Engasser, Jean-Marc,Ghoul, Mohamed
, p. 9496 - 9502 (2008/09/17)
The conversion yield at equilibrium, the initial rate, and the regioselectivity of the enzymatic acetylation of aglycone flavonoids (quercetin, naringenin, hesperetin, and chrysin) were investigated and compared to those obtained with a glycosylated one (isoquercitrin). The effects of a wide range of operating conditions were quantified. Fourier transform infrared spectrometry (FT-IR), NMR, and high performance liquid chromatography electrospray ionization mass spectrometry (HPLC-ESI-MS) analyses showed that for glycosylated flavonoids, in the presence of Candida antarctica (CAL-B), the acetylation occurred on the 2″-OH, 3″-OH, and 6″-OH of the glucose part, while with Pseudomonas cepacea lipase (PSL-C) acetylation takes place on 6″-OH of the sugar and 4′-OH of the B-ring. For aglycone flavonoids, the acetylation occurred only with PSL-C on 4′-OH, 3′-OH, and 7-OH hydroxyls. The conversion yield and the number and the relative proportions of the synthesized products were found dependent on the nature of the enzyme, the molar ratio, and the flavonoid structure. The initial rate was affected only by the origin of the enzyme.
