Scalable Preparation of High Purity Rutin Fatty Acid Esters

Abstract

Investigations into expanded uses of modified flavonoids are often limited by the availability of these high purity compounds. As such, a simple, effective and relatively fast method for isolation of gram quantities of both long and medium chain fatty acid esters of rutin following scaled-up biosynthesis reactions was established. Acylation reactions of rutin and palmitic or lauric acids were efficient in systems containing dried acetone and molecular sieves, yielding from 70-77% bioconversion after 96 h. Thereafter, high purity isolates ([97%) were easily obtained in significant quantities following a two-step solvent purification procedure whereby excess fatty acid substrate was first removed in a heptane/water (4:1, v/v) system, followed by selective ester extraction using an ethyl acetate/water system (1:6, v/v) at elevated temperature.

The antioxidative effect of lipophilized rutin and dihydrocaffeic acid in fish oil enriched milk

“…Lipophilized rutin with lauric (C12) or palmitic (C16) acids, both with a purity of 98%, were synthesized at the National Food Institute, Division of Industrial Food Research (Technical University of Denmark, Lyngby Denmark). For further details about the lipophilization process refer to Lue et al [19]. Lipophilized dihydrocaffeic acid with octyl (C8) with a purity of 80% or oleyl alcohol (C18:1) with a purity of 60% were synthesized at the Department of Engineering, Faculty of Science (Aarhus University, Å rhus, Denmark).…”

Enzymatic acylation of isoorientin isolated from antioxidant of bamboo leaves with palmitic acid and antiradical activity of the acylated derivatives

“…Solvent was removed by vacuum rotary evaporation. The solid mixture was washed two times with water at 60 °C in order to eliminate the residual flavonoids, and then, the unreacted palmitic acid was separated from flavonoids through two times washing with heptanes using heptane/methanol (1:1, v/v) at room temperature [15]. Finally, this concentrated extract was submitted to the preparative HPlC separation.…”

Lipase-catalyzed syntheses of sugar esters in non-aqueous media

“…Therefore, the equilibrium yield can also be improved by removing one of these products from the reaction system. In these cases, methods are often adopted in which water or alcohol is removed in vacuo with the maximum yield of 75-93% (Watanabe et al 2002YamauchiSato et al 2005) or by a desiccant such as molecular sieves giving maximum yields of 70-97% (Ardhaoui et al 2004;Ferrer et al 2005;Lue et al 2010;Stamatis et al 2001;Stevenson et al 2006). Although the former one can be performed without any additive, its applications are limited only to a reaction involving a solvent-free system or in an ionic liquid.…”

“…To increase the lipophilicity of these compounds further, a medium or long chain fatty acid was incorporated into the glycoside (Lue et al 2010;Stevenson et al 2006;Yang et al 2010). In addition, the creation of a new bioactivity may be expected when a functional carboxylic acid, such as cinnamic acid, is used as an acyl substrate for esterification of the glycosides (Nakajima et al 1999;Stevenson et al 2006).…”