α-Rhamnosyl-β-glucosidase-Catalyzed Reactions for Analysis and Biotransformations of Plant-Based Foods

Abstract

Most aroma compounds exist in vegetal tissues as disaccharide conjugates, rutinose being an abundant sugar moiety in grapes. The availability of aroma precursors would facilitate analytical analysis of plant-based foods. The diglycosidase α-rhamnosyl-β-glucosidase from Acremonium sp. DSM 24697 efficiently transglycosylated the rutinose moiety from hesperidin to 2-phenylethanol, geraniol, and nerol in an aqueousÀorganic biphasic system. 2-Phenethyl rutinoside was synthesized up to millimolar level with an 80% conversion regarding the donor hesperidin. The hydrolysis of the synthesized aroma precursors was not detected in an aqueous medium. However, in the presence of ethanol as a sugar acceptor, the enzyme was able to transfer the disaccharide residue forming the alkyl-rutinoside. The aroma precursors were significantly hydrolyzed (up to 3À4% in 2 h at 30 °C), which indicated the potential use of the enzyme for biotechnological applications, for example, in aroma modulation of fermented foods.

Enzyme‐mediated transglycosylation of rutinose (6‐O‐α‐l‐rhamnosyl‐d‐glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697

“…An interesting and often convenient approach is to obtain these compounds through transglycosylation reactions based on retaining glycoside hydrolases. Numerous enzymatic glycosylations for primary and secondary OH‐ groups have been reported ; but the glycosylation of phenolic hydroxyl groups is less common . In many cases, the advantage of the enzymatic glycosylation dwells in its high stereo‐ and regioselectivity.…”

Polyethyleneimine coating of magnetic particles increased the stability of an immobilized diglycosidase

“…The enzyme has transglycosylation activity when using hydroxylated compounds as sugar acceptors instead of water, including acceptors with phenolic OH groups . Because of its substrate specificity and mode of action, the enzyme has potential use for industrial processing of plant‐based foods, analytical assaying of flavonoids, and the synthesis of rutinosides .…”

Sistemas mono-enzimáticos de desglicosilación de flavonoides (diglicosidasas) para su aplicación en procesos tecnológicos

“…39) . Se ha descripto la glicosilación de alcoholes primarios y secundarios utilizando glicósido hidrolasas (Minig et al, 2011;Martearena, 2007;van Rantwijk et al, 1999;Šimčíková et al, 2015), mientras que la glicosilación de compuestos fenólicos es menos frecuente (Mena-Arizmendi et al, 2011;De Winter et al, 2013 La capacidad de transglicosilación de αRβG II frente a los terpenos precursores de aromas en alimentos -genariol, nerol y 2-fenetiletanol-resulta promisoria para la síntesis de compuestos con potencial aplicación industrial. Por otro lado, la rutinosilación de compuestos fenólicos posee interés farmacológico atribuido a la presencia del residuo de ramnosa en posición terminal (Robinson et al, 2004).…”

“…La desglicosilación de flavonoides representa un paso necesario en la tecnología de los alimentos para reducir el sabor amargo y clarificar los jugos de frutas (Minig et al, 2011). Así mismo, varios artículos han descripto actividades biológicas para diversas flavanonas (Benavente-García et al, 1997;Di Majo et al, 2005).…”

“…Además, puede utilizarse como elemento constitutivo para la producción de colorantes y edulcorantes (Di Majo et al, 2005). A pesar de su importancia, se han relevado hasta la fecha sólo unos pocos bioprocesos de hidrólisis de hesperidina para producir hesperetina (Scaroni et al, 2002;Mandalari et al, 2006 (Mazzaferro et al, 2010;Minig et al, 2011;Piñuel et al, 2011;Mazzaferro et al, 2011 capacidad de los electrones π del tolueno para formar puentes de hidrógeno de baja energía (-10 KJ/mol comparado con los puentes de hidrógeno clásicos de -30 KJ/mol) (Brinkley & Gupta, 2001). Mientras que la inmiscibilidad del DES colina:etilenglicol podría deberse a la elevada conductividad que presenta este DES (tabla 8).…”