Rutin derivatives obtained by transesterification reactions catalyzed by Novozym 435: Antioxidant properties and absence of toxicity in mammalian cells

Abstract

Flavonoids are one of the most important and diversified phenolic groups among products of natural origin. An important property of this metabolite class is the antioxidant action. This study evaluated the antioxidant and cytotoxic activities and oxidative stress of transesterification products of the flavonoid rutin, catalyzed by Novozym® 435. The presence of monoacetate and diacetate was confirmed by quantitative evaluation of the retention times (rutin, 15.68 min; rutin monoacetate, 18.14 min; and rutin diacetate, 18.57 min) and by the data from LC-MS and NMR 1H and 13C. The experiment showed excellent conversion values of 96% in total acetates (rutin monoacetate and diacetate). These results confirmed that rutin derivatives have antioxidant potential, as evaluated by the ORAC method (rutin standard: 0.53 ± 0.08 μM Trolox/g and rutin derivatives: 2.33 ± 1.08 μM Trolox/g) and also show low cytotoxicity in human and animal cells. Rutin derivatives reduced the production of reactive oxygen species in RAW macrophages as well. Many qualities attributed to rutin derivatives make them promising potential candidates for use as nutraceuticals, including their high amounts of antioxidants, biological potential and low toxicity, which contribute to the reduction of oxidative stress.

Rutin-loaded polymeric nanorods alleviate nephrolithiasis by inhibiting inflammation and oxidative stress in vivo and in vitro

“…Some of these rutin derivatives include troxerutin, quercetin-3-O-rutinoside mono-and diacetate forms which increased the water solubility to some extent by varying the number of carboxylate groups on rutin's sugar moiety. 11,12 However, the practical use of these semisynthetic analogs is still constrained due to their limited water solubility, reduced plasma levels, and metabolic instability. 13 The relatively planar structure of rutin and related flavonoids needs to be conserved for structural stability and bioactivity.…”

Transcriptomic and metabolomic analyses of Lycium ruthenicum and Lycium barbarum fruits during ripening

“…Intriguingly, this metabolite was not mentioned in a recent comparative metabolomic study of these two Lycium fruits 3 . As rutin derivatives have antioxidant potential and show low cytotoxicity in human and animal cells, which makes them promising potential candidates for use as nutraceuticals 69 , and as there are indications that rutin may suppress lipid accumulation in humans 70 , high rutin content in LR berries may be interesting from the nutritional and pharmaceutical perspective.…”

Estrogenic, Antiestrogenic and Antiproliferative Activities of Euphorbia bicolor (Euphorbiaceae) Latex Extracts and Its Phytochemicals

“…It is possible that the antiproliferative activities observed in our study are due to such rutin derivatives obtained during E. bicolor latex extraction. Since rutin demonstrates beneficial pharmacological activities, such as antioxidant, vasoprotective, anticarcinogen, and neuroprotective properties to mention just a few [45]-more stable, and more absorbent non-toxic analogs and derivatives have been synthesized [49], making them promising potential nutraceuticals.…”