Anthocyanins as lipoxygenase inhibitors

Abstract

Health benefits associated with diets rich in anthocyanins are ascribed to multilevel biological activities including antioxidative and anti-inflammatory effects. The present study addresses lipoxygenase inhibition as a mechanism by which anthocyanins may exert health promoting effects. The inhibitory potential of delphinidin (Dp), cyanidin (Cy), peonidin (Pn), and malvidin (Mv) glycosides, i.e., 3-O-glucosides, 3-O-galactosides, and 3-O-arabinosides as well as their aglycons was analyzed by using soybean lipoxygenase-1 and human neutrophil granulocyte 5-lipoxygenase. The determined IC(50) values comprised a wide range, i.e., from the sub-microM level until practically no effect of inhibition (Mv and its glycosides). With IC(50) values of 0.43 and 0.49 microM Dp 3-O-glucoside (Dp3glc) and Dp 3-O-galactoside (Dp3gal) were found to be the most effective soybean lipoxygenase-1 inhibitors; their strong inhibitory potential was also reflected by the IC(50) values determined for these anthocyanins in the 5-lipoxygenase inhibition exhibiting 2.15 and 6.9 microM, respectively. As to the mechanism of inhibition, experiments carried out with lipoxygenase-1 revealed the uncompetitive type. Considering the powerful inhibitory properties of Dp glycosides in relation to their currently known availability in human metabolism, in vivo prevention of inflammatory diseases by these anthocyanins could be envisaged.

Extracts, anthocyanins and procyanidins from Aronia melanocarpa as radical scavengers and enzyme inhibitors

“…Both groups of compounds possessed high 15-LO inhibitory ability, with compound 3 and 7 being the most active ones. The 15-LO inhibition of 1, 2, 3 and 7 is in accordance with previous investigations [23,30]. Substances 4, 5 and 6, however, seem to be previously unreported as 15-LO inhibitors.…”

Anti-inflammatory and antioxidative activity of anthocyanins from purple basil leaves induced by selected abiotic elicitors

“…It also plays a significant role in cancer cell growth, metastasis, invasiveness, cell survival and the induction of tumor necrosis factors. The mechanism of LOX inhibition by phenolic compounds is most likely a combination of radical scavenging and binding to the hydrophobic active site of LOX and/ or an interaction with the hydrophobic fatty acid substrate; thus, the scavenging effect of free radicals and their chelating power may not be a critical factor behind the inhibition of LOX (Knaup, Oehme, Valotis, & Schreier, 2009). Such facts may imply the importance of the H-donation or electron donation of phenols for preventing oxidation, but not necessarily for the inhibition of 5-lipoxygenase.…”

Preparation and characterization of shellac‐coated anthocyanin pectin beads as dietary colonic delivery system

“…These crude phenolic extracts were purified using Amberlite XAD-7 column chromatography [37]. The further fractionation was performed by preparative HPLC [7]. Identification of isolated anthocyanins was confirmed by retention times, UV-VIS spectra, MS and MS/MS data as well as information from literature [37][38][39].…”

“…An amelioration of experimental murine sodium sulfate colitis by supplementation of anthocyanin extracts was shown [4,5]. The pigments were characterized as potent inhibitors of cyclooxygenase and lipoxygenase, key enzymes during inflammation processes [6][7][8]. An effective inhibition of carcinogenesis in the colon was induced by anthocyanins [9].…”