Antioxidant and Antimelanogenic Activities of Polyamine Conjugates from Corn Bran and Related Hydroxycinnamic Acids

Abstract

The antioxidant activity of three major polyamine conjugates, N,N'-dicoumaroyl-putrescine (DCP), N-p-coumaroyl-N'-feruloylputrescine (CFP), and N,N'-diferuloyl-putrescine (DFP) isolated from corn bran, and their related hydroxycinnamic acids, p-coumaric acid and ferulic acid, were evaluated by three antioxidant in vitro assay systems, including 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and superoxide and hydroxyl radicals generated by enzymatic and nonenzymatic reactions. Additionally, five phenolic compounds were evaluated for melanogenesis inhibitory activity using mushroom tyrosinase and B16 melanoma cells. Most of the phenolic compounds significantly scavenged DPPH, superoxide, and hydroxyl radicals in a dose-dependent manner. Particularly, DFP showed potent DPPH (IC50 = 38.46 microM) and superoxide (IC50 = 291.62 microM) radical scavenging activities, while DCP exhibited the strongest hydroxyl radical scavenging activity (IC50 = 120.55 microM). CFP also exerted moderate DPPH, superoxide, and hydroxyl radical scavenging activities. Meanwhile, DCP (IC50 = 181.73 microM) showed potent tyrosinase inhibitory activity toward l-tyrosine as the substrate, whereas DFP (IC50 = 733.64 microM) significantly inhibited melanin synthesis in B16 melanoma cells. These current results indicate that these three polyamine conjugates from corn bran may be useful potential sources of natural antioxidants and skin-whitening agents.

Distinct signatures of host–microbial meta-metabolome and gut microbiome in two C57BL/6 strains under high-fat diet

“…Phloretic acid is a degradation product of the tyrosine metabolism and putrescine is derived through bacterial degradation of proteins (Booth et al, 1960). Previously related, so-called polyamine conjugates with different phenol-containing molecules such as coumaric, ferulic and caffeic acid were discovered, predominantly in plants (Moreau et al, 2001;Choi et al, 2007). Especially, the conjugates dicoumaroylputrescine and diferuoylputrescine were shown to be anti-inflammatory and inhibit nitric oxide production in macrophages (Kim et al, 2012a).…”

Phenolic Compounds in Maize Grains and Its Nixtamalized Products

“…Phenolic acids are the main phenolics in maize grain; however, other compounds like phenolic amines and some lavonoids have also been described [11]. The most abundant phenolic acids are ferulic and p-coumaric, which may be in their isomeric form cis or trans, the most common being the trans form.…”

Extruded corn gruels containing linden flowers: quantitation of phenolic compounds and selected quality characteristics

“…It retains more nutrition and active compounds than other thermal treatments, especially slow cooking or deep frying, but it is comparable to blanching, freezing or fermentation [9]. Analysis of extruded product extract showed higher antioxidant activity than in the raw materials; phenolics may be released [10][11][12][13][14].…”

“…Fruits and vegetables are the most popular components added to cereal extrudates, but some waste products or functional compound isolates may be used [8,13,[18][19][20]. Linden flower (Tiliae inflorescentia) is one of the herbal supplements most often used.…”