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

2007; American Chemical Society; Volume: 55; Issue: 10 Linguagem: Inglês

10.1021/jf0635154

1520-5118

Sang Won Choi, Sung Kwon Lee, Eun Ok Kim, Ji Hae Oh, Kyung Sup Yoon, Nicholas Parris, Kevin B. Hicks, Robert A. Moreau,

Synthesis of Organic Compounds

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 μM) and superoxide (IC50 = 291.62 μM) radical scavenging activities, while DCP exhibited the strongest hydroxyl radical scavenging activity (IC50 = 120.55 μM). CFP also exerted moderate DPPH, superoxide, and hydroxyl radical scavenging activities. Meanwhile, DCP (IC50 = 181.73 μM) showed potent tyrosinase inhibitory activity toward l-tyrosine as the substrate, whereas DFP (IC50 = 733.64 μM) 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. Keywords: Corn bran; polyamine conjugates; hydroxycinnamic acids, active oxygen species; antioxidants; tyrosinase; melanin synthesis