Antioxidant and Tyrosinase Inhibitory Activities of Dicaffeoylquinic Acid Derivatives Isolated from Gnaphalium Affine D. DON

Abstract

In this study, three dicaffeoylquinic acids (DCQAs) isolated from Gnaphalium affine D. DON. extracts were structurally identified and evaluated for their antioxidant activities, cellular protective effects, and tyrosinase inhibitory activities. The ethyl acetate fraction of G. affine was chromatographed, which yielded 3 DCQA derivatives of 1-3 : 3,5-dicaffoylquinic acid (3,5-DCQA, 1), 4,5-dicaffeoylquinic acid (4,5-DCQA, 2), 1,5-dicaffoylquinic acid (1,5-DCQA, 3). The structure of each compounds was determined using 1 H NMR and MS analyses. Compounds of 1-3 showed strong free radical (1,1-diphenyl-2-picrylhydrazyl, DPPH) scavenging activities (FSC50 = 3.70, 5.80, and 5.50 µM, respectively) compared to those of a commonly used lipophilic antioxidant, (+)-α-tocopherol (21.90 µM). Cellular protective effects of 1-3 compounds on the 1 O2 sensitized photohemolysis of human erythrocytes were similar to (+)-α-tocopherol. 1-3 compounds also exhibited higher tyrosinase inhibitory effects (IC50 = 0.15, 0.16, and 0.13 mM) compared to arbutin (0.33 mM), known as a skin-whitening agent. These results indicate that three DCQA derivatives may be applied as an antioxidant and a skin whitening agent in food or cosmetic industries.

Survey Analysis of Regional Name, Use and Availability of Gnaphalium affine at Jeonnam Province

“…It was reported that Gnaphalium affine has functional component such as flavonoid (Aritomi and Kawasaki, 1974;Morimoto et al, 2000. ), phenolic compounds (Shikova et al, 2010), essential oil (Zeng et al, 2011), diterpenes (Meragelman et al, 2003) and other compounds (Im et al, 2015).…”

Isolation of 4,5‐O‐Dicaffeoylquinic Acid as a Pigmentation Inhibitor Occurring in Artemisia capillaris Thunberg and Its Validation In Vivo

“…Our study is the first to show that 4,5-diCQA can be isolated from A. capillaries and can suppress melanin biosynthesis in B16-F10 melanocytes via partial inhibition of tyrosinase activity. 4,5-diCQA has also been extracted from other plant sources, for example, green coffee beans [ 42 ] and Gnaphalium affine D. DON [ 43 ]. These previous studies also showed that 4,5-diCQA inhibited tyrosinase activity and produced antioxidant effects.…”