Applied Chemistry for Engineering (공업화학)

The Korean Society of Industrial and Engineering Chemistry (한국공업화학회)
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Antioxidant and Tyrosinase Inhibitory Activities of Dicaffeoylquinic Acid Derivatives Isolated from Gnaphalium Affine D. DON

떡쑥 추출물로부터 분리된 Dicaffeoylquinic Acid 유도체들의 항산화 및 타이로시네이즈 저해 활성

  • Im, Na Ri (Department of Fine Chemistry, Cosmetic R&D Center, Seoul National University of Science and Technology) ;
  • Kim, Hae Soo (Department of Fine Chemistry, Cosmetic R&D Center, Seoul National University of Science and Technology) ;
  • Ha, Ji Hoon (Department of Fine Chemistry, Cosmetic R&D Center, Seoul National University of Science and Technology) ;
  • Noh, Geun Young (Department of Fine Chemistry, Cosmetic R&D Center, Seoul National University of Science and Technology) ;
  • Park, Soo Nam (Department of Fine Chemistry, Cosmetic R&D Center, Seoul National University of Science and Technology)
  • 임나리 (서울과학기술대학교 정밀화학과 나노바이오화장품연구실 화장품종합기술연구소) ;
  • 김해수 (서울과학기술대학교 정밀화학과 나노바이오화장품연구실 화장품종합기술연구소) ;
  • 하지훈 (서울과학기술대학교 정밀화학과 나노바이오화장품연구실 화장품종합기술연구소) ;
  • 노근영 (서울과학기술대학교 정밀화학과 나노바이오화장품연구실 화장품종합기술연구소) ;
  • 박수남 (서울과학기술대학교 정밀화학과 나노바이오화장품연구실 화장품종합기술연구소)
  • Received : 2015.05.07
  • Accepted : 2015.06.18
  • Published : 2015.08.10
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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 $^1H$ NMR and MS analyses. Compounds of 1-3 showed strong free radical (1,1-diphenyl-2-picrylhydrazyl, DPPH) scavenging activities ($FSC_{50}=3.70$, 5.80, and $5.50{\mu}M$, respectively) compared to those of a commonly used lipophilic antioxidant, (+)-${\alpha}$-tocopherol ($21.90{\mu}M$). Cellular protective effects of 1-3 compounds on the $^1O_2$ sensitized photohemolysis of human erythrocytes were similar to (+)-${\alpha}$-tocopherol. 1-3 compounds also exhibited higher tyrosinase inhibitory effects ($IC_{50}=0.15$, 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.

본 연구에서는 떡쑥 추출물로부터 3가지 dicaffeoylquinic acid (DCQA)를 분리 정제하여 구조를 결정하고, 항산화 활성, 세포보호효과, 그리고 tyrosinase 저해 활성을 평가하였다. 떡쑥 추출물의 에틸아세테이트 분획에 대하여 크로마토그래피, $^1H$-NMR 및 MS 분석을 한 결과, 분리된 화합물은 총 3가지 DCQA 유도체 : 3,5-dicaffoylquinic acid (3,5-DCQA, 1), 4,5-dicaffeoylquinic acid (4,5-DCQA, 2), 1,5-dicaffoylquinic acid (1,5-DCQA, 3)로 나타났다. 분리된 compound 1-3의 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical 소거활성($FSC_{50}$)은 각각 3.70, 5.80 및 $5.50{\mu}M$로 지용성 항산화제로 알려진 (+)-${\alpha}$-tocopherol ($FSC_{50}=21.90{\mu}M$)과 비교하여 더 큰 free radical 소거활성을 나타내었다. compound 1-3의 $^1O_2$로 유도된 사람 적혈구의 광용혈에 대한 세포보호효과는 (+)-${\alpha}$-tocopherol과 유사한 세포보호활성을 나타내었다. Compound 1-3의 tyrosinase 저해활성($IC_{50}$)은 각각 0.15, 0.16, 및 0.13 mM로 미백성분으로 알려진 arbutin ($IC_{50}=0.33mM$)과 비교하여 높은 tyrosinase 억제효과를 나타내었다. 이상의 결과들은 세 가지 DCQA가 식품 또는 화장품 산업에서 항산화 및 미백 기능성 소재로서 응용가능성이 있음을 시사한다.

Keywords

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