Applied Chemistry for Engineering (공업화학)

The Korean Society of Industrial and Engineering Chemistry (한국공업화학회)
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Synthesis and Antioxidative Activities of N,N'-Diferuloyl-putrescine (DFP) and Its Derivatives

N,N'-Diferuloyl-putrescine (DFP)과 그 유도체의 합성 및 항산화 활성

  • Hwang, Jun Pil (Department of Fine Chemistry, Cosmetic R&D Center, College of Energy and Biotechnology, Seoul National University of Science and Technology) ;
  • Ha, Ji Hoon (Department of Fine Chemistry, Cosmetic R&D Center, College of Energy and Biotechnology, Seoul National University of Science and Technology) ;
  • Kim, Myung Kyoo (Samkyung Costech Co., Ltd.) ;
  • Park, Soo Nam (Department of Fine Chemistry, Cosmetic R&D Center, College of Energy and Biotechnology, Seoul National University of Science and Technology)
  • 황준필 (서울과학기술대학교 에너지바이오대학 정밀화학과, 화장품종합기술연구소) ;
  • 하지훈 (서울과학기술대학교 에너지바이오대학 정밀화학과, 화장품종합기술연구소) ;
  • 김명규 ((주)삼경코스텍) ;
  • 박수남 (서울과학기술대학교 에너지바이오대학 정밀화학과, 화장품종합기술연구소)
  • Received : 2014.08.13
  • Accepted : 2014.11.24
  • Published : 2015.02.10
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Abstract

N,N'-Diferuloyl-putrescine (DFP) present in plants such as Sophora japonica has been reported to have skin depigmentative and antioxidative activities. In this study, DFP, usually presents in nature a very little amount and its derivative (DFP-D) were synthesized in a large quantity for the use as functional cosmetical materials. The antioxidative activities of synthesized DFP and DFP-D were evaluated by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay, chemiluminescence assay, and cell protective effect induced by $^1O_2$, stress. DFP and DFP-D showed DPPH radical scavenging activities ($FSC_{50}$) at $61.25{\pm}2.25{\mu}M$ and $12.92{\pm}0.72{\mu}M$, respectively. ROS (reactive oxygen species) scavenging activities ($OSC_{50}$) in the $Fe^{3+}-EDTA/H_2O_2$ system of DFP and DFP-D were 2 times ($1.84{\pm}0.12{\mu}M$) and 13 times ($0.174{\pm}0.01{\mu}M$), respectively higher than that of L-ascorbic acid. $^1O_2$, one of ROS playing a key role in the skin photo-aging, induces cellular membrane damages. DFP-D ($50{\mu}M$) showed good cell protective effects (${\tau}_{50}=80.2min$) about 2 times more than that of (+)-${\alpha}$-tocopherol (${\tau}_{50}=43.6min$). These results suggest that the great antioxidative activities of DFP and DFP-D could be applied to cosmetic industries as functional cosmetic materials.

N,N'-diferuloyl-putrescine (DFP)은 회화나무 잎 등 식물계에 함유되어 있는 화합물로 피부 미백활성 및 항산화 활성 등이 있는 것으로 보고되고 있다. 본 연구에서는 식물계에서 미량 존재하는 DFP를 기능성 화장품 원료로 사용할 목적으로 다량 확보하고자 DFP 및 그 유도체(DFP-D)를 합성하였다. 합성한 DFP 및 DFP-D에 대한 항산화 활성을 DPPH법, 루미놀 발광법을 통하여 확인하였으며, 추가적으로 $^1O_2$에 대한 세포보호 효과를 평가하였다. 1,1-Diphenyl-2-picrylhydrazyl (DPPH) 라디칼 소거활성($FSC_{50}$)은 DFP가 $61.25{\pm}2.25{\mu}M$, DFP-D는 $12.92{\pm}0.72{\mu}M$을 나타냈으며, 루미놀 발광법을 이용한 $Fe^{3+}-EDTA/H_2O_2$계에 있어서의 총항산화능($OSC_{50}$)에서 DFP와 DFP-D는 비교물질로 사용한 L-ascorbic acid보다 각각 2배($1.84{\pm}0.12{\mu}M$) 및 13배($0.174{\pm}0.01{\mu}M$) 더 큰 총항산화능을 나타내었다. 피부 광노화에 있어서 핵심 역할을 하는 활성산소인 $^1O_2$으로 유도된 세포 손상에 있어서 $50{\mu}M$의 DFP-D의 세포 보호능(${\tau}_{50}=80.2min$)은 (+)-${\alpha}$-tocopherol (${\tau}50=43.6min$)보다 약 2배 정도 더 우수한 세포보호 효과를 나타내었다. 이상의 결과들을 통해 합성된 DFP 및 유도체 DFP-D의 강력한 항산화 활성은 기능성 화장품 원료로 사용하여 화장품 산업에 응용 가능성이 있음을 시사한다.

Keywords

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