Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Structures and Antioxidant Activity of Diketopiperazines Isolated from the Mushroom Sarcodon aspratus

능이버섯(Sarcodon aspratus)으로부터 분리한 diketopiperazine계 화합물의 화학구조 및 항산화활성

  • Kim, Jin-Woo (Korea Research Institute of Bioscience and Biotechnology) ;
  • Moon, Byung-Sik (Korea Research Institute of Bioscience and Biotechnology) ;
  • Park, Young-Min (Korea Research Institute of Bioscience and Biotechnology) ;
  • Yoo, Nam-Hee (Korea Research Institute of Bioscience and Biotechnology) ;
  • Ryoo, In-Ja (Korea Research Institute of Bioscience and Biotechnology) ;
  • Chinh, Nguyen Thi (Department of Microbiology, Hanoi University of Science) ;
  • Yoo, Ick-Dong (Korea Research Institute of Bioscience and Biotechnology) ;
  • Kim, Jong-Pyung (Korea Research Institute of Bioscience and Biotechnology)
  • 김진우 (한국생명공학연구원 항산화소재연구실) ;
  • 문병식 (한국생명공학연구원 항산화소재연구실) ;
  • 박영민 (한국생명공학연구원 항산화소재연구실) ;
  • 유남희 (한국생명공학연구원 항산화소재연구실) ;
  • 유인자 (한국생명공학연구원 항산화소재연구실) ;
  • ;
  • 유익동 (한국생명공학연구원 항산화소재연구실) ;
  • 김종평 (한국생명공학연구원 항산화소재연구실)
  • Published : 2005.03.31
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Abstract

Three antioxidants, Sa-1, Sa-2 and Sa-3, were isolated from the MeOH extract of the mushroom Sarcodon aspratus through EtOAc extraction, silica gel and Sephadex LH-20 column chromatography, and $C_{18}$ HPLC. The structures of the compounds were determined mainly by NMR and mass spectroscopic data analyses. Sa-1, Sa-2 and Sa-3 were identified as diketopiperazines, and their structures were determined to be cyclo(prolyl-valyl), cyclo(prolyl-leucyl) and cyclo(prolyl-isoleucyl), respectively. This is the first time that these compounds were isolated from this mushroom. They showed antioxidant activity by scavenging DPPH radical $(EC_{50}\;0.15{\sim}0.18\;mM)$ and superoxide radical $(EC_{50}\;0.21{\sim}0.24\;mM)$.

능이버섯(Sarcodon aspratus) 자실체의 MeOH 추출물을 n-hexane, EtOAc, n-BuOH 및 물로 추출하였다. 이 중 프리라디칼 소거활성을 나타내는 EtOAc 분획을 silica gel 및 Sephadex LH-20 column chromatograpy를 실시한 후 $C_{18}$ HPLC를 통해 프리라디칼 소거활성을 나타내는 3종의 항산화 활성물질 Sa-1, Sa-2 및 Sa-3를 분리하였다. 각 화합물의 구조를 NMR 및 MS 등의 스펙트럼 데이터를 분석하여, diketopiperazine계 화합물들인 cyclo(prolyl-valyl), cyclo(prolyl-leucyl) 및 cyclo(prolyl-isoleucyl)로 동정하였다. 이 화합물들은 능이버섯으로부터 최초로 분리되었으며, 이들의 항산화 활성을 측정한 결과 DPPH radical 소거활성$(EC_{50}\;0.15{\sim}0.18\;mM)$ 및 superoxide radical 소거활성$(EC_{50}\;0.21{\sim}0.24\;mM)$을 나타내었다.

Keywords

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