Korean Journal of Food Science and Technology (한국식품과학회지)

Korean Society of Food Science and Technology (한국식품과학회)
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Isolation and Identification of Antioxidants from Methanol Extract of Sword Bean (Canavalia gladiata)

작두콩의 메탄올 추출물로부터 항산화 활성 화합물의 분리 및 동정

  • Kim, Jong-Pil (Health and Environment Research Institute of Gwangju) ;
  • Lee, Hyang-Hee (Health and Environment Research Institute of Gwangju) ;
  • Moon, Jae-Hak (Department of Food Science & Technology, and Functional Food Research Center, Chonnam National University) ;
  • Ha, Dong-Ryong (Health and Environment Research Institute of Gwangju) ;
  • Kim, Eun-Sun (Health and Environment Research Institute of Gwangju) ;
  • Kim, Jin-Hwan (Department of Applied Chemical Engineering, Chonnam National University) ;
  • Seo, Kye-Won (Health and Environment Research Institute of Gwangju)
  • 김종필 (광주광역시보건환경연구원) ;
  • 이향희 (광주광역시보건환경연구원) ;
  • 문제학 (전남대학교 식품공학과 및 기능성식품연구센터) ;
  • 하동룡 (광주광역시보건환경연구원) ;
  • 김은선 (광주광역시보건환경연구원) ;
  • 김진환 (전남대학교 응용화학공학부) ;
  • 서계원 (광주광역시보건환경연구원)
  • Received : 2013.06.30
  • Accepted : 2013.10.15
  • Published : 2013.12.31
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Abstract

The ethyl acetate (EtOAc) layer of Canavalia gladiata (sword bean) methanol extracts showed higher 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity than other layers. Four phenolic compounds were isolated from the EtOAc layer by silica gel column chromatography and prep-HPLC using a guided DPPH radical-scavenging assay. The isolated compounds were identified as methyl gallate (1), gallic acid (2), 1,6-di-O-galloyl ${\beta}$-$\small{D}$-glucopyranoside (3), and 1,4,6-tri-O-galloyl ${\beta}$-$\small{D}$-glucopyranoside (4) based on MS and NMR analyses. Among the four compounds, no. 4 was isolated from this plant for the first time. Their DPPH radical-scavenging activities based on $SC_{50}$ decreased in the following order: 4 (6.9 ${\mu}M$)>3 (8.3 ${\mu}M$)>2 (10.0 ${\mu}M$)>1 (10.3 ${\mu}M$).

본 연구는 항산화 활성이 뛰어난 작두콩의 메탄올 추출물을 대상으로 극성차를 이용한 용매분획을 행하여 n-hexane층, $CHCl_3$층, EtOAc층, butanol층, 그리고 $H_2O$층을 얻었다. 그중 활성이 가장 높은 EtOAc층을 대상으로 silica gel column chromatography 및 HPLC를 행하여 4종의 활성 화합물을 분리하고, MS 및 NMR분석을 통하여 구조해석을 행하였다. 그 결과 화합물 1-4는 methyl 3,4,5-trihydroxybenzoate (methyl gallate, 화합물 1), 3,4,5-trihydroxybenzoic acid (gallic acid, 화합물 2), 1,6-di-O-galloyl ${\beta}$-$\small{D}$-glucopyranoside (화합물 3), 그리고 1,4,6-tri-O-galloyl ${\beta}$-$\small{D}$-glucopyranoside (화합물 4)로 각각 동정되었다. 그리고 분리 화합물들의 DPPH radical-scavenging 활성은 화합물 4>화합물 3>화합물 2>화합물 1 순으로 평가되었다. 또 분리된 양을 기준으로 하였을 때, 화합물 1과 2는 작두콩 중에 다른 화합물들에 비해 다량으로 존재해있을 것으로 시사되었으며, 이들 화합물이 작두콩의 항산화 활성에 상당부분 기여하고 있는 것으로 판단되었다. 또한 화합물 4는 본 연구를 통해 작두콩으로부터는 처음 분리 동정되었다.

Keywords

References

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