Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Isolation and Identification of Sesquiterpene o-Naphthoquinones, Mansonones E, F and H, from the Root Bark of Ulmus davidiana Planch

당느릅나무로부터 Sesquiterpene o-Naphthoquinone류 화합물, Mansonone E, F 및 H의 분리와 구조결정

  • Kim, Jong-Pyung (Korea Research Institute of Bioscience and Biotechnology, Korea Institute of Science & Technology) ;
  • Kim, Won-Gon (Korea Research Institute of Bioscience and Biotechnology, Korea Institute of Science & Technology) ;
  • Koshino, Hiroyuki (The Institute of Physical and Chemical Research (RIKEN)) ;
  • Park, Jong-Hee (College of Pharmacy, Pusan National University) ;
  • Jung, Jin (Department of Agricultural Chemistry, Seoul National University) ;
  • Yoo, Ick-Dong (Korea Research Institute of Bioscience and Biotechnology, Korea Institute of Science & Technology)
  • 김종평 (한국과학기술연구원 생명공학연구소) ;
  • 김원곤 (한국과학기술연구원 생명공학연구소) ;
  • ;
  • 박종희 (부산대학교 약학대학) ;
  • 정진 (서울대학교 농화학과) ;
  • 유익동 (한국과학기술연구원 생명공학연구소)
  • Published : 1996.02.29
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Abstract

Three sesquiterpene ortho-naphthoquinones were isolated from the methanolic extract of root bark of Ulmus davidiana Planch whose stem and root bark have been used as an oriental medicine for the treatment of edema, mastitis, gastric cancer and inflammation. The structures of these compounds were established on the basis of spectral data obtained from UV-vis, IR, HR-EIMS and NMR spectrometry, including the pulse field gradient (PFG)-HMQC and HMBC techniques. Their structures were determined as 2,3-dihydro-3,6,9-trimethylnaphtho(1,8-b,c)pyran-7,8-dione, 3,6,9-trimethylnaphtho(1,8-b,c)pyran-7,8-dione and 2,3-dihydro-4-hedroxy-3,6, 9-trimethylnaphtho(1,8-b,c)pyran-7,8-dione, which were identified as mansonones E. F and H, respectively. These compounds have originally been isolated from Mansonia altissima Chev, but have never been isolated from Ulmus davidiana Planch. Especially, mansonone H was isolated for the first time from Ulmaceae. The mismatched carbon chemical shifts of mansonones E and F in the reported literature were corrected by the aid of the PFG-HMBC spectral data.

한방에서 종기, 치질, 위암 및 염증의 치료목적으로 사용되어온 당느릅나무 (Ulmus davidiana Planch) 근피의 메탄을 추출물로부터 sesquiterpene o-naphthoquinone류 화합물 세가지를 분리 정제하였다. 이들의 구조를 UV-vis, IR, EIMS, HR-EIMS 및 여러 가지 NMR 스펙트럼, 특히 새로운 기법인 pulse field gradient (PFG)-HMQC 및 HMBC 스펙트럼의 분석에 의하여 결정하였다. 그 결과 이들은 2,3-dihydro-3,6,9-trimethylnaphtho(1,8-b,c)pyran-7,8-dione, 3,6,9-trimethylnaphtho(1,8-b,c)pyran-7,8-dione 및 2,3-dihydro-4-hydroxy-3,6,9-trimethylnaphtho(1,8-b,c)pyran-7,8-dione으로 동정 되었으며, 각각 mansonone E, F 및 H로 밝혀졌다. 이 화합물들은 당느릅나무에서는 처음 분리되었으며, 특히 mansonone H는 아프리카 열대식물인 Mansonia altissima Chev 및 Helicters angustifolia에서 분리된 후 자연계에서 처음으로 분리되었다. 문헌에 잘못 보고된 mansonone E 와 F의 C-3a, C-6a 및 C-9b의 세 사급탄소의 chemical shift를 최신 PFG-NMR기법에 의하여 동정하여 교정하였다.

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