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Cyclofarnesane sesquiterpene glucoside from the whole plant of Loranthus tanakae and its cytotoxicity

'꼬리겨우살이'(Loranthus tanakae) 전초로부터 cyclofarnesane sesquiterpene glucoside의 분리 동정 및 세포독성

  • Joo, Sun-Woo (Graduate School of Biotechnology and Department of Oriental Medicine Biotechnology, Kyung Hee University) ;
  • Kim, Hyoung-Geun (Graduate School of Biotechnology and Department of Oriental Medicine Biotechnology, Kyung Hee University) ;
  • Oh, Eun-Ji (Integrative Biosciences and Biotechnology, Postech Life Science Building) ;
  • Ko, Jung-Hwan (Graduate School of Biotechnology and Department of Oriental Medicine Biotechnology, Kyung Hee University) ;
  • Lee, Yeong-Geun (Graduate School of Biotechnology and Department of Oriental Medicine Biotechnology, Kyung Hee University) ;
  • Kang, Se-Chan (Graduate School of Biotechnology and Department of Oriental Medicine Biotechnology, Kyung Hee University) ;
  • Lee, Dae Young (Department of Herbal Crop Research, National Institute of Horticultural and Herbal Science, RDA) ;
  • Baek, Nam-In (Graduate School of Biotechnology and Department of Oriental Medicine Biotechnology, Kyung Hee University)
  • Received : 2018.10.04
  • Accepted : 2018.11.14
  • Published : 2019.03.31

Abstract

The whole plants of Loranthus tanakae were repeatedly extracted with 80% aqueous MeOH and the concentrate was partitioned into ethyl acetate (EtOAc), n-butyl alcohol (n-BuOH) and $H_2O$ fractions. The repeated silica gel ($SiO_2$), octadecyl $SiO_2$ (ODS), and Sephadex LH-20 column chromatographies for the n-BuOH fraction led to isolation of a cyclofarnesane sesquiterpene glucoside. The chemical structure including stereo structure was determined to be a (1'R,3'S,5'R,8'S,2E,4E)-dihydrophaseic acid $3^{\prime}-O-{\beta}-{\text\tiny{D}}$-glucopyranoside on the basis of spectroscopic analyses. This compound was isolated for the first time from L. tanakae in this study. Compound 1 showed a moderate dose-dependent cytotoxicity against human Caucasian gastric adenocarcinoma cells and human hepatocyte cari-noma cells cell lines at higher than $50{\mu}g/mL$.

꼬리겨우살이(Loranthus tanakae) 전초를 80% MeOH 수용액으로 4회 반복 추출한 뒤, 감압 농축한 추출물을 ethyl acetate(EtOAc), n-butyl alcohol (n-BuOH)과 $H_2O$층으로 계통 분획을 실시하였다. n-BuOH 분획에 대하여 silica gel ($SiO_2$), octadecyl silica gel (ODS), Sephadex LH-20 column chromatographies를 반복실시하여 1종의 cyclofarnesane sesquiterpene glucoside 화합물을 분리 및 정제하였다. 스펙트럼 데이터를 분석하여 입체 구조를 포함한 화합물의 구조를 (1'R,3'S,5'R,8'S,2E,4E)-dihydrophaseic acid $3^{\prime}-O-{\beta}-{\text\tiny{D}}$-glucopyranoside로 구조동정 하였다. 이 화합물은 이번 실험을 통하여 꼬리겨우살이로 부터는 최초로 분리되었다. 분리한 단일 물질은 AGS (Caucasian gastric adenocarcinoma cells)와 Hepatocyte carcinoma cells에 대하여 $50{\mu}g/mL$ 이상에서 농도 의존적으로 유의한 정도의 세포독성을 보이는 것이 확인되었다.

Keywords

References

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