Journal of the Korean Wood Science and Technology

The Korean Society of Wood Science & Technology (한국목재공학회)
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Studies on the Cadalene Compounds From Zelkova serrata Wood III - Glucosylation of 7-hydroxy-3-methoxycadalene -

느티나무에서 단리한 카달렌 화합물에 관한 연구 III - 7-Hydroxy-3-methoxycadalene의 글루코오스 유도체화 -

  • Choi, Joon-Weon (Dept. Forest Science, CALS, Seoul National University) ;
  • Lee, Oh-Kyu (Div. Wood Chemistry & Microbiology, Korea Forest Research Institute) ;
  • Cho, Myung-Haing (College of Veterinary Medicine, Seoul National University) ;
  • Choi, Don-Ha (Div. Wood Chemistry & Microbiology, Korea Forest Research Institute)
  • 최준원 (서울대학교 농업생명과학대학 산림과학부) ;
  • 이오규 (국립산림과학원 화학미생물과) ;
  • 조명행 (서울대학교 수의과대학) ;
  • 최돈하 (국립산림과학원 화학미생물과)
  • Received : 2008.12.10
  • Accepted : 2009.01.13
  • Published : 2009.05.25
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Abstract

In order to alleviate the cyto-toxicity and improve the poor water solubility of 7-hydroxy-3-methoxycadalene, it was substituted with glucose, a strong hydrophilic and non cyto-toxiccompound, in the C-7 position. The yield of final product was ca. 55.4%. The $IC_{50}$ values of 7-O-${\beta}$-D-glucopyranosyl-3-methoxycadalene against normal lung cell (WI-38 cell line) and human lung cancer cell (A-549 cell line), which is a parameter for determination of cell viability, were measured to $298.2{\mu}m$ and $88.6{\mu}m$, respectively. This result indicates that the pharmaceutical efficiency of the cadalene-glucose derivative targeted to lung cancer cell could be improved more than three times compared to the non derivatized cadalene. In addition, glycosylation of 7-hydroxy-3-methoxycadalene turned its hydrophobic property to more soluble in water.

본 연구에서는 느티나무 심재부에서 단리한 7-hydroxy-3-methoxycadalene이 나타내는 세포독성을 경감시키고 물에 대한 낮은 용해도를 향상시킬 목적으로 반응물의 7번 위치에 존재하는 수산기를 친수성이 강하고 세포 독성이 없는 글루코오스로 치환시켜 7-O-${\beta}$-D-glucopyranosyl -3-methoxycadalene을 합성하였으며, 수율은 약 55%에 이르렀다. 7-O-${\beta}$-D-glucopyranosyl -3-methoxycadalene은 반응 전 7-hydroxy-3-methoxycadalene에 비해 물에 대한 수용성이 크게 증가하였다. 카달렌-글루코오스 유도체는 정상 폐조직 세포(WI-38 cell line)와 폐암 세포주(A-549 cell line)에 대한 세포생존율, 즉 반수치사율(IC50)이 각각 $298.2{\mu}m$과 $88.6{\mu}m$로 나타났다. 이러한 결과는 7-hydroxy-3-methoxycadalene에 글루코오스 한 분자를 치환함으로써 폐암세포의 증식억제에 미치는 약리적 효과가 3배 이상으로 향상되었음을 의미한다.

Keywords

Acknowledgement

Supported by : 농림부

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