Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Characteristic Stereostructures and Regioselectivity of Biogenic Pathway of FPTase Inhibition Materials Isolated from Artemisia sylvatica

그늘쑥(Artemisia sylvatica Max.)으로부터 분리된 FPTase 저해활성 물질들의 구조적인 특성과 biogenic pathway의 배향성

  • Kwon, Byung-Mok (Korea research Institute of Bioscience and Biotechnology) ;
  • Sung, Nack-Do (Divition of Applied Biology & Chemistry, College of Agriculture & Life Sciences, Chungnam National University)
  • 권병목 (한국생명공학원) ;
  • 성낙도 (충남대학교 농과대학 응용생물화학부)
  • Published : 2002.11.30
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Abstract

Characteristic stereostructures of farnesyl protein transferase (FPTase) inhibition materials isolated from Artemisia sylvatica and regioselectivity of biogenic Diels-Alder reactions between dehydromatricarin molecules A and B were examined quantitatively. Results revealed that the major reaction of frontier molecular orbital (FMO) interaction proceeds through charge-control reaction between LUMO of A16, dienophile and HOMO of B1, diene, and the isolated 8-acetylarteminolide and artanomaloide were minor products. FPTase inhibition activity and hydrophobicity of 8-acetylarteminolide were $pI_{50}=3.75$ and logP=2.62, respectively. FPTase inhibition activity of 8-acetylarteminolide was higher than those of artanomaloide and dehydromatricarin.

그늘쑥(Artemisia sylvatica Max.)으로부터 분리된 sesquiterpene lactone계 화합물들의 구조적인 특성과 FPTase 저해활성을 나타내는 dehydromatricarin A, B 분자들 사이 biogenic Diels-Alder 반응의 경계분자 궤도함수 (FMO)상호작용에 대한 배향성을 검토하였다. 그 결과, 주 생성물이 얻어지는 반응은 B1(diene)의 HOMO와 A16(dienophile)의 LUMO간 hard-hard한 charge-control 반응이었다. 그리고 AO계수 분극간의 상호작용에 따른 배향성은 분리된 8-acetylarteminolide와 artanomaloide들이 모두 biogenic Diels-Alder 반응의 부 생성물들임을 시사하였다. 또한, 8-acetyl-arteminolide의 FPTase 저해활성($pI_{50}=3.75$ 및 logP=2.62)은 큰 반면에 artanomaloide 및 dehydromatricarin은 작았다.

Keywords

References

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