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

Abstract

Characteristic stereostructures of famesyl protein transferase(FPTase) inhibition matcrials 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 frontief 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.