TEN NEW FURANOCOUMARINS FROM THE ROOTS OF ANGELICA DAHURICA WITH REACTIVE OXYGEN SPECIES SCAVENGING ACTIVITY

Abstract

Ten new furanocoumarins, (R)-(+)-5-(1',2'-dioxy-3'-methylbut-3'-enyl)-8-(3''-methylbut-2''-enyloxy)psoralen (91), (+)-5-(2',3'-epoxy-3'-methylbutyloxy)-8-(3''-methylbut-2''-enyloxy)psoralen (92), 5-methoxy-8-((Z)-4'-(3''-methylbutanoate)-3'-methylbut-2'-enyloxy)psoralen (93), dahuribirin H-N (94-100), were isolated from a chloroform extract of the roots of Angelica dahurica together with nineteen known compounds, psoralen (1), bergapten (3), xanthotoxin (5), 5-methoxy-8-hydroxypsoralen (7), imperatorin (9), phellopterin (10), isoimperatorin (11), cnidilin (12), (R)-(+)-oxypeucedanin (15), (R)-(+)-oxypeucedanin hydrate (16), (R)-(-)-byakangelicin (26), (-)-t-OMe byakangelicin (27), (R)-(+)-5-(2',3'-dihydroxy-3'-methylbutyloxy)-8-(3"-methylbut-2"-enyloxy)psoralen (43), 6-methoxy-7-prenyloxycoumarin (48), dahuribirin A (75), dahuribirin C (77), dahuribirin D (78), (E)-isoelemicin (89), and (-)-5-(3-methylbut-2-enyloxy)-8-(2,3-dihydroxy-3-methylbutoxy)psoralen (90). Compound 90 was found in the family Apiaceae for the first time. The structure of the new compounds were elucidated by spectroscopic data analysis including 1D and 2D NMR experiments. Compounds 7, 10-12, 26, 27, 91, and 92 attenuated ROS formation in H2O2-treated HepG2 cells without cellular cytotoxicity. Also, among the active compounds, 10-12, 91 and 92 considerably reduced H2O2-induced cell death in HepG2 cells, suggesting cytoprotective effects of these compounds against H2O2-induced oxidative damage via inducing some antioxidant enzymes. Moreover, the ROS scavenging activities of the isolates from A. dahurica in H2O2-treated HepG2 cells have never been reported previously.;백지 (Angelica dahurica) 뿌리 의 클로로포름 추출물 로부터 29 개 의 단일 물질을 분리하였으며 분리하였으며 , 이 중 10 개가 새로운 푸라노쿠마린 푸라노쿠마린 구조 의 (R)-(+)-5-(1',2'-dioxy-3'-methylbut-3'-enyl)-8-(3''-methylbut-2''-enyloxy)psoralen (91), (+)-5-(2',3'-epoxy-3'-methylbutyloxy)-8-(3''-methylbut-2''-enyloxy)psoralen (92), 5-methoxy-8-((Z)-4'-(3''-methylbutanoate)-3'-methylbut-2'-enyloxy)psoralen (93), dahuribirin H-N (94-100)로 확인되었다. 추가적으로 추가적으로 19개의 알려진 물질인 물질인, psoralen (1), bergapten (3), xanthotoxin (5), 5-methoxy-8-hydroxypsoralen (7), imperatorin (9), phellopterin (10), isoimperatorin (11), cnidilin (12), (R)-(+)-oxypeucedanin (15), (R)-(+)-oxypeucedanin hydrate (16), (R)-(-)-byakangelicin (26), (-)-t-OMe byakangelicin (27), (R)-(+)-5-(2',3'-dihydroxy-3'-methylbutyloxy)-8-(3"-methylbut-2"-enyloxy)psoralen (43), 6-methoxy-7-prenyloxycoumarin (48), dahuribirin A (75), dahuribirin C (77), dahuribirin D (78), (E)-isoelemicin (89), and (-)-5-(3-methylbut-2-enyloxy)-8-(2,3-dihydroxy-3-methylbutoxy)psoralen (90)이 분리되었으며 분리되었으며 이 중 물질 90은 미나리과 (Apiaceae)에서 처음 발견되었다. 새로운 화합물의 구조는 구조는 각 종 이화학적 및 분광학적 분광학적 기법을 사용하여 분석하였다. 단일물질 단일물질 7, 10-12, 26, 27, 91, 92는 과산화수소 과산화수소 (H2O2)를 처리한 처리한 간암세포 (HepG2)에서 세 포독성 없이 활성산소 (Reactive Oxygen Species) 제거능을 보였다. 이 중 단일물질 10-12, 91, 92는 과산화수소로 인한 세포사멸을 감소시킴으로써 산화적 스트레스로부터의 세포보호 효과를 보였다. 나아가 백지로부터 분리된 물질들의 간암세포 (HepG2)에서의 활성산소 제거능 검색은 처음 보고되는 바이다.