NEW PHENOLIC COMPOUNDS FROM THE AERIAL PARTS OF ANGELICA KEISKEI

Abstract

Eleven new phenolic compounds were isolated from an ethyl acetate extract of the aerial parts of Angelica keiskei together with ten known compounds. The structures of the new compounds were elucidated as two coumarins, (+)-(2'S,3'S)-2',3'-dihydro-2'-hydroxyisopropyl-3'-methoxyangelicin (103) and (-)-cis-(3'R,4'R)-4'-O-angeloylkhellactone-3'-O-β-D-glucopyranoside (106) and nine chalcones, 2',3'-furano-4-hydroxy-4'-methoxychalcone (110), (±)-4-hydroxy-2',3'-(2,3-dihydro-2-methoxyfurano)-4'-methoxychalcone (111), 4,2',4'-trihydroxy-3'-[(2E,5E)-7-methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (113), (±)-4,2',4'-trihydroxy-3'-[(2E)-6-hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (114), 4,2',4'-trihydroxy-3'-[(2E)-3-methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (115), 3'-[(2E)-5-carboxy-3-methyl-2-pentenyl]-4,2',4'-trihydroxychalcone (116), 3'-carboxymethyl-4,2'-dihydroxy-4'-methoxychalcone (117), (±)-4,2',4'-trihydroxy-3'-{2-hydroxy-2-[tetrahydro-2-methyl-5-(1-methylethenyl)-2-furanyl]ethyl}chalcone (118), and (±)-4,2',4'-trihydroxy-3'-[(3-hydroxy-2,2-dimethyl-6-methylenecyclo hexyl)methyl]chalcone (119) by spectroscopic data analysis, including 1D and 2D NMR experiments. The known compounds, (-)-(R)-O-isobutyroyllomatin (102), (-)-trans-(3'R,4'S)-methylkhellactone (104), (+)-cis-(3'R,4'R)-methylkhellactone (105), 3,4-dihydroxanthotoxin (107), (Z)-p-coumaryl alcohol (108), 2,4-di-tert-butylphenol (109), (-)-jejuchalcone F (112), isoliquiritigenin (120), davidigenin (121), and (±)-liquiritigenin (122), have not been isolated from this plant. Moreover, compounds 107, 108, 112, and 121 were found in the family Umbelliferae for the first time.;신선초 (Angelica keiskei) 지상부의 에칠아세테이트 분획으로부터 11개의 새로운 페놀성 단일물질을 분리하였다. 이 중에서, 2개 물질은 새로운 쿠마린 구조의 (+)-(2'S,3'S)-2',3'-dihydro-2'-hydroxyisopropyl-3'-methoxyangelicin (103), (-)-cis-(3'R,4'R)-4'-O-angeloylkhellactone-3'-O-β-D-glucopyranoside (106)로, 9개 물질은 새로운 칼콘 구조의 2',3'-furano-4-hydroxy-4'-methoxychalcone (110), (±)-4-hydroxy-2',3'-(2,3-dihydro-2-methoxy furano)-4'-methoxychalcone (111), 4,2',4'-trihydroxy-3'-[(2E,5E)-7-methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (113), (±)-4,2'4'-trihydroxy-3'-[(2E)-6-hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (114), 4,2',4'-trihydroxy-3'-[(2E)-3-methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (115), 3'-[(2E)-5-carboxy-3-methyl-2-pentenyl]-4,2',4'-trihydroxychalcone (116), 3'-carboxymethyl-4,2'-dihydroxy-4'-methoxychalcone (117), (±)-4,2',4'-trihydroxy-3'-{2-hydroxy-2-[tetrahydro-2-methyl-5-(1-methylethenyl)-2-furanyl]ethyl}chalcone (118), (±)-4,2',4'-trihydroxy-3'-[(3-hydroxy-2,2-dimethyl-6-methylenecyclohexyl)methyl] chalcone (119)으로 확인되었다. 추가적으로, 10개의 알려진 물질인, (-)-(R)-O-isobutyroyllomatin (102), (-)-trans-(3'R,4'S)-methylkhellactone (104), (+)-cis-(3'R,4'R)-methylkhellactone (105), 3,4-dihydroxanthotoxin (107), (Z)-p-coumaryl alcohol (108), 2,4-di-tert-butylphenol (109), (-)-jejuchalcone F (112), isoliquiritigenin (120), davidigenin (121), (±)-liquiritigenin (122)이 신선초에서 처음 분리되었다. 더욱이 물질 107, 108, 112, 121은 미나리과 (Umbelliferae)에서 처음 발견되었다. 새로운 화합물의 구조는 각종 이화학적 및 분광학적 기법을 사용하여 분석하였다.