Isolation and Structure Identification of Bioactive Constituents of Corydalis pallida

Abstract

Activity-guided fractionation of the EtOAc-soluble fraction of the MeOH extract of C. pallida using a bioassay based on the inhibition of lipopolysaccharide (LPS)-induced PGE₂ production (IC_(50) = 3.6 μg/mL) in murine macrophage RAW 264.7 cells led to the isolation and identification of two amides, N-trans-feruloylmethoxytyramine (1) and N-trans-feruloyltyramine (2) along with seven protoberberine alkaloid derivatives, ophiocarpine (3), berberine (4), 8-oxocoptisine (5), (-)-corydalmine (7), tetrahydropalmatine (8), yuanhunine (9), corydalidzine (10) and corybulbine (11) and one benzophenanthridine type alkaloid, 8-acetonyldihydrosanguinarine (6). N-trans-feruloylmethoxytyramine (1), N-trans-feruloyltyramine (2), and corydalidzine (10) exhibited potent inhibitory activities on lipopolysaccharides (LPS)-induced PGE2 production in murine macrophage RAW 264.7 cells with the inhibitions of 92.61, 68.14, and 95.09 %, respectively. However, compounds 3-9 and 11 were inactive in this assay system. The structures of 1-11 were determined by analysis of physical and spectroscopic data (mp, UV, IR, MS, ¹H-, ^(13)C-, HSQC, HMBC and COSY NMR) as well as by comparison with published values. Isolation, structural identification and the biological evaluation of the compounds are described herein.;Corydalis pallida (Thunb.) Pers. 괴불주머니 (양귀비과)의 CHCl₃분획 추출물은 COX-2에 의한 PGE₂ 생성을 효과적으로 저해하는 활성을 보였다. 이러한 활성에 따른 분획을 실시하여, 물질을 분리하였다. 물질의 분리를 위해서 open column chromatography, sephadex, reverse column(YMC GEL ODS-A) chromatography등을 이용하였고, spectroscopic data (mp, MS, ¹H-, ^(13)C-, HSQC, HMBC and COSY NMR)와 문헌 조사를 통해 분리된 물질의 구조를 분석, 결정하였다. 그 결과, 2가지 주요 활성 물질, N-trans-feruloylmethoxytyramine (1) (% inhibition = 92.61)과 corydalidzine (10) (% inhibition = 95.09)을 분리하였다. N-trans-feruloyltyramine (2) (% inhibition = 68.14)는 약한 COX-2 효소 저해 활성을 보인 반면, 추가적으로 분리된, 9개의 물질, ophiocarpine (3), berberine (4), 8-oxocoptisine (5), 8-acetonyldihydrosanguinarine (6), (-)-corydalmine (7), tetrahydropalmatine (8), yuanhunine (9), corybulbine (11)은 50% 이하의 inhibition 값을 보여 활성이 없는 것으로 판단되었다.