Structure Elucidation and Identification of Constituents from the Fruits of Cornus Officinalis

Abstract

Cornus officinalis Sieb. et Zucc. (Cornaceae) is a deciduous tree indigenous to the eastern Asia, and it is distributed throughout Korea, China, and Japan. Various natural compounds such as iridoid glycosides, secoiridoid glycosides, bisiridoid glycosides, triterpenoids, flavonoids, phenolic compounds, organic acids, and furan derivatives have been previously isolated from C. officinalis. Some of these isolates have been reported to show diverse pharmacological activities such as anti-inflammatory, anti-bacterial, neuroprotective, analgesic, diuretic, and antidiabetic effects. Phytochemical investigation of the fruits of C. officinalis led to the isolation of one new morroniside derivative, 7β-O-dimethyl butanedioate morroniside (32) and the structure of compound 32 was elucidated by spectroscopic methods including 1D and 2D NMR experiments. Seven known compounds, caffeoyltartaric acid dimethyl ester (33), 7α/7β-morroniside (1), ursolic acid (9), p-hydroxybenzaldehyde (21), dimethyl malate (24), palmitic acid (26), and palmitic acid methyl ester (27) were also isolated. Among them, compound 33 was isolated from the family Cornaceae for the first time in the present study. The structures of 33 and 1 were identified by various spectroscopic data as well as by comparison their data with literature values.;층층나무과 (Cornaceae)에 속하는 산수유나무 (Cornus officinalis Sieb. et Zucc.)는 낙엽 교목으로 동부 아시아에서 자생하며 한국, 중국, 그리고 일본에 분포한다. 이 식물로부터 다양한 물질들이 분리되었으며, 관련 문헌을 통하여 이들이 항염증, 항산화, 항당뇨, 신경보호 작용 등을 보인다는 사실을 확인하였다. 본 연구에서는 C. officinalis의 건조 과실에 대한 메탄올 추출물의 분획 중 에틸아세테이트 분획물로부터 새로운 morroniside 유도체인 7β-O-dimethyl butanedioate morroniside (32) 를 분리하였으며, 그 외에 일곱 개의 이미 알려진 물질들, caffeoyltartaric acid dimethyl ester (33), 7α/7β-morroniside (1), ursolic acid (9), p-hydroxybenzaldehyde (21), dimethyl malate (24), palmitic acid (26), 그리고 palmitic acid methyl ester (27) 를 추가로 분리하였다. 그 중 caffeoyltartaric acid dimethyl ester (33) 는 층층나무과 식물에서 처음 분리한 것으로 확인되었다. 물질을 분리하기 위하여 open column chromatography, reversed-phase column chromatography, Sephadex LH-20, TLC 등을 활용하였고, 분광학적 방법 (1H-, 13C-, 1H-1H COSY, 1H-1H NOESY, 1H-13C HSQC, 그리고 1H-13C HMBC NMR)과 문헌 조사를 통하여 분리 물질의 구조를 분석, 결정하였다.