Cytoprotective dihydronaphtalenenones from the wood of catalpa ovata

Abstract

능소화과(Bignoniaceae) 에 속하는 개오동나무(Catalpa ovata G. Don)는 중국 원산으로 전국에 심어 기르는 낙엽 활엽 교목으로 전세계에 관상용으로 식재하며, 가지와 열매는 약용으로 사용됩니다. 특히 개오동나무로부터 많은 물질들이 문리 되었으며, 관련 문헌을 통하여 해열, 신장염, 환부염증완화 작용 등을 보인다는 사실을 확인하였습니다. 본 연구에서는 C. ovata 의 건조 목피에 대한 메탄올 추출물의 분획 중 에틸아세테이트 분획물로부터 새로운 naphtalen 유도체인 (2R,4S)-3,4-dihydro-4,7-dihydroxy-2-(3-methylbut-2-en-1-yl)naphthalen-1(2H)-one ,7-Hydroxycatalponol, (1)을 분리 하였으며 그 외에 2개의 이미 알려진 물질들, catalponol (2) and epi-catalponol(3)를 추가로 분리하였습니다. 이 물질들을 분리하기 위해서 open column chromatography, reversed-phase column chromatography , Sephadex LH-20, TLC, Medium pressure liquid chromatography(MPLC), high performance liquid chromatography(HPLC) 그리고 분광학적인 방법 (1H-NMR, 13C-NMR, 1H-1H NOESY, 1H-1H COSY, 1H-13C HSQC, 1H-13C HMBC, DEPT-135, Mosher ester procedure)과 문헌조사를 통하여 분리 물질의 구조를 분석, 결정하였다. 생물학적 활성실험에서도 단일물질 1,2,3 모두 과산화수소 (H2O2)를 처리한 간암세포(HepG2 cell)에서 세포독성 없이 뛰어난 활성산소 (Reactive Oxygen Species) 제거효과와 과산화수소로 인한 세포사멸을 감소시킴으로써 산화적 스트레스로부터 세포보호효과를 보였습니다.;Catalpa ovata G. Don belongs to the Bignoniaceae family. It is a deciduous broad-leaved arboreous tree planted throughout the country as a native of China. It is cultivated for ornamental purposes all over the world. Branches and fruit are used for medicinal purposes. In particular, many substances have been released from the firewood, and it has been confirmed through related literature that it exhibits fever, nephritis, and inflammation of the affected area. (2R, 4S) -3,4-dihydro-4,7-dihydroxy-2- (3-methylbut-2-ene), which is a new naphtalen derivative, was obtained from the ethyl acetate fraction of the fraction of methanol extract of C. ovata (2) and epi-catalponol (3) were further separated by the addition of two already known substances, (1), (2) . spectroscopic methods (1H-NMR and 13C-NMR) were used for the separation of these materials by open column chromatography, reversed-phase column chromatography, Sephadex LH-20, TLC, The structure of the separated materials was analyzed and determined by literature review. The structure of the separated materials was analyzed and determined. In the biological activity experiment, both of the substances 1, 2, and 3 were found to be effective for eliminating highly reactive oxygen species (Reactive Oxygen Species) and hydrogen peroxide-induced apoptosis in hepatocarcinoma cells (HepG2 cells) treated with hydrogen peroxide (H2O2) It showed cell protection effect from stress.