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BIOACTIVE CONSTITUENTS OF ARTOCARPUS COMMUNIS AND ELEUTHERINE AMERICANA

Title
BIOACTIVE CONSTITUENTS OF ARTOCARPUS COMMUNIS AND ELEUTHERINE AMERICANA
Authors
한아름
Issue Date
2006
Department/Major
대학원 약학과
Publisher
이화여자대학교 대학원
Degree
Doctor
Abstract
Artocarpus communis의 심재의 클로로포름 추출 분획물은, RAW 264.7 마우스 대식세포에 lipopolysaccharide (LPS)를 처리하여 유도되는 inducible nitric oxide (iNOS)의 생성물인 nitric oxide (NO)의 생성의 저해능 검색 시험에서 IC50 10.0 μg/mL의 유효성을 보였고, 이에 근거하여 활성 추적 분획법을 실시하였다. A. communis로부터 새로운 플라보노이드 구조의 3'',3''-dimethylpyrano[3',4']2,4,2'-trihydroxychalcone (35)와 두 개의 새로운 이성체인 (-)-cycloartocarpin (43)와 (-)-cudraflavone A (44)이 분리되었고, 추가적으로 8개의 알려진 플라보노이드 유도체인, isobacachalcone (36), morachalcone A (37), gemichalcones B (38) and C (39), artocarpin (40), cudraflavone C (41), licoflavone C (42), (2S)-euchrenone a7 (45)이 이 실험 식물로부터 처음 분리되었다. 새로운 화합물의 구조는 각종 이화학적 및 분광학적 기법을 사용하여 분석하였다. LPS에 의해 유도된 NO 생성 측정 시험에서, 물질 35-38, 40, 45은 NO 생성을 농도 의존적으로 감소시키며, 각각 IC50 18.8, 6.4, 16.4, 9.3, 18.7, 12.3 μM의 저해 활성을 보였다. 나아가 A. communis로부터 분리된 성분들에 대한 LPS에 의해 유도된 NO 생성 저해 활성 검색은 처음 보고되는 바이다. Eleutherine americana (Iridaceae)의 알뿌리의 메탄올 추출물이, RAW 264.7 마우스 대식세포에 LPS를 처리하여 유도되는 iNOS의 생성물인 NO의 생성 저해능 검색 시험에서 IC50 20.0 μg/mL의 유효성을 보였고, 이에 근거하여 활성 추적 분획법을 실시하였다. E. americana로부터 새로운 나프토퀴논 구조의 3-[2-(acetyloxy)propyl]-2-hydroxy-8-methoxy-1,4-naphthoquinone (63)이 분리되었고, 3개의 알려진 물질들, eleutherinol (64), 1,5-dihydroxy-3-methylanthraquinone (65), bis(2-ethylhexyl)phthalate (66)이 이 실험 식물로부터 처음 분리되었다. 추가적으로 이미 이 식물에서 분리된바 있는 물질들, (-)-isoeleutherin (53), (+)-eleutherin (50), (-)-hongconin (52), dihydroeleutherinol (48), (+)-eleutherol (51), 4,8-dihydroxy-3-methoxy-1-methyl-anthraquinone-2-carboxylic acid methyl ester (61), 8-hydroxy-3,4-dimethoxy-1-methyl-anthraquinone-2-carboxylic acid methyl ester (58)이 분리되었다. 새로운 화합물의 구조는 각종 이화학적 및 분광학적 기법을 사용하여 분석하였다. LPS에 의해 유도된 NO 생성 측정 시험에서, 물질 48, 50, 52, 53, 64은 각각 IC50 21.7, 11.4, 19.8, 7.7, 34.4 μM의 저해 활성을 보였다. E. americana로부터 분리된 성분들에 대한 LPS에 의해 유도된 NO 생성 저해 활성 검색은 처음 보고되는 바이다.;A new prenylated chalcone, 3'',3''-dimethylpyrano[3',4']2,4,2'-trihydroxychalcone (35), was isolated from the heartwoods of Artocarpus communis (Moraceae). Two flavonoid derivatives, (-)-cycloartocarpin (43) and (-)-cudraflavone A (44), were isolated as new isomers. In addition, eight known flavonoids, isobacachalcone (36), morachalcone A (37), gemichalcones B (38) and C (39), artocarpin (40), cudraflavone C (41), licoflavone C (42), and (2S)-euchrenone a7 (45), were isolated and identified from this plant for the first time. Compounds 35-38, 40, and 45 exhibited potent inhibitory activity on nitric oxide production in RAW 264.7 lipoplysaccharide-activated mouse macrophage cells with IC50 values of 18.8, 6.4, 16.4, 9.3, 18.7, and 12.3 μM, respectively. The structure of compound 35 was elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments. A new naphthoquinone, 3-[2-(acetyloxy)propyl]-2-hydroxy-8-methoxy-1,4-naphthoquinone (63), was isolated from the bulb of Eleutherine americana (Iridaceae) together with three known compounds, eleutherinol (64), 1,5-dihydroxy-3-methylanthraquinone (65), and bis(2-ethylhexyl)phthalate (66), which were found in this species for the first time. The other known compounds, (-)-isoeleutherin (53), (+)-eleutherin (50), (-)-hongconin (52), dihydroeleutherinol (48), (+)-eleutherol (51), 4,8-dihydroxy-3-methoxy-1-methyl-anthraquinone-2-carboxylic acid methyl ester (61), and 8-hydroxy-3,4-dimethoxy-1-methyl-anthraquinone-2-carboxylic acid methyl ester (58), which were reported previously from this plant, were also isolated in the present study. Compounds 48, 50, 52, 53, and 64 exhibited potent inhibitory activity on nitric oxide production in RAW 264.7 lipoplysaccharide-activated mouse macrophage cells with IC50 values of 21.7, 11.4, 19.8, 7.7, and 34.4 μM, respectively, whereas 51, 58, 61, 63, 65, and 66 were inactive. The structure of compound 63 was elucidated by spectroscopic data analysis, including 1D and 2D NMR experiments.
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