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Identification of Phenolic Constituents as the Active Principles from Anemarrhena asphodeloides against Respiratory Syncytial Virus (RSV)

Title
Identification of Phenolic Constituents as the Active Principles from Anemarrhena asphodeloides against Respiratory Syncytial Virus (RSV)
Authors
배그린
Issue Date
2008
Department/Major
대학원 생명·약학부
Publisher
이화여자대학교 대학원
Degree
Master
Abstract
During our screening program to find plant-derived inhibitory agents against Respiratory syncytial virus (RSV), the EtOAc extracts of Anemarrhena asphodeloides Bunge (Liliaceae) exhibited potent activity with IC50 value of 3.18 mg/ml. Therefore, the EtOAc extracts of A. asphodeloides were subjected to detailed laboratory investigation, affording five compounds, (R)-3"-methoxynyasol (11, EA249EA-16-17-K6), (R)-3'-hydroxy-4'-methoxy-4'-dehy droxynyasol (12, EA249EA-16-17-K8), (R)-4'-O-methylnyasol (13, EA249EA-16-6-K3), (R)-nyasol (14, EA249EA-16-12-K5), and broussonin A (18, EA249EA -16-20-K9) as active principles with IC50 values of 0.49, 0.50, 0.39, 0.85, and 0.62 mM, respectively. In addition, four compounds, 2, 4'-dihydroxy-4-methoxybenzo phenone (15, EA249EA-16-16-K7), 4-hydroxyacetophenone (16, EA249EA-16-12-K4), benzoic acid (17, EA249EA-16-24-K10), and trans-N-p-coumaroyl tyramine (19, EA249EA-16-3-K1) were also isolated without activity. Compounds 11 and 12 were new isomers. The known compounds 15, 16, and 19 were isolated from this plant for the first time. Moreover, compounds 15, 16, and 19 were found in the genus Anemarrhena and family Liliaceae for the first time. The structures of the isolates obtained in the present investigation were identified using 1D- and 2D- NMR techniques such as DEPT, 1H-1H COSY, 1H-1H NOESY, 1H-13C HSQC, and 1H-13C HMBC experiments as well as by comparing their data with the published values. The stereostructures of the new isomers were elucidated by aids of optical rotation and CD experiments.;백합과 (Liliaceae)에 속하는 식물인 지모 (Anemarrhena asphodeloides)의 근경으로부터 유래된 에칠아세테이트 분획물이 호흡기 세포융합 바이러스 (respiratory syncytial virus, RSV) 에 강력한 저해효과를 (IC50=3.18 mg/ml) 나타내어, 활성원인 물질을 추적하고자 단일성분 분리 및 분자구조분석 연구를 실시하였다. 이로부터 5개의 물질, 11-14, 18 이 RSV 저해 원인 성분으로 밝혀졌고, 활성대조물질로 사용된 리바비린보다 더 강한 활성을 보여 강력한 RSV저해 활성물질로 평가되었다. 그 외 4개의 물질 15-17, 19 은 비활성 물질로 밝혀졌다. 지모로부터 새로운 입체 이성체인 (R)-3"-methoxynyasol (11, EA249EA-16-17-K6), (R)-3'-hydroxy-4'-methoxy-4'-dehydroxynyasol (12, EA249EA-16-17-K8)과 7개의 알려진 구조인 (R)-4'-O-methylnyasol (13, EA249EA-16-6-K3), (R)-nyasol (14, EA249EA-16-12-K5), 2, 4'-dihydroxy-4-methoxybenzophenone (15, EA249EA-16-16-K7), 4-hydroxyacetophenone (16, EA249EA-16-12-K4), benzoic acid (17, EA249EA-16-24-K10), broussonin A (18, EA249EA-16-20-K9), trans-N-p-coumaroyltyramine (19, EA 249EA-16-3-K1)이 함께 분리되었다. 2, 4'-dihydroxy-4-metho xybenzophenone (15, EA 249EA-16-16-K7)은 천연물 유래 물질로는 처음 분리되었으며, 4-hydroxyacetophenone (16, EA249EA-16-12-K4), trans-N-p-coumaroyltyramine (19, EA 249EA-16 -3-K1)은 이 식물에서 처음 분리되었다. 새로운 화합물의 구조는 각종 이화학적 및 분광학적 기법을 사용하여 분석하였다. 호흡기 세포융합 바이러스 저해 활성은 물질 11-14, 18에서 대조군인 리바비린보다 큰 유효성을 보였는데, 이는 2개의 벤젠링 사이에 3개의 카본이 존재하는 공통점을 가지고 있어 이러한 구조적 특이성이 호흡기 세포융합 바이러스에 대한 저해 활성을 나타내는 것이라고 추측된다. 나아가 물질 11-19와 지모의 추출물에 대한 상기도 세포융합 바이러스 저해 활성은 처음 보고되는 바이다.
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