亚洲泽兰亚种大麻叶泽兰根中的新百里酚衍生物及细胞毒性成分。

New thymol derivatives and cytotoxic constituents from the root of Eupatorium cannabinum ssp. asiaticum.

作者信息

Chen Li-Chai, Lee Tzong-Huei, Sung Ping-Jyun, Shu Chih-Wen, Lim Yun-Ping, Cheng Ming-Jen, Kuo Wen-Lung, Chen Jih-Jung

机构信息

Department of Pharmacy of Zuoying Branch of Kaohsiung Armed Forces General Hospital, Kaohsiung 813, Taiwan.

出版信息

Chem Biodivers. 2014 Sep;11(9):1374-80. doi: 10.1002/cbdv.201300392.

DOI:10.1002/cbdv.201300392

PMID:25238078

Abstract

Two new thymol (=5-methyl-2-(1-methylethyl)phenol) derivatives, 8,10-didehydro-9-(3-methylbutanoyl)thymol 3-O-tiglate (1) and 9-O-angeloyl-8-methoxythymol 3-O-isobutyrate (2), were isolated from the root of Eupatorium cannabinum ssp. asiaticum, together with six known compounds, 3-8. The structures of 1 and 2 were determined through extensive 1D/2D-NMR and MS analyses. Among the isolates, 9-acetoxy-8,10-epoxythymol 3-O-tiglate (3) was the most cytotoxic, with IC50 values of 0.02±0.01, 1.02±0.07, and 1.36±0.12 μg/ml, respectively, against DLD-1, CCRF-CEM, and HL-60 cell lines. In addition, 10-acetoxy-9-O-angeloyl-8-hydroxythymol (4) and eupatobenzofuran (6) exhibited cytotoxicities, with IC50 values of 1.14±0.16 and 2.63±0.22, and 7.63±0.94 and 2.31±0.14 μg/ml, respectively, against DLD-1 and CCRF-CEM cell lines.

摘要

从亚洲泽兰亚种大麻叶泽兰的根部分离出两种新的百里香酚（=5-甲基-2-(1-甲基乙基)苯酚）衍生物，8,10-二脱氢-9-(3-甲基丁酰基)百里香酚3-O-惕各酸酯（1）和9-O-当归酰基-8-甲氧基百里香酚3-O-异丁酸酯（2），以及六种已知化合物3-8。通过广泛的一维/二维核磁共振和质谱分析确定了1和2的结构。在分离出的化合物中，9-乙酰氧基-8,10-环氧百里香酚3-O-惕各酸酯（3）细胞毒性最强，对DLD-1、CCRF-CEM和HL-60细胞系的IC50值分别为0.02±0.01、1.02±0.07和1.36±0.12μg/ml。此外，10-乙酰氧基-9-O-当归酰基-8-羟基百里香酚（4）和泽兰苯并呋喃（6）也表现出细胞毒性，对DLD-1和CCRF-CEM细胞系的IC50值分别为1.14±0.16和2.63±0.22，以及7.63±0.94和2.31±0.14μg/ml。