来自莪术根茎的人纤维肉瘤HT 1080细胞侵袭抑制剂：苯丁类化合物莪术醇的结构

Invasion inhibitors of human fibrosarcoma HT 1080 cells from the rhizomes of Zingiber cassumunar: structures of phenylbutanoids, cassumunols.

作者信息

Matsuda Hisashi, Nakamura Seikou, Iwami Junko, Li Xuezheng, Pongpiriyadacha Yutana, Nakai Megumi, Kubo Miwa, Fukuyama Yoshiyasu, Yoshikawa Masayuki

机构信息

Kyoto Pharmaceutical University, Kyoto, Japan.

出版信息

Chem Pharm Bull (Tokyo). 2011;59(3):365-70. doi: 10.1248/cpb.59.365.

DOI:10.1248/cpb.59.365

PMID:21372419

Abstract

The methanolic extract and its EtOAc-soluble fraction from the rhizomes of Zingiber cassumunar inhibited invasion of human fibrosarcoma HT 1080 cells. From the EtOAc-soluble fraction, eight new phenylbutanoids, cassumunols A-H, were isolated together with 30 known constituents. The structures of new phenylbutanoids were elucidated on the basis of chemical and physicochemical evidence. Principal constituents were examined the inhibitory effects on the invasion of HT 1080 cells. Among them, phlain I and III, (E)-1-(3,4-dimethoxyphenyl)buta-1,3-diene, (E)-1-(2,4,5-trimethoxyphenyl)buta-1,3-diene, and (-)-β-sesquiphellandrene showed anti-invasion effects. Interestingly, (E)-1-(2,4,5-trimethoxyphenyl)buta-1,3-diene [inhibition (%) 46.8 ± 7.2 (p<0.05) at 30 µM] significantly inhibited the invasion, and only a weak cytotoxic effect was observed.

摘要

高良姜根茎的甲醇提取物及其乙酸乙酯可溶部分抑制人纤维肉瘤HT 1080细胞的侵袭。从乙酸乙酯可溶部分中，分离出8个新的苯丁类化合物，即高良姜醇A - H，以及30个已知成分。通过化学和物理化学证据阐明了新苯丁类化合物的结构。对主要成分进行了对HT 1080细胞侵袭的抑制作用研究。其中，phlain I和III、（E）-1-（3,4-二甲氧基苯基）丁-1,3-二烯、（E）-1-（2,4,5-三甲氧基苯基）丁-1,3-二烯和（-）-β-倍半水芹烯显示出抗侵袭作用。有趣的是，（E）-1-（2,4,5-三甲氧基苯基）丁-1,3-二烯[在30 μM时抑制率（%）为46.8 ± 7.2（p<0.05）]显著抑制侵袭，且仅观察到较弱的细胞毒性作用。