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从丁香 Syzygium campanulatum Korth 中分离得到的二甲氧基小豆蔻明的分离、鉴定、晶体结构解析及抗癌研究

Isolation, Characterization, Crystal Structure Elucidation, and Anticancer Study of Dimethyl Cardamonin, Isolated from Syzygium campanulatum Korth.

机构信息

Department of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia.

EMAN Research and Testing Laboratory, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia.

出版信息

Evid Based Complement Alternat Med. 2014;2014:470179. doi: 10.1155/2014/470179. Epub 2014 Oct 28.

Abstract

Syzygium campanulatum Korth is an equatorial, evergreen, aboriginal shrub of Malaysia. Conventionally it has been used as a stomachic. However, in the currently conducted study dimethyl cardamonin or 2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone (DMC) was isolated from S. campanulatum Korth, leaf extract. The structural characterization of DMC was carried out by making use of various techniques including UV, IR, NMR spectral followed by LC-MS, and X-ray crystallographic techniques. For determining the purity of compound, highly effective techniques including TLC, HPLC, and melting point were used. The cytotoxicity of DMC and three different extracts of S. campanulatum was evaluated against human colon cancer cell line (HT-29) by three different assays. DMC and ethanolic extract revealed potent and dose-dependent cytotoxic activity on the cancer cell line with IC50 12.6 and 90.1 µg/mL, respectively. Quite astonishingly to our knowledge, this is the very first report on S. campanulatum as being a rich source (3.5%) of DMC, X-ray crystallography, and anticancer activity on human colon cancer cells.

摘要

桃金娘科丁香蓼是一种生长在赤道地区的常绿原生灌木,原产于马来西亚。传统上,它被用作胃药。然而,在目前进行的研究中,二甲氧基小豆蔻明或 2',4'-二羟基-6'-甲氧基-3',5'-二甲基查尔酮(DMC)从丁香蓼叶提取物中被分离出来。DMC 的结构特征是通过利用各种技术,包括 UV、IR、NMR 光谱,随后是 LC-MS 和 X 射线晶体学技术进行的。为了确定化合物的纯度,使用了高效的技术,包括 TLC、HPLC 和熔点。通过三种不同的测定方法评估 DMC 和丁香蓼的三种不同提取物对人结肠癌细胞系(HT-29)的细胞毒性。DMC 和乙醇提取物对癌细胞系表现出显著的、剂量依赖性的细胞毒性,IC50 值分别为 12.6 和 90.1μg/mL。令人惊讶的是,据我们所知,这是关于丁香蓼作为 DMC 的丰富来源(3.5%)、X 射线晶体学和对人结肠癌细胞的抗癌活性的首次报道。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/756f/4228816/50e855ceabf6/ECAM2014-470179.001.jpg

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