Shi Shuyun, Huang Kelong, Zhang Yuping, Zhao Yu, Du Qizhen
School of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China.
J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Nov 1;859(1):119-24. doi: 10.1016/j.jchromb.2007.09.016. Epub 2007 Sep 19.
Although Laggera pterodonta, a folk medicine has been widely used for several centuries as an antiviral agent, there have been no studies to identify its antiviral components. A bioassay-guided phytochemical examination of L. pterodonta disclosed that its aqueous extract, which was made up of three dicaffeoylquinic acids showed significant inhibitory activity of virus replication. Then a simple and efficient preparative high-speed counter-current chromatography (HSCCC) method was successfully established by using ethyl acetate-n-butanol-water (3:2:5, v/v) as the two-phase solvent system to isolate and purify three bioactive dicaffeoylquinic acids, 3,5-O-dicaffeoylquinic acid, 3,4-O-dicaffeoylquinic acid and 4,5-O-dicaffeoylquinic acid. The flow rate was 1.5 ml/min and revolution speed was 800 rpm. The isolation was done in less than 6h, and 34.6 mg of 3,5-O-dicaffeoylquinic acid, 29.4 mg of 3,4-O-dicaffeoylquinic acid and 27.1mg of 4,5-O-dicaffeoylquinic acid was yielded from 600 mg of the crude sample in one-step separation with the purity of 98.3%, 96.7% and 96.2%, respectively, as determined by high-performance liquid chromatography (HPLC). The structures of these three bioactive dicaffeoylquinic acids were identified by ultraviolet (UV), electrospray ionization mass spectrometry (ESI-MS), proton nuclear magnetic resonance ((1)H NMR) and carbon-13 nuclear magnetic resonance (13C NMR). In the antiviral experiment, three dicaffeoylquinic acids all showed significant inhibitory activity against herpes simplex virus-1 (HSV-1), herpes simplex virus-2 (HSV-2) and influenza viruses A (IVA) in vitro with high selectivity indexes. However, among the three compounds, 3,5-O-dicaffeoylquinic acid and 4,5-O-dicaffeoylquinic acid were the more active than 3,4-O-dicaffeoylquinic acid against HSV-1, HSV-2 and IVA. This study demonstrated a direct link between the antiviral activity of L. pterodonta and the three dicaffeoylquinic acids.
虽然作为一种民间药物的翼齿六棱菊已经被广泛用作抗病毒剂几个世纪了，但尚未有研究鉴定其抗病毒成分。对翼齿六棱菊进行的生物活性导向的植物化学研究表明，其由三种二咖啡酰奎宁酸组成的水提取物对病毒复制具有显著的抑制活性。然后，以乙酸乙酯 - 正丁醇 - 水（3:2:5，v/v）作为两相溶剂体系，成功建立了一种简单高效的制备型高速逆流色谱（HSCCC）方法，用于分离和纯化三种生物活性二咖啡酰奎宁酸，即3,5 - O - 二咖啡酰奎宁酸、3,4 - O - 二咖啡酰奎宁酸和4,5 - O - 二咖啡酰奎宁酸。流速为1.5 ml/min，转速为800 rpm。分离在不到6小时内完成，从600 mg粗样品中一步分离得到34.6 mg的3,5 - O - 二咖啡酰奎宁酸、29.4 mg的3,4 - O - 二咖啡酰奎宁酸和27.1 mg的4,5 - O - 二咖啡酰奎宁酸，通过高效液相色谱（HPLC）测定其纯度分别为98.3%、96.7%和96.2%。通过紫外（UV）、电喷雾电离质谱（ESI - MS）、质子核磁共振（(1)H NMR）和碳 - 13核磁共振（13C NMR）鉴定了这三种生物活性二咖啡酰奎宁酸的结构。在抗病毒实验中，三种二咖啡酰奎宁酸在体外对单纯疱疹病毒1型（HSV - 1）、单纯疱疹病毒2型（HSV - 2）和甲型流感病毒（IVA）均表现出显著的抑制活性，且具有高选择性指数。然而，在这三种化合物中，3,5 - O - 二咖啡酰奎宁酸和4,5 - O - 二咖啡酰奎宁酸对HSV - 1、HSV - 2和IVA的活性比3,4 - O - 二咖啡酰奎宁酸更强。这项研究证明了翼齿六棱菊的抗病毒活性与这三种二咖啡酰奎宁酸之间存在直接联系。
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