小紫金牛（Ardisia chinensis Benth）和猴耳环（Pithecellobium clypearia Benth）的化学成分和生物活性研究
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摘要
本文探讨了小紫金牛(Ardisia chinensis Benth)和猴耳环(Pithecellobium clypearia Benth)的化学成分和生物活性。
采用细胞病变抑制法和四甲基偶氮唑盐比色法，测定了小紫金牛提取物和各溶剂萃取部位的抗柯萨奇病毒B组3型(Cox B3)和单纯疱疹病毒1型(HSV-1)的活性。实验结果表明，各样品对Cox B3病毒的抑制作用普遍强于对HSV-1病毒的作用；其中，乙醇提取物和水提物对两种病毒显示不同程度的抑制作用，而水提物对Cox B3病毒的作用最强，半数抑制浓度(IC50)为31.3μg／mL，选择性指数(SI)大于32；乙醇提取物经不同溶剂萃取后，各萃取部位的抗病毒活性随着萃取溶剂极性的增大而增强，正丁醇萃取部位和余水部位显示较强的抗Cox B3病毒活性，IC_(50)分别为15.7和31.3μg／mL，S1分别为15.9和60；正丁醇萃取部位经大孔吸附树脂初步分离得到的水洗脱部位表现出极强的抗Cox B3病毒活性，IC50为7.8μg／mL，SI达到57.7。具有明显抗Cox B3病毒活性的余水部位、正丁醇萃取部位和正丁醇萃取部位经大孔吸附树脂初步分离得到的水洗脱部位对苯酚—硫酸试剂和α—萘酚试剂均呈阳性反应，推断小紫金牛抗Cox B3病毒的活性成分可能是高极性的糖。
小紫金牛多糖的成分和抗Cox B3病毒活性研究结果表明，小紫金牛抗病毒活性多糖(ACP-1)为中性多糖，单糖组成主要为葡萄糖(＞50％)，平均分子量为40037 Da，对CoxB3病毒的IC50为3.9μg／mL，SI超过256。
对小紫金牛乙酸乙酯萃取部位进行了分离，采用光谱分析和文献对照的方法对分离所得单体的结构进行确定。从中分离和鉴定出8个单体化合物。他们分别是：水杨酸(1)，紫金牛酸(2)，对羟基间甲氧基苯甲酸(3)，没食子酸乙酯(4)，4-羟基-3，5-二甲氧基苯甲酸(5)，原儿茶酸(6)，没食子酸(7)和儿茶素(8)。上述化合物均为首次从该植物分离得到，其中儿茶素(8)为首次从该属植物中得到，紫金牛酸(2)为新化合物。体外抗病毒的活性测定表明仅儿茶素(8)显示轻微的抗Cox B3病毒的作用。
The chemical constituents and bioactivities of Ardisia chinensis Benth and Pithecellobium clypearia Benth were discussed in the present study.
The anti-coxsackie B3 (Cox B3) virus activities and anti-herpes simplex virus 1 (HSV-1) activities of extracts and fractions from A. chinensis were tested by cytopathic effect reduction assay and MTT assay. As a result, the extracts and fractions exhibited anti-Cox B3 virus activity stronger than anti-HSV-1 virus activity. Aqueous extract and 95% ethanol extract showed antiviral activities against Cox B3 virus and HSV-1 virus to different extent, while the aqueous extract possessed the most potent anti-Cox B3 virus activity, with the 50% inhibitory concentration (IC_(50)) and selective index (SI) of 31.3 μg/mL and over 32, respectively. After the EtOH extract was fractionated with organic solvents, the antiviral activities of various fractions increased with the increase of their polarities. Residue fraction and n-BuOH fraction exhibited more potent anti-Cox B3 virus activities, with IC50 values and SI values of 15.7 and 31.3 μg/mL, 15.9 and 6.0, respectively. Notably, when n-BuOH fraction was chromatographed with macroporous resin column, the water elution fraction (Ab-1) showed potent antiviral activity against Cox B3 virus with IC_(50) value of 7.8 μg/mL and SI value of 57.7. Residue fraction, n-BuOH fraction and Ab-1 showed positive reactions for phenol-H_2SO_4 and α-naphthol reagents. All these suggested that the antiviral constituents in A. chinensis maybe its polysaccharide.
The polysaccharide of A. chinensis was extracted and its anti-Cox B3 virus activity was tested. The result showed that the polysaccharide of A. chinensis (ACP-1) is a neutral polysaccharide in which D-glucose is the major sugar composition (more than a half), with average molecular weight of 40037 Da. The IC50 value and SI value against Cox B3 virus of ACP-1 are 3.9 μg/mL and over 256, respectively.
The chemical constituents of ethyl acetate fraction of A. chinensis were isolated. Their structures were elucidated by spectroscopic analysis and comparison with published data. Eight compounds were obtained and characterized to be salicylic acid
采用细胞病变抑制法和四甲基偶氮唑盐比色法，测定了小紫金牛提取物和各溶剂萃取部位的抗柯萨奇病毒B组3型(Cox B3)和单纯疱疹病毒1型(HSV-1)的活性。实验结果表明，各样品对Cox B3病毒的抑制作用普遍强于对HSV-1病毒的作用；其中，乙醇提取物和水提物对两种病毒显示不同程度的抑制作用，而水提物对Cox B3病毒的作用最强，半数抑制浓度(IC50)为31.3μg／mL，选择性指数(SI)大于32；乙醇提取物经不同溶剂萃取后，各萃取部位的抗病毒活性随着萃取溶剂极性的增大而增强，正丁醇萃取部位和余水部位显示较强的抗Cox B3病毒活性，IC_(50)分别为15.7和31.3μg／mL，S1分别为15.9和60；正丁醇萃取部位经大孔吸附树脂初步分离得到的水洗脱部位表现出极强的抗Cox B3病毒活性，IC50为7.8μg／mL，SI达到57.7。具有明显抗Cox B3病毒活性的余水部位、正丁醇萃取部位和正丁醇萃取部位经大孔吸附树脂初步分离得到的水洗脱部位对苯酚—硫酸试剂和α—萘酚试剂均呈阳性反应，推断小紫金牛抗Cox B3病毒的活性成分可能是高极性的糖。
小紫金牛多糖的成分和抗Cox B3病毒活性研究结果表明，小紫金牛抗病毒活性多糖(ACP-1)为中性多糖，单糖组成主要为葡萄糖(＞50％)，平均分子量为40037 Da，对CoxB3病毒的IC50为3.9μg／mL，SI超过256。
对小紫金牛乙酸乙酯萃取部位进行了分离，采用光谱分析和文献对照的方法对分离所得单体的结构进行确定。从中分离和鉴定出8个单体化合物。他们分别是：水杨酸(1)，紫金牛酸(2)，对羟基间甲氧基苯甲酸(3)，没食子酸乙酯(4)，4-羟基-3，5-二甲氧基苯甲酸(5)，原儿茶酸(6)，没食子酸(7)和儿茶素(8)。上述化合物均为首次从该植物分离得到，其中儿茶素(8)为首次从该属植物中得到，紫金牛酸(2)为新化合物。体外抗病毒的活性测定表明仅儿茶素(8)显示轻微的抗Cox B3病毒的作用。
The chemical constituents and bioactivities of Ardisia chinensis Benth and Pithecellobium clypearia Benth were discussed in the present study.
The anti-coxsackie B3 (Cox B3) virus activities and anti-herpes simplex virus 1 (HSV-1) activities of extracts and fractions from A. chinensis were tested by cytopathic effect reduction assay and MTT assay. As a result, the extracts and fractions exhibited anti-Cox B3 virus activity stronger than anti-HSV-1 virus activity. Aqueous extract and 95% ethanol extract showed antiviral activities against Cox B3 virus and HSV-1 virus to different extent, while the aqueous extract possessed the most potent anti-Cox B3 virus activity, with the 50% inhibitory concentration (IC_(50)) and selective index (SI) of 31.3 μg/mL and over 32, respectively. After the EtOH extract was fractionated with organic solvents, the antiviral activities of various fractions increased with the increase of their polarities. Residue fraction and n-BuOH fraction exhibited more potent anti-Cox B3 virus activities, with IC50 values and SI values of 15.7 and 31.3 μg/mL, 15.9 and 6.0, respectively. Notably, when n-BuOH fraction was chromatographed with macroporous resin column, the water elution fraction (Ab-1) showed potent antiviral activity against Cox B3 virus with IC_(50) value of 7.8 μg/mL and SI value of 57.7. Residue fraction, n-BuOH fraction and Ab-1 showed positive reactions for phenol-H_2SO_4 and α-naphthol reagents. All these suggested that the antiviral constituents in A. chinensis maybe its polysaccharide.
The polysaccharide of A. chinensis was extracted and its anti-Cox B3 virus activity was tested. The result showed that the polysaccharide of A. chinensis (ACP-1) is a neutral polysaccharide in which D-glucose is the major sugar composition (more than a half), with average molecular weight of 40037 Da. The IC50 value and SI value against Cox B3 virus of ACP-1 are 3.9 μg/mL and over 256, respectively.
The chemical constituents of ethyl acetate fraction of A. chinensis were isolated. Their structures were elucidated by spectroscopic analysis and comparison with published data. Eight compounds were obtained and characterized to be salicylic acid
引文
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