紫茎泽兰中的萜类成分研究

Study on Terpenoids from Eupatorium Adenophorum Spreng.

关键词:  紫茎泽兰  化学成分  杜松烷型倍半萜  活性研究

Key words:  Eupatorium adenophorum Spreng.  chemical constituent  cadinane-type sesquiterpenoid  activity study

摘要:

目的 对紫茎泽兰中的萜类成分及其药理活性进行研究。方法 采用D101、HP20大孔树脂、硅胶柱色谱、葡聚糖凝胶色谱、高效液相色谱等多种分离分析手段，MS、¹H-NMR和¹³C-NMR等多种波谱技术以及ECD计算鉴定化合物结构，并采用MTT法对分离得到的单体化合物进行细胞毒活性的筛选。结果 从紫茎泽兰95%乙醇提取物的石油醚和乙酸乙酯萃取部位中分离得到10个化合物，分别鉴定为泽兰酮D (1)、thymoquinol 5-O-β-glucopyranoside (2)、thymoquinol2-O-β-glucopyranoside (3)、2R^*,3S^*-toxol-7-O-β-D-glucopyranoside (4)、6-甲氧基-山柰酚-7-O-β-D-葡萄糖苷(5)、万寿菊素-4’-甲氧基-7-O-β-D-葡萄糖苷(6)、6-hydroxykaempferol-7-O-β-D-glucopyranoside (7)、eupatonriochromene (8)、demethoxyencecalin (9)、encecalin (10)。化合物10对食管癌细胞的IC₅₀值为178.4 μmol·L^-1。结论 其中化合物1为新化合物，化合物6为首次从泽兰属中分离得到，化合物2，3，7为首次从紫茎泽兰中分离得到。化合物10对食管癌细胞Eca-109具有一定的细胞毒活性。

Abstract:

OBJECTIVE To study on the terpenoids and their pharmacological activities in Eupatorium adenophorum Spreng. METHODS D101, HP20 macroporous resin, silica gel column chromatography, dextran gel chromatography, high performance liquid chromatography and other methods were used for separation analysis. Their structures were determined by MS, ¹H-NMR and ¹³C-NMR and other spectrographic techniques, as well as ECD calculation. The cytotoxic activity of these compounds were screened by the MTT method. RESULTS Ten compounds were isolated from the petroleum ether and ethyl acetate extraction fractions of 95% ethanolic extracts of Eupatorium adenophorum Spreng, and they were identified as eupatorinone D(1), thymoquinol 5-O-β-glucopyranoside(2), thymoquinol 2-O-β-glucopyranoside(3), 2R^*,3S^*-toxol-7- O-β-D-glucopyranoside(4), 6-methoxy-kaempferol-7-O-β-D-glucoside(5), patuletin-4'-methoxyl-7-O-β-D-glucopyranoside(6), 6-hydroxykaempferol-7-O-β-D-glucopyranoside(7), eupatonriochromene(8), demethoxyencecalin(9) and encecalin(10). Among them, the IC₅₀ value of compound 10 against esophageal cancer cells was 178.4 μmol·L^-1. CONCLUSION Compound 1 is a new cadinane-type sesquiterpene, and compound 6 was isolated from genus Eupatorium for the first time, compounds 2, 3 and 7 were isolated from Eupatorium adenophorum Spreng for the first time. Compound 10 has certain cytotoxic activity against esophageal cancer cells Eca-109.