两色金鸡菊头状花序中聚炔类化学成分的研究

Polyacetylenes from capitulum of Coreopsis tinctoria

目的研究两色金鸡菊Coreopsis tinctoria头状花序的聚炔类化学成分。方法利用AB-8大孔树脂、硅胶、Sephadex LH-20、ODS及制备液相等色谱方法进行分离纯化,根据理化性质、波谱及旋光数据鉴定化合物的结构;采用脂多糖(LPS)诱导的BV-2细胞NO生成模型对分离得到的新化合物进行抗炎活性筛选。结果从两色金鸡菊干燥头状花序的50%乙醇提取物中分离得到5个聚炔类化合物,分别鉴定为(3S)-(6E,12E)-二烯-8,10-二炔-1-十四烷醇-3-O-β-D-葡萄糖苷(1)、(2S)-(3Z,11E)-二烯-5,7,9-三炔-1,2-十三碳二醇(2)、(2R)-(3E,5E,11E)-三烯-7,9-二炔-1,2-十三碳二醇(3)、(E)-7-苯基-2-烯-4,6-二炔-1-庚醇(4)、(Z)-7-苯基-2-烯-4,6-二炔-1-庚醇(5)。结论化合物1为新的炔苷类化合物,命名为金鸡菊炔苷E,显示微弱的抗炎活性;化合物3、5为首次从该植物中分离得到。

Objective To study the chemical constituents in the capitulum of Coreopsis tinctoria.Methods The constituents were separated and purified by AB-8 macroporous resin,silica gel,Sephadex LH-20,ODS column chromatography,and preparative HPLC.The structures were elucidated on the basis of chemical evidences,spectroscopic methods,and optical rotation data.The new compound was evaluated for its inhibitory activity against LPS-activated NO production in BV-2 microglial cells using the Griess assay.Results Five polyacetylenes were obtained from the fraction of 50% ethanol extract of C.tinctoria identified as（3S）-（6E,12E）-tetradecadiene-8,10-diyne-1-ol-3-O-β-D-glucopyranoside（1）,（2S）-（3Z,11E）-decadiene-5,7,9-triyne-1,2-diol（2）,（2R）-（3E,5E,11E）-triene-7,9-diyne-1,2-diol（3）,（E）-7-phenyl-2-heptene-4,6-diyn-1-ol（4）,and（Z）-7-phenyl-2-heptene-4,6-diyn-1-ol（5）.Conclusion Compound 1 is a new polyacetylene glycoside named coreoside E and shows weak anti-inflammatory activity.Compounds 3 and 5 are isolated from the plants of C.tinctoria for the first time.