怀菊花中1个新的没药烷型倍半萜

A new bisabolane-type sesquiterpenoid from Chrysanthemum morifolium

目的研究怀菊花Chrysanthemum morifolium的化学成分。方法采用硅胶、ODS、Sephadex LH-20以及半制备HPLC等方法进行分离纯化,根据波谱数据并结合文献对化合物结构进行鉴定。采用脂多糖(lipopolysaccharide,LPS)诱导小鼠巨噬细胞RAW264.7模型,以抑制炎性细胞因子一氧化氮(NO)的分泌为评价指标对分离得到的化合物进行体外抗炎活性评价。结果从怀菊花二氯甲烷提取物中分离得到7个化合物,分别为(6S,7R,10R)-没药烷-7-羟基-10,11-环氧-4-酮(1)、黑麦草内酯(2)、(4R)-1-甲基-4-(1-羟基异丙基)环己烯-6-酮(3)、2-甲氧基对苯二酚(4)、4-(3-羟丙基)苯酚(5)、5-(3-羟丙基)-2-甲氧基苯酚(6)、4-甲基苯酚(7)。结论化合物1为新的没药烷型倍半萜,命名为怀菊花没药烷A。除化合物2外,其余化合物均为首次从该属植物中分离得到。化合物1和3有显著NO抑制作用,其半数抑制浓度(median inhibition concentration,IC50)值分别为9.2、38.9μmol/L。

Objective To study the chemical constituents from Chrysanthemum morifolium.Methods The extract from C.morifolium was isolated and purified by silica gel column,ODS,Sephadex LH-20 and semi-preparative HPLC.Their structures were identified by spectral analysis combined with literature.Inhibiting the secretion of inflammatory cytokine nitric oxide(NO)was used as the evaluating indicator,the model of lipopolysaccharide(LPS)-induced mouse macrophage RAW264.7 cells was used to evaluate the in vitro anti-inflammatory activity of isolated compounds.Results A total of seven compounds were obtained from the dichloromethane extract of C.morifolium and their structures were identified as(6S,7R,10R)-bisabolane-7-hydroxy-10,11-epoxide-4-one(1),loliolide(2),(4R)-1-methyl-4-(1-hydroxyisopropyl)cyclohexene-6-one(3),2-methoxyhydroquinone(4),4-(3-hydroxypropyl)phenol(5),5-(3-hydroxypropyl)-2-methoxyphenol(6),4-methylphenol(7).Conclusion Compound 1 is a new bisabolane-type sesquiterpenoid,named chrysanbisabane A.All compounds except compound 2 were isolated from this genus for the first time.Compounds 1 and 3 showed a significant NO inhibition activity with median inhibition concentration(IC50)values of 9.2μmol/L and 38.9μmol/L,respectively.