蝉花的化学成分

Chemical constituents of the fungus Cordyceps cicadae

采用树脂、硅胶、Sephadex-LH 20等现代色谱分离技术对蝉花(Cordyceps cicadae)90%甲醇提取物进行分离纯化,结合NMR、MS等多种波谱数据进行化学成分的鉴定,共分离得到13个化合物.分别为白僵菌素(1),白僵菌酮(2),cordycepamide E(3),(E)-(2R,3S)-2-(3′,4′-dihydroxyphenyl)-3-acetylamino-7-(N-acetyl-2″-aminethylene)-1,4-benzodioxane)(4),(E)-(2R,3S)-2-(3′,4′-dihydroxyphenyl)-3-acetylamino-6-(N-acetyl-2′′-aminoethylene)-1,4-benzodioxane(5),(2R,3S)-2-(3′,4′-dihydroxyphenyl)-3-acetylamino-7-(N-acetyl-2′′-aminoethyl)-1,4-benzodioxane(6),(2R,3S)-2-(3′,4′-dihydroxyphenyl)-3-acetylamino-6-(N-acetyl-2′′-aminoethyl)-1,4-benzodioxane(7),(Z)-(2R,3S)-2-(3′,4′-dihydroxyphenyl)-3-acetylamino-7-(N-acetyl-2″-aminethylene)-1,4-benzodioxane(8),5-hydroxy-4-(4-hydroxyphenyl)-3-methyl-2(5H)-furanone(9),1H-indole-3-carboxaldehyde(10),对羟基苯甲醛(11),对羟基苯甲酸甲酯(12),对羟基苯乙酸甲酯(13).化合物3、5-13均为首次从蝉花C.cicadae中分离.采用MTT法对化合物进行肿瘤细胞毒活性测定,并利用脂多糖(LPS)诱导的小鼠巨噬细胞RAW 264.7对化合物4-8进行抗炎活性测试.细胞毒活性测试结果表明,化合物1对Hela、SH-SY5Y、HCT116、MCF-7、MDA-MB-231、4T1细胞株具有一定的抑制作用,IC50值分别为3.511±0.325、3.555±0.232、4.367±0.320、9.395±1.014、16.92±3.444、7.476±0.634μmol/L.抗炎活性测试结果表明化合物4-8均能降低LPS诱导的RAW 264.7细胞释放NO、TNF-α和IL-6的量,具有抗炎活性.(图4表1参42)

The 90%methanol extracts of Cordyceps cicadae,such as resin,silica gel,Sephadex-LH 20,were isolated and purified by chromatography and then their structures were elucidated on the basis of NMR and MS spectroscopic evidences.Thirteen known compounds were isolated and elucidated beauvericin(1),bassiatin(2),Cordycepamide E(3),(E)-(2R,3S)-2-(3′,4′-dihydroxyphenyl)-3-acetylamino-7-(N-acetyl-2″-aminethylene)-1,4-benzodioxane)(4),(E)-(2R,3S)-2-(3′,4′-dihydroxyphenyl)-3-acetylamino-6-(N-acetyl-2′′-aminoethylene)-1,4-benzodioxane(5),(2R,3S)-2-(3′,4′-dihydroxyphenyl)-3-acetylamino-7-(N-acetyl-2′′-aminoethyl)-1,4-benzodioxane(6),(2R,3S)-2-(3′,4′-dihydroxyphenyl)-3-acetylamino-6-(N-acetyl-2′′-aminoethyl)-1,4-benzodioxane(7),(Z)-(2R,3S)-2-(3′,4′-dihydroxyphenyl)-3-acetylamino-7-(N-acetyl-2″-aminethylene)-1,4-benzodioxane(8),5-hydroxy-4-(4-hydroxyphenyl)-3-methyl-2(5H)-furanone(9),1H-indole-3-carboxaldehyde(10),p-hydroxybenzaldehyde(11),methyl 4-hydroxybenzoate(12),and methyl 4-Hydroxyphenylacetate(13).Compounds 3 and 5-13 were isolated from the fungus of C.cicadae for the first time and the MTT method was applied to test their cytotoxicity of the isolated compounds.Additionally,compounds 4-8 were screened for antiinflammatory activity by LPS-induced RAW 264.7 cells.Compound 1 exhibited weak inhibitory activity against Hela,SH-SY5Y,HCT116,MCF-7,MDA-MB-231 and 4T1 cells,with IC50 values of 3.511±0.325,3.555±0.232,4.367±0.320,9.395±1.014,16.92±3.444 and 7.476±0.634μmol/L,respectively.Compounds 4-8 can inhibit the production expression of NO,TNF-αand IL-6 in RAW 264.7 macrophages,and exhibit anti-inflammatory activity.