红鬼笔的麦角甾类成分研究

Ergost Steroids Constituents from the Sporocarp of Phallus rubicundus

目的:研究红鬼笔Phallus rubicundus(Bosc.)Fr.中的麦角甾类甾体成分,并测定麦角甾类成分对A549的细胞毒性。方法:利用正反相硅胶柱、Sephadex LH-20柱、制备薄层色谱及半制备HPLC等色谱方法进行分离纯化,根据理化性质、MS及NMR等波谱数据鉴定化合物的结构;采用MTT染色法测定化合物对A549细胞株的细胞毒性。结果:从红鬼笔95%乙醇提取物的乙酸乙酯部位中分离鉴定了10个麦角甾类化合物,分别鉴定为:citreoanthrasteroid(1)、1(10→6)abeo-麦角甾-5,7,9,22-四烯-11β-甲氧基-3α-醇(2)、(22E)-5α,8α-二环氧-麦角甾-6,9(11),22-三烯-3β-醇(3)、(22E)-5α,8α-二环氧-麦角甾-6,22-二烯-3β-醇(4)、(22E,24R)-麦角甾-7,22-二烯-3β,5α,6β-三醇(5)、(22E)-麦角甾-7,22-二烯-3β,5α,6α-三醇(6)、麦角甾-7,9(11),22-三烯-3β,5α,6α-三醇(7)、(22E)-麦角甾-8(14),22-二烯-3β,5α,6β,7α-四醇(8)、(22E,24R)-麦角甾-7,22-二烯-3β,5α,6β,9α-四醇(9)、4-hydroxy-17-methylincisterol(10)。结论:化合物1～10均为首次从鬼笔属真菌中分离得到。细胞毒性结果显示,化合物3对A549细胞株具有较强毒性,IC_(50)=13.76μmol/L。

Objective:To investigate the ergost steroids and cytotoxicity against A549 cell line from the sporocarp of Phallus rubicundus.Methods:The compounds were isolated and purified by column chromatographies over silica gel,ODS,Sephadex LH-20,preparative TLC and semi-preparative RP-HPLC.Their structures were elucidated by physicochemical properties,MS and NMR spectra datum.Cytotoxicity against A549 line was evaluated by MTT method.Results:Ten ergost steroids were obtained from the ethyl acetate layer of 95% ethyl alcohol extract of the Phallus rubicundus and their structures were identified as citreoanthrasteroid(1),1(10→6)abeo-ergosta-5,7,9,22-tetraen-11β-methoxy-3α-ol(2),(22E)-5α,8α-epidioxy-ergosta-6,9(11),22-trien-3β-ol(3),(22E)-5α,8α-epidioxy-ergosta-6,22-dien-3β-ol(4),(22E,24R)-ergosta-7,22-dien-3β,5α,6β-triol(5),(22E)-ergosta-7,22-dien-3β,5α,6α-triol(6),ergosta-7,9(11),22-trien-3β,5α,6α-triol(7),(22E)-ergosta-8(14),22-dien-3β,5α,6β,7α-tetraol(8),(22E,24R)-ergosta-7,22-dien-3β,5α,6β,9α-tetraol(9),4-hydroxy-17-methylincisterol(10).Conclusion:Compounds 1 to 10 are isolated from fungus of Phallus genus for the first time,and compound 3 has significant cytotoxicity against A549 cell line with the IC50 value of 13.76 μmol/L.