深海真菌Phomopsis tersa的次级代谢产物及其细胞毒活性研究

Study on the secondary metabolites from the deep-sea fungus Phomopsis tersa and their cytotoxic activities

目的研究深海真菌Phomopsis tersa FS441的次级代谢产物及其细胞毒活性。方法采用正、反相硅胶柱、凝胶柱和高效液相等多种色谱技术对菌株FS441的固体发酵产物进行分离纯化,并通过NMR、MS等波谱方法鉴定化合物结构,采用SRB法对得到的单体化合物进行细胞毒活性测试。结果从发酵物中分离纯化得到11个化合物,分别鉴定为:5α,8α-表二氧麦角甾-6,22-二烯-3β-醇(1)、麦角甾醇(2)、12-hydroxydehydrobotrydienol(3)、5,6-二羟基-2,3,6-三甲基环己-2-烯酮(4)、1,2-二羟基-3,4-脱氢蒽酮(5)、(1S,2S,3S,4R)-3-氯-4-(2-羟基丙吡啶-2-基)-1-甲基环己烷-1,2-二醇(6)、(-)-5-methylmellein(7)、酪醇(8)、胸腺嘧啶核苷(9)、(R)-(+)-甘油1-9(Z),12(Z)-十八碳二烯酸酯(10)、亚油酸(11)。结论化合物3~6为首次从Phomopsis属分离得到,化合物1和2对SF-268、MCF-7、HepG-2和A5494种肿瘤细胞株具有较弱的细胞毒活性。

Objective To study the secondary metabolites of the deep-sea fungus Phomopsis tersa FS441 and their cytotoxic activities.Methods The compounds were separated and purified from the solid fermentation product of the strain FS441 by silica gel,reverse phase silica gel,Sephadex LH-20 and high performance liquid chromatography(HPLC),their structures were identified by NMR and MS spectroscopy.Compounds were tested for their cytotoxic activities by SRB method.Results Eleven compounds were isolated and purified from the fermentation product and identified as 5 a,8 a-epidioxyergosta-6,22-dien-3 b-ol(1),ergosterol(2),12-hydroxydehydrobotrydienol(3),5,6-dihydroxy-2,3,6-trimethylcyclohex-2-enone(4),l,2-dihydroxy-3,4-dehydromenthone(5),(1 S,2 S,3 S,4 R)-3-chloro-4-(2-hydroxypropan-2-yl)-1-methylcyclohexane-1,2-diol(6),(-)-5-methylmellein(7),tyrosol(8),thymidine(9),(R)-(+)-glycerol 1-9(Z),12(Z)-octadecadienate(10),linoleic acid(11).Conclusion Compounds 3~6 were isolated from the genus Phomopsis for the first time.Compounds 1 and 2 exhibited weak cytotoxic activities against SF-268,MCF-7,HepG-2 and A549 cell lines.