1株红树内生真菌Phomopsis sp.MGF222次级代谢产物及其活性研究

Study on bioactive secondary metabolites from a mangrove-derived fungus Phomopsis sp.MGF222

目的研究1株红树植物木果楝(Xylocarpus granatum Koenig)来源内生真菌Phomopsis sp.MGF222的次级代谢产物及其生物活性。方法利用硅胶柱层析、Sephadex LH-20凝胶柱层析、半制备高效液相色谱等色谱分离方法,对该菌发酵产物的乙酸乙酯浸膏的次级代谢产物进行分离纯化;综合利用核磁共振波谱(NMR)、质谱(MS)等波谱解析方法以及与文献数据对照,鉴定化合物的结构;并对化合物进行抗菌和α-葡萄糖苷酶抑制活性评价。结果从内生真菌Phomopsis sp.MGF222中分离鉴定出9个化合物(1~9),结构分别为12-epicitreoisocoumarinol(1)、5-hydroxy-7methoxy-4methylphthalide(2)、5-hydroxy-7-methoxy-4,6-dimethylphthalide(3)、(2-(2'-hydroxypropyl)-5-methyl-7-hydroxychromone(4)、tyrosol(5)、2-hydroxy-benzaldehyde(6)、5-hydroxymethyl-pyrrole-2-carbaldehyde(7)、(2S,2'R,3R,4E,8E,3'E)-2-(2'-hydroxy-3'-octadecenoylamino)-9-methyl-4,8-octadecadiene-l,3-diol(8)、(22E,24S)-5,8-epidioxy-24-methyl-cholesta-6,9(11),22-trien-3-ol(9);其中化合物9对白色念珠菌Canidia albicans显示抗菌活性;化合物2、5和8具有α-葡萄糖苷酶抑制活性。结论发现1个具有抗菌活性和3个具有α-葡萄糖苷酶抑制活性的化合物,具有重要的研究和应用价值。

Objective To investigate the secondary metabolites and their bioactivities of the mangrove-derived fungus Phomopsis sp.MGF222 isolated from the mangrove Xylocarpus granatum Koenig.Methods The column chromatography on silica gel,Sephadex LH-20,and semi-preparative High Performance Liquid Chromatography(HPLC)were used to isolate and purify the secondary metabolites from the ethyl acetate(EtOAc)fermentation broth of Phomopsis sp.MGF222.Their structures were elucidated by extensive NMR and MS spectroscopic data,and by comparison with the data of literature.The antibacterial activity and the inhibitory activity againstα-glucosidase of the isolated compounds were evaluated.Results Nine compounds were isolated from Phomopsis sp.MGF222.Their structures were identified as 12-epicitreoisocoumarinol(1),5-hydroxy-7 methoxy-4 methylphthalide(2),5-hydroxy-7-methoxy-4,6-dimethylphthalide(3),(2-(2’-hydroxypropyl)-5-methyl-7-hydroxychromone(4),tyrosol(5),2-hydroxy-benzaldehyde(6),5-hydroxymethyl-pyrrole-2-carbaldehyde(7),(2 S,2’R,3 R,4 E,8 E,3’E)-2-(2’-hydroxy-3’-octadecenoylamino)-9-methyl-4,8-octadecadiene-l,3-diol(8)and(22 E,24 S)-5,8-epidioxy-24-methyl-cholesta-6,9(11),22-trien-3-ol(9).Compound 9 exhibited significant inhibition activity against Canidia albicans.Compounds 2,5 and 8 showed strong inhibition activities againstα-glucosidase.Conclusion Among the isolated compounds,one compound showed significant antimicrobial activity,and three compounds showed strong inhibition activities againstα-glucosidase,which has important research and potential development value.