荚果蕨植物内生真菌Penicillium sp.SYP-F-7610的抑菌活性次级代谢产物研究

Study on antibacterial secondary metabolites from the endophytic fungus Penicillium sp.SYP-F-7610 isolated from Matteuccia struthiopteris

目的研究荚果蕨根茎内生真菌Penicillium sp.SYP-F-7610发酵液中抑菌活性次级代谢产物。方法采用硅胶柱色谱、ODS柱色谱、反相半制备HPLC等分离菌株发酵液中的次级代谢产物,根据比旋光度和波谱学数据(MS、^(1)H NMR、^(13)C NMR)进行结构鉴定。采用比浊法测试次级代谢产物的抑菌活性。结果从荚果蕨根茎内生真菌Penicilliumsp.SYP-F-7610发酵液中分离鉴定了7个化合物,分别为青霉酸(1)、3,5,6-三甲基-2,4-二羟基苯甲酸甲酯(2)、苔黑酚(3)、4-羟基苯乙酸甲酯(4)、6-hydroxy-5-methoxy-3-methyl-3,6-dihydro-2H-pyran-4-carboxylicacid(5)、chermesinone A(6)和(R)-甲羟戊酸内酯(7)。化合物1对大肠埃希菌(Escherichia coli CMCC44103)、乙型副伤寒沙门菌(Salmonela paratyphi B CMCC50094)、蜡样芽胞杆菌(Bacillus cereus ATCC14579)和肺炎克雷伯菌(Klebsiella pneumoniae CMCC46117)表现出抑制作用,IC_(50)值为3.19~6.79μg/mL。结论本文首次对荚果蕨属植物的内生真菌进行研究,发现荚果蕨根茎内生真菌Penicillium sp.SYP-F-7610的次级代谢产物结构类型丰富、生物活性多样,值得深入研究。化合物5为首次报道从青霉属真菌次级代谢产物中分离得到。化合物1为首次报道对乙型副伤寒沙门菌具有抑制活性。

Objective To study the antibacterial secondary metabolites from the culture broth produced by endophytic fungus Penicillium sp.SYP-F-7610 isolated from the rhizomes of Matteuccia struthiopteris.Methods The secondary metabolites were isolated and purified using various chromatographic techniques,including silica gel column chromatography,ODS column chromatography,and semi-preparative high performance liquid chromatography.Their structures were identified by various spectroscopic data analysis and comparison such as data from specific rotation,MS,^(1)H NMR,and ^(13)C NMR.Results Seven compounds were isolated and identified as penicillium acid(1),methyl 2,4-dihydroxy-3,5,6-trimethylbenzoate(2),orcinol(3),methyl 4-hydroxyphenylacetate(4),6-hydroxy-5-methoxy-3-methyl-3,6-dihydro-2H-pyran-4-carboxylic acid(5),chermesinone A(6),and(R)-mevalonolactone(7).Compound 1 exhibited the inhibitory activities against Escherichia coli CMCC44103,Salmonela paratyphi B CMCC50094,Bacillus cereus ATCC14579,and Klebsiella pneumoniae CMCC46117 with IC_(50) values of 3.19~6.79μg/mL.Conclusion No previous study regarding the endophytic fungus isolated from Matteuccia sp.has been reported.The secondary metabolites from the Penicillium sp.SYP-F-7610 isolated from the rhizomes of Matteuccia struthiopteris possess rich structures and diverse bioactivities,which is worthy of further investigation.Compound 5 has not been previously reported from the secondary metabolites of Penicillium genus.It is the first reported that compound 1 displayed the inhibitory activity against Salmonela paratyphi B.