拟茎点霉属真菌福士拟茎点霉发酵产物中的1个具有抗菌活性的新二苯醚类化合物
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摘要
目的对拟茎点霉属真菌福士拟茎点霉Phomopsis fukushii发酵产物的化学成分进行研究。方法运用硅胶、凝胶及RP-HPLC等多种色谱技术进行分离纯化得到化合物,并根据理化性质和波谱数据鉴定化合物的结构。结果从福士拟茎点霉发酵产物中分离到4个异戊基二苯醚类化合物,分别鉴定为1-[4-(3-羟基-5-甲基苯氧基)-2-甲氧基-6-甲基苯]-3-甲基丁基-3-烯-2-酮(1)、diorcinol C(2)、diorcinol D(3)和diorcinol E(4)。对化合物1进行抗菌活性筛选,发现其对耐甲氧西林金黄色葡萄球菌(MRSA)菌株的MIC_(90)值为(54±4)μg/mL。结论化合物1为新化合物,命名为拟茎点二苯醚A;化合物2~4为拟茎点属真菌中首次发现的异戊基二苯醚类化合物,化合物1具有突出的抗菌活性,接近阳性对照左氧氟沙星的MIC_(90)值。
Objective Try to find the new biological compounds, the research on the chemical constituents in the fermentation products of an endophytic fungus Phomopsis fukushii had been carried out. Methods The chemical constituents in this fermentation products were isolated by silica gel, Sephadex LH-20 column chromatographies and RP-HPLC methods. Their structures were elucidated by using various spectroscopic techniques. Results Four pentylated diphenyl ethers(1—4) were isolated from this fermentation products, and the new compound(1) was evaluated for its anti-methicillin-resistant Staphylococcus aureus(anti-MRSA) activity. Compounds 2—4 were identified as diorcinol C, diorcinol D, and diorcinol E. Conclusion Compounds 2—4 are isolated from the fermentation products of endophytic fungus Phomopsis fukushii for the first time. Compound 1 is a new compound named phomodiphenyl ether A and given the system name of 1-[4-(3-hydroxy-5-methylphenoxy)-2-methoxy-6-methylphenyl]-3-methylbut-3-en-2-one. Compound 1 also shows strong anti-MRSA activity with MIC90 value of(54 ± 4) μg/mL. This valve is close to that ofpositive control, levofloxacin with MIC_(90) value of [≥(56 ± 6) μg/mL].
Objective Try to find the new biological compounds, the research on the chemical constituents in the fermentation products of an endophytic fungus Phomopsis fukushii had been carried out. Methods The chemical constituents in this fermentation products were isolated by silica gel, Sephadex LH-20 column chromatographies and RP-HPLC methods. Their structures were elucidated by using various spectroscopic techniques. Results Four pentylated diphenyl ethers(1—4) were isolated from this fermentation products, and the new compound(1) was evaluated for its anti-methicillin-resistant Staphylococcus aureus(anti-MRSA) activity. Compounds 2—4 were identified as diorcinol C, diorcinol D, and diorcinol E. Conclusion Compounds 2—4 are isolated from the fermentation products of endophytic fungus Phomopsis fukushii for the first time. Compound 1 is a new compound named phomodiphenyl ether A and given the system name of 1-[4-(3-hydroxy-5-methylphenoxy)-2-methoxy-6-methylphenyl]-3-methylbut-3-en-2-one. Compound 1 also shows strong anti-MRSA activity with MIC90 value of(54 ± 4) μg/mL. This valve is close to that ofpositive control, levofloxacin with MIC_(90) value of [≥(56 ± 6) μg/mL].
引文
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[6]Zhou M,Zhou K,Zhao Y L,et al.Three new prenylated xanthones from Comastoma pedunculatum and their anti-tobacco mosaic virus activity[J].Phytochem Lett,2015,11:245-248.
[7]Gong D L,Wang X J,Xiang Z D,et al.Diphenyl etheric metabolites from Streptomyces sp.neau 50[J].J Antibiot,2011,42(44):465-467.
[8]Gao H Q,Zhou L,Cai S X,et al.Diorcinols B-E,new prenylated diphenyl ethers from the marine-derived fungus Aspergillus versicolor ZLN-60[J].J Antibiot,2013,66(9):539-542.
[2]王茜,申仕康,张爱丽,等.滇重楼内生真菌分离与多样性研究[J].中国中药杂志,2013,38(22):3838.
[3]李雪光,潘凤娟,宋洁,等.拟茎点霉属及其病害研究进展[J].大豆科技,2012(6):32-37.
[4]Yang J X,Xu F,Huang C H,et al.Metabolites from the mangrove endophytic fungus Phomopsis sp.(#zsu-H76)[J].Eur J Org Chem,2010,19:3692-3695.
[5]Erbert C,Lopes A A,Yokoya N S,et al.Antibacterial compound from the endophytic fungus Phomopsis longicolla isolated from the tropical red seaweed Bostrychia radicans[J].Bot Mar,2012,55(4):435-440.
[6]Zhou M,Zhou K,Zhao Y L,et al.Three new prenylated xanthones from Comastoma pedunculatum and their anti-tobacco mosaic virus activity[J].Phytochem Lett,2015,11:245-248.
[7]Gong D L,Wang X J,Xiang Z D,et al.Diphenyl etheric metabolites from Streptomyces sp.neau 50[J].J Antibiot,2011,42(44):465-467.
[8]Gao H Q,Zhou L,Cai S X,et al.Diorcinols B-E,new prenylated diphenyl ethers from the marine-derived fungus Aspergillus versicolor ZLN-60[J].J Antibiot,2013,66(9):539-542.