Niu Siwen, Liu Dong, Proksch Peter, Shao Zongze, Lin Wenhan
College of Marine Life, Ocean University of China, Qingdao 266003, China.
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China.
Mar Drugs. 2015 Apr 22;13(4):2526-40. doi: 10.3390/md13042526.
Eleven new polyphenols namely spiromastols A-K (1-11) were isolated from the fermentation broth of a deep sea-derived fungus Spiromastix sp. MCCC 3A00308. Their structures were determined by extensive NMR data and mass spectroscopic analysis in association with chemical conversion. The structures are classified as diphenyl ethers, diphenyl esters and isocoumarin derivatives, while the n-propyl group in the analogues is rarely found in natural products. Compounds 1-3 exhibited potent inhibitory effects against a panel of bacterial strains, including Xanthomanes vesicatoria, Pseudomonas lachrymans, Agrobacterium tumefaciens, Ralstonia solanacearum, Bacillus thuringensis, Staphylococcus aureus and Bacillus subtilis, with minimal inhibitory concentration (MIC) values ranging from 0.25 to 4 µg/mL. The structure-activity relationships are discussed, while the polychlorinated analogues 1-3 are assumed to be a promising structural model for further development as antibacterial agents.
从深海来源的螺旋孢菌属真菌Spiromastix sp. MCCC 3A00308的发酵液中分离出11种新的多酚类化合物,即螺旋孢醇A - K(1 - 11)。通过广泛的核磁共振数据和质谱分析,并结合化学转化确定了它们的结构。这些结构被归类为二苯醚、二苯酯和异香豆素衍生物,而类似物中的正丙基在天然产物中很少见。化合物1 - 3对一组细菌菌株表现出强效抑制作用,包括番茄疮痂病菌、黄瓜角斑病菌、根癌土壤杆菌、青枯雷尔氏菌、苏云金芽孢杆菌、金黄色葡萄球菌和枯草芽孢杆菌,最低抑菌浓度(MIC)值范围为0.25至4 μg/mL。讨论了构效关系,同时假定多氯代类似物1 - 3是作为抗菌剂进一步开发的有前景的结构模型。