New polyphenols from a deep sea Spiromastix sp. Fungus, and their antibacterial activities.
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.
College of Marine Life, Ocean University of China, Qingdao 266003, China. liudong_1982@126.com.|State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China. liudong_1982@126.com.
Siwen
S
Niu
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China. liudong_1982@126.com.
Dong
D
Liu
Institute für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, Geb.26.23, 40225 Düsseldorf, Germany. proksch@uni-duesseldor.de.
Peter
P
Proksch
College of Marine Life, Ocean University of China, Qingdao 266003, China. shaozz@163.com.|Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, SOA, Xiamen 361005, China. shaozz@163.com.
Zongze
Z
Shao
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China. whlin@bjmu.edu.cn.
Wenhan
W
Lin
D000531:Altitude; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D059001:Aquatic Organisms / Q000737:chemistry*; D001203:Ascomycota / Q000737:chemistry*; D001267:Atlantic Ocean; D056449:Bacillales / Q000187:drug effects / Q000254:growth & development; D002733:Chlorophenols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002942:Circular Dichroism; D055808:Drug Discovery; D005285:Fermentation; D006088:Gram-Negative Aerobic Bacteria / Q000187:drug effects / Q000254:growth & development; D055768:Halogenated Diphenyl Ethers / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D054879:Halogenation; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010647:Phenyl Ethers / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D059808:Polyphenols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D012988:Soil Microbiology; D021241:Spectrometry, Mass, Electrospray Ionization; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D002733:Chlorophenols; D055768:Halogenated Diphenyl Ethers; D010647:Phenyl Ethers; D059808:Polyphenols; C021244:polychlorinated diphenyl ethers; C000603853:spiromastol A; C000603854:spiromastol B; C000603855:spiromastol C