title: Spiromastixones A-O, antibacterial chlorodepsidones from a deep-sea-derived Spiromastix sp. fungus.
abstract: Fifteen new depsidone-based analogues named spiromastixones A-O (1-15) were isolated from the fermentation broth of a deep-sea Spiromastix sp. fungus. Their structures were elucidated on the basis of extensive NMR and mass spectroscopic analysis in association with chemical conversion. Spiromastixones A-O are classified into two subtypes based on the orientation of ring C relative to ring A, while the n-propyl substituents on rings A and C are rarely seen in natural products. Most analogues are substituted by various numbers of chlorine atoms. All compounds exhibited significant inhibition against Gram-positive bacteria including Staphylococcus aureus, Bacillus thuringiensis, and Bacillus subtilis with MIC values ranging from 0.125 to 8.0 μg/mL. In addition, compounds 6-10 displayed potent inhibitory effects against methicillin-resistant bacterial strains of S. aureus (MRSA) and S. epidermidis (MRSE), while 10 also inhibited the growth of the vancomycin-resistant bacteria Enterococcus faecalis and E. faecium (VRE). The structure-activity relationships are discussed.
authors.affiliation: State Key Laboratory of Natural and Biomimetic Drugs, Peking University , Beijing, 100191, People's Republic of China.
authors.forename: Siwen
authors.initials: S
authors.lastname: Niu
authors.forename: Dong
authors.initials: D
authors.lastname: Liu
authors.forename: Xinxin
authors.initials: X
authors.lastname: Hu
authors.forename: Peter
authors.initials: P
authors.lastname: Proksch
authors.forename: Zhongzhe
authors.initials: Z
authors.lastname: Shao
authors.forename: Wenhan
authors.initials: W
authors.lastname: Lin
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D053630:Depsides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013293:Enterococcus faecalis / Q000187:drug effects; D005658:Fungi / Q000737:chemistry*; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008712:Methicillin / Q000494:pharmacology; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009792:Oceans and Seas; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship; D014640:Vancomycin / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D053630:Depsides; D006575:Heterocyclic Compounds, 3-Ring; D006843:Hydrocarbons, Chlorinated; D007783:Lactones; C000875:depsidone; D014640:Vancomycin; D008712:Methicillin