Journal of natural products (Washington, D.C.), 2009-02, Vol.72 (2), p.248-252
2009
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Details
- Autor(en) / Beteiligte
- Titel
- Glionitrin A, an Antibiotic−Antitumor Metabolite Derived from Competitive Interaction between Abandoned Mine Microbes
- Ist Teil von
- Journal of natural products (Washington, D.C.), 2009-02, Vol.72 (2), p.248-252
- Ort / Verlag
- Northbrook, IL: American Chemical Society and American Society of Pharmacognosy
- Erscheinungsjahr
- 2009
- Quelle
- MEDLINE
- Beschreibungen/Notizen
- The nutrient conditions present in abandoned coal mine drainages create an extreme environment where defensive and offensive microbial interactions could be critical for survival and fitness. Coculture of a mine drainage-derived Sphingomonas bacterial strain, KMK-001, and a mine drainage-derived Aspergillus fumigatus fungal strain, KMC-901, resulted in isolation of a new diketopiperazine disulfide, glionitrin A (1). Compound 1 was not detected in monoculture broths of KMK-001 or KMC-901. The structure of 1, a (3S,10aS) diketopiperazine disulfide containing a nitro aromatic ring, was based on analysis of MS, NMR, and circular dichroism spectra and confirmed by X-ray crystal data. Glionitrin A displayed significant antibiotic activity against a series of microbes including methicillin-resistant Staphylococcus aureus. An in vitro MTT cytotoxicity assay revealed that 1 had potent submicromolar cytotoxic activity against four human cancer cell lines: HCT-116, A549, AGS, and DU145. The results provide further evidence that microbial coculture can produce novel biologically relevant molecules.
- Sprache
- Englisch
- Identifikatoren
- ISSN: 0163-3864eISSN: 1520-6025DOI: 10.1021/np800606eTitel-ID: cdi_osti_scitechconnect_21162076
- Format
- –
- Schlagworte
- 01 COAL, LIGNITE, AND PEAT, ACID MINE DRAINAGE, Anti-Bacterial Agents - chemistry, Anti-Bacterial Agents - isolation & purification, Anti-Bacterial Agents - pharmacology, antibacterial properties, ANTIBIOTICS, Antibiotics (antibacterial agents, antifungal agents), Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents, anticarcinogenic activity, Antineoplastic Agents - chemistry, Antineoplastic Agents - isolation & purification, Antineoplastic Agents - pharmacology, Applied microbiology, ASPERGILLUS, Aspergillus - chemistry, Aspergillus - metabolism, Aspergillus fumigatus, BACTERIA, Biological and medical sciences, chemical structure, Chemotherapic agents, coal mine, COAL MINING, coculture, Crystallography, X-Ray, cytotoxicity, dehydrogliotoxin, diketopiperazine disulfide, Diketopiperazines - chemistry, Diketopiperazines - isolation & purification, Diketopiperazines - pharmacology, disulfide bonds, Drug Screening Assays, Antitumor, Fundamental and applied biological sciences. Psychology, FUNGI, glionitrin, gliotoxin, HCT116 Cells, human diseases, Humans, medicinal properties, Methicillin-Resistant Staphylococcus aureus - drug effects, Microbiology, MICROORGANISMS, Molecular Conformation, Molecular Structure, NUTRIENTS, PIPERAZINES, secondary metabolites, spectral analysis, Sphingomonas, Sphingomonas - chemistry, Sphingomonas - metabolism, Staphylococcus aureus, stereochemistry, SULFIDES