Xanthepinone, an Antimicrobial Polyketide from a Soil Fungus Closely Related to Phoma medicaginis

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2009-10, Vol.72 (10), p.1905-1907
• Main Authors: Liermann, Johannes C, Kolshorn, Heinz, Opatz, Till, Thines, Eckhard, Anke, Heidrun
• Format: Article
• Language: English
• Subjects: Antifungal Agents - chemistry; Antifungal Agents - isolation & purification; Antifungal Agents - pharmacology; antifungal properties; Ascomycota - chemistry; Biological and medical sciences; Botrytis - drug effects; Botrytis cinerea; chemical structure; Crystallography, X-Ray; General pharmacology; HeLa Cells; Heterocyclic Compounds, 3-Ring - chemistry; Heterocyclic Compounds, 3-Ring - isolation & purification; Heterocyclic Compounds, 3-Ring - pharmacology; Humans; Magnaporthe - drug effects; Magnaporthe grisea; Medical sciences; Microbial Sensitivity Tests; Molecular Conformation; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Phoma; Phoma medicaginis; Phytophthora infestans; Phytophthora infestans - drug effects; plant pathogenic fungi; polyketides; soil fungi; spectral analysis; xanthepinone
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np9005234

The isolation, biological characterization, and structure elucidation of xanthepinone, a novel antifungal metabolite isolated from the broth of submerged cultures of a soil fungus, are described. Xanthepinone inhibits the conidial germination of Magnaporthe grisea (2 μg/mL), Phytophthora infestans (5 μg/mL), and Botrytis cinerea (10 μg/mL) while showing only weak antibacterial activity; cytotoxicity was not observed up to 50 μg/mL. Molecular taxonomy revealed that the producing strain is close to species in the genus Phoma as well as to uncultured soil fungi and endophytes.