Isolation and Structure Elucidation of Pentahydroxyscirpene, a Trichothecene Fusarium Mycotoxin

• Published in: Journal of natural products (Washington, D.C.) Vol. 77; no. 1; pp. 188 - 192
• Main Authors: Fruhmann, Philipp, Mikula, Hannes, Wiesenberger, Gerlinde, Varga, Elisabeth, Lumpi, Daniel, Stöger, Berthold, Häubl, Georg, Lemmens, Marc, Berthiller, Franz, Krska, Rudolf, Adam, Gerhard, Hametner, Christian, Fröhlich, Johannes
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 24.01.2014; Amer Chemical Soc
• Subjects: Chemistry, Medicinal; Crystallography, X-Ray; Fusarium; Fusarium - chemistry; Life Sciences & Biomedicine; Molecular Conformation; Molecular Structure; Mycotoxins - chemistry; Mycotoxins - isolation & purification; Mycotoxins - pharmacology; Nuclear Magnetic Resonance, Biomolecular; Oryza - microbiology; Oryza sativa; Pharmacology & Pharmacy; Plant Sciences; Protein Synthesis Inhibitors - chemistry; Protein Synthesis Inhibitors - isolation & purification; Protein Synthesis Inhibitors - pharmacology; Science & Technology; Trichothecenes - chemistry; Trichothecenes - isolation & purification; Trichothecenes - pharmacology; TOXICOLOGY
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np4008365

Pentahydroxyscirpene, a novel trichothecene-type compound, was isolated from Fusarium-inoculated rice. The structure of pentahydroxyscirpene was elucidated by 1D and 2D NMR spectroscopy and X-ray single-crystal diffraction. The conformation in solution was determined by NOESY experiments supported by quantum chemical calculations. In vitro toxicity tests showed that pentahydroxyscirpene inhibits protein synthesis as do other trichothecenes.