Detection of a Toxic Methylated Derivative of Phomopsin A Produced by the Legume-Infesting Fungus Diaporthe toxica

• Published in: Journal of natural products (Washington, D.C.) Vol. 80; no. 6; pp. 1930 - 1934
• Main Authors: Schloß, Svenja, Hackl, Thomas, Herz, Corinna, Lamy, Evelyn, Koch, Matthias, Rohn, Sascha, Maul, Ronald
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 23.06.2017; Amer Chemical Soc
• Subjects: Animals; Ascomycota - chemistry; Chemistry, Medicinal; cytotoxicity; Diaporthe; Fabaceae - microbiology; fungi; Hep G2 Cells - drug effects; human cell lines; Humans; Life Sciences & Biomedicine; liver diseases; Lupinus; Molecular Structure; mycotoxins; Mycotoxins - analysis; Mycotoxins - chemistry; nuclear magnetic resonance spectroscopy; Nuclear Magnetic Resonance, Biomolecular; Pharmacology & Pharmacy; Plant Sciences; Science & Technology; secondary metabolites; seeds; Seeds - chemistry; Sheep; HEXAPEPTIDE MYCOTOXIN; LUPIN; LEPTOSTROMIFORMIS; STRUCTURE ELUCIDATION; LC-MS/MS METHOD; FOOD
• ISSN: 0163-3864; 1520-6025; 1520-6025
• DOI: 10.1021/acs.jnatprod.6b00662

Phomopsin A (PHO-A), produced by the fungus Diaporthe toxica, is a mycotoxin known to be responsible for fatal liver disease of lupin-fed sheep. The full spectrum of the toxic secondary metabolites produced by D. toxica is still unknown. PHO-A and the naturally occurring derivatives B–E have been subject to several studies to reveal their structures as well as chemical and toxicological properties. In this work, a methylated derivative (1) of PHO-A isolated from lupin seeds inoculated with D. toxica is described. It was characterized by high-resolution mass and NMR data and shown to be the N-methylated derivative of PHO-A. 1 is cytotoxic against HepG2 cells.