Diplopyrone, a new phytotoxic tetrahydropyranpyran-2-one produced by Diplodia mutila, a fungus pathogen of cork oak.

Abstract

A new phytotoxic monosubstituted tetrahydropyranpyran-2-one, named diplopyrone (1), was isolated from the liquid culture filtrates of Diplodia mutila, a plant pathogenic fungus causing a form of canker disease of cork oak (Quercus suber). Diplopyrone was characterized, using spectroscopic and chemical methods, as 6-[(1S)-1-hydroxyethyl]-2,4a,6,8a-tetrahydropyran[3,2-b]pyran-2-one. The absolute stereochemistry of the chiral secondary hydroxylated carbon (C-9), determined by application of Mosher's method, proved to be S. Diplopyrone assayed at a 0.01-0.1 mg/mL concentration range caused necrosis and wilting on cork oak cuttings. On a nonhost plant, tomato, diplopyrone caused brown discoloration or stewing on the stem.

• Authors: Antonio Evidente, Lucia Maddau, Emanuela Spanu, Antonio Franceschini, Silvia Lazzaroni, Andrea Motta
• Journal: Journal of natural products (J Nat Prod) Vol. 66 Issue 2 Pg. 313-5 (Feb 2003) ISSN: 0163-3864 [Print] United States
• PMID: 12608876 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Mycotoxins
• Pyrones
• diplopyrone

Topics

• Italy
• Solanum lycopersicum (drug effects)
• Mitosporic Fungi (pathogenicity)
• Molecular Structure
• Mycotoxins (toxicity)
• Nuclear Magnetic Resonance, Biomolecular
• Plant Diseases (microbiology)
• Plant Roots (chemistry)
• Pyrones (chemistry, toxicity)
• Quercus (chemistry)
• Stereoisomerism