Structure and absolute configuration of kongiidiazadione, a new Phytotoxic 3-Substituted-5-Diazenylcyclopentendione Produced by Diaporthe Kongii

Marco Evidente, Angela Boari, Stefania Vergura, Alessio Cimmino, Maurizio Vurro, Gavin Ash, Stefano Superchi, Antonio Evidente

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

A new 3-substituted-5-diazenylcyclopentendione named kongiidiazadione was isolated from culture filtrates of Diaporthe kongii, associated with stem cankers on sunflower in Australia. Kongiidiazadione was characterized by spectroscopic (essentially nuclear magnetic resonance [NMR] and high-resolution, electrospray ionization, mass spectrometry [HRESIMS]) methods as (-)-5-diazenyl-3-hydroxymethyl-cyclopent-3-en-1,2-dione. The stereochemistry of the diazenyl group was determined by IR spectroscopy, while the (R) absolute configuration at C(5) was assigned by computational analysis of its electronic circular dichroism (ECD) spectrum. When assayed on leaf disks of different plant species at 5 mM, the kongiidiazadione had a differential impact, causing clear necrosis, in particular to Helianthus annuus. Moreover, kongiidiazadione proved to have a weak antibacterial activity against gram-positive Bacillus amyloliquefaciens.
Original languageEnglish
Pages (from-to)557-562
Number of pages6
JournalChirality
Volume27
Issue number9
DOIs
Publication statusPublished - Sep 2015

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