Structure and absolute configuration of kongiidiazadione, a new phytotoxic 3-substituted-5-diazenylcyclopentendione produced by Diaporthe kongii

Evidente, Marco and Boari, Angela and Vergura, Stefania and Cimmino, Alessio and Vurro, Maurizio and Ash, Gavin and Superchi, Stefano and Evidente, Antonio (2015) Structure and absolute configuration of kongiidiazadione, a new phytotoxic 3-substituted-5-diazenylcyclopentendione produced by Diaporthe kongii. Chirality , 27 (9). pp. 557-562. ISSN 0899-0042

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.


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Item Type: Article (Commonwealth Reporting Category C)
Refereed: Yes
Item Status: Live Archive
Additional Information: Files associated with this item cannot be displayed due to copyright restrictions.
Faculty / Department / School: Current - Faculty of Health, Engineering and Sciences - School of Agricultural, Computational and Environmental Sciences
Date Deposited: 01 Sep 2016 05:46
Last Modified: 04 Jun 2018 06:27
Uncontrolled Keywords: absolute configuration; Carthamus lanatus; Diaporthe kongii; electronic circular dichroism; kongiidiazadione; phytotoxin
Fields of Research : 03 Chemical Sciences > 0305 Organic Chemistry > 030599 Organic Chemistry not elsewhere classified
Socio-Economic Objective: E Expanding Knowledge > 97 Expanding Knowledge > 970107 Expanding Knowledge in the Agricultural and Veterinary Sciences
Identification Number or DOI: 10.1002/chir.22466
URI: http://eprints.usq.edu.au/id/eprint/29677

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