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/School / Institute/Centre: | Current - Institute for Life Sciences and the Environment - Centre for Crop Health (24 Mar 2014 -) |
| Faculty/School / Institute/Centre: | Current - Institute for Life Sciences and the Environment - Centre for Crop Health (24 Mar 2014 -) |
| 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 (2008): | 03 Chemical Sciences > 0305 Organic Chemistry > 030599 Organic Chemistry not elsewhere classified |
| Socio-Economic Objectives (2008): | E Expanding Knowledge > 97 Expanding Knowledge > 970107 Expanding Knowledge in the Agricultural and Veterinary Sciences |
| Identification Number or DOI: | https://doi.org/10.1002/chir.22466 |
| URI: | http://eprints.usq.edu.au/id/eprint/29677 |
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