Structure and Absolute Configuration of Kongiidiazadione, a NewPhytotoxic 3-Substituted-5-Diazenylcyclopentendione Produced by Diaporthe Kongii
Article
Article Title | Structure and Absolute Configuration of Kongiidiazadione, a NewPhytotoxic 3-Substituted-5-Diazenylcyclopentendione Produced by Diaporthe Kongii |
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ERA Journal ID | 1571 |
Article Category | Article |
Authors | Evidente, Marco (Author), Boari, Angela (Author), Vergura, Stefania (Author), Cimmino, Alessio (Author), Vurro, Maurizio (Author), Ash, Gavin (Author), Superchi, Stefano (Author) and Evidente, Antonio (Author) |
Journal Title | Chirality: the pharmacological, biological, and chemical consequences of molecular asymmetry |
Journal Citation | 27 (9), pp. 557-562 |
Number of Pages | 6 |
Year | Sep 2015 |
Place of Publication | United States |
ISSN | 0899-0042 |
1520-636X | |
Digital Object Identifier (DOI) | https://doi.org/10.1002/chir.22466 |
Web Address (URL) | https://onlinelibrary.wiley.com/doi/10.1002/chir.22466 |
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. |
Keywords | Carthamus lanatus; Diaporthe kongii; phytotoxin; kongiidiazadione; electronic circular dichroism; absolute configuration |
Contains Sensitive Content | Does not contain sensitive content |
ANZSRC Field of Research 2020 | 340599. Organic chemistry not elsewhere classified |
Public Notes | Files associated with this item cannot be displayed due to copyright restrictions. |
Byline Affiliations | University of Naples Federico II, Italy |
Institute of Sciences and Food Production, Italy | |
University of Basilicata, Italy | |
Charles Sturt University | |
Institution of Origin | University of Southern Queensland |
https://research.usq.edu.au/item/q394x/structure-and-absolute-configuration-of-kongiidiazadione-a-newphytotoxic-3-substituted-5-diazenylcyclopentendione-produced-by-diaporthe-kongii
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