6-Hydroxy-5-nitrobenzo[d]oxazol-2(3H)-one—A degradable derivative of natural 6-Hydroxybenzoxazolin-2(3H)-one produced by Pantoea ananatis

Communicative & Integrative Biology

Ulrich Disko¹  Diana Hofmann¹  Oliver Schackow²  Dieter Sicker²  Lothar Hennig²  Marina Ventura³  Margot Schulz³  Kateryna Basyuk³ 

[1] IBG-3: Agrosphäre, Forschungszentrum Jülich GmbH;Institut für Organische Chemie, Universität Leipzig;University of Bonn;

关键词: Abutilon theophrasti L.;    allelopathy;    nitro-aromatic compound;    Pantoea ananatis;    peroxidase;    root surface;    6-hydroxybenzoxazolin-2(3H)-one;   

DOI  :  10.1080/19420889.2017.1302633

来源: DOAJ

【 摘 要 】

Pantoea ananatis is a bacterium associated with other microorganisms on Abutilon theophrasti Medik. roots. It converts 6-hydroxybenzoxazolin-2(3H)-one (BOA-6-OH), a hydroxylated derivative of the allelochemical benzoxazolin-2(3H)-one, into 6-hydroxy-5-nitrobenzo[d]oxazol-2(3H)-one. The compound was identified by NMR and mass spectrometric methods. In vitro synthesis succeeded with Pantoea protein, with isolated proteins from the Abutilon root surface or with horseradish peroxidase in the presence of nitrite and H2O2. Nitro-BOA-6-OH is completely degraded further by Pantoea ananatis and Abutilon root surface proteins. Under laboratory conditions, 6-hydroxy-5-nitrobenzo[d]oxazol-2(3H)-one inhibits Lepidium sativum seedling growth whereas Abutilon theophrasti is much less affected. Although biodegradable, an agricultural use of 6-hydroxy-5-nitrobenzo[d]oxazol-2(3H)-one is undesirable because of the high toxicity of nitro aromatic compounds to mammals.

【 授权许可】

Unknown