4-Formylaminooxyvinylglycine, an Herbicidal Germination-Arrest Factor from Pseudomonas Rhizosphere Bacteria

Abstract

A new oxyvinylglycine has been identified as a naturally occurring herbicide that irreversibly arrests germination of the seeds of grassy weeds, such as annual bluegrass (Poa annua), without significantly affecting the growth of established grass seedlings and mature plants or germination of the seeds of broadleaf plant species (dicots). Previously, Pseudomonas fluorescens WH6 and over twenty other rhizosphere bacteria were isolated and selected for their ability to arrest germination of P. annua seeds. The Germination-Arrest Factor (GAF, 1) responsible for this developmentally specific herbicidal action has now been isolated from the culture filtrate of P. fluorescens WH6. Purification of this highly polar, low molecular weight natural product allowed its structure to be assigned as 4-formylaminooxy-l-vinylglycine based on NMR spectroscopic and mass spectrometric data, in combination with d/l-amino acid oxidase reactions to establish the absolute configuration. Assay results for P. annua inhibition by related compounds known to regulate plant growth are presented, and a cellular target for 1 is proposed. Furthermore, using bioassays, TLC, and capillary NMR spectroscopy, it has been shown that GAF (1) is secreted by all other herbicidally-active rhizosphere bacteria in our collection.

Indole-3-acetic acid (IAA) producing Pseudomonas isolates inhibit seed germination and α-amylase activity in durum wheat (Triticum turgidum L.)

“…In some reports, inoculation with bacteria has promoted seed germination and rate (Ashrafuzzaman et al, 2009;Selvakumar et al, 2009;Zarrin et al, 2009;Noumavo et al, 2013), while in some other reports it has been found to decrease seed germination (Banowetz et al, 2008;McPhail et al, 2010). For example, Selvakuma et al (2009) reported that P. fragi CS11RH1, an IAA-producing strain, significantly increased the germination percentage and rate, plant biomass and nutrient uptake of wheat seedlings.…”

“…For example, some of the bacteria in this group are known to be pathogenic (Hirano & Upper, 2000), while others are known to be involved in disease suppression (Halgren et al, 2011). In addition, some members of this group of bacteria appear to increase seed germination (Selvakumar et al, 2009), while others exert inhibitory effects on seed germination (McPhail et al, 2010;Lee et al, 2013). Germination arrest factors (GAFs) have been the subject of increased research in recent years.…”

“…The 2 of seed germination in a wide range of graminaceous species (Banowetz et al, 2008). For example, the compounds 4-formylaminooxyvinylglycine (FVG) (McPhail et al, 2010) and L-2-amino-4-methoxy-trans-3-butenoic acid (AMB) (Lee et al, 2013) are two GAFs produced by Pseudomonas species. However, there is a gap in knowledge regarding the impact of GAFs on wheat seed germination, in general, and on durum wheat (Triticum turgidum L.) seed, in particular.…”

Medicinal plants with phytotoxic activity harbour endophytic bacteria with plant growth inhibitory properties

“…57. In earlier studies, Brimecombe et al (2007) and McPhail et al (2010) also observed an inhibition of plant growth by plant-associated bacteria. Several bacterial metabolites such as phytotoxins, cyanide and nonvolatile compound can inhibit plant growth (Banowetz et al 2008).…”

Pseudomonas fluorescens SBW25 produces furanomycin, a non-proteinogenic amino acid with selective antimicrobial properties

“…This compound, which we termed a Germination-Arrest Factor (GAF), selectively and irreversibly arrests the germination of a large number of graminaceous species, including a number of invasive grassy weeds [10]. We identified GAF as the non-proteinogenic amino acid 4-formylaminooxyvinylglycine (FVG, L-2-amino-4-formylaminooxy- trans- 3-butenoic acid) [12]. FVG was subsequently shown to also have selective antimicrobial activity against a few strains of bacteria (13), including Erwinia amylovora , the bacterial plant pathogen that is the causal agent of the disease of orchard crops known as fireblight.…”