Novel Oxidized Derivatives of Antifungal Pyrrolnitrin from the Bacterium Burkholderia cepacia K87

Sultan, Zakir; Park, Kyungseok; Lee, Sang Yeob; Park, Jung Kon; Varughese, Titto; Moon, Surk‐Sik

doi:10.1038/ja.2008.58

Cited by 23 publications

(15 citation statements)

References 19 publications

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“…This molecule was thoroughly studied and presents a molecular mass of 256 Da (Hwang et al 2002). The mass spectrometric characterization of Bc-255 and Bc-257 proved that they were not derived from the PRN or its derivatives (Sultan et al 2008). This result was also confirmed by the NMR analysis which showed that these two antifungal molecules belonged to the quinolone family (Diggle et al 2006;Vial et al 2008) and enabled us to determine their chemical structure.…”

Section: Discussionmentioning

confidence: 64%

Correlation between synthesis variation of 2-alkylquinolones and the antifungal activity of a Burkholderia cepacia strain collection

Kilani-Feki

Zouari

Culioli

et al. 2011

World J Microbiol Biotechnol

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Twenty epiphytic and rhizospheric bacterial strains harbouring strong antifungal activities were isolated from the Tunisian environment. This group of bacteria was identified as Burkholderia cepacia genomovar I using 16S rDNA and recA fragment gene sequence analyses for two selected strains and RFLP technique for the eighteen other ones. This identification did not show variability between isolates despite the significant differences in the antifungal activities of their culture supernatant and the organic crude extract against Aspergillus niger and other phytopathogenic fungi. Chromatographic and mass spectrometric analyses of these extracts allowed us to confirm the difference between strains of the group. Their metabolic production showed differences in term of contents and quantities of secreted molecules, particularly those which were identified to be involved in the antifungal activities. Two metabolites, named Bc-255 and Bc-257 secreted by the entire group at different amounts, have been purified and tested separately against A. niger. Bc-255 showed an activity twice as high as those shown by Bc-257. The structural characterization of these two compounds by mass spectrometry and nuclear magnetic resonance spectroscopy allowed their identification as two analogous 2-alkylquinolones with only one difference at the alkyl chain.

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Section: Discussionmentioning

confidence: 64%

Correlation between synthesis variation of 2-alkylquinolones and the antifungal activity of a Burkholderia cepacia strain collection

Kilani-Feki

Zouari

Culioli

et al. 2011

World J Microbiol Biotechnol

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“…In addition, we do not exclude the possibility that other molecules beyond volatile compounds could be also involved in the actual morphological changes. In this regard, a recent screening of antifungal active compounds from B. cepacia K87, identified pyrrolnitrin and two derivatives as antifungal compounds; whereas, in B. ambifaria a mixture of lipopeptides, where the burkholdines have been characterized, are involved in the antifungal activity 20 , 21 …”

Section: Resultsmentioning

confidence: 99%

Identification of volatile compounds produced by the bacteriumBurkholderia tropicathat inhibit the growth of fungal pathogens

et al. 2013

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It has been documented that bacteria from the Burkholderia genera produce different kinds of compounds that inhibit plant pathogens, however in Burkholderia tropica, an endophytic diazotrophic and phosphate-solubilizing bacterium isolated from a wide diversity of plants, the capacity to produce antifungal compounds has not been evaluated. In order to expand our knowledge about Burkholderia tropica as a potential biological control agent, we analyzed 15 different strains of this bacterium to evaluate their capacities to inhibit the growth of four phytopathogenic fungi, Colletotrichum gloeosporioides, Fusarium culmorum, Fusarium oxysporum and Sclerotium rolffsi. Diverse analytical techniques, including plant root protection and dish plate growth assays and gas chromatography-mass spectroscopy showed that the fungal growth inhibition was intimately associated with the volatile compounds produced by B. tropica and, in particular, two bacterial strains (MTo293 and TTe203) exhibited the highest radial mycelial growth inhibition. Morphological changes associated with these compounds, such as disruption of fungal hyphae, were identified by using photomicrographic analysis. By using gas chromatography-mass spectroscopy technique, 18 volatile compounds involved in the growth inhibition mechanism were identified, including α-pinene and limonene. In addition, we found a high proportion of bacterial strains that produced siderophores during growth with different carbon sources, such as alanine and glutamic acid; however, their roles in the antagonism mechanism remain unclear.

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“…The broth of B. cepacia K87 (10 L) was extracted with MeOH [3]. The methanolic extract was subjected to a series of chromatography (reversed-phase C-18 flash column chromatography followed by C-18 MPLC and HPLC).…”

Section: Resultsmentioning

confidence: 99%

“…Antimicrobial and cytotoxicity assays were carried out according to the methods described in the literatures [3,17,18]. …”

Section: Antimicrobial and Cytotoxicity Assaysmentioning

confidence: 99%

“…In continuation of our research for identification of plant growth promoting and antimicrobial compounds from the microbes, we reported two new degraded intermediates of antifungal pyrrolnitrin as 3-chloro-4-(3-chloro-2-nitrophenyl)-5-methoxy-3-pyrrolin-2-one and 4-chloro-3-(3-chloro-2-nitrophenyl)-5-methoxy-3-pyrrolin-2-one from soil bacterium B. cepacia K87 [3]. From the methanolic extract of the bacterium, marginally antifungal three phthalate derivatives, dibutyl phthalate (1), dioctyl phthalate (2), and phthalate ester of alkylated 9-hydroxynonanoic acid (3) were isolated.…”

Section: Introductionmentioning

confidence: 99%

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Natural Phthalate Derivatives from the Bacterium <i>Burkholderia cepacia</i> K87

Sultan¹,

Moon

Park

2009

J. Sci. Res.

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In continuation of our screening of antifungal active compounds from the fermentation extracts of soil borne bacteria Burkholderia cepacia K87 afforded three phthalate derivatives, dibutyl phthalate (1), dioctyl phthalate (2), and phthalate ester of alkylated 9-hydroxynonanoic acid (3). Compound 3 was reported first time. These phthalate derivatives were found to be marginally active or inactive against a number of bacteria and fungi.

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Novel Oxidized Derivatives of Antifungal Pyrrolnitrin from the Bacterium Burkholderia cepacia K87

Cited by 23 publications

References 19 publications

Correlation between synthesis variation of 2-alkylquinolones and the antifungal activity of a Burkholderia cepacia strain collection

Correlation between synthesis variation of 2-alkylquinolones and the antifungal activity of a Burkholderia cepacia strain collection

Identification of volatile compounds produced by the bacteriumBurkholderia tropicathat inhibit the growth of fungal pathogens

Natural Phthalate Derivatives from the Bacterium <i>Burkholderia cepacia</i> K87

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