Caryoynencins, potent antibiotics from a plant pathogen

Kusumi, Takenori; Ohtani, Ikuko I.; Nishiyama, Koushi; Kakisawa, Hiroshi

doi:10.1016/s0040-4039(00)96437-2

Cited by 50 publications

(44 citation statements)

References 2 publications

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“…3c). Unsurprisingly, caryoynencin was not detected in the extracts, since this highly reactive compound is known to degrade rapidly1220. To shed further light on the functional role of the bacterial metabolites, we assessed the activity of the compounds against a number of entomopathogenic microorganisms in vitro .…”

Section: Resultsmentioning

confidence: 99%

Antibiotic-producing symbionts dynamically transition between plant pathogenicity and insect-defensive mutualism

et al. 2017

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Pathogenic and mutualistic bacteria associated with eukaryotic hosts often lack distinctive genomic features, suggesting regular transitions between these lifestyles. Here we present evidence supporting a dynamic transition from plant pathogenicity to insect-defensive mutualism in symbiotic Burkholderia gladioli bacteria. In a group of herbivorous beetles, these symbionts protect the vulnerable egg stage against detrimental microbes. The production of a blend of antibiotics by B. gladioli, including toxoflavin, caryoynencin and two new antimicrobial compounds, the macrolide lagriene and the isothiocyanate sinapigladioside, likely mediate this defensive role. In addition to vertical transmission, these insect symbionts can be exchanged via the host plant and retain the ability to initiate systemic plant infection at the expense of the plant's fitness. Our findings provide a paradigm for the transition between pathogenic and mutualistic lifestyles and shed light on the evolution and chemical ecology of this defensive mutualism.

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Section: Resultsmentioning

confidence: 99%

Antibiotic-producing symbionts dynamically transition between plant pathogenicity and insect-defensive mutualism

et al. 2017

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“…calichensis (Ahlert et al, 2002;Belecki et al, 2009). Other examples of bacterially produced polyynes are cepacin A and B from Burkholderia cepacia (Parker et al, 1984) and caryoynencin A-C from Burkholderia caryophylli (Kusumi et al, 1987;Yamaguchi et al, 1995). The predicted UV maxima for cepacins (226, 236, 294 and 309 nm) and caryoynencins (273,290,311,331,356 and 382 nm), based on Bohlmann and colleagues (1973), are different from those that we observed for collimomycins, suggesting that the latter represent a structure that is different from that of previously described bacterial polyynes.…”

Section: Discussionmentioning

confidence: 99%

Biosynthetic genes and activity spectrum of antifungal polyynes from Collimonas fungivorans Ter331

Fritsche

Berg

Boer

et al. 2014

Environmental Microbiology

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Summary The antifungal activity of bacteria from the genus Collimonas has been well documented, but the chemistry and gene functions that underlie this phenotype are still poorly understood. Screening of a random plasposon insertion library of Collimonas fungivorans Ter331 for loss‐of‐function mutants revealed the importance of gene cluster K, which is annotated to code for the biosynthesis of a secondary metabolite and which features genes for fatty acid desaturases and polyketide synthases. Mutants in gene cluster K had lost the ability to inhibit hyphal growth of the fungus Aspergillus niger and were no longer able to produce and secrete several metabolites that after extraction and partial purification from wildtype strain Ter331 were shown to share a putative ene‐triyne moiety. Some but not all of these metabolites were able to inhibit growth of A. niger, indicating functional variation within this group of Collimonas‐produced polyyne‐like ‘collimomycins’. Polymerase chain reaction analysis of isolates representing different Collimonas species indicated that the possession of cluster K genes correlated positively with antifungal ability, further strengthening the notion that this cluster is involved in collimomycin production. We discuss our findings in the context of other bacterially produced polyynes and the potential use of collimomycins for the control of harmful fungi.

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“…The extremely unstable terminal tetrayne caryoynencin ( 244 , Scheme ) has been isolated from liquid cultures of the plant pathogen Pseudomonas caryophylli , and has demonstrated antimicrobial activity against both Gram‐positive and Gram‐negative bacteria 183. Yamaguchi et al have reported the synthesis of 244 , as well as a number of tetrayne analogues (not shown) 184.…”

Section: Tetraynes From Bacteriamentioning

confidence: 99%

Synthesis of Naturally Occurring Polyynes

2006

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Over the past fifty years, hundreds of polyyne compounds have been isolated from nature. These often unstable molecules are found in sources as common as garden vegetables and as obscure as bacterial cultures. Naturally occurring polyynes feature a wide range of structural diversity and display an equally broad array of biological properties. Early synthetic efforts relied primarily on Cu-catalyzed, oxidative acetylenic homo- and heterocoupling reactions to assemble the polyyne framework. The past 25 years, however, have witnessed a renaissance in the field of polyyne natural product synthesis: transition-metal-catalyzed alkynylation reactions and asymmetric transformations have combined to substantially expand access to natural polyynes. This Review recounts these synthetic achievements and also highlights both the natural source(s) and biological relevance for many of these compounds.

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Caryoynencins, potent antibiotics from a plant pathogen

Cited by 50 publications

References 2 publications

Antibiotic-producing symbionts dynamically transition between plant pathogenicity and insect-defensive mutualism

Antibiotic-producing symbionts dynamically transition between plant pathogenicity and insect-defensive mutualism

Biosynthetic genes and activity spectrum of antifungal polyynes from Collimonas fungivorans Ter331

Synthesis of Naturally Occurring Polyynes

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