The Chemistry of Antimycin A. II. Degradation Studies<sup>1</sup>

Tener, G. M.; Bumpus, F. Merlin; Dunshee, Bryant R.; Strong, F. M.

doi:10.1021/ja01101a027

Cited by 18 publications

(3 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…27 The structurally related factor I from Streptomyces viridochromogenes and virginiae butanolide A (VB-A) from Streptomyces virginiae exhibit a hydroxylated 2-alkyl group with different stereochemistry at the hydroxy function. , The factor NFX-4 from Streptomyces antibioticus is a butanolide substituted with a 2-alkyl group and, in contrast to the other butanolides, has a 3-hydroxy function and a 4-methyl group . This substitution pattern is also found in the blastmycinones, a large class of butanolides produced by Streptomyces ambofaciens and various other streptomycetes known as degradation products of the fungicidal antimycins. , Gram-negative bacteria use a wide range of species-specific N -acylhomoserine lactones, such as N -(3-oxohexanoyl)- l -homoserine lactone from Vibrio fisheri , for this purpose. , Although these molecules are biosynthetically different from the signaling factors in streptomycetes, the structural resemblence between these two compound classes is intriguing.…”

Section: Resultsmentioning

confidence: 99%

“…30 This substitution pattern is also found in the blastmycinones, a large class of butanolides produced by Streptomyces ambofaciens and various other streptomycetes known as degradation products of the fungicidal antimycins. 4,31 Gram-negative bacteria use a wide range of species-specific N-acylhomoserine lactones, such as N-(3-oxohexanoyl)-L-homoserine lactone from Vibrio f isheri, for this purpose. 32,33 Although these molecules are biosynthetically different from the signaling factors in streptomycetes, the structural resemblence between these two compound classes is intriguing.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

See 1 more Smart Citation

The Scent of Bacteria: Headspace Analysis for the Discovery of Natural Products

2012

View full text Add to dashboard Cite

Volatile compounds released by 50 bacterial strains, 45 of them actinobacteria in addition to three chloroflexi and two myxobacteria, have been collected by use of a closed-loop stripping apparatus, and the obtained headspace extracts have been analyzed by GC-MS. Excluding terpenes that have recently been published elsewhere, 254 compounds from all kinds of compound classes have been identified. For unambiguous compound identification several reference compounds have been synthesized. Among the detected volatiles 12 new natural products have been found, in addition to mellein, which was released by Saccharopolyspora erythraea. The iterative PKS for this compound has recently been identified by in vitro experiments, but mellein production in S. erythraea has never been reported before. These examples demonstrate that headspace analysis is an important tool for the discovery of natural products that may be overlooked using conventional techniques. The method is also useful for feeding experiments with isotopically labeled precursors and was applied to investigate the biosynthesis of the unusual nitrogen compound 1-nitro-2-methylpropane, which arises from valine. Furthermore, several streptomycetes emitted compounds that were previously recognized as insect pheromones, thus questioning if bacterial symbionts are involved in insect communication.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

The Scent of Bacteria: Headspace Analysis for the Discovery of Natural Products

2012

View full text Add to dashboard Cite

show abstract

“…Interestingly, the study of the antimycin cluster in S. ambofaciens ATCC 23877 revealed that it was also responsible for the presence of the volatile compounds blastmycinones and butenolides [62]. It was known for a long time that antimycins can easily undergo base-catalysed degradation to blastmycinone derivatives and to N-(3-formamido-2-hydroxybenzoyl)-l-threonine [66][67][68]. In addition, blastmycinones can form either butanolide compounds by deacylation or butenolide volatiles by elimination of a carboxylic acid [18].…”

Section: Antimycins and Related Volatilesmentioning

confidence: 99%

Genome mining of Streptomyces ambofaciens

Aigle

Lautru

Spiteller

et al. 2014

Journal of Industrial Microbiology and Biotechnology

View full text Add to dashboard Cite

Since the discovery of the streptomycin produced by Streptomyces griseus in the middle of the last century, members of this bacterial genus have been largely exploited for the production of secondary metabolites with wide uses in medicine and in agriculture. They have even been recognized as one of the most prolific producers of natural products among microorganisms. With the onset of the genomic era, it became evident that these microorganisms still represent a major source for the discovery of novel secondary metabolites. This was highlighted with the complete genome sequencing of Streptomyces coelicolor A3(2) which revealed an unexpected potential of this organism to synthesize natural products undetected until then by classical screening methods. Since then, analysis of sequenced genomes from numerous Streptomyces species has shown that a single species can carry more than 30 secondary metabolite gene clusters, reinforcing the idea that the biosynthetic potential of this bacterial genus is far from being fully exploited. This review highlights our knowledge on the potential of Streptomyces ambofaciens ATCC 23877 to synthesize natural products. This industrial strain was known for decades to only produce the drug spiramycin and another antibacterial compound, congocidine. Mining of its genome allowed the identification of 23 clusters potentially involved in the production of other secondary metabolites. Studies of some of these clusters resulted in the characterization of novel compounds and of previously known compounds but never characterized in this Streptomyces species. In addition, genome mining revealed that secondary metabolite gene clusters of phylogenetically closely related Streptomyces are mainly species-specific.

show abstract