Production of butyrolactone autoregulators by Streptomyces coelicolor A3(2)

Kawabuchi, Masahiro; Hara, Yoshitaka; Nihira, Takuya; Yamada, Yasuhiro

doi:10.1111/j.1574-6968.1997.tb12756.x

Cited by 18 publications

(9 citation statements)

References 20 publications

(28 reference statements)

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“…The minimum concentrations of SRB1 ( 1 = 1 a ) and SRB2 ( 2 = 2 a ) for induction of antibiotic production in S. rochei were 42 n M and 40 n M , respectively. These values were lower than those of SCB1 (128–256 n M ) for actinorhodin and undecylprodigiosin production in S. coelicolor 31 and higher than those of A‐factor (around 1 n M ) for streptomycin in S. griseus 6 and of virginia butanolides (around 3 n M ) for virginiamycin in S. virginiae 32. The synthetic 1′ S isomers 1 b and 2 b exhibited significantly weaker activities than the 1′ R isomers 1 a and 2 a , indicating that the stereochemistry at C‐1′ is crucial for induction of activity.…”

Section: Discussionmentioning

confidence: 60%

The Butenolide Signaling Molecules SRB1 and SRB2 Induce Lankacidin and Lankamycin Production in Streptomyces rochei

et al. 2012

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New signaling molecules that induce lankacidin and lankamycin production in Streptomyces rochei were extracted from the culture filtrate and purified by Sephadex LH20 and silica gel chromatography with the help of bioassay. Chiral HPLC and ESI-MS analyses indicated the presence of two active components--SRB1 and SRB2--and their molecular formulas were established to be C15H24O5 and C16H26O5, respectively. By extensive NMR analysis, SRB1 and SRB2 were determined to be 2-(1'-hydroxy-6'-oxo-8'-methylnonyl)-3-methyl-4-hydroxybut-2-en-1,4-olide and 2-(1'-hydroxy-6'-oxo-8'-methyldecyl)-3-methyl-4-hydroxybut-2-en-1,4-olide, respectively. These structures were finally confirmed by chemical synthesis and the absolute configuration at C-1' was determined to be R in each case. The synthetic 1'R isomers induced production of lankacidin and lankamycin at around 40 nM concentrations. SRB1 and SRB2 are therefore distinct from the well-known 2,3-disubstituted γ-butyrolactone molecules such as A-factor, virginia butanolide, and SCB1 and and belong, like avenolide, recently isolated from Streptomyces avermitilis, to the γ-butenolide family.

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Section: Discussionmentioning

confidence: 60%

The Butenolide Signaling Molecules SRB1 and SRB2 Induce Lankacidin and Lankamycin Production in Streptomyces rochei

et al. 2012

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“…Effects of γ-butyrolactones on development of S. coelicolor was suggested in Kawabuchi et al . 39 , but they were unable to prove that this effect was due to γ-butyrolactones. This difference in sporulation (Fig.…”

Section: Resultsmentioning

confidence: 98%

Molecular characterization of a Rhodococcus jostii RHA1 γ-butyrolactone(-like) signalling molecule and its main biosynthesis gene gblA

Ceniceros

Dijkhuizen

Petrusma

2017

Sci Rep

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Rhodococcus genome sequence analysis has revealed a surprisingly large (and unexplored) potential for the production of secondary metabolites. Also, putative γ-butyrolactone gene clusters have been identified in some Rhodococci. These signalling molecules are known to regulate secondary metabolism in Streptomyces. This work provides evidence for synthesis of a γ-butyrolactone(-like) molecule by Rhodococci (RJB), the first report in the Rhodococcus genus. The Rhodococcus jostii RHA1 RJB molecule was detected by a reporter system based on the γ-butyrolactone receptor protein (ScbR) of Streptomyces coelicolor. This RJB is structurally identical to 6-dehydro SCB2, the predicted precursor of the S. coelicolor γ-butyrolactone SCB2. The R. jostii RHA1 key RJB biosynthesis gene was identified (gblA): Deletion of gblA resulted in complete loss of RJB synthesis whereas higher RJB levels were detected when gblA was overexpressed. Interaction of the RJB molecule with ScbR indicates that communication may occur between these two Actinomycete genera in their natural habitat. Furthermore, RJB may provide a highly relevant tool for awakening cryptic secondary metabolic gene clusters in Rhodococci. This study provides preliminary evidence that R. jostii RHA1 indeed synthesizes diffusible molecules with antimicrobial activity, but a possible role for RJB in this remains to be established.

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“…Streptomyces coelicolor A3(2) and its derivatives have previously been shown to make gamma‐butyrolactone autoregulators, including SCB1 (Anisova et al ., 1984; Efremenkova et al ., 1985; Kawabuchi et al ., 1997; Takano et al ., 2000), and the key genes for production, scbA and scbR , have been identified on the chromosome (Takano et al ., 2001). Inactivation of either of these two adjacent genes eliminated detectable production of gamma‐butyrolactones by the SCP1‐free strain M145 (Takano et al ., 2001).…”

Section: Resultsmentioning

confidence: 99%

Extracellular signalling, translational control, two repressors and an activator all contribute to the regulation of methylenomycin production inStreptomyces coelicolor

O’Rourke

Wietzorrek

Fowler

et al. 2009

Molecular Microbiology

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SummaryBioinformatic analysis of the plasmid-linked gene cluster associated with biosynthesis of methylenomycin (Mm) suggested that part of the cluster directs synthesis of a gamma-butyrolactone-like autoregulator. Autoregulator activity could be extracted from culture fluids, but differed from gammabutyrolactones in being alkali resistant. The activity has recently been shown to comprise a series of novel autoregulator molecules, the methylenomycin furans (termed MMF). MMF autoregulator activity is shown to account for the ability of certain Mm non-producing mutants to act as 'secretors' in cosynthesis with other 'convertor' mutants. Three genes implicated in MMF biosynthesis are flanked by two regulatory genes, which are related to genes for gamma-butyrolactone-binding proteins. Genetic evidence suggests that these two genes encode components of a hetero-oligomeric repressor of MMF and Mm biosynthesis. The Mm biosynthetic genes themselves depend on the activator gene mmyB, which appears to be repressed by the putative MmyR/ MmfR complex until enough MMF accumulates to release repression. The presence of TTA codons in mmyB and the main MMF biosynthetic gene causes Mm production to be dependent on the pleiotropically acting bldA gene, which encodes the tRNA for the rarely used UUA codon.

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Production of butyrolactone autoregulators by Streptomyces coelicolor A3(2)

Cited by 18 publications

References 20 publications

The Butenolide Signaling Molecules SRB1 and SRB2 Induce Lankacidin and Lankamycin Production in Streptomyces rochei

The Butenolide Signaling Molecules SRB1 and SRB2 Induce Lankacidin and Lankamycin Production in Streptomyces rochei

Molecular characterization of a Rhodococcus jostii RHA1 γ-butyrolactone(-like) signalling molecule and its main biosynthesis gene gblA

Extracellular signalling, translational control, two repressors and an activator all contribute to the regulation of methylenomycin production inStreptomyces coelicolor

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