LL-E19020.ALPHA. and .BETA., animal growth promoting antibiotics: Taxonomy, fermentation and biological activity.

Maiese, William M.; Lechevalier, Mary P.; Lechevalier, H. A.; Korshalla, J.; Goodman, Joseph J.; Wildey, Mary Jo; Kuck, N. A.; Conner, S. D.; Greenstein, Michael

doi:10.7164/antibiotics.42.1489

Cited by 10 publications

(3 citation statements)

References 7 publications

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“…Efrotomycin features a disaccharide moiety at 30-OH . The elfamycin family of antibiotics are inhibitors of bacterial protein synthesis by interaction with elongation factor Tu and also show a narrow antibacterial spectrum against human pathogens and excellent growth-promoting activity in animals . The biosynthetic gene clusters (BGCs) have been identified for kirromycin, factumycin, and aurodox; however, the biosynthetic machinery governing the glycosylated elfamycins is not yet clear.…”

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confidence: 99%

Discovery of Efrotomycin Congeners and Heterologous Expression-Based Insights into the Self-Resistance Mechanism

Fang

Zhang

et al. 2022

J. Nat. Prod.

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Four new efrotomycins, A1–A4 (1–4), were isolated from the salt mine-derived Amycolatopsis cihanbeyliensis DSM 45679 and structurally determined. Efrotomycins A3 (3) and A4 (4) feature a tetrahydrofuran ring configured distinctly from known elfamycins. Heterologous expression of the efrotomycin gene cluster (efr BGC) in Streptomyces lividans SBT18 led to efrotomycin B1 (5), the yield of which was improved several fold upon introduction of the transporter gene efrT, a putative self-resistance determinant outside of the efr BGC.

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confidence: 99%

Discovery of Efrotomycin Congeners and Heterologous Expression-Based Insights into the Self-Resistance Mechanism

Fang

Zhang

et al. 2022

J. Nat. Prod.

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“…Ganefromycins, a family of elfamycin antibiotics produced by S treptomyces lydicus spp. tanzanius Lechevalier (Streptomycetaceae), have shown excellent growth-promoting activity in animals. , A series of ganefromycin antibiotics ( 1 − 7 and 9 − 15 ) has been isolated and identified in order to establish their biosynthetic relationships to the previously reported ganefromycin α ( 8 ). The biogenesis of the aglycon of 8 and other elfamycin antibiotics is clearly polyketide.…”

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confidence: 99%

Biosynthesis of Ganefromycin: Results from Blocked Mutants and Bioconversion Experiments

McDonald¹,

Lotvin²,

Bailey³

et al. 1998

J. Nat. Prod.

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The biosynthetic pathway of ganefromycin alpha (8) was investigated using blocked mutants of Streptomyces lydicus spp. tanzanius, the ganefromycin alpha producer, in conjunction with bioconversion experiments with the products of these mutants. Compounds 1-7 and 9-15, which are structurally related to ganefromycin alpha, were produced by cultures of secretor mutants showing blockage or diminished production of 8. These compounds were isolated, characterized, and subjected to bioconversion experiments using converter and other secretor mutants. Some of the compounds were shown to be products resulting from blocks at various stages in the biosynthetics pathway beyond construction of the polyketide skeleton (e.g., furan ring closure, hydroxylation, glycosylation, etc.). Other compounds were not bioconverted by biosynthetically capable mutants and were deemed shunt products. A mutant's metabolites and bioconverting ability were used to surmise the location of the block. A picture of the later sequence of events leading to the synthesis of ganefromycin alpha emerged, including C23-hydroxylation, C13a-O-methylation, C21a-hydroxylation, and C21a-O-glycosylation. Some of the later steps in the biosynthetic pathway for ganefromycin alpha are proposed.

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“…12,13 All elfamycins show a very narrow antibacterial spectrum against human pathogens and most of them show excellent activities as growth-promoting agents in animals. 14 In this paper we report on the new phenelfamycins 1 and 2, the taxonomy of the producing strain, their fermentation, isolation, structure elucidation and biological activity. …”

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Phenelfamycins G and H, new elfamycin-type antibiotics produced by Streptomyces albospinus Acta 3619

et al. 2011

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Phenelfamycins G and H are new members of the family of elfamycin antibiotics with the basic structure of phenelfamycins E and F, respectively, which are also well known as ganefromycins a and b. Phenelfamycins G and H differ from phenelfamycins E and F by an additional hydroxy group at position C-30, which is not described so far for any of the elfamycin-type antibiotics. The actinomycete strain that produced phenelfamycins G and H was identified to be Streptomyces albospinus based on its 16S rRNA gene sequence. Phenelfamycins G and H exhibit a narrow antibacterial spectrum with a pronounced inhibitory activity against Propionibacterium acnes. The Journal of Antibiotics (2011) 64, 257-266; doi:10.1038/ja2010.170; published online 2 February 2011 Keywords: elfamycin antibiotics; ganefromycin; phenelfamycin; Propionibacterium acnes; Streptomyces INTRODUCTIONEnvironmental samples were collected from untapped Malaysian ecological niches to isolate actinomycetes strains, which were investigated within our HPLC-diode array screening program for the production of secondary metabolites with the aim of detecting novel drugs for pharmaceutical applications. 1 Strain Acta 3619 was isolated from a soil collected from the rhizosphere of bamboo trees in the tropical rainforest of the University of Malaya Field Station at Gombak, Selangor, Malaysia. The strain was found to be of special interest, as it gave two significant peaks in the HPLC analysis of an extract of the culture filtrate having congruent UV-vis spectra that differed from all 937 reference compounds stored in our HPLC-UVvis database. 2 Structure elucidation of the two isolated compounds revealed a relationship with phenelfamycins E and F and therefore were named as phenelfamycins G (1) and H (2), respectively. Their structures are shown in Figure 1.Phenelfamycins belong to the elfamycin family of antibiotics, which inhibit protein synthesis of bacteria by an interaction with elongation factor Tu, demonstrated in prokaryotic cells. [3][4][5] Hence they derived their name from this interaction. Elfamycins can be subdivided into three types according to their structure. Type 1 includes kirromycin 6 (mocimycin), aurodox, 7,8 heneicomycin 9 and efrotomycin. 10 Type 2, elfamycin, is represented by kirrothricin with an open tetrahydrofuran ring in the aglycone. 11 Finally, type 3 contains the phenelfamycins with a phenylacetyl substitution at position C-22 or C-23 and C-33 O-glycosylation with mono-(phenelfamycins A and B), di-(phenelfamycins C and D) or trisaccharide units (phenelfamycins E and F, also named as ganefromycins a and b). 12,13 All elfamycins show a very narrow antibacterial spectrum against human pathogens and most of them show excellent activities as growth-promoting agents in animals. 14 In this paper we report on the new phenelfamycins 1 and 2, the taxonomy of the producing strain, their fermentation, isolation, structure elucidation and biological activity. RESULTS Taxonomy of the producing strainStrain Acta 3619 was isolated from the rhizosphere so...

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LL-E19020.ALPHA. and .BETA., animal growth promoting antibiotics: Taxonomy, fermentation and biological activity.

Cited by 10 publications

References 7 publications

Discovery of Efrotomycin Congeners and Heterologous Expression-Based Insights into the Self-Resistance Mechanism

Discovery of Efrotomycin Congeners and Heterologous Expression-Based Insights into the Self-Resistance Mechanism

Biosynthesis of Ganefromycin: Results from Blocked Mutants and Bioconversion Experiments

Phenelfamycins G and H, new elfamycin-type antibiotics produced by Streptomyces albospinus Acta 3619

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