Roseoflavin, a New Antimicrobial Pigment From Streptomyces

Otani, Shuzo; Takatsu, Mitsumune; Nakano, Masayoshi; Kasai, Shinji; Miura, Retsu; Matsui, Kunihiko

doi:10.7164/antibiotics.27.88

Cited by 96 publications

(70 citation statements)

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“…Expression of this gene in E. coli resulted in RF-transporting transformants that were highly sensitive to roseoflavin (156). 334 ABBAS AND SIBIRNY MICROBIOL. MOL.…”

Section: Bacteriamentioning

confidence: 99%

“…As discussed above, the flavin antibiotic roseoflavin is active only against Gram-positive bacteria. Many Gram-negative bacteria are resistant to roseoflavin, probably due to the inability of this RF structural analog to enter cells (23,156,333,334). Many microorganisms are capable of RF oversynthesis and accumulation in a medium (see below), suggesting that these organisms can efficiently secrete RF.…”

Section: Riboflavin Transport Into and Out Of The Cellmentioning

confidence: 99%

“…Some natural flavins have a reddish-orange color, e.g., the antibiotic roseoflavin [7-methyl-8-dimethylamino-(1Ј-Dribityl)isoalloxazine] (Fig. 1E), which is produced by Streptomyces davawensis and is active against Gram-positive bacteria (333,334). The basidiomycete Schizophillum commune produces two RF derivatives, known as schizoflavins: 7,8-dimethyll0-(2,3,4-trihydroxy-4-carboxybutyl)isoalloxazine (RF acid or riboflavinoic acid) and 7,8-dimethyl-l0-(2,3,4-trihydroxy-4-formylbutyl)isoalloxazine (RF-aldehyde or riboflavinal) (488).…”

Section: Other Natural Flavinsmentioning

confidence: 99%

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Genetic Control of Biosynthesis and Transport of Riboflavin and Flavin Nucleotides and Construction of Robust Biotechnological Producers

Abbas

Sibirny

2011

Microbiol Mol Biol Rev

325

272

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SUMMARY Riboflavin [7,8-dimethyl-10-(1′- d -ribityl)isoalloxazine, vitamin B 2 ] is an obligatory component of human and animal diets, as it serves as the precursor of flavin coenzymes, flavin mononucleotide, and flavin adenine dinucleotide, which are involved in oxidative metabolism and other processes. Commercially produced riboflavin is used in agriculture, medicine, and the food industry. Riboflavin synthesis starts from GTP and ribulose-5-phosphate and proceeds through pyrimidine and pteridine intermediates. Flavin nucleotides are synthesized in two consecutive reactions from riboflavin. Some microorganisms and all animal cells are capable of riboflavin uptake, whereas many microorganisms have distinct systems for riboflavin excretion to the medium. Regulation of riboflavin synthesis in bacteria occurs by repression at the transcriptional level by flavin mononucleotide, which binds to nascent noncoding mRNA and blocks further transcription (named the riboswitch). In flavinogenic molds, riboflavin overproduction starts at the stationary phase and is accompanied by derepression of enzymes involved in riboflavin synthesis, sporulation, and mycelial lysis. In flavinogenic yeasts, transcriptional repression of riboflavin synthesis is exerted by iron ions and not by flavins. The putative transcription factor encoded by SEF1 is somehow involved in this regulation. Most commercial riboflavin is currently produced or was produced earlier by microbial synthesis using special selected strains of Bacillus subtilis , Ashbya gossypii , and Candida famata . Whereas earlier RF overproducers were isolated by classical selection, current producers of riboflavin and flavin nucleotides have been developed using modern approaches of metabolic engineering that involve overexpression of structural and regulatory genes of the RF biosynthetic pathway as well as genes involved in the overproduction of the purine precursor of riboflavin, GTP.

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“…Expression of this gene in E. coli resulted in RF-transporting transformants that were highly sensitive to roseoflavin (156). 334 ABBAS AND SIBIRNY MICROBIOL. MOL.…”

Section: Bacteriamentioning

confidence: 99%

Section: Riboflavin Transport Into and Out Of The Cellmentioning

confidence: 99%

Section: Other Natural Flavinsmentioning

confidence: 99%

See 1 more Smart Citation

Genetic Control of Biosynthesis and Transport of Riboflavin and Flavin Nucleotides and Construction of Robust Biotechnological Producers

Abbas

Sibirny

2011

Microbiol Mol Biol Rev

325

272

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“…S1 in the supplemental material) (13). RoF biosynthesis in S. davawensis is carried out by three enzymes.…”

mentioning

confidence: 99%

Uptake and Metabolism of Antibiotics Roseoflavin and 8-Demethyl-8-Aminoriboflavin in Riboflavin-Auxotrophic Listeria monocytogenes

et al. 2016

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The riboflavin analogs roseoflavin (RoF) and 8-demethyl-8-aminoriboflavin (AF) are produced by the bacteria Streptomyces davawensis and Streptomyces cinnabarinus. Riboflavin analogs have the potential to be used as broad-spectrum antibiotics, and we therefore studied the metabolism of riboflavin (vitamin B 2 ), RoF, and AF in the human pathogen Listeria monocytogenes, a bacterium which is a riboflavin auxotroph. We show that the L. monocytogenes protein Lmo1945 is responsible for the uptake of riboflavin, RoF, and AF. Following import, these flavins are phosphorylated/adenylylated by the bifunctional flavokinase/flavin adenine dinucleotide (FAD) synthetase Lmo1329 and adenylylated by the unique FAD synthetase Lmo0728, the first monofunctional FAD synthetase to be described in bacteria. R iboflavin (vitamin B 2 ) is not synthesized by mammals but is synthesized by many microorganisms and by all plants (1).The genomes of the human bacterial pathogens Listeria monocytogenes, Streptococcus pyogenes, and Enterococcus faecalis do not contain genes encoding riboflavin biosynthetic enzymes (2), and thus these microorganisms are riboflavin auxotrophs. L. monocytogenes, Streptococcus pyogenes, and Enterococcus faecalis produce energy-coupling factor (ECF) transporters which combine with a riboflavin-specific binding subunit (subunit EcfS or RibU) (3), and ECF-RibU-mediated uptake is the sole source of riboflavin (4).Riboflavin cannot be detected in cell extracts of bacteria (5-7), indicating that it is completely metabolized by flavokinases (RibF) (EC 2.7.1.26) and FAD synthetases (RibC) (EC 2.7.7.2). These enzymes catalyze the formation of FMN (from riboflavin and ATP) and FAD (from FMN and ATP) (see Fig. S1 in the supplemental material) and play an important role in metabolic trapping of riboflavin (8). In bacteria, bifunctional flavokinases/FAD synthetases have been found, whereas in eukarya and archaea, monofunctional enzymes seem to be the rule (9). FMN and FAD are cofactors of flavoproteins/flavoenzymes, which have a wide variety of different biological functions (10). The number of flavindependent proteins varies greatly in different organisms (and among pathogens) and covers a range from approximately 0.1% to 3.5% of the proteome (11). In Escherichia coli, FMN and FAD are present at levels which are about 30 times lower than those of the highly abundant amino acids or nucleotides (12), whereby FAD (170 M) clearly is present at higher levels than FMN (54

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“…he Gram-positive bacterium Streptomyces davawensis was first isolated from a Philippine soil sample within the framework of a screening program for novel antibiotics (45). The species name refers to the site of sampling, which was near Davao City in the Philippines (53).…”

mentioning

confidence: 99%

Genome Sequence of the Bacterium Streptomyces davawensis JCM 4913 and Heterologous Production of the Unique Antibiotic Roseoflavin

et al. 2012

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Roseoflavin, a New Antimicrobial Pigment From Streptomyces

Cited by 96 publications

References 1 publication

Genetic Control of Biosynthesis and Transport of Riboflavin and Flavin Nucleotides and Construction of Robust Biotechnological Producers

Genetic Control of Biosynthesis and Transport of Riboflavin and Flavin Nucleotides and Construction of Robust Biotechnological Producers

Uptake and Metabolism of Antibiotics Roseoflavin and 8-Demethyl-8-Aminoriboflavin in Riboflavin-Auxotrophic Listeria monocytogenes

Genome Sequence of the Bacterium Streptomyces davawensis JCM 4913 and Heterologous Production of the Unique Antibiotic Roseoflavin

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