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Chemical Compound Review

Menomycin     (2S,3R,4R,5R,6R)-5- [(2S,3R,4R,5S,6R)-3...

Synonyms: Gainpro, Flavomycins, Moenomycins, Bambermycins, AC1O5GFG, ...
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Disease relevance of Flavophospholipol


High impact information on Flavophospholipol


Chemical compound and disease context of Flavophospholipol


Biological context of Flavophospholipol


Anatomical context of Flavophospholipol


Associations of Flavophospholipol with other chemical compounds


Gene context of Flavophospholipol

  • All mutants with a disrupted pbp2a gene showed higher sensitivity to moenomycin, an antibiotic known to inhibit PBP-associated glycosyltransferase activity, indicating that PBP2a is the primary target for glycosyltransferase inhibitors in S. pneumoniae [20].
  • Disruption of the gene lmo2229 encoding PBP4 in L. monocytogenes EGD did not have any significant effect on growth rate, peptidoglycan composition, cell morphology, or sensitivity to beta-lactam antibiotics but did increase the resistance of the mutant to moenomycin [21].
  • This binding was inhibited by the antibiotic moenomycin and was specific for the GT domain, since no signal was observed in the presence of the purified functional TP domain [22].
  • The latter enzyme was not inhibited by moenomycin, since deletion of the three class A PBP genes led to high-level resistance to this glycosyltransferase inhibitor [23].
  • In one, 960 Medium White poults were fed 0,2,3, or 4 mg bambermycins per kg from day-old to 12 wk of age [24].

Analytical, diagnostic and therapeutic context of Flavophospholipol

  • Group A was the negative control group without any AMGP, group B received the same feed with 9 mg of flavophospholipol/kg of feed (study group), and group C received the same feed with 15 mg of avoparcin/kg (positive control) [2].
  • With moenomycin coupled to Affi-Gel beads, a simple filtration procedure allows the amount of labeled PBPs that bind to moenomycin beads in the presence of test substances to be determined [25].
  • A novel assay based on surface plasmon resonance (SPR) has been established that can be used to investigate selective binding of the moenomycin sugar moiety and other transglycosylase inhibitors to this enzyme [26].
  • Semi-preparative high performance liquid chromatography followed by high performance liquid chromatography-mass spectrometry provided structural data on the different moenomycin components [27].


  1. Vancomycin analogues active against vanA-resistant strains inhibit bacterial transglycosylase without binding substrate. Chen, L., Walker, D., Sun, B., Hu, Y., Walker, S., Kahne, D. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  2. Effects of flavophospholipol on resistance in fecal Escherichia coli and enterococci of fattening pigs. van den Bogaard, A.E., Hazen, M., Hoyer, M., Oostenbach, P., Stobberingh, E.E. Antimicrob. Agents Chemother. (2002) [Pubmed]
  3. Reduced content of lysyl-phosphatidylglycerol in the cytoplasmic membrane affects susceptibility to moenomycin, as well as vancomycin, gentamicin, and antimicrobial peptides, in Staphylococcus aureus. Nishi, H., Komatsuzawa, H., Fujiwara, T., McCallum, N., Sugai, M. Antimicrob. Agents Chemother. (2004) [Pubmed]
  4. Induction and control of the autolytic system of Escherichia coli. Leduc, M., Kasra, R., van Heijenoort, J. J. Bacteriol. (1982) [Pubmed]
  5. Flavophospholipol use in animals: Positive implications for antimicrobial resistance based on its microbiologic properties. Pfaller, M.A. Diagn. Microbiol. Infect. Dis. (2006) [Pubmed]
  6. Cloning and characterization of PBP 1C, a third member of the multimodular class A penicillin-binding proteins of Escherichia coli. Schiffer, G., Höltje, J.V. J. Biol. Chem. (1999) [Pubmed]
  7. Anchor structure of staphylococcal surface proteins. IV. Inhibitors of the cell wall sorting reaction. Ton-That, H., Schneewind, O. J. Biol. Chem. (1999) [Pubmed]
  8. Interactions of soluble penicillin-binding protein 2a of methicillin-resistant Staphylococcus aureus with moenomycin. Graves-Woodward, K., Pratt, R.F. Biochemistry (1999) [Pubmed]
  9. Increased glycan chain length distribution and decreased susceptibility to moenomycin in a vancomycin-resistant Staphylococcus aureus mutant. Komatsuzawa, H., Ohta, K., Yamada, S., Ehlert, K., Labischinski, H., Kajimura, J., Fujiwara, T., Sugai, M. Antimicrob. Agents Chemother. (2002) [Pubmed]
  10. Correlation between degradation and ultrastructure of peptidoglycan during autolysis of Escherichia coli. Leduc, M., Frehel, C., van Heijenoort, J. J. Bacteriol. (1985) [Pubmed]
  11. Involvement of the relA gene in the autolysis of Escherichia coli induced by inhibitors of peptidoglycan biosynthesis. Kusser, W., Ishiguro, E.E. J. Bacteriol. (1985) [Pubmed]
  12. Antibacterial activity of synthetic analogues based on the disaccharide structure of moenomycin, an inhibitor of bacterial transglycosylase. Baizman, E.R., Branstrom, A.A., Longley, C.B., Allanson, N., Sofia, M.J., Gange, D., Goldman, R.C. Microbiology (Reading, Engl.) (2000) [Pubmed]
  13. Impact of flavophospholipol and vancomycin on conjugational transfer of vancomycin resistance plasmids. Riedl, S., Ohlsen, K., Werner, G., Witte, W., Hacker, J. Antimicrob. Agents Chemother. (2000) [Pubmed]
  14. Peptidoglycan synthesis in the absence of class A penicillin-binding proteins in Bacillus subtilis. McPherson, D.C., Popham, D.L. J. Bacteriol. (2003) [Pubmed]
  15. Effect of flavophospholipol on conjugation frequency between Escherichia coli donor and recipient pairs in vitro and in the chicken gastrointestinal tract. Poole, T.L., McReynolds, J.L., Edrington, T.S., Byrd, J.A., Callaway, T.R., Nisbet, D.J. J. Antimicrob. Chemother. (2006) [Pubmed]
  16. Scintillation proximity assay for inhibitors of Escherichia coli MurG and, optionally, MraY. Ravishankar, S., Kumar, V.P., Chandrakala, B., Jha, R.K., Solapure, S.M., de Sousa, S.M. Antimicrob. Agents Chemother. (2005) [Pubmed]
  17. Assessment of various treatments to reduce carriage of Salmonella in swine. Letellier, A., Messier, S., Lessard, L., Quessy, S. Can. J. Vet. Res. (2000) [Pubmed]
  18. Effects of moenomycin on Escherichia coli. van Heijenoort, Y., Leduc, M., Singer, H., van Heijenoort, J. J. Gen. Microbiol. (1987) [Pubmed]
  19. The use of bambermycins (Flavomycin) and halofuginone (Stenorol) in diets for growing turkeys. Waldroup, P.W., Spencer, G.K., Waibel, P.E., Quarles, C.L., Grant, R.J. Poult. Sci. (1985) [Pubmed]
  20. Mutational analysis of the Streptococcus pneumoniae bimodular class A penicillin-binding proteins. Paik, J., Kern, I., Lurz, R., Hakenbeck, R. J. Bacteriol. (1999) [Pubmed]
  21. Characterization of the bifunctional glycosyltransferase/acyltransferase penicillin-binding protein 4 of Listeria monocytogenes. Zawadzka-Skomial, J., Markiewicz, Z., Nguyen-Distèche, M., Devreese, B., Frère, J.M., Terrak, M. J. Bacteriol. (2006) [Pubmed]
  22. Functional characterization of penicillin-binding protein 1b from Streptococcus pneumoniae. Di Guilmi, A.M., Dessen, A., Dideberg, O., Vernet, T. J. Bacteriol. (2003) [Pubmed]
  23. Role of class A penicillin-binding proteins in PBP5-mediated beta-lactam resistance in Enterococcus faecalis. Arbeloa, A., Segal, H., Hugonnet, J.E., Josseaume, N., Dubost, L., Brouard, J.P., Gutmann, L., Mengin-Lecreulx, D., Arthur, M. J. Bacteriol. (2004) [Pubmed]
  24. Effect of bambermycins (Flavomycin) in diets for growing turkeys. Salmon, R.E., Stevens, V.I. Poult. Sci. (1990) [Pubmed]
  25. A simple screen for murein transglycosylase inhibitors. Vollmer, W., Höltje, J.V. Antimicrob. Agents Chemother. (2000) [Pubmed]
  26. A surface plasmon resonance analysis of the interaction between the antibiotic moenomycin A and penicillin-binding protein 1b. Stembera, K., Vogel, S., Buchynskyy, A., Ayala, J.A., Welzel, P. Chembiochem (2002) [Pubmed]
  27. Isolation and analysis of moenomycin and its biosynthetic intermediates from Streptomyces ghanaensis (ATCC 14672) wildtype and selected mutants. Subramaniam-Niehaus, B., Schneider, T., Metzger, J.W., Wohlleben, W. Z. Naturforsch., C, J. Biosci. (1997) [Pubmed]
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