Synonym: Lanthiopeptin, NSC-71936, Ro 09-0198
|Related Categories||Antibiotics, Antibiotics A to Z, Antibiotics A-F, Antifungal, Bioactive Small Molecules,|
|biological source||from Streptomyces cinnamoneus|
|solubility||DMSO: soluble10 mg/mL|
|acetonitrile: water (1:1): soluble5 mg/mL (requires heating)|
Cinnamycin is a tetracyclic polypeptide antibiotic containing 19 amino acids. The polypeptide has the unusual amino acids threo-3-methyl-lanthionine, meso-lanthionine, lysinoalanine and 3-hydroxyaspartic acid. It is produced by Streptomyces cinnamoneus and belongs to the duramycin-type l antibiotics. Lantibiotics are synthesized in the ribosome and undergo extensive post-translational modifications to attain their active antimicrobial form.1,2,3 The unique receptor for Cinnamycin, phosphatidylethanolamine (PE), is located on the inner leaflet of the plasma membrane.4,5 Cinnamycin induces transbilayer lipid movement leading to the exposure of PE to the outer leaflet of the plasma membrane.2,4, The interaction of Cinnamycin with PE provides a tool for PE monitoring.5 Cinnamycin is active against Gram-positive rods such as Bacilli, Clostyridium and Mycobacterium, causing cell wall biosynthesis stress.2
Cinnamycin, like other lantibiotics, was also reported to inhibit phospholipase A2 (PLA2).1 It was suggested as an alternative treatment for atherosclerosis through its ability to inhibit PLA2 by binding to its substrate PE.2,5 Moreover, Cinnamycin was found to inhibit Herpes simplex virus (HSV-1) activity.6
With bacterial resistance and emerging infectious diseases becoming potential threats to humans, ribosomally synthesized antimicrobial peptides have become a promising focus area in antibiotic resear...
BioFiles 2009, 4.3, 4.
Keywords: Antibiotics, Antimicrobials, Antiparasitics, Antivirals, Apoptosis, Cancer, Clinical, Diseases, Environmental, Fermentation, Food Safety, Gene expression, Genetic, Genetics, Infectious Diseases, Microbiology, Peptide synthesis, Pesticides, Respiratory
1. Duramycins B and C, two new lanthionine containing antibiotics as inhibitors of phospholipase A2. Structural revision of duramycin and cinnamycin. Fredenhagen, A., et al. J. Antibiot. 43, 1403-1412, (1990)
6. Lanthiopeptin, a new peptide effective against herpes simplex virus: Structural determination and comparison with Ro 09-0198, an immunopotentiating peptide. Wakamiya, T., et al. Tetrahedron Lett. 29, 3771-4772, (1988)
Involvement of Golgi-associated retrograde protein complex in the recycling of the putative Dnf aminophospholipid flippases in yeast. Takagi K, Iwamoto K, Kobayashi S, et al. Biochem. Biophys. Res. Commun. 417(1), 490-4, (2012)
Complex formation of peptide antibiotic Ro09-0198 with lysophosphatidylethanolamine: 1H NMR analyses in dimethyl sulfoxide solution. Wakamatsu K, Choung SY, Kobayashi T, et al. Biochemistry 29(1), 113-8, (1990)
A novel membrane protein, Ros3p, is required for phospholipid translocation across the plasma membrane in Saccharomyces cerevisiae. Kato U, Emoto K, Fredriksson C, et al. J. Biol. Chem. 277(40), 37855-62, (2002)
Capacitation induces cyclic adenosine 3',5'-monophosphate-dependent, but apoptosis-unrelated, exposure of aminophospholipids at the apical head plasma membrane of boar sperm cells. Gadella BM and Harrison RA Biol. Reprod. 67(1), 340-50, (2002)
An essential role for a membrane lipid in cytokinesis. Regulation of contractile ring disassembly by redistribution of phosphatidylethanolamine. Emoto K and Umeda M J. Cell Biol. 149(6), 1215-24, (2000)
Effects of docosahexaenoic and arachidonic acids on the synthesis and distribution of aminophospholipids during neuronal differentiation of PC12 cells. Ikemoto A, Kobayashi T, Emoto K, et al. Arch. Biochem. Biophys. 364(1), 67-74, (1999)
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