Serratamolide
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| Category | Antibiotics |
| Catalog number | BBF-02905 |
| CAS | 5285-25-6 |
| Molecular Weight | 514.65 |
| Molecular Formula | C26H46N2O8 |
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Description
It is a depsipeptide antibiotic produced by the strain of Serratia marcescens HY-3. It has anti-gram-positive bacteria, mycobacteria and fungi activity, but the activity is weak.
Specification
| Synonyms | Serrawettin W1; serratamolide A; NSC 81415; Cyclic(D-beta-hydroxydecanoyl-L-seryl-D-beta-hydroxydecanoyl-L-seryl) |
| IUPAC Name | (3S,7R,10S,14R)-7,14-diheptyl-3,10-bis(hydroxymethyl)-1,8-dioxa-4,11-diazacyclotetradecane-2,5,9,12-tetrone |
| Canonical SMILES | CCCCCCCC1CC(=O)NC(C(=O)OC(CC(=O)NC(C(=O)O1)CO)CCCCCCC)CO |
| InChI | InChI=1S/C26H46N2O8/c1-3-5-7-9-11-13-19-15-23(31)27-22(18-30)26(34)36-20(14-12-10-8-6-4-2)16-24(32)28-21(17-29)25(33)35-19/h19-22,29-30H,3-18H2,1-2H3,(H,27,31)(H,28,32)/t19-,20-,21+,22+/m1/s1 |
| InChI Key | NMEMNUVHBNAERZ-CZYKHXBRSA-N |
Properties
| Appearance | White Fine Needle Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Fungi; Mycobacteria |
| Boiling Point | 817.1±65.0°C (Predicted) |
| Melting Point | 159-160°C |
| Density | 1.059±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Chloroform, Ethanol |
Reference Reading
1. Serratia marcescens Cyclic AMP Receptor Protein Controls Transcription of EepR, a Novel Regulator of Antimicrobial Secondary Metabolites
Nicholas A Stella, Roni M Lahr, Kimberly M Brothers, Eric J Kalivoda, Kristin M Hunt, Daniel H Kwak, Xinyu Liu, Robert M Q Shanks J Bacteriol. 2015 Aug 1;197(15):2468-78. doi: 10.1128/JB.00136-15. Epub 2015 Apr 20.
Serratia marcescens generates secondary metabolites and secreted enzymes, and it causes hospital infections and community-acquired ocular infections. Previous studies identified cyclic AMP (cAMP) receptor protein (CRP) as an indirect inhibitor of antimicrobial secondary metabolites. Here, we identified a putative two-component regulator that suppressed crp mutant phenotypes. Evidence supports that the putative response regulator eepR was directly transcriptionally inhibited by cAMP-CRP. EepR and the putative sensor kinase EepS were necessary for the biosynthesis of secondary metabolites, including prodigiosin- and serratamolide-dependent phenotypes, swarming motility, and hemolysis. Recombinant EepR bound to the prodigiosin and serratamolide promoters in vitro. Together, these data introduce a novel regulator of secondary metabolites that directly connects the broadly conserved metabolism regulator CRP with biosynthetic genes that may contribute to competition with other microbes. Importance: This study identifies a new transcription factor that is directly controlled by a broadly conserved transcription factor, CRP. CRP is well studied in its role to help bacteria respond to the amount of nutrients in their environment. The new transcription factor EepR is essential for the bacterium Serratia marcescens to produce two biologically active compounds, prodigiosin and serratamolide. These two compounds are antimicrobial and may allow S. marcescens to compete for limited nutrients with other microorganisms. Results from this study tie together the CRP environmental nutrient sensor with a new regulator of antimicrobial compounds. Beyond microbial ecology, prodigiosin and serratamolide have therapeutic potential; therefore, understanding their regulation is important for both applied and basic science.
2. PsrA is a novel regulator contributes to antibiotic synthesis, bacterial virulence, cell motility and extracellular polysaccharides production in Serratia marcescens
Xuewei Pan, Mi Tang, Jiajia You, Tolbert Osire, Changhao Sun, Weilai Fu, Ganfeng Yi, Taowei Yang, Shang-Tian Yang, Zhiming Rao Nucleic Acids Res. 2022 Jan 11;50(1):127-148. doi: 10.1093/nar/gkab1186.
Serratia marcescens is a Gram-negative bacterium of the Enterobacteriaceae family that can produce numbers of biologically active secondary metabolites. However, our understanding of the regulatory mechanisms behind secondary metabolites biosynthesis in S. marcescens remains limited. In this study, we identified an uncharacterized LysR family transcriptional regulator, encoding gene BVG90_12635, here we named psrA, that positively controlled prodigiosin synthesis in S. marcescens. This phenotype corresponded to PsrA positive control of transcriptional of the prodigiosin-associated pig operon by directly binding to a regulatory binding site (RBS) and an activating binding site (ABS) in the promoter region of the pig operon. We demonstrated that L-proline is an effector for the PsrA, which enhances the binding affinity of PsrA to its target promoters. Using transcriptomics and further experiments, we show that PsrA indirectly regulates pleiotropic phenotypes, including serrawettin W1 biosynthesis, extracellular polysaccharide production, biofilm formation, swarming motility and T6SS-mediated antibacterial activity in S. marcescens. Collectively, this study proposes that PsrA is a novel regulator that contributes to antibiotic synthesis, bacterial virulence, cell motility and extracellular polysaccharides production in S. marcescens and provides important clues for future studies exploring the function of the PsrA and PsrA-like proteins which are widely present in many other bacteria.
3. Identification of a methicillin-resistant Staphylococcus aureus inhibitory compound isolated from Serratia marcescens
Daniel E Kadouri, Robert M Q Shanks Res Microbiol. 2013 Oct;164(8):821-6. doi: 10.1016/j.resmic.2013.06.002. Epub 2013 Jun 20.
In this study, we identified an antimicrobial compound produced by the Gram-negative bacterium Serratia marcescens. Colonies of S. marcescens inhibited the growth of nine different methicillin-resistant Staphylococcus aureus (MRSA) isolates and several other tested Gram-positive bacterial species, but not Gram-negative bacteria. Genetic analysis revealed the requirement for the swrW gene which codes for a non-ribosomal peptide synthetase that generates the cyclodepsipeptide antibiotic serratamolide, also known as serrawettin W1. This is the first report describing the anti-MRSA properties of serratamolide.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
