Pseudopyronines B
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| Category | Antibiotics |
| Catalog number | BBF-02435 |
| CAS | 420782-01-0 |
| Molecular Weight | 294.4 |
| Molecular Formula | C18H30O3 |
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Description
Pseudopyronines B is an alpha-pyrone antibiotic produced by Pseudomonas fluorescens. It exhibits activity against Staphylococcus aureus and Escherichia coli with IC50 of 2.5 and >64 μg/mL, respectively.
Specification
| Synonyms | Sch 419560; Sch-419560 |
| IUPAC Name | 6-heptyl-3-hexyl-4-hydroxypyran-2-one |
| Canonical SMILES | CCCCCCCC1=CC(=C(C(=O)O1)CCCCCC)O |
| InChI | InChI=1S/C18H30O3/c1-3-5-7-9-10-12-15-14-17(19)16(18(20)21-15)13-11-8-6-4-2/h14,19H,3-13H2,1-2H3 |
| InChI Key | SJGBVXPXTMNDDG-UHFFFAOYSA-N |
Properties
| Appearance | Pale Yellow Solid |
Reference Reading
1. Experimental and Computational Studies on the Biotransformation of Pseudopyronines with Human Cytochrome P450 CYP4F2
Ya Lu, Xueling Liu, Rowaa Lotfy, Sijie Liu, Abel Fekadu Tesfa, Gerhard Wolber, Matthias Bureik, Benjamin R Clark J Nat Prod. 2022 Nov 25;85(11):2603-2609. doi: 10.1021/acs.jnatprod.2c00616. Epub 2022 Nov 3.
The secondary metabolite pseudopyronine B, isolated from Pseudomonas mosselii P33, was biotransformed by human P450 enzymes, heterologously expressed in the fission yeast Schizosaccharomyces pombe. Small-scale studies confirmed that both CYP4F2 and CYP4F3A were capable of oxidizing the substrate, with the former achieving a higher yield. In larger-scale studies using CYP4F2, three new oxidation products were obtained, the structures of which were elucidated by UV-vis, 1D and 2D NMR, and HR-MS spectroscopy. These corresponded to hydroxylated, carboxylated, and ester derivatives (1-3) of pseudopyronine B, all of which had been oxidized exclusively at the ω-position of the C-6 alkyl chain. In silico homology modeling experiments highlighted key interactions between oxygen atoms of the pyrone ring and two serine residues and a histidine residue of CYP4F2, which hold the substrate in a suitable orientation for oxidation at the terminus of the C-6 alkyl chain. Additional modeling studies with all three pseudopyronines revealed that the seven-carbon alkyl chain of pseudopyronine B was the perfect length for oxidation, with the terminal carbon lying close to the heme iron. The antibacterial activity of the substrates and three oxidation products was also assessed, revealing that oxidation at the ω-position removes all antimicrobial activity. This study both increases the range of known substrates for human CYF4F2 and CYP4F3A enzymes and demonstrates their utility in producing additional natural product derivatives.
2. Isolation of the antibiotic pseudopyronine B and SAR evaluation of C3/C6 alkyl analogs
Leah M Bouthillette, Catherine A Darcey, Tess E Handy, Sarah C Seaton, Amanda L Wolfe Bioorg Med Chem Lett. 2017 Jun 15;27(12):2762-2765. doi: 10.1016/j.bmcl.2017.04.067. Epub 2017 Apr 23.
Natural products are an abundant source of structurally diverse compounds with antibacterial activity that can be used to develop new and potent antibiotics. One such class of natural products is the pseudopyronines. Here we present the isolation of pseudopyronine B (2) from a Pseudomonas species found in garden soil in Western North Carolina, and SAR evaluation of C3 and C6 alkyl analogs of the natural product for antibacterial activity against Gram-positive and Gram-negative bacteria. We found a direct relationship between antibacterial activity and C3/C6 alkyl chain length. For inhibition of Gram-positive bacteria, alkyl chain lengths between 6 and 7 carbons were found to be the most active (IC50=0.04-3.8µg/mL) whereas short alkyl chain analogs showed modest activity against Gram-negative bacteria (IC50=223-304µg/mL). This demonstrates the potential for this class of natural products to be optimized for selective activity against either Gram-positive or Gram-negative bacteria.
3. Retraction: Pseudopyronine B: A Potent Antimicrobial and Anticancer Molecule Isolated from a Pseudomonas mosselii
Frontiers Editorial Office Front Microbiol. 2017 Nov 17;8:2263. doi: 10.3389/fmicb.2017.02363. eCollection 2017.
[This retracts the article on p. 1307 in vol. 7, PMID: 27617005.].
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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 ╳
