Alnumycin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00423 |
| CAS | |
| Molecular Weight | 416.42 |
| Molecular Formula | C22H24O8 |
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Description
It is produced by the strain of Streptomyces sp. DSM 11575. The antibacterial spectrum is narrow, and it only has the activity of resistant bacillus subtilis, gambogic micrococcus and other gram-positive bacteria, but has no effect on gram-negative bacteria. It can inhibit the growth of K562 human leukemic cells with IC50 of 0.53 ㎍/mL.
Specification
| IUPAC Name | 10-hydroxy-8-[(2R,4S,5R)-5-hydroxy-4-(hydroxymethyl)-1,3-dioxan-2-yl]-3-methyl-1-propyl-1H-benzo[g]isochromene-6,9-dione |
| Canonical SMILES | CCCC1C2=C(C3=C(C=C2C=C(O1)C)C(=O)C=C(C3=O)C4OCC(C(O4)CO)O)O |
| InChI | InChI=1S/C22H24O8/c1-3-4-16-18-11(5-10(2)29-16)6-12-14(24)7-13(20(26)19(12)21(18)27)22-28-9-15(25)17(8-23)30-22/h5-7,15-17,22-23,25,27H,3-4,8-9H2,1-2H3/t15-,16?,17+,22-/m1/s1 |
| InChI Key | DRXHQLTVRTWTGH-WABLBPIPSA-N |
Properties
| Appearance | Red Fine Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 134-136 °C |
| Solubility | Soluble in Methanol |
Reference Reading
1. Effective Antibiofilm Polyketides against Staphylococcus aureus from the Pyranonaphthoquinone Biosynthetic Pathways of Streptomyces Species
Terhi Oja, Paola San Martin Galindo, Takaaki Taguchi, Suvi Manner, Pia M Vuorela, Koji Ichinose, Mikko Metsä-Ketelä, Adyary Fallarero Antimicrob Agents Chemother. 2015 Oct;59(10):6046-52. doi: 10.1128/AAC.00991-15. Epub 2015 Jul 20.
Streptomyces bacteria are renowned for their ability to produce bioactive secondary metabolites. Recently, synthetic biology has enabled the production of intermediates and shunt products, which may have altered biological activities compared to the end products of the pathways. Here, we have evaluated the potential of recently isolated alnumycins and other closely related pyranonaphthoquinone (PNQ) polyketides against Staphylococcus aureus biofilms. The antimicrobial potency of the compounds against planktonic cells and biofilms was determined by redox dye-based viability staining, and the antibiofilm efficacy of the compounds was confirmed by viable counting. A novel antistaphylococcal polyketide, alnumycin D, was identified. Unexpectedly, the C-ribosylated pathway shunt product alnumycin D was more active against planktonic and biofilm cells than the pathway end product alnumycin A, where a ribose unit has been converted into a dioxane moiety. The evaluation of the antibiofilm potential of other alnumycins revealed that the presence of the ribose moiety in pyranose form is essential for high activity against preformed biofilms. Furthermore, the antibiofilm potential of other closely related PNQ polyketides was examined. Based on their previously reported activity against planktonic S. aureus cells, granaticin B, kalafungin, and medermycin were also selected for testing, and among them, granaticin B was found to be the most potent against preformed biofilms. The most active antibiofilm PNQs, alnumycin D and granaticin B, share several structural features that may be important for their antibiofilm activity. They are uncharged, glycosylated, and also contain a similar oxygenation pattern of the lateral naphthoquinone ring. These findings highlight the potential of antibiotic biosynthetic pathways as a source of effective antibiofilm compounds.
2. Structural characterization of three noncanonical NTF2-like superfamily proteins: implications for polyketide biosynthesis
Nemanja Vuksanovic, Xuechen Zhu, Dante A Serrano, Vilja Siitonen, Mikko Metsä-Ketelä, Charles E Melançon rd, Nicholas R Silvaggi Acta Crystallogr F Struct Biol Commun. 2020 Aug 1;76(Pt 8):372-383. doi: 10.1107/S2053230X20009814. Epub 2020 Jul 29.
Proteins belonging to the NTF2-like superfamily are present in the biosynthetic pathways of numerous polyketide natural products, such as anthracyclins and benzoisochromanequinones. Some have been found to be bona fide polyketide cyclases, but many of them have roles that are currently unknown. Here, the X-ray crystal structures of three NTF2-like proteins of unknown function are reported: those of ActVI-ORFA from Streptomyces coelicolor A3(2) and its homologs Caci_6494, a protein from an uncharacterized biosynthetic cluster in Catenulispora acidiphila, and Aln2 from Streptomyces sp. CM020, a protein in the biosynthetic pathway of alnumycin. The presence of a solvent-accessible cavity and the conservation of the His/Asp dyad that is characteristic of many polyketide cyclases suggest a potential enzymatic role for these enzymes in polyketide biosynthesis.
3. Michael additions in polyketide biosynthesis
Akimasa Miyanaga Nat Prod Rep. 2019 Mar 20;36(3):531-547. doi: 10.1039/c8np00071a.
Covering: up to July 2018 Polyketides constitute a large family of natural products exhibiting various biological activities. Polyketide biosynthetic systems employ several strategies for the production of structurally diverse polyketides. Among the polyketide biosynthetic enzymes, a growing number of enzymes that catalyze a Michael-type addition have been identified. These enzymes are responsible for constructing unique polyketide backbone structures, forming heterocycles, and incorporating heteroatoms into the polyketide backbone, all of which contribute to the diversification of the polyketide structure. This review summarizes the current understanding of the function of enzymes catalyzing a Michael-type addition in polyketide biosynthesis, with a particular focus on mechanistic studies.
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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 ╳
