Nornidulin
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| Category | Antibiotics |
| Catalog number | BBF-02604 |
| CAS | 33403-37-1 |
| Molecular Weight | 429.68 |
| Molecular Formula | C19H15Cl3O5 |
| Purity | >99% by HPLC |
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Description
A depsidone produced by several fungal species; has potent and selective antibacterial activity; has potential as an anti-inflammatory agent.
Specification
| Synonyms | Ustin; 2,4,7-Trichloro-3,8-dihydroxy-1,9-dimethyl-6-(1-methyl-1-propenyl)-11H-dibenzo(b,E)(1,4)dioxepin-11-one |
| Storage | Store at -20°C |
| IUPAC Name | 1-[(Z)-but-2-en-2-yl]-2,8,10-trichloro-3,9-dihydroxy-4,7-dimethylbenzo[b][1,4]benzodioxepin-6-one |
| Canonical SMILES | CC=C(C)C1=C(C(=C(C2=C1OC3=C(C(=C(C(=C3C(=O)O2)C)Cl)O)Cl)C)O)Cl |
| InChI | InChI=1S/C19H15Cl3O5/c1-5-6(2)9-12(21)14(23)8(4)16-18(9)26-17-10(19(25)27-16)7(3)11(20)15(24)13(17)22/h5,23-24H,1-4H3/b6-5- |
| InChI Key | XEQDVQKKHOQZEP-WAYWQWQTSA-N |
| Source | Emericella sp. |
Properties
| Appearance | Hexagonal Flake or Prismatic Crystals |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria |
| Boiling Point | 623.9±55.0°C at 760 mmHg |
| Melting Point | 185-186°C |
| Density | 1.5±0.1 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility. |
Reference Reading
1. Depsidones, aromatase inhibitors and radical scavenging agents from the marine-derived fungus Aspergillus unguis CRI282-03
Nattaya Ngamrojanavanich, Prasat Kittakoop, Suthep Wiyakrutta, Sanya Sureram, Somsak Ruchirawat, Chulabhorn Mahidol Planta Med . 2012 Apr;78(6):582-8. doi: 10.1055/s-0031-1298228.
Three new depsidones ( 1, 3, and 4), a new diaryl ether ( 5), and a new natural pyrone ( 9) (synthetically known), together with three known depsidones, nidulin ( 6), nornidulin ( 7), and 2-chlorounguinol ( 8), were isolated from the marine-derived fungus ASPERGILLUS UNGUIS CRI282-03. Aspergillusidone C ( 4) showed the most potent aromatase inhibitory activity with the IC (50) value of 0.74 µM, while depsidones 1, 3, 6- 8 inhibited aromatase with IC (50) values of 1.2-11.2 µM. It was found that the structural feature of depsidones, not their corresponding diaryl ether derivatives (e.g. 5), was important for aromatase inhibitory activity. Aspergillusidones A ( 1) and B ( 3) showed radical scavenging activity in the XXO assay with IC (50) values of 16.0 and < 15.6 µM, respectively. Compounds 1 and 3- 7 were mostly inactive or showed only weak cytotoxic activity against HuCCA-1, HepG2, A549, and MOLT-3 cancer cell lines.
2. Expanding antibiotic chemical space around the nidulin pharmacophore
Andrew M Piggott, Ernest Lacey, Daniel Vuong, Andrew Crombie, Alastair E Lacey, Mahmud T Morshed, Peter Karuso Org Biomol Chem . 2018 Apr 25;16(16):3038-3051. doi: 10.1039/c8ob00545a.
Reinvestigating antibiotic scaffolds that were identified during the Golden Age of antibiotic discovery, but have long since been "forgotten", has proven to be an effective strategy for delivering next-generation antibiotics capable of combatting multidrug-resistant superbugs. In this study, we have revisited the trichloro-substituted depsidone, nidulin, as a selective and unexploited antibiotic lead produced by the fungus Aspergillus unguis. Manipulation of halide ion concentration proved to be a powerful tool for modulating secondary metabolite production and triggering quiescent pathways in A. unguis. Supplementation of the culture media with chloride resulted in a shift in co-metabolite profile to dichlorounguinols and nornidulin at the expense of the non-chlorinated parent, unguinol. Surprisingly, only marginal enhancement of nidulin was observed, suggesting O-methylation may be rate-limiting. Similarly, supplementation of the media with bromide led to the production of the corresponding bromo-analogues, but also resulted in a novel family of depsides, the unguidepsides. Unexpectedly, depletion of chloride from the media halted the biosynthesis of the non-chlorinated parent compound, unguinol, and redirected biosynthesis to a novel family of ring-opened analogues, the unguinolic acids. Supplementation of the media with a range of unnatural salicylic acids failed to yield the corresponding nidulin analogues, suggesting the compounds may be biosynthesised by a single polyketide synthase. In total, 12 new and 11 previously reported nidulin analogues were isolated, characterised and assayed for in vitro activity against a panel of bacteria, fungi and mammalian cells, providing a comprehensive structure-activity profile for the nidulin scaffold.
3. Depsidone Derivatives and a Cyclopeptide Produced by Marine Fungus Aspergillus unguis under Chemical Induction and by Its Plasma Induced Mutant
Yi Zhang, Ying-Ying Nie, Jing-Ming Yang, Wen-Cong Yang, Hai-Yan Bao, Peng-Zhi Hong, Ya-Yue Liu Molecules . 2018 Sep 3;23(9):2245. doi: 10.3390/molecules23092245.
A new depsidone derivative (1), aspergillusidone G, was isolated from a marine fungusAspergillus unguis, together with eight known depsidones (2‒9) and a cyclic peptide (10): agonodepside A (2), nornidulin (3), nidulin (4), aspergillusidone F (5), unguinol (6), aspergillusidone C (7), 2-chlorounguinol (8), aspergillusidone A (9), and unguisin A (10). Compounds1‒4and7‒9were obtained from the plasma induced mutant of this fungus, while5,6, and10were isolated from the original strain under chemical induction. Their structures were identified using spectroscopic analysis, as well as by comparison with literature data. The HPLC fingerprint analysis indicates that chemical induction and plasma mutagenesis effectively influenced the secondary metabolism, which may be due to their regulation in the key steps in depsidone biosynthesis. In bioassays, compound9inhibited acetylcholinesterase (AChE) with IC50in 56.75 μM. Compounds1,5,7,8, and9showed moderate to strong activity towards different microbes. Compounds3,4, and5exhibited potent larvicidality against brine shrimp. In docking studies, higher negative CDOCKER interaction energy and richer strong interactions between AChE and9explained the greater activity of9compared to1. Chemical induction and plasma mutagenesis can be used as tools to expand the chemodiversity of fungi and obtain useful natural products.
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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 ╳
