Unguinol
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04523 |
| CAS | 36587-59-4 |
| Molecular Weight | 326.34 |
| Molecular Formula | C19H18O5 |
| Purity | ≥95% |
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Description
Unguinol is a metabolite of the fungi Aspergillus unguis and Aspergillus nidulans. It has been found to be an active growth promotant in animals, in particular, monogastric animals such as chickens. It is an inhibitor of pyruvate phosphate dikinase (PPDK).
Specification
| Synonyms | 3,8-Dihydroxy-1,9-dimethyl-6-(1-methyl-1-propenyl)-11H-dibenzo[b,e][1,4]dioxepin-11-one; Yasimin |
| Storage | Store at -20°C |
| IUPAC Name | 1-[(E)-but-2-en-2-yl]-3,9-dihydroxy-4,7-dimethylbenzo[b][1,4]benzodioxepin-6-one |
| Canonical SMILES | CC=C(C)C1=CC(=C(C2=C1OC3=C(C(=CC(=C3)O)C)C(=O)O2)C)O |
| InChI | InChI=1S/C19H18O5/c1-5-9(2)13-8-14(21)11(4)17-18(13)23-15-7-12(20)6-10(3)16(15)19(22)24-17/h5-8,20-21H,1-4H3/b9-5+ |
| InChI Key | ZPPIKBUIYSSQEH-WEVVVXLNSA-N |
Properties
| Appearance | Solid |
| Boiling Point | 552.2±50.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in DMF, DMSO, Ethanol, Methanol |
Reference Reading
1. Semisynthesis and biological evaluation of a focused library of unguinol derivatives as next-generation antibiotics
Andrew M Piggott, Ernest Lacey, Darren J Trott, Hang T Nguyen, Daniel Vuong, Stephen W Page, Andrew Crombie, Abiodun D Ogunniyi, Mahmud T Morshed Org Biomol Chem . 2021 Feb 7;19(5):1022-1036. doi: 10.1039/d0ob02460k.
In this study, we report the semisynthesis and in vitro biological evaluation of thirty-four derivatives of the fungal depsidone antibiotic, unguinol. Initially, the semisynthetic modifications were focused on the two free hydroxy groups (3-OH and 8-OH), the three free aromatic positions (C-2, C-4 and C-7), the butenyl side chain and the depsidone ester linkage. Fifteen first-generation unguinol analogues were synthesised and screened against a panel of bacteria, fungi and mammalian cells to formulate a basic structure activity relationship (SAR) for the unguinol pharmacophore. Based on the SAR studies, we synthesised a further nineteen second-generation analogues, specifically aimed at improving the antibacterial potency of the pharmacophore. In vitro antibacterial activity testing of these compounds revealed that 3-O-(2-fluorobenzyl)unguinol and 3-O-(2,4-difluorobenzyl)unguinol showed potent activity against both methicillin-susceptible and methicillin-resistant Staphylococcus aureus (MIC 0.25-1 μg mL-1) and are promising candidates for further development in vivo.
2. Screening marine fungi for inhibitors of the C4 plant enzyme pyruvate phosphate dikinase: unguinol as a potential novel herbicide candidate
Cherie A Motti, David G Bourne, Andrew Muirhead, James N Burnell, Catherine H Liptrot, Dianne S Haines, Dianne M Tapiolas, Lyndon E Llewellyn, Shilo Ludke, Jason R Doyle Appl Environ Microbiol . 2007 Mar;73(6):1921-7. doi: 10.1128/AEM.02479-06.
A total of 2,245 extracts, derived from 449 marine fungi cultivated in five types of media, were screened against the C(4) plant enzyme pyruvate phosphate dikinase (PPDK), a potential herbicide target. Extracts from several fungal isolates selectively inhibited PPDK. Bioassay-guided fractionation of one isolate led to the isolation of the known compound unguinol, which inhibited PPDK with a 50% inhibitory concentration of 42.3 +/- 0.8 muM. Further kinetic analysis revealed that unguinol was a mixed noncompetitive inhibitor of PPDK with respect to the substrates pyruvate and ATP and an uncompetitive inhibitor of PPDK with respect to phosphate. Unguinol had deleterious effects on a model C(4) plant but no effect on a model C(3) plant. These results indicate that unguinol inhibits PPDK via a novel mechanism of action which also translates to an herbicidal effect on whole plants.
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 ╳
