Javanicin
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| Category | Antibiotics |
| Catalog number | BBF-01881 |
| CAS | 476-45-9 |
| Molecular Weight | 290.27 |
| Molecular Formula | C15H14O6 |
| Purity | ≥98% by HPLC |
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Description
It is produced by the strain of Fusarium javanicum, etc. Javanicin is resistant to gram-positive bacteria and mycobacteria.
Specification
| Synonyms | 5,8-Dihydroxy-6-methoxy-3-(2-oxopropyl)-1,4-naphthalenedione; 3-Acetonyl-5,8-dihydroxy-6-methoxy-2-methyl-1,4-naphthoquinone; BRN 2296055 |
| Storage | 2-8°C under seal save, placed in ventilated, dry environment |
| IUPAC Name | 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione |
| Canonical SMILES | CC1=C(C(=C2C(=C1O)C(=O)C=C(C2=O)OC)O)CC(=O)C |
| InChI | InChI=1S/C15H14O6/c1-6(16)4-8-7(2)13(18)11-9(17)5-10(21-3)15(20)12(11)14(8)19/h5,18-19H,4H2,1-3H3 |
| InChI Key | UHPMCKVQTMMPCG-UHFFFAOYSA-N |
Properties
| Appearance | Copper Flake Crystalline |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria |
| Boiling Point | 616.5°C at 760 mmHg |
| Melting Point | 207.5-208°C |
| Density | 1.43 g/cm3 |
Reference Reading
1. Production and Selectivity of Key Fusarubins from Fusarium solani due to Media Composition
Sebastian Birkedal Kristensen, Tobias Bruun Pedersen, Mikkel Rank Nielsen, Reinhard Wimmer, Jens Muff, Jens Laurids Sørensen Toxins (Basel). 2021 May 25;13(6):376. doi: 10.3390/toxins13060376.
Natural products display a large structural variation and different uses within a broad spectrum of industries. In this study, we investigate the influence of carbohydrates and nitrogen sources on the production and selectivity of production of four different polyketides produced by Fusarium solani, fusarubin, javanicin, bostrycoidin and anhydrofusarubin. We introduce four different carbohydrates and two types of nitrogen sources. Hereafter, a full factorial design was applied using combinations of three levels of sucrose and three levels of the two types of nitrogen. Each combination displayed different selectivity and production yields for all the compounds of interest. Response surface design was utilized to investigate possible maximum yields for the surrounding combinations of media. It was also shown that the maximum yields were not always the ones illustrating high selectivity, which is an important factor for making purification steps easier. We visualized the production over time for one of the media types, illustrating high yields and selectivity.
2. Fungicidal Activity of Recombinant Javanicin against Cryptococcus neoformans Is Associated with Intracellular Target(s) Involved in Carbohydrate and Energy Metabolic Processes
Santhasiri Orrapin, Sittiruk Roytrakul, Narumon Phaonakrop, Siriwan Thaisakun, Khajornsak Tragoolpua, Amornrat Intorasoot, Suzanne McGill, Richard Burchmore, Sorasak Intorasoot Molecules. 2021 Nov 20;26(22):7011. doi: 10.3390/molecules26227011.
The occurrence of Cryptococcus neoformans, the human fungal pathogen that primarily infects immunocompromised individuals, has been progressing at an alarming rate. The increased incidence of infection of C. neoformans with antifungal drugs resistance has become a global concern. Potential antifungal agents with extremely low toxicity are urgently needed. Herein, the biological activities of recombinant javanicin (r-javanicin) against C. neoformans were evaluated. A time-killing assay was performed and both concentration- and time-dependent antifungal activity of r-javanicin were indicated. The inhibitory effect of the peptide was initially observed at 4 h post-treatment and ultimately eradicated within 36 to 48 h. Fungal outer surface alteration was characterized by the scanning electron microscope (SEM) whereas a negligible change with slight shrinkage of external morphology was observed in r-javanicin treated cells. Confocal laser scanning microscopic analysis implied that the target(s) of r-javanicin is conceivably resided in the cell thereby allowing the peptide to penetrate across the membrane and accumulate throughout the fungal body. Finally, cryptococcal cells coped with r-javanicin were preliminarily investigated using label-free mass spectrometry-based proteomics. Combined with microscopic and proteomics analysis, it was clearly elucidated the peptide localized in the intracellular compartment where carbohydrate metabolism and energy production associated with glycolysis pathway and mitochondrial respiration, respectively, were principally interfered. Overall, r-javanicin would be an alternative candidate for further development of antifungal agents.
3. An efficient high-speed countercurrent chromatography method for preparative separation of javanicin from Fusarium solani, a fungus isolated from the fruiting body of the mushroom Trametes trogii
Ruyi Guo, Xu Cai, Qian Li, Yun Huang, Benke Chen, Ping Guan, Jintian Tang, Xianwei Zou Biomed Chromatogr. 2019 Sep;33(9):e4574. doi: 10.1002/bmc.4574. Epub 2019 Jul 15.
To develop an efficient method for large preparation of javanicin from Fusarium solani, a rapid and simple method by high-speed countercurrent chromatography was established based on average polarity (P' values) and partition coefficients (K values) of crude samples. A suitable solvent system for high-speed countercurrent chromatography was selected from many possible biphasic solvent systems. HSCCC was successfully applied to separate and purify javanicin, the main bioactive component of solid cultures of the fungus F. solani isolated from the fruiting body of Trametes trogii, with petroleum ether-ethyl acetate-methanol-water (4:3:2:1, v/v) as solvent system. A total amount of 40.6 mg of javanicin was obtained from 100 mg crude sample. The purity of javanicin was 92.2% with a recovery of 95.1%, as determined by high-performance liquid chromatrography. The molecular structure was identified primarily by NMR and MS methods. The results indicated that high-speed countercurrent chromatography could be a powerful technology for separating naphthoquinones from the solid cultures of the fungus F. solani. It is also of significance that the separation of javanicin from natural source was carried out for the first time utilizing high-speed countercurrent chromatography.
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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 ╳
