Deoxyfunicone
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| Category | Bioactive by-products |
| Catalog number | BBF-01458 |
| CAS | |
| Molecular Weight | 358.34 |
| Molecular Formula | C19H18O7 |
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Description
It is produced by the strain of Talararomyces flavus FKI-0076. Deoxyfunicone is an antifungal activity enhancer of Miconazole.
Specification
| Synonyms | Benzoic acid, 3,5-dimethoxy-2-[[4-oxo-6-[(1E)-1-propenyl]-4H-pyran-3-yl]carbonyl]-, methyl ester |
| IUPAC Name | methyl 3,5-dimethoxy-2-[4-oxo-6-[(E)-prop-1-enyl]pyran-3-carbonyl]benzoate |
| Canonical SMILES | CC=CC1=CC(=O)C(=CO1)C(=O)C2=C(C=C(C=C2OC)OC)C(=O)OC |
| InChI | InChI=1S/C19H18O7/c1-5-6-11-8-15(20)14(10-26-11)18(21)17-13(19(22)25-4)7-12(23-2)9-16(17)24-3/h5-10H,1-4H3/b6-5+ |
| InChI Key | TZXWWWSFTQHNBQ-AATRIKPKSA-N |
Properties
| Appearance | Light Yellow Powder |
| Melting Point | 127.5-128.5°C |
Reference Reading
1. Penifupyrone, a new cytotoxic funicone derivative from the endophytic fungus Penicillium sp. HSZ-43
Ming-Jun Chen, Yang-Wu Fu, Qun-Ying Zhou Nat Prod Res. 2014;28(19):1544-8. doi: 10.1080/14786419.2014.924932. Epub 2014 Jun 18.
Penifupyrone (1), a new funicone derivative, has been isolated from the endophytic fungus Penicillium sp. HSZ-43, along with three known analogues, funicone (2), deoxyfunicone (3) and 3-O-methylfunicone (4). These structures were identified by using spectroscopic methods, including UV, MS, 1D and 2D NMR experiments. The structure of 1 was confirmed by single-crystal X-ray diffraction analysis. All the isolated compounds were evaluated for cytotoxicity against human oral epidermoid carcinoma KB cells, and compound 1 exhibited moderate cytotoxic activity with IC50 value of 4.7 μM.
2. Anti-Inflammatory and Protein Tyrosine Phosphatase 1B Inhibitory Metabolites from the Antarctic Marine-Derived Fungal Strain Penicillium glabrum SF-7123
Tran Minh Ha, Dong-Cheol Kim, Jae Hak Sohn, Joung Han Yim, Hyuncheol Oh Mar Drugs. 2020 May 9;18(5):247. doi: 10.3390/md18050247.
A chemical investigation of the marine-derived fungal strain Penicillium glabrum (SF-7123) revealed a new citromycetin (polyketide) derivative (1) and four known secondary fungal metabolites, i.e, neuchromenin (2), asterric acid (3), myxotrichin C (4), and deoxyfunicone (5). The structures of these metabolites were identified primarily by extensive analysis of their spectroscopic data, including NMR and MS data. Results from the initial screening of anti-inflammatory effects showed that 2, 4, and 5 possessed inhibitory activity against the excessive production of nitric oxide (NO) in lipopolysaccharide (LPS)-stimulated BV2 microglial cells, with IC50 values of 2.7 µM, 28.1 µM, and 10.6 µM, respectively. Compounds 2, 4, and 5 also inhibited the excessive production of NO, with IC50 values of 4.7 µM, 41.5 µM, and 40.1 µM, respectively, in LPS-stimulated RAW264.7 macrophage cells. In addition, these compounds inhibited LPS-induced overproduction of prostaglandin E2 in both cellular models. Further investigation of the most active compound (2) revealed that these anti-inflammatory effects were associated with a suppressive effect on the over-expression of inducible nitric oxide synthase and cyclooxygenase-2. Finally, we showed that the anti-inflammatory effects of compound 2 were mediated via the downregulation of inflammation-related pathways such as those dependent on nuclear factor kappa B and p38 mitogen-activated protein kinase in LPS-stimulated BV2 and RAW264.7 cells. In the evaluation of the inhibitory effects of the isolated compounds on protein tyrosine phosphate 1B (PTP1B) activity, compound 4 was identified as a noncompetitive inhibitor of PTP1B, with an IC50 value of 19.2 µM, and compound 5 was shown to inhibit the activity of PTP1B, with an IC50 value of 24.3 µM, by binding to the active site of the enzyme. Taken together, this study demonstrates the potential value of marine-derived fungal isolates as a bioresource for bioactive compounds.
3. Funicone-related compounds, potentiators of antifungal miconazole activity, produced by Talaromycesflavus FKI-0076
Masayoshi Arai, Hiroshi Tomoda, Takako Okuda, Haiyan Wang, Noriko Tabata, Rokuro Masuma, Yuichi Yamaguchi, Satoshi Omura J Antibiot (Tokyo). 2002 Feb;55(2):172-80. doi: 10.7164/antibiotics.55.172.
Talaromyces flavus FKI-0076, a soil isolate, was found to produce compounds which reinforce the anti-Candida albicans activity of miconazole. Four structurally related compounds, a novel one, designated actofunicone, and the knowns deoxyfunicone, vermistatin and NG-012, were isolated from the culture broth by solvent extraction, ODS column chromatography and HPLC. The structure of actofunicone was elucidated as benzoic acid, 3,5-dimethoxy-2-[[4-oxo-6-(2-acetyloxy propyl)-4H-pyran-3-yl]carbonyl]-, methyl ester by various spectroscopic analyses including NMR experiments. These compounds potentiated the anti-C. albicans activity of miconazole, decreasing the IC50 value of miconazole from 19 microM to 1.6 approximately 3.7 microM in the presence of the funicones.
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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 ╳
