Phomaligol A
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| Category | Bioactive by-products |
| Catalog number | BBF-04377 |
| CAS | 152204-32-5 |
| Molecular Weight | 284.31 |
| Molecular Formula | C14H20O6 |
| Purity | ≥98% |
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Description
Phomaligol A is an antibacterial metabolite produced from marine-derived fungus Aspergillus flavus.
Specification
| Synonyms | Butanoic acid, 2-methyl-, (1R,5R)-5-hydroxy-4-methoxy-1,5-dimethyl-2,6-dioxo-3-cyclohexen-1-yl ester, (2S)- |
| Storage | Store at 2-8°C |
| IUPAC Name | [(1R,5R)-5-hydroxy-4-methoxy-1,5-dimethyl-2,6-dioxocyclohex-3-en-1-yl] (2S)-2-methylbutanoate |
| Canonical SMILES | CCC(C)C(=O)OC1(C(=O)C=C(C(C1=O)(C)O)OC)C |
| InChI | InChI=1S/C14H20O6/c1-6-8(2)11(16)20-14(4)9(15)7-10(19-5)13(3,18)12(14)17/h7-8,18H,6H2,1-5H3/t8-,13+,14+/m0/s1 |
| InChI Key | DWJRXSZPSOQYDZ-MCCGJVOXSA-N |
Properties
| Appearance | Oily Matter |
| Antibiotic Activity Spectrum | Bacteria |
| Boiling Point | 434.2±45.0°C (Predicted) |
| Density | 1.20±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Chloroform |
Reference Reading
1. Two New Phomaligols from the Marine-Derived Fungus Aspergillus flocculosus and Their Anti-Neuroinflammatory Activity in BV-2 Microglial Cells
Byeoung-Kyu Choi, Duk-Yeon Cho, Dong-Kug Choi, Phan Thi Hoai Trinh, Hee Jae Shin Mar Drugs. 2021 Jan 27;19(2):65. doi: 10.3390/md19020065.
Two new phomaligols, deketo-phomaligol A (1) and phomaligol E (2), together with six known compounds (3-8) were isolated from the culture broth of the marine-derived fungus Aspergillus flocculosus. Compound 1 was first isolated as a phomaligol derivative possessing a five-membered ring. The structures and absolute configurations of the new phomaligols were determined by detailed analyses of mass spectrometry (MS), nuclear magnetic resonance (NMR) data, optical rotation values and electronic circular dichroism (ECD). In addition, the absolute configurations of the known compounds 3 and 4 were confirmed by chemical oxidation and comparison of optical rotation values. Isolated compounds at a concentration of 100 μM were screened for inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-induced BV-2 microglial cells. Among the compounds, 4 showed moderate anti-neuroinflammatory effects with an IC50 value of 56.6 μM by suppressing the production of pro-inflammatory mediators in activated microglial cells without cytotoxicity.
2. Phomaligols F-I, polyoxygenated cyclohexenone derivatives from marine-derived fungus Aspergillus flavus BB1
Xiao-Jing Liu, Hou-Jin Li, Wen-Zhe Ma, Fu-Ming Zhang, Meng-Yang Xu, Taifo Mahmud, Wen-Jian Lan Bioorg Chem. 2021 Oct;115:105269. doi: 10.1016/j.bioorg.2021.105269. Epub 2021 Aug 16.
By tracing the 13C NMR resonances for carbonyls and enols, four new oxidized phomaligol derivatives, phomaligols F-I (1-4), along with seven known compounds (5-11) were isolated from the culture of the fungus Aspergillus flavus BB1 isolated from the marine shellfish Meretrix meretrix collected on Hailing Island, Yangjiang, China. The chemical structures and the absolute configurations of the new compounds were elucidated by MS, NMR, ECD, optical rotation, and 13C NMR calculations. Compounds 1 and 2 represent the first examples of phomaligol derivatives that contain an unusual bicyclic skeleton. All isolated compounds were tested for their cytotoxic activity. Among them, sporogen-AO 1 (8) showed potent inhibitory activity against the cancer cell lines A549, H1299, SK-BR-3, and HCT116 with IC50 values of 0.13, 0.78, 1.19, and 1.32 μM, respectively. Phomaligol G (2) displayed cytotoxic activity against the A549 and H1299 cell lines with IC50 values of 46.86 and 51.87 μM respectively. Additionally, phomaligol H (3) demonstrated cytotoxic activity against the A549 cell line with an IC50 value of 65.53 μM. Mechanistic studies of compound 8 showed that it induced apoptosis of HCT116 cells in a dose-dependent manner.
3. A new cyclohexenone from the tin mine tailings-derived fungus Aspergillus flavus YIM DT 10012
Wei-Xun Chunyu, Jiang-Yuan Zhao, Zhang-Gui Ding, Xiu-Lin Han, Yong-Xia Wang, Jian-Hai Ding, Fei Wang, Ming-Gang Li, Meng-Liang Wen Nat Prod Res. 2019 Jan;33(1):113-116. doi: 10.1080/14786419.2018.1431636. Epub 2018 Jan 29.
A new cyclohexenone, named phomaligol D (1), together with two known compounds, kojic acid (2) and phomaligol A (3) were isolated from the tin mine tailings-derived fungus Aspergillus flavus YIM DT 10012. Their structures were elucidated by detailed analysis of spectroscopic data.
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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 ╳
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