Sulochrin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04071 |
| CAS | 519-57-3 |
| Molecular Weight | 332.30 |
| Molecular Formula | C17H16O7 |
| Purity | >99% by HPLC |
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Description
Sulochrin is a fungal metabolite isolated from Aspergillus and Penicillium. It has anti-allergic, anti-angiogenic and anti-viral activities. It is an anti-angiogenic agent that can inhibit VEGF, thereby inhibiting the capillary-like formation of human umbilical vein endothelial cells. It also inhibits the activation and chemotaxis of eosinophils.
Specification
| Storage | Store at -20°C |
| IUPAC Name | methyl 2-(2,6-dihydroxy-4-methylbenzoyl)-5-hydroxy-3-methoxybenzoate |
| Canonical SMILES | CC1=CC(=C(C(=C1)O)C(=O)C2=C(C=C(C=C2OC)O)C(=O)OC)O |
| InChI | InChI=1S/C17H16O7/c1-8-4-11(19)15(12(20)5-8)16(21)14-10(17(22)24-3)6-9(18)7-13(14)23-2/h4-7,18-20H,1-3H3 |
| InChI Key | YJRLSCDUYLRBIZ-UHFFFAOYSA-N |
| Source | Aspergillus terreus |
Properties
| Appearance | Pale Yellow Solid |
| Antibiotic Activity Spectrum | viruses |
| Boiling Point | 576.3°C at 760 mmHg |
| Density | 1.378 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Reference Reading
1. The effect of viscosity, friction, and sonication on the morphology and metabolite production from Aspergillus terreus ATCC 20542
Muhamad Hafiz Abd Rahim, Hanan Hasan, Hanis H Harith, Ali Abbas Bioprocess Biosyst Eng. 2017 Dec;40(12):1753-1761. doi: 10.1007/s00449-017-1830-y. Epub 2017 Sep 6.
This study investigates the effects of viscosity, friction, and sonication on the morphology and the production of lovastatin, (+)-geodin, and sulochrin by Aspergillus terreus ATCC 20542. Sodium alginate and gelatine were used to protect the fungal pellet from mechanical force by increasing the media viscosity. Sodium alginate stimulated the production of lovastatin by up to 329.0% and sulochrin by 128.7%, with inhibitory effect on (+)-geodin production at all concentrations used. However, the use of gelatine to increase viscosity significantly suppressed lovastatin, (+)-geodin, and sulochrin's production (maximum reduction at day 9 of 42.7, 60.8, and 68.3%, respectively), which indicated that the types of chemical play a major role in metabolite production. Higher viscosity increased both pellet biomass and size in all conditions. Friction significantly increased (+)-geodin's titre by 1527.5%, lovastatin by 511.1%, and sulochrin by 784.4% while reducing pellet biomass and size. Conversely, sonication produced disperse filamentous morphology with significantly lower metabolites. Sodium alginate-induced lovastatin and sulochrin production suggest that these metabolites are not affected by viscosity; rather, their production is affected by the specific action of certain chemicals. In contrast, low viscosity adversely affected (+)-geodin's production, while pellet disintegration can cause a significant production of (+)-geodin.
2. Sulochrins and alkaloids from a fennel endophyte Aspergillus sp. FVL2
Mohamed Shaaban, Ahmed S Abdel-Razek, Viola Previtali, Mads Hartvig Clausen, Charlotte H Gotfredsen, Hartmut Laatsch, Ling Ding Nat Prod Res. 2021 Dec 6;1-11. doi: 10.1080/14786419.2021.2005054. Online ahead of print.
The fungal endophyte Aspergillus sp. strain FVL2, isolated from the traditional medicinal fennel plant, Foeniculum vulgare, was investigated for secondary metabolites. Fermentation on rice medium followed by chromatographic separation delivered three new natural products, 7-demethyl-neosulochrin (1), fumigaclavine I (3) and N-benzoyl-tryptophan (6) together with further 14 known metabolites, 1-O-methyl-sulochrin-4'-sulfate, questin, laccaic acid, isorhodoptilometrin, fumigaclavine A, fumigaclavine C, fumitremorgin C, fumigaquinazoline C, tryptoquivaline J, trypacidin, 3'-O-demethyl-sulochrin, 1-O-methyl-sulochrin, protocatechuic acid, and vermelone. The chemical structures of the new metabolites were determined by NMR spectroscopy and ESI HR mass spectrometry. For fumigaclavine I, we observed the partial deuterium transfer from the solvent to the enol form with a remarkable high stereo selectivity. The discovery of the new seco-anthraquinone 7-demethyl-neosulochrin (1) revealed a second type of ring cleavage by a questin oxygenase. The discovery of diverse secondary metabolites broadens the chemical space of Aspergillus.
3. Polyketides from the marine-derived fungus Aspergillus falconensis: In silico and in vitro cytotoxicity studies
Dina H El-Kashef, Fadia S Youssef, Irene Reimche, Nicole Teusch, Werner E G Müller, Wenhan Lin, Marian Frank, Zhen Liu, Peter Proksch Bioorg Med Chem. 2021 Jan 1;29:115883. doi: 10.1016/j.bmc.2020.115883. Epub 2020 Nov 21.
Fermentation of the marine-derived fungus Aspergillus falconensis, isolated from sediment collected from the Red Sea, Egypt on solid rice medium containing 3.5% NaCl yielded a new dibenzoxepin derivative (1) and a new natural isocoumarin (2) along with six known compounds (3-8). Changes in the metabolic profile of the fungus were induced by replacing NaCl with 3.5% (NH4)2SO4 that resulted in the accumulation of three further known compounds (9-11), which were not detected when the fungus was cultivated in the presence of NaCl. The structures of the new compounds were elucidated by HRESIMS and 1D/2D NMR as well as by comparison with the literature. Molecular docking was conducted for all isolated compounds on crucial enzymes involved in the formation, progression and metastasis of cancer which included human cyclin-dependent kinase 2 (CDK-2), human DNA topoisomerase II (TOP-2) and matrix metalloproteinase 13 (MMP-13). Diorcinol (7), sulochrin (9) and monochlorosulochrin (10) displayed notable stability within the active pocket of CDK-2 with free binding energy (ΔG) equals to -25.72, -25.03 and -25.37 Kcal/mol, respectively whereas sulochrin (9) exerted the highest fitting score within MMP-13 active center (ΔG = -33.83 Kcal/mol). In vitro cytotoxic assessment using MTT assay showed that sulochrin (9) exhibited cytotoxic activity versus L5178Y mouse lymphoma cells with an IC50 value of 5.1 µM and inhibition of migration of MDA-MB 231 breast cancer cells at a concentration of 70 µM.
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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 ╳
