| Description: |
Flavoglaucin exhibits significant inhibitory effects on PTP1B, the IC50 value of 13.4, micrometer; it also shows good binding affinity for human opioid or cannabinoid receptors. Flavoglaucin appears to be an antitumor promoter, it also has anti-inflammatory effects, it shows inhibitory effects on inflammatory mediators via the induction of heme oxygenase-1 in lipopolysaccharide-stimulated RAW264.7 macrophages. Flavoglaucin exhibits a significant radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with theIC(50) value of 11.3 microM. |
| In vitro: |
| J Nat Prod. 2011 Jul 22;74(7):1636-9. | | Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from the fungus Eurotium repens.[Pubmed: 21667972] |
METHODS AND RESULTS:
Bioassay-guided fractionation of the fungus Eurotium repens resulted in the isolation of two new benzyl derivatives, (E)-2-(hept-1-enyl)-3-(hydroxymethyl)-5-(3-methylbut-2-enyl)benzene-1,4-diol (1) and (E)-4-(hept-1-enyl)-7-(3-methylbut-2-enyl)-2,3-dihydrobenzofuran-2,5-diol (2), along with seven known compounds (3-9) including five benzaldehyde compounds, Flavoglaucin (3), tetrahydroauroglaucin (4), dihydroauroglaucin (5), auroglaucin (6), and 2-(2',3-epoxy-1',3'- heptadienyl)-6-hydroxy-5-(3-methyl-2-butenyl)benzaldehyde (7), one diketopiperazine alkaloid, echinulin (8), and 5,7-dihydroxy-4-methylphthalide (9). The chemical structures of these compounds were established on the basis of extensive 1D and 2D NMR and HRMS data.
CONCLUSIONS:
Compounds 1-4 and 6 showed good binding affinity for human opioid or cannabinoid receptors. These findings have important implications for psychoactive studies with this class of compounds. | | Biosci Biotechnol Biochem. 2010;74(5):1120-2. | | Evaluation of flavoglaucin, its derivatives and pyranonigrins produced by molds used in fermented foods for inhibiting tumor promotion.[Pubmed: 20460698] |
METHODS AND RESULTS:
Flavoglaucin, its derivatives, and pyranonigrins, which are antioxidants produced by the molds used in fermented foods, were examined for their inhibition of tumor promotion by the Epstein-Barr virus early antigen activation test. Flavoglaucin and its derivatives exhibited high activity.
CONCLUSIONS:
Flavoglaucin and such a derivative as isodihydroauroglaucin inhibited mouse skin tumor promotion in a two-stage carcinogenesis test and appear to be antitumor promoters. | | Chem Pharm Bull (Tokyo). 2006 Jun;54(6):882-3. | | A new radical scavenging anthracene glycoside, asperflavin ribofuranoside, and polyketides from a marine isolate of the fungus microsporum.[Pubmed: 16755063] |
METHODS AND RESULTS:
A new anthracene glycoside, asperflavin ribofuranoside (1), and the previously described polyketides, Flavoglaucin (2), isodihydroauroglaucin (3), and citrinin (4) have been isolated from the marine-derived fungus Microsporum sp. The structure and absolute stereochemistry of a new compound (1) was assigned on the basis of physicochemical data. Compounds 1-3 exhibited a significant radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with IC(50) values of 14.2, 11.3, and 11.5 microM, respectively, which are more potent than the positive control, ascorbic acid (IC(50), 20 microM).
CONCLUSIONS:
Compound 1 also showed a moderate antibacterial activity against the methicillin-resistant and multidrug-resistant Staphylococcus aureus (MRSA and MDRSA) with MIC value of 50 microg/ml. |
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