FlavoglaucinCAS# 523-73-9 |
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Cas No. | 523-73-9 | SDF | Download SDF |
PubChem ID | 119037 | Appearance | Powder |
Formula | C19H28O3 | M.Wt | 304.43 |
Type of Compound | Phenols | Storage | Desiccate at -20°C |
Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
Chemical Name | 2-heptyl-3,6-dihydroxy-5-(3-methylbut-2-enyl)benzaldehyde | ||
SMILES | CCCCCCCC1=C(C=C(C(=C1C=O)O)CC=C(C)C)O | ||
Standard InChIKey | RGRXZGKXEJHPQQ-UHFFFAOYSA-N | ||
Standard InChI | InChI=1S/C19H28O3/c1-4-5-6-7-8-9-16-17(13-20)19(22)15(12-18(16)21)11-10-14(2)3/h10,12-13,21-22H,4-9,11H2,1-3H3 | ||
General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
Description | 1. Flavoglaucin has anti-inflammatory effects, it shows inhibitory effects on inflammatory mediators via the induction of heme oxygenase-1 in lipopolysaccharide-stimulated RAW264.7 macrophages. 2. Flavoglaucin exhibits significant inhibitory effects on PTP1B, the IC50 value of 13.4, micrometer. 3. Flavoglaucin shows good binding affinity for human opioid or cannabinoid receptors. 4. Flavoglaucin can inhibit mouse skin tumor promotion in a two-stage carcinogenesis test and appear to be an antitumor promoter. 5. Flavoglaucin exhibits a significant radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with theIC(50) value of 11.3 microM. |
Targets | NO | PGE | NOS | COX | TNF-α | IL Receptor | NF-kB | HO-1 | Nrf2 |
Flavoglaucin Dilution Calculator
Flavoglaucin Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 3.2848 mL | 16.4241 mL | 32.8483 mL | 65.6965 mL | 82.1207 mL |
5 mM | 0.657 mL | 3.2848 mL | 6.5697 mL | 13.1393 mL | 16.4241 mL |
10 mM | 0.3285 mL | 1.6424 mL | 3.2848 mL | 6.5697 mL | 8.2121 mL |
50 mM | 0.0657 mL | 0.3285 mL | 0.657 mL | 1.3139 mL | 1.6424 mL |
100 mM | 0.0328 mL | 0.1642 mL | 0.3285 mL | 0.657 mL | 0.8212 mL |
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. |
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A new radical scavenging anthracene glycoside, asperflavin ribofuranoside, and polyketides from a marine isolate of the fungus microsporum.[Pubmed:16755063]
Chem Pharm Bull (Tokyo). 2006 Jun;54(6):882-3.
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). 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.
Evaluation of flavoglaucin, its derivatives and pyranonigrins produced by molds used in fermented foods for inhibiting tumor promotion.[Pubmed:20460698]
Biosci Biotechnol Biochem. 2010;74(5):1120-2.
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. Flavoglaucin and such a derivative as isodihydroauroglaucin inhibited mouse skin tumor promotion in a two-stage carcinogenesis test and appear to be antitumor promoters.
Inhibitory effects of benzaldehyde derivatives from the marine fungus Eurotium sp. SF-5989 on inflammatory mediators via the induction of heme oxygenase-1 in lipopolysaccharide-stimulated RAW264.7 macrophages.[Pubmed:25535073]
Int J Mol Sci. 2014 Dec 19;15(12):23749-65.
Two benzaldehyde derivatives, Flavoglaucin (1) and isotetrahydro-auroglaucin (2), were isolated from the marine fungus Eurotium sp. SF-5989 through bioassay- and 1H NMR-guided investigation. In this study, we evaluated the anti-inflammatory effects of these compounds in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. We demonstrated that compounds 1 and 2 markedly inhibited LPS-induced nitric oxide (NO) and prostaglandin E2 (PGE2) production by suppressing inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein expression without affecting cell viability. We also demonstrated that the compounds reduced the secretion of pro-inflammatory cytokines such as tumor necrosis factor-alpha (TNF-alpha), interleukin-1beta (IL-1beta) and interleukin-6 (IL-6). Furthermore, compounds 1 and 2 inhibited LPS-induced nuclear factor-kappaB (NF-kappaB) activation by suppressing phosphorylation of IkappaB (IkappaB). These results indicated that the anti-inflammatory effects of these benzaldehyde derivatives in LPS-stimulated RAW264.7 macrophages were due to the inactivation of the NF-kappaB pathway. In addition, compounds 1 and 2 induced heme oxygenase-1 (HO-1) expression through the nuclear transcription factor-E2-related factor 2 (Nrf2) translocation. The inhibitory effects of compounds 1 and 2 on the production of pro-inflammatory mediators and on NF-kappaB binding activity were reversed by HO-1 inhibitor tin protoporphyrin (SnPP). Thus, the anti-inflammatory effects of compounds 1 and 2 also correlated with their ability of inducing HO-1 expression.
Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from the fungus Eurotium repens.[Pubmed:21667972]
J Nat Prod. 2011 Jul 22;74(7):1636-9.
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. 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.
PTP1B inhibitory secondary metabolites from marine-derived fungal strains Penicillium spp. and Eurotium sp.[Pubmed:23770564]
J Microbiol Biotechnol. 2013 Sep 28;23(9):1206-11.
The selective inhibition of PTP1B has been widely recognized as a potential drug target for the treatment of type 2 diabetes and obesity. In the course of screening for PTP1B inhibitory fungal metabolites, the organic extracts of several fungal species isolated from marine environments were found to exhibit significant inhibitory effects, and the bioassay-guided investigation of these extracts resulted in the isolation of fructigenine A (1), cyclopenol (2), echinulin (3), Flavoglaucin (4), and viridicatol (5). The structures of these compounds were determined mainly by analysis of NMR and MS data. These compounds inhibited PTP1B activity with 50% inhibitory concentration values of 10.7, 30.0, 29.4, 13.4, and 64.0 micrometer, respectively. Furthermore, the kinetic analysis of PTP1B inhibition by compounds 1 and 5 suggested that compound 1 inhibited PTP1B activity in a noncompetitive manner, whereas compound 5 inhibited PTP1B activity in a competitive manner.