Questinol
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04459 |
| CAS | 35688-09-6 |
| Molecular Weight | 300.26 |
| Molecular Formula | C16H12O6 |
| Purity | 98.0% |
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Description
Questinol is obtained from the cultures of the fungus Talaromyces stipitatus KUFA 0207. It can inhibit the production of NO, PGE2 and pro-inflammatory cytokines, including TNF-α, IL-1β and IL-6. It displays anti-inflammatory effect in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. It also shows remarkable anti-obesity activity.
Specification
| Synonyms | 1,6-Dihydroxy-3-(hydroxymethyl)-8-methoxy-9,10-anthracenedione; 9,10-Anthracenedione, 1,6-dihydroxy-3-(hydroxymethyl)-8-methoxy-; Omega-Hydroxymethylemodin |
| Storage | Store at -20°C |
| IUPAC Name | 1,6-dihydroxy-3-(hydroxymethyl)-8-methoxyanthracene-9,10-dione |
| Canonical SMILES | COC1=C2C(=CC(=C1)O)C(=O)C3=CC(=CC(=C3C2=O)O)CO |
| InChI | InChI=1S/C16H12O6/c1-22-12-5-8(18)4-10-14(12)16(21)13-9(15(10)20)2-7(6-17)3-11(13)19/h2-5,17-19H,6H2,1H3 |
| InChI Key | SNBGJGNOQURXCI-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Crystal |
| Boiling Point | 630.5±55.0°C at 760 mmHg |
| Melting Point | 280-282°C |
| Density | 1.5±0.1 g/cm3 |
| Solubility | Soluble in Ethanol |
Reference Reading
1. Simultaneous Determination of 13 Constituents of Radix Polygoni Multiflori in Rat Plasma and Its Application in a Pharmacokinetic Study
Wenhao Cheng, Yinghui Li, Wei Yang, Siyang Wu, Mengmeng Wei, Yang Gao, Chen Kang, Shuofeng Zhang, Yingfei Li Int J Anal Chem. 2020 Mar 3;2020:4508374. doi: 10.1155/2020/4508374. eCollection 2020.
Radix Polygoni Multiflori (RPM) has been widely used to treat various diseases in Asian countries for many centuries. Although, stilbenes and anthraquinones, two major components of RPM, show various bioactive effects, it has been speculated that the idiosyncratic hepatotoxicity induced by RPM may be related to these constituents. However, information on the pharmacokinetics of stilbenes and anthraquinones at a subtoxic dose of RPM is limited. A simple and sensitive UPLC-MS/MS bioanalytical method for the simultaneous determination of 13 ingredients of RPM, including chrysophanol, emodin, aloe-emodin, rhein, physcion, questin, citreorosein, questinol, 2,3,5,4'-tetrahydroxystilbene-2-O-β-D-glucoside, torachrysone-8-O-glucoside, chrysophanol-8-O-β-D-glucoside, emodin-8-O-β-D-glucoside, and physcion-8-O-β-D-glucoside, in rat plasma was established. Acetonitrile was employed to precipitate the plasma with appropriate sensitivity and acceptable matrix effects. Chromatographic separation was performed using a waters HSS C18 column with a gradient elution using water and acetonitrile both containing 0.025% formic acid within a run time of 9 min. The constituents were detected in negative ionization mode using multiple reaction monitoring. The method was fully validated in terms of selectivity, linearity, accuracy, precision, recovery, matrix effects, and stability. The lower limit of quantitation of the analytes was 0.1-1 ng/mL. The intrabatch and interbatch accuracies were 87.1-109%, and the precision was within the acceptable limits. The method was applied to a pharmacokinetic study after oral administration of RPM extract to rats at a subtoxic dose of 36 g/kg.
2. Potential Antiviral Xanthones from a Coastal Saline Soil Fungus Aspergillus iizukae
Hui-Hui Kang, Huai-Bin Zhang, Mei-Jia Zhong, Li-Ying Ma, De-Sheng Liu, Wei-Zhong Liu, Hong Ren Mar Drugs. 2018 Nov 15;16(11):449. doi: 10.3390/md16110449.
Five new (1⁻5) and two known xanthones (6 and 7), one of the latter (6) obtained for the first time as a natural product, together with three known anthraquinones, questin, penipurdin A, and questinol, were isolated from the coastal saline soil-derived Aspergillus iizukae by application of an OSMAC (one strain many compounds) approach. Their structures were determined by interpretation of nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, as well as comparison of these data with those of related known compounds. Antiviral activity of xanthones 1-7 was evaluated through the cytopathic effect (CPE) inhibition assay, and compound 2 exhibited distinctly strong activity towards influenza virus (H1N1), herpes simplex virus types 1 (HSV-1) and 2 (HSV-2) with IC50 values of 44.6, 21.4, and 76.7 μM, respectively, which indicated that it was worth to further investigate it as a potential lead compound. The preliminary structure-activity relationship of the xanthones is discussed.
3. Metabolomic profiling and cytotoxic potential of three endophytic fungi of the genera Aspergillus, Penicillium and Fusarium isolated from Nigella sativa seeds assisted with docking studies
Nourhan Hisham Shady, Jianye Zhang, Sara Khalid Sobhy, Mohamed Hisham, Stefanie P Glaeser, Faisal Alsenani, Peter Kämpfer, Mo'men H El-Katatny, Usama Ramadan Abdelmohsen Nat Prod Res. 2022 Oct 28;1-6. doi: 10.1080/14786419.2022.2136660. Online ahead of print.
The main aim of our study is to investigate the anticancer potential of our cultivated entophytic fungal strains from Nigella sativa seeds. The strains were identified by sequencing of the partial 18S rRNA gene and the internal transcribed spacer (ITS) region as Aspergillus sp. (SA4), Penicillium sp. (SA5), and Fusarium sp. (SA6). We carried out metabolic profiling for three fungal strains to investigate their metabolites diversity. Profiling of the different extracts revealed their richness in diverse metabolites and consequently fourteen compounds (1-14) were annotated. In addition, the obtained extracts were examined against three cell lines HepG2, MCF-7 and Caco-2 showed activity with IC50 values in the range of 1.95-39.7 μg/mL. Finally, molecular docking study was performed showing questinol as the lowest glide binding score value (-5.925 kcal/mol) among all identified compounds. Our results showed Nigella sativa-associated endophytes as a promising source for further studies to look for anticancer secondary metabolites.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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