5,7,3',4',5'-penthydroxy-3-methoxy flavone
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| Category | Others |
| Catalog number | BBF-04958 |
| CAS | 1486-67-5 |
| Molecular Weight | 332.26 |
| Molecular Formula | C16H12O8 |
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Description
5,7,3',4',5'-penthydroxy-3-methoxy flavone is an O-methylated flavonol found in the roots of Pteroxygonum giraldii.
Specification
| Synonyms | Annulatin; 3-O-methylmyricetin |
| IUPAC Name | 5,7-dihydroxy-3-methoxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one |
| Canonical SMILES | COC1=C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC(=C(C(=C3)O)O)O |
| InChI | InChI=1S/C16H12O8/c1-23-16-14(22)12-8(18)4-7(17)5-11(12)24-15(16)6-2-9(19)13(21)10(20)3-6/h2-5,17-21H,1H3 |
| InChI Key | XWTLYULBWZQAAZ-UHFFFAOYSA-N |
Properties
| Boiling Point | 741.2±60.0°C at 760 mmHg |
| Density | 1.8±0.1 g/cm3 |
Reference Reading
1. Biotransformation of 5,7-Methoxyflavones by Selected Entomopathogenic Filamentous Fungi
Mateusz Łużny, Tomasz Tronina, Ewa Kozłowska, Edyta Kostrzewa-Susłow, Tomasz Janeczko J Agric Food Chem. 2021 Apr 7;69(13):3879-3886. doi: 10.1021/acs.jafc.1c00136. Epub 2021 Mar 29.
5,7-Dimethoxyflavone, a chrysin derivative, occurs in many plants and shows very low toxicity, even at high doses. On the basis of this phenomenon, we biotransformed a series of methoxy-derivatives of chrysin, apigenin, and tricetin obtained by chemical synthesis. We used entomopathogenic fungal strains with the confirmed ability of simultaneous hydroxylation/demethylation and glycosylation of flavonoid compounds. Both the amount and the place of attachment of the methoxy group influenced the biotransformation rate and the product's amount nascent. Based on product and semi-product structures, it can be concluded that they are the result of cascading transformations. Only in the case of 5,7,3',4',5'-pentamethoxyflavone, the strains were able to attach a sugar molecule in place of the methoxy substituent to give 3'-O-β-d-(4″-O-methylglucopyranosyl)-5,7,4',5'-tetramethoxyflavone. However, we observed the tested strains' ability to selectively demethylate/hydroxylate the carbon C-3' and C-4' of ring B of the substrates used. The structures of four hydroxyl-derivatives were determined: 4'-hydroxy-5,7-dimethoxyflavone, 3'-hydroxy-5,7-dimethoxyflavone, 3'-hydroxy-5,7,4',5'-tetramethoxyflavone, and 5,7-dimethoxy-3',4'-dihydroxyflavone (5,7-dimethoxy-luteolin).
2. 3,5,7,3',4'-Pentamethoxyflavone Enhances the Barrier Function through Transcriptional Regulation of the Tight Junction in Human Intestinal Caco-2 Cells
Yunika Mayangsari, Natsumi Sugimachi, Wenxi Xu, Chinatsu Mano, Yuki Tanaka, Osamu Ueda, Tomohiro Sakuta, Yoshiharu Suzuki, Yoshinari Yamamoto, Takuya Suzuki J Agric Food Chem. 2021 Sep 8;69(35):10174-10183. doi: 10.1021/acs.jafc.1c04295. Epub 2021 Aug 27.
The intestinal tight junction (TJ) barrier plays a pivotal role in the regulation of intestinal homeostasis. This study investigated the effects of 3,5,7,3',4'-pentamethoxyflavone (PMF), a major polymethoxyflavone found in black ginger, on TJ barrier regulation using intestinal Caco-2 cells. PMF treatment enhanced the TJ barrier integrity in Caco-2 cells, indicated by increased transepithelial electrical resistance (control, 1261 ± 36 Ω·cm2; 100 μM PMF, 1383 ± 55 Ω·cm2 at 48 h, p < 0.05) and decreased permeability to fluorescein-conjugated dextran (control, 24.2 ± 1.8 pmol/(cm2 × h); 100 μM PMF, 18.6 ± 1.0 pmol/(cm2 × h), p < 0.05). Immunoblot analysis revealed that PMF increased the cytoskeletal association and cellular expression of the TJ proteins, zonula occludens-1, claudin-3, and claudin-4 (e.g., occludin; control, 1.00 ± 0.2; 100 μM PMF, 3.69 ± 0.86 at 48 h, p < 0.05). Quantitative reverse transcriptase-polymerase chain reaction analysis and a luciferase promoter assay showed that PMF enhanced the transcription of occludin, claudin-3, and claudin-4. The promoter assay with site-directed mutagenesis indicated that PMF-induced occludin and claudin-3 transcription was mediated by transcription factors, KLF5 and EGR1, respectively, while PMF activated claudin-4 transcription through GATA1 and AP1. Taken together, the transcriptional regulation of TJ proteins is involved in PMF-mediated promotion of the intestinal barrier in vitro.
3. 5,7,3',4'-tetramethoxyflavone ameliorates cholesterol dysregulation by mediating SIRT1/FOXO3a/ABCA1 signaling in osteoarthritis chondrocytes
Fang Peng, Xianhua Huang, Weimei Shi, Yaosheng Xiao, Qi Jin, Linfu Li, Daohua Xu, Longhuo Wu Future Med Chem. 2021 Dec;13(24):2153-2166. doi: 10.4155/fmc-2021-0247. Epub 2021 Oct 5.
Dyslipidemia has been associated with the development of osteoarthritis. Our previous study found that 5,7,3',4'-tetramethoxyflavone (TMF) exhibited protective activities against the pathological changes of osteoarthritis. Aim: To investigate the roles of TMF in regulating ABCA1-mediated cholesterol metabolism. Methods: Knockdown and overexpression were employed to study gene functions. Protein-protein interaction was investigated by co-immunoprecipitation, and the subcellular locations of proteins were studied by immunofluorescence. Results: IL-1β decreased ABCA1 expression and induced apoptosis. Therapeutically, TMF ameliorated the effects of IL-1β. FOXO3a knockdown expression abrogated the effects of TMF, and FOXO3a overexpression increased ABCA1 expression by interacting with LXRα. TMF promoted FOXO3a nuclear translocation by activating SIRT1 expression. Conclusions: TMF ameliorates cholesterol dysregulation by increasing the expression of FOXO3a/LXRα/ABCA1 signaling through SIRT1 in C28/I2 cells.
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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
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
