107657-60-3Relevant articles and documents
Flavonoid 3′-O-methyltransferase from rice: cDNA cloning, characterization and functional expression
Kim, Bong-Gyu,Lee, Youngshim,Hur, Hor-Gil,Lim, Yoongho,Ahn, Joong-Hoon
, p. 387 - 394 (2006)
Plant O-methyltransferases (OMTs) are known to be involved in methylation of plant secondary metabolites, especially phenylpropanoid and flavonoid compounds. An OMT, ROMT-9, was cloned and characterized from rice using a reverse transcriptase polymerase chain reaction (RT-PCR). The blast results for ROMT-9 showed a 73% identity with caffeic acid OMTs from maize and Triticum aestivum. ROMT-9 was expressed in Escherichia coli and its recombinant protein was purified using affinity chromatography. It was then tested for its ability to transfer the methyl group of S-adenosyl-l-methionine to the flavonoid substrates, eriodictyol, luteolin, quercetin, and taxifolin, all of which have a 3′-hydroxyl functional group. The reaction products were analyzed using TLC, HPLC, HPLC/MS, and NMR spectroscopy. The NMR analysis showed that ROMT-9 transferred the methyl group specifically to the 3′-hydroxyl group of quercetin, resulting in the formation of its methoxy derivative. Furthermore, ROMT-9 converted flavonoids containing the 3′-hydroxy functional group such as eriodictyol, luteolin, quercetin and taxifolin into the corresponding methoxy derivatives, suggesting that ROMT-9 is an OMT with strict specificity for the 3′-hydroxy group of flavonoids.
Discovery of lesser known flavones as inhibitors of NF-κB signaling in MDA-MB-231 breast cancer cells - A SAR study
Amrutha,Nanjan, Pandurangan,Shaji, Sanu K.,Sunilkumar, Damu,Subhalakshmi,Rajakrishna, Lakshmi,Banerji, Asoke
, p. 4735 - 4742 (2014)
Seventeen flavonoids with different substitutions were evaluated for inhibition of nuclear factor-κB (NF-κB) signaling in the invasive breast cancer cell line MDA-MB-231. They were screened using an engineered MDA-MB-231 cell line reporting NF-κB activation. The modulation of expression of two NF-κB regulated genes involved in tumorigenesis, matrix metalloproteinase-9 (MMP-9), and cyclooxygenase-2 (COX-2) were also analyzed in these cells. Among the compounds tested, all except gossypetin and quercetagetin inhibited the activation of NF-κB, and the expression of MMP-9 and COX-2 to different degree. Methylated flavone, chrysoeriol (luteolin-3′-methylether), was found to be the most potent inhibitor of MMP-9 and COX-2 expressions. The effect of chrysoeriol on cell proliferation, cell cycle, apoptosis and metastasis was analyzed by established methods. Chrysoeriol caused cell cycle arrest at G2/M and inhibited migration and invasion of MDA-MB-231 cells. The structure-activity relations amongst the flavonoids as NF-κB signaling inhibitors was studied. The study indicates differences between the actions of various flavonoids on NF-κB activation and on the biological activities of breast cancer cells. Flavones in general, were more active than the corresponding flavonols.
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Tatsuta
, p. 327 (1941)
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Biological Properties and Absolute Configuration of Flavanones From Calceolaria thyrsiflora Graham
Cabezas, Francisco,Cortez-San Martín, Marcelo,Díaz, Katy,González, César,Joseph-Nathan, Pedro,Mascayano, Carolina,Mejias, Sophia,Montoya, Margarita,Mu?oz, Marcelo A.,Osorio, Mauricio,Taborga, Lautaro,Torrent, Claudia,Vásquez-Martínez, Yesseny,Valdés, Ernesto
, (2020/08/19)
Flavanones (–)-(2S)-5,4’-dihydroxy-7-methoxyflavanone (1) and (–)-(2S)-5,3’,4’-trihydroxy-7-methoxyflavanone (2) were isolated from the extracts of Calceolaria thyrsiflora Graham, an endemic perennial small shrub growing in the central zone of Chile. The absolute configuration of these compounds was resolved by optical rotation experiments and in silico calculations. Three analogs (3, 4, and 5) were synthesized to do structure-activity relationships with the biological assays studied. Biological tests revealed that only flavanone 2 exhibited a moderate inhibitory activity against the methicillin-resistant strain S. aureus MRSA 97-77 (MIC value of 50 μg/ml). In addition, flavanone 2 showed a potent, selective, and competitive inhibition of 5-hLOX, which supports the traditional use of this plant as an anti-inflammatory in diseases of the respiratory tract. Also, 2 exhibited cytotoxic and selective effects against B16-F10 (8.07 ± 1.61 μM) but 4.6- and 17-fold lesser activity than etoposide and taxol.
Influence of Substrate Binding Residues on the Substrate Scope and Regioselectivity of a Plant O-Methyltransferase against Flavonoids
Tang, Qingyun,Vianney, Yoanes M.,Weisz, Klaus,Grathwol, Christoph W.,Link, Andreas,Bornscheuer, Uwe T.,Pavlidis, Ioannis V.
, p. 3721 - 3727 (2020/06/02)
Methylation of free hydroxyl groups is an important modification for flavonoids. It not only greatly increases absorption and oral bioavailability of flavonoids, but also brings new biological activities. Flavonoid methylation is usually achieved by a specific group of plant O-methyltransferases (OMTs) which typically exhibit high substrate specificity. Here we investigated the effect of several residues in the binding pocket of the Clarkia breweri isoeugenol OMT on the substrate scope and regioselectivity against flavonoids. The mutation T133M, identified as reported in our previous publication, increased the activity of the enzyme against several flavonoids, namely eriodictyol, naringenin, luteolin, quercetin and even the isoflavonoid genistein, while a reduced set of amino acids at positions 322 and 326 affected both, the activity and the regioselectivity of the methyltranferase. On the basis of this work, methylated flavonoids that are rare in nature were produced in high purity.