74893-81-5Relevant articles and documents
Novel Quercetin Aggregation-Induced Emission Luminogen (AIEgen) with Excited-State Intramolecular Proton Transfer for In Vivo Bioimaging
He, Ting,Niu, Na,Chen, Zhijun,Li, Shujun,Liu, Shouxin,Li, Jian
, (2018)
Aggregation-induced emission luminogens (AIEgens) that undergo excited-state intramolecular proton transfer (ESIPT) have many applications in bioimaging since they have high quantum efficiency in the aggregated state and a low background signal in aqueous solutions because of their large Stokes shift. One disadvantage of many of the AIEgens with ESIPT that has been described so far is that they require time-consuming synthesis and the use of toxic reagents. Another disadvantage with most of these materials is that they are only used for bioimaging in cells and are unsuitable for in vivo bioimaging. Herein, a new AIEgen with ESIPT, quercetin (QC) is described, which is easily prepared from Sophora japonica. AIE is attributed to crystallization-promoted keto emission. The fluorescence is temperature dependent and shows strong resistance to photobleaching. QC AIEgen with ESIPT is shown to have excellent biocompatibility and is successfully used for bioimaging both in cellular cytoplasm and in vivo.
Isolation, characterization, complete structural assignment, and anticancer activities of the methoxylated flavonoids from rhamnus disperma roots
Abd El-Wahab, Mohammed F.,Abdalla, Ashraf N.,Mohammed, Abd El-Salam I.,Mohammed, Hamdoon A.,Ragab, Ehab A.,Shaheen, Usama
, (2021/10/01)
Different chromatographic methods including reversed-phase HPLC led to the isolation and purification of three O-methylated flavonoids; 5,4’-dihydroxy-3,6,7-tri-O-methyl flavone (penduletin) (1), 5,3’-dihydroxy-3,6,7,4’,5’-penta-O-methyl flavone (2), and 5-hydroxy-3,6,7,3’,4’,5’-hexa-O-methyl flavone (3) from Rhamnus disperma roots. Additionlly, four flavonoid glycosides; kampferol 7-O-α-L-rhamnopyranoside (4), isorhamnetin-3-O-β-D-glucopyranoside (5), quercetin 7-O-α-L-rhamnopyranoside (6), and kampferol 3, 7-di-O-α-L-rhamnopyranoside (7) along with benzyl-O-β-D-glucopyranoside (8) were successfully isolated. Complete structure characterization of these compounds was assigned based on NMR spectroscopic data, MS analyses, and comparison with the literature. The O-methyl protons and carbons of the three O-methylated flavonoids (1–3) were unambiguously assigned based on 2D NMR data. The occurrence of compounds 1, 4, 5, and 8 in Rhamnus disperma is was reported here for the first time. Compound 3 was acetylated at 5-OH position to give 5-O-acetyl-3,6,7,3’,4’,5’-hexa-O-methyl flavone (9). Compound 1 exhibited the highest cytotoxic activity against MCF 7, A2780, and HT29 cancer cell lines with IC50 values at 2.17 μM, 0.53 μM, and 2.16 μM, respectively, and was 2–9 folds more selective against tested cancer cell lines compared to the normal human fetal lung fibroblasts (MRC5). It also doubled MCF 7 apoptotic populations and caused G1 cell cycle arrest. The acetylated compound 9 exhibited cytotoxic activity against MCF 7 and HT29 cancer cell lines with IC50 values at 2.19 μM and 3.18 μM, respectively, and was 6–8 folds more cytotoxic to tested cancer cell lines compared to the MRC5 cells.
A natural hyperoside based novel light-up fluorescent probe with AIE and ESIPT characteristics for on-site and long-term imaging of β-galactosidase in living cells
Fu, Qiachi,Guo, Ying,Long, Ruiqing,Shi, Shuyun,Tang, Cui,Tong, Chaoying,Wang, Daijie,Xu, Jinju,Yang, Zan
supporting information, p. 11860 - 11865 (2020/09/16)
Fluorescence-based on-site and long-term sensing and bioimaging of biomarkers are highly desired for effective diagnosis. Aggregation-induced emission luminogens (AIEgens) with excited-state intramolecular proton transfer (ESIPT) characteristics have outstanding advantages in biological applications due to their large Stokes shift and low background signal in the aggregate state. However, most of the reported AIEgens are fabricated through rational design and complex synthesis procedures. Importantly, with rich structural skeletons and ease of access, natural products have superiority in developing promising AIEgens with ESIPT. Here, hyperoside(quercetin-3-O-β-galactoside) has been easily obtained fromHedyotis diffusa. After the incubation of hyperoside with β-galactosidase (β-Gal), the hydrolysis product, hydrophobic quercetin, is aggregatedin situ, which presents AIE and ESIPT characteristics with a large Stokes shift (170 nm). Then, a novel light-up fluorescent probe has been fabricated for the detection of β-Gal with a good linear relationship (0.03-12 U mL?1), high sensitivity (a detection limit of 0.013 U mL?1) and superior selectivity. Meanwhile, excellent biocompatibility, low cytotoxicity, outstanding photostability, and good intracellular retention demonstrate its superiority for on-site and long-term (about 8 h) imaging of β-Gal in SKOV-3 cells. The results demonstrate the application of hyperoside in the sensing and imaging of β-Gal in biological samples, and propose the great possibility of natural products for developing novel AIE-based fluorescence probes.
