117-39-5 Usage
Uses
1. Used in Medicine:
Quercetin is used as an antioxidant that reverses the immunosuppressive effects of high glucose and hyperglycemic sera in type 2 diabetic patients. It also has good expectorant, anti-cough, and anti-asthma effects, making it useful for treating chronic bronchitis and as an adjuvant therapy for coronary heart disease and high blood pressure.
2. Used in Apis mellifera (Beekeeping):
Quercetin serves as a detoxifying phytochemical in Apis mellifera, contributing to the health and well-being of honeybees.
3. Used in DPPH Radical Scavenging Assay:
It is used as a positive control in the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging assay, which measures the antioxidant capacity of various substances.
4. Used in Analytical Standards:
Quercetin is utilized as an analytical standard for determining the total flavonoid content in various samples.
5. Used in the Food Industry:
It acts as an antioxidant, primarily for oil, drinks, cold drinks, and meat processing products, improving their shelf life and preventing oxidation.
6. Used in the Chemical Industry:
Quercetin is reported to form epoxy resins when mixed with epichlorohydrin, which can be used in various industrial applications.
Physical Properties:
Quercetin appears as a yellow needle-like crystalline powder or yellow powder. It is slightly soluble in water, soluble in ethanol, acetone, pyridine, and acetic acid, and easily soluble in ether and methanol. It has a melting point of 314–317 °C and converts to an anhydrous form at 203-207°F. Alcoholic solutions of quercetin taste very bitter.
Chemical Properties:
Quercetin has good thermal stability with a decomposition temperature of 314 °C. It can improve the light-tolerance property of food pigments, preventing changes in the flavor of food. Its color changes in the presence of metal ions. Quercetin and its derivatives are flavonoid compounds with anti-free radical, anti-oxidation, anti-bacterial, anti-viral, and anti-allergic effects. It also has a diuretic effect and can be used as a metal chelate or a receptor for free groups produced during the oxidation process of grease, making it a suitable antioxidant for ascorbic acid or grease.
Expectorants
Quercetin is commonly used as a expectorant drug in clinical medicine in China. This product has various kinds of pharmacological functions such as having a good expectorant, cough effect, also having certain anti-asthma effect, and having further effects of lowering blood pressure, enhancing capillary resistance, reducing capillary fragility, reducing blood fat, expansion of coronary artery, increasing coronary blood flow.
Clinically, quercetin is mainly used for treating clinical bronchitis and phlegmatic inflammation. It also has adjuvant therapy effect on coronary artery disease and high blood pressure. FDA may have some kinds of adverse reactions such as dry mouth, dizziness, and burning sensation in stomach area which may disappear after treatment.
Quercetin is widely distributed in angiosperms such as Threevein Astere, Golden Saxifrage, berchemia lineata, gold, rhododendron dauricum, seguin loquat, purple rhododendron, Rhododendron micranthum, Japanese Ardisia Herb and Apocynum. It is a kind of aglycon which mainly combines with carbohydrate to be in the form of glycosides, such as quercetin, rutin, hyperoside.
Pharmacological effects
Quercetin can significantly inhibit the effect of cancer-promoting agent, inhibiting the growth of malignant cells in vitro, inhibiting the DNA, RNA, and protein synthesis of Ehrlich ascites tumor cells.
Quercetin has effects of inhibiting the platelet aggregation and the release effect of serotonin (5-HT) as well as inhibiting the platelet aggregation process which is induced by ADP, thrombin and platelet-activating factor (PAF) in which having the strongest inhibition effect on PAF. Moreover, it can also inhibit thrombin-induced the release of platelet 3H-5-HT of rabbit.
(1) Intravenously adding 0.5mmol/L quercetin (10ml/kg) drop wise can significantly shorten the duration of arrhythmia in mice of myocardial ischemia and reperfusion, reduce the incidence of ventricular fibrillation, and reduce the content of MDA as well as the activity of xanthine oxidase inside the ischemic myocardial tissue while having significantly protective effect on SOD. This may be related to the inhibition of the formation process of myocardial oxygen free radical and protection of SOD or directly scavenging of radical free oxygen in myocardial tissue.
(2) Having in vitro assay with quercetin and rutin being together can disperse the platelet and thrombus adhered to the rabbit aorta endothelium with an EC50 of 80 and 500nmol/L, respectivly. In vitro assay of a concentration of quercetin at 50~500μmol/L has shown that it can improve cAMP level inside human platelet, enhance the PGI2-induced improvement of cAMP level of human platelet and inhibit the ADP-induced platelet aggregation. Quercetin at a concentration ranged from 2~50μmol/L has a concentration-dependent enhancement effect. Quercetin, at a concentration of 300 μmol/L in vitro can not only almost completely inhibit the process of platelet aggregation induced by platelet-activating factor (PAF), but also inhibit thrombin and ADP-induced platelet aggregation as well as inhibit the release of rabbit platelet 3H-5HT induced by thrombin; A concentration of 30 μmol/L can significantly reduce the liquidity of platelet membrane.
(3) Quercetin, at a concentration at 4×10-5~1×10-1g/ml, has a inhibitory effect on the release of histamine and SRS-A in the lung of ovalbumin-sensitized guinea pig lung; A concentration of 1 × 10-5g/ml also has inhibitory effect on the for SRS-A induced ileum contraction of guinea pig. Quercetin, at a concentration of 5~50μmol/L, has a concentration-dependent inhibitory effect on the process of histamine release of human basophilic leucocyte. Its inhibitory effect on the ileum contraction of ovalbumin sensitized guinea pig is also concentration-dependent with an IC50 of 10μmol/L. A concentration in the range of 5×10-6~5×10-5mol L can inhibit the proliferation of cytotoxic T lymphocyte (CTL) as well as inhibit ConA-induced DNA synthesis.
The above information is edited by the lookchem of Dai Xiongfeng.
Production method
1. Crash the bark of trees in Fagaceae Quercus (Quercus) into powder, wash with hot brine, extract with dilute ammonia before neutralization with dilute sulfuric acid. Boil the filtrate and separate crystals.
2. It can be obtained by extracting Liliaceae onion (Alliumcepa) with 95% ethanol; it can also be produced from rutin (rutin) extract, quercetin, isoquercitrin, fennel glycosides, hyperoside, quercimeritrin, bloom glycosides through rutin degrading enzyme or hydrolysis with acidic aqueous solution.
History
In 1936, Szent-Gyorgyi firstly reported the separation and identification of biological
activity of quercetin. Usually quercetin is presented in the form of glycosides
such as lutin, quercitrin, and mycoside, which can be hydrolyzed to get the quercetin.
Quercetin has a polyphenol hydroxyl structure, which is of weak lipophilicity and poor hydrophilicity, resulting in its low bioavailability and limiting its clinical application. The synthesis of phenolic derivatives improves its bioavailability,
which are lipid-soluble quercetin derivatives such as 3-O-methylquercetin, hydrophilic
quercetin derivatives such as 3′-ON-carboxymethylformamide quercetin, and quercetin glycosides. Threevein Aster, having quercetin as one of the main active ingredients, has been used for the domestic clinical treatment for chronic bronchitis in China since 1971.
Indications
It is mainly used for the treatment of chronic bronchitis.
Air & Water Reactions
Sensitive to exposure to air and light. Insoluble in water.
Reactivity Profile
3,3',4',5,7-Pentahydroxyflavone is a strong antioxidant and a metal chelator. Promotes the formation of nitrosamines .
Hazard
Questionable carcinogen.
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition 3,3',4',5,7-Pentahydroxyflavone emits acrid smoke and irritating fumes.
Fire Hazard
Flash point data for 3,3',4',5,7-Pentahydroxyflavone are not available; however, 3,3',4',5,7-Pentahydroxyflavone is probably combustible.
Biological Activity
Anti-tumor agent; induces apoptosis and inhibits synthesis of heat shock proteins. Inhibits many enzyme systems including tyrosine protein kinase, phospholipase A 2 , phosphodiesterases, mitochondrial ATPase, PI 3-kinase and protein kinase C. Can also activate Ca 2+ and K + channels and behaves as an agonist at estrogen (GPR30) receptors.
Biochem/physiol Actions
Quercetin is a flavonoid with anticancer activity. Quercetin is a mitochondrial ATPase and phosphodiesterase inhibitor. It Inhibits PI3-kinase activity and slightly inhibits PIP kinase activity. Quercetin has antiproliferative effects on cancer cell lines, reduces cancer cell growth via type II estrogen receptors, and arrests human leukemic T cells in late G1 phase of the cell cycle. Quercetin may also inhibit fatty acid synthase activity.
Pharmacology
Experimental studies showed that quercetin had antitumor, anti-inflammatory, anti-oxidation, hypoglycemic, anti-obesity, antidepressant, and other effects. In vitro cell experiments and in vivo animal experiments have shown that quercetin could
inhibit the growth of various malignant tumor cells such as human ovarian cancer,
breast cancer, gastrointestinal tumor cells, and leukemia, and it could induce cancer
cell apoptosis and had a reversal of tumor multidrug resistance (MDR) effect, while,
combined with other anticancer drugs, it could enhance the effect of anticancer
drugs. Quercetin could alleviate the inflammatory response that was aggravated by the activation of the central granulocytes. In the experimental study on the treatment of non-bacterial prostatitis and acute gouty arthritis, quercetin also showed a good
anti-inflammatory effect. The experimental results showed that quercetin had a good direct scavenging effect on free radicals and exhibited antioxidant activity. In addition, it also had the anti-hepatic fibrosis, pulmonary fibrosis, keloid hyperplasia and glaucoma filtering bubble scarring and other effects, its mechanism involving the inhibition of fibroblast proliferation, inhibition of collagen synthesis, preventing oxidative damage and so on. Moreover, studies have shown that quercetin also had antibacterial, antiaging, antidepressant, antileukemia, antidiabetic, and other pharmacological effects.
Clinical Use
Since the first clinical phase I trial of quercetin in 1996 found that it had antitumor
activity, quercetin has also been reported in early clinical trials of cardiovascular
disease, diabetes, and other diseases. However, there is still insufficient evidence shown that quercetin has a significant effect on the treatment of the disease in clinic.The US FDA has issued a warning, emphasizing that quercetin is not a definite
nutrient, unable to determine its content in the diet, nor can it be used as a drug. China’s Threevein Aster consists of a single Chinese herb, which was released by
the Pharmacopoeia of the People’s Republic of China (1977) Part I. One of the main active ingredients obtained following the hydrolysis of Threevein Aster is quercetin, which has the function of relieving cough and eliminating phlegm and can be used for the treatment of chronic bronchitis. The anti-inflammatory effect of Threevein Aster is poor. Side effects after use include stomach discomfort, dizziness, and abdominal pain, while withdrawal can make them disappear.
Safety Profile
Poison by ingestion, subcutaneous, and intravenous routes. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Human mutation data reported. Used as a pharmaceutical and veterinary drug. When heated to decomposition it emits acrid smoke and irritating fumes
in vivo
studies showed that administration of quercetin before the initiation stage of carcinogenesis dramatically reduced various chemical agents induced tumor burden in mice models, including benzo(a)pyrene-induced lung tumor burden, azoxymethane-induced preneoplastic lesions in rat colon and n-nitrosodiethylamine-induced hepatocarcinoma etc. [5].
references
quercetin and cancer chemoprevention. evid based complement alternat med. 2011;2011:591356. doi: 10.1093/ecam/neq053. epub 2011 apr 14.food-derived polyphenols inhibit pancreatic cancer growth through mitochondrial cytochrome c release and apoptosis. int j cancer. 2002 apr 10;98(5):761-9.stabilization of p53 is involved in quercetin-induced cell cycle arrest and apoptosis in hepg2 cells. bioscience, biotechnology and biochemistry. 2008;72(3):797–804.survivin and p53 modulate quercetin-induced cell growth inhibition and apoptosis in human lung carcinoma cells. the journal of biological chemistry. 2004the effects of quercetin on antioxidant status and tumor markers in the lung and serum of mice treated with benzo(a)pyrene. biological and pharmaceutical bulletin. 2007
Check Digit Verification of cas no
The CAS Registry Mumber 117-39-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 7 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 117-39:
(5*1)+(4*1)+(3*7)+(2*3)+(1*9)=45
45 % 10 = 5
So 117-39-5 is a valid CAS Registry Number.
117-39-5Relevant articles and documents
Two new acetylated flavonoid glycosides from Phyllanthus urinaria
Wu, Chun,Wei, Chun-Shan,Yu, Shao-Fu,Liu, Bai-Lian,Li, Yao-Lan,Ye, Wen-Cai,Tong, Guang-Dong,Zhou, Guang-Xiong
, p. 703 - 707 (2013)
Two new acetylated flavonoid glycosides, quercetin 3-O-α-l-(2,4-di-O- acetyl) rhamnopyranoside-7-O-α-l-rhamnopyranoside (1) and quercetin 3-O-α-l-(3,4-di-O-acetyl) rhamnopyranoside-7-O-α-l-rhamnopyranoside (2), together with two known compounds, quercetin
FLAVONOID GLYCOSIDES AND AN ANTHRAQUINONE FROM RUMEX CHALEPENSIS
Hasan, Aurangzeb,Ahmed, Iftikar,Jay, Maurice,Voirin, Bernard
, p. 1211 - 1214 (1995)
Besides rutin, quercetin 3-rhamnoside and kaempferol 3-rhamnosyl (1-4)galactoside, and 1,6,8-trihydroxy-1-methyl anthraquinone (emodine) have been characterized from leaves of Rumex chalepensis.The structures were established on the basis of Rf values, acid hydrolysis to aglycone and sugar and UV, EI and FAB-mass-spectra, 1H NMR, 12C DEPT NMR, NOE difference measurements, 1H-H-COSY and 1H-13C COSY spectral data.
Mechanistically elucidating the in vitro safety and efficacy of a novel doxorubicin derivative
Alrushaid, Samaa,Zhao, Yunqi,Sayre, Casey L.,Maayah, Zaid H.,Laird Forrest,Senadheera, Sanjeewa N.,Chaboyer, Kevin,Anderson, Hope D.,El-Kadi, Ayman O. S.,Davies, Neal M.
, p. 582 - 597 (2017)
Doxorubicin is an effective anticancer drug; however, it is cardiotoxic and has poor oral bioavazilability. Quercetin is a plant-based flavonoid with inhibitory effects on P-glycoprotein (P-gp) and CYP3A4 and also antioxidant properties. To mitigate these therapeutic barriers, DoxQ, a novel derivative of doxorubicin, was synthesized by conjugating quercetin to doxorubicin. The purpose of this study is to mechanistically elucidate the in vitro safety and efficacy of DoxQ. Drug release in vitro and cellular uptake by multidrug-resistant canine kidney (MDCK-MDR) cells were quantified by HPLC. Antioxidant activity, CYP3A4 inhibition, and P-gp inhibitory effects were examined using commercial assay kits. Drug potency was assessed utilizing triple-negative murine breast cancer cells, and cardiotoxicity was assessed utilizing adult rat and human cardiomyocytes (RL-14). Levels of reactive oxygen species and gene expression of cardiotoxicity markers, oxidative stress markers, and CYP1B1 were determined in RL-14. DoxQ was less cytotoxic to both rat and human cardiomyocytes and retained anticancer activity. Levels of ROS and markers of oxidative stress demonstrate lower oxidative damage induced by DoxQ compared to doxorubicin. DoxQ also inhibited the expression and catalytic activity of CYP1B1. Additionally, DoxQ inhibited CYP3A4 and demonstrated higher cellular uptake by MDCK-MDR cells than doxorubicin. DoxQ provides a novel therapeutic approach to mitigate the cardiotoxicity and poor oral bioavailability of doxorubicin. The cardioprotective mechanism of DoxQ likely involves scavenging ROS and CYP1B1 inhibition, while the mechanism of improving the poor oral bioavailability of doxorubicin is likely related to inhibiting CYP3A4 and P-gp.
Exploring the oxidation and iron binding profile of a cyclodextrin encapsulated quercetin complex unveiled a controlled complex dissociation through a chemical stimulus
Diamantis, Dimitrios A.,Ramesova, Sarka,Chatzigiannis, Christos M.,Degano, Ilaria,Gerogianni, Paraskevi S.,Karadima, Konstantina E.,Perikleous, Sonia,Rekkas, Dimitrios,Gerothanassis, Ioannis P.,Galaris, Dimitrios,Mavromoustakos, Thomas,Valsami, Georgia,Sokolova, Romana,Tzakos, Andreas G.
, p. 1913 - 1924 (2018)
Background: Flavonoids possess a rich polypharmacological profile and their biological role is linked to their oxidation state protecting DNA from oxidative stress damage. However, their bioavailability is hampered due to their poor aqueous solubility. This can be surpassed through encapsulation to supramolecular carriers as cyclodextrin (CD). A quercetin- 2HP-β-CD complex has been formerly reported by us. However, once the flavonoid is in its 2HP-β-CD encapsulated state its oxidation potential, its decomplexation mechanism, its potential to protect DNA damage from oxidative stress remained elusive. To unveil this, an array of biophysical techniques was used. Methods: The quercetin-2HP-β-CD complex was evaluated through solubility and dissolution experiments, electrochemical and spectroelectrochemical studies (Cyclic Voltammetry), UV–Vis spectroscopy, HPLC-ESI-MS/MS and HPLC-DAD, fluorescence spectroscopy, NMR Spectroscopy, theoretical calculations (density functional theory (DFT)) and biological evaluation of the protection offered against H2O2-induced DNA damage. Results: Encapsulation of quercetin inside the supramolecule's cavity enhanced its solubility and retained its oxidation profile. Although the protective ability of the quercetin-2HP-β-CD complex against H2O2 was diminished, iron serves as a chemical stimulus to dissociate the complex and release quercetin. Conclusions: We found that in a quercetin-2HP-β-CD inclusion complex quercetin retains its oxidation profile similarly to its native state, while iron can operate as a chemical stimulus to release quercetin from its host cavity. General significance: The oxidation profile of a natural product once it is encapsulated in a supramolecular carrier was unveiled as also it was discovered that decomplexation can be triggered by a chemical stimilus.
Elucidation of active site residues of Arabidopsis thaliana flavonol synthase provides a molecular platform for engineering flavonols
Chua, Chun Song,Biermann, Daniela,Goo, Kian Sim,Sim, Tiow-Suan
, p. 66 - 75 (2008)
Arabidopsis thaliana flavonol synthase (aFLS) catalyzes the production of quercetin, which is known to possess multiple medicinal properties. aFLS is classified as a 2-oxoglutarate dependent dioxygenase as it requires ferrous iron and 2-oxoglutarate for catalysis. In this study, the putative residues for binding ferrous iron (H221, D223 and H277), 2-oxoglutarate (R287 and S289) and dihydroquercetin (H132, F134, K202, F293 and E295) were identified via computational analyses. To verify the proposed roles of the identified residues, 15 aFLS mutants were constructed and their activities were examined via a spectroscopic assay designed in this study. Mutations at H221, D223, H277 and R287 completely abolished enzymes activities, supporting their importance in binding ferrous iron and 2-oxoglutarate. However, mutations at the proposed substrate binding residues affected the enzyme catalysis differently such that the activities of K202 and F293 mutants drastically decreased to approximately 10% of the wild-type whereas the H132F mutant exhibited approximately 20% higher activity than the wild-type. Kinetic analyses established an improved substrate binding affinity in H132F mutant (Km: 0.027 ± 0.0028 mM) compared to wild-type (Km: 0.059 ± 0.0063 mM). These observations support the notion that aFLS can be selectively mutated to improve the catalytic activity of the enzyme for quercetin production.
Structural determination and DPPH radical-scavenging activity of two acylated flavonoid tetraglycosides in oolong tea (Camellia sinensis)
Lee, Viola Szu-Yuan,Chen, Chiy-Rong,Liao, Yun-Wen,Tzen, Jason Tze-Cheng,Chang, Chi-I.
, p. 851 - 853 (2008)
Two major acylated flavonoid tetraglycosides were isolated from the methanol extract of oolong tea. Their structures were elucidated by spectroscopic methods as quercetin 3-O-[2G-(E)-coumaroyl-3 G-O-β-D-glucosyl-3R-O-β-D-g
Transrutinosylation of tyrosol by flower buds of Sophora japonica
Karni?ová Potocká, Elena,Mastihuba, Vladimír,Mastihubová, Mária
, (2021)
Dried flower buds of Japanese sophora (Sophora japonica) comprising rutinosidase activity were tested in rutinosylation of tyrosol via transglycosylation process from rutin. Optimal conditions for transrutinosylation of tyrosol were 49 mM rutin and 290 mM
One-pot preparation of quercetin using natural deep eutectic solvents
Zang, Yuan-Yuan,Yang, Xi,Chen, Zhi-Gang,Wu, Tao
, p. 193 - 198 (2020)
In this study, we have established a green and efficient preparation method of quercetin. Rutin was first extracted from Sophora japonica using natural deep eutectic solvents (NADESs), then hydrolyzed into quercetin by rutin degrading enzyme (RDE) obtained from germinated tartary buckwheat in situ. Rutin solubility tests showed that most of the 11 NADESs increased the solubility of rutin by 67-3116 times compared to water. Thus, NADESs could be prior candidate to extract rutin. Extraction efficiency of rutin varied with different NADESs, and a maximum of 291.57 mg g?1 was achieved in NADES ChGly, which was prepared by mixing choline chloride and glycerol at a molar ratio of 1:1. After that hydrolysis was performed directly in extraction system by adding RDE with degradation rate of up to 8.36 mg min-1·L-1. Our findings suggest that preparation of quercetin using NADESs was simple and feasible to operate, environmentally friendly, efficient, and inspired the preparation method of bioactive components from a new perspective.
Optimization of the biosynthesis of b-ring ortho-hydroxy lated flavonoids using the 4-hydroxyphenylacetate 3-hydroxylase complex (Hpabc) of escherichia coli
Chen, Yang,Gao, Liping,Gui, Lin,Guo, Lina,Lei, Ting,Li, Yan,Ma, Xiubing,Ruan, Haixiang,Wang, Longji,Wang, Yunsheng,Xia, Tao
, (2021)
Flavonoids are important plant metabolites that exhibit a wide range of physiological and pharmaceutical functions. Because of their wide biological activities, such as anti-inflammatory, antioxidant, antiaging and anticancer, they have been widely used in foods, nutraceutical and pharmaceuticals industries. Here, the hydroxylase complex HpaBC was selected for the efficient in vivo production of ortho-hydroxylated flavonoids. Several HpaBC expression vectors were constructed, and the corresponding products were successfully detected by feeding naringenin to vector-carrying strains. However, when HpaC was linked with an S-Tag on the C terminus, the enzyme activity was significantly affected. The optimal culture conditions were determined, including a substrate concentration of 80 mg·L?1, an induction temperature of 28?C, an M9 medium, and a substrate delay time of 6 h after IPTG induction. Finally, the efficiency of eriodictyol conversion from P2&3-carrying strains fed naringin was up to 57.67 ± 3.36%. The same strategy was used to produce catechin and caf-feic acid, and the highest conversion efficiencies were 35.2 ± 3.14 and 32.93 ± 2.01%, respectively. In this paper, the catalytic activity of HpaBC on dihydrokaempferol and kaempferol was demonstrated for the first time. This study demonstrates a feasible method for efficiently synthesizing in vivo B-ring dihydroxylated flavonoids, such as catechins, flavanols, dihydroflavonols and flavonols, in a bacterial expression system.
Phenolic compounds from Carthamus tinctorius
Suleimanov
, p. 13 - 15 (2004)
The contents of quercetin, luteolin, apigenin, isorhamnetin, umbelliferone, and daphnoretin in common safflower and of acacetin in the flowers were determined based on the physical and chemical properties of the isolated substances.
