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| Isoquercetin, isoquercitrin or isotrifoliin is a flavonoid, a type of chemical compound. It is the 3-O-glucoside of quercetin. Isoquercitrin can be isolated from various plant species including Mangifera indica (mango) and Rheum nobile (the Noble rhubarb). It is also present in the leaves of Annona squamosa, Camellia sinensis (tea). and Vestia foetida |
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Read full article at Wikipedia
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InChI=1S/C21H20O12/c22- 6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1 |
| OVSQVDMCBVZWGM-QSOFNFLRSA-N |
| OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O |
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Vitis vinifera
(NCBI:txid29760)
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See:
MetaboLights Study
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Vitis vinifera
(NCBI:txid29760)
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See:
DOI
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Lepisorus contortus
(NCBI:txid699669)
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Found in
whole plant
(BTO:0001461).
95% EtOH extract of air-dried, powdered whole plant
See:
PubMed
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antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
osteogenesis regulator
Any compound that induces or regulates osteogenesis.
histamine antagonist
Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.
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bone density conservation agent
An agent that inhibits bone resorption and/or favor bone mineralization and bone regeneration. Used to heal bone fractures and to treat bone diseases such as osteopenia and osteoporosis.
histamine antagonist
Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.
antipruritic drug
A drug, usually applied topically, that relieves pruritus (itching).
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
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View more via ChEBI Ontology
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2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl β-D-glucopyranoside
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2-(3,4-Dihidroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one
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KEGG COMPOUND
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2-(3,4-dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one
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ChEBI
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isoquercetin
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ChEBI
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Isoquercitrin
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KEGG COMPOUND
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Isotrifoliin
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KEGG COMPOUND
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100989
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Reaxys Registry Number
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Reaxys
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21637-25-2
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CAS Registry Number
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KEGG COMPOUND
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482-35-9
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CAS Registry Number
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ChemIDplus
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Zhang L, Xu L, Tu ZC, Wang HH, Luo J, Ma TX (2020)
Mechanisms of isoquercitrin attenuates ovalbumin glycation: Investigation by spectroscopy, spectrometry and molecular docking.
Food chemistry 309, 125667 [PubMed:31679851]
[show Abstract]
This research firstly investigated the inhibitory effect of isoquercitrin (ISQ) on Ovalbumin (OVA) glycation. The mechanism was elucidated through the interaction between OVA and ISQ, and changes in glycation sites and degree of each site as deduced by spectroscopy, spectrometry and molecular docking. ISQ significantly inhibited OVA glycation by attenuating the conformational change induced by glycation. It quenched the fluorescence of Trp via static mechanism, and exposed Trp residues to a more hydrophobic surroundings. Formation of OVA-ISQ complex was a endothermic processing driven by hydrophobic interactions, van der Waals forces and hydrogen bonds. LC-Orbitrap-MS/MS revealed that ISQ altered the location of glycation and alleviated the glycation degree of most sites. Molecular docking results indicated that ISQ inserted into the hydrophobic pocket of OVA with six hydrogen bonds and one π-π stacking formed between ISQ and the amino acid residues of OVA, leading to the altered glycation activity of some sites. | Ma TX, Zhang L, Xu L, Ye YH, Huang T, Zhou QM, Liu HL (2020)
Mitigation of isoquercitrin on β-lactoglobulin glycation: Insight into the mechanisms by mass spectrometry and interaction analysis.
International journal of biological macromolecules 155, 1133-1141 [PubMed:31715232]
[show Abstract]
Formation of advanced glycation end products (AGEs) on foods imposes threats to human health after intaking. This research firstly evaluated the inhibition of isoquercitrin on β-lactoglobulin (β-Lg) glycation, the mechanisms were elucidated by fluorescence spectroscopy, Orbitrap MSn and molecular docking. Fluorescence spectra indicated that isoquercitrin effectively alleviated the formation of AGEs, it could stabilize the conformation structure of glycated β-Lg (G-β-Lg), change the micro-environment in the vicinity of chromophores. SDS-PAGE analysis revealed the suppressed cross-linking of G-β-Lg induced by isoquercitrin. The number of glycation site detected on G-β-Lg was reduced from ten to eight after the addition of isoquercitrin, and the relative glycation degree of substitution of per site (RGDSP) of most glycation sites were also greatly decreased. As indicated by intermolecular interaction, isoquercitrin quenched the fluorescence of β-Lg via a static mechanism, and their combination is an endothermic processing mainly derived by hydrophobic interaction, hydrogen bonds, and van der Waals forces. Isoquercitrin interacted with β-Lg to form an equimolar complex, and one hydrogen bond was formed between isoquercitrin and Lys69 (4.96 Å). Above results proved that isoquercitrin can be a promising anti-glycation agent used in food system to prevent the formation of harmful glycation products. | Syed MM, Doshi PJ, Dhavale DD, Doshi JB, Kate SL, Kulkarni G, Sharma N, Uppuladinne M, Sonavane U, Joshi R, Kulkarni MV (2020)
Potential of isoquercitrin as antisickling agent: a multi-spectroscopic, thermophoresis and molecular modeling approach.
Journal of biomolecular structure & dynamics 38, 2717-2736 [PubMed:31315526]
[show Abstract]
Sickle cell disease is an inherited disease caused by point mutation in hemoglobin (β-globin gene). Under oxygen saturation, sickle hemoglobin form polymers, leading to rigid erythrocytes. The transition of the blood vessels is altered and initiated by the adhesion of erythrocytes, neutrophils and endothelial cells. Sickle Hemoglobin (HbS) polymerization is a major cause in red blood cells (RBC), promoting sickling and destruction of RBCs. Isoquercitrin, a medicinal bioactive compound found in various medicinal plants, has multiple health benefits. The present study examines the potential of isoquercitrin as an anti-sickle agent, showing a significant decrease in the rate of polymerization as well as sickling of RBCs. Isoquercitrin-induced graded alteration in absorbance and fluorescence of HbS, confirmed their interaction. A negative value of ΔG° strongly suggests that it is a spontaneous exothermic reaction induced by entropy. Negative ΔH° and positive ΔS° predicted that hydrogen and hydrophobic binding forces interfered with a hydrophobic microenvironment of β6Val leading to polymerization inhibition of HbS. HbS-Isoquercitrin complex exhibits helical structural changes leading to destabilization of the HbS polymer as confirmed by CD spectroscopy. MST and DSC results indicate greater changes in thermophoretic mobility and thermal stability of sickle hemoglobin in the presence of isoquercitrin, respectively. These findings were also supported by molecular simulation studies using DOCK6 and GROMACS. Hence, we can conclude that isoquercitrin interacts with HbS through hydrogen bonding, which leads to polymerization inhibition. Consequently, isoquercitrin could potentially be used as a medication for the treatment of sickle cell disease.Communicated by Ramaswamy H. Sarma. | Jayachandran M, Zhang T, Wu Z, Liu Y, Xu B (2020)
Isoquercetin regulates SREBP-1C via AMPK pathway in skeletal muscle to exert antihyperlipidemic and anti-inflammatory effects in STZ induced diabetic rats.
Molecular biology reports 47, 593-602 [PubMed:31677037]
[show Abstract]
Diabetes mellitus (DM) is a cluster of metabolic diseases that exhibits high blood glucose levels accompanied by hyperlipidemia and inflammation. DM is the primary risk factor contributes majorly to cardiovascular disease (CVD) mediated morbidity and mortality. The incidence of dyslipidemia seems to attribute considerably to the initiation of CVDs. The beneficial action of isoquercetin on hyperlipidemia and related signaling pathways are not documented yet, hence we decide to carry out this study. The experimental rats were divided into five groups: Group 1, control rats; group 2, isoquercetin control (40 mg/kg b.w); group 3, diabetic rats (STZ-40 mg/kg b.w); group 4, diabetic + isoquercetin (40 mg/kg b.w); and group 5, diabetic + glibenclamide (600 µg/kg b.w). The animals were sacrificed at the end of the experimental duration of 45 days. Results of our analysis reveal that isoquercetin have a major impact on the tissue lipid profile, isoquercetin strongly regulates the expression of various lipid-metabolizing enzymes, C-reactive protein, expression of various inflammatory genes, SREBP-1C genes and proteins and AMP-activated protein kinase-α (AMPK) signaling pathway genes and proteins. Results recommend that isoquercetin can be effective in mitigating the consequences of hyperlipidemia and DM. | Li LJ, Liu XQ, Du XP, Wu L, Jiang ZD, Ni H, Li QB, Chen F (2020)
Preparation of isoquercitrin by biotransformation of rutin using α-L-rhamnosidase from Aspergillus niger JMU-TS528 and HSCCC purification.
Preparative biochemistry & biotechnology 50, 1-9 [PubMed:31441715]
[show Abstract]
Isoquercitrin is a flavonoid with important applications in the pharmaceutical and nutraceutical industries. However, a low yield and high production cost hinders the industrial preparation of isoquercitrin. In the present study, isoquercitrin was prepared by biotransformation of rutin using α-L-rhamnosidase from Aspergillus niger JMU-TS528 combined with high-speed countercurrent chromatography (HSCCC) purification. As a result, the optimum transformation pH, temperature, and time were pH 4.0, 60 °C, and 60 min, respectively. The Km and Vmax were 0.36 mM and 0.460 mmol/min, respectively. For isoquercitrin production, the optimal rutin concentration and transformation time were approximately 1000 mg/L and 60 min. The rutin transformation rate reached 96.44%. The isoquercitrin was purified to a purity of 97.83% using one-step purification with HSCCC. The isoquercitrin was identified using UPLC-Q-TOF-MS. The comprehensive results indicated that the biotransformation procedure using the α-L-rhamnosidase from A. niger JMU-TS528 combined with HSCCC was a simple and effective process to prepare isoquercitrin, which might facilitate the production of isoquercitrin for industrial use. | Bondonno NP, Bondonno CP, Ward NC, Woodman RJ, Hodgson JM, Croft KD (2020)
Enzymatically modified isoquercitrin improves endothelial function in volunteers at risk of cardiovascular disease.
The British journal of nutrition 123, 182-189 [PubMed:31870463]
[show Abstract]
A higher intake of food rich in flavonoids such as quercetin can reduce the risk of CVD. Enzymatically modified isoquercitrin (EMIQ®) has a bioavailability 17-fold higher than quercetin aglycone and has shown potential CVD moderating effects in animal studies. The present study aimed to determine whether acute ingestion of EMIQ® improves endothelial function, blood pressure (BP) and cognitive function in human volunteers at risk of CVD. Twenty-five participants (twelve males and thirteen females) with at least one CVD risk factor completed this randomised, controlled, crossover study. In a random order, participants were given EMIQ® (2 mg aglycone equivalent)/kg body weight or placebo alongside a standard breakfast meal. Endothelial function, assessed by flow-mediated dilatation (FMD) of the brachial artery was measured before and 1·5 h after intervention. BP, arterial stiffness, cognitive function, BP during cognitive stress and measures of quercetin metabolites, oxidative stress and markers of nitric oxide (NO) production were assessed post-intervention. After adjustment for pre-treatment measurements and treatment order, EMIQ® treatment resulted in a significantly higher FMD response compared with the placebo (1·80 (95 % CI 0·23, 3·37) %; P = 0·025). Plasma concentrations of quercetin metabolites were significantly higher (P < 0·001) after EMIQ® treatment compared with the placebo. No changes in BP, arterial stiffness, cognitive function or biochemical parameters were observed. In this human intervention study, the acute administration of EMIQ® significantly increased circulating quercetin metabolites and improved endothelial function. Further clinical trials are required to assess whether health benefits are associated with long-term EMIQ® consumption. | Li J, Wang X, Wang Y, Lu C, Zheng D, Zhang J (2019)
Isoquercitrin, a flavonoid glucoside, exerts a positive effect on osteogenesis in vitro and in vivo.
Chemico-biological interactions 297, 85-94 [PubMed:30365939]
[show Abstract]
Isoquercitrin (quercetin-3-O-β-d-glucopyranoside) possess various pharmacological effect as a biologically active compound. The aim of the present study was to investigate its potential effects on the proliferation and osteoblastic differentiation of bone marrow-derived mesenchymal stem cells (BMSCs) in vitro and bone formation in the mid-palatal suture during rapid maxillary expansion (RME) in vivo. Cell proliferation of rat BMSCs was detected by cell-counting kit- 8 (CCK-8) assay. Alkaline phosphatase (ALP) activity assay and alizarin red staining were used to evaluate osteogenic differentiation of BMSCs. Furthermore, the expression levels of osteogenesis-related genes including runt-related transcription factor 2 (Runx2), bone sialoprotein (BSP) and activating transcription factor 6 (ATF6) were measured by real-time RT-PCR. In vivo, thirty-six male 6-week-old Wistar rats with or without suture expansion receive systemic administration of isoquercitrin or saline solution. Micro-CT, HE and Masson staining were used to compare the morphological changes between the groups. Bone morphogenetic protein 2 (BMP2) expression in the suture was detected using immunohistochemical staining. Our results showed that isoquercitrin significantly promoted cell proliferation, ALP activity and mineral deposition in the range from 0.01 to 1 μM. Moreover, the expression levels of Runx2, BSP and ATF6 were also upregulated. The measurement of micro-CT imaging and histological examinations demonstrated that daily oral administration of isoquercitrin (10 mg/kg) increased bone formation compared to the other groups. Furthermore, the expression level of BMP2 was also augmented in the presence of isoquercitrin. Consequently, those findings showed that isoquercitrin exerts stimulatory effects on osteogenesis in vitro and in vivo, suggesting that isoquercitrin could be a potential candidate for preventing relapse following RME within palatal sutures. | Jayachandran M, Wu Z, Ganesan K, Khalid S, Chung SM, Xu B (2019)
Isoquercetin upregulates antioxidant genes, suppresses inflammatory cytokines and regulates AMPK pathway in streptozotocin-induced diabetic rats.
Chemico-biological interactions 303, 62-69 [PubMed:30817903]
[show Abstract]
Lifestyle and genetic factors contribute to the initiation of oxidative stress and inflammation in diabetes mellitus (DM). Oxidative stress and lipid peroxidation worked in an orchestrated manner and reported to be strongly associated with the formation of the hyperlipidemic condition in DM patients. Isoquercetin, a bioactive constituent isolated from guava leaves has attracted considerable attention because of its antidiabetic activity. The antidiabetic activity of guava leaves may be due to the presence of isoquercetin at a significant level. However, how isoquercetin regulates different pathways in DM is insufficiently studied. We have selected versatile regulators of oxidative stress and inflammatory pathways to fully analyze if isoquercetin effectively modulated the genes of these pathways. At the end of our experimental duration, rats were dissected and analyzed for the oxidative stress, lipid peroxidation, inflammatory and lipid markers. The nuclear factor erythroid 2-related factor 2 (Nrf2) pathway is believed to be the key regulator of expression of various antioxidant enzyme genes and it is directly or indirectly related to nuclear factor Kappa- B (NF-kB) and AMP-activated protein kinase (AMPK) pathways. Therefore, we tend to study the effects of STZ on Nrf2, NF-kB and AMPK pathway and how the isoquercetin treatment performs at a molecular level to overcome the burden of DM. The results of our study provided convincing evidence of significant pharmacological properties of isoquercetin in context of its ability to inhibit the oxidative stress elicited by the STZ through generation of the free radicals and regulation of the expression of Nrf2 pathway-associated proteins and genes and it also reduced the burden of hyperlipidemia and inflammation. By taking the above results into consideration isoquercetin can be studied further to elucidate its antidiabetic effects at various levels. | Li M, Zhang C, Li X, Lv Z, Chen Y, Zhao J (2019)
Isoquercitrin promotes the osteogenic differentiation of osteoblasts and BMSCs via the RUNX2 or BMP pathway.
Connective tissue research 60, 189-199 [PubMed:29852784]
[show Abstract]
AimIsoquercitrin is widely present in fruits, vegetables and medicinal herbs. As a natural phytoestrogen, isoquercitrin has been considered a possible osteoporosis prevention option to avoid the risk of hormone therapy.Materials and methodsThe cell proliferation of osteoblasts and bone mesenchymal stem cells (BMSCs) was examined by cell counting kit-8 (CCK-8). The osteogenic differentiation was evaluated by real-time qPCR, ALP staining and Alizarin Red S staining. Small interfering RNA (siRNA) was used to knockdown the expression of runt-related transcription factor 2 (RUNX2).ResultsThe cell proliferation of osteoblasts and BMSCs was promoted by isoquercitrin at low concentrations. High concentrations of isoquercitrin promoted the osteogenic differentiation via RUNX2 expression in osteoblasts and via the bone morphogenetic protein (BMP) pathway in BMSCs. Inhibition of RUNX2 expression in osteoblasts by siRNA or addition of noggin to the culture medium of BMSCs reduced the effects of osteogenic differentiation induced by isoquercitrin.ConclusionsThese data suggest that isoquercitrin is a natural potential osteoinductive compound and might be valuable for the prevention/treatment of bone disorders. | Fayed HA, Barakat BM, Elshaer SS, Abdel-Naim AB, Menze ET (2019)
Antiosteoporotic activities of isoquercitrin in ovariectomized rats: Role of inhibiting hypoxia inducible factor-1 alpha.
European journal of pharmacology 865, 172785 [PubMed:31712059]
[show Abstract]
Postmenopausal osteoporosis is a common and disabling disorder that increases the risk of bone fractures due to estrogen deprivation; this can be simulated in rats by ovariectomy. Hypoxia inducible factor-1 alpha (HIF-1α) expression in osteoclasts predominantly leads to its activation increasing bone resorption. Premenopausal, estrogen prevents HIF-1α expression maintaining bone density. Unfortunately postmenopausal estrogen replacement therapy is not recommended due to its potential tumor development risk. Isoquercitrin, a common edible plants phytoestrogen, is known to inhibit HIF-1α. This study was conducted to investigate the potential antiosteoporotic activity of isoquercitrin (15, 30 and 60 mg/kg/day) in ovariectomized rats with reference to 17β-estradiol (25 mcg/kg/day). Animals were bilaterally ovariectomized to induce osteoporosis and one month later they were assigned into groups and administered isoquercitrin and 17β-estradiol for 8 weeks. Ovariectomy reduced lumbar compression strength, distorted bone microscopic architecture, inducing cartilage and trabecular dystrophy, and increased the markers of bone turnover (serum alkaline phosphatase and osteocalcin and urinary calcium, phosphorus and creatinine). It also increased the gene expression of HIF-1α and the levels of nuclear factor-kappa B (NF-κB) and decreased the expression of vascular endothelial growth factor (VEGF) and β-catenin in the femurs. Isoquercitrin was found to improve bone histological features, increase lumbar strength and improve most of the biochemical markers of bone turnover in a manner comparable to 17β-estradiol. Isoquercitrin also attenuated the increased HIF-1α expression while increased that of the VEGF and β-catenin. It also decreased the levels of NF-κB. Therefore isoquercitrin may be considered a safer alternative for managing osteoporosis. | Kim JH, Lee S, Cho EJ (2019)
Acer okamotoanum and isoquercitrin improve cognitive function via attenuation of oxidative stress in high fat diet- and amyloid beta-induced mice.
Food & function 10, 6803-6814 [PubMed:31577306]
[show Abstract]
Obesity induced by high-fat diet (HFD) and accumulation of amyloid beta (Aβ) are known as a risk factor of Alzheimer's disease. We previously identified isoquercitrin (IQ) as an active compound of Acer okamotoanum. In the present study, we investigated the protective effects of the active ethyl acetate (EtOAc) fraction from A. okamotoanum and IQ on HFD and Aβ25-35-induced cognitive impairment mice. C57BL/6J mice were fed with HFD for 10 weeks and then Aβ25-35 was injected intracerebroventricularly (i.c.v.). The EtOAc fraction of A. okamotoanum and IQ were administered orally for 4 weeks at 100 and 10 mg kg-1 day-1, respectively. Learning and memory functions were evaluated using behavioral tests including T-maze, object recognition and Morris water maze tests. The HFD and Aβ25-35 injection significantly impaired cognitive and memory function. However, administration of A. okamotoanum and IQ improved spatial cognitive ability and object recognition ability in T-maze and novel object recognition tests. In addition, A. okamotoanum and IQ-administered groups showed enhanced learning and memory function compared with HFD and Aβ25-35-induced cognitive impairment mice in the Morris water maze test. Furthermore, administration of A. okamotoanum and IQ attenuated oxidative stress in the brain via inhibition of reactive oxygen species production, lipid peroxidation, and nitric oxide formation. Therefore, we suggest that A. okamotoanum and IQ improve HFD- and Aβ25-35-induced cognitive impairment by inhibition of oxidative stress, and A. okamotoanum and IQ might be potential candidates for prevention and treatment of obesity- and Aβ-induced cognitive impairment. | Zwicker JI, Schlechter BL, Stopa JD, Liebman HA, Aggarwal A, Puligandla M, Caughey T, Bauer KA, Kuemmerle N, Wong E, Wun T, McLaughlin M, Hidalgo M, Neuberg D, Furie B, Flaumenhaft R, CATIQ Investigators11 (2019)
Targeting protein disulfide isomerase with the flavonoid isoquercetin to improve hypercoagulability in advanced cancer.
JCI insight 4, 125851 [PubMed:30652973]
[show Abstract]
BackgroundProtein disulfide isomerase (PDI) is a thiol isomerase secreted by vascular cells that is required for thrombus formation. Quercetin flavonoids inhibit PDI activity and block platelet accumulation and fibrin generation at the site of a vascular injury in mouse models, but the clinical effect of targeting extracellular PDI in humans has not been studied.MethodsWe conducted a multicenter phase II trial of sequential dosing cohorts to evaluate the efficacy of targeting PDI with isoquercetin to reduce hypercoagulability in cancer patients at high risk for thrombosis. Patients received isoquercetin at 500 mg (cohort A, n = 28) or 1000 mg (cohort B, n = 29) daily for 56 days, with laboratory assays performed at baseline and the end of the study, along with bilateral lower extremity compression ultrasound. The primary efficacy endpoint was a reduction in D-dimer, and the primary clinical endpoint included pulmonary embolism or proximal deep vein thrombosis.ResultsThe administration of 1000 mg isoquercetin decreased D-dimer plasma concentrations by a median of -21.9% (P = 0.0002). There were no primary VTE events or major hemorrhages observed in either cohort. Isoquercetin increased PDI inhibitory activity in plasma (37.0% in cohort A, n = 25, P < 0.001; 73.3% in cohort B, n = 22, P < 0.001, respectively). Corroborating the antithrombotic efficacy, we also observed a significant decrease in platelet-dependent thrombin generation (cohort A median decrease -31.1%, P = 0.007; cohort B median decrease -57.2%, P = 0.004) and circulating soluble P selectin at the 1000 mg isoquercetin dose (median decrease -57.9%, P < 0.0001).ConclusionsIsoquercetin targets extracellular PDI and improves markers of coagulation in advanced cancer patients.Trial registrationClinicaltrials.gov NCT02195232.FundingQuercegen Pharmaceuticals; National Heart, Lung, and Blood Institute (NHLBI; U54HL112302, R35HL135775, and T32HL007917); and NHLBI Consortium Linking Oncology and Thrombosis (U01HL143365). | Michalcova K, Roychoudhury S, Halenar M, Tvrda E, Kovacikova E, Vasicek J, Chrenek P, Baldovska S, Sanislo L, Kren V, Kolesarova A (2019)
In vitro response of human ovarian cancer cells to dietary bioflavonoid isoquercitrin.
Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes 54, 752-757 [PubMed:31271108]
[show Abstract]
Isoquercitrin is a dietary bioflavonoid used as a food supplement. We studied the mechanism underlying its effect in human ovarian cancer cells using OVCAR-3 cell line. Viability, survival, apoptosis, release of human transforming growth factor-β1 (TGF-β1) and TGF-β1 receptor, and intracellular reactive oxygen species (ROS) generation by OVCAR-3 cells were examined after isoquercitrin treatment at concentrations 5, 10, 25, 50, and 100 μg mL-1. AlamarBlue assay revealed that isoquercitrin did not cause any significant change (P > 0.05) in cell viability as compared to control. Apoptotic assay using flow cytometry did not find any significant change (P > 0.05) in the proportion of live, dead and apoptotic cells as compared to control. ELISA also showed that the release of human TGF-β1 and TGF-β1 receptor were not significantly (P > 0.05) affected by isoquercitrin as compared to control. Chemiluminescence assay demonstrated that lower concentrations (5, 10, and 25 μg mL-1) were able to exhibit beneficial effects by inhibiting the generation of intracellular ROS. In contrast, elevated concentrations of 50 and 100 μg mL-1 led to oxidative stress (P < 0.05). We concluded that the beneficial effect of isoquercitrin on ovarian cancer cells may be mediated by an antioxidative pathway that involves inhibition of intracellular ROS generation, thereby limiting oxidative stress. | Omi N, Shiba H, Nishimura E, Tsukamoto S, Maruki-Uchida H, Oda M, Morita M (2019)
Effects of enzymatically modified isoquercitrin in supplementary protein powder on athlete body composition: a randomized, placebo-controlled, double-blind trial.
Journal of the International Society of Sports Nutrition 16, 39 [PubMed:31500646]
[show Abstract]
BackgroundEnzymatically modified isoquercitrin (EMIQ), a water-soluble quercetin, has been shown to intensify muscle hypertrophy in mice. We investigated the effect of EMIQ in supplementary protein powder on athlete body composition.MethodsForty Japanese males who played American football (age: 19.8 ± 1.4 years; body height: 174.1 ± 6.0 cm; body mass: 75.5 ± 10.7 kg) were assigned to a randomized, placebo-controlled, double-blind trial of parallel group. Participants received either EMIQ in whey protein (EW, n = 19) or contrast whey protein (W, n = 20) 6 days per week over 4 months. Body composition was assessed using dual-energy X-ray absorptiometry. Markers of oxidative stress, derivatives of reactive oxygen metabolites (d-ROMs) and biological antioxidant potential (BAP), were assessed using a free radical analytical system. Data were analyzed using a univariate and repeated measures general model statistics.ResultsAfter 4 months, changes in lower limb fat-free mass and muscle mass were significantly greater in the EW group than in the W group (mean change ±95% CI; W: 324.1 ± 284.3, EW: 950.3 ± 473.2, p = 0.031, W: 255.7 ± 288.6, EW: 930.9 ± 471.5, p = 0.021, respectively). Moreover, the EW group exhibited a significantly higher BAP/d-ROMs ratio, antioxidation index, than the W group after 4 months (mean change ± SD; W: 8.8 ± 1.1, EW: 10.3 ± 2.8; p = 0.028). No significant differences in body mass, lean body mass, fat mass, or lower limb fat mass were observed between the groups.ConclusionIngestion of EMIQ in supplementary protein powder for 4 months exerts antioxidant effects and increases muscle mass among American football players.Trial registrationUniversity Hospital Medical Information Network Clinical Trial Registry, UMIN000036036 . Retrospectively registered in 2019. | Omi N, Shiba H, Nishimura E, Tsukamoto S, Maruki-Uchida H, Oda M, Morita M (2019)
Correction to: Effects of enzymatically modified isoquercitrin in supplementary protein powder on athlete body composition: a randomized, placebo-controlled, doubleblind trial.
Journal of the International Society of Sports Nutrition 16, 45 [PubMed:31639004]
[show Abstract]
The original article [1] contained a typesetting error in Table 3 which was mistakenly introduced by the production team handling this article; this error has now been corrected. | Lotha R, Shamprasad BR, Sundaramoorthy NS, Nagarajan S, Sivasubramanian A (2019)
Biogenic phytochemicals (cassinopin and isoquercetin) capped copper nanoparticles (ISQ/CAS@CuNPs) inhibits MRSA biofilms.
Microbial pathogenesis 132, 178-187 [PubMed:31063809]
[show Abstract]
Purified glycosides, Isoquercetin and Cassinopin from Crotalaria candicans were selected for the synthesis of biogenic copper nanoparticles (CuNPs).The designed biogenic CuNPs was characterized and when evaluated against panel of gram negative and positive bacteria, the biogenic CuNPs were found to be more effective against methicillin resistant Staphylococcus aureus (MRSA). Antibacterial, anti-biofilm effects and time kill studies confirmed the ability of biogenic CuNPs to curtail MRSA. Scanning electron microscopy, Crystal violet staining and fluorescent live-dead imaging showed that treatment with sub lethal levels of glycoside capped CuNPs resulted in greater than 50% decline in biofilm formation by MRSA, which implies that anti-biofilm effect of biogenic CuNPs is not dependent on antibacterial effect. Alizarin red assay implied that prolonged treatment of biogenic CuNPs in presence of MRSA, releases Cu(II) ions and hence antibiofilm effect is primarily mediated by NP and is not due to released Cu(II) ion. The NPs caused altered membrane permeability and reduced surface hydrophobicity, thus accounting for its antibiofilm effect. | You W, Zheng W, Weiss S, Chua KF, Steegborn C (2019)
Structural basis for the activation and inhibition of Sirtuin 6 by quercetin and its derivatives.
Scientific reports 9, 19176 [PubMed:31844103]
[show Abstract]
Mammalian Sirtuin 6 (Sirt6) is an NAD+-dependent protein deacylase regulating metabolism and chromatin homeostasis. Sirt6 activation protects against metabolic and aging-related diseases, and Sirt6 inhibition is considered a cancer therapy. Available Sirt6 modulators show insufficient potency and specificity, and even partially contradictory Sirt6 effects were reported for the plant flavone quercetin. To understand Sirt6 modulation by quercetin-based compounds, we analysed their binding and activity effects on Sirt6 and other Sirtuin isoforms and solved crystal structures of compound complexes with Sirt6 and Sirt2. We find that quercetin activates Sirt6 via the isoform-specific binding site for pyrrolo[1,2-a]quinoxalines. Its inhibitory effect on other isoforms is based on an alternative binding site at the active site entrance. Based on these insights, we identified isoquercetin as a ligand that can discriminate both sites and thus activates Sirt6 with increased specificity. Furthermore, we find that quercetin derivatives that inhibit rather than activate Sirt6 exploit the same general Sirt6 binding site as the activators, identifying it as a versatile allosteric site for Sirt6 modulation. Our results thus provide a structural basis for Sirtuin effects of quercetin-related compounds and helpful insights for Sirt6-targeted drug development. | Hobbs CA, Koyanagi M, Swartz C, Davis J, Kasamoto S, Maronpot R, Recio L, Hayashi SM (2018)
Comprehensive evaluation of the flavonol anti-oxidants, alpha-glycosyl isoquercitrin and isoquercitrin, for genotoxic potential.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 113, 218-227 [PubMed:29317330]
[show Abstract]
Quercetin and its glycosides possess potential benefits to human health. Several flavonols are available to consumers as dietary supplements, promoted as anti-oxidants; however, incorporation of natural quercetin glycosides into food and beverage products has been limited by poor miscibility in water. Enzymatic conjugation of multiple glucose moieties to isoquercitrin to produce alpha-glycosyl isoquercitrin (AGIQ) enhances solubility and bioavailability. AGIQ is used in Japan as a food additive and has been granted generally recognized as safe (GRAS) status. However, although substantial genotoxicity data exist for quercetin, there is very little available data for AGIQ and isoquercitrin. To support expanded global marketing of food products containing AGIQ, comprehensive testing of genotoxic potential of AGIQ and isoquercitrin was conducted according to current regulatory test guidelines. Both chemicals tested positive in bacterial reverse mutation assays, and exposure to isoquercitrin resulted in chromosomal aberrations in CHO-WBL cells. All other in vitro mammalian micronucleus and chromosomal aberration assays, micronucleus and comet assays in male and female B6C3F1 mice and Sprague Dawley rats, and Muta™ Mouse mutation assays evaluating multiple potential target tissues, were negative for both chemicals. These results supplement existing toxicity data to further support the safe use of AGIQ in food and beverage products. | Pennesi CM, Neely J, Marks AG, Basak SA (2017)
Use of Isoquercetin in the Treatment of Prurigo Nodularis.
Journal of drugs in dermatology : JDD 16, 1156-1158 [PubMed:29141065]
[show Abstract]
Atopic dermatitis and prurigo nodularis result from complex interactions between the skin, the immune system, and the external environment. The pruritus associated with these conditions greatly impacts patients' quality of life and lacks uniformly effective treatment. A 57-year-old patient presented with severe atopic dermatitis and subsequent prurigo nodularis refractory to numerous standard therapies. The supplement isoquercetin was initiated and he noted significant, sustained reduction in his pruritus after only four weeks. Isoquercetin is a glycoside derivative with antihistamine properties of quercetin, a natural polyphenol flavonoid found in many plants. It may offer itch relief in patients who have failed more conventional therapies. J Drugs Dermatol. 2017;16(11):1156-1158. . | Kim DS, Lim SB (2017)
Optimization of Subcritical Water Hydrolysis of Rutin into Isoquercetin and Quercetin.
Preventive nutrition and food science 22, 131-137 [PubMed:28702430]
[show Abstract]
Maximum production of isoquercetin and quercetin simultaneously from rutin by subcritical water hydrolysis (SWH) was optimized using the response surface methodology. Hydrolysis parameters such as temperature, time, and CO2 pressure were selected as independent variables, and isoquercetin and quercetin yields were selected as dependent variables. The regression models of the yield of isoquercetin and quercetin were valid due to the high F-value and low P-value. Furthermore, the high regression coefficient indicated that the polynomial model equation provides a good approximation of experimental results. In maximum production of isoquercetin from rutin, the hydrolysis temperature was the major factor, and the temperature or time can be lower if the CO2 pressure was increased high enough, thereby preventing the degradation of isoquercetin into quercetin. The yield of quercetin was considerably influenced by temperature instead of time and CO2 pressure. The optimal condition for maximum production of isoquercetin and quercetin simultaneously was temperature of 171.4°C, time of 10.0 min, and CO2 pressure of 11.0 MPa, where the predicted maximum yields of isoquercetin and quercetin were 13.7% and 53.3%, respectively. Hydrolysis temperature, time, and CO2 pressure for maximum production of isoquercetin were lower than those of quercetin. Thermal degradation products such as protocatechuic acid and 2,5-dihydroxyacetophenone were observed due to pyrolysis at high temperature. It was concluded that rutin can be easily converted into isoquercetin and quercetin by SWH under CO2 pressure, and this result can be applied for SWH of rutin-rich foodstuffs. | Dueñas M, Surco-Laos F, González-Manzano S, González-Paramás AM, Gómez-Orte E, Cabello J, Santos-Buelga C (2013)
Deglycosylation is a key step in biotransformation and lifespan effects of quercetin-3-O-glucoside in Caenorhabditis elegans.
Pharmacological research 76, 41-48 [PubMed:23856528]
[show Abstract]
Due to their purported healthful activities, quercetin and other flavonoids are being increasingly proposed as nutraceuticals. Quercetin occurs in food as glycosides; however, most assays on its activity have been performed with the aglycone, despite glycosylation deeply affects compound bioavailability. In this work, the uptake and lifespan effects of quercetin-3-O-glucoside (Q3Glc) and quercetin have been assessed in Caenorhabditis elegans. Q3Glc was taken up by this nematode in a concentration-dependent manner and rapidly deglycosylated to quercetin, which was accumulated in the worm and partially biotransformed to conjugated metabolites. Significant mean lifespan extension up to 23% compared to controls was observed in wild type worms cultivated in the presence of low concentrations of Q3Glc (10 μM and 25 μM), whereas exposure to greater concentrations of Q3Glc (50-200 μM) caused a reduction in mean and maximum lifespan compared with the control. By contrast, treatment of klo-1 and klo-2 mutant worms lacking β-glucosidase activity with 200 μM of Q3Glc led to extended mean lifespan (up to 39%), similar to quercetin aglycone at the same concentration levels. In those mutants, Q3Glc was accumulated without important deglycosylation to quercetin was produced. Taken together, these findings indicated that Q3Glc was taken up by the nematode in greater extent than quercetin, and that deglycosylation and subsequent aglycone accumulation in the worm appeared as key points to explain the observed lifespan effects. The obtained results also suggested that facilitated absorption should be more important for the uptake of quercetin derivatives than passive diffusion. | Yang JH, Kondratyuk TP, Jermihov KC, Marler LE, Qiu X, Choi Y, Cao H, Yu R, Sturdy M, Huang R, Liu Y, Wang LQ, Mesecar AD, van Breemen RB, Pezzuto JM, Fong HH, Chen YG, Zhang HJ (2011)
Bioactive compounds from the fern Lepisorus contortus.
Journal of natural products 74, 129-136 [PubMed:21261296]
[show Abstract]
Phytochemical investigation of the whole plant of Lepisorus contortus (Christ) Ching led to the isolation of five new phenylethanoid glycosides (1-5), each containing a caffeoyl group, a new flavonoid glycoside (10), and 14 known compounds (6-9 and 11-15, syringic acid, vanillic acid, phloretic acid, diplopterol, and β-sitosterol). This is the first report of phenylethanoid glycosides from the family Polypodiaceae. Compounds 1-15 were evaluated for their cancer chemopreventive potential based on their ability to inhibit tumor necrosis factor alpha (TNF-α)-induced NF-κB activity, nitric oxide (NO) production, and aromatase, quinone reductase 2 (QR-2), and COX-1/-2 activities. Quercetin-3-O-β-d-glucoside (15) demonstrated inhibition against QR2 with an IC(50) value of 3.84 μM, which confirmed kaempferol/quercetin glycosides as the active compounds to inhibit QR2. The compound also demonstrated NF-κB activity with an IC(50) value of 33.6 μM. In addition, compounds 1, 2, 4, and 6 showed aromatase activity with IC(50) values of 30.7, 32.3, 26.8, and 35.3 μM, respectively. |
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2020-07-29
